When All Else Fails Pt. 02

That night Winston lay wide awake in bed. He couldn't get the encounter with Jeff out of his mind. He thought about every detail from Jeff's soft lips pressing against his own to the eager, muffled moans coming from Jeff as Winston shot his load into the other man's mouth. Getting his cock sucked felt one hundred times better than anything Winston could have imagined or replicated with his hand. Just thinking about the encounter was getting his cock stiff with anticipation. He was fighting himself not to seem too eager and message Jeff for round two so soon after the first. But it was clear that Jeff had enjoyed it as well. The only hesitation was the darker thoughts that kept intruding Winston's, otherwise, blissful memory.

"Am I gay now?" He kept asking himself.

He'd not only enjoyed a blowjob from another man, but he also really enjoyed kissing Jeff. Winston had felt Jeff's hard cock against his leg when they were making out, and it had turned him on so much. This was all so confusing for him. On one hand, Winston didn't consider himself queerphobic. He was great friends with his roommate, Havi, and Havi was as queer as they came. He was an openly gay trans man, and it was one of the things Winston loved about him. Winston thought Havi was so courageous because he didn't seem to care at all what others thought of him. Havi loved men and never minced his words in front of Winston when expressing that. Havi had also seemed so happy and free. Winston envied Havi's way of moving as though he didn't have a care in the world.

So then why was the possibility of being a gay man stirring all of these emotions within him? Winston thought about it. Perhaps it was just something he never saw for himself. He'd always been interested in women. He usually watched straight porn. Though, if he was honest with himself, he did focus on the guys in porn just as much as the women. And he couldn't stop thinking about the electric feeling of Jeff's hard cock grazing his thigh when they were making out. He wanted more. He wanted to feel Jeff pressing into him harder so that he could feel the thinner man's hard cock rubbing against his own. He also wanted to touch it.

Winston's train of thoughts was interrupted by the sound of the door opening. Havi walked into their small dorm room.

"What the fuck man?" Havi said, "Why is it so dark in here? Are you jerking off or something?"

Havi turned on the standing lamp by the tv near the door.

"Damn Win! You must be really happy to see me," Havi said with a chuckle.

Winston followed Havi's eyes, and to his horror saw his own raging boner making a tent in his sweatpants. He sat up and scrambled for his blanket to cover himself. Havi just laughed and waved it off.

"Chill out, man! It's not even a big deal," Havi said, "I'm just teasing."

Winston secured the blanket in a crumpled heap over his lap, trying to look as normal as possible. His cheeks burned red.

"Yeah..." Winston said, "Just yknow... putting it away."

Havi set his backpack on the chair of his desk that was on the wall opposite their shared bunk bed. He'd just come back from his job working at the campus library. He chuckled again and smirked.

"I mean, you don't have to put it away," Havi said, hunching his shoulders.

Winston was stunned. Before he could figure out how to respond, Havi grabbed his shower caddy and towel.

"I'm gonna shower real quick," Havi said nonchalantly.

He kicked his shoes off and stepped into his crocs, and then he opened the door and left.

Winston sat there in his bed trying to process what had happened. Did Havi just insinuate that he liked seeing Winston's boner? Winston didn't feel weird about it or embarrassed or upset. He felt flattered. He never thought he was handsome enough to catch Havi's attention like that. Havi seemed too cool for him sometimes. Either way, it felt good. Winston let his mind drift to Havi. Havi was really good looking. He was shorter, about 5'5. He was Indian with copper brown skin and dark, long hair that he wore in a ponytail. Havi was also very fit. Havi had played tennis in high school and the first two years in college. It was only this year, his junior year, that he'd decided to ditch it and focus on studying for the MCAT.

"It's not like I was ever good enough to turn pro," Havi had said when Winston asked about it early on in their friendship.

Havi still played tennis a few times a week as part of the school's tennis club, and it showed. Havi was slender and toned with defined thighs and calf muscles. The few times Winston had seen him shirtless, he'd seen Havi's flat, shredded abs and pec muscles as well as his toned biceps, triceps and forearms. Winston would try not to stare at Havi's body, especially the faded scars just below his pecs that were evidence of the top surgery he'd had during his freshman year. Winston was definitely curious about Havi. He just never allowed himself to linger on it.

However, now after the experience with Jeff, the thoughts about Havi felt more accessible to him. Winston thought about the other day when Havi had changed into his tennis clothes right in front of him. Havi was very hairy with hair all over his chest, stomach and legs. He had a full beard that he kept shaved down to stubble. Winston had watched out of the corner of his eyes as his roommate had stripped out of his jeans and t-shirt. Then his boxers, but at the last moment before Winston could see his cock, Havi turned his back to him. Winston had averted his eyes ashamed that he was staring so blatantly. He was also a little miffed. He didn't know the status of Havi's bottom area and whether or not he'd had any surgeries. Winston had been so curious and for that split second he was excited with the possibility of discovery, but was then immediately ashamed of objectifying Havi that way.

Thinking about that time paired with the thoughts about his earlier meeting with Jeff had Winston riled up. He cast the heap of blanket aside and plunged his hand into his sweatpants. He started jerking his hard cock furiously. If he was quick, he could cum before Havi got back from the showers. Winston pumped his cock thinking of Jeff's lips and tongue and throat and then Havi's toned stomach and thighs. He could feel his orgasm building as he fantasized about Havi's hairy pecs and the strip of hair below the waistband of Havi's boxers that Winston had seen in a flash just before Havi had turned his back to him. Winston jerked and worked his cock feeling it get harder and harder. He was just on the brink of shooting his load when he heard the knob of the door turning.

Winston moved fast. In one fell swoop he pulled his hand out of his sweats and pulled the heap of blanket back over his lap, concealing his boner. Havi walked into the room a second later with his shower caddy in one hand, his clothes he'd been wearing earlier in the other and just a towel around his waist.

"How was your shower?" Winston asked, trying to seem normal.

"It was good," Havi said, "There's nothing like a hot shower after a long day."

Winston nodded and smiled, hoping that he wasn't coming off too weird. Havi didn't seem to notice and went about his usual routine. He threw his clothes into a small laundry hamper next to his desk and put the shower caddy back in its place. He walked over to the small dresser that they both shared and pulled out a clean pair of boxers. Winston averted his eyes to give his roommate some privacy, but glanced out of his peripheral vision as Havi turned his back to him and began drying his body with the towel. With Havi's back to him, Winston stole longer and more direct glances at Havi's toned back and sculpted ass cheeks. Then suddenly, Havi turned around, and for the first time Winston saw Havi's cock.

It was absolutely mouthwatering. Havi hadn't had any surgery, but what would have been a clitoris was a small, uncut cock about 3 inches long and thick protruding from a mound of dark hair. Havi used the towel to dry his chest and stomach. Winston's eyes followed Havi's hands as he pushed and pulled the towel lower and lower. Winston knew he was staring now, but he couldn't stop himself. He was so turned on and knew his cock was still at full attention and probably leaking a lot of precum.

"You gonna keep staring, or are you gonna do something about that boner?" Havi said, suddenly.

This shocked Winston out of his stupor.

"I know you've been staring at me," Havi said.

"Shit! I'm sorry Hav," Winston said, "I hope I didn't offend-"

"I'm not offended. I can tell you're curious, though." Havi said, "Go ahead... touch it."

Winston couldn't believe this was happening. He didn't hesitate or question. He removed the blankets and hopped off of the top bunk. He stepped closer to Havi and immediately had flashbacks to earlier that day in that bathroom with Jeff. This is how that encounter had started. Havi reached forward and grabbed Winston's hard cock through his sweatpants. Like Jeff had done earlier, Havi began massaging Winston's cock, caressing and stroking it.

"Damn, Win... you're hard as a rock" Havi said, "Go on, touch my Tdick."

So that's what it was, Winston thought. A Tdick. Now that he was closer to Havi, he could see it in all of its glory. Havi's Tdick was like a thick, and hard. Winston reached down and touched Havi's cock. Havi let out a gasp at the contact. Winston began to caress and jerk off Havi's Tdick.

"Fuuuck yeah, just like that," Havi encouraged.

The two men stood face to face jerking each other off, exchanging gasps and groans of pleasure. Winston's hand became slick as Havi got wetter and wetter the more he stroked Havi's dick. Winston knew that his own cock was leaking precum like crazy inside of his pants. He wanted to take them off but was too caught up in the heat with Havi's face just inches from his own.

"Fuck, I wanna suck you off" Havi said.

Havi dropped to his knees. Winston yanked off his sweatpants, his cock aching to be touched.

"Damn, Win! I didn't know you were packing like this!" Havi said, "I would have offered to blow you a long time ago."

Winston felt himself blushing.

"I guess... I didn't know you'd even be interested," Winston said.

"Well, I didn't know you were into guys," Havi said.

"I'm not," Winston said rather defensively, "I'm not gay."

"Bullshit!" Havi said with a smirk.

Before Winston could protest anymore, Havi took Winston's cock into his mouth. Winston let out an involuntary moan. Havi didn't waste any time and began sucking Winston's cock in long slurps, taking Winston's cock all the way down his throat. Winston couldn't believe he was yet again getting his cock sucked by another guy on the same day. Havi was much more ravenous than Jeff had been. He was deepthroating Winston's cock expertly causing him to moan uncontrollably as Havi's tight throat clinched around his cock. Winston threaded his fingers in Havi's hair and thrusted his hips to match the rhythm of Havi's sucking. Waves of pleasure radiated through his body as he fucked Havi's throat. Winston could hear the loud, wet clicking of his cock slamming in and out of Havi's throat. The wet mixture of Havi's saliva and Winston's precum made everything slippery yet tight. Winston knew he wasn't going to last long like this. Winston thrusted a few more times before he felt the unmistakable feeling of toppling over the edge.

"Holy shit! Fuuuuck! I'm gonna cum! I'm gonna-!" Winston moaned.

Havi sucked faster and Winston exploded. He saw stars as his whole body shook and spasmed. Winston felt several ropes of cum shooting from into Havi's mouth and Havi swallowed eagerly as Winston cried out. Winston thrusted as he rode out his orgasm, his hands still gripping Havi's hair. He kept thrusting as Havi kept sucking and swallowing. Winston squeezed his eyes shut and moaned and grunted primally until the last drops of his cum had been swallowed by his roommate. His legs were shaking when Havi backed off, letting Winston's cock plop out of his mouth.

Winston opened his eyes and Havi was still kneeling in front of him. Havi used the back of his hand to wipe his mouth clean.

"Wow!" Winston said, catching his breath, "You're really fucking good at that!"

Havi just smirked, clearly proud of himself.

"Yeah, it's one of my finer talents," Havi said.

Havi hopped to his feet. He was still completely nude. He walked over to his desk and sat on top of it facing Winston.

"Your turn," Havi said.

Winston froze. This hadn't happened earlier with Jeff. After Winston came, Jeff took off pretty fast and Winston didn't even have time to consider reciprocating. He looked at Havi. His legs were slightly spread and his hard Tdick was glistening from how wet he was. It's not that Winston was against sucking Havi's cock. He'd just never done anything like it before. He didn't want to be bad at it.

"Get over here and suck my cock already," Havi ordered, playfully.

"Uh... okay," Winston said, walking over to Havi, "I uh... I've never done this before."

"I figured as much," Havi said, "It's easy. It's just like any other cock. Suck it the same way you like for your own cock to be sucked."

Winston thought that seemed straight-forward enough. He kneeled down in front of Havi. He could feel his hands shaking as he placed each hand on Havi's thighs. He moved his face forward and closed his eyes. Havi smelled wonderful. He had a manly musk mixed with cologne and whatever soap he had used in the shower. Winston felt his lips graze the tip of Havi's cock. As soon as he felt Havi's cock on his tongue, he was a goner. Havi's cock was rock hard and the taste of his juices were wonderfully sweet and salty. Winston sucked Havi's cock slowly at first as he got acquainted with things. Then soon the mixture of Havi's smell and the taste of his juices swirled into an intoxicating tonic that Winston couldn't get enough of. He dove in, sucking Havi's cock with full force and vigor.

"Fuuuuck! Fuuuck yeah, suck my cock," Havi moaned.

Winston thought about the way Havi had sucked his cock. He'd sucked it in long, faster strokes, taking as much of it in his mouth each time. Winston replicated that, taking in all of Havi's cock until his nose was buried in the mound of hair surrounding Havi's Tdick. Then Winston sucked and slurped causing Havi to moan loudly.

"Grrrr! Fuuuuck yeah! Mmmmm!" Havi groaned and grunted.

Winston was lost in Havi's moans and he felt his own cock getting hard again. He was getting so turned on sucking Havi's cock and making the other man become so vocal. Winston slowed his sucking and eased up. He concentrated on the tip of Havi's Tdick and sucked softly.

"Ohhhhh! Fuuuck! Just like that!" Havi moaned.

Winston kept at it while reaching his hand down to stroke his own swollen cock. The feeling of stroking his cock and sucking Havi's while Havi moaned and grunted was almost too much for Winston to handle. Havi grabbed Winston's hair and started to grind his cock into Winston's mouth. Winston let Havi fuck his mouth while he pumped his own cock with his hand.

"Grrrr! Fuck! Fuck! Take my cock," Havi grunted.

Winston could hear his own muffled moans escaping his throat being man handled by Havi. Havi didn't let up. He kept grinding his cock harder and faster in and out of Winston's mouth. His moans and grunts were getting wilder and Winston jerked his own cock faster in response.

"Fuck yeah! Fuuuck! I'm cumming! Take my fucking cock!" Havi growled.

Havi cried out and shoved the length of his cock all the way into Winston's mouth until Winston's nose was pressed against his pelvis. Winston jerked his own cock even faster as Havi came hard in a shaking fit. Winston could taste a distinctly salty substance that was delicious and he sucked and licked eagerly to get it all. Just as Havi's orgasm was subsiding, Winston's cock exploded into his hand. He jerked it slowly while softly sucking the tip of Havi's cock. When Winston had shot the last of his load, Havi pushed Winston's head away softly.

"Okay, it's too sensitive now," Havi said.

Winston leaned back, and the two men just looked at each other in post orgasmic bliss while catching their breaths.