My first fuck

[nate88]

I know first time stories are a bit of a cliche but a few guys have asked me about mine so I thought it would be best to post it here. I don't think I'm allowed to say this is a true story according to the rules so I'll let you decide for yourself.

In the mid 2000's my hormones were raging and I was constantly horny, like any other lad my age I suppose. By this stage I had already had some experience with other guys close to my age but blowjobs were as far as we'd gone - I had never had anal sex, and I had never been with an older man.

It was summer and I was over at my best friend's house for a barbecue. It was more of a family day for them but they also invited some friends of the family, like me. Another of those family friends was named Adam - he was friends with my friend's older brother. He was in his early 20s with dark hair and tanned skin, and he was a skater. We had been around each other a few times before at events like this and I thought he was a hot guy, but we had never spoken or paid attention to each other. I also knew he had a girlfriend so I assumed he was straight.

For some reason the energy between us was different this time though. He caught me staring at him a few times and I noticed him staring back. It was one of those classic situations where there was a certain mood in the air between us but we were both too nervous to break it. He was older than me and despite my previous encounters I didn't fully understand the subtleties of flirting yet. It was unexpected and exciting but I still didn't expect anything to come from it.

Later in the afternoon it was time for me to leave. I was saying goodbye to my friend and his family when I noticed Adam was getting ready to leave too. I was planning to walk home because I didn't have my license yet and my house wasn't far away but somehow we figured out he was heading in the same direction, so he offered me a lift home. The electricity in the car was palpable - I had never experienced anything like this before.

He asked me for directions to my house, and - doing my best to be casual but suggestive - said something like "take the next left, or keep going down this road if you want to mess around". He kept driving.

We drove for a few minutes and he pulled off onto a dirt road which led nowhere - where we'd be safe from anyone driving by. I was nervous but he seemed more nervous than I did, which gave me a strange sense of confidence too. "You can't tell anyone about this" he told me, "especially not Christine" (his girlfriend).

We got into the backseat and started stripping each other. As soon as his undies were off I dived head first onto his cock. He was a good size at 7 inches or so, and he was uncut - which was exciting for me. I'd never been with someone who was uncut except for when I was much younger. This was the first fully developed uncut cock I'd had. He tasted clean but musky, I fucking loved it.

While I sucked him he reached back and rubbed my asshole. After a while I sat up and asked if he wanted to fuck me - he was breathing heavily from the bj as he nodded, but then said "fuck I don't have a condom with me". I said "don't worry about it". He seemed to think about it for a few seconds but then reached into one of the pockets on the back of the front seat and pulled out a bottle of lube. I guess I wasn't going to be the first fuck this backseat had seen.

I don't remember telling him I was a virgin but he seemed to know, either through intuition or some other way. I lay on my back with my legs raised while he fingered me for a few minutes to lube me up. The backseat was uncomfortable and the car was hot, but I was too horny and excited to care.

Finally he moved into position and I could feel his cockhead against my asshole. I remembered to relax and push out from the time I'd spent fingering myself and using vegetables or whatever else I could find to fuck myself with. I distinctly remember the tip of his foreskin touching my ass and feeling it roll back as he pushed forward. I never expected to actually feel his foreskin roll back over his cockhead as he pushed into me, but I did.

It took us about a minute before his head finally pushed through and entered my asshole. He was thicker than what I was used to and it was an uncomfortable feeling, but not as painful as I expected. He didn't wait long to start pushing the rest of his cock in - I think his nerves about what we were doing and doing it in such a public place were getting the best of him. I wish he had taken more time and let me adjust to his size, but although it was uncomfortable my horniness was overriding most of the discomfort. I don't know why because I was used to playing with my ass, but I remember thinking "wow it really does feel like taking a backwards shit" as I kept pushing out with my rectal muscles while he pushed in. I tried to stay quiet and not sound like I was being a pussy, I didn't want him to think less of me, but I would have grunted and made some sounds which I couldn't hold back. Finally I felt his pubes press against my taint and balls as he bottomed out - another new sensation I hadn't expected.

This time he stayed put and gave me some time to adjust. He probably wanted some time to adjust to the feeling of my virgin asshole squeezing his cock too. I remember my asshole twitching and squeezing him and the moans he made each time. After a while he started moving in and out and fucking me properly. Again I remembered thinking it didn't feel as painful as I expected it to feel, although it was still a strange sensation having something move in and out of my ass without me controlling it. I zoned out for a few minutes while I tried to get used to that feeling, and just as I started to feel my muscles relax and that slight burning sensation change into pleasure, he pushed all the way in and shot his load.

I was disappointed because I didn't want it to end yet - especially because I was just starting to enjoy it. But I smiled at myself knowing I had a load of cum up my ass. I had jerked off to so many bareback and creampie videos, now it had happened to me. He pulled out and started wiping the lube off his cock with a rag he kept on the floor. Some part of me wanted to wipe it off for him and wanted him to wipe the lube off my ass for me - something about that idea of us cleaning up each other and sharing that intimacy appealed to me, but instead he just passed me the rag when he was done and I cleaned myself up.

On the drive to my house we barely said anything to each other, and we never hooked up again. I hoped it could become a regular thing and he'd want to fuck me all the time now that we'd broken the seal, but for whatever reason he wasn't interested. But I had finally gotten fucked and I was so happy with myself for days afterwards. I remember sitting at the dining table eating dinner with my parents that night and feeling my guts rumble as his load moved around trying to get out - I stayed hard the whole time until after dinner when I finally sat on the toilet and jerked off while I farted out the load and lube he left in me.

That began my career as a vers bottom in my later teens and early 20s, although I grew into a vers top as I got older. It might not have been a perfect first time experience, whatever that is, but I've used the memories of this first experience as lessons learnt for the bottoms I fuck - especially the first timers. I like being intimate, I like taking my time to make sure he's comfortable, I like learning what feels good for him and teaching them about what feels good for me. I like exploring all the different dimensions of sex beyond just the physical fuck, and I always try to make sure his first experience lasts as long as possible to let him savour and experience those new sensations for the first time. I try to give him the type of first time I wish I had. I've shared those experiences with about 4 virgin bottoms so far and it never gets old.

[plisken]

Nice way to start a life of fucking

[Trainingwheels]

Awesome story. You are the exact kind of top I need to help me finally get comfortable with bottoming!  When I was a( 18+ totally legal) kid my hook ups were in public, cars, parks, bathrooms etc. so none of the hot older men were into being patient.  It was like you want to fuck around like a slut with the big boys then you’re gonna get fucked like a slut. I guess looking back I’m lucky nothing really bad ever happened to me. I think in part because when they realized it was going to be harder to fuck my ass than they had thought was when I turned and dropped to my knees and deep throated their hard dicks. They seemed happy once they realized they could fuck that hole and I would happily take whatever they gave me over and over. Gagging, eyes pouring tears, snot and throat slime running down my face and body l kept coming back for more. I was an insatiable  cocksucker. The older I get the harder it seems to be to find a patient top…it’s like no one can believe a post 40 something gay man who gives off bottom interested vibes is still almost an anal virgin. Anyway your story gives me hope!

[bcbip]

Nice!

[DNG999]

Enjoyed this one