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This story involves consensual sex between two men. If you don't want to read about behavior of this type, look elsewhere. If you shouldn't read this for legal reasons or because you are deemed too young, go away.
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The Summer Associate
His hands pushed my head down. I resisted long enough to get a deep breath through my nose before I took his seven and a half inches completely into my throat. He gasped; obviously, no girl had ever been good enough to fully deep-throat him. I felt his body begin to tense -- he was getting close. I slipped a finger down from playing with his ever tightening ballsac to stroke across his pucking hole, damp with sweat. With a strangled cry, pleasure mingling with shock and a need to stay quiet, he flooded my throat with shot after shot of cum. I didn't even get to taste him. As his orgasm subsided, he released my head. I pulled back to get the very end of his load on my tongue. He shivered, and his leg involuntarily spasmed as I stimulated his oversensitive head.
I rose from my knees, standing over his seated form, slumped on the toilet seat in the bathroom we had snuck into. I took a few moments to look over him. He had the body of a high school athlete and frat bro, not quite working out as much as he once had. He was lean, with a musculature that showed a history of activity and care but a more recent history of other things getting in the way. The front of his polo was pulled up over his head, and his shorts and boxers were dropped to the floor around his ankles. His torso was pale, too little time in the sun this summer, although his lower arms and legs showed a golden chestnut hue. He had a cute outie belly button on his flat stomach. He had a wide nose and wide-set brown eyes. He was handsome in a douchey frat bro way. He was clean-shaven for the job, but I bet he usually had a mustache because he thought he looked cool. His overly coiffed, dirty blonde hair tried to compensate for the early receding hairline.
How had I ended up sucking off this straight guy in the bathroom next to my childhood bedroom? That is the story I'm here to tell you. Oh, and just to whet your appetite, his cumshot wasn't the end of our bathroom tryst.
A bit about me: at the time this occurred, I was 23, almost 24. It was the summer break before my senior year in college. I was old for my class. My mother had had cancer and died during my sophomore year of high school. (I'm not saying that to garner sympathy; it was sad, but it happened and is part of my history.) I repeated sophomore year at a new school the following year to make up for everything I missed. I also took a gap year between high school and going to university. I worked for the fall and spring, and I spent the winter traveling around Southeast Asia. My father had worked out of Singapore on a project for a few months that year, so I had a home base with him while I traveled.
My father was a partner in a boutique law firm, and my mother had been a high-powered consultant before she passed. We had plenty of money. But they both believed working was good for me. And I agreed. While I didn't know what I wanted to do with my life, I had no problem putting in the work to ensure a paycheck came my way.
That summer, I had gotten a job as a lifeguard at the local pool four mornings a week. It wasn't much, but it would hopefully cover books for the fall -- and kept my father off my back about doing something. He didn't know about my real job -- shaking my money maker to make money. I headed back to dance in a club near my college a few weekends throughout the summer. The tips from my three weekends of dancing were actually better than the paycheck from a whole summer of lifeguarding. Dancing was my primary income at school, even though I had a job shelving books in the library. Pleasure definitely sells better than safety.
So you can get a picture of me. I am about 6' 1" (185 cm for the rest of the world.) I am quite lean with what might be considered a dancer's body with a high, tight ass. My skin is a warm brown, darkened by mornings in the sun, both while lifeguarding and at the pool at our house. I am told that my age is ambiguous. I could be as young as my late teens or up into my thirties. My black hair was buzzed so short that I almost appeared shaven.
My father's firm was small -- much smaller than the firms that usually took summer associates. But it was quite well known and catered to celebrities and moguls. While most summer associates were working bitch hours for the promise of a job after graduation, the associates at my father's firm were working for something different. They were angling for a coveted recommendation. While it was out of my world, I understood that a recommendation from his firm was an entree to interviews for any job with other similar firms or in private lawyering for the rich and famous.
My father was responsible for the summer associate program this summer after the partner who had run it in the past was nominated for a judgeship. He always hoped that I would take an interest in following in his footsteps, so rather than asking his already busy administrative assistant or paralegals to help, he convinced the other partners to hire me as a glorified cruise director for the social events within the firm. It also gave me a regular paycheck in addition to the lifeguarding and dancing. Most of the summer consisted of planning several cocktail parties, luncheons, and dinners with the dual purpose of helping the partners get to know the associates better and grooming the proper etiquette and social skills into the associates. (They had a full-time lawyer whose actual job was organizing events with their clients, so I had nothing to do with that -- a strange way to use a law degree, but it worked for them.) But this afternoon was the final BBQ -- an informal event at the pool in our backyard. In fact, my father was the only partner there. This was a final opportunity to mingle for the associates, who, if everything went according to their desires, would be working together to help their clients, quietly, to bend the law to their whims. Yeah, a lot of the work was a bit sleezy -- but it paid very well.
So back to the story of my encounter with Dylan - for that was his name -- a perfect douchey frat bro name. Dylan was both exactly right and exactly wrong vibe for this event. Frat bro type. Bringing the mood of the party up, but also starting to get drunk -- not pleasantly tipsy, but drunk drunk.
I was having a lovely conversation with Miranda, another of the associates, when Dylan started to try to get people organized into some fratty drinking game. Flip cup, maybe? Whatever it was, he had totally missed the signals of proper decorum. I excused myself and walked over to where Dylan was trying to rally three of the other associates. While Dylan's social skills were strong, he didn't always have the best read of the situation. He had been good when the partners were present, but he struggled a bit more around a group of his peers.
I placed a hand on his lower back and leaned in to quietly state, "This isn't a frat party. Remember," I said, nodding toward the grill where my father was just finishing cooking sausages and steaks, "your boss is here too."
"Oh shit!" I could smell the beer on his breath, and his volume was a shade above where he probably thought it was. "Thanks."
Using my hand on his back, I steered him toward the cooler. The three associates he had been trying to harangue into drinking games nodded their thanks. I grabbed a seltzer and sat him down on a lounger to drink it.
I returned to my conversation with Miranda but kept an eye on Dylan. When he finished the seltzer, he got up and grabbed another beer. He bounced from group to group; from everyone's body language, I struggled to tell if he was being a social butterfly or getting the cold shoulder. I could at least tell from how everyone was reacting he had dropped the idea of drinking games. It wasn't a particularly large group of people, so soon enough, he had flitted Miranda and me.
To set the scene, it helps to know that Miranda was stunning -- long, silken black hair, curves for days, and big eyes that looked directly into your soul. Hell, I was a perfect Kinsey six, but she made me think about sliding down the scale some. But I was also the only one who knew that Amanda -- her blonde bombshell -- was waiting for her back in New Haven.
While Dylan's flirtations started as passably acceptable compliments, he soon stepped into inappropriate territory. While I knew Miranda could handle unwanted attention without an issue, it was my duty as the host to ensure she was having a pleasant time and that he didn't make too big of a fool of himself.
"I'm going to go finish getting the dessert trays together. Dylan, I could really use your help with that." Miranda looked at me with a question in her eyes: `Are you sure?' As much as I would have preferred to have Miranda come with me, this was the better solution. First, it would definitely separate them. He could follow if I asked her, but there was no way she'd make that choice. Second, it reminded him that she was not here to serve him. While I had heard from my father that Dylan was smart and was going to be a great lawyer, Miranda was on track for a clerkship at the Supreme Court. Just because she was a woman didn't mean she needed to do food prep.
While Dylan didn't look particularly happy to be redirected, he had enough sense to not make a scene. He had also been drinking this most recent beer much more slowly, and was sobering up a bit from his earlier drunkenness -- not a lot, but some. I led him behind the pool cabana, where we had a small prep room with a counter and refrigerator.
I busied myself with taking brownies and cookies and arranging them onto two platters. I occasionally asked him to help me grab something from the fridge, but most of the time, he just stood there. I got no help, but at least I had separated him from Miranda.
Suddenly, Dylan blurted out, "Rumor in the frat house was the gay guys give the best head." I wasn't sure if this was an attempt to connect with me or just to fill the awkward silence that had descended.
"Oh." I tried to remain neutral. I was torn. I didn't particularly want to have this conversation with him, but I was also morbidly curious to see where he would go with this topic.
"Yeah, that's what I've heard."
I could let it go here. But like a driver rubbernecking at a car crash, I needed to see how badly this went. I turned to face him. "Don't try to tell me you never got a blow job from a guy."
He looked shocked at the suggestion. "Well," he acquiesced. "One of the pledges during Hell Week had to give me a blow job. But he didn't know how not to use his teeth."
"Unfortunate." I didn't know exactly where this was going, but I was pretty sure I had a good idea of where he was headed in the end. And it was fun to see him on his back foot and scrambling.
"It is the second worst head I've ever gotten."
"Second?"
"The prissy chick who puked on my lap is number one."
"Oh, yeah, fair." I turned to keep working on laying out the various desserts on platters.
"Actually, my frat brother had a gay guy who sucked his dick whenever he wanted head. He said his mouth was so much better than his girl's. Whenever she wouldn't put out, he just called up this dude."
"And you never took advantage?"
"Nah. He wouldn't share. He wanted to brag about getting this guy to suck his cock, but he didn't want anyone to know who it actually was." He looked around the empty room and whispered, "Or for us to know how small his cock was. But we all already knew that."
"Oh..." I didn't know what else to say. "Well, I am pretty much done here. Thanks for your help." He hadn't done anything. I grabbed a bottle of water and handed it to him. "Don't forget to hydrate! Ok, everyone needs sweets. A host's job is never done!" I said with exaggerated cheer in my voice, picking up the platters.
"Um..." I could see him screwing up his courage for the question to come. "Will you give me a blow job? I have been away from my girl for two months, and I just..." Precisely as I guessed this would end up after his first comment about blowjobs. And I had already decided my path forward.
I cut him off, "On three conditions, no... wait -- four." His mouth snapped closed. "First, you never tell my father or any of the summer associates."
"No problem, trust me."
"And no bragging to the frat bros."
"I wouldn't tell a soul."
"Two, I am in charge. You let me do my thing. You don't get to tell me how to do something you don't know how to do. I've been on both ends of more blow jobs than you have ever dreamed of."
"OK."
"Three, you get me off too, including at least a little sucking." His eyes bugged out. I turned and started to walk away. "Oh, and four, I don't want to hear about your girlfriend. At all. Let me know if that works for you." I walked out of the cabana. "Bring that tray when you come along."
Dylan followed a few minutes later, a stunned look still plastered on his face. I knew my gamble had paid off no matter what direction this went. If he accepted, I'd get to blow a hot dude -- for he was hot -- and get my rocks off as well. If not, I had thrown him for a loop, and he would be good for the rest of the party.
I watched as Dylan tried to reintegrate into the party. But I could see his mind turning. He kept trying to surreptitiously look in my direction -- checking me out. After about fifteen minutes, one of the members of the group he was talking to stepped inside. Almost immediately, Dylan walked over to me.
"Excuse me, Ryan just went to use the restroom, and I was wondering if you had another one that I could use."
"Of course, if you go through the foyer and down the hallway on the left, it is the last door on the right." I knew exactly what he was going for, but I had to make this at least a little bit difficult for him.
"Um... could you show me? I don't want to get lost and end up in the boss's bedroom."
Surprisingly smooth, actually, I was somewhat impressed. "Sure, this way."
As we turned the corner and no one from the pool area could see us anymore, Dylan whispered, "Ok."
I stopped and turned to him. "Ok, what?" I decided to make him say it. I knew I was walking a fine line, but I didn't want to make it look like I opened wide for any sexy guy who propositioned me -- even if I did.
"Uh, I agree."
"To what exactly?"
"Your conditions for a blow job."
"Meaning?"
"Are you going to make me say it?"
"That you'll suck me if I give you a blow job?"
Dylan looked around nervously. "Yeah, that."
Good enough. That was about as much as I was going to get out of him. I started down the hall, leading him to the bathroom he had asked for.
When we both were in the bathroom, and I had closed and locked the door, I took steps forward, slowly forcing him backward until he ran into the vanity counter. Unable to back up anymore, he arched away from me. His polo had ridden up slightly; I let a finger rest on the waistband of his boxers.
"Are you sure you want this?" This was an interesting moment. I got to ask for consent and tease my horny little frat bro all at the same time.
Dylan nodded, leaning forward toward me, finding a bit of confidence--his lusty need for release suppressing all else in his brain.
"And you agree to my four conditions?" He nodded. "Including getting me off." He swallowed and nodded again. "Using your mouth?" His eyes got wide, and I could see him fighting the urge to lean away. While there may have been questions, the haze of lust pushed them all aside. He nodded one last time. Privately, I knew that he might not follow through after he came, but even if he didn't, watching him squirm in this moment made it worth it. And hell, who was I to say no to giving a hot guy a little pleasure?
Sliding my hands up his torso, I slipped the hem of Dylan's shirt over his head. I left his arms in the shirt so it stayed on -- bolero-esque, but exposed most of his torso to me.
My hands caressed back down his torso. He was in good shape -- a combination of good jeans, a strong athletic history, and occasional trips to the gym. His nipples were small, rose-pink nubs, already tight on his square pecs. A quick brush over them let me know that he knew how sensitive nipples could be.
Soon, my hands arrived at his waistband. I hooked both fingers in and spun him so he stood in front of the toilet. This boy didn't know what was about to hit him, and there was no way that I was going to try to hold him up as he was cumming. So lying on the bathroom floor or sitting on the toilet were the two options, and the floor was simply not going to be comfortable. If my room had not had picture windows overlooking the pool, I might have considered taking him there. But we would have to make do.
I slid one hand inside his underwear and around his hip, stroking the smooth, hidden flesh. My other hand moved down over the front of his shorts, coming to rest, cupping his privates. He tensed at my touch.
"Last chance to back out," I offered. But his cock was hard in my hand. I knew what his answer was.
"Pleeaassseee," his hissing whisper was a plea and an acceptance and pushing his cock into my hand.
I jumped into action. In a surprise attack, I swiftly had his pants and boxers around his ankles and his butt on the toilet lid. (Don't worry, I like to get freaky... but an open toilet isn't my kinda freaky.) I was kneeling between his legs.
I knew this needed to be quick. I was the host and could disappear for too long, and, for his sake, I didn't want it to be too apparent that we were both gone at the same time. But I wasn't too worried. As he said, it had been two months, and frankly, he had never had a decent blow job. With my skills, if this took more than five minutes, I would consider it a fail.
Before I started, I took a moment to look at the prize before me. It was somewhat annoyingly beautiful -- seven and a half straight inches, clean with one pronounced vein. His pubic hair was perfect and obviously not trimmed. How did a douche end up with such perfection between his legs?
Leaning forward, I started to work hard to give Dylan pleasure. I took pride in my skills and wanted to prove his original statement, the frat house rumor, true -- gay guys give better head than girls.
It was too bad that this had to be a rush job. I could have had some fun with him and his too perfect cock. Sadly for me -- but thankfully for the clock -- Dylan was already pretty close to the tipping point. I didn't even have to bust out most of my tricks, just the basic techniques got him right to the edge.
At first, he was kind of frozen, the proverbial dead fish. However, as he got closer, he started to participate more. His hands came to the back of my head, and he began to thrust up into my mouth. I was careful not to let him too far into my mouth. I wanted to save that to push him over the edge. Unfortunately, I didn't get a chance to get his balls in my mouth. They were as pretty as his cock. I did get them in my hand, though. They were the perfect size to hold both in one hand and play with them. His sack was also big and loose enough to provide what could have been a lovely mouthful of testicle. But I had to be satisfied with simply tugging and rolling.
Soon enough, three and a half minutes maximum, his balls began to tighten in my hand, and his thrusts became more insistent. It was time to push him over the edge. With a deep breath, I dropped my head down fully, opening my throat and wrapping my lips around the base of his cock. At the same time, my hand slid down from his balls, and my middle finger slipped into his sweaty crack. I found his tight rosebud and stroked it -- not trying to enter him, but just to provide pressure and stimulation. This double sensual assault was all it took to push him over the edge. Thrusting up and pinning my head down, he let out a strangled yelp and lost himself in the waves of cum flooding out of his cock and down my throat.
As soon as I could, I pulled up. I wanted to get at least a bit of his cum in my mouth so I could taste him. I teased the sensitive head of his cock for a bit until I had sucked every last drop of his cum out of him.
After Dylan shot his load down my throat, I stood in front of him. I dropped my trunks to the floor. This left me in just my usual home swimwear, a white speedo. I liked the way that the bright white contrasted with my brown skin -- and how it became sheer when I got out of the pool. Although no one got to see it, it made me feel sexy.
I pulled the waistband of the speedo down over my cock and hooked it behind my balls. My almost nine inch cock popped out and pointed at Dylan. "Your turn."
Dylan's eyes widened at the sight of my cock. I am used to guys' eyes widening. Most of my hookups are excited when they see my cock for the first time. But Dylan's eye-widening was a bit different -- a combination of surprise to see another man's hard cock, trepidation about what he knew was coming, and fear at the size of it. But mostly, he was mesmerized by the bobbing pulse as it reached out for him.
Slowly, as if by enchantment, Dylan stood and took two steps to close the distance, stepping out of his shorts and underwear. Dropping to his knees before me, he reached out to touch my cock. As his hand wrapped around my shaft, a quiet "shit" slipped from his lips. His hand was surprisingly soft. He started to rub my cock.
As he jacked me off, I placed a hand on the back of his head. Carefully, I steered his face closer to my cock. Dylan looked up at me with concern in his eyes. "Start with a lick." Dylan never took his eyes off of mine as he stopped his hand and reached out gently with his tongue. The moist surface lightly touched my tip before retreating back into his mouth. With eyes still locked, I gave him a disapproving look. He knew. One touch of the tongue did not fulfill his obligation. His tongue slid back out and swiped across the head of my cock. Again, it retreated, but this time, eyes held a different look. I could see his tongue moving inside his mouth as he knelt at my feet, holding my cock. He was tasting me. Soon, his tongue emerged again, and he started lapping at the bulbous head of my cock.
"Now put your lips on it." He moved forward slightly and placed his lips on the tip like he was giving it a chaste kiss. His eyes had tried to focus down on what he was doing. I put a bit of pressure on the back of his head. Not enough to make him do anything, but a suggestion and encouragement to move a bit further.
Dylan's eyes flicked back up to mine. He slowly moved his head forward, parting his lips and taking the head of my cock into his mouth. Soon his lips were wrapped around the very top of my shaft. His teeth lightly scraped the flared edge of the crown, and I jerked back, pulling out of his mouth. My cock left his lips with a loud pop. He looked up in shock.
"Careful with the teeth."
"Sorry." His look of contrition was authentic. Even if he didn't exactly want to be giving a blow job, he knew from experience what teeth on a cock felt like.
"Wrap your lips in to cover your teeth."
With a funny exaggerated motion, Dylan did exactly that and returned my cock head to his mouth. If nothing else, he was a man of honor and was going to do what he had promised -- what I had earned with my cock sucking skills.
Dylan started to literally suck on my cock like it was a straw. He began to move his hand back and forth again. Although by no means a good blow job, it was oddly erotic. "Why don't you use your tongue too." Immediately at my suggestion, Dylan started to lick at the head of my cock in his mouth. He struggled to coordinate the tongue actions with his jacking, only managing to handle one action at a time. It was almost comical, but I knew laughing would injure the fragile manhood he clutched.
Suddenly, Dylan tried to push himself down on my shaft. He only got another inch or so in before he started to gag. He tried to push through but just couldn't. He pulled back, coughing, with drool dripping from the corners of his mouth. I waited to see what would happen next. He caught his breath and dove right back in, trying to prove a point. Unfortunately for him, he failed in that endeavor. He got less than half my cock into his throat before retching and pulling back - and I think he achieved the extra inch mainly by the initial momentum.
As he knelt before me, panting, spit dripping to his chin, I felt an odd combination of emotions. Pity was not quite right, empathy, maybe? He had tried but failed. Something I don't think happened to him very often. I was also strangely proud of him. I had no right to feel pride, but he was trying and doing so mostly willingly. (I mean, he wouldn't have chosen to give a blow job, but he wasn't complaining and was trying his best.) If he were a gayby -- rather than a horny straight boy -- I would have shifted us to the bedroom and found some erotic release through frontage or something similar. But this was not about teaching him, this was about getting off.
"You don't have to deepthroat me."
"But you did," he panted.
I smiled. His conviction and sense of fair play were cute. "Let's just say I have a tad bit more practice." I wanted to kiss him in that moment, but that wasn't part of this deal. "Why don't you stand up?" Dylan complied. I grabbed his hand and, spinning halfway around, turned so my back was to him.
Dylan wrapped his hand back around my cock. He started to jack me off slowly. I could tell from the confidence in his actions that he was much more practiced in masturbation from this angle. Using his spit as lube, Dylan started to work my cock with seasoned motions. His left hand slid around my waist and began to lightly trace along my abs. We were of a height, and I could see him watching his hand caress my body in the mirror. He had a slightly glazed look like he was detached, watching his hand move from a different body. Soon, he found his way up to my nipple. As he pinched lightly, I arched back into him, gasping. Our bodies pressed together; Dylan pulling me in tight. I don't know if he meant to pull me in, but our eyes met in the mirror, and I watched him decide to keep holding me against him.
My hips shifted back, and I felt his cock nestle between my ass cheeks. Soon, he was hard once again and sliding his erection up and down my crack. While he gave a shitty blow job, he was a natural at giving a hand job.
I could feel myself getting close. Our eyes locked in the mirror, and without breaking eye contact, Dylan leaned in and nibbled on my ear lobe. That small moment of unexpected intimacy was enough; the wave was about to crash.
Spinning out of his grasp, I pushed down on his shoulder. Dylan, surprised by the sudden action, dropped to his knees before me. I wrapped my left fingers in his hair, pulling his mouth back to my cock. Instinctively, Dylan covered his teeth as he sucked the head into his mouth. He had learned. Impressive. I held him there, jacking myself off with his lips wrapped around the end of my cock. As I got closer, Dylan started to work his tongue along the sensitive bottom of the tip. That bit of stimulation was enough. As my orgasm hit, I had just enough control to yank his head back. My first shot splashed across his forehead, and the next two streaked across his face.
It took me a minute to regain my composure and legs. Once I was steady, I let go of Dylan's hair. I looked down at the handsome frat bro law student kneeling in front of me.
Dylan didn't know how to feel. The confusion was clearly comprehensible on his features -- right alongside my cum. He had just sucked a guy off and then taken several cum shots across his face. And he didn't hate it -- maybe even liked it. His cock was still rock hard, sticking out in front of him.
I tucked my cock back into my speedo and pulled my trunks up over that. I patted Dylan on the head, gently stroking his hair back into place, and leaned down to whisper, "Not bad for a newbie. With a little practice, you could be pretty damn good at that. I'm going to head back to the pool, but you might want to take a few minutes to clean up." I gently kissed his cheek where I hadn't cum. I turned and started to walk to the door. I had a wicked idea. Turning back toward him, I offered, "Oh, and when you're ready to find out why gay guys like to get fucked in the ass, let me know. I'm a good teacher." I winked and left him mostly nude, kneeling in my childhood bathroom.