Finally My First Time

This is the story of my first time with a guy. My name is Simon and I'm 25, 5'10" 13st with a slightly athletic build. I had been bi curious for a long time, I watched a lot of gay and shemale porn and experimented with butt plugs and dildos while masturbating. I first became aware of my sexuality while watching straight porn and being slightly jealous of the girl. I found myself wanting to be the one sucking on the big cock or being pounded by it. Nothing turned my on than the thought of riding a big cock. This fascination lasted a long time before I plucked up the courage to do anything about it. For me I'm still confused, I'm not attracted to men but I do like a good cock.

So how did my first time come about? Well it started online as most sexual experience do these days. I was on a gay chat website talking to blokes and I don't know why but none of the ones I was talking to were doing it for me, they all seemed a bit too aggressive. That was until I got talking to Nick. He was the same age as me same height but slimmer. We seemed to have a lot in common both of us were curious, never been with a guy and really wanted to try new things. Nick didn't live too far away and was free that night. I think my cock made my decision for me as the more we talked the harder I got. Somehow I plucked up the courage to ask if he wanted to meet up to which he agreed so long as we were very discreet which I certainly agreed upon. He was 24 miles away and I wasn't too familiar with the area he lived but we agreed on a location which I knew and a rough time. I quickly got changed, jumped in my car and set off.

I have to say my cock was hard for most of my journey. The night was cold and it was drizzling a little. I headed for our rendezvous location which was a shell garage just outside the city where he lived, as I turned into the road that ran past it I saw him. At this point my nerves got the best of me, my stomach sunk and I panicked a little, I turned into a side street just before I reached him and pulled up on the side of the road. I was shaking, I didn't know what to do. I was just about to pull away when my passenger door opened and in jumped this guy. I was wearing a grey hoody and sweatpants, his head was shaved and he was kind of geeky looking with his thin framed glasses.

"Hi how's it going?" He said,

"Good, You?" I replied, my head was spinning I wanted him out at this point and the run home.

"Not bad. Do you know anywhere we could go?" He asked.

"Not really, I'm not from around here, we could drive around to find somewhere,. Do you not know anywhere?" I asked,

"No, I've never done this before," he replied.

At this point I don't know what came over me, I was so nervous. I looked around into the surrounding darkness, to the right of me was an empty road, in front were houses around 50 metres away, to the left were bushes and behind more empty road. There was little in the way of lighting and I decided that there was nobody around. I decided now that I needed to overcome my nerves or I was going to run.

"Can you get your cock out?" I asked, "Just for a second, I just really need to do something now I'm so nervous."

"Sure," he replied.

He reached down and put his thumb into the band of his sweatpants and pulled them down a little exposing his cock to my gaze. Soft it was 4 inches and uncut, his pubes neatly trimmed. I reached over and took it in my soft grasp. It was cold to the touch, as I played with it in my hand it started to respond, I couldn't resist, I leaned over and took it into my mouth only for a few seconds. It was too uncomfortable to do for a long time as my arm rest and handbrake were digging into my ribs. I found it to taste ok and he smelt clean. It was at this point I knew I wanted to go further. I sat up and looked at his cock, it was hard at this point even after these few seconds. It was about 6.5 to 7 inches and not too thick and was twitching away probably seeking more attention. I looked at Nick and he looked back.

"Do you want to do this?" I asked, my nerves completely gone,

"Hell yeah," he replied.

With that I drove off searching for a quiet spot for some fun. After about 10 minutes of searching and making small talk mostly about where we could go we were having no look.

"Look you seem like an honest bloke, we can go back to mine but you have to be discreet okay?" Nick said to me,

"Of course I will," I replied.

With that he started to direct me to his. He actually lived in a lock of apartments not far from where we met. We parked up outside and I followed him in. He lived in a two bedroom apartment overlooking the river. Inside it was warm and cosy, we entered into the living room through his front door. I looked around, he had wooded floors with a big shag pile rug and he had a corner sofa and a large TV. I noticed a picture on the wall of Nick and a woman and it was obvious that this was his wife on their wedding day. I really didn't care though.

"Should we take our clothes off?" I said,

"Yeah," he replied.

With that we both shed our clothes very quickly, we stood facing each other both our eyes darting to each other's crotches. He was semi erect as I quickly noticed as was I. I didn't want to wait any longer, I dropped to my knees, looked up and his growing cock was only 6 inches or so away from my face and semi erect. He was uncut and had a large foreskin, a bit like mine. His cock twitched, bouncing up and down seeking my attention. This got me so excited I didn't hesitate any longer, I leaned forward opened my mouth and took his cock in my mouth. Having never given a blowjob in my life I had little experience to go by. I sucked and slurped away at his cock slowly, I could feel his cock getting harder and harder in my mouth. At one point I took a little too much into my throat and I gagged a little. I leaned back and let it slide out of my mouth while I gasped for air and to clear my throat.

I looked at his cock all erect pointing straight towards me. At this point it looked very big to me at around 7 to 7.5 inches with about a 5.5 to 6 inch girth. His foreskin had been retracted exposing a nice fleshy head. His cock glistened in the light. I caught my breath and leaned forward once more. He started to relax and make moaning noises which turned me on completely. I wanted more than to only give a blowjob, I wanted to pleasure this cock every way I could. I felt a tingle in my virgin hole, I wanted him inside me.

I let his cock slip out of my mouth again and this time started to lick and suck on his nice big balls. He seemed to really enjoy this, I kept doing this action for a little while, I listened to his moans and groans as I did this, I wanted his cock back in my mouth but this time as I went to take his cock in my mouth he stopped me.

"I want to suck you," he said.

"Okay," I replied

I stood up and faced him, it was at this point I noticed how hard I was. I was granite hard, I don't think I'd ever been that hard. He ushered me over to the couch and sat me down. He dropped to his knees in-between my legs and took my cock in his mouth. He obviously had little experience and although it felt good he was obviously struggling to find a technique he could do. He kept choking on my cock even though I am at least 1 inch smaller than him and a little smaller in girth too. I started thinking more about what I wanted to do. I really wanted him to fuck my arse, I didn't want the blowjob. So I stopped him.

"Will you fuck me?" I said, as I lifted his head off my cock.

"Yeah, are you sure?" He replied nervously,

"Yeah I am," I reassured.

With that he stood up and helped me up from the couch. He took my hand and led me to the bedroom. Where he motioned me onto the bed. The room barely had enough room for the bed it was so small. They had more pictures on the walls of them as a couple. The bed was really soft and smelt clean.

"How do you want to do this?" He asked,

"I find fingering loosens me up," I replied.

"I thought you haven't done this before," He said,

"Only with toys. I find if I finger plenty and used lube it's a lot easier for me to take them." I replied.

"Okay." He replied, "Would it be okay if I rim you first?" He asked,

"Sure," I replied.

With that he seemed to take control, he motioned me onto all fours, arse in the air while he moved behind me. I was a little nervous as I exposed my excited hole towards him. I could feel his breath on my hole which made me quiver. He placed his hands on my arse cheeks and gently parted them before leaning forward and gently licking my hole. I felt a rush of pleasure run through me, which only grew the more he did it. With this and completely out of the blue I found myself moaning with pleasure. This seemed to embolden him, his tongue began to probe my hole, little by little. This heightened the pleasure even more, he seemed to stretch my cheeks even further apart as he tried to make room to bury his face further and get more of his tongue into my rapidly widening hole.

After a few minutes of this intense pleasure he stopped and began to probe my hole with his finger, this brought a completely different pleasure. At first it was just one but that quickly became two, once that was in I began to feel quite stretched. He worked these fingers in and out for a while, with this I gradually got used to the intrusion and relaxed more. He removed his fingers and spat in my gaping hole which he quickly followed up with 3 fingers. With this I lay my head down on the bed and reached back and spread my arse cheeks for him, while he finger fucked me with his 3 fingers. To me it felt heavenly, I was rock hard and starting to feel like I was close to having the larges orgasm I have ever had. I couldn't stop moaning and I kept stretching my cheeks further for him.

"Do you have a condom?" I exclaimed, almost out of breath.

"Yeah," he replied.

"Get it on," I ordered.

With that he withdrew his fingers from my hole and jumped up off the bed and headed over to some draws. While he did this I reached for my hole and began to rub. I was gaping I couldn't believe how ready I was, my hole tingled with excitement. He pulled a condom out of a draw along with something else which I couldn't yet see. He leaned forward and stuck his tongue in my arse one more time. It was immensely good, I almost blew my load then. I could hear the tearing of the wrapped for the condom. I watched as he took it out and motioned it to the tip of his rock hard cock. He slowly rolled it down his cock and was very soon ready to take my anal virginity.

"Would you like some lube?" he asked, so that's what he took,

"Yes," I replied.

With that he squeezed a little onto his fingers and rubbed it into and around my waiting hole. It was quite cold and made me tense up a little. He slipped his fingers back in a little before removing them again. With this I moved further into the middle of the bed and he climbed on behind me. I was up on all fours once again as he took a hold of my hips and motioned my arse towards him, he removed one hand and took a hold of his cock. Very soon his cock was at my hole.

"Ready?" He asked,

"Yes, please be gentle at first," I said.

"Okay, I will," he replied.

With that he asserted some pressure to my hole with his nice hard cock. I was surprised as there was hardly any pain to speak of. I know I had taken thicker butt plugs and longer dildos but I still expected some pain but there was none, just and immense pleasure. He gently edged his cock into me and soon I had taken his full 7.5 inches down to the balls and I was completely stretched out.

"Fuck...you're so tight," he said,

"It feels so fucking good," I exclaimed.

With that he gently began to thrust in and out of my hole, I was loving every thrust. They were small thrusts at first but the more my arse loosened up and relaxed the longer the thrust was. Soon he was pulling out to the head and pushing all the way in. This was pure pleasure for me, we stayed in this position for a few minutes. I had fully relaxed and his thrusts had become firmer. He began pulling all the way out and sliding it back in which felt incredible.

"Switch position," he ordered.

With that he pulled out and motioned me to move. At this point I saw the cock that had just penetrated my hole and taken its virginity. I wanted it in my mouth so much so I lunged forward and quickly removed the condom and tossed it aside. I leaned forward and took his cock in my mouth. It seemed bigger this time, like his cock had swelled to a whole new size and it felt so hard. I can say I enjoy the taste of condom on a cock but I did like the taste of his salty pre-cum and it left the tip of his cock. I took it deeper than ever down my throat and he moaned with pleasure. I could sense he was close but I wanted him to fuck me again. I jumped back and lay on my back.

"Get another condom and fuck me," I ordered,

"I can't that was the only one I have," he replied,

"What? Why didn't you stop me taking it off?" I said quite exacerbated.

"I didn't get a chance," he replied,

"But I want fucking," I shouted,

"I don't know what to do," he replied.

I had a quick think, well as best I could I was far too horny to think. I thought quickly about him being married and probably being clean.

"Are you clean? Like you have no STD's do you?" I asked,

"No, I've only ever been with 2 people, both were women and she made me get checked before we started going bareback." He replied

"Okay, well I'm clean so fuck me." I retorted.

He had a quick think, I thrusted my legs into the air spread eagle and waited for him. He went for it and entered me again in missionary, this time it was even better. His cock hit me at the perfect angle and began hitting my prostate. My cock began to leak pre-cum by the thick sticky mouth full. I was so hard and as he thrust even harder into me his abdomen rubbed against my cock causing me to get even closer to orgasm. I started to get the orgasm twitch. You know the one, when you realise you're on the point of no return.

"Stop," I yelled,

"What's wrong?" He asked sounding very concerned.

"I want to ride you." I said.

He quickly pulled out and lay down on his back and I climbed on top of him. I took his cock in my hand and guided it into my arse. I started slowly but the pace soon quickened up when he started to thrust into me, it felt like heaven. I had a change of mind and wanted to ride him in cowgirl, sorry cowboy position but as I began to move and was in a squatting position above his cock he began to thrust in and out very quickly. It felt so good so I stayed there and let him do it. Then all of a sudden I felt it. It build from by balls to my prostate then I could feel it quickly enter my shaft and then an intense pressure on my head and before I had a chance to react it happened, I had the biggest orgasm of my life. Cum burst forth out of my cock, squirting out in fact hitting Nick as far up as his chin and his cheek. It was so intense my hole spasm out of control. It was all too much for him he slammed deep into my arse and unleashed his huge load. I could feel it fill my hole, his cock twitching as it pumped is seed into me it seemed to go on and on which caused mine to go on and on.

After a few minutes everything subsided. I gently lifted off his cock. I felt his cum begin to drip out so I reached under and caught it as it left my now slowly swelling hole. I caught quite a bit, it literally covered my fingers which I eagerly lifted to my mouth and slurped every last salty drop. Thinking back I can't believe I did that but it felt so right. I leaned down and took his cock in my mouth one last time before licking all my cum from his belly to his chin before kissing him. Which before that meet I had no intention to do.

Things soon calmed down and we started to clean up he let me shower before heading off. When I got out I noticed he'd changed his bedsheets and hidden all the evidence. I didn't stay long as it was not approaching midnight. We exchanged numbers and agreed to do it again but only with each other to maintain our clean status and keep doing it raw as we both preferred it that way.

I left soon after and headed home, arse hole sore, swollen but thoroughly satisfied and impatient to do it again.

I hope you enjoyed reading this as much as I had living it. Thanks for your time.