This is a detailed description of my first time. It is written as close as possible to the actual events. There is no piece of fiction in it, this has happened exactly like it writted down here. No fantasy, just facts. responses, comments and questions welcome.
I realized that I was turned on by other boys when I was about 15. But jerking off side by side to my best friend from school was the closest to a sexual experience that I could get. Once I tried to trick him into sucking his cock, but in the moment he realized what I was up to, he stopped me and became serious about our little games. He told me that sucking would be too gay for him, and that day we ended anything sexual in our friendship. Somehow we managed to stay friends; later he would even be the first to know that I actually was seriously gay. But before that I had the urge to do something seriously gay.
After losing my jack-off buddy, I was -- like any male between 14 and 18 -- in desperate need of sexual encounters. Basically, sex was only thing I was thinking about. I needed sex, gay at best, but anything else would be welcome, too.
It took a soccer-accident to give me a kick-start. An injured ankle forced me to staying in bed for about two weeks, not long before I was turning seventeen. My parents supplied me with the necessary news and entertainment, comic books, newspapers and magazines -- since I refused watching television. I had a lot to read. And that particular Issue of the TimeOut that my parents bought for me that week was "the big gay special issue". I don't know if they had looked at the cover before, but if they had, they sure wouldn't have minded. They are very liberal, and I know they are happy to have a gay son that does not watch too much television.
Anyway, I studied this piece of paper intensively for a whole week, I read about every detail of gay life in my city, including sex-facts and health-issues. The moment I was able to walk again, I was up for something. And I was well prepared.
One Friday night I told my parents that I would be hanging out at a friend's place and it might get pretty late that night. Instead, I took the subway to one of the gay bars that I read about. I had a long time choosing which place would be the best for a 16-3/4 year-old to get in contact with some decent gay man. I was not sure if I was looking for a boy of my age or a grown up, and I didn't mind. I was out to have any kind of sex.
The bar of my choice proved to be a comfortable, but totally boring place. Well, any bar is boring before midnight, but I had no choice. I needed to get back to my parents home with the last train, and that train was running about midnight.
So what happened when I entered the bar? Of course I was the centre of attention, because I was by far the youngest guest. And my looks were quite alright. I ordered a drink, a coke; I didn't want to push my luck. It was illegal enough to keep me in the bar and not having me kicked out, but beer would have gone too far. So I stuck with a non-alcoholic drink and sat down on a chair next to the bar.
Next to me sat two guys about thirty years old, a bit nerdy, but instantly friendly. One of them was the good looking shy guy; the other one was geekier, but also more aggressive. They looked like a couple to me. I was happy to have some nice conversation, and I was happy not to have ended up in a place for total sex-pigs or even worse, total hipsters.
The two guys were asking many questions about my life: If I was gay at all, if I wanted a boyfriend, what kind of experience I had, and so on and so on. The conversation took a new direction when I said:
"I am basically looking for my first time gay sex; I want someone to try out these things with".
They were stunned.
"Actually, we are not a couple" was the first thing that aggressive geeky guy replied.
And this is how it went. Geeky guy suddenly realized that he had the chance to show the world of gay sex to a horny teen. While shy guy was focussing his attention on another guest in the bar, geeky guy tried to persuade me to come home with him that night.
"If you want it, you can have it tonight. I will suck your cock all night" he said.
"I want it, but I have to be home in an hour or my parents will become suspicious." I said.
"But you can sneak in tomorrow morning, and they won't notice a thing."
"I want this very bad, but if we do it tonight it will go wrong. If you want this as much as I do, then trust me, let's do it when we have enough time and I have a good excuse to stay away from home for a day, or something like that."
"Then give me your telephone number."
"I give you my number, but this is my parents' house, we have only one number. Don't call me! Give me your number and I will call you, promise."
"Okay. Call me on tomorrow."
"Okay. I will."
This is how my first night in a gay bar ended. I got my train back home, horny as hell, my cock rock hard, precum leaking into my underpants, thinking about what I just missed tonight. I was angry about having to go home, I could have been in sexual ecstasy that very moment, having my cock sucked - or even more. Instead of that I was sitting on a subway train, my cock pressing against my belt, my balls aching to get off.
When I got home went to bed I jerked off and shot my load against the wall behind the headboard of my bed. It was definitely time.
I called Tom -- that's his name -- the next day like I promised.
"Hi, I'm glad you called."
"Hi! And I have a plan."
"That's good, what's you plan then?"
"I just told my parents that I will be on a bike tour with friends all day long tomorrow."
"So you can stay away without any risk?"
"Yeah"
"So I will see you tomorrow. Will you be here for a late Sunday breakfast?"
"That sounds alright, where do you live?"
Tom told me his address and we said goodbye, me hard and horny just thinking of what might happen the next day.
When I got to Toms place the next morning he waited on the doorstep of the house his flat was in. He was 30 Years old, definitely taller than me, a long slim body, little hair on his arms, brown curls on his head and a bright smile. I never fancied that my first sex would be with a quite nerdy average grown up man, I always thought of something steamy happening on a class-trip of in the shower after sports-class, but this was real life and no porn movie. Tom and I stepped into the elevator and the minute the door closed he carefully touched my face.
"Can I kiss you?" he asked.
"Sure" I answered.
I had kissed before, but all tongue-playing with girls in summer-camp was childish fooling compared to what Tom did with my mouth. I had no Idea how it feels when you really try to push and suck and snog and everything. When the elevator reached his floor, my cock was hard again, and I could feel his cock growing inside his jeans. I was bursting with excitement.
Tom and I sat down at the kitchen table and he offered me tea and some breakfast stuff. I could not eat anything at all. I was way too excited. Suddenly he said:
"Have you ever watched gay porn? Do you know what gay sex is? Sucking cock, fucking butts, rimming?"
"No, yes, but, let me...." I tried to answer.
I was a bit overwhelmed by that question. I started again:
"I know that there is oral sex and anal sex, but what is rimming? And no, I have never watched gay porn; I do not even watch television."
"Alright, then let's put on a little video, and the rimming is for later." He paused, and then continued: " What exactly did you have in mind when you came here?"
Again I was not capable of answering directly.
"Well ...I just thought we.... just see how far we get, and what I like. And I think I would like to buttfuck, or at least give it a try today, I don't know," I said.
"It's fine with me, it's Your first time, so You must say when you have enough, but if you want, we can also fuck today. But let's start with some porn first. What do you prefer? American Muscles or Bulgarian Boytoys"
He put on the tape with the Bulgarian boys, and we both sat down on the sofa. The whole time my penis was full erect and pressing against my jeans. I was so ready to go. I think I just didn't notice any of the action going on on-screen; I was just waiting for my personal action to begin. And I did not have to wait for long. After about one minute of watching porn Tom switched the Video off again and said:
"Porn is boring, lets do something ourselves."
He bent over to me, gave me a short kiss on the mouth and started opening my pants. My belt went open, my pants were being unbuttoned and suddenly I could feel Tom's big warm hand touching my cock. His hand covered my whole crotch, my briefs still on. And I was already close to cumming. He gently stroked my dick and balls through my briefs, an amazing feeling like never before. Then he kept still and just held my package in his one hand. For a minute or more without a move, he just sat there next to me, holding my dick and smiling at me. Slowly I was relaxing a little.
I became curious about his dick. When he rose up from the sofa I also stood up, following him to the window. He closed the window blinds and we stood there face to face, well -- my face to his chest, his face to my forehead. I kept staring on his pants, where his quite impressive bulge was indicating that he was aroused as me. I opened his belt and unzipped his jeans. When he pushed down his pants I could see that his penis was hardly fitting in his briefs, his top and balls sticking out where the briefs did not provide enough space. I ran my fingers over his bulge; he made a faint moaning sound and smiled even more. Almost simultaneously we started pulling off each other's t-shirts. Still by the windows we just stood there, shirtless with jeans at our ankles, stroking each other's bursting briefs. We didn't say a word and then moved on to his bedroom.
Before we laid on his bed, we finally removed our underwear. His briefs came off and his cock came to full sight, eight inches long, pretty thick, and uncut.
"I have never been so close to such a big dick!" it's beautiful" I said, embellishing the fact that I had never been so close to any dick at all.
"I bet yours is really really beautiful" he replied and slipped his hand into my brief.
For the first time with no layer of fabric between his fingers and my dick, the feeling was even more intense than the first touch minutes ago. My dick was sticking up against my briefs so bad that he actually had to hold it down to pull down the briefs. So when he released his hand, my dick sprang up against my belly, making Tom laugh a short laugh.
"See, it's a perfect teen penis, it's wonderful, I already love it", he said.
I had quite some pubic hair going on, but my chest and arms were hairless by then. As a late developer, I was quite small for my age, including my dick, which was about five inch long and relatively thin, but Tom didn't seem to mind.
We were lying in the bed and Tom was stroking my dick and balls, I was doing the same with his. Suddenly he sat up und bent over to my dick, kissing the top, licking away the shiny drop of precum. I was in shock, I real guy was just seconds away from sucking me! I could not believe it. Tom was licking around my dick, around the balls and back. He kind of sucked my whole testicles, which was weird, but it felt wonderful. I was just sitting there watching this happen, hardly believing what I was seeing. And then it happened! He engulfed my dick with his soft lips, slowly sucked, and I was in heaven. I could not believe this feeling. My dick was sending waves of energy and tension through my body; I fell back to my back, sticking up my dick towards Tom's mouth, where he was steadily moving his tongue and lips around my penis. After about 30 seconds of oral sex I was seriously climaxing. I gave Tom a quick warning:
"Stop! I'm cumming!"
But he just kind of overheard my warning and kept on sucking. And so my orgasm was coming. I felt it almost as a pain in my balls in the top of my dick, but soon it burst out to a wonderful orgasm, as I shot my load into Tom's mouth.
"Holy shit!" I screamed;
I had never felt anything like that before. I collapsed on his bed and let the orgasm take over my body until the last of the spasms subsided and I floated slowly back into reality. Tom just kept on sucking, like he wanted to get as much semen as possible of my teen juice, swallowing every drop of my cum greedily. I was shocked. First because I had just been sucked off by a man nearly twice my age and second because swallowing cum was totally against any rule of safer sex!
"You can't do that!" I complained "It's totally dangerous to swallow cum, haven't you heard of HIV?"
He was still smiling and licking his lips. "Well, do you have HIV?" he asked me.
"No, of course not" I said angrily, "but I could have lied to you."
"Well, I can somehow tell that you have never had sex before, that's for sure at least" Tom said. "And I trust you."
I was sure that I was right, but on the other hand I was glad that Tom was such an irresponsible person. Somehow this was pretty cool, being sucked off and cumming into his mouth was definitely fun. I stopped arguing. I did not want to talk about safer sex as long as I was on the safe side anyway, and Tom was right, the chance of me infecting him with something was just ridiculously small.
Anyway, the other problem was that I was pretty exhausted after all this and now the tension of the whole morning and the days before came off. I fell back down on Tom's bed and almost fell asleep. Opposite, Tom was still pretty horny. And there was a problem of sex in general that I had thought about and never found a satisfying answer: What happens if one cumms, and the other one is still horny? In my case the solution was just about 12 minutes away, because it did not take that much time for me to become horny again. I was sixteen then. And sixteen year old boys are like fountains of semen, the sexual drive does not stop for years. And lying next to a naked man with a hard eight inch cock was more than enough to start me again. Tom stroked my balls and my dick and it did not take much time for it to become hard again. He started sucking me again, but this time he started in a different way. He opened his mouth wide and took in my whole cock and my balls at once! He just kept still like that for quite some time. The top of my dick softly enclosed by the back of his throat, I was in heaven again.
But now I wanted to explore his dick and balls with my tongue as well. Tom realized what I was up to and changed his position. From kneeling between my legs he rose up and turned around. I was still laying on my back, my arms and legs wide spread, my cock sticking up in the air -- or more like directly pointing to my chin.
Tom climbed on top of me on his knees, his face right over my cock, his cock dangling right over my face. He slowly lowered his hips, his huge cock coming closer to my face. I grabbed it and guided it to my mouth and started licking around the head. The taste, the texture, the site of tool turned me on. I licked his balls, which were not pulled tight to the base of the penis like mine, but were hanging low and kept clutching my face. I was a little scared to suck a big dick like his. And the position which gave me no space to move made me a little uncomfortable, but the moment he that Tom was sucking my dick again made me forget all my worries and I happily took the red and lush top of his dick into my mouth. This went on for a while. I sucked his dick in various ways he told me to suck his balls and I did.
He showed me how he wanted his dick sucked by performing it himself on my dick. And I tried my best to give to him, what he was giving me down there. Then I showed him what I liked best by performing it myself on his dick and his balls. So we spent quite a while like this.
"And now, can you do it like this?" slurp
Again, I was climaxing. And again, Tom sucked every drip of cum from my dick, leaving me pretty exhausted again, shaken from a second -- even more intense -- orgasm.
"I need a break", I told him. "And I am hungry and thirsty and want to get dressed."
"But are you alright with what happened?" he asked me.
"Well I do feel a bit awkward, but I guess it has nothing to do with you, it's just general weirdness."
"Fair enough, this is your first gay sex, you have every right to be weirded out."
"How do you mean that?" I asked
"Well, I am from a very religious family and it took me years not to feel guilty about gay sex. Do you feel guilty right now?"
"Yes, in a way I feel guilty. I mean, I lied to my parents and everything."
"Do you want to take a shower? Maybe that helps. Cleaning your body is always cleaning your soul as well."
"Alright, sounds like a good idea."
"Come with me, the bathroom is this way."
So we went to the bathroom, where Tom handed me a towel and showed me to the shower. He left the bathroom and I stepped into the shower. It took about a minute until the Tom knocked at the door.
"Can I come in?" he asked
"Well... yes" I hesitated a bit.
"I know I am a nasty person, but I can't resist you."
"Okay, come in."
Needless to say, my cock grew hard again the very moment that Tom entered the bathroom. Tom opened the door to the shower and smiled a bright smile.
"Somehow I knew you'd have a boner again"
"Yeah, I know, I just can't do anything about it"
"So do you mind if I give you a proper washing then?"
"Well, no, but a boner does not mean that I am into wild sex again." I said
"That's not a problem" he said
"I just want to touch you, that's all."
Top entered the shower cabin and grabbed the soap. He started soaping me from head to toe. I just stood there while Tom was standing behind me, his cock pressing against my back. He rubbed my body and naturally paid the most attention to my cock, balls and ass. His fingers running back and forth through my crack felt good, and it was giving me an exciting glimpse of what was to come later that day. But for now, Tom kept soaping my hard cock, one hand moving up and down my dick, the other hand had a tight grip on my balls.
He stood behind me tight, rubbed his cock against my body and it didn't take long until I was again ready to cum. Tom kept masturbating me, I was moaning, the Top of my dick already feeling hot and sensible, now that my third orgasm in one hour was coming towards me. The liquid shooting from my dick was thin like water now, all sperm was shot out before, and it was just the watery fluid from the prostate, staining Toms bathroom tiles. Tom left the shower and let me finish alone. I was irritated and happy at the same time.
"Let's grab something to eat outside, the weather is great" Tom said when I stepped outside the bathroom, while putting on pants and shirts.
We took our bicycles and rode around his neighbourhood. We stopped at a burger restaurant and got us some fast food. We talked a lot about many things, but nothing really deep.
About one and a half hours later we got back to Toms flat. We were joking and laughing, grabbing each others dicks and asses as we climbed up the stairs to his floor. We stormed into his flat and landed on the sofa -- like the beginning sequence of a Simpsons-episode.
"So how do you like gay sex so far?" Tom asked
"I love it" I said and smiled.
"And do you want o go all the way today?"
"Sure! Why not?"
He smiled and said: "You know that there is always a top and there is always a bottom..."
"Yeah, I know. What is your preferred role?" I asked naively.
"Well, I'm pretty much 50/50, you know? It always depends on the partner. If I see a cute ass like yours I want to top it right away. But if I see a big hunky guy with a big cock, my asshole starts twitching and I want to be fucked."
"Do you mean you want to fuck me now?" I asked.
"If you ask me like that... I have to tell you .... that I wanted to fuck you from the very first moment I saw you." He said.
I was irritated a bit.
And he continued: "But let's put it this way, you are sixteen and this is your first time. I won't force you to anything. Let us do it like this: you fuck me, and then decide if you want it the other way round as well."
And he put on his bright smile again.
"Alright" I said, still a little uncertain "Let's give it a try"
Now I was excited. I was about to fuck a guy's ass. It seemed weird to me though, he was older and bigger. It would be kind of natural to be fucked by him, but what the hell. If fucking was only half as good as getting my dick sucked, this day would be the best of my life.
Tom got up and started undressing. I started undressing as well. My cock was hard as rock again, though already aching a little from the last three comings. I went to the bedroom and placed myself on the bed, while Tom was taking a bottle of lube and a package of condoms out of his drawer. He sat next to me and let himself fall back on the bed, his legs swinging up in the air, where he kept them still. Then he placed his feet on each side of me, exposing his dick, balls and hole right to my sight.
"You know what this is for, right?" he asked, while popping open the lube and dripping the thick liquid over his index finger.
"Yes, I know. I'm inexperienced, but I'm not stupid" I said and smiled.
"Alright, alright. Get some yourself, come over here!"
He took my right hand and put lots of lube on my index finger as well.
Then I got back to my position observing his asshole and watched Tom massaging it.
"The more relaxed it is, the easier it goes in" he said, his cock slowly rising to full erection.
So far he had touched my asshole only shortly in the shower, but even from that brief moment I could imagine how it must feel to get a good massage down there. Then Tom slowly slid one finger up his own ass and moaned in pleasure. I saw that he was pushing his asshole against his finger, revealing more and more of that darkish roselike muscle. I was a bit sceptical if he was showing off, and if his finger would be full of shit when he would pull out. But his impressive hard-on told me he was not faking; and when he released his finger from his ass there were no traces of shit on it. I was relieved, but still sitting there a bit stunned and distant.
"Come on, if you want to fuck me, you have to finger me!" Tom said.
He took my hand and guided it to his asshole. I stuck out my well lubed finger and placed it right on his hole.
"Now go ahead" he said and I actually started to push my own finger into another man's ass for the very first time. It made me want to fuck him immediately. It felt great, especially that Tom would sigh in pleasure every once in a while when I hit certain spots in his inside. "Take a second one." He didn't have to say that twice! I lubed up my middle finger as well and started fingerfucking Tom with both fingers.
"Can we fuck now?" I asked.
He just smiled and reached over for the condoms without letting go of my fingers that were still stuck up his ass. "Here! Let me put it on you."
Now he sat up, letting his knees drop to the bed, my fingers slipping finally out of his ass. He shifted his bodyweight up again to grab my little dick. He rolled the condom over my cock and put more lube on it. Then he turned around and sat on all fours with his backside to me. I was about to fuck him doggy-style.
I sat up on my knees right behind me and probed with my finger to locate his asshole again. Then I came closer bit by bit and finally reached a good position. The top of my dick was now touching his hole. He reached around his back to me, holding my buttocks in his hands and pushing my hip into the direction of his ass.
Then my dick entered his hole. There was a slight resistance, but not as much as I imagined. It felt warm and tight and good, but somehow my dick was seriously aching. It had endured a lot today. And soon I realized that it would be impossible for me to enjoy this fuck.
I hugged this guy from the back, my dick up his ass and somehow he was having more fun than I did. I didn't understand: I always thought that the top part was the fun part, and the bottom was some kind of victim.
But this was different: I started to slide my dick in and out Tom's ass, but the more we did it, the more it felt like I did all the work and he had all the fun. After a while I had to stop because my dick was hurting too much.
And maybe shy-and-inexperienced-teenager fucking a straightforward-30-year-old was just not in the sense of gay-anal-sex's inventor. So we stopped and I pulled out.
"So what's wrong?"
"My dick aches!"
He just smiled "It had a lot to do today!"
I was a bit disappointed. After a spectacular day with lots of kissing, jerking and sucking, now the highlight -- the fucking -- just didn't work out like I wanted.
"Don't be sad. You came off three times today. I wish I could ever do that." Tom said.
"But you could when you were my age, right?" I asked.
"When I was your age I was still six years away from my first sex."
"You were 22 when you had your first gay sex"
"Yes, and it was awful. I want yours to be better than mine."
"It is definitely good" I said and smiled.
"Do you still want to try anal sex the other way round? Do you want me to fuck you?"
"I don't know" I said. "I'm a bit scared."
"Let me help you to make up your mind."
I thought I knew what was about to happen. He was going to suck me again. But my dick was aching and I was captured between excitement and exhaustion. I wanted to get off again, but I couldn't anymore! He positioned me on my back like before -- just as if he was about to suck me off again - so I said:
"I'm afraid you cannot suck me of no more, it was too much for my dick so far."
"Relax. I won't touch your dick. Promise. But you have to trust me."
"Alright"
So I just laid there and waited for him to "convince" me. He pushed my head back down to the bed and grabbed my thighs from the underside. Then he lifted my legs up and moved his head closer to my now exposed ass.
"Remember the rimming?"
And then I had another revelation. Tom ran his tongue around my asshole, a tickling and wet sensation rushed through me. This was brilliant. Tom continued seriously wetting my asshole with this tongue; I grew more horny and horny. My dick was rock hard all the time, I was desperate to get off, but the sensual sensations came to my own surprise not from my dick, but from my asshole! And then I felt Toms tongue entering my hole just for a second. He gave some muffling sound: "hmmmmmmm" I was excited as hell and wanted more of his tongue up my ass, but he moved back and asked:
"Are you alright with that?"
"Are you kidding? This is fucking great! Please go on!"
He just smiled very bright and licked his way across my whole body back to my asshole. His tongue went up my ass again and I sighed in relieve. It was like the ultimate relaxing massage. After some time of rimming I was ready to burst. And then I just heard myself saying:
"Please fuck me Tom!"
I guess he kind of convinced me.
Nothing happened, no response. Toms tongue was continuously wandering around, in and out of my asshole. I was again captured between ecstasy and uncertainty. But I could not stop it, so I said a little louder:
"Tom, I think I want you to fuck me."
This time Tom stopped and turned his face towards mine. He looked happy like a kid at Christmas. He smiled widely.
"Alright" he said, "we'll do whatever you want." Tom moved his away from my ass and came closer to me. He smiled and kissed my forehead.
"Does it hurt?" I asked.
"Yes, but in a good way."
"Did I hurt you when I fucked you?"
"Well" he said and laughed a little. "It depends on the size of whatever you shove up your ass... and I had much bigger things up my ass than your cock. No offence. And I had a good fingering."
"But do you think you will hurt me?"
"It depends. If you relax enough, my dick could just slide in like nothing. That's why fingering is good. You can slowly adapt your asshole to the size you need. I will put as many fingers up your ass until you can take my cock easily. Let's go"
Tom grabbed another condom and the lube. He unpacked the condom and rolled it over his cock. Since it was pretty big, he had quite a hassle doing that. When he was done with the condom, he put lube on his finger and rubbed it against my asshole. I didn't move all the time, my legs were still spread and up in the air. Tom placed my thighs on his shoulders and started pushing his finger slowly against my ass. "Now push your asshole against my finger, just like if were taking a shit." I did like I was told. Doing that, the muscular resistance disappeared and his whole index finger slid into my ass. This was another sensation. It just felt awesome. Tom smiled at me and I smiled back.
"Is that alright?" he asked.
"Hell yes" I answered.
He moved his finger in and out my ass and probed around until he hit a spot that made sigh in pleasure.
"Your prostate." He said. "You know it, don't you?"
"Yes" I said, hardly able to speak straight without trembling. "But I didn't know how it feels to touch it" I continued. And then: "Please touch it"
I wiggled my body from side to side. My Asshole being the centre of movement, where Tom was giving me a serious fingerjob, eventually hitting my prostate and making me moan. Then he introduced a second finger into my asshole. It hurt a little, but the pain subsided fast. I was still in full ecstasy. In addition, he deepthroated me from time to time, I felt like in heaven again. Then a third finger came in and my ass began to feel really full and tense from the inside. Tom smiled at me and worked his three fingers up my ass, just to let them slide out completely again. I felt empty end restless. I his fingers back up my ass. When he pushed his fingers back in, the slid in easy like it was only one. My asshole must have been pretty relaxed by then. I was entirely happy with his warm and big hand down there, giving me sensations from my butt. My penis gave an unsteady stream of a clear watery liquid, but I was not even close to cumming. Tom was now over me, his one arm placed next to my torso, supporting his body. His other hand moved in an out of my ass. My legs were still placed on his shoulders, but since he had moved his head closer to mine, my knees were now almost over my shoulders. In other words, he was positioning us for fucking.
And then I felt the top of his dick pressing against my asshole. Tom still had three fingers inside me, and now he used them to guide his cock into my ass. And then he shoved a big part of his eight inch cock up my ass. And yes, I did hurt. He pushed more and I felt like I was exploding. He slid the full length of his cock into me!
"Ughh" I said. My eyes were wide open. Pain and pleasure were equally distributed, but I needed a break. "Please stop" I said.
"Sorry" he said and removed his cock from me. He sat back looked at me. Then he said: "Maybe this is not the right position for starters. We can stop for today if you want to."
But while saying this, he had already slid a finger into my ass again and was hitting the right spot again. I could impossibly stop here.
"No, don't stop now"
"Alright, I would also love to fuck you some more, if you asked me. You are a hot piece of ass. Then let's try something else."
Tom laid back on the bed, now his cock sticking up in the air. He put more lube on it and wiped off his fingers in a towel he had placed next to us on the bed earlier. Then he guided my Torso with both his hands on top of him. I sat on him like riding a horse. He looked up to me and I looked down to his face. Then he started pushing my hips and legs down towards his dick.
"Try to sit on it" he said "So you can control how much you take in."
I did like I was told and this time I grabbed his dick and guided it towards my asshole. I pushed like I was shitting, just like Tom had told me earlier. The top of his cock slipped in. I stopped there and waited. It didn't hurt at all. Tom sighed and hummed in pleasure. I was willing to take more. Somehow I was pretty obsessed by the idea. I must take his whole cock. It must be possible. I wanted it just to prove it to myself. And right now it was pretty comfortable. Not quite as hot as the fingering, but every second it became better. I pushed my ass back down his cock. He just held still and sighed. I moved back up a bit, to relieve the pain. But with each inch, the pain/pleasure-ratio became better, and when Tom started pushing his dick into my ass himself it felt as easy as his first finger.
"Are you still alright?" he asked me while sliding the most of his eight inches in and out my butt.
"Yeah" I said. By this time I had completely adapted to his size and I was receiving simply a good fucking.
Tom started pounding me and sweat began running from our foreheads. We fucked quite some time like this until Tom suddenly said:
"I think we should try another position. I can't climax this way, and maybe for you it's also more pleasurable."
"Aright, whatever you say"
Tom let his dick slide out of my ass and rose up. He pulled the condom off his dick and opened another one. His dick was really big. I was shocked that I had this thing all the way up my ass. I got up from the bed as well.
"So what do you suggest?" I asked him.
Tom rolled the new condom over his cock and lubed it up. "I would suggest that we walk into the kitchen and you stand right two feet in front of the kitchen table"
"Alright" I said, if he wanted to fuck me there I was fine with that.
So we went to the kitchen and I stopped two feet before the table. Tom bent my torso towards the table so I had to support my body with my arms placed right on the table. Tom stepped back behind me and tilted my hips back so that I was now standing like one of the Bulgarian boys from the porn movie that we had watched for a minute this morning.
Tom performed some jerking moved on his cock, distributing the lube and giving it the right erection. Then he came closer to my backside and ran his fingers through my crack. When he found my asshole, he stuck a finger inside, which gave a boost to my erection again. I was instantly back on the track.
Guided by his finger, his dick slid up my ass again. He pushed it up all the way, this time with no pain at all, leaving me breathless with pleasure. Tom started fucking me again, this time a bit harder and due to the other position, his cock hit my sensitive spot more often than before.
He was giving me a good pounding right away, the precum-like clear liquid was now flowing from my hard cock from time to time as we went on; Tom reached around and started to jerk my penis with his lubed hands. I just grab his hand and push it against my balls to stop him from masturbating me, but it's effortless. The pressure of his and my hand against my belly makes it even worse, I'm climaxing even more like this. His cock is thrusting against my prostate even more like this; my balls and cock are aching like hell.
I feel like I have to explode, but instead of orgasms I experience waves of arousal coming and going. It feels like orgasms, but I don't ejaculate; it feels like ejaculating, but there is no orgasm. Tom fucks me steadily and grunts like an animal. I hold Toms hand tightly and he holds my cock and balls. But he is much stronger than me and so I give in. Tom starts jerking my dick in the same speed like he is fucking me. And this time I have absolutely no chance. I am finally climaxing for good. I scream. It is the most intense feeling I have ever experienced.
I shoot my load and scream. "Fuuuuuuucckk!" My cock and balls pump incoherently like there as still semen left in me to shoot out. Spasms shake my whole body; my ass is contracting and relaxing, making Tom even hornier. Tom is screaming as well. He is cumming, too, the very same time. He just keeps pumping his load up my ass. I feel the condom being filled with his juice. But I am out of my mind. I collapse on the kitchen table. And Tom collapses over me.
Minutes passed by and Tom and I just stood there, our Torsos collapsed on the kitchen table. I felt his dick still in me, suddenly giving me a strange feeling. I had not only lost my virginity to a man, but also I had been seriously turned on from being fucked up the ass. Now I felt a bit guilty.
Tom's dick began to shrink and he pulled it out of my ass. I felt strange and empty. I watched Tom wrapping the semen-filled condom in some twinkies and throwing it into the kitchen-dustbin. Just standing there, my legs still spread, I felt small and big ad the same time. On the one hand this was definitely an adult thing. I was really into sex with men. But on the other hand I was definitely some kind of child having been fucked by an adult.
Tom came back and handed me a glass of water. I drank, it felt good and healthy. We walked back to his bedroom, curled up under his blankets, not saying a word. I wanted to go. Tom was looking at me like he was feeling a bit guilty as well. I think he realized that our fucking had ended up pretty rough. And that the whole day turned from careful introduction into plain hard fucking. We both looked at each other like we had done something forbidden, which technically -- considering the fact that I was definitely underage -- was the case. I got dressed and Tom put on some fresh clothes. Then he broke the silence:
"Will we meet again?"
"I don't know", I said, "but I thank you for the day."
Silence.
"You don't have to thank me. I have to thank you." He said. And then after another break: "I understand if you don't want to answer any questions now. But if you get horny again, and you feel like coming here, you are more than welcome, just remember that."
"I know" I said.
Another silence passed until I continued:
"Well, I get horny pretty often. And this was a great day. I'll call you."
"Alright, I trust you."
"But now I want to go home."
"Fair enough, I'll guide you down to your bicycle."
"I think I walk from here to the next subway-station. I don't feel like biking right now" I replied.
"Then I'll walk you there."
Walking in the fresh afternoon-air next to Tom made the whole perspective on gay sex much more appealing then it had looked so close after our fuck. My ass began feeling strangely good and the pure thought of what just had happened made me horny again. I smiled. Without talking we reached the subway-station and Tom waited with my on the platform until a train came. I sat down, smiling at Tom who smiled back from the platform. While the doors were being closed, Tom stuck his whole index finger into his mouth, sucked it, pulled it out and gestured like he was sticking his wet finger slowly up an imaginary ass right in front of him. I got the message. And my cock went hard again.