Tell Me About Your First Time

I want you to tell me about your first time. Be as detailed or vague as you wish (preferably detailed, obviously). And tell me about your first time. If you haven't had one, tell me about your fantasy first time.

 

My actual first time is probably the fantasy first time of many other men.

It was back in the early 80s, and I got to meet a woman from the old CB Radio, who had always said that she was going to come & molest me. I naturally considered this to be a matter of all talk - and to be honest, I was probably no different, but when she arrived I was soon to discover that she was serious.

I was 23, and she was well into her mid 40s - plenty old enough to be my mother. She started off by undoing my shirt, but despite my trying to do the buttons back up she could undo them faster than I could do them up (yes, I was still relatively young & innocent, and was doing my best to resist). Eventually I gave in & allowed my shirt to fall to the floor, when she started the same process with my trousers, until I was totally naked, by now with one throbbing, aching erection, which was crying out for some kind of relief.

With a giggle she slipped off her panties, and suddenly my natural instincts kicked in. I lined myself up, but even at this point, in my naivety I was worried if I'd be able to find the right hole - thinking that there had to be 2 - one for the penis & 1 for urination.

As I & thrust forward I remember being overwhelmed by the thoughts racing through my mind as I knew that as of this moment I was no longer a virgin.

Even at this point my mind was thinking logically & considered that the physical act had to be no different to that of masturbation, as I set about pounding away, to a similar pace. Needless to say, within a matter of seconds she was crying out at me to 'Take it easy', at which time I slowed right down, letting her body language be my guide. I didn't think it wass possible to go that slowly & still manage to reach an orgasm, but I was to be proved wrong - probably the most valuable lesson in sexual technique I've ever learned to this day.

I know that technically this was a clear case of abuse, and that I was raped, plain & simple (even if it was a case of a woman raping a man), but with hindsight I am forever grateful that it happened as it made it so much easier to approach partners for sex, as well as to recognise the indications that potential partners were wanting to approach me for sex. I suspect that if it hadn't been for her, I may have remained a virgin to this day.

 

How so?

She didn't force you. As far as I can tell, you could have stopped it.

 

As I stated in the 3rd paragraph, I did try to stop it, albeit unsuccessfully.

"I was 23, and she was well into her mid 40s - plenty old enough to be my mother. She started off by undoing my shirt, but despite my trying to do the buttons back up she could undo them faster than I could do them up (yes, I was still relatively young & innocent, and was doing my best to resist)."
​

To be honest, if she had simply asked if I wanted to have sex, I would have been up for it, but the aggressive approach totally changed the scenario.​

 

Whoa, I completely missed that - sorry man.

 

hooked up with a girl from school. im an idiot -_-

 

I'm guessing that backfired somehow?

 

i should have waited to do it with someone i liked

 

Was 'okish' didn't enjoy a lot ... it was with a random girl I hooked up in the street. Funny bit was that both my knees were roughed up pretty badly from friction with the bed sheet

 

Given certain... particulars of my first sexual experience (namely, that I was very much underage and he was really not), I don't know how explicit or detailed to get here, due to the possibility of it being deleted/me being banned. If I know that's not a problem, I'll post the story in greater detail.

 

It's not a problem; being that it isn't pornographic, but biographic in nature.

If it were a problem; deletion would be the proper course of action for a mod to take, anyways.

 

Well I am 22 and I have never had sex, it sucks, there were some girls in high school that I could have done it with but I was too timid to do the dirty deed.

And I will admit that I have no clue about how to sensually bed a women.

 

Okay. Here we go. I'll post it, but if any part of it is objectionable, just inform me and I'll remove that part. I've tried to make it as non-explicit as possible. This may make the story less interesting, but it will also hopefully make it less likely to be deleted.

Ever since I'd hit puberty, I had been interested in sex, (which was itself somewhat amplified by my having discovered some porn of my parents while snooping in their bedrooms one day) and I quickly realized that my tastes, when it came to men at least, ran exclusively to older guys. In middle and high school, I had no interest in guys 'my own age', finding their rather severe immaturity to be a turn off, filling me with the same revulsion and disgust as one would get from seeing a maggot-riddled corpse. There was only one around my age I could stomach being around even as a friend for any length of time, and even then I could not fathom the idea of being with him sexually. My desires, it seemed, were only for guys significantly older then myself, mainly it seemed in the range of 10-15 years my senior. Also, at the risk of sounding immodest, I have always been of a higher than average intelligence, and thus was isolated, intellectually, from most of my classmates, more on the level of the adults around me. I had also been praised for apparently being extremely mature for my age. These may have been contributing factors to my particular attractions.

This leads into my first time, which occurred while I was out of school for the summer between my 7th and 8th grades. Living down the street from me at the time was a guy I was a bit in lust with. At 25 years old, he had long dark hair, a nice body, and played guitar in a local rock band in his free time. He was also a sweet guy, with a sarcastic sense of humor, and an interest in comic books, science fiction, philosophy, science, classical music, and the alternative and grunge bands of the time. All things I liked.

As mentioned before, I quickly found myself quickly falling in lust with him. I desired him, wanted him intensely, and I knew that I wanted him to be my first sexual partner, and began planning how to make that happen. As such, partially out of a genuine desire to learn, but primarily to have an excuse to hang around him while I plotted my moves, I asked him to teach me the guitar.

As a result of this, I learned that he hadn't had a girlfriend in over a year, and saw that as a potential opportunity. I offered myself to him sexually. I came on to him directly, letting him know what I wanted, and that I was available for the taking. He turned me down, citing my age, and while flattered, he told me I should find a guy closer to my own age. As I stated before, I didn't WANT or LIKE boys my age. Again, they were immature, considering the height of wit and humor to be belches and armpit noises, and not the kind that one could forge a true connection with. And while I have long possessed the ability to separate the physicality of sex from emotion, and have never really been hung up on the idea of love or romance. And while, even then I was completely comfortable with the idea of a relationship based primarily upon sex, I did prefer to be with someone I who was closer to my own intellectual level and whom I could at least forge a connection with. Even today, this is a difficult thing to do. It was pretty much impossible then, especially within my own age group at the time. I also wanted someone who knew what he was doing, knew how to please a partner sexually, not some fumbling, over-eager virgin. I wanted someone who was as interested in my pleasure as their own, which, according to some of the other girls at my school, the boys in my school clearly were not, instead only concerned about their own gratification, with their sexual partners becoming little more than masturbatory aids.

With all this in mind, I didn't let his rejection deter me. I stepped up my attempts, started wearing sexier clothing when I visited him, made sexually suggestive comments, rubbed against him 'accidentally' and so on. On more than one occasion, I felt him develop an erection as I subtly rubbed my ass against his crotch. I knew I was breaking down his resolve, slowly but surely. This went on for over a month, even as I crossed the threshold into my teenage years. The first real success to my plan to losing my virginity came a week after I turned 13 years old. I had spent the day making my usual thinly-veiled sexual comments, wearing a tank top without a bra, and even 'inadvertently' exposed my breasts to him, and I could tell he was starting to reach the breaking point.

We were sitting on the couch when I kissed him, and I rubbed my hand over him. I told him I wanted to have sex with him, that I was here for the taking. He said no once more. So, I instead offered to perform oral sex upon him. After initial resistance and reluctance to the idea, his libido finally took over, and he consented to the idea. For nearly 10 minutes, I did so, copying what I had seen on those porn videos I had previously discovered. I brought him to climax and completion right there on his couch, and I found that I utterly enjoyed doing so. Afterwards, he felt guilty for giving in, and swore that such a thing would never happen again. I, on the other hand, knew that this was merely the beginning, the first step to fulfilling my ultimate desire.

From then on, I discarded any pretenses for wanting to be near him, focusing instead upon reaching my goal. Guitar lessons forgotten, I continued my advances upon him, and we wound up spending almost our every moment together making out, and with me continuing to perform oral sex upon him. Each time, I'd push to move it further, to have sex with him, but he'd still refuse. After a month of such, I finally broke through that last barrier, and we finally wound up fucking. I lost my virginity to him in his house, on his couch and in his bed. The experience was incredible, and even better than I had anticipated. He was a remarkable lover, sexually attentive and making a concerted effort to ensure my pleasure and enjoyment, resulting in my achieving a climax at least twice. It was a remarkable occurrence incredibly satisfied, one that was everything I wanted. We spent several hours together, before we concluded that encounter and I slipped home just before nightfall.

It did not end there. We continued to get together repeatedly over the remainder of the summer, primarily consisting of oral sex, although with two more encounters going 'all the way', so to speak, including my first experience with anal sex. Shortly before I began 8th grade, he terminated our encounters out of fear of getting caught. I moved on to other similar relationships, and he got into a real relationship that he didn't have to hide. We, however, remained in contact with each other, continuing our friendship for a few years afterwards, until he moved, and it remains one of the best times of my life and fondest memories. I've considered looking him up again over the years, but never really had the time.

 

my cousin invited me and an older office coworker up to Big Ben for the holidays. on the way up we were cramed into a little car and she sat in my lap- dam that warmed my crotch. later that night while everyone was asleep, i snuck into her room and started kissing her. ,then her boobs. she pushed my head lower so I pulled her panties off and began licking or chewing the hair looking for the pussy. but got lost in the forrest and gave up.

 

Wow! I'm surprised such an amazingly detailed memoir of sorts got totally ignored in the way of responses!

 

I bought a king can to some girl in a park when I was 13

 

I lost mine when I was 19.

I was a freshman in college and used to fly back to the east coast (I live on the west coast) 2-3 times a year to do art direction for Star Trek conventions. I met a girl my age who lived in Philadelphia who was also a convention staffer and we really hit it off. By the end of the first 4-day convention, I was playing with her breasts (thru her clothes), but we went no further.

On the second trip back east, we got together again and picked up where we left off. The second night, she offered to sleep with me. We went back to my room, quickly undressed each other and, with very little preamble, began fucking. We spent the rest of the night in my bed, but didn't do anything else, because my roommate showed up shortly after we finished fucking the first time.

When I woke up the next morning, I petted her breasts and fingered her pussy (under the covers) for a while, but she finally stopped me. Later that morning, when we had a quiet moment on the convention floor, she told me that she made me quit because she was getting too aroused and was afraid she'd lose it and fuck me right in front of my roommate (which she didn't want to happen.)

The next night, we ended up in her room and fucked some more, but also had to quit before too long because HER roommate showed up. In spite of the interruptions, we got in a good hour each night of clumsy kissing, petting, sucking, and fucking (clumsy because we were both virgins.)

After that convention, I flew home and we were never together again. Even now, over 35 years later, I really regret that.

 

Did you wear your Spock Ears?

Stay Brown,
Rev J

 

Nope, but I was surrounded by HUNDREDS of them. Ever seen the movie "Galaxy Quest"? Yup, just like that. :smoking:

 

My first time? Ok dont laugh or critisize. I was 13.... about 2 months away from turning 14. I had just ran away from home and walking down the avenue... then two guys pulled up next to me complimenting me on my looks and such. They were both pretty cute. So they asked how old I was, me being the immature kid I was, I lied and said I was 15 about to be 16. They asked if I wanted to come party with them and I said yes. What the hell else was I gonna do anyways. Soooo we went to the store and they picked me up my own 6 pack. We went to an orchard and me and one of the guys stayed there and drank while the other one had to go give someone a ride real quick. Well I had never drank so I got wasted pretty quick. We started kissing and were kidding alot. He nibbled my neck some and that gave me goosebumps but I was already cold so it didnt help my chills. When his friend finally got back him adn I went back to him and his sisters place. She asked how old I was and I said 15, she snickered and said "yep my brother likes em young" He was 23 at the time. Anyways we got super wasted and I ended up literally not being able to stand, I had to crawl haha... so I crawled and layed next to him on the floor. It was March 10th, 2004 around 3am and we attempted to have sex. He had no idea I was a virgin. He first fingered me which felt great.... he only used one finger and complimented at how tight I was haha! He then went down on me and I was in heaven... it felt soooooo good! We then tried to do it, and I began to cry cause it hurt SO bad. He only got it about an inch in and he couldnt continue because I was in so much pain. Then I told him I was a virgin. Later that night I asked him if it would huirt as bad the second time. So the next night I took him into the bathroom and began sucking his dick (he had the tattoo "Your Name" on his dick... comical) and so we went at it again on the sink. This time he got it all the way in. But it didnt feel good, it was insanely painful but I let him go till he came. The third night was good. We began to have sex and it didnt hurt as bad.... and he held me so close as he thrusted in and out of me. And I grabbed him... tight. I had no idea I was clawing the shit out of his back... he thrusted so deep inside me. He then flipped me up to be on top of him. Thats when it began to hurt ALOT... but he held my hips tight so I couldnt get off and told me to just go with it. It was painful but I felt so sexy and I knew I was pleasing him so I did it... it was such a painful pleasure... and I loved seeing him get off with every cry of painful exstacy. It was nice. I havent seen him since, but having to leave him sucked. When I came home I was COVERED in hickies... and my mom knew what I had done. But for the almost 2 weeks I was gone, him and I fucked everyday sometimes more than that. I will never forget him.