Accidental MILF Hunter

[This story contains themes including but not limited to orientation play, infidelity and heterosexual relations between women and men in non-heterosexual relationships.

Reader discretion is advised.]

It started out as an accident, Raphael swears on his life.

One of the best on the football team plus a stickler for the status quo, Raphael was a full closet case during high school. He kept his eyes on the state championship prize and used every excuse to reject the girls lining up at his door, no matter how hot they were to the straight male population. But once the end of senior year was coming to a close, a sparkling trophy on display for the whole school and a full ride scholarship to his chosen college in his back pocket, Raphael didn't know what else he could say to avoid the inevitable.

He quelled all the rumors by sacrificing his first kiss with some cheerleader at the senior prom. It felt like a chore having her as his date, all the pictures, the compliments, the high pitched whining. Looking back, Raphael wished he had picked someone lower maintenance - maybe even exercised his (sadly non-existent) gaydar to find a closet lesbian as a beard.

Raphael's biggest regret was that prom night. Driving her back, she had started coming onto him and in a state of panic, he went along with it. Thus he ended up giving his virginity up like it was loose change - not that the girl seemed to notice as she came over and over on his massive dick.

But for the football player it was an experience he was glad ended quickly. He had almost exhausted his mind's spank bank to keep himself hard throughout the twenty minute ordeal before she collapsed from exhaustion and he could finally go home and wash himself clean.

With her gossip proving that he wasn't gay but instead just one of the many sexy straight jocks in the school, Raphael could pretend to act picky and was able to rebuff advances for the rest of his high school days.

Moving across state for college, Raphael wasn't sure if he could break out of his shell. The first few months getting used to a new place and a new team had got him thinking nothing would change. But he had a lucky break in the form of Levi Johnston.

Top jock Levi turned out to be gay and in a two year relationship with childhood friend Andre. This fact was well-known by all of the football team but to Raphael this was his signal. He came out to the football team as well as friends and family, reveling in their massive support.

He smiled widely, as his teammates and especially Levi, patted him on the back, praising him for having the confidence to take that big step forward.

"My college life can truly begin," Raphael had thought happily.

That's when all the trouble began.

***

Matthew was Raphael's first boyfriend.

A staunch supporter of the college's football team, they locked eyes across the field and the rest was history. A stunning smile and a hot body and mind to boot, Raphael was surprised he had scored it big time on his first shot. They went on the cute little dates he had been dreaming of since he was a young, taking long walks along the nearby beach, playing carnival games at the pier and kissing as the sunset fizzled beyond the horizon.

And what a glorious feeling it was kissing a man. Where his first kiss felt like smooching a dead fish, kissing Matthew was all fireworks and sunshine and everything good in the world. He loved the feeling of Matthew's strong tongue battling of dominance, how he cupped his boyfriend's stubbled jaw to pull himself deeper. The firmness of the masculine body underneath him as they made out in Raphael's college dorm was a drug he was addicted to.

After several months of dating, Raphael was waiting for Matthew in a tucked away corner of the cafeteria, having received a text with the subject line 'important'.

"Hey Raphy, sorry I'm late. The media professor was being such a bitch again. I can't believe she made us stay back to listen to her scold her T. A.," Matthew ranted, giving Raphael a quick kiss before sliding in next to him.

"It's ok babe I just got here," Raphael responded. "So what was so important you had to hide us away from our friends? Are you cheating on me? Oh my god is it with that annoying project partner? I knew it! You were always a sucker for the enemies to lovers trope-" he began teasing before Matthew shoved a chicken tender abruptly into his boyfriend's mouth.

"Of course not you big oaf. I was just thinking, for our 4 month anniversary we could do something a little special," Matthew began fluttering his eyelashes, letting a wandering hand creep up Raphael's thigh, "if you catch my drift."

Raphael sucked in a sharp breath, willing his erection to stop creeping down towards his boyfriend's hand. "Oh my god it's finally happening," his mind screamed as the widest smile took over his face.

"Are you sure Matty? You know I don't want to pressure you into anything."

Matthew slapped his boyfriend's shoulder playfully.

"Please. I've been wanting this since I saw your hunk of a body making that touchdown during your first game. And as this will be both of our first times, I think we shouldn't wait any longer."

Sweat began forming on Raphael's brow at his boyfriend's incorrect assumption about his non-intact virginity. Matthew knew it was his first relationship but Raphael didn't disclose his venture during senior prom - not that he wanted to recall it.

"Sounds like a plan babe."

"Perfect then. How about this? For our anniversary we go out for a nice meal and head back to my home? My mom is out on a business trip so it will just be you and me enjoying the night?"

"That sounds wonderful Matty," Raphael answered as he planted a soft kiss on Matthew's forehead.

The anniversary dinner was a simple affair at a local Italian place which had the couple's favorite dishes and one of Raphael's favorite cooks.

"Congratulations on your anniversary sweeties, you two look very dashing all dressed up," Mrs Rossi cooed at Raphael and Matthew. Raphael had become close with the spritely 48 year old woman, after being introduced to the restaurant by his teammate Leonardo Rossi. "Leo is whipping up some tiramisu on the house so just sit tight," she squeezed Raphael's shoulder causing him to blush as she walked to the back.

After an amazing dessert, Raphael was ready for the main course. In the car, Matthew couldn't keep his eyes and hands off Raphael, drawing teasing lines across the football player's muscular physique and caressing his thick thighs through his tight jeans. He was able to sneak in some tender kisses on Raphael's neck before Raphael parked at Matthew's home, sweeping his boyfriend up effortlessly and beginning a passionate make out session towards Matthew's room. As he lay Matthew down on the bed, Raphael's stomach began pooling with heat with the reality that he was finally going to lose his gay virginity. He had loosened up as best he could earlier in the day (with some tips from Levi and the internet his only help) so only their clothes stood in the way.

Their shirts were the first item to come off and Raphael groaned at the contact of their lightly hairy chests pressed against each other, how Matthew's flat chest was squished by his own meaty pecs. Matthew's lips still tasted like the sweet tiramisu as Raphael stole one last kiss before giving attention to his ears and neck with light bites. He made his way down to a nipple, stealing a bite before massaging and sucking them, enjoying the delicious moans of his boyfriend above him.

Matthew decided he wanted a turn as he pushed Raphael onto his back, grinding their clothed dicks against each other. He returned the favor as he began worshipping Raphael's hunky body, groping and massaging the football player's beefy chest and kissing each of his abs. Though the actions barely elicited any pleasure for Raphael, he moaned encouragingly to his boyfriend.

Just as Matthew had undone the button of Raphael's jeans, a blaring sound came from Matthew's bedside table. Though Matthew rolled his eyes towards his phone and told his boyfriend to 'just ignore it', once Raphael's jeans were tossed onto the bedroom floor, both men were now soft as the ringing continued.

"Sorry babe, let me see what it is."

Peering over, Raphael saw the 5 missed calls from a person called 'stupid groupmate #2' before watching his boyfriend try not to lose his shit for 5 minutes.

"Oh my fucking god of course this happens! I finish my part on time so I can finally have sex with my hot boyfriend and these worthless teammates cockblock me instead," Matthew collapsed back onto the bed, leaning into the gentle touch of Raphael's hand on his cheek. "I have to head across town to their apartment to sort out everything, an hour tops. I am so sorry babe but if this isn't submitted by tomorrow morning I'll fail the course."

Though Raphael was weeping internally and his dick was weeping externally, he leaned down to kiss his boyfriend.

"Don't worry Matty, I can wait. Give those fuckers a piece of your mind. After the project is over I can go over and rough 'em up if you'd like," Raphael joked, adding to his threat with a flex of his juicy bicep.

"I'll keep you to your word," Matthew laughed as he redressed, heading towards the door, "see you in a bit babe."

Hearing Matthew leave the driveway, Raphael laid back on the bed, breathing in the warm summer air and the sweet lavender aroma that hung dreamily in Matthew's home. A little tired from his afternoon football practice, Raphael couldn't help but drift into a nap, hoping his boyfriend would soon return and wake him up.

As Raphael consciousness crept out of slumber, it felt as if he were lucid dreaming. His body felt the most relaxed he had ever been, sinking into a warm pulse that fluttered through every muscle like the gentle rocking of the tides. At the same time he felt wound up tight as if he were on the precipice of bliss that he couldn't quite reach. But as the feeling pooled down lower, it became irresistibly hotter and hotter; Raphael's body flushed in pleasure even in his subconscious.

The scent of lavender flooded his senses as Raphael's mind settled back into reality. He could now feel the rocking of the bed, something passionately moving against his lower regions. Raphael let out a sharp gasp when the insurmountable pleasure and tightness gripping his swollen dick finally reached his brain.

"Fuckkkkk. Yes, just like that babe. Feels so good."

Did Matthew get impatient? Raphael thought he was the one getting fucked but he maybe that wasn't the case now.

The walls of the slick cavern he was fucking into fluttered against his dick and Raphael could feel himself getting closer. Wanting to climax alongside his boyfriend, he opened his eyes to an unexpected sight.

A woman was energetically bouncing up and down his thick cock, her pussy attempting to suck him dry. He watched her sweaty form drive herself over and over on him, the shaking of her big tits making him dizzy. Her eyes were closed, drinking in the pleasure from fucking herself on such a stud.

"What the fuck?! Who are you?" Raphael withdrew himself from her. He watched as the woman acted more annoyed than anything else, her eyes and body creeping up towards his retreating form.

"You know, it isn't nice to leave a lady hanging? I was so close," she licked her lips, "and I know you were so close to flooding my pussy with your gay jizz, Raphael dear."

While his brain reeled trying to figure out how she knew him, he was unprepared for the sucker punch to his gut - or rather the steaming cunt re-enveloping his throbbing erection. He groaned at the invasion, at how her finger squeezed his muscular body in just the right way, like she was seasoned at dismantling hot guys until they were putty in her hands. Using the leverage of her fingernails digging into his sweaty pecs, she drove herself harder onto him and purely on instinct, Raphael felt his body rutting back trying to chase that sweet finish he almost had earlier. That's when it clicked.

The tousled raven black hair, the sharp model-like facial features, the warm brown eyes.

"Matthew's mom? Why are you here? Matt said you were on a business trip?" Raphael queried, only asking the most important questions of course.

Matthew's mom only laughed.

"I finished early and wanted to surprise my darling boy. But imagine my delight when I found a tasty treat on his bed instead. I haven't had a cock like this since my college days, sure takes me back."

Raphael broke into a sweat that was not a result from the hot sex he was currently occupied in, reaching over for his phone on the bedside table. He could only make out the phrases 'fucking stupid bitches' and 'sleeping there tonight' before Matthew's mom grabbed his wrists, pinning them down so his attention was back on her. Raphael knew he could throw her off easily but he knew that this vixen wouldn't let him go until she had drained him dry.

"Mrs Malek, why are you doing this? I'm Matthew's boyfriend! This shouldn't be happening!" Raphael cried, futilely trying to wriggle himself out of her hold but the motion instead caused him to grind into her harder. He felt like he was going to explode at any second - physically and emotionally. But the older lady had complete control.

"I know that you two were planning to lose your virginities to each other. But once I saw pictures of you, I knew that my poor son couldn't give you the first time you deserve. Only a mature pussy like this," she gestured at her slick cunt, how it gripped deliciously around Raphael's thick shaft, "could ever accomplish that."

"I'm not a virgin!" Raphael shouted indignantly like that was the most necessary part to rectify. "But fuck! Pussy didn't feel like this. That cheerleader was horrible but this," he thrust up feeling how her pussy massaged his whole length, "feels nothing like that."

"That's the beauty of experience, stud. Your little girls back home couldn't even come close."

Feeling all his retorts drifting away, Raphael groaned as they fucked harder into each other, the give of Matthew's bed letting him bounce her on his gay dick. He noticed that her body was in stunning shape, the natural weight of her hips making each slam into her tight cunt even better. As he gripped her waist, Matthew's mom leant down capturing his lips in hers. He was overwhelmed with the comforting scent of lavender as the deluge invigorated him to fuck her faster and harder. Raphael felt her pussy get impossibly tighter and wetter and his body couldn't handle it.

"I'm coming, fuckkk!" Raphael groaned as he came hard inside her, panting at each wave of her quivering cunt as she orgasmed as well. Raphael continued to make out with her, his face slick with her spit as his tongue delved into her mouth, swallowing all of her squeals of pleasure. The bed still continued to rock as they fucked through their mutual climax, the drenched feeling all over his still rock hard cock and the sweet pleasure as she suckled his sweaty neck the only things he could recall as sleep took over again.

The dawn had begun to break as Raphael gasped, his eyes flying open. His hopes that he had just had a vivid wet dream/nightmare were shattered as he felt the sticky mess on his torso and attached to his dick, Matthew's mom snugly still planted onto him. She was sleeping soundly on his firm chest, her breathing causing her pussy to quiver against his cock. He slowly drew his dick out, watching in awe at the flood of jizz he had deposited into her creamy pussy dripping onto his abs. Raphael supposed that she must have ridden him to another climax after he knocked out.

"Damn she's insatiable," he thought.

Raphael watched his traitorous dick plump as he sat up from the bed, checking his phone to make sure Matthew wouldn't be coming home suddenly. With the coast clear, he quickly got dressed and left the place where he felt like he had truly lost his virginity.

The gay couple didn't have an opportunity to resume their passionate night, with Raphael seemingly unavailable whenever his boyfriend called. He threw himself into football, going to frat parties with his teammates and cooping up in the library to study - all to avoid looking into Matthew's warm brown eyes. Matthew was getting sick of it.

"Where the fuck are you man? It's like you're a ghost on campus? I'm trying to make this work but you won't show up!"

Raphael blanched but steeled his face as the guilt crept in. Every moment that Matthew had seized with Raphael during this time felt like a downward spiral, his beating heart slowing and all Raphael could do was attempt to see Matthew like he used to. But all he could picture was a flushed body, a heavy set of tits and a searing cavern his dick desperately wanted to return to. Something that he knew Matthew couldn't offer.

"It's because I don't like you anymore!- at least not in the way you want me to. I'm so sorry."

Raphael felt his stomach drop as he watched tears collect in Matthew's eyes.

"I guess we're over then," his now ex-boyfriend whispered, not sparing a second glance as he walked away.

The walk back to his dorm room felt like he was soaking in melancholy. But worst of all, the intense heartbreak he should've been feeling was replaced by the wanton heat pooling in his groin as he looked at the piece of paper that had been tucked into the jeans he had worn that anniversary night.

'Call me xoxo - Maya'

***

Ivan was Raphael's second boyfriend. Or rather he would've been Raphael's first hookup if it had ever come to fruition.

Depressed and trying to take his mind off Matthew and more importantly Matthew's mom, he continued to throw himself into college life, a non-alcoholic beer not an unusual thing in his hand. It took a while afterwards to realize he had cum inside her raw (several times in fact) but he took the lack of confrontation from Matthew and his mom to be a good sign he wasn't going to become a father anytime soon. After reaffirming that he still was indeed gay, even though he had discovered that pussy could feel amazing, Raphael came up with an amazing idea if he had to say so himself.

He could simply fuck the confusion out of his system. More specifically, to fuck and be fucked by a hot dude so everything could go back to normal.

So the football player had a new mission during his parties. Instead of fucking around with his teammates, Raphael was on the hunt for solid dick. Luckily Matthew didn't go to frat parties and somehow his tryst with his mom stayed hidden so Raphael's title as a sexy single gay guy was free for him to market. After surveying possible candidates for his first gay time he landed upon a guy from a neighbouring college. He had seen him from time to time, a general staple in the mass of people who turned up to these types of events. A short king with a mop of bleached blond hair crowning a soft face, they were the complete opposite of Matthew. Their only similarity was the nice bulge and bubble butt that stuck out from his chinos which didn't hurt his case at all.

The only things Raphael gathered were that the guy's name was Ivan and that he had a smooth voice Raphael wanted to make sing, before they were making out, heading upstairs to find an available room. He opened the first door.

"-i! Right there, fuck right there," a woman's voice quietly moaned.

Raphael averted his eyes, only catching a glimpse of a sculpted back and a jersey thrown haphazardly on the floor, before promptly shutting the door.

"Guess your teammate is getting busy," Ivan said, wiggling his eyebrows.

Remembering to actually knock, third time was the charm as the two men pressed each other onto the bed, swapping spit and rolling around till they were only in their underwear. Flashes of a curvaceous body with a distinct lack of dick were pushed out of Raphael's mind as tried to get his dick to focus on the hot guy panting under him. But before he could even slip his fingers under Ivan's waistband, to finally grab a real life warm-blooded cock, he almost fell off the bed, startled by the sound of sirens outside the window.

They put back on their clothes, Raphael greatly thankful that Ivan settled for a raincheck the next day. After funnelling out of the shut-down party due to noise complaints, he decided to not give into his horny thoughts and relieve himself, needing to save his cum for a hot guy instead of the temptress living in his mind.

"Sorry Raph, somehow I ran out of condoms and lube but I guess I've been fucking too much these days," Ivan explained and put on his shoes for a quick drop by to the store, "you need anything?"

"Only for you to come back quickly," Raphael joked, trying to hide his worries of being left alone, "you sure no one is coming over right?"

"Of course! My older sister is halfway across the country with my dad for a convention thing and my mom is visiting family for the weekend. The house should be free."

"Thank god because I don't wanna miss this in me," Raphael teased while cupping the bulge of the shorter guy.

"Well you better shower first. I can't believe you came here straight after practice all stinky like that. We can build up a sweat together later," Ivan laughed, "towels are in the bottom cabinet in the bathroom. Clothes aren't necessary but just grab something from my room if you need some."

"I guess I have to take care of this hot bod alone," Raphael quipped back, flashing his chiseled abs and watching Ivan smile before heading out the front door.

A relaxing lukewarm shower was what Raphael needed after his gruelling football session. He had almost forgotten to stretch himself out for Ivan's big cock before he heard the bathroom door creaking open. The sound of melodious humming followed.

"You got back fast. Couldn't waste the opportunity to wash me off?"

When Ivan didn't respond, Raphael peeled back the curtain. Two screams echoed in the bathroom as Raphael used the shower curtain to hide himself from the short woman wearing headphones. Though she was naked as well, once she took a glimpse of the football stud in his birthday suit, her scream turned into pondering silence before she let out a hum as if she was solving a case. Leaning back against the sink, she removed her headphones and smiled at the wide-eyed jock.

"Sorry for coming in during your shower time, I was so distracted by my music," she licked her lips, "but now I have something better to be distracted by. I'm assuming you are my son's latest boy toy?"

The trickles of something like deja-vu prickled in Raphael's mind as he turned off the shower tap, finally averting his eyes from who he now understood was Ivan's mom.

"Uh, yes ma'am. Would you mind leaving for a second while I get dressed?" Raphael asked politely. His eyes bulged as she flexed her petite form, letting out an exasperated sigh.

"But I just got home from such a long drive. Don't worry, I won't look." Ivan's mom turned around and covered her eyes.

Trying to be quick, Raphael exited the shower, fumbling around for a towel that wasn't there. He really wished he had borrowed some of Ivan's clothes. Looking up, his gaze met the dilated eyes of a woman in the mirror and he realised she was drinking him in, now in his completely naked form. Her eyes paid particular attention to his hard cock, wet and throbbing.

"My, my, what do we have here? You were going to forgo this poor woman a look at this massive weapon?" she flirted. Raphael swerved out of her way when she moved but inadvertently trapped himself where she had once stood. His lower back pressed against the bathroom sink and he watched her small hands gently grab his erection.

The woman's two hands barely covered the circumference but the way her fingers explored each inch had Raphael clenching the sink till his knuckles turned white.

"Please, Ivan could come home any minute," he begged.

"Better make this quick then," was all she said before she dug in.

Only his head could breach her small mouth but it was enough for her to suckle the steady stream of precum. The sweep of her tongue on his frenulum made him cuss as his hands instinctively grabbed the back of her head, his body inching towards the pleasure. His moans and her slurping melted into the drone of the bathroom fan as she made her way down his cock slowly. Once the lady had hit her limit, her hands took care of the rest of his inches, hands squelching with the mess of spit and precum covering his cock and swelling balls.

Ivan's mom settled into a slow drawn out pace, making Raphael whine about her lies of this being quick. Raphael could leave anytime but all it took was a deft sweep of her tongue and he was back to being a moaning mess against the sink. A gentle tug of his full nuts caused his muscles to tense and he removed her from his dick.

"Fuck, I'm cumming!"

Raphael let out a drawn out groan as thick ropes of cums splattered on Ivan's mom's face, drenching her in his gay seed. Her hands continued caressing his pulsing ball sack while he stroked his cock vigorously, trying to prolong the pleasure. Panting heavily as the last drops were licked up by the woman, he stroked her cum covered cheek.

"Damn you look so pretty in my cum," Raphael thought before blushing in mortification as he realised he had voiced his thoughts aloud. Ivan's mom's giggles were cut off when both of them became startled by the slam of the front door.

"Mom, are you home?"

Footsteps resounded down the hallway towards the clandestine couple.

"Raph, you in there?" Ivan softly knocked onto the door.

This would've been the perfect opportunity for the gay jock to slip out, away from the mature nymph slowly shifting over to sit on the sink counter, but if Ivan spotted his mom covered in his cum he would have a lot of explaining to do. Worst of all, Ivan would definitely not be down to take his virginity. Raphael was about to make an excuse to get Ivan away for a moment but his mom was faster.

"Honey is that you?" Ivan's mom asked, acting like she wasn't currently covered in the gay jizz of her son's should-be lover, "I'm just about to take a long bath. Your grandparents didn't need help so I came back early."

"Oh that's cool. Also, did you happen to see my friend when you came home? Big guy, looks like he'd play football? I had to grab something quick so I left him here but I can't seem to find him?"

Before Raphael could protest, two hands reached high to grab his upper chest, dragging him into her bosom. Though her tits were small, Raphael felt stiff but calm at the sweet aroma and lingering sweat that filled his senses. Raphael's chiselled face was slowly forced to trace down Ivan's mom's slim body before his nose rested in the soft bush above her dripping cunt. The candy notes from earlier intensified as his mouth grazed her clit. He instinctively sucked on the nub, causing her to squeeze her thighs together, effectively trapping him in her clutches.

"Sorry, I dropped something," she replied, excusing her earlier pause, "I didn't see anyone honey."

Their conversation became a murmur in Raphael's ears as he began licking around her wet folds, finding that she tasted absolutely divine. Strong hands clasped onto her hips as he made his way down and deeper where he probed her entrance with his tongue. It was like a faucet of ambrosia, his mouth digging into her molten wet heat until it felt overwhelming. The lady above him attempted to stifle her moans and pulled him in tighter between her thighs, her feet lazily drawing patterns on the stud's muscular back.

"That's strange, he didn't text me about anything. Well I guess I'll be out tonight again. Don't worry about me, I'll be staying over at Dee's."

"No problem son, stay safe!" Ivan's mom called after him before her voice bled into moans now that the mother and gay guy were alone. She released Raphael, giving the football player a moment to catch his breath and lick his lips clean.

"Not bad for a gay boy, but your technique is sloppy. I guess only a real man would actually be able to make me cum."

The competitive streak in Raphael was ignited. He knew that he was doing well if the constant flow of juice that he lapped up was anything to go by. Standing up, he lifted the woman like she weighed nothing, flipping her upside-down so he was face to face with her pussy again. Her soft body was firmly pressed against Raphael's hulking frame as he held her up in his thick arms before he devoured her once more. The mother was unprepared for this onslaught, the blood rushing to her brain and the passionate swipes of Raphael's tongues on her sensitive folds eliciting a drawn out moan. Raphael held her steady with one arm as his other grabbed his re-energised cock.

"You wanted a real man? Here's a real man's cock for you. Get to it." The words didn't feel like they were coming from him, corrupted by another wasted chance to get with a guy and the audacity of this woman coming for his manlihood.

The sound of her choking on his gay dick was music to his ears and he continued his assault on her pussy, using his free hand to pry her folds open to delve in deeper. Raphael could feel his lower regions getting drenched again in her spit as she struggled to take him in. He leaned against the sink counter which gave him extra leverage to thrust into her small mouth, making her gag and her throat tighten deliciously around him. He moaned into her wet heat as a scream reverberated on his dick.

Raphael was like a starving man as he drank up her orgasm. He tried to prolong it, two fingers knuckle deep and swallowing as much as he could. But it wasn't enough for his stomach, he wanted more. Luckily for him Ivan's mom was thinking the same thing. He lowered her down, internally grinning at how wrecked her face looked. She smiled in return and moved towards the bath in the corner of the room, turning on the water.

"Sit down pretty boy," she gestured towards the triangular ledge where the bath and room shared a corner. Raphael complied, displaying his full muscular visage to her by subtly flexing his biceps, abs and dick and watched as she straddled him. He dove into her small tits, making out with each nub until she was mewling under his touch. She slowly ground against his dick that was sandwiched in her firm butt cheeks, dripping precum on them. The tap was turned off as the bath was filled with lukewarm water.

"I think it's time for me to relax now. Won't you help me with that?" Ivan's mom moved so her back pressed against his firm chest. Raphael naturally moved to hold her up by her inner thigh and waist, feeling the heat bleeding from her pussy just inches above his leaking dick. Well if he couldn't get fucked tonight, he might as well do the fucking.

"Yes ma'am."

"Please, call me Isabelle," was all she whispered as she sunk down onto the jock's long rod.

Though the slickness of her cunt made the descent smoother than expected, Raphael's dick was met with resistance quickly as he unknowingly ground against the entrance of her cervix. But it was way better compared to when he had lost his virginity and now that he was fully awake to comprehend it, his gay cock had never felt anything better in his life. Whatever inches that could fit into Ivan's mom were massaged thoroughly like he was being caressed by the smoothest silk imaginable. He could feel her warm fluids trickle down his exposed shaft until they settled in the hairs that covered his throbbing ball sack.

"Fuck, Isabelle you feel so good," was all Raphael could mutter as he slowly rocked her up and down his cock. It was truly a time for relaxation as both parties sunk into a toasty morass of pleasure. Raphael gently suckled Ivan's mom's tits, teasing her nipples with his tongue and nibbling them, coaxing out cries of delight from the lady. In return, Ivan's mom languidly played with her clit, each shock of pleasure causing her to clench on Raphael's pulsing hard rod.

Feeling his time was near, Ivan's mom let out a yelp as Raphael trapped both of her legs in a bicep hold, propping her up with his other hand supporting her ass. He felt the extra leverage he needed to drive his long dick up into her, somehow being able to fit an extra inch into her already stuffed pussy. Her juices were flying out and he picked up the pace, his nut sack a blur as he fucked her fast and furious. She could feel every honed ab and muscle flex against her back as she could only just take the onslaught the gay jock was providing. When she came hard on his cock for the umpteenth time he brought his lips onto hers, moaning at the feeling.

Another bucket load of gay jizz was expelled instead this time into her pussy. It felt like she was bulging from the insufficient space that his cum was attempting to claim, how it only had the option of travelling further into her as his thick cock plugged her entrance leaving no chance to escape. Raphael ground himself impossibly deeper into her, joining her in slowly rubbing her swollen clit to cajole more delicious waves of her orgasm on his throbbing cock.

They continued to kiss as they came down from their mutual high, rubbing themselves all over each other.

"How embarrassing that your chest is bigger than mine," Ivan's mom stated, groping his heaving pectorals and leaning down to tease them with her mouth causing Raphael to flinch in pleasure, "but I guess it's to my benefit."

"Don't worry, I love your tits Isabelle. They're so fun to play with," Raphael murmured in a pleasure-drunk daze, slowly massaging her small breasts.

As they felt the bath water become cold, Ivan's mom moved so her hands were propped onto the front of the bath, cum-filled pussy facing the gay jock.

"So how about round 2?"

Reaching over to the sink counter where his phone was, Raphael sent an apology to Ivan citing a family emergency and calling for a raincheck. He knew deep down nothing would come out of it though.

"I guess while I'm here now," Raphael thought.

All the stud gave was a slap of his dick on her pussy before he plunged into her, kicking off a session that would last through the night.

***

Leonardo wasn't Raphael's next boyfriend but instead the third guy he had ever tried sleeping with.

Whatever he had going on with Ivan fell through fast. After finding out thankfully during their fifth round that Isabelle was on birth control still, he and Ivan had tried again. However, Raphael couldn't even get hard and Ivan didn't like that attack on his ego. So they stayed acquaintances, only seeing each other at frat parties and drinking up a storm together when their inhibitions were low.

In those parties, Raphael (whose generally scatterbrained mind was trying to understand his weird not quite bisexual lean towards older women) didn't notice his teammate Leo running off with boys and girls in the background. It was only until he accidentally stumbled upon a man balls deep in Leo who was balls deep into woman whilst trying to find an empty room to sleep in did he realise. That's when the (questionably) smart hypothesis that maybe a guy who was bisexual would be able to take Raphael's gay virginity successfully.

So one day after football practice, a sweaty Raphael excitedly asked an equally sweaty Leo out on a date. The surprise on Leo's face quickly morphed into a handsome smirk.

"Sure dude, why not. I wouldn't want to say no to a hot stud like you," Leo exclaimed. "How about this Sunday we go to that new Italian place? My pa and ma want me to scout them out."

In an attempt at seduction, Raphael wore his tightest dress shirt that perfectly hugged his defined chest and abs, his biceps bulging with every flex of his arms. Coupled with a pair of equally tight jeans and leaving a few shirt buttons undone, he was pure eyecandy for the other diners.

All Leo gave to Raphael was a low whistle noting how smoking he looked. Then all his attention diverted to the restaurant itself. He was invested in analyzing everything from the food to the decor to the efficiency of their waitstaff. Raphael initially was annoyed at Leo's enthusiasm not being directed at him but slowly fell into the fun of the game. Being a regular at Leo's family restaurant 'Rossi's', he enjoyed comparing the various dishes they had ordered, laughing and discussing with his teammate on what was better or worse.

"Hey if you eat any more of their risotto I'mma tell ma on ya," Leo quipped as Raphael took a big bite of the rice dish.

"Yeah you go try that and I'll tell her that you finished their lasagne in a minute flat!" Raphael shot back.

Somehow all their desserts turned out to be inedible, dampening their food experience but giving Leo fantastic news to bring to his parents. With that train of thought they decided to rock up back at 'Rossi's' for a tiramisu to share.

"Raphael, baby, long time no see! My, have you grown even bigger?" Mrs. Rossi greeted, hugging the football player. Through the thin fabric of his shirt, Raphael tried to ignore the warmth of her plush chest against him and her hands on his muscled back.

Settling down as closing time neared, the jocks split the tiramisu and a bottle of wine. A little tipsy, Raphael leaned in for a kiss hoping to finally have some sexy contact with another man. He could taste sweet-bitter mix as he explored Leo's mouth. But no sparks flew, no heated passion that rushed from his head to his chest to his groin flared as they pulled apart. The look in Leo's eyes told him it was mutual.

"Well that was hot and all but it kinda felt like kissing a brother. I guess the team won't have a hot football couple this season," Leo joked, Raphael chuckling and nodding in agreement.

The brief modicum of unease melted away as they finished off the bottle of wine, Raphael finally feeling a bit warm under the collar and glad he left those buttons undone. With a shout from the kitchen when 10pm hit, the two jocks were roped into helping close up shop. Under the direction of Leo who was going to help his father sweep the front-of-house, Raphael made his way to the backroom to put something away on the top shelves.

Humming a tune and contemplating his next move to lose his gay virginity, he didn't notice the figure that had walked in as well, crashing into them. Instinctively he shielded them as they fell onto the floor.

Feminine hands were splayed on the mounds of his chest and a flushed Mrs. Rossi was staring down at the jock.

"Oh my baby are you okay?" Mrs. Rossi exclaimed, leaning over in her straddling position to inspect Raphael's head for signs of injury.

"All good Mrs. Rossi, I'm built to be sturdy. Are you okay? That must've given you a fright," Raphael shifted so he was sitting up, his back leaning against the backroom door.

"I'm fine thanks to your quick reflexes. But that was quite a hard landing, let me check if you're bruised anywhere."

The Italian mom deftly began plucking each of Raphael's remaining shirt buttons, ignoring the squawk from the football player at being exposed. His chest was red from the alcohol from earlier but his mind was crystal clear as he shivered from her hands tracing over him. She examined his upper body, running her cool hands over each plane of muscle. Then Raphael felt her freeze.

"Something wrong? Is it bad?"

"Everything looks mostly fine, just a slight bruise on your left shoulder," Mrs. Rossi whispered, "but I can tell you are a healthy young man."

Raphael felt a chill ripple through him as he felt where his blood was rushing towards. It was unmistakable in his tight jeans, his massive rod unsuccessfully straining up towards the shapely curve of Mrs. Rossi's ass.

"Oh my god I am so sorry Mrs. Rossi, I guess the alcohol is getting to me. Let me get up," Raphale tried to move but was stopped by the Italian mom, who instead gave a firm squeeze of his erection.

"Baby no need to worry. I can help you."

It was like a flip was switched. Raphael watched the woman's eyes glaze over, slowly slinking her way down till her face was inches from his fly. All Raphael felt was déjà vu.

"Mrs. Rossi, stop it. Mr. Rossi and Leo are right outside," Raphael hissed. He took a sharp intake of air as his cock was freed, jerking as a cool hand wrapped around the base and a searing hot tongue flicked out to sample his precum.

Raphael knew he should be feeling sick at the woman's hot mouth working on his throbbing tool. Unlike the other ladies he had fucked, this one was one he had almost treated as a second mom - a mom away from home if you will. But all his lizard brain could churn out was immense pleasure as he began thrusting up into her mouth, grabbing her free hand to roam all over his chiselled stomach.

"Fuck Mrs. Rossi, you really know how to take care of a customer."

The lady smiled as she fondled the jock's swollen nuts.

"I aim for 100% satisfaction. Especially for diners with something hefty in their pocket. And please, call me Lucia. Mrs. Rossi makes me feel old."

Though Raphael knew she was entering her fifties, Lucia didn't look a day over thirty if only for the laugh lines on the face that was devouring his cock. In the silence of the storage room, save for his soft panting mixed with the slobbering over his dick, he could make out the booming of voices in the restaurant. Lucia, noticing the jock looking over at the door, chuckled with a mouth full of delicious jock meat before replacing it with the stroking of her deft hands.

"Don't worry, they're just being hot-blooded men. My husband always thinks he knows best and you know how Leo gets when he's riled up. They'll keep themselves occupied for at least another 20 minutes so just relax baby."

All Raphael's muscles melted under her command as he felt free to sink into the slick wet feeling of her mouth on his cock, threading his fingers through her hair to move it out her face. It gave him a better look of the experienced woman, how her lips stretched over the thick head before she slowly swallowed a few more inches more, her free hand paying attention to the rest of him. A few minutes went by as she became accustomed to his throbbing member and she withdrew, leaving his damp cock to cool in the storage room air. Raphael watched dazed from the ground as Lucia moved towards the shelves and grabbed a can. He didn't realize he could get any harder as she unloaded a fresh dollop of whipped cream that sat snug on the pulsing mushroom head of his dick, its warmth making the topping begin to trickle down towards the base.

"I always like my desserts with a little whipped cream," Lucia quipped.

She began by sucking his cock head, savoring the sweet and salty concoction being provided. Then small licks made their way down his shaft like she was a cat trying to clean their saucer of milk. When there was no trace left, she sprayed more onto his pole, repeating the actions until the jock was a writhing, sticky mess. His pubes and stomach were covered in sweet cream and saliva, shining in the fluorescent light of the room. His dick looked even better as it glowed bright and throbbing in the foreground of Raphael's fantastic view.

A tender suck of his filling nut sack caused Raphael to let out a deep moan. In response, Lucia nestled her face deeper below, nose buried in his pulsing ball sack, her tongue teasing his taint as she felt him cumming. Long strokes of her hands on his cock above facilitated in drawing out every last hot splash of cum that rained down on the jock's abs which flexed with every wave of pleasure.

By the end of the deluge his whole chest and body was splattered, with some even reaching up to his chin. The last drooling strings ended up on Lucia's face as Raphael whined at her slowly jacking his still rock hard member. Adding a final bit of whipped cream, the mother began cleaning the jock off, starting with his sensitive head before moving down his shaft, to his v-line, all over his abs and finally his heaving chest. Raphael could feel the cool air hitting his sweet and sticky upper body as he began shifting to lean over Lucia. He wanted his dessert now too.

Reversing their positions so that she was backed against the door, he grabbed the whipped cream can in preparation.

"Wonder how sweet you'll be Lucia," the jock murmured as he moved his free hand. She was blindingly wet and hot under his touch and his mouth watered. Just as his thick fingers began nudging past her panties, a knock at the door startled the couple.

"Hey ma are you done in there yet? Hope Raph isn't giving you too much trouble. I just have some extra stuff to bring in," Leo's voice shouted from the other side. The jock and mother scrambled to get up, Raphael trying to clean off as much cum and cream off himself and Lucia using his shirt.

"Stop shouting at your mother, show some respect!" a masculine voice boomed further outside the storeroom. Leo sighed before shouting back at his father. Lucia shook her head in exasperation.

"Please stop arguing with him, you two are giving me a headache." Mrs. Rossi gestured to the jock when she deemed everything settled. "Raph baby can you please open the door for Leo?"

Leo let out a low whistle as he saw the state of his shirtless teammate, chest shining and sticky.

"Damn what happened here?"

Luckily Raphael's typically slow brain was working overtime today. He gestured to the whipped cream can still in his grip.

"Just a little accident when I was trying to sort through the cans. Thankfully your mom helped me clean up."

"Wow, I try to give ma some more help and you ended up giving her more work man," Leo joked, "let me get you a wet towel to clean yourself a bit."

As Raphael's teammate walked towards the kitchen, Raphael jerked slightly, feeling a hand grab for his phone in his side pocket. Lucia gestured to unlock it. Putting her digits in, the mother leaned in, whispering in the jock's ear.

"We can continue this another time Raph, baby."

Raphael felt his sticky cock, stuffed haphazardly in his tight jeans, almost come back to life. But finally fully sobering up, Raphael looked apologetically at the woman, thinking it was best to call it a night no matter how tempting it was to end up balls deep in pussy.

"Uh, maybe - I don't think that's a good idea. I'll see you next time, I better go back to campus," Raphael blurted out before zooming out the front door, passing by a confused Leo holding a damp towel.

Before falling asleep, the repeated failure of not losing his gay virginity wasn't at the forefront of his mind. Instead, Raphael was only sad he couldn't have his dessert.

***

Francisco was Raphael's fourth closest chance to sleeping with a dude.

Half a year had passed and once again Raphael was swamped by college classes, football matches and surviving life in general. As a side note, if it was up to him, he would ignore the additional time he had spent with the new moms he had been intimate with - totally by accident of course. This gave him no time to complete his quest for a guy to finally fuck him, not for lack of trying. He'd been successful in picking up men from his party escapades but once he got to their off campus abodes, the guy would somehow disappear and his dick would become wrapped in their mom's tight pussy by some miraculous intervention. Raphael attributed his subsequent waning attraction to these dudes as a result of getting his balls drained regularly by these ladies combined with the overarching guilt of doing so.

However Raphael was anything but a quitter. So after analyzing his failures he came up with a brilliant solution. If 'Hot Guy' + 'Living With Family' = '(Accidentally) Fucking His Mom', then all the jock needed to do was find a guy who lives in the dorms, a place far away from family. It would be impossible for a mother to find him.

Using Leo's connections, he wound up with the perfect candidate: Francisco. Boasting a single dorm not in Raphael's own building (he didn't want it to be messy if anything bad happened) and being an interstate student, Raphael was excited to see his hypothesis become reality. Leo's not so subtle comments about what Francisco was packing didn't hurt his case either.

After a small date between them at 'Rossi's' (where Raphael successfully stifled his dick's urge to sneak into the storage room for no reason whatsoever), they planned their next one on the coming weekend. There was a possibility that Francisco had to suddenly be pulled into work on one of those days and though this rang alarm bells in Raphael's head, he still deemed the likelihood of him not getting fucked by a guy to still be fairly low if he had any say in the matter.

Another time-eater to note was Raphael's new position as a T. A. which he miraculously landed after applying on a whim. Raphael had been too distracted by the absurdly good pay rate to properly absorb the course details so he was caught off guard meeting the professor in their office. A stern looking lady flaunting a tight dress that probably broke the staff dress code and judgy eyes sat behind the desk. 'Doctor Florence Parrillo' was etched into a plaque that next caught the jock's eye as he entered. Upon taking the nervous jock's figure in, the professor let out a sigh, removing her spectacles and rubbing her forehead.

"All I asked for was a competent person for once in my life and they gave me a brick wall moonlighting as a student with peas for brains."

Raphael honestly couldn't remember anything after that introduction except how she explained the T. A. requirements like he was five. He'd heard stories of bad professors but he couldn't believe his luck having to work under one for a whole semester. And worse of all, apparently this she-devil was best friends with an influential professor who oversaw Raphael's own department, psychology, so he was essentially locked into this hell.

It was during his first lecture where Professor Florence went off on a student for not completing a pre-reading that she didn't even assign that the jock remembered who she was. Memories of his ex Mark complaining about the bitchy media professor flashed through his mind like a supercut and the jock internally sighed as her rant became directed at him for not putting the pre-reading on the course's online portal in the first place. This became a regular occurrence, no matter how prepared Raphael was for each lecture, the professor would inevitably grill a student and then Raphael for something that was completely her fault.

"Some kind of Florence she is," Raphael thought, collapsing on his bed after a long practice session and an even longer lecture before that. His phone pinging, the jock smiled at the message from Francisco. Only a few more days and he'd be pressed into a mattress by a hot Italian stallion, all his worries forgotten and his virgin ass deflowered. All that stood between him and that dream was one more lecture slot.

Raphael knew that it was going to be worse than usual when Professor Florence was already there even though he had shown up 15 minutes early.

"Finally, you decided to grace me with your presence. Be useful and set up the projector, and put out the handouts. Hurry up, I don't have all day."

There were in fact no handouts assigned for the lecture. So after a sprint down to the library, he arrived back a minute into class with his sweaty dress shirt clinging to his hulking frame just in time for the professor's 5 minute scolding. Afterwards Raphael went on auto-pilot, trying to keep his composure. An hour and 55 more minutes, football practice after and then he was free.

As the usual 10 minutes overtime Professor Florence believed she was privileged to passed, the jock furrowed his eyebrows as he realized she had no signs of closing off the lesson. Her students thought so too so when one of them politely conveyed that the lecture had gone over time, she began biting their head off.

"If you had the brain cells to check your schedules you should know that we have a double lecture slot right now as I have a conference to attend next week."

All eyes landed on Raphael and he could feel the sweat returning to coat his body. He clenched his teeth as he tried to nicely explain himself.

"Professor Florence, I don't believe you had given any warning of an extended lecture slot or a conference in your timetable. Many of us have prior commitments that have not accounted for this change in plans, so could we possibly reschedule this? Or possibly have affected individuals be able to leave early without affecting attendance records?"

Raphael swore he could hear an audible crack as the professor's neck swerved, boring her laser-like gaze straight into the jock like she wanted him dead.

"Such impudence! Is that tight shirt cutting off the blood flow to your brain or are you just plain stupid? I had clearly stated I would be attending a conference at the start of the semester and that should've made it obvious that the preceding lecture slot would be doubled to compensate. Did I not tell you that fact? Are you calling me a liar?"

Breathing deeply through his nostrils, he dulled the fire brewing within, knowing that if he argued back, it would cost him getting his degree.

"My apologies, Professor Florence," the jock spoke through gritted teeth.

The lady smiled in victory.

"That's what I thought. Now, before I was rudely interrupted, let's get back to the reading."

Raphael had to use all his willpower to not stare daggers at the professor, instead putting all his energy into flicking through the presentation under her command. The clock hung mockingly above the room, showing that football practice had ended half an hour ago. Staying back to pack up the room, Raphael gazed at the empty room, jealous of everyone who got to leave before him.

"What are you doing? I don't have all day for you to continue being useless! Take everything from my desk and bring it up to my office in 5 minutes. I need to leave campus promptly and I don't want an air-headed buffoon being the reason I'm late to my appointment."

The shrill voice cut through the jock's attempt at serenity. His patience? Sure. His sanity? Sure. But culling his football time, especially when they had an important game the following week? That was where Raphael drew the line. Now it was personal.

"Maybe if you could ever use your own brain for once you wouldn't be needing to rely on a dumb jock like me. But seeing how I've been the only one not letting this course fall apart, maybe you do need someone actually capable so your life doesn't turn to shit!" Raphael snapped.

"What the hell did you just say!?"

Raphael was sure in her head she was leering over him, ready to make him bend to her unrealistic will. But even in her heels she barely reached his shoulders and he puffed out his muscles to tower over her. Still she didn't seem fazed, poking roughly at his chest.

"You have some nerve to be speaking to me like that young man! I'll have you know my experience could lap your sorry little education five-fold and still have room to spare. You're lucky to even be in my presence!" Professor Florence spat, pushing the jock up against the wall.

Raphael spun them around, bulky arms caging her and he laughed darkly.

"Lucky? Lucky?! This has been a fucking nightmare, trying to bend over backwards to play fetch for a whiny needy bitch of a professor! You should be grovelling on your knees for me with how much I've done for you!"

The heat radiating both of them came at a standstill as Raphael felt something grab at his dress pants. The hand roughly choked the imprint of his rock hard cock, making his knees buckle slightly.

"You think you deserve any respect when you act like a hulk controlled by your primitive instincts? Don't make me laugh!"

The professor let out a yelp as Raphael seized the hand that gripped his erection, pressing it more firmly against him. He was in control now and he was going to make her repay his contributions with interest.

"Yeah, I in fact do deserve it," the jock spat out before unceremoniously pushing her down to her knees. Her face was shoved against his crotch and Raphael's cock weeped precum, anticipating his revenge. "Suck it."

Reality almost pierced Raphael's anger-infested mind as he saw the cold look in her eyes, before he relaxed as a grin took over her face.

"How typical, of course this is all you jocks ever want."

Raphael smirked at the shock plastered on the professor's face who hadn't fully comprehended the size of the tool she was about to be punished by. It eclipsed her, drooling a steady stream as it rested on her face, balls full and ready.

"I guess this is where all your brain mass went to," the professor let out her unknowingly final quip before beginning to slowly stroke the massive member.

With months of experience (sadly not with any guys) under Raphael's belt, her ministrations felt sloppy even compared to the touch of that cheerleader in high school. But the sight of her intimidated by his package kept him rock hard, and he smacked her face a few times for good measure to make sure she knew who was in charge.

Getting bored of the handjob, the jock probed her pouty lips with his leaking cockhead, finally putting that blabbering mouth to good use. The professor could barely fit his swollen glans, struggling to fit any of his shaft that was barely being paid attention to by her hands. After a few minutes of no progress, Raphael sighed, grabbing the back of her head with both big hands and forcefully shoving himself down to the hilt. He moaned at the insane tightness of her throat, the muscles constricting further from the shock of being choked on a thick (sort of) gay cock.

"You're one to preach about being slow. If it'd been up to you it would've taken the whole day to have all of me down your throat, and I have more important places to be."

After grinding his cock to savor the slick cavern he was buried in, Raphael began a rough face-fucking, not giving the professor a moment of reprieve. He clenched his teeth, his cock throbbing each time she choked on him, his smirk growing wider as her eyes wept black with mascara. Though he still had some qualms about being with the fairer sex, he deemed this escapade as something for the greater good. Now he knew that all he needed was his hefty dick to shut her up.

Raphael had barely got onto the road of beginning to flood her throat with his cum when she began banging her fists on his muscular torso, begging him to stop. Though the jock wanted to ignore her, he guessed she needed a break to catch her breath so he withdrew his lengthy mass, a thick rope of saliva and pre-cum connecting her panting mouth and his slick erection.

"What, is it too much for you to handle? Thought someone as tenured as you could handle a simple brute?" the jock teased, pulling her up and pushing her backwards onto the lecturer's table.

Papers and materials that he was tasked to bring back fluttered onto the ground and Raphael shoved his hand up her pencil skirt, eagling in on her drenched pussy before she could make an unappreciated noise. Three thick digits buried themselves into her cunt knuckle-deep and he scraped along her fluttering walls, coaxing out moans that bounced around the lecture hall. But Raphael wasn't doing this for her pleasure - it was just to make it easier for him to sink into her tight cavern and go ham.

Raphael ripped off the skirt followed by her panties to expose her steaming, wet pussy to the outside world. Next he removed her sweater, displaying her sizable breasts trapped in her tight blouse. Giving a rough flick of her clit, making her shriek, he slapped his throbbing dick and drilled straight into her all the way.

"Fuck you're tight. Guess that's one thing I can say I like about you," Raphael said through gritted teeth before he began a brutal pace, long dicking her pussy that bent and pulled to his thrusts.

All the professor could do was become a sponge for a jock who was fuelled by anger and reserved energy from the football practice he had missed. She was just a chorus of moans and squeals as Raphael buried himself deeper, carving himself a place inside.

The grunts of pleasure echoing in the lecture room was cut through by a shrill ringtone. Raphael removed one hand that had been squeezing her waist and pulled out his phone which displayed 'Coach'. Realizing he had only left a quick text updating him about Professor Florence's surprise lecture slot, he accepted the call, pausing his thrusts.

"Raphael Milphio!" a deep voice boomed through the speaker, causing Raphael to recoil away from the phone, "you better have a good excuse as to why you haven't contacted me since that half-assed text telling me you're going to miss out practice today, when you know how important it was!"

Being reminded of the damage Professor Florence had done reignited the jock's anger, so he resumed his onslaught, albeit at a slower pace so he could properly respond.

"I am sorry, coach. You know about the trouble I've been having as a T. A. for this professor. I tried to get out of it but she just wouldn't listen," he gave a sharp thrust on that comment.

"Well son, I know you tried your best but sometimes you just gotta stand your ground and fight for your rights."

Smirking at the now pliable professor below him, skewered on his dick, Raphael replied, "yes sir, I'll try to do that."

"I better hear good news next time this happens then! Now that that's settled, to make up for your absence I am going to arrange a quick session tomorrow to go over plays that the boys and I have discussed to get you up to speed-," a loud squeal from below the jock made the coach pause. "What the hell was that? Sounded like a banshee."

Raphael gave a relatively sharp thrust of his hips before stuffing the professor's mouth with her soaked panties.

"I think my trainers just hit the treadmill badly. Just doing a bit of cardio to siphon out my frustration in missing practice," he replied, trying to silence the woman by removing his other hand to cover her mouth.

The coach chuckled through the speaker.

"You think you're smart mister? I've had to deal enough with Levi's 'cardio' excuses when he's sneaking off with his boyfriend. Well, I'd give a spiel to wrap it before you tap it but I don't have to worry about you getting someone pregnant. Just don't go too crazy tonight - remember, I want you in my office at 8am sharp tomorrow morning!"

"No worries coach. I'll make sure to pull out everything about being safe and what not. See you tomorrow."

"Your ass better be there," Raphael's coach quipped back, "and Raph? This better not become a regular thing for you. I already have to deal with Leo and Levi sex antics. Take care." His coach hung up.

The jock then suddenly stopped, buried deep within the professor. He had unwittingly been able to keep her teetering on the edge of an orgasm as she slowly came back to her senses.

"Now where we were?"

Raphael resumed with a much slower fucking. Both of them felt the intense stretch as the jock dragged his elongated cock through her channel, reveling in the slick, wet pleasure that bloomed between them. It was almost more overwhelming than his brutal onslaught earlier and Professor Florence's nails dug into the mahogany table, trying to steady herself against the jock's thick tool.

"Not feeling good? Guess I'm not up to your standards," Raphael teased, giving an excessively slow drag of his hips out of her canal.

The professor grit her teeth, barely able to get her words out.

"Such audacity," she gasped as he brushed against her g-spot, " just make me cum and get this over with!"

"Mmhm. But why should I? What have you done to deserve it?"

"I've given you the chance to actually do something worthwhile in your life! You should feel honoured to be working under such a prestigious person like me!" Professor Florence ranted, her shock briefly making her forget about the massive protrusion inside of her.

Raphael's jaw ticked and he thrust roughly into her to shut her up.

"You think you actually gave me anything worthwhile? I've had to drive myself mad trying to cater to all your fucking whims just so I'm not blacklisted. And just to be clear," he loomed over her, staring into her equally fiery eyes, "it seems that you are working under me right now."

Showing her the brute she wanted him to be, he grabbed her blouse with both meaty hands, ripping it open as buttons flew around the room. He pinched a nipple making her let out a sharp shriek, using his other hand to grope her other full breast.

"How about this? I cut you a little deal? I just have a few demands to make this experience better. For me. For the students. And...," Raphael smirked as he trailed off, "well just me and the students."

"You think I'm going to cater to your silly whims, please," the professor spat back.

"Oh well, guess we're gonna be here all day."

The jock picked up the pace marginally, just enough to make her gasp. But he made sure to ignore the pleasure button inside of her, and such that the friction of his movements couldn't bring her any closer to the end. Five minutes of his teasing passed before Professor Florence took a deep breath, flushed with sweat.

"Fine you win! What do you want?"

Raphael nestled his dick so his cockhead was gently pressing against her g-spot, unmoving. Leaning over, he steadied himself over her with both arms caging her in.

"Number 1: I am not your scapegoat or your errand boy. I will only do what my contract states which only involves assisting you within class hours."

The professor let out a humph and narrowed her eyes at him, crossing her arms across her bountiful chest, gesturing to him to continue.

"Number 2: I want you to treat your students and me with actual respect. Stop looking down on us because you think your eight degrees or whatever make you a better person."

Raphael ceased her gawking by firmly grinding again, kissing her cervix.

"And finally Number 3: You can start doing Number 2 by formally apologizing to your students and me in regards to your antagonistic behavior and own up to your mistakes."

Professor Florence would've sat up if she wasn't pinned down by Raphael's cock.

"Like hell I will!"

Sighing, the jock abruptly removed his tool from her cunt, shaking his head and saying "well I guess you're not gonna get what you wanted."

He began stroking his pussy juice covered dick, the professor completely hypnotized by the weapon that was just inside her. Squeezing her legs together to stave off the emptiness in her throbbing core, she reached out to take a firm hold of him, pulling him back.

"Fine you win. Just make me cum!"

Raphael grinned as he went balls deep, the loud smack of their union drowning out her squeal of delight. He began a rapid tempo even though the professor was so close, needing to finish releasing his anger at this woman. Grabbing her breasts as leverage, Raphael thrust faster and deeper into her and roughly pinched her nipples causing her to let out a string of moans.

"And one last thing. Don't be such a fucking bitch!"

Professor Florence's orgasm went off like a fire alarm in the middle of the night - loud, sudden and intense. Raphael clenched his teeth feeling her vaginal walls vibrating like crazy and felt his simmering balls covered in her pussy cream and juices. Feeling his time was near, he withdrew his throbbing cock and moaned whilst he sprayed her body with his semen. It splattered all over her exposed body, some even landing on the papers that hadn't managed to become pushed onto the floor by their fucking.

Collecting the last squirt of cum from his cockhead and flicking it onto her stomach, Raphael looked over at his work of art. She was finally speechless, twitching and unable to move as the waves of her orgasm continued to still wash over her.

"If you even think about going back on your word, I won't be so nice next time."

The jock removed his sweat soaked button up and threw it on top of the professor. Grabbing a jersey from his bag he shrugged it on.

"Don't have anything else to say? How peculiar. Well, I've got places to be now so you better clean up this mess. And I would say have fun at your conference but I really couldn't care less. Bye now."

A few days passed and Raphael was riding the high of putting the professor in her place, feeling accomplished reading over her apology on the course forums and channeling that energy into perfecting himself for the game next week. He was giddy sitting in Francisco's dorm room, asshole prepped and dick locked and loaded. The next five minutes felt like an eternity as he waited for Francisco to return before he mindlessly began looking around.

That's when his eyes locked onto the ID card on the desk.

'Francisco Parrillo'.

"Well that could just be a popular last name."

But that's when his eyes shifted over to a photo frame, showing Francisco with his family, artificial smiles captured in a sterile photography op. He could barely hear the door open as his prospective lover returned.

"Hey sorry for making you wait I-"

"Your mom is that fucking bitch of a professor?!"

***

It turns out that cursing out someone's mother isn't conducive in making someone like you, let alone want to take your virginity.

There was barely time to begin an argument before Raphael was tossed out like a sack of potatoes, where he almost got hard at the strength Francisco had to manhandle the footballer player.

Nonetheless, Raphael felt like it was finally time to throw in the towel.

Over the next few weeks, football and his previous MILFs were his outlets as he exhausted the anger he held towards his situation. But once that was used up, he finally showed signs of losing his touch, at least in football, where he almost fumbled an important throw causing his team to barely make it to the finals.

Going to bed after a long session of being consoled by Ivan's mother's tight pussy, Levi found him in the gym the next day, overexerting himself as he unwittingly set a new bench press P. R.. The team captain gently eased the weight out of Raphael's hands, gesturing him to sit up as he took a spot next to him on the bench.

"Okay Raph what has been up with you lately? Your body honestly looks the best it's been but your whole vibe and performance has been tanking. You know I'm always here if you wanna talk about it."

Raphael was silent for a moment before he wiped the sweat off his brow, putting his head in his hands.

"I'm a virgin, and I somehow can't change that."

"Huh, how is that possible?" Levi looked incredulously over at his teammate, "I literally heard you fucking someone on campus like a month ago."

Raphael was now the one to be gobsmacked.

"What?!"

"Yeah, Leo and I were walking through the media building after practice to see if we could catch you. We know how you sound when grunting so when we passed by Room 3-A we knew it was you. And whoever twink you had in there sounded like they were dying from pleasure," Raphael reciprocated an offered fist bump, "very impressive man. So what do you mean you're still a virgin?"

Raphael flushed at the compliment but twiddled his thumbs, trying to properly word the events that unfolded that day.

Levi once again wore a flabbergasted look on his face as Raphael summarized his copulation with the media professor as PG as he could.

"Damn, you are wilder than I give you credit for dude. Fuck. Well, you better not become a second Leo because I don't think coach and I could handle that," Levi chuckled before taking on a gentler lilt, "so I assume your plight is to find a guy to sleep with?"

Raphael nodded solemnly.

"I've been trying so hard since starting college and the closest I've gotten was kissing."

"Well if it makes you feel any better, if I wasn't with Andre, I'd totally give you the best first time you could imagine."

Levi's blue eyes lit up like sapphires as an idea bloomed under his curly mess of blond hair.

"Wait, I think Andre might know someone. If I remember correctly they're a sophomore like you and new to the swimming team. Andre was saying that guy was having trouble finding a boyfriend."

The team captain laughed and slapped Raphael's back in joy.

"Oh my god it's like destiny dude! I'm going to get you out of your funk if it's the last thing I do."

Raphael smiled politely at his friend, the golden retriever bouncing next to him almost making him hopeful as well.

The following day, Raphael woke up to a text message from Levi's boyfriend. It was an invite to an upcoming swim meet.

"Well, it couldn't hurt to check it out," Raphael thought.

And Raphael was so glad he did.

Running a bit late after escaping the clutches of Professor Florence's pussy, he made it just in time for the butterfly heat. The participants were already in, slicing through the water and Raphael zoomed in on the swimmer wearing their college's orange and blue swim cap. He was leagues ahead of the others, strong arms and broad shoulders propelling him forward towards an easy finish. Then they got out of the water.

Raphael felt like staring at the man was sacrilegious because he was literally a god. Toned muscles carved out of the glossiest bronze mankind could source, a stunning face paired with plump, kissable lips and a head of raven black hair that sparkled majestically under the water spray. And his eyes, god - they were a piercing green that Raphael couldn't avert his eyes from. When they stared into the jock's own brown ones several yards away, it felt like time stood still, the swimmer letting out a wink before exiting the pool.

Yep, he was definitely still attracted to men.

The jock's mouth was watering as he took in each of the guy's eight stone-cut abs, not noticing that the chiselled figure was getting closer.

"Yo Raph, you there?"

"Huh? What?" Raphael said groggily, finally taking in that Levi and his boyfriend were standing in front of him, joined by the god from earlier.

"Here's the guy I've been telling you about," Levi gestured to the man.

Up close, Raphael could see the prominent bulge trapped in those skin-tight swimming trunks. He licked his lips before a deep gravelly voice forced him to stare up into emerald eyes.

"Hey, I'm Donatello, but you can call me Don. You must be Raphael?."

The football jock felt like he was melting as the swimmer flashed him a smile.

"Uh yeah, I'm Raphael - but you can call me Raph," he let out a choked laugh, feeling his face flush.

"Well," Levi's boyfriend clapped his hands together, "you two lovebirds have fun. See ya later."

Raphael barely noticed the pair running away, completely enraptured by how Donatello's muscular chest moved with every breath.

"So whaddya say we get out of here?"

All Raphael could do was nod as he was whisked away.

***

Raphael woke up to the summer sun on his bare skin, the morning hour dulling its harshness to a pleasant warmth. He was pleasantly sore and squished in the embrace of Donatello's slightly taller frame, their lithe but sturdy arms holding him tight.

The jock had finally done it.

Last night was a passionate blur of smooth muscle, roaming hands and gasps of pleasure - a memory that made Raphael giddy inside. He felt like he had reached heaven as his boyfriend stretched him wide open, how the pain blurred into exquisite rapture and how the sight of the swimmer pummelling him into the mattress was burnt into his mind forever. The open window had mostly relieved the room of the smell of sex, sweat and cum but Raphael could still find traces of their lovemaking as he buried his face into Donatello's muscular chest.

Raphael smiled at how much of a deep sleeper his boyfriend was. Gently getting out of bed and slipping on his boxers, he made his way out of Donatello's bedroom to quickly use the bathroom.

The jock let out a yelp as he spotted Mrs. Romano seated at the kitchen table eating breakfast, her eyes locked onto him.

Of course, Raphael had taken precautions with dealing with Donatello's mother (and all MILFs in general). After their first date post-swim meet, Raphael had messaged each of the women he had been fucking to finally put an end to the madness his dick was proliferating. He ignored their dismay, choosing instead to be lost in Donatello's dreamy eyes.

Donatello had recently moved to town with only his mom, as his dad was a foreign diplomat stationed overseas. Though this was a glaring red flag, Raphael felt experienced enough to overcome it, knowing that Donatello was worth it. The universe had made Mrs. Romano almost as beautiful as her son, a model-like face paired with a fit body and curves for days. Her personality seemed to also be perfectly crafted to make the jock fall back in old patterns - a balance of sweetness, assertiveness and sexual frivolity that honestly scared him.

This was showcased just a few days earlier. Raphael had been avoiding the bedroom eyes Mrs. Romano had been sending him since they had been introduced after Raphael and Donatello's first date but there wasn't any room to escape as he sat with her in the living room. A mundane show was playing as the football player waited for his boyfriend to finish class.

Mrs. Romano was wearing only an almost see-through white blouse that reached her knees, covering what Raphael believed was lingerie. As their air conditioner had been out of commission for the first few weeks, she used the heat to excuse her outfit. Raphael also felt hot, initially glad that he had opted for a tank top and basketball shorts but now he felt like a piece of meat, the older woman drinking in his strong arms and thick thighs on full display.

Raphael tried to will his erection down, his gaze locked onto the television instead of at the skimpily dressed mom sitting on the other end of the couch. His gaze almost wavered as a daring smooth leg travelled down to rest on his thigh. Pushing it away had only worked a few times before Mrs. Romano had firmly planted her foot so it was almost between his legs.

The past almost two years of knowing the sweet touch of older women had almost crumbled the jock's resolve, his erection trapped in his pants desperately pointing towards Mrs. Romano like a divining rod to water. But he was ready for this challenge. Ignoring how hard his dick was, Raphael finally looked over at the mother, gently removing her leg and looked at her sternly.

"Mrs. Romano. While I appreciate that a beautiful woman like you is interested in me, I'm afraid I can't do this. I am very interested in your son and would like to not mess it up by doing anything with his mom."

Mrs. Romano looked at him, surprised by his eloquent rebuff.

"I wanted to have a taste before anything serious happened but I guess it is too late for that," the mom replied, getting up to head to the kitchen. "Well, if you ever change your mind you know where to find me."

So after calming his beating heart after getting jumpscared by the woman, he gave her a quaint smile, glad he wasn't naked at least.

"Good morning Mrs. Romano. I thought you were flying out this weekend?"

"Please Raphael, I told you to call me Val - Mrs. Romano makes me feel old. I messaged Don that my flight was postponed due to strong winds but judging by the state of you I think he was too busy to check his phone."

Raphael looked down at himself, noticing the love bites dotted across his upper body. He was sure there were even more on his back and legs.

"Yeah he sure was preoccupied. I'll leave you to your meal now, I need to use the toilet and Donnie might be wondering where I went."

Mrs. Romano did a final appraisal of the hunk before waving him off.

Days turned into weeks until the school year neared its end. Summer had slipped away leaving Raphael and Donatello to continue their honeymoon in the incoming chill of fall. The football player's book of gay sex was now bursting at the seams, exploring everything he could with his boyfriend until they both collapsed on Donatello's bed, grinning and exhausted.

Mrs. Romano was also giving the jock less flirty looks, beginning to expand her fashion startup in their garage. However this meant that his boyfriend had been enlisted in helping his mother deal with shipments and other heavy lifting, reducing the time they spent together. Thankfully, it was a busy time for Raphael so he could spend the extra time preparing for exam season and the final play-offs.

It was an unconventionally warm day when Professor Florence had ended her class early which should've been a bad omen in retrospect. Raphael, feeling lucky, decided to head over to his boyfriend's home, wanting to surprise him after not meeting up for a few days. With several shipments clogging up the garage, Donatello had apologized, wanting to help his mother clear it out so she could quickly resume her business.

"Maybe I can even lend a hand," the jock thought merrily, parking outside the Romano home.

The doorbell was still broken since his last visit a week ago so Raphael knocked. No one answered. Moving to the garage door, he could hear the soft hum of music so one of them should still be inside.

It was a clipped shout that snapped his attention. Raphael curiously headed to the sidegate where the sounds got louder. The crude noises finally registered in his head.

"Mrs. Romano's probably getting fucked in the backyard," his mind supplied, flushing at the string of moans that echoed. "Donnie's probably somewhere else," he assumed.

All Raphael had to do was turn around, get in his car and call his boyfriend - obviously opening the sidegate, slipping around the side of the home to get a peek at the hot mom getting bred by an equally hot stud was not the play. His phone still deep in his pocket, Raphael was a ninja as he stopped before the corner of the house, just a few seconds away from giving his dick some new spank material.

What the jock didn't expect was to instantly see the rosy face of Mrs. Romano, ducking his head back behind the wall. Peeking out again, he thanked the gods that she was in a state of bliss, eyes firmly shut as whoever was below her was doing a number on her. Her unknown partner was fully hidden by the lawn chair from Raphael's perspective, but the sight of Mrs. Romano grinding front and back was enough for his dick to start chubbing up.

Lost in the erotic sight, Raphael really should've known he was in no position to be a voyeur as Mrs. Romano made eye contact with him, having direct line of sight. He was about to slink away when he noticed the smirk on her face.

"Oh yes, keep eating this pussy. You always do it so fucking well," she purred out, putting on a show for the jock by grinding harder onto the talented mouth of the person underneath her.

Only the traces of a deep, masculine lilt could be determined with the person's moans being muffled by her cunt. But all Raphael needed was the look on Mrs. Romano's face as she reached her climax. Raphael could hear the sloppy sounds of licking and swallowing as her lover eagerly drank up all her juices, causing the mom to shout more expletives as she rode out her orgasm.

Before Raphael could even move his hand to relieve the pressure in his shorts, he froze as the unknown partner sat up. He was tall, seeing how his broad shoulders, neck and head easily rose above the back of the chair, a mop of sexy black hair completing the look. The jock was flabbergasted as he watched Mrs. Romano thread her fingers greedily though those luscious locks, just as Raphael had done many times before.

"Remember Val, this is the last. Got it?" Donatello's voice rang out sternly.

"Just shut up and fuck me already - you already know the drill."

They both let out a loud moan as Raphael watched them complete their union. He absorbed how his boyfriend's back muscles flexed as his big hands held steady on their mother's hips, driving his thick, long cock in and out of her. Mrs. Romano let out another pornstar moan, continuing to stare straight at the football player.

"So what if I spilled the beans to your little Raphael - that his boyfriend has been a bad boy, gladly giving his mother his big cock over the last three years?"

Raphael could feel the increase in intensity as his boyfriend took a rougher approach to his fucking.

"Stop saying it like that Val - though neither mom nor step-mom really suit you since you've been nothing but a slut since you and dad met," his boyfriend replied, grunting in exertion, "and you wouldn't even think about blackmailing me. You love me and my dick too much."

"Well, I'll start loving you less if you don't make cum in the next five minutes!" Mrs. Romano retorted, grabbing the head of the chair for stability.

Raphael's mind was overwhelmed, not quite comprehending either the lore drop or the erotic scene present. His dick on the other hand was having a great time, trying to break out of his shorts in a precummy mess. A loud groan from his boyfriend signalled the end was near.

"This is the last load you'll ever get, so you better fucking cum with me right now! Fuckkk!"

The chair creaked dangerously as the swimmer thrust up into his mom for the final time, surely flooding her insides with their thick, delicious cum. Raphael watched as Mrs. Romano came down from her high, slumping against her son's sturdy chest, moaning softly as he languidly sucked and played with her breasts. He didn't know how much time passed before the pair got up, letting Raphael see them in all their naked, sweaty glory.

Raphael could also clearly see the shock that imprinted on his boyfriend's face as he did a double take at their boyfriend. They began flailing around, muscular arms not knowing whether to cover himself, his mom or both of them. It took a moment for him to find his words as he took a tentative step towards Raphael.

"Raphie, I uh can explain," Donatello started, "how much of that did you see?"

The football player moved out of his hiding spot, now standing a few feet away from his boyfriend.

"Just the part where you guys started fucking. Unless you were fucking her before that, then it was after you were eating her out - so like fifteen minutes ago-ish?" Raphael continued rambling, "I finished the lecture with professor hell on Earth so I wanted to surprise you. But I guess I was the one surprised instead." The football player moved to a lounge chair they hadn't been having sex on, "so you wanna tell me why you were fucking your mom?"

They both heard the squeak of the backyard door, watching Mrs. Romano hover at the entryway.

"I'll leave you boys to talk it out," she said before shutting it.

Looking back, his boyfriend instinctively tried to sit next to him but realising his state of undress, decided to continue standing naked (as Raphael would find out later that their clothes were haphazardly strewn somewhere in the garage). Donatello took a breath.

"So. Where do I begin? I think Val has some idea but this is something I haven't told anyone." Raphael watched his boyfriend take a deep breath before starting. "I know I like guys, it's something I've known since I was young. But - fuck!," he ran a hand through his sweaty hair, "this is going to sound crazy but please listen."

Raphael began listening to a familiar tale. It had started off with Val. Then that one time event turned into a pattern as Donatello had become attracted to his boyfriend's moms. The football player remembered how he was surprised Donatello hadn't been able to keep a boyfriend, chalking it up to bad luck (which he was correct about).

"And then I met you. We've talked about how meeting each other felt like fate. I cut off all communication with the moms from back where I used to live once we started dating. But today - today was going to be the final time with Val I swear."

Donatello took one of Raphael's hands in his, lowering his forehead onto them.

"I know my story's all kinds of fucked up. But I really like you," Donatello whispered, "please forgive me."

His boyfriend, with his head down, didn't notice the water pooling in the football player's eyes as he fully absorbed the situation. Lifting Donatello's head up, he cradled his also teary boyfriend's face in both hands, staring into their magnetic green eyes.

"Donnie. I'm gonna say something that sounds even crazier so just listen."

Raphael began a recount of his own sexual adventures, of his ups and downs with prospective partners and his sudden attraction and endeavours for their mothers as well. Donatello sat there gobsmacked before bursting into teary laughter at how absurd their situation was. Raphael joined in as they shared their stories, both of them thinking it really was destiny that brought them together.

"The universe really fucking hates us - or loves us. I can't really tell," the swimmer exclaimed, wiping a tear from under Raphael's eyes.

"Yeah. But I'm really glad it let me meet you."

Raphael felt like he was melting once again as his boyfriend shot him the brightest smile.

"Me too."

It was then Raphael noticed that his boyfriend, who was still fully naked, was hard, probably as a consequence of the sex stories that they just shared. When the football jock grasped it cheekily, surprise overtook him as Donatello shoved a hand into his shorts to also grab his cock, which was equally as hard. The swimmer smirked as a lightbulb appeared above their head.

"You wanna go stuff our dicks in Val's pussy together?"

A firm grip on his boyfriend's dick, Raphael pulled them towards him.

"Fuck yeah."

***

-EPILOGUE-

Raphael was tucking his freshly sucked cock into his dress pants when he looked towards the door to the lecture room. Professor Florence exchanged an unpleasant smile with Donatello as they passed each other, his boyfriend strutting up to him to place a passionate smooch on his lips.

"Hey Raphie. She didn't give you too much trouble again right?"

"Not at all, she knows she has to be on her best behavior if she wants a reward. So, you think you're still up for tonight?"

The swimmer rolled his eyes at the friendly jab.

"Well Raphie, I'll have you know I survived Mr. and Mrs. Rossi, thank you very much," Donatello retorted but began rubbing his wrists, "though I need you to rub some cream for the rope burn."

Raphael lifted their wrists, leaving a kiss on each one. "Of course Donnie. I'll let Val know then?"

"Go for it." Donatello took his boyfriend's hand in his. "Let's get going then, shall we?"

Raphael squeezed it tightly.

"Lead the way."