- Gay Male
- First Experience with Another Man
Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here
It was when we were visiting my brother and his wife at their South Carolina beach house, last spring, that I had my first experience with another man. You'll have to decide for yourself what "category" this episode fits into. To this day, I am not sure myself what I would call it.
I play tennis quite a bit at home, and there was a tennis club that was part of my brother's resort neighborhood. I added my name to a doubles signup list in the hopes I might be able to play some competitive tennis during my visit. The second day I was there I got a call from the club indicating that a group needed a forth that afternoon.
I changed into my tennis shorts and shirt and went over to the tennis club house just before 2:00. I parked and went into the pro shop and the employee there told me my group was already down on court #3.
As I approached the court, I could see the other 3 guys were already warming up. From my quick observation, they appeared to be good players, so it should be a good match. All the other players looked to be somewhat older than me, which probably put them in their 50's. My partner for the day was well tanned, indicating he probably played frequently. We made short introductions. My partner's name was Mike and he told me he and his wife were staying at a nearby condo for the month.
It was a beautiful warm sunny afternoon. Perfect for tennis. Mike and I seemed well partnered on the tennis court, me being somewhat more nimble in the back court and him with an aggressive net game.
We played for about 2 hours and ended up beating our opponents fairly convincingly. As we wrapped up our play and put away our rackets, Mike asked me if I'd like to join him for a cold beer at his condo, which was just a few steps away from the tennis complex. It sounded good, so after leaving my equipment in my car, we walked over to his place.
Mike grabbed a couple of cold beers from the fridge and we sat down on the couch. We had both worked up a sweat, so sitting back with a cold one hit the spot. Mike said his wife and he had come down here the past few years and really enjoyed it. She was out shopping for the afternoon.
As we sipped our beers we both talked a little bit about where we were from what we do for a living. Other than being a talented tennis player, there was nothing particularly remarkable that I noticed about Mike. He had a couple of grown kids. He was about 6 foot tall, well-tanned, and in average shape. My kids were somewhat younger. Even at 42, I've always had a slim athletic physique, stand about 5'10" and weight in at 150. I am sure my tennis play contributes to my staying in shape.
After my first beer I needed to use the bathroom. As I got up off the couch, I could feel that my left hip and leg had really stiffened up on me. I remarked to Mike that I should probably have stretched out some after our match. I hobbled to the bathroom to relieve myself of the beer I had been consuming.
I came back to the living room, and my stiffness had improved but was apparently still evident. Mike commented on it and asked me if the soreness often happened after I played tennis.
Mike commented, "You ran around that court like a jack rabbit, so I am not surprised that your muscles have tightened up on you some."
''Well I'm getting old, so it happens to me sometimes, but it will probably get better in an hour," I replied.
"Do you want me to take a look? I did some sport medicine classes in college and am pretty good at evaluating these situations," Mike offered.
"Well, I think I will be fine in a little bit, but if you have some ideas on treating it, I'm all ears," I said.
"Come stand in front of me, facing the other way. It's on the left side?"
I hobbled over in front of Mike, who was still sitting on the couch, turning my backside to him.
"Point to where it's tight," he said.
I pointed to my left hip and to the group of leg muscles just below my butt. With a surprisingly firm touch Mike probed the tight area with his hands. It felt good but a little painful at the same time.
Mike exclaimed, "Yes, both those areas feel somewhat knotted up. I think I can work the tightness out if you'll let me."
It certainly felt like Mike knew what he was doing. "If it's not a problem, I think that would be great Mike."
"Let me drop your shorts, so they're out of the way." Without waiting for an answer, I felt Mike pull on my tennis shorts, which easily stretched over my hips and fell to the floor. I was left standing in my white underwear and tennis shirt.
I was slightly shocked, but didn't say anything to Mike. He returned to massaging my upper left leg with his firm touch. He first pressed his palms and then his thumbs into the knotted areas. He used both hands which wrapped themselves more than half way around my upper leg. He was so far up my leg that I could feel the top of his inside hand coming into incidental contact with my sac. Though underwear separated me from coming into direct contact with his fingers, the grazing sent a small tingle through my body.
"I can feel the knots loosening up," Mike proclaimed.
"Yes, I think you're right."
"Your tennis shirt is petty long, why don't you take it off so it doesn't get in the way when I am working on your hip."
In retrospect, Mike's seduction was so obvious, that an idiot should have seen right through it. But, Mike had gotten me to a state where, in my mind, I was just complying with the "doctor's" orders and he was indeed brining needed relief to my sore body. I dutifully pulled my sweaty tennis shirt over my head and placed it on the floor.
Next, Mike started in on my left hip. Again firmly kneading it with both hands. After a short while his hands starting going a little off target as he massaged all of my ass. It felt good and I stood in silence as he worked my glutes with his hands.
"I am sure you've heard this before, but you have a great ass," Mike off handedly commented, like he was talking about the weather.
While I thought my ass was one of my best features, and had been complimented on it on more than a few occasions, those observations had never come from a guy, much less one that currently had both of his hand on it. I am sure I turned a shade of red. I just let the comment pass, not knowing how to respond to his compliment.
We continued my therapy as he thoroughly worked my hip and ass muscles over. The silence was broken, when he instructed me to turn back around. I obediently complied. Here I was in some guy's condo, I had met 3 hours ago, wearing nothing but my underwear, and doing whatever he asked me. Mike started in massaging my leg from the front. I stared down at his hands as they worked their way up my leg. The obvious was finally starting to dawn on me. Mike's touches were becoming less and less therapeutic and more, for lack of a better term, sensual. I could tell that he was enjoying touching my body. In my mind I was thinking to myself, "but this guy is married!"
I have to admit, I didn't dislike the attention Mike was paying me. I could have walked away at any time, but I didn't. I was actually beginning wonder just how far this "therapy session" would go, if I let it.
As his hand worked steadily up my leg, I could feel myself begin to stir. He pressed into the top of my leg and groin, just an inches from my growing cock. One of his fingers lightly traced the elastic leg openings of my shorts and lightly scratched at my ball sac. He moved his hands to my other leg and repeated the process. By the time his hands moved to the top of my other leg, I could feel my cock rapidly hardening. I wondered where his hands might go next and I stared down at myself and watch my hard-on fill out the front of my shorts. I hardly noticed when Mike began to tug on my shorts. As they were lowered, my hard member sprung free. Both of us watched it bob about for a few moments before stopping at its flag pole position.
"Very nice," I heard Mike exclaim. I'm like, did someone just compliment my package? Before I could react or say anything, he leaned forward and engulfed my proud boner with his mouth. I practically gasped for air as he swallowed my cock. This was nothing like my wife's occasional and tentative oral attentions.
I felt him cup my balls as he bobbed up and down on me.
"Doesn't that feel good?" Mike asked.
A soft moan was all I could give him in reply.
"When you walked out onto that court this afternoon, I said to myself, I'll bet that guy has a cock that is just perfect for sucking and I was right. I love my wife, but sometimes I see a guy and I just need to suck cock."
I wasn't sure what to make of his "confession", but here I was, enjoying the benefits of his obsession. Mike was working my cock like someone who was starving. Fortunately, Mike backed off a little, allowing me to cool down some. He explored my length with his hands and licked the underside of my erection with his tongue. He took just the tip into his mouth this time and swirled his tongue over my cock head and then without warning his mouth swallowed me whole again, causing me to moan once again.
I never cum when my wife performs oral on me. It is enjoyable, but simply is not stimulating enough to bring me to the edge. This was different. My whole penis tingled every time Mike plunged his mouth over my length, milking me with his throat. I was just getting to that point where I knew there would be no holding myself back. Mike seemed to sense that and backed off me.
His hands explored me more extensively, running over my abs and chest. Then down between my legs and behind my sac. Reaching further back, he ran his fingers over my ass and lightly probed between my cheeks. Meanwhile I just stood there, taking it all in, with my rock hard cock pointing at the ceiling. Soon he returned his concentration back to the part of my body most in need of attention. Using both his hands and wet mouth he rapidly bobbed up and down on my pole. Sensations built quickly as he relentlessly slurped, fondled and beat me off. I knew I was close.
I told Mike, "I'm going to cum!" and started to pull back some.
Mike reacted by wrapped his hands around my ass and pulling me deeper into his mouth. Instead of passively standing by as he sucked me, I began to thrust my hips as I anticipated my impending climax. I could literally feel my toes curl as my orgasm began to come over me. My cock was slammed as far back as it could go as I began to ejaculate. I am sure he could feel cum spay the back of his throat. I continued to unleash my seed down his greedy mouth. Finally I pulled away, as I was too sensitive to continue.
Mike exclaimed "So has the stiffness gone away?"
"Do you mean from my leg or my cock? Yes to both..." I said.
- COMMENTS
Anonymous3 months agoLiked it. My first time, I was 17 and working at McDonalds. This guy came in said hello. Asked me my name and ordered a coke. He was much older than me probably in his early 40s but a good looking guy and looked to be in great shape He said that he would pull around to the drive in window and order a burger and would like me to go to the window and wait on him. I thought this was really strange and I kind of had a feeling that he was coming on to me. I had only had a couple sexual experiences both with girls, and had never thought about anything with men. I traded places with the guy that was at the window and the man had placed and paid for a Big Mac so he pulled up.to the window. I started to hand the hamburger down to him and he said what do you think of this? I couldn’t believe it. He had his cock out and it was large and very hard. I didn’t say anything and he said, how would you like to touch this I still didn’t answer and he asked me what time I got off work. I told him in about an hour. He said he would be out in the back in the parking lot and would wait for me if I decided to see more. He pulled out, and I kind of stood their stunned. I asked the manager for a toilet break. I stood in the bathroom thinking about that big beautiful cock and got an erection. As I waited for the end of the shift, I kept going back-and-forth in my mind, whether I really wanted to do this or not and I obviously wasn’t sure what it was we were gonna do. Finally, I walked out the front door and circled back to the back of the parking lot, He was standing outside of his car and I walked up to him. He asked me if I’d ever been with a man before and I told him I had not, and had really never thought about gay sex. Then he said I’ll give you $50 bucks and guarantee you’re going to enjoy yourself and I won’t do anything that you don’t want to do. He said just get in the car and we would drive about half a mile away where there was a local park. I really needed money and I told myself screw it for $50 bucks what have I got to lose? I got in his car and he immediately handed me $50 which I put in my wallet we then drove to the park and there was a big restroom there that was lit up and he said we’re going to go in there. We went in the restroom and there was no one there, he obviously had been there before because he locked the door and said nobody can get in now until we unlock it. He then proceeded to takeoff all his clothes and put them on a bench. He asked me to get undressed, and I told him I was really nervous so he walked over and gently pulled off my shirt and buckle my pants and I kicked off my shoes. I got a nice package about 7 inches with a big set of balls. Without saying a word, he put his hand underneath my balls and massage them. He put his hand on my cock and put it in his mouth while milking my balls. It all happened so fast I was kinda in shock. This was the first blowjob I’ve ever had and it felt unbelievable and I started moaning and I couldn’t stop. He was really given my cock a world-class workout. I’ve had a lot of blowjobs since then, but I don’t remember any of them being any better than this one. While he was sucking my dick, he took his hand and started rubbing my ass and gently inserted a finger in my virgin ass. Even today 20 years later, I can remember the ecstasy that I was in. I never even thought about something being this good. I didn’t know whether I was supposed to cum or not. He said slow down. I want you to try something. Then he stood up and rubbed his stiff cock on my face. I couldn’t believe it, but I grabbed it and put it in my mouth. He told me to watch the teeth and then instructed me on what to do. I knew then this wasn’t gonna be the last cock I’ve ever sucked. It felt fantastic. Then he began to fuck my mouth harder and faster, his cock began to twitch, and I knew instinctively that he was going to come. He did, and I took it all in the back of my throat, but some of it came out and dripped out of my chin. I stood up and he got back down on his knees and began to really suck. My cock and I came so hard I almost passed out. We both got dressed quickly and he said would you like to do this again and I said hell yes. He asked me what nights I worked and I told him and he said he’d be back in the next time he would bring some condoms for a little ass fun. He came to McDonald’s every week for the next six weeks before I went back to school.. he taught me everything he knew, and we had some long sex sessions. I found out that he was married, which really didn’t bother me. Needless to say after those six weeks I realized I was totally gay and I never went back to even thinking about girls. You never forget the first time, and I will be forever grateful for the guy for teaching me what to do. Ps, he always gave me $50 which I appreciated but of course it made me a gay whore!!
imrdy2almost 6 years agoI was hitchhiking to LA to visit some friends. I was 19 A large truck stopped and offered me a ride, I hooped in. A large burly man at the wheel, a bear type. He asked where I was going and what I planned to do, just small talk. We soon arrived at the top of the ridge route and He wanted to check his brakes before we started down the hill. When he go back in the truck he did not start the truck and said he needed a little brake. As we sat there he started to ask me if I had ever fuck a girl. Where did I go to get blow jobs. Some what uncomfortable I said yes. He wanted to know all about it and I made up some stuff that excited him but that was not my intention. Soon he ask if I had ever had a blow job by a man. I said no. He said "you want one?" Not answering him, he put his hand was on my thigh. He asked if that made me uncomfortable. "A little" was my answer. He put his head in my crotch and unzipped my pants. I was for sure hard. He started to suck me off. He said let's jump in the sleeper, it will be more comfortable. He was large man and I felt It was best to do what he wanted. Besides he was insisting and basically pull me into the sleeper. He removed my pants and in a quick move had me face down in the sleeper and put his weight on me to keep my there. He removed his pants while keeping me in place. Once his pants were off he slid along side me with his very thick cock basically in my face. Suck it he commanded. I had no choice I had to open wide and take it all in. This was a first I had never though I would do this but I was afraid basically. He love it, said "your a natural cocksucker" Soon he was fingering my ass and wow I knew what was coming next. No doubt. He slid back and was rubbing my crack with his very thick cock. I knew that he was going to fuck me. Then he said "I'm going to fuck you boy" don't fight it jus relax and let me cum and we will be on our way. He began by fingering my hole and lubing it. Slowly he put the head in a few inches then stopped for a moment and pushed a few more. Once all the way in he began to pump slowly and then faster. As he lay on me he kept saying that I was his whore and deserved to be fucked. That was strange I didn't even know him! He was going to cum I could tell my his breathing and then he loudly came in me as he pumped me faster and faster.....it was over. I was worried, am I now gay. Would I do it again? I seemed to like it in my mouth and once he got his going it felt ok. He dropped me off and went on his way. Walking a short distance a truck stopped and wave me over. You want a ride son.
Anonymousabout 6 years agoWhen I was 17 at the house of the company owner, in his pool, I was seduced for the first time by a man. He was nearly 55, a large, hairy man. Me, young, skinny & naïve. He dunked me and as I was trying to get away, he grabbed my trunks & pulled them down. He pulled me into him and put his big hand on my small, soft penis. "Mmm" he said as he played with it. "Um, Mr. West, I... um..." I broke away & said "Gotta go to the bathroom, where...?" ""Upstairs, down the hall on the left." There were about 8 others in and around the pool as this was a company party. I was shaking as I peed, wondering what the hell just happened & if anyone saw him touch me. Mid way through relieving myself, the door opened, I looked over my shoulder & watched him shut & lock it. He pulled his trunks off, stepped behind me and pulled mine to my feet. "Mr. West! um, what? what are you doing?" "Mmm beautiful ass Jim, just let me play, I won't hurt you." He rubbed my butt cheeks, squeezing them as I finished peeing, then he reached around and took my tiny little wiener between his thumb & forefinger. He wiggled it, I moaned as the last droplets fell from the tip. His left hand pushed my back down and I felt his breath on my butt. I looked between my legs and trembled as I watched him stick out his tongue. He put it between my cheeks, let go of my weenie, pulled them apart and I felt the warmth of it on my butthole. "Mmm, you taste good Jimmy, love your tight little butt hole." I was shocked, but it felt so good, my body started to tingle. Never even touched myself back there, except to wipe, so I was amazed it felt so good. He licked mw like that for five minutes or so, then I heard him grunt as I looked under me, I could see he was standing behind me. I felt something warm touch my hole, soft, wet and warm. He rubbed his fat penis all around my bung hole. Was he trying to put it in me? He grunted again and moaned "I'm cumming!" I felt hot liquid hitting my butt hole & onto my lower back, then running down it. He immediately went to his knees and Licked up all him sperm from my butt, balls and what dripped onto the floor. My little weenie was hard now, but I felt weird, confused. A "man" had just cum on me! On his knees, he turned me around and took my hard little three inch penis into his mouth and slowly, passionately, made love to it, moaning the whole time. In less than a minute, I said "Mr. West, um... I'm oh! I'm cumming!" He moaned with me in his mouth and sucked me faster, taking all three inches of me into his mouth, and let me cum! He kept me there, moaning and sucking and licking me. I stayed hard (youth!). He kept sucking me as he placed his hand around and held my butt, then put his fingers in my crack, searching once again for my hole. Once he found it, he pushed a fingertip in and I came again, in this man's mouth! He seemed to like it. I pulled away, closed the toilet lid & sat, exhausted, satisfied. He walked to me, bent down and kissed me. I felt his tongue try to enter and opened my mouth. He pushed a mouthful of cum into my mouth, then kissed me deeper, sucking and licking it all back into his mouth.
There were more times at his house, if interested - brownibleu44@yah...
