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I was fresh off of my breakup with Mandy.
We had dated for a long time. Four years and some change actually. Pretty much all through high school and the first year of college. We had a lot of firsts with each other and maybe we were in love, but in my horny college mind all I wanted to do was to try my luck at chasing hot sorority girl tail.
It probably would have been smarter to stick it out. Mandy had been game for just about anything in bed. I was still pretty vanilla, but I had a few kinks that she helped me discover. She was willing to give anything a shot at least once and if I clicked with something she would dive head first into it. It's actually how I discovered I was into pee desperation. Well, she figured it out and nurtured my curiosity into a full blown kink. It's a story for another time, but she loved having that sort of power over me. She was willing to explore anything if it meant getting me off. Truthfully I had it pretty good even if she wasn't classically "hot." Her body was alright if just a touch on the unathletic side, but she was pretty nerdy and had no interest in putting much effort into her appearance. In my hormone addled college brain, every other girl at my school was a complete smoke show and I didn't see any reason I couldn't "trade up." I wanted the best of both worlds - a girl who was just as happy to explore my kinks, who also happened to look like she stepped directly out of the pages of sorority girls gone wild.
That made it a pretty messy breakup; as messy as one would expect anyway for two 19 year olds that were "in love" and had not known anything different than being together since before we could even drive. Not only did Mandy not take it well, it became immediately apparent that my expectations for success were wildly overinflated. The first few days were hard, for sure. I went from consistently having someone to "take care" of my urges almost daily to having to do that all on my own again.
I think what made it even worse was that following the breakup I had some unrealistic expectations on how easy the dating scene would be. I guess I had just thought it would be as simple as sneaking into a frat party, grabbing some tiny blonde by the waist and expecting her to be happy to mount my dick. I had it all laid out in my head that I could break up with her on Tuesday, spend my day Wednesday "adjusting" to the new reality and by Thursday I would be ready to go find a girl to at the very least give me a quick tug. I mean, why wouldn't it work that way? I had spent the last four years able to just gesture to my crotch and have my balls drained by an eager to please wet hole (or a friendly hand, in a pinch!)
Reality was a little more brutal than my expectations. I wasn't a member of a frat, so even getting into a frat party wasn't as straightforward as I had thought and even if I had my "game" was pretty rusty. I was in total denial that first weekend. Thursday passed me by and ended with me laying in my dorm staring at the ceiling willing my expectant dick to just go to sleep. I guess I was holding out hope that I would get things figured out before it finally just exploded out of frustration. By Friday I was so wound up that I considered calling Mandy, just to see if she'd give me a quick "service," but I knew that would lead to all sorts of complications. Saturday night I went so far as to write out a long winded text inviting her over. I'm sure she would have been game, but I managed to resist the urge to send it before going to sleep. Sunday morning I woke up to sticky sheets after a particularly vivid dream.
It was one of those dreams that felt so real i wasn't fully sure whether it had actually happened. Mandy was in my dorm room bed with me, straddling me fully clothed as she had so many times before. It was all too familiar of a scenario for us. We had convinced each other that we were going to save ourselves for marriage and never really felt the need to test the boundaries of what was acceptable, but on the night of my 18th birthday we found ourselves alone in my bedroom making out. One thing led to another and it ended with her straddling me, grinding into me like a cat in heat. I had been so worried that my parents were going to walk in, but what could they really have done? With me turning 18 we were both officially adults so aside from a little familial embarrassment there was nothing particularly wrong with what we were doing. Besides, had they walked in it probably wouldnt have looked like much more than a heated make out session.
I don't know if she actually got off from it or not but I certainly did. It was particularly awkward that first time since we didn't talk it out beforehand or anything and I certainly wasn't about to tap her on the leg and warn her "stop it or I'll cum in my pants," but after a few sessions it had just become the norm for us and there was no hiding the evidence. She knew exactly what she was doing to me. She had wiggled on top of me many times, feeling my hips grind into her with increasing intensity until a wet spot bloomed on the front of whatever I was wearing. It had become so commonplace that I didn't even get embarrassed about her seeing me cum in my pants anymore. It was just what we did to get some relief.
For the intervening months between that night and when we would eventually have sex, that's how all of our make out sessions seemed to end. That was probably why I was able to relax in the dream and just let it happen.
There were definitely things that were out of place in my dream. It felt like a flashback, but it was certainly the current version of us - I definitely had put on my freshman 15, and Mandy had that Pokémon tattoo on the top of her thigh that she had gotten the summer after our freshman year. Somewhere in the back of my mind i knew we had broken up, but stilll I was a bit confused as to why we were dry humping instead of just fucking. The grinding motion of her too-tight denim shorts pushing along the outline of my shaft under my gym shorts had me hypnotized, but it weirdly lacked the necessary pressure to get me off.
My frustration was overwhelming. The seam of her jeans shorts vividly cut between her lips and I could clearly see the outline of her cameltoe grinding into my lap but no matter how much I thrusted my hips into her I couldn't feel it. I craved that pressure. I needed it.
After what seemed like an eternity, dream Mandy seemed to take pity on me and shifted down to coo and whimper in my ear, mimicking the sounds she would make any time she was trying to make me cum and we didn't have time to spare.
Once we had eventually started having sex, we had gotten pretty open with each other regarding our needs. If I ever needed release all I had to do was ask her and she would dutifully get me off immediately. It was like having a best friend that I had no boundaries with and understood my every need. She knew my fetishes. She knew my triggers. She had been completely in tune with my body.
"I want you to cum for me now, baby." Her voice was hot and soft in my ear. It was like a recording of her exact words she had whispered to me on our last beach trip over the summer. She had been teasing me the entire drive, spreading her legs in the passenger seat and lightly playing with herself. She pointed out to me a small wet spot she had coaxed out into her bikini bottoms, and had begun complaining about how desperately she needed to pee. I knew she was playing it up and performing for me but by the time we had parked I had been so rock hard I had no chance of walking to the beach without everyone being able to see the tent I had pitched in my thin swim trunks. Instead she took me in her hands, our car the only thing blocking the view of her handjob from oncoming traffic. "I want you to cum for me now baby. That's it, just let it all out." She had whispered encouragement in my ear as she pumped out my load all over the sidewalk.
Back in my dorm room bed I obeyed the memory of her voice.
My orgasm rocked through my body so hard that it woke me up. My hips thrust repeatedly upwards ineffectually into my thin sheets trying to find the rapidly fading image of Mandy's body, but was only met with the resistance of my waistband the tip of my dick had managed to tuck into. Groggily I got my hand to my shaft just in time to feel myself begin to involuntarily pump cum out onto my belly and sheets, but I was too late to prevent the mess.
"You alright dude?" I heard Mike, my room mate call from the bottom bunk at my violent shaking of the bed.
I came to sticky and guilt ridden with my cheeks burning with embarrassment in a puddle of my shame questioning whether I had made the right choice in breaking up with her after all. As I sat on the dryer later that day waiting for my sheets to be done though, I finally admitted to myself that I was going to need to start regularly jacking off if I didn't want to spend my entire sophomore year doing laundry.
It was pretty awkward for me at first. I hadn't gotten myself off in well over a year and a half - basically not since high school, and even then it had been pretty rare on account of Mandy's assistance. I decided I needed to do it once a day to prevent any more "accidents," but it took me a while to really get a rhythm down. The first few times I didn't even use porn, I just waited for my room mate to be out of the room and opened up my photo reel on my phone and shamefully whacked it to the pictures I had taken of her on the beach. She had told me at the time between poses that they'd come in handy if she ever wasn't available, but at the time the thought of ever using them was laughable. Why would I settle for a picture of her with her hand down her bikini when she could get me off while I watched the real thing? The shame of using them as wank material was pretty overwhelming. It was like I was first discovering masturbation again.
I think it affected my outlook on life a bit. The first month I had just chalked up to post breakup blues, but after a particularly weak moment where I nearly texted her again to tell her I couldn't her out of my mind I deleted the photos off of my phone and started using porn like a normal person. The second month had me questioning if I had made the right choice at all, and by the third month I had to admit to myself that I was in the middle of a terrible dry spell that had no end in sight. More than once I kicked myself for deleting all those photos. Mandy may not have been the hottest girl at our university by a long shot, but those photos were for me, and she knew the exact poses that would wind me up. Nothing else seemed to "scratch the itch" quite as well.
I think what made it worse was that Mandy had started dating somebody new relatively quickly after we broke up. Not immediately, but like a month later. I had so many nights to sit and stew over the idea that she was still getting laid and all I had was my hand to keep me company.
Things were pretty grim before I met Jordan.
I had a light at the end of tunnel: my room mate Mike was turning 21, and we had a plan to sneak me into one of the bars. The Toasty Oat, a bar just down the street from our dorm had an outdoor seating area and we had heard through the rumor mill that the bouncers never really watched it. It was fenced off but Mike and I looked similar enough that we figured he could go in, wait a few minutes, pass his license out to me and then I could use his real license as a fake to get in.
It wasn't a flawless plan, but the prospect of hitting on drunk girls instead of sober girls made it significantly more appealing than anything I had been trying previously. After all, the few times I had hit on sober girls in class, they seemed to be able to sense my growing desperation and it was clearly a turnoff.
We couldn't do it the night Mike turned 21, that would be way too obvious for the bouncer to see two similar looking guys walk into the bar exactly on their 21st birthday, so we waited about a month. It gave Mike some time to scout the place, but it also meant that I was a solid 6 months in to my dry spell by that point.
We picked a Thursday night because that was the night that seemingly the entire campus went out to drink. Phase one went off without a hitch. Mike went in first, ordered a drink, waited twenty minutes then met me out in the seating area. He slipped me his ID through the vines that twisted along the high metal rods separating the seating area from the back alley. My heart was in my throat when I handed the bouncer "my" ID but I had a stroke of luck as while he was looking at the picture, someone else was making a scene while being escorted out the front of the bar for being too rowdy. He threw the ID back at me and rushed to help his coworker. I took my opportunity and slipped in the front door.
I felt like a kid in a candy store. I had never seen so many people drinking in one place. There were pockets of girls and guys circled up talking loudly at each other over the noise of a live band playing 80s covers.
Mike tapped me on the shoulder and shouted "beautiful right?" And held up his beer. I had to agree.
"Yeah, but how do I get one of those?" I asked, pointing at his beer.
He proceeded to walk me over to the bar and flagged down the bartender. He ordered two Kiltlifters and told the bartender to put it on my tab as "payment." I handed the bartender my cash. He paused for a second as if paying cash was weird. For a brief moment I thought everything was going to fall apart right there, but he took the cash anyway and brought me back my change and two beers.
After a couple of rounds, Mike yelled over the loud music playing behind us, "Hey chill here for a minute! I gotta go hit the restroom." He finished his bottle, left the empty and disappeared into the crowd.
His place was almost immediately filled by a girl who had been waiting for an open spot at the bar to get the attention of the bartender. I brought my bottle to my lips and took the opportunity to check her out. After the mentally taxing dry spell of my own causing I had been living through my standards were pretty low, but she was the exact sort of girl that I had voluntarily put myself in this position for.
I know that I probably gave up a good thing with Mandy for pretty shallow reasons, but this girl was all of those shallow reasons personified. Where Mandy was a little gangly, this girl was petite. Mandy's face wasn't classically beautiful, this girl's was. While Mandy rarely ever wore anything particularly form fitting, this girl was dressed to club in a pink and blue tank that accentuated her small tits and a tight denim skirt. It was hard to imagine Mandy in anything that tight or revealing - the closest she had ever gotten were her denim shorts, and she never wore those out. It was always pretty clear that she had worn those just for me.
Honestly, I just figured this girl was out of my league.
She was shorter than me by a few inches and had to go up on her tiptoes to lean over the bar to grab the bartender's attention. I was trying not to stare too obviously, but the way she was bent over the bar was making her short denim skirt ride up. I was in the middle of mentally willing it to hike up just an inch higher when I realized I was busted.
"See anything you like?" She scolded me while looking back over her shoulder and tucking a strand of her short blonde hair behind her ear. She returned her heels to the ground with a "clump" and crossed her arms across her chest. She squared up with me jutting one hip out the side, putting out significantly more attitude than I thought could radiate out of such a small frame.
"Uh I was..." but I couldn't think of anything clever to get myself out of trouble.
"... just about to buy me my drink." She finished my sentence. It wasn't a question. She knew I got an eyeful and she was going to make me pay for it. I still didn't think that I had any chance with her, I just wanted to avoid a scene.
"Yeah exactly that." I agreed. Worst case, I figured, is that she might stick around and give me a chance to get used to actually being given the time of day by an attractive girl.
"Hey don't I know you?" She finally asked after an awkward pause. I was doing my best to not let my eyes drift down to her chest. I was thankful for the distraction. I was doing my best to avoid staring down her top. Not that I was creeping out or anything, she was just so short that her cleavage was right in my eye line. I knew better, but it felt like she was pushing them up and together on purpose to get me to look.
"I don't think so?" I replied while turning back to the bartender to pay as he brought her some pink mixed drink, grateful to have a momentary distraction from her cleavage.
"No. I definitely know you!" She exclaimed forcefully. "Humanities 172, 9:00AM on Mondays, Wednesdays and Fridays!"
She wasn't wrong I was definitely in that class, but I didn't recognize her at all.
"Oh yeah, I'm in that." I replied, racking my brain to try to conjure up any memory where we may have interacted. It was a big lecture hall though, I don't think I could be faulted for not seeing her in there. I couldn't really be faulted for that though; all of the gen-ed classes were packed full of hot girls. It was what got me in this situation in the first place. I'm certain that I would have remembered if we had ever talked though.
Still, she looked somewhat offended. "You don't remember me at all!" Her mouth dropped open in mock amazement while playfully slapping my arm.
"Sorry?" I half-asked. "Should I?"
"Oh you definitely should." She teased while taking a sip of her drink and making very deliberate eye contact over her straw. There was some meaning that I couldn't quite get behind her bright green eyes, but her almost imperceptible eyebrow raise made me realize there was something I wasn't getting that she wanted me to. I couldn't believe how easy this was though. Thirty minutes in a bar and I already had a girl flirting with me. Alcohol truly was a cheat code, and I was kicking myself for not finding some way to take advantage of it sooner.
Before she could fully transmit whatever she was trying to psychically relay, another person pushed into the bar behind her forcing her body toward mine. Our bodies pressed up against each other. She looked up at me and I down at her. I took an awkward sip of my beer and tried to ignore the feeling of her tits pressing up against my sternum. It was the first real contact I had had with a girl since Mandy, and my body reacted immediately. It was almost too much and I was hyper aware of the telltale signs of my body swelling with anticipation.
Our awkward pause was quickly broken. "Anyway, I'm Jordan." She offered me her hand to shake, but our forced closeness caused her to raise it above her ear to find room.
"Morgan." I replied, grabbing her right with my left so that I didn't accidentally smack her across the face to reach her hand for an awkward shake.
"So, are you going to ask me to dance or what?" She yelled over the noise of the band playing behind us.
"Aren't we already?" I yelled back jokingly but she immediately led me away from the bar never releasing my hand. She led me into the crowd close to the stage and the next 20 minutes or so were an absolute blur as I lost myself in the lights, sounds, alcoholic haze and movements of her body. The music didn't matter too much, and we were only "dancing" by the every loosest terms. We mostly just faced the band and swayed rhythmically in the sea of bodies.
She placed my hands around her waist and pressed her ass into me. She gyrated and wiggled in front of me while holding my arms around her narrow hips so that I couldn't pull back away from her. I was certain she could feel me getting hard at her teasing, but it was also obvious that was her goal.
I was lost in bliss like that for multiple songs. I could have stayed like that all night. I knew that even if Jordan was just a temporary distraction, I had finally gotten some validation that I wasn't completely hopeless. Maybe I was just drunk and happy to have someone other than myself making contact with my boner, but things were looking up.
That is, until I caught her out of the corner of my eye.
At the edge of the dance floor I saw Mandy, and if it wasn't bad enough that she was actually done-up and wearing tighter clothes than I had ever seen her wear in public, her arms were wrapped around some guy who had his tongue all the way down her throat.
I must have frozen up or something, because Jordan turned around and asked me what was wrong. I shook my head and tried to play it off.
"It's nothing." I said, but I couldn't peel my eyes away.
She grazed my rapidly softening shaft with the back of her hand and said "he certainly doesn't seem to think it's nothing." She went up on her tiptoes, wrapped her arms around my neck and pressed her cheek to mine trying to trace my eye-line. "Who's she?" She asked me.
I knew I was cooked. I may not have had a ton of experience dating, but I knew I wasn't supposed to be in the situation I was in. "Just an ex." I replied.
"Oh, I like her top." Jordan commented, referencing her lavender and pleather corset Mandy was wearing as she did her best impression of how she used to nearly fellate my tongue.
"I've never seen it before." I said offhandedly. It was true. Mandy must have gone on a post breakup shopping spree as I had never seen her dressed so hot - beneath her purple and black pleather corset were tight black shorts that looked straight out of the porn I had been getting newly acquainted with. I couldn't help but wonder if she straddled that guy in them. If she rubbed herself against him up and down until he exploded in his pants, or if she no longer bothered with long games of chicken and instead had skipped straight to fucking.
It was almost like she could hear what I was thinking. Without breaking away from her kiss, Mandy opened her eyes and briefly locked eyes with me. Had she known before then I was watching her?
I didn't have time to think about it for long before my thoughts were interrupted by a defiant "oh fuck no!" Erupt out of Jordan's mouth.
She must have seen Mandy's eye contact, as she grabbed my face and turned my head to kiss me deeply. She tasted like spearmint, alcohol and menthol cigarettes. I was taken off guard at first, but after a few seconds drunkenly leaned into the sloppy kiss. When she finally broke away, I looked back to where Mandy and her man had been and they were nowhere to be seen.
"You ready to get out of here?" I heard Jordan ask below me.
"Yeah." I replied without even realizing the gravity of what she had just asked me.
The fall air was cold outside of the bar and Jordan's heels clumping on the sidewalk were just about the only sound.
"We uh... can't go to my place." She said with an awkwardness that I didn't think was entirely warranted.
"That's fine." I replied. "My dorm is only like a block away." I knew Mike was still back at the bar, and over the past few months he had been making a habit of not coming home until closing time.
A brief silence fell over us as we walked, both of us anticipating what was implied by going to my dorm. Jordan finally broke it: "I'm guessing she was a recent ex?"
"Yeah." I said. "First time I've seen her since."
"How long has it been?" She probed.
"Since the breakup?" I shrugged. "Maybe a couple of months." I feigned nonchalance. It had been sixteen weeks and three days, but she didn't need to know that.
"Seems like a pretty fresh wound." Jordan replied. "You sure you're good?"
I was taken off guard by her question. "Do I not seem good?" I was genuinely curious.
"I don't know." She looked up at me and squeezed my arm close to her. "It seemed like you were pretty stunned by her swallowing that guy's tongue."
"Yeah." I admitted. "I guess I was just a little surprised. I didn't expect to run into her, and it was the first time I have seen her since the breakup."
"It was pretty serious then? How long did you date?"
It wasn't a question I really wanted to answer. "A while." I responded.
"Oh come on, how long?" She pushed.
"Why does it matter?" I countered.
"I just don't think I've ever seen anyone sver shift gears so quickly." She explained. "One minute you were down to party and the next you were..." she held her hand out flat in front of me, then curled her fingers downward.
I felt my cheeks begin to burn. Not just because I had gone soft almost immediately, but because of the implication that she had felt me go soft.
She giggled next to me. We were only about fifty yards from my dorm, and I knew if I didn't get her off of this topic that this night was going to end with her going back to the bar and me dragging my sorry ass upstairs to have a sad jerk-off about what could have been. I knew the only way out was to give her what she wanted so that we could move on.
"Fine, it was about 4 years." I finally admitted.
"Four years!" She gasped. "Holy shit, dude. You dated her the entire time you've been here?"
"Yeah, I guess so." I replied as we started to climb the steps to my dorm. "Does that matter?"
"It does and it doesn't." She replied. There was a mischief behind her voice that I couldn't really place.
"What do you mean?" I asked.
"Well, you're not going to get weird on me, right?" I couldn't tell if she was just teasing me.
"I don't think so."
"You promise?" She raised an eyebrow at me.
My heart was thumping in my ears as we reached the door to my dorm. We stopped at the threshold. I was a little unsure of the protocol. Did I just open the door? Or was I supposed to ask.
"Look, any weirdness I've got is just because I'm a little out of practice." I admitted.
She turned and faced, crossing her arms across her chest to guard herself from the encroaching cold. "Yeah. We'll see about that."
I gestured at the door and tried to sound as cool as I could when I said "do you want to come in?"
"Would I have walked all this way if I didn't?" She snapped back, nodding.
"That's fair." I replied.
I scanned my card and opened the door for her. She bounced in the door. We walked in silence down the hallway and up the stairwells. It was close to 11:30pm on a school night, and the last thing I needed was an RA telling us to be quiet and smelling the alcohol on my breath.
When we got to my door she looked reluctant and whispered "what about your room mate?"
"He's still at the bar."
She nodded and waited patiently for me to open the door. I unlocked it and swung it open. Jordan wasted no time entering, and by the time I had closed it quietly behind me she had crossed the room and sat on Mike's bunk.
"Is this one yours?" She asked as I pulled out my keys, wallet and phone out of my pockets and placed them on my computer desk.
"No, it's the top bunk." I replied, suddenly feeling a bit embarrassed at my inadequate living situation.
"Sweet!" She replied, teasingly. "I haven't been on the top bunk in years." She stood up and turned to begin to climb the ladder, but stopped at the bottom. "Honestly I can't remember the last time I was in a dorm. I've had a house since my sophomore year." She paused doing the math in her head as she tossed her silver purse up onto my bed. "What year did you say you were?"
"I didn't." I replied, "I'm a sophomore."
She tilted her head and gave me a half smile. "Kinda old for a sophomore, aren't you?" She turned and began climbing the ladder.
"Not really." I replied. As she reached my bunk I couldn't help myself but to peak under her skirt. It almost felt like she meant for it to happen. I got a fantastic view of the back of her white panties as she crawled into my bed before she turned and draped her legs over the edge. "My room mate is the old one. He's got some sort of scholarship that gives him free room and board for all four years."
She seemed entertained as she swung her legs back and forth over the edge of the bed.
"I'm actually only 19." I admitted.
"Well that explains a lot!" She laughed as she counted on her fingers.
I leaned on the side of my desk and tried to keep my eyes plastered to her face as she pursed her lips. Her legs were closed, but the temptation to just give in and stare at her exposed thighs was intense. "What do you mean?" I asked.
"Well you've been so damn awkward all night." She giggled and put her hand over her mouth. "I thought it was just me, but you had been dating that girl since high school."
"Yeah. Sorry, I guess."
"Don't be sorry. I'm actually kind of relieved. I thought for sure..." she trailed off for a moment lost in thought. "Are you just going to awkwardly stare at me from down there or are you going to join me?"
"Oh... yeah." I kicked off my shoes and moved to the bed.
"So she was your first, huh?" She asked me as I climbed the ladder.
"Yeah." I replied, flopping myself up onto my mattress and reclining backwards behind her. "I guess so."
She turned and put her forearms on my chest as she leaned towards me. "And I'm the first girl you've hooked up with since?"
Her face was six inches from mine. "Are we hooking up?" I teased.
"We'll see." She countered as she brought her lips to mine. It was a slower, more passionate kiss than the one in the bar. It lasted a minute before she broke it off and leaned sat back up. "I just need to know that you're not going to freak out on me."
"I'm not going to freak out!" I said, exasperated. "I thought we had moved past all those questions."
"Not by a long shot." She swung her legs up onto the bed and sat criss-cross next to me, careful to ensure that her skirt stayed draped over her lap. "I've just had guys freak out before and it isn't pretty."
"What, you make a habit of picking up guys on the rebound?"
"I wouldn't say it's a habit." She said cautiously. "It just seems to happen to me a lot."
"A lot?" I probed. "How many guys are we talking?"
She gave me a wide eyed look as if I had just slapped her across the face. "See? You're already freaking out!"
She was right, I needed to chill out. "No. You're right. It doesn't really matter."
"You're right. It doesn't." She reinforced. "We're just here to have fun, right?"
"Right." I agreed.
"Promise?"
I held up my hand in a mock scouts honor gesture. "I solemnly swear that I am just here to have fun and not freak out."
"You better not." She replied and hooked her hands underneath the bottom of her tank, peeling it up and over her head.
This time I couldn't help it. My eyes were drawn to her pink bra and how it pushed up her chest on her tiny frame. When I looked back up and met her eyes, she gave me a a quick smile and reached behind her back.
Before her bra had even fallen completely off of her, I had begun to move towards her chest. My mouth found her small pink nipple almost immediately and my tongue flicked back and forth over it.
She leaned back on one arm and held my head with her other. I made little circles with my tongue and felt her chest raising and lowering beneath me. Her nipple tightened as I lapped at it, and she ran her fingers through the back of my hair. After a minute or so she brought her free hand around to my chin and brought it up to her mouth, kissing me again and pushing me backwards to reclining on my elbows.
When she broke free she sat up, topless, looking down at me. Her free arm covered her nipples, and she blushed slightly and broke eye contact turning her head. Her tits were perfect in nearly every way - and only the two small faded scars on their undersides betrayed why they were so unbelievably perfect.
Her right hand moved to my lap and traced the outline of my hard shaft through my jeans. Feeling another person touching my cock, even through my jeans, for the first time in months was almost too intense for me. I collapsed backwards on the bed and turned my head away from her perfect chest so I could concentrate on my breathing. Her light touch transitioned to a massaging motion up and down my shaft, and the last thing I wanted was to bust in my pants before the action even started.
I think she saw the distress on my face as I tried to relax myself a way from the tingles building at the base of my dick. She stopped stroking for a moment giving me a brief respite. "Guess it's been a while, huh?"
I could feel my cheeks burning wondering if she could tell how close I was. "Yeah I guess so." I was too embarrassed to turn to look at her, but at least I wasn't done yet. She let me sit for a moment and then I felt both of her hands unclasping my belt and unbuttoning my fly.
"Let's see what we're working with." She said as she hooked her fingers into my waistband. I lifted my hips as she pulled my jeans down to my thighs, leaving my shaft fully contained within my boxer briefs. She let out a little moan. "No wonder she stuck around for four years. You're packing!" She traced a fingernail through my boxers directly below the head of my dick, right on the spot that was always so sensitive.
My shaft flexed in response, and when I finally brought myself to look at her face she was biting her lower lip staring directly at my bulge.
"She took all of that?" She asked me, in disbelief.
I nodded.
"And you were her first?"
I nodded again. I didn't know why she kept bringing up Mandy, but it seemed like she was getting turned on knowing that she was my first post breakup experience. Her free hand was braced against the bed in between her legs, and it was clear she was putting pressure on herself over her skirt.
"Did she have trouble with it the first time?"
"Uh... no?" I finally responded with half a question. "Mandy never told me I was particularly well endowed, and we messed around a lot before we ever did anything."
"I guess she just didn't know any better." I couldn't tell if she was just fucking with me or if she wanted details, but she gave me a look that said "go on."
"We played 'just the tip' for quite a while before we ever actually fucked."
She let out a small giggle. "Doesn't everyone? That doesn't necessarily make it easier."
"No?" I asked. It had seemed pretty easy at the time. Mandy and I had been on the verge of having sex for quite a while before it actually happened. We went through the steps of dry humping with clothes on, to doing it in just our underwear, to outercourse over a matter of months. It was amazing we had held out as long as we did. The night we finally "went all the way" I had been stroking her entrance with the head of my dick, playing in her wetness when something came over her and she moved her hips slightly causing me to penetrate her by only about an inch. I probably could have pulled out right then and we would have been able to remain "virgins," but I froze. Maybe it was shock at what was happening or maybe it just felt good enough that I couldn't bring myself to pull out, but after a couple of seconds she said "you know, we're no longer virgins, right?" and pushed down onto me all the way to the base of my cock.
"Well, not for me anyway." Jordan trailed off as if she were lost in thought.
"Maybe you weren't warmed up enough?" I probed.
"Something like that. I was maybe a little overeager to lose my virginity, and he..." she paused to think for a moment while absentmindedly running her fingernails up along the bottom of my shaft through my boxer briefs. "He seemed like the right guy. I just didn't want to wait anymore you know?"
"Sure, when you're ready you're ready."
She looked down at my cock straining against the fabric of my underwear. "Yeah. Speaking of ready..." She got up on her knees and swung one leg over my thighs, straddling me just above where she had pulled down my jeans, but low enough that her skirt did not cover me. She leaned forward and rubbed me roughly with her palm. "So how long did she make you wait?"
I didn't explain that we had agreed to wait and that it was a momentary lapse in our willpower that had eventually pushed us over the edge. Instead I just simplified. "Two years."
"Two years!" She exclaimed. "Oh you poor baby." She continued to rub my shaft up and down as if she were comforting it. She continued in a voice that was half a tease, and half overly sympathetic: "That's a long time to settle for handies. She must have gotten a lot of practice."
I nodded. Truthfully Mandy and I hadn't even started doing much more than making out until more than two years in, but the way she was cooing at me I wasn't about to correct her.
"Still," she paused mischievously "I'm willing to bet mine are better." She pulled down my waistband with one hand and took my shaft in her other. She made direct eye contact with me and began to pump causing her tits to bounce with every hand movement. She certainly wasn't wrong. The way she cascaded her fingers as she pumped me rivaled anything I had ever felt. It was like she was milking me, and it was all I could do to hold back. She opened her mouth slightly and craned her neck forward, mimicking an o-face as though she knew exactly how little it would take to push me over the edge. I wouldn't even need her mouth. My hips bucked up beneath her trying to fuck her hand and she increased her pace to match my intensity. She had to know I was close, but she showed no signs of slowing down.
I only lasted a few more seconds before I had to stop her. I grabbed her wrists and stopped her motion. It was the last possible second. Her open mouth turned to a mischievous smile and she teasingly asked me in a pouty voice "too much?"
I nodded. Even though I had stopped her pumping she had me teetering on the edge, close to exploding in her hand just from her grip. I knew if I mistakenly flexed my kegels or if she pulsed her grip, or even if the AC kicked on and a breeze hit me in just the right way I was going to explode in orgasm. I tried to control my breathing. "That's insane." I gasped out. "How the fuck did you do that?"
She slowly released her grip on my shaft and let my waistband snap back above my balls. I released my grip on her wrists and sat up on my elbows.
"Don't you want to me to finish you off?" She asked me in a pouty tone as put her hands on her knees and shrugged her shoulders causing those perfect pink nipples to bounce in front of me.
"I do, just not yet." I replied and shifted my weight to my left hand, freeing up my right to reach towards her inner thigh below her skirt. "I just want to do something for you first. It's only fair."
When my hand made contact with her thigh, her face went from sultry to panic and she blocked my hand with both of hers. "Wait" she commanded, holding my hand in place.
"Uh, alright?" I agreed withdrawing a bit confused.
"You sure you don't want to just finish?" She pouted again, and placed her right hand on my shaft using the lightest possible touch to stroke it gently. "I don't mind you know. When you told me I was only the second girl you had ever been with I kind of knew you'd be quick." She was right of course; it wasn't just that she was exceptionally skilled, but I had surprisingly little stamina. I could usually hold out with Mandy as long as I needed, and now I was in danger of blowing my load before I even got close to Jordan's pussy.
Her left hand remained in her lap holding my right hand and making sure the hem of her skirt didn't ride up. Her hand was unbelievably soft as it stroked the exposed skin above where my waistband was resting. I would be lying if I said that the prospect of her milking me to completion wasn't overwhelmingly tempting but this was the hottest girl I had ever been with and I had no idea when I would be this close to getting fucked again if I blew now, I'd blow it.
"I just figured it was your turn." I choked out, trying to ignore the feeling of her hand lightly brushing up and down the length of my cock. "Don't you want to cum too?" My words caught in my throat as she hit the particularly sensitive spot directly under the head of my dick that made me twitch and flex against my will.
"You have no idea. But.." she trailed off again breaking eye contact and turning her gaze to my cock.
I knew I was on borrowed time. Even though she was no longer stroking me, the feeling of her light touch on my shaft and her soft thighs on my bare skin beneath her skirt was threatening to send me cascading over the edge. I was doing my best to control my breathing, but she had pushed me so close while she was pumping me that I could still feel the tingles at the base of my cock threatening to spread across my body at any second. If she decided to put any downward pressure on me, those little tingles would explode in a mess all over my belly. The embarrassment I felt the first time I popped in my pants with Mandy would be nothing compared to what I was about to feel if I came all over myself during foreplay with this girl I barely knew.
She scooped her fingers under my shaft and began using her thumb to make tiny circles on my frenulum. She was determined to make me cum, whether I was ready or not. I had to do something to give myself a moment of rest. I was out of options. It was a risky play but I was going to have to admit my predicament if I wanted any shot at getting laid. "Like you said, you give a really good hand job. You were going to make me bust and I wanted to be sure I returned the favor first so you didn't think I was selfish."
She exhaled sharply, released my cock and slowly loosened her grip on my hand. She kept her left hand on the hem of her skirt as a signal that she wasn't ready for me to begin exploring her.
"Look, I really do want to." She said, her voice quivering. "But you should probably know that I'm not exactly..." she paused apparently trying to find the right words. "I'm not exactly like your ex."
"No shit." I said, glancing back down at her perfectly sculpted chest. I assumed she meant that she wasn't looking for anything long term, and her hesitation was just about me getting attached. "Look, we said this was just for fun right?"
"Yeah."
"Then let's both have some fun. There's no reason to leave you out of it."
She seemed to turn that over in her head. "It's not that." She said, her voice still quivering ever so slightly.
"Then what is it?"
"Last chance. I can just finish you off now," she moved to grab at my dick again and began to give it a few swift strokes. I slapped her hand away before she did any real damage. "We can just save it for another night when you've maybe got a little clearer head."
I shook my head. I needed to see her.
"Ok. But remember you promised me you wouldn't freak out." She grabbed the hem of her skirt at the point where it was resting on top of each of her thighs.
"For the last time, I'm not-" was all I got out before she lifted her skirt to show me her white panties. I don't know why, but my brain absolutely shuts down at the sight of panties. Maybe it was because Mandy and I spent so long edging each other while we were clothed, or maybe there is something more deeply rooted in my turn ons from way back, but these were immaculate. White cotton with a tiny pink bow on the waistband.
I was so entranced by her panties that I almost completely didn't notice that the shape of her pubic bone was different than what I was expecting. Instead of flat across the bottom with a hint of the shape of her labia like I would expect of a girl straddling me, there was a small bump in middle of her panties. More than a small bump - a small bulge.
"Sorry I didn't tell you sooner. I honestly didn't think it was going to come up."
I knew when I had broken up with Mandy that I wanted some college adventures, but I hadn't even considered a situation like this.
"Is that...?" I choked out. My brain was racing. I didn't know what to do about what I was seeing.
"It is." Her face was awash with concern, clearly reading my surprised reaction as negative. She lowered her skirt again until her bulge was out of sight. She was back to being the incredibly hot topless blonde I had picked up in the bar against all odds.
"But you're so hot!" I replied in disbelief.
"Uh, thanks." I felt her body tensed a little. I don't know what reaction she had been hoping for but apparently it wasn't that. She started to lower her skirt, "Look, I can just go." She put her hands on my chest and began to dismount me.
"No, don't." I grabbed her hands to stop her from getting off. On one hand I knew I should have just let her go. If I wanted to play with a cock I could play with my own. On the other hand, I was so close to cumming anyway, what was I going to do? Show her the door and then hop back in bed and masturbate to the thought at what could have been? "Just give me a minute to process this."
She rolled her eyes and settled back down on my lap, this time higher up. Closer to me. Her pleated denim skirt was draped over both of us so we were out of sight, but another inch and I just knew our parts would be touching. I knew I shouldn't want that but part of me did. I thought I was completely straight? Maybe I could just ignore it? My body was fooled despite what I had just seen. In front of my eyes now was just an incredibly hot girl straddling me, and my cock was certainly satisfied with being nestled underneath her skirt so close to where her pussy should be.
An incredibly hot, increasingly annoyed girl. I still wasn't sure what I wanted, but I knew if I didn't say something quick the decision would be made for me.
"I'm just a little shocked you know?" I think I'm into it I've just never..." even considered that I might be.
"Seen a penis?"
"Well, not on a hot girl." Not in person anyway. In my recent foray into the world of porn I had definitely stumbled across pictures of women with dicks, but they were always much larger and I always kind of suspected they were photoshopped. I had never really considered that I would be face to face with one in my own bed. It hadn't been much more than a tiny bulge in her panties. "Can I..." I paused in disbelief of what I was about to ask. "... See it again?"
I thought she was going to leave right then and there. She looked so annoyed. To my surprise though, she just rolled her eyes lifted her skirt again. I'm sure it wasn't the first time she had gone through this.
Despite being so close to touching me, I wasn't surprised by it this time. It seemed so non threatening. It wasn't a "cock" or a "penis," it was just a little bulge. It didn't even look like she was hard. I couldn't make out much of its shape, other than where a quarter-sized wet spot had formed showing the outline of her tip through the wet fabric. Despite being soft, she must have been turned on to drip that much - I usually only dripped precum when I had been teased for a really long time and certainly never in that quantity, so it seemed weird to me that she wasn't hard.
Huh. "She wasn't hard." It was a weird thought that so easily popped into my head and it took me a few moments to chew on that idea.
I snapped back to reality when she lost patience and asked me in an annoyed "Well?" That carried the weight of all the times she had gotten to this point with other guys in the past but hadn't been able to proceed.
"Does it like, work?" I asked. I was stalling for time while I tried to process what I wanted. I had all kinds of conflicting feelings. Up until that moment I had always considered myself 100% straight, and I at least still thought I was. She was still the hottest chick I had ever hooked up with and she was straddling me with a wet spot in her panties. That part of me wanted her. The part of me that was embarrassed about what Mandy would think if she found out wanted to slow things down.
"Kind of." She responded. Her voice sounded a bit relieved at my question. Like we were over some imaginary barrier that she had been nervous to cross. She looked down at herself quizzically and touched her wet spot with the tip of her finger. "I've been on hormones for a while so I guess it's a little different."
"Does it still get hard?" I asked out of genuine curiosity.
"She still gets hard yes," she put emphasis on the pronoun, correcting me. "But it's different when she does. She's softer than she used to be, and much more sensitive."
I felt like my heart was in my throat as I slowly reached out to touch her over her panties. She didn't stop me though, she just watched my hand as it closed the distance. When I got there I realized I didn't know what to do - I didn't really have a plan passed this point. Was I supposed to pull her panties down and stroke her? I wasn't ready to commit to that. It felt like a big step so instead, I just made little circles with my thumb on her wet spot. It was centered right above where her clit would have been if she were... you know... normally equipped.
Jordan bucked her hips towards me and sighed, like she had been aching to be touched. I knew that feeling all too well. Her small thrust into my hand was enough to center her directly over my shaft.
I continued to make little circles on the head of her penis, watching her face as she closed her eyes and gyrated her hips towards me. With each small circle of her hips she got a little lower towards me, until she was hovering an inch above my shaft. It wasn't really too different from the times when I had rubbed Mandy's clit, but it still startled me when I felt her throb against my hand and begin to swell beneath her thin material. I initially pulled my hand away, and her gyrating immediately stopped and she gave me a pained look that suggested she wanted more.
"Let me take it out?" I asked, trying to cover for my squeamishness. I didn't want to be rude. She was already so wound up I figured I could buy myself a little time. And besides - it wasn't like I hadn't jacked off before. How different could it be?
She blushed and turned away slightly. "Her." She corrected again.
"Can I take her out?" I reiterated. It felt weird to me to be using pronouns for a penis, particularly feminine ones.
She gave me a satisfied nod. "If you want."
I used one hand to pull the front of her waistband down and with my other scooped her shaft and balls out. I let her waistband settle beneath her balls, and went back to leaning on my elbow.
She was completely shaven, and it was immediately apparent to me why she thought I was so large. She was tiny by comparison. Unrestrained by her tight panties, her shaft swelled and protruded forward, but even then her cock couldn't have been a full three inches from base to tip, and didn't seem to be as rigid as I got.
I reached for it but stopped myself short. I looked up at her face to judge her reaction. She blushed at me and looked away. I steeled myself and took her tiny shaft between my thumb and forefinger and gave it a couple of tiny pumps. I tried to just focus on her perfect pink nipples and put out of my mind what I was actually doing. I felt her stiffen a little more in my fingers, becoming a little more firm with each throb. It was softer than mine was when I was hard. It was more like mine felt when I was only half erect. Reacting to my touch she lowered her hips down into mine. She ground herself into the base of my shaft and rotated her hips backwards putting pressure down my shaft just like Mandy had so many times before. The pressure was luxurious. Familiar. Relieving. Despite the lack of a pussy, it felt just like all the times Mandy had rocked back and forth on me until I couldn't take it anymore and plastered my underwear. It just looked a little different with the top of my dick poking out from underneath Jordan's tiny pink balls.
I began to stroke her, using two fingers to roll the skin of her shaft up and over her glistening head. It felt a little foreign to me - the angle was off from what I was used to, and when I jack off I typically use my entire hand rather than just two fingers, but there was no way my other fingers would fit with the little space I had between where her tiny shaft ended and her balls crowded forward from the pressure of the waistband of her panties.
Her dick was small and fairly soft between my fingers. The way she was synchronizing the movements of her hips with the movements of my fingers, it didn't feel so much like I was jacking someone off as much as it felt like I was controlling some giant sex toy on top of me. I moved down on the shaft and she moved forward on me. I moved up on her shaft and she moved back. The tiny movements of my fingers were being translated into massive pressure grinding into me. I began to lose myself in that pressure and probably could have easily tumbled over the edge, which was by it was so confusing when I felt something warm and wet drip onto me. For a brief moment, I thought I had cum and just not felt it.
"Oh sorry." She whispered, glancing between the mess she had just made on me, and my obviously stunned, confuddled reaction.
"Did you just...?" I asked trailing off. I couldn't bring myself to ask the full question almost as if asking it would make it a reality.
"Cum? No." She giggled as if I was ridiculous for asking. "That's just my lube." She reached down with one hand and touched the wet mess she had made below my navel.
"Lube?" I asked.
"You know..." Her voice dropped to a whisper as if she was embarrassed to say it. "Precum?"
I looked at the tiny cock between my thumb and forefinger poking out from underneath her bunched up skirt. Sure enough, her tip was glistening and a faint string was connecting it to the wetness on my body.
"That's a lot." I remarked, continuing the tiny movements with my hand, not wanting the pressure of her rolling hips to stop.
"Sorry." She said replied obviously a little self conscious. "It's just been a while since..."
"Since what?" I prompted, feeling powerful at how her body was reacting to me. I could feel her shaft twitch and flex with each of my tiny strokes and her light body was twitching on top of me with every tiny movement.
"Since I've been..." her voice was little more than a whisper, "jacked off."
"You don't normally?" I asked.
"Not anymore." She replied between her tiny gasps. "When I'm all by myself I typically just use a vibrator on her." She paused as a shudder worked through her, "and most of the guys I've been with don't want anything to do with her."
"What do they do then?" I asked trying to sort out what she was expecting.
"Usually nothing. I just do stuff for them." She focused on my pumping hand continuing to match my movements with her hips, but looked like she was mentally far away. "Most guys are pretty content to finish with a blowjob before my bottoms ever come off."
She leaned back on one hand and and reached out to touch the wetness where her precum had dripped onto me with the other. I paused stroking her to watch her to work. She gathered some of the wetness between her fingers and reached down to the head of my cock where it was poking out beneath her. She mixed her precum with mine and spread it all over the head of my dick. Her tiny fingers played over it tickling me almost unbearably. I closed my eyes and let my head fall back, enjoying the combined sensation of her hand lubing me and her ass pressing on the base of my shaft.
The feeling was short lived though before she stopped and dismounted me. The sudden lack of pressure and sensation was jarring. My shaft throbbed pathetically in need as she kicked her leg over me and kneeled next to me. She looked entertained by my twitching. "I have to say, you surprised me." She said, hooking two thumbs in the waistband of her short skirt. "I thought for sure you were going to throw me out."
"I don't think I could if even if I wanted to." I admitted. "I'm way too wound up at this point to think clearly." It was true. My dick was doing all of my thinking for me, and he had decided for me that he was completely fine ignoring her extra equipment.
"Oh no!" She mocked in a played up pouty voice. "You're not too wound up to fuck me are you?" With one motion she pulled down her skirt and panties, extracting her legs quickly. She tossed her bottoms over the side of the bed and perched next to me on her knees. The way she arched her back and cupped her breasts with her hands made her look like a porn star, her only hint of non femininity was her tiny glistening shaved cock innocently dangling over me.
Her words caught me completely off guard. I guess I didn't even consider what the endgame was going to be up until that point. "Fuck you?" Was all I could reply, the words catching in my throat.
She swung a foot over my hips and kneeled mere inches above me. "That is why you brought me back here right?" Her voice was accusatory as if it were some big con I had been running. "What did you think we were going to do?"
"Uh yeah." I agreed. It was true after all. A short five minutes prior I had been all in on busting my slump with this girl. Now it seemed like so much more than that.
"Oh come on. Don't chicken out on me now." She reached behind her back and took my shaft in her hand. She must have seen the reluctance on my face. "Sure feels like he's game for it." She lifted my cock and wedged it between her perfect ass cheeks that had been grinding into me on the dance floor just a short time ago. "Are you like, scared or something?" She tickled the bottom of my shaft with her fingernails as she raised and lowered her body, effectively stroking me with her ass cheeks.
"No it's not that." I had a hundred different thoughts swirling in my head but the only one that was able to bubble to the surface while she stroked me was "I've just never done anal before."
This time her reaction was more of a laugh than a giggle. She knew I was putty in her hands. She lifted her ass off of me, continuing to tease me behind her back with her left hand. With her right she deftly reached down to her silver purse and produced a small purple and clear bottle. She squirted a little into her hand and reached behind her back. Her entire body arched backwards causing her tits (and cock) to press outwards over me. "That shouldn't be a problem." She said, her voice full of mischief. "You've got the easy job."
I couldn't see her exact movements with her right hand, but the way her eyes squinted and she blew through pursed lips left no question. Her lubed right hand replaced her left, stroking my dick. She placed her left on my chest and leaned forward, her short blond hair falling forward to frame her face with a heart shape. "Just relax." She reassured me as if she were cooing a frightened horse. She must have seen the swirl of panic coursing through me mistaking my conflicting emotions of reluctance and horniness for concern over the mechanics of the situation. "It's easy." I felt her lower her body towards mine and the head of my dick came to rest on something solid. "We can just try the tip, and if you don't like it I will pull you right back out."
She rotated her hips in little circles, putting immense pressure on the head of my cock. Despite my misgivings, there was no way I was going to back out at this point. We locked eyes as she swirled, and I found myself getting impatient wondering if she was going to move me to her opening.
Her lips parted and her eyes half-closed. She exhaled deeply and pressed onto my head.
What I thought had been the solid surface had been pressing against gave way and I felt a tight ring grip the head of my cock. She inhaled sharply as I crept in. Instinctively I thrust my hips forward towards the source of the pressure and her face turned from a zen calmness to a wide mouthed grimace as a high pitched loud moan escaped her. It must have taken her by surprise. She immediately released my dick with her hand and covered her mouth to stifle her moan.
I couldn't have been more than an inch in, but I stopped my thrust and unclenched my hips.
"So much for 'just the tip'"Jordan eked out between gasps.
"Sorry." I replied. "It feels different."
"Yeah? Good though?" She asked as she leaned back to hover over her heels.
I nodded, trying to control my breathing, excitement and nerves. She was right, it felt amazing. It was rougher than Mandy's vagina, but mostly it just felt significantly tighter than anything I had ever felt before.
She sat perched for a moment gathering her composure before she reached down between her legs to feel my shaft. I felt her finger trace the length of my cock that wasn't yet inside of her. Her eyes snapped up to meet mine with a shocked look on her face. "Oh God. You're barely even in yet!"I watched concentration cascade over her face. She exhaled. I felt her loosen a little and she grimaced as she pushed downward another inch.
I'm not particularly well endowed, so maybe it was just because she hadn't fucked in a while or maybe the last guy she had been with had been particularly small, but it seemed like it was taking her pretty considerable effort to push me in. After pausing a moment to gather herself again, I felt her loosen and I slid in a little further. As she pushed down she brought her hand to her mouth to stifle her moan. When she lifted off of me briefly, a shiver rocked her body and her moan turned to a more feral gasp. She pushed down again and made it an inch deeper. Then again, deeper, and once more deeper still. With each push her cock strained upwards as if it were trying to fuck my ceiling. It seemed almost like it was connected to mine - each time I thrusted into her, she throbbed and seemed to grow.
Each subsequent push came quicker, and with each thrust her moans got higher pitched until she finally made it to all the way to my base and her voice was nearly squeaking. Feeling that she had finally taking all of me, she let out a satisfied purr through her hand. I looked up at her face to see her looking down at her own penis. She was rock hard, pointing toward the ceiling, and absolutely glistening with her own precum. It looked like she had grown a full two inches since I had first entered her. It was no longer a little fleshy shaven abnormality dangling from her pubic mound, this was a full-on raging cock.
She looked just as surprised to see it as I was. She stopped thrusting down on me momentarily and just stared at it in wide eyed disbelief as though she had never expected to see it again. She removed her hand from her mouth and began to reach down toward it. Her movement was slow and cautious, almost as if she were frightened of it. She never actually got there though. Two inches away from touching her shaft I felt her body clench on me and her weight lurched forward. A long, whining "oooooh" escaped her lips and she began to convulse on top of me.
Her tightness was already too much for me and I had been doing everything I could to hold out as long as possible. The excitement of trying anal for the first time combined with the tightness gripping the base of my shaft and the visual stimulation of her now rock hard cock protruding from her perfectly smooth public mound had me already dangerously close to the edge. I had wanted to hold out, I wanted to fuck her properly but her body was going haywire on top of mine and I couldn't hold back anymore. I bucked my hips into her and a hard grunt escaped her.
The violent electricity that I had been doing my best to hold back exploded from the tip of my cock, deep inside of her. Some part of me deep down felt I should be embarrassed that I couldn't hold back, like it was shameful that I couldn't control my body. I knew somewhere that I should be conflicted about who I was fucking, and I just knew she was going to make fun of me for cumming so quickly, but the electricity gripping my entire body was too strong to deal with any of that.
It was like my first time with Mandy all over again. I had only lasted a few strokes then, too before the tight wetness of her virgin pussy sent me teetering over the edge. I had held on for as long as I could, and probably waited further into my orgasm than was strictly safe before I pulled out and finished myself off with my hand filling her belly button with my cum as she rubbed herself with her fingers trying to get any level of satisfaction. It had been mortifying, but at least she and I had been together for so long that I knew she would understand.
"Oh god I need to pull out!" The realization hit me like a ton of bricks as my body involuntarily convulsed into her. It was like my mind was screaming at me - all those times with Mandy I had never actually cum inside of her - the risk of pregnancy was just way too high. I pathetically tried unclench my body to pull out of Jordan, but I couldn't get leverage.
My mid-orgasm panic was interrupted by something warm and wet hitting my neck and chest. My eyes came back into focus and I looked down at her to see face scrunched up with her mouth open almost like she was in pain. My eyes followed her arm down past her perfect, bouncing tits and to her hand wrapped around her own cock. Milky white sticky cum was still dribbling from her tip, streaming out from her in a single, consistent stream, unlike my own spurts that i was used to. It began to pool on my stomach just below my ribs, and ran into my belly button just like my cum had run into Mandy's all those times before.
The whole thing probably only lasted a few seconds. Between the shock of being cummed on the convulsions of my own orgasm, and the sheer grip she had kn my shaft, I never did get enough leverage to pull out of her. I let out my own grunt as my body seized up one final time, sending me into a half sit-up. She grabbed the back of my neck and braced me towards her tits. We froze like that. Cum dribbled off of my torso and down the side of my belly as my cock rhythmically throbbed, I grunted pathetically with each pump as i released deep inside of her.
Our eyes finally met as my throbs began to slow down. my orgasm retracted and i laid my head back, resting my head on one hand under my pillow.
"Sorry." I stammered. "I tried to pull out, but I couldn't."
She giggled. "I bet you used that line on your ex all the time."
I wanted to tell her that I never had. That I had always managed to pull out with her, but the words never came out, my mouth just opened and closed pathetically.
"Besides." She dipped a finger in the puddle of cum that had gathered into my belly button, and raised a curious eyebrow "it looks like I couldn't hold back either."
She stared deeply into my eyes and brought her cum-covered finger to her lips to taste her work. My body was confused by the visuals. I knew I shouldn't be turned on, but I still felt rock hard inside of her and was twitching sporadically.
I decided there was no turning back from what I had just done and what it may all mean for my sexuality so I just enjoyed the view of the beautiful blonde girl, filled with my cum tasting herself with one finger in her mouth.
I didn't have too long to dwell on it. Jangling of keys and the rattle of them being inserted into the lock threw us both into a panic. In one motion Jordan ripped herself off of me and dove to the side of my bed away from the door.
Mike stumbled into the room and almost immediately his drunken eyes landed on my full-mast erection standing at attention like a beacon at the top of my bunk bed.
"Oh shit, sorry!" He exclaimed turning away. "I didn't know you had come back already I thought you were still at the bar."
"Yeah, no uh.." was all I got out while futily attempting to cover myself with the very duvet I was laying on before he bent over and picked up Jordan's discarded panties.
"Wait, you have company?"
Jordan popped her head up beside me and gave a timid wave. "Hey." She called out.
Mike turned to see the new voice, and recognition spread across his face. "Oh. Hey Jordan."
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