ps75

Love this thread - just really enjoy hearing about first times. For me the abridged version is first time topping a guy - wrapped age 45, did not cum in him. First time bottoming - bare about 2 years later and I was bred. Here are "firsts" with details For starters, I knew from surfing the web to know how to prepare - so I always "clean" and ready for anything. Outside of some very mild fooling around as a young teen, my first time with a guy I was 45. Seemed he was older by several years. Met on an app - A4A I believe - he told me to "cum" over. It was mid to late evening and he knew it was my first time with a guy. We exchanged oral, then he rimmed me for my first time which was fantastic. He commented how "tight" I was, too tight for him to fuck me so I ended up jerking him off. Afterward he lost interest so I left - disappointed he didn't get me off but several firsts were checked off: being rimmed; jerking off another dude; sucking a guy and being sucked by a guy. Next was another older guy. Went his his place in the afternoon after, again, meeting on A4A. Said he was gay, married, but his hubby was out of town. He was a top but since having prostate surgery he couldn't perform without a lot of effort and rarely bothered but he loved to play with other guys. I never did see his cock as he never took his underwear off. He had me lay on the bed, naked, and he blew me for a while. Then he started playing with my hole. No rimming but inserted a finger (wearing latex gloves). He took out a toy - Doc Johnson Men's Pleasure Wand - I had one at home I had tried on myself so was familiar with it. The vibration function no longer worked on his but he put a condom on it and then put it in me using it to give my prostate a good massage/workout. To this day I have not figured what his technique was, but it was hitting all the right spots with the right pressure making me wild. I blew hands free for the first time which was intense. Funny thing was I still felt I needed to keep going so he pulled the toy out and I started jerking like a maniac while he watched until I finally blew again. So far that is the first and only pure prostate orgasm for me. Hopefully again sometime. On to the next guy. He was 27 and we met up about 4 times over a few weeks. I think he was living in a halfway or sober house as I always had to pick him up and bring him to my place and then he had to be back before a certain curfew time. Anyway, he was bi and a total horndog. He bottomed with guys but also fucked girls. One time I even picked him up from a girls place to take him to mine! He assumed condom use and since his background seemed sketchy I was happy to oblige and I fucked him wrapped - my first time topping a dude. Could not cum but I fucked him for a LONG time which is what he wanted. Then he used his mouth to finish me off (first time I came from a guy giving me oral). We did do a couple other things together. I blew him one time for a bit. He was uncut and that was my first time getting to play with and get a close up look at an all natural cock. He said it was the first time he had oral from a guy and he also attempted to top me which he said he had not done with a guy before either. He was wrapped and poked his dick at my hole hard. I'm not sure if he entered me or not - if he did just the tip was in momentarily - it hurt like hell and he pulled back immediately saying I was too tight. Now the guy that really deflowered my ass. We met up late in the evening having chatted on Adult Friend Finder. I went to his very small place, basically one L shaped room with a bathroom in a semi-rural location. He's in the shower when I arrive and tells me to get naked and sit on the couch/futon. I do and soon he comes out naked and offers me a beer. We sit naked, drinking and talking for a while. He moves close and we start feeling each other, kissing a bit, blowing each other and then do 69. It is all very relaxed and chill, no rush taking our time. He starts to play with my ass, fingering me which goes on for a while. We get up and he folds the couch/futon down into a bed and tells me to get on my knees with my butt up, face and chest down on the mattress. He plays with my hole more and gets out astroglide working some into me and lubes his uncut cock. We didn't talk about condoms. I had seen a box in his bathroom but he doesn't put one on and I just go with it. He takes aim and starts pushing in. Taking his time and he gets in slightly which HURTS like hell - a sharp, stinging sensation. The astroglide was causing a burning sensation deeper inside which wasn't helping. He pulls back and coaches me to relax and gives me a minute before he tries again. After a couple more iterations of this he is in all the way and very slowly/gently fucking getting me used to it. The burning sensation was still there but diminished and the sharp pain was gone. It was slightly uncomfortable and periodically I would have an urge to clench which I had to resist (sometimes unsuccessfully). He was patient and had nice strong boner that didn't get discouraged! He kept going slowly fucking me and I found myself hoping he would finish soon. He sped up and I figured he was close and soon he was banging me good and then pushed in deep and unloaded. He stayed there for a short bit then pulled out and we went back to talking and drinking more. We moved on to round two and he spent a lot of time playing with my ass until he fucked me again and pulled out jerking off to finish. When I was leaving he made a comment about I would remember him the next time I took a dump which I found oddly hot. I was happy to have done it but I had some lingering doubts about him cumming in me. The next day I messaged him on the app. to re-confirm his disease status. Eventually we met up a couple more times. Similar scene but he pulled out to cum during these later encounters. I would have preferred he blew in me but he was confused about what I wanted from my earlier disease concern. His cock never felt that comfortable in me and, thinking back, he had a pronounced upward curve to his cock. The combination of astroglide burning sensation, his curve hitting the wrong spot in doggie position and my newness to bottoming, it just was never pleasurable for me. With different lube and a different position I think it would have been better. The last early fucking experience of note was another 27yo I met online. He lived 6 hours from me but I was going to be in his area so made plans to go a couple days early to stay with him. Even though I had some experiences at this point, I was still pretty new to the guy thing and he wanted to "show me the ropes". Got there in the evening and we hung out talking for a bit. We started making out and just taking our time kissing, feeling each other and swapping oral. Eventually we got to fucking. This was my first flip fuck - I don't recall who topped first but we both went in bare - my first bare fuck as a top. Yes, it felt great raw and my comfort with him helped. I actually got to where I knew I would cum if I kept fucking him but he wanted a break so I pulled out. Likewise when he topped me, bare, it felt nice. Not uncomfortable at all and after a while it started to feel REAL nice and I would have been happy for him to keep going but after a bit he stopped and we jerked off to finish. My first time breeding a guy was with my current BF. I'm the top in our relationship and we've always gone bare since our very first time. Blowing in him is always a great feeling - really there is nothing else like it. In our now several years together he only topped me once, also bare, and he did unload in me. I enjoyed it, felt nice with no discomfort even though I got no where close to a prostate O. I've suggested he fuck me again but he is younger and just views our rolls as rather fixed with me as top an he as bottom. We do have great sex together and we have learned what the other likes.

Uncut is great for sure. Been quite a long time since I've had one to play with. I do feel its removal from me was a major violation of my rights. Sometimes I see guys with a hardcore stance they will never be with someone uncut, its gross, etc. I've been with several and none were ever gross in anyway. Perfectly clean and nice. Usually the glans is much nicer. I see some pics of cut guys which a glans that is so rough and calloused looking - I found that gross. I use a mild face scrub on mine to keep it as smooth as possible. There is a scent that can be present in uncut guys that I find very much a turn on. I'm kind of loose skinned and my head will pull into what remains of my foreskin sometimes and I'll get that same scent which, admittedly, I'll use my finger to indulge in.

The direct answer, mid-40's. I've found this thread fascinating. Maybe there are a few tall tales in here but I suspect most are true. I think my fascination is in how many mirror, at least in part, my own experiences. "Boys will be boys" seems to fully apply. The earliest sexual situations I recall encountering were back when I was around 4 or 5. The first was with a neighbor boy I was sort of friends with who was three years older than me. I'll call him Duncan. I say sort of cause my parent's limited our interaction until I was older since he could be rather rough and tumble. Anyway, he (about 7/8) and I (4/5) were in my bedroom and he convinced me to join him in my closet with the door closed. It was a louvered door so it was dimly lit inside. He wanted for us to pull our penises out and rub them together saying if would do it then I could join a club he was starting and also that he would tell me a story while we rubbed them. I did it, we pulled them out and rubbed them together. The memories are very vague likely due to my young age but it made an impression in that I remember it happened. Next, I was a little older, I think 6. It was summer time and my mother had to have some medical thing done so I was staying with a close family friends who had a boy and four girls. The son was probably 4 or 5 years older than me, so 10 or 11 to my 6. We shared his twin bed and I recall he turned on a reading light and pulled out his dick to show me. He wanted me to pull mine out but I didn't. Again, the memory is vague. He had a hairless cocks as I recall, seemed somewhat bigger than mine but I don't remember much detail. I really had no sex drive or interest at that age. I do recall some neighborhood boys being all into watching other peeing, one time some guys peed in a paper cup then were showing it around. None of that really appealed to me. I was kind of private and shy about bodily functions. Fast forward and I'm 11/12ish. I'm starting to pop boners all the time. Never in the locker room even though I was worried about that. At that age we did need to change clothes for gym and shower afterward. I quickly learned to keep a folder in front of me if I had to walk down the hall boned up. By age 12.5 which was summer, I had sprouts of pubes coming in and had started to play with myself in bed at night. I would play with it until a bit of clear stuff came out and I thought that was semen and that was it. Had not figure out this was precum there was a bigger reward of orgasm and ejaculation I had not yet reached. At this point Duncan and I were friends, but, another guy also three years older than me was my best friend (I'll call him Mike). I hung out pretty much daily with Mike but all three of us hung out together a lot as well. One day Mike and I figured out there were some XXX mags hidden in the house, buried in the back of a closet. We went in there when no one else was home and looked at them for a while. Both of our cocks responded, of course, tenting out our shorts nicely. Putting them back, we went to my room and he suggested we beat off. I agreed so we each did our thing. At one point I suggested we hook up wires from my train set transformer to our cocks so we tried that but didn't feel anything. While jerking we were not directly looking at each other but we saw each other's cocks and took a peek at each other here and there. I knew he had a lot of pubes as I had saw him peeing outside at some point and was amazed (I didn't have them yet when I first saw his). In short order he was showing me his hand covered in jizz, which I had never seen before. I got him tissues to wipe up. I had a little clear stuff come out, not the yellowish/whiteish thick mixture I saw on this hand. After he cleaned up he asked what I did with mine - I don't remember how I answered but there wasn't anything much to wipe up. One evening the two of us camped out in my back yard together. After dark we settled into our sleeping bags in the tent. Maybe more like on them since it was warm out. I was horny and boned so I think I suggested we rub our cocks together. He agreed and we did. I got on top of him and we frotted (not knowing that term at the time). It didn't feel like much but it was exciting. I kept trying to put a flashlight on to see better but he made me turn it off so no one outside could see shadows of what were were doing. We ended up licking each other's dicks but not actually giving each other a BJ. The licking was very brief and didn't feel like much to me. He sort of made a face when he licked mine like he didn't like it. Then we got back in our own bags again and he said we should beat off. We did, he came again although I didn't see his output. He just cleaned up while I was still going. He moved over to take a look and I said, look there is sperm. It was precum and he made a comment about it not being sperm, that it was piss. Soon I stopped and we went to sleep. Next up was Mike and Duncan decided to camp out in the woods behind Duncan's house. During the day I hung out with them at the camp site and they had a good setup - tent, camp fire, cooking food over the fire, etc. all out away from any houses or people. I was jealous that they hadn't included me but later on I figured out why. The next adventure with these two was when they did invite me to camp with them, this time in a "club house" behind Duncan's. It was a small shed not that far from the house but it was relatively private since it had solid wood walls and the window were up higher so when laying on the floor nothing could be seen. Right away the discussion was sexual. Duncan had learned to burn farts so he was basically naked and kept trying to hold matches by his ass and then fart and try to light them. I don't think he every really succeeded that night. Anyway, I saw his very grown up looking private parts for the first time. At some point Duncan decided to recite the birds and the bees to me as it had been told to him by his doctor. I had heard it before but wanted to hear it from him. Eventually we ended up playing strip poker. I lost first and ended up naked with those two looking at me. I sat cross legged leaning down with my elbows on my knees trying to cover up. They made me site up and show everything with Duncan seeing my equipment for the first time and Mike getting a good look for once as well. Duncan sort of teased my small but very hard rod with just a bit of hair growing in. That didn't bother me, I knew I was still growing (and I did haha). Eventually Mike was naked and then all of us were naked, all with boners. I had seen Mike before but like Mike with me, I had more an opportunity to take a good, close look under the flashlight. Mike rubbed his some but then he was getting irritated as it was very late and he was tired. We ended up just going to sleep having just taken a close look at each other. My last adventure that summer was just with Mike in his bedroom. No one else was home and we were in his room just hanging out. I think we had just come back from the drug store where I had bought film for my camera. He ended up with a visible boner and pulled his shorts down, laying on the bed. I took a couple pictures haha but he made me remove and destroy the film. He then suggested we suck each other off. I REALLY wanted to yet I was nervous at his house, unsure if someone came home if we would be able to avoid getting caught. I also still had never cum yet and thinking about our licking session not being that fulfilling, I didn't think the reward outweighed the risk so I declined and said that seemed "gay". I did that summer have a wet dream one night, and having seen Mike's cum, when it happened I knew what it was and was happy thinking that now I can make sperm like Mike. It took a while longer before I finally figured out how to make that happen consciously. One night in bed, I played with myself thinking about this girl in school I liked. I decided to imagine I was fucking her so I rolled over and started rubbing my cock against the mattress. I was pretty gentle and slow so just lightly rubbing it and it felt so good I just kept going for a long time. I started to feel funny in the pit of my stomach but kept going anyway. Then I suddenly had this sensation that something was going to come out - felt like I was going to pee but I couldn't stop it. I exploded! It blew my mind it felt so good. I had stopped rubbing and was catching my release in my hand. I grabbed a sock or some clothes nearby to try to clean up after. When I was done I felt so happy and now knew the trick! After that I started jerking off the normal way lying on my back. Rubbing against the mattress just didn't do it for me after that first time but it at least got me over the hump the first time. Unfortunately, Mike, Duncan and I seemingly overnight had stopped hanging out with each other. Maybe it was the age difference just wasn't working anymore, maybe it was talking about sucking each other off being "gay" with Mike, I don't know. They became best friends and hanging out but I was out of the group and soon had a new best friend my own age and a new circle of guys in my grade I hung out with. I did regret not not taking Mike up on the sucking each other off offer, especially after I had figured out how to cum I wished we could give it try. I figured their sexual exploits continued through high school since they were close friends until graduating when one off to the military. Neither one ever dated or had a girlfriend in high school I knew of. One did get married later and had kids. The other never married and still live with his parent's. Have wondered if he is gay and deep in the closet. I did put everything together regarding the camp out I was excluded from based on some things Mike told me at some point that summer. Essentially, Mike and Duncan had been fooling around together for a while. I don't know how long that was but they were 15 so it could have been for a couple years or so. Duncan had gotten Mike into his closet at some point and they had beat off together and even sucked each other at Duncan's encouragement. Excluding me from that camp out had simply been Mike not wanting me pulled into it. I was on the young side and maybe not ready for that yet. He maybe thought I would blab about the activities or at least be harmed by it if I wasn't ready for it. That camp out seemingly had been all about the two of them getting each other off and then they decided I was ready and they included me in the next one which didn't go into full on sex but was pretty sexual. After all that activity during my 12th summer, I then went into a 10 year dry spell when I finally lost my virginity with a female. I would not be with another guy again until my mid-40's. I rapidly broke the ice then sucking, being sucked, topping, bottoming and having some fun encounters. I do look back still and think about having said yes to sucking each other off in Mike's room. How much may have turned out different - both for better and worse - by just agreeing to that one act. I don't regret any of it, I can't change the past. It is what it is and I did what I ready for at the time. I'm having plenty of fun now so its all good.