Was your first time an unforgettable experience?

I would touch and lick mom’s bare ass at night. She slept with panties. She always smelled like skin so soft. She had a big but lumpy ass. I’d feel the heat off her hairy black pussy.

My first time interestingly happened not long after I was lured to a party in high school just so the popular guys could humiliate me. I was a nerdy kid with glasses and I was always picked on. One weekend there was supposed to be a party for the unpopular crowd at someone's house. Turned out I was the only unpopular guy that got an invite. I was stripped naked and humiliated in front of everyone there. The interesting thing was I actually have a pretty good sized dick even when flaccid (of course at the time I was an outcast type that got zero attention from girls and really had no clue I was above average in that department). It wasn't long after that when of the really attractive popular girls (she was actually lower on the totem pole than most girls in that crowd) started flirting with me. I thought she was just messing with me and trying humiliate me like her type usually did. I think she figured out I was thinking that and she told me the honest truth. She mainly interested in trying out my big dick. I still thought she was just messing with me until one day she pulled me into a janitorial closet and went straight for my dick and gave me head. It was amazing and she got me to nut in her mouth. She said she wasn't messing with me and wanted to fuck me. She invited me to her house one night while her parents were out of town and she rode my dick in her bed she was having the time of her life that night. She kept coming back for more and eventually we actually started dating. She kinda lost her popular girl status because of that but she didn't seem to care. Best experience of my life.

I was a senior in high school, she was a junior. One of the girls that was part of our group had had sex with at least one person, I knew that and really liked her. One day she was in a group that we had a field trip, me and her and another girl friend of hers skipped out on the field trip, found some older guys to buy us some wine, I think they were hoping for some pussy. We went to their place to drink, It didn't take long and me and my friend were in the bedroom, fully clothed, drunk, I think I got my penis in her pussy, hard to tell, I didn't cum.

My first time was when I was 15 and on a scout two day hiking trip with an older boy from school. We walked along through country lanes after his father dropped us off. We talked about girls and cars. That evening we needed to pitch the two man tent and cook a meal which did. At 10 we got into the tent and our sleeping bags. My friend asked me if I masturbated.. I had no idea what he was talking about as I was very nieve and sex was never talked about at home. He said he would show me and sat up removed his pant to show an enormous erect penis he had a foreskin which I don’t. He held his penis in one had and moved it up and after sometime he said he was cumming and great blobs of white stuff came out of his penis. He said it was great and a great feeling. He said he did it most nights. He asked if I would like him to masturbate me. I said yes please and after I removed my pants he stoked my penis for quite a time and also held my balls. He then bent over and sucked my penis I felt this all over tingling and then my muscles in my legs got very stiff he took my penis from his moth and I saw white stuff coming out he then licked that and ate it. That was my first time no longer an innocent young boy. I too have masturbated now most nights since.

FIRST time is never a thing to forget - whether one enjoyed it or not!

I had just turned fourteen when I snuck into this guy's apartment that lived in my building that I knew when he offered to show me some playboy magazines. We went to his bedroom and he took them out from his closet.None of the magazines were playboy magazines, instead the magazines had pictures of kids, boys and girl, naked, masturbating and having sex. I sat off the bed looking at these magazines, that were not in English and in a little while, of course, those pictures worked their magic on me and it make me get horny and hard. When he suggested letting him suck my penis I went for it. I laid back on the bed and I continued looking at the magazine while he opened my jeans and got my erection out. I couldn't hold it back and I just ejaculated completely into his mouth in just a few sucks then it immediately lost my erection. I wanted nothing more but get out of there. He wanted me to suck his but I wasn't horny any more and I had to like promise that I do it next time. He seemed annoyed but agreed and I left. I successfully avoided him for the rest of that summer until school started again. Meanwhile every time I masturbated I thought of those pictures I saw and his sucking me off.

I lost my virginity at 21 and I felt like the 40 yr old virgin by that time because all of my friends had long been having sex already. I was trying to play cool as if I had already but some people could sniff it out... Anyways, I met a cute girl one night at the club and we started dating. Things went slow and date after date, things slowly progressed from pecks to making out to sucking tits and grinding... I probably took too long, but eventually I ate her out. A few nights later, we had sex. I wore a condom and honestly, it was anticlimactic. First time raw, shortly after, was obviously much better. We dated for a few years and I eventually admitted that she was my first and she had an "aha" moment. She was a great girl actually, I could've married her in another lifetime.

An encounter with jailbait or my adult stepdaughter was best overall. Maybe it's the taboo but both are a tie.

Nice !! I feel like I would’ve had a blast with jailbait… Just because of the risks, etc…😮‍💨

The risk was a turn on for sure, and girl was pretty much let me use her as I wished with nothing off limits, and she was no rookie either. I even joked about us needing to make our own porn videos to upload and she said yeah and wasn't joking.

And no, I didn't follow through with that for obvious reasons. Btw I misread the title and added my "unforgettable experiences" in addition to my1st time, but I'm glad you found interest in my reply.