First time sexual intercourse or penetration stories...

[WhO2]

Before I started a new thread, I searched to see if there was already something similar. I searched for 'virginity' and found a few threads, but it seemed like that term also caused some heated discussions.

So, hoping to clarify:
- men or women, the first time you had (or tried to have) intercourse, how did that go? Was it romantic, or back seat of a car, or something else? Was it painful or messy?
- women, if the first time penetration was not during intercourse, what was the situation (and object)?

Details make stories interesting, so give us the full story!

 

[WhO2]

My story is pretty long, so I wanted to keep it outside the original post.

My first girlfriend (gf1) let me watch through her window while she changed, gave me my first blow job in the living room while her parents watched TV in the den, and occasionally got naked with me, but she was not ready to go all the way. Eventually I met the girl who would become gf2 and broke it off with gf1. Gf1 thought intercourse would save us (it wouldn't have) and came over to do it. Being a horny 18 year old I would have happily done it except...

My parents adopted 2 kids from another country. I told my sis under no circumstances was she to come to my room. Unfortunately, he English was very limited. I am pushing, just seconds away from bliss, when sis knocked on the door. Ex-gf1 got scared, dressed, and left.

A few months later gf2 decided it was time, and we planned all week. I was majorly in love with her and so ready, but we waited until late in the night. Her curfew was too close, and the pressure was on, and the pressure to get it done in time for curfew led to stage fright. Arggghhhh!

Next week was her period, so we had to wait an extra week. It finally happened, and I remember it was a struggle to get in but there was no mess it was definitely worth the wait after all the delays.

 

[TinaG_2023]

I really wanted to do it but it certainly wasn't something worth writing an erotic story about!!! I'm sure nobody forgets that first time!!

 

[Ssbbw4u1974]

https://www.literotica.com/s/memoirs-of-my-sexy-life

All true..
My only non fiction

 

[Lucien_Al]

https://www.literotica.com/s/memoirs-of-my-sexy-life

All true..
My only non fiction

Wow that was a hot read. I loved it.

 

[TheDubbs]

It was a nice surprise. We were trying specifically to save actual penetration until after our wedding, but we did basically everything else you can think of. So we were both naked, spooning, and of course I was hard as a rock pressing into her ass. We’d done that many times, and usually she’d reach back and stroke me while I would rub between her legs.

This time though, at one point I got a little too eager, and at the same time she pushed it further down between her legs than usual, and it slipped in. And I mean, she was so wet, it slipped ALL the way in. We both just froze for a second as we realized what happened, neither of moved a millimeter. Then she suddenly moaned and started pushing her hips back against me slowly.

It was the most incredible feeling ever. I think I lasted literally about 3 seconds after that, and could not BELIEVE how good it felt. I came inside her before either of us could stop it.

Thankfully she was not ovulating and we lucked out. We of course fucked all the time after that, but were more careful until after the wedding. But holy shit, I will never forget the feeling of that first time feeling her push against me as I emptied my load deep inside of her. I can’t help but stroke myself right now just thinking about it!

 

[Not Normal]

The first time for both myself and my first serious GF was actually a fail. It was at my house. I think my folks were out of town. We'd made this plan. I bought condoms and didn't realize they were 'snug' fit. Between then condom feeling really tight, and the general nervousness of us both, entry wasn't achieved. We decided maybe we weren't ready. For the life of me, I can't remember what time of year it was, but I think it was still winter. Maybe February.

I do know the date it finally happened. April 1st. We were at her house this time, and her family was out, possibly a birthday thing? I don't remember, but we had the house to ourselves. She had gone on the pill by then, so no condom related drama. We felt comfortable and enjoyed ourselves quite a bit. I don't recall it going all that long once I was in. I know she'd cum from my mouth already. I remember lying there with her, and we both had this really satisfied feeling. We basked in it, proud and in love.

We then met friends and went to the Midnight showing of The Wall.

 

[Rackson]

My first time was a disaster. She bled as I broke her hymen and I freaked out a little. We were at a friend's house party and ruined the bedsheets!

 

[Pabiporffor]

There's tonnes of first time stories on lit and although the vast majority are fictional I think most writers tap into their own first experience for inspiration.

 

[DEPRAVED_WHORE]

Just so I don't break any word count rules....with older guys, rough, painful, degrading, survived, powerful because of it.

 

[YourSecretDesires]

I'm the rare bird who doesn't remember much about his first PIV intercourse. It was just another thing to me at that point and there was nothing special about the girl or circumstance. I consider my real first time to be when I got a blow job. I know that sounds odd to some but just how I see it.

 

[jays78]

https://www.literotica.com/s/memoirs-of-my-sexy-life

All true..
My only non fiction

Really sexy stories.

 

[soflabbwlvr]

I have told this story on other threads, but it has been a while, so I will present it again. I was in high school at the time. Over the previous three years I had spent every waking moment trying to get laid. It was an obsession. My girlfriend was also a virgin, and tightly clinging to that status. Over about a 6 month period she gradually relaxed her boundaries, and eventually we made plans to cross the final frontier. The problem we faced was where to go? Eventually we made plans to meet at our high school tennis courts. It was summer time, so we both wore shorts and t-shirts. We played a quick set, then took a walk in the woods behind the school. We eventually found a secluded, grassy area. We took off our shorts and underwear, laid down in the grass, and got busy. It was simultaneously the most exciting and disappointing ten minutes of my life. I put on a condom, worked my cock into her, and thrust until I came. I know she got very little out of it. Neither of us really knew what we were doing. Thrusting was easy, but I had zero technique. She just laid there, totally clueless about how to participate and enjoy the experience. (I'm not blaming her -- she had no experience to draw from. We were both inexperienced). She bled a little, but the most memorable thing about it was the mosquitos. They were vicious. Her legs and my ass were destroyed by mosquitos. When I finally filled the condom with my cum, we immediately jumped up, got dressed, and headed back to the tennis courts. No relaxing and reveling in the moment. Getting out of those woods felt like a matter of life and death.

 

[Lucien_Al]

My first time was pretty unexpected and eventful for me but I suspect not very eventful for my partner. I was desperate to lose my virginity and up to that point had gone down on my previous girlfriend and she had given me a few hand jobs but nothing further.

We were at a school dance when a crowd said they were going to go for a walk. A few of my friends indicated that this was their speak for some fun in the local churchyard. I was no longer with my girlfriend so tagged along to have a few beers. When we got there one of the girls from my class was there too and seemed to be alone.

We sat and chatted for a while and she told me her boyfriend was at boarding school. I was feeling brave after a few beers so leaned over and kissed her. She kissed me back quite aggressively which surprised me as I was expecting the normal rebuff. This progressed to me feeling her tits under her shirt (I might add they were the biggest tits I have ever seen, felt or sucked) and once again she did nothing to stop me and seemed to be really enjoying it. I eventually put my hand up her skirt and rubbed her pussy over her panties and once again she did not stop me and by this point was rubbing my cock over my jeans. I clearly remember how wet her panties were but at the time I was ignorant as to why they would be so wet.

She eventually slipped her panties off and unzipped my jeans, freeing my cock. After a few sucks she lay back and opened her legs guiding me into her. I think I must have been in and out before I came into her pussy. She showed little emotion and just cleaned up with her panties and threw them into the bushes. She said very little that evening and we ended up calling it a night. I felt like the king of the world knowing that I was no longer a virgin.

She never referred to it ever again but I did sweat a little when I thought about having cum inside her with no protection. The possibility of her falling pregnant never occurred to me at the time.

On hindsight I feel quite ashamed that I gave no thought to her pleasure.

 

[gtnlynn]

My wife was playing strip poker with her brother, a neighbor boy, and her best friend. My wife stole some cigarettes from her mom's room so they could be really "bad" as they played cards. My wife lost and had to strip naked. The neighbor boy threatened to tell her mom about the cigarettes if she didn't let him stick his cock into her pussy. She protested, but her brother and friend were in favor of the act. So she let the neighbor stick his cock in her and give a few thrusts before she pushed him away. My wife refuses to talk about it. Her friend and brother are my sources for the story, which she agrees is basically true.

 

[awired50]

My first time was at a friend's house on a twin bed. There were 3 or 4 others outside the door listening!

 

[Tessinwales]

I did write an account of my first time, but it was rejected because I was under te legal age of consent. I understand their reasons.

 

[vibes]

I did write an account of my first time, but it was rejected because I was under te legal age of consent. I understand their reasons.

And you can't be arsed to edit it?

 

[Tessinwales]

And you can't be arsed to edit it?

Not at all, but by editing my age the whole feeling and emotion of it would change into a very different thing.

 

[Hipshot1554]

Not at all, but by editing my age the whole feeling and emotion of it would change into a very different thing.

So many stories can't be told...

 

[Inthelastrow]

First time was with a slightly older woman during college. Both of us were camp counselors at a church camp in Northern Wisconsin. We had the hots for each other all summer, but we didn't "do it" until camp was over at the end of summer. We both stayed to help close up the place. The camp manager closed all the cabins but one so we had to sleep together in the same cabin. That of course led us to having sex for the first time. Since it was both our first time, we were nervous and fumbled around a bit but eventually figured it out. It was quick (on my part), intense and wonderful. We left for college two days later and never hooked up again. Ah, such memories.

 

[Up4fun&69]

It was strange. I was strange. (Some say I still am.) Freshman year at college (I started at age 17) was interesting. Small SoCal Division III college. I played football. Had a car. Had a much sought after, high-profile college job, as well as a part-time (20-30 hr/week) job off campus. I got my father's genes and could hold my liquor very well. I had my own room as my roommate left after one week. I was considered good looking. And I was voted BMOC (big man on campus), before the first term ended. I was popular...but I was also VERY shy. (Still am to some extent.) From the first college dance and all the parties that followed (late 1970s), I had several coeds pursuing me but I was too shy to ask them out. I made female friends easily but the shyness was crippling when it came to dating. So with all of that, I remained a virgin. It wasn't until the beginning of sophomore year that things changed. The women, younger and older, figured it out and started asking me out. One busty classmate came from money, was bossy, and got whatever she wanted. And she made it clear the she wanted me. We went out to dinner a couple of times and then she asked me back to her place. The trouble with her place was that she was 2nd in charge of the college's biggest sorority and, technically, overnight guests of the male persuasion were not allowed. And if a male was in the house for any reason, he was not allowed to go about unescorted. So, she all but sneaks me into the house, very quietly as it's already late at night. We start making out, the clothes come off, and we have pretty wild, hot, sweaty, bed banging animal sex. My "V" card was punched. But of course, all of that loud sex meant that the adjacent neighbors, if not others in the house, heard what was going on. And when it was over and I needed to take a leak, in rumpled clothes and reeking of sex, she had to escort me down to the bathroom on the main floor...down past just about every other room with her sorority sisters either clapping or making snide comments as we passed their open doors. Very strange night. But it wasn't the end. A few weeks later, she calls and tells me that she's late. She did tell me that night that she used birth control and that I should go bareback and cum in her. But later she tells that she only uses spermicidal foam and, in those days, it's only about 70% effective! This went on another few weeks and I told her that I'd accept whatever decision she makes, thinking that my fate was sealed. Then, just as it was a month later and she was going to the doctor, she had her period. Talk about dodging a bullet. The thing was, after the loud sex and the "perp walk" to the bathroom, then not running away with the pregnancy scare, and word of mouth amongst the "sisters" and their friends (remember, it was a small college), my reputation among the coeds soared and I had no trouble getting dates the rest of my college life...even though many of them were the result of the girls asking me out as I was still somewhat shy. (Now, asking older women out from my off campus job was another story. Not shy there. Go figure.)

 

[WhO2]

Some interesting stories here. It seems like as guys we didn't do a great job of making it good for our partners. Also, looks like many of our first places weren't too good, either.

 

[Inthelastrow]

Some interesting stories here. It seems like as guys we didn't do a great job of making it good for our partners. Also, looks like many of our first places weren't too good, either.

My first place was wonderful, a log cabin the Wisconsin woods, late summers. But yes I didn't do a great job of making it wonderful for my GF. I have to say that youth, first time beginner and total excitement combined and left me concentrating on my actions, not her reactions. Kinda like the old bugs bunny cartoon where the dumb wolf wants to use a grenade and has to read the instructions only to find out that he has less than 10 seconds to pull the pin and throw the grenade. It took about ten seconds and I was still trying to figure out what to do. I am happy to say that I quickly learned to shift focus off me to her and I am a far better man for it.

 

[BongoGal]

- women, if the first time penetration was not during intercourse, what was the situation (and object)?

I 'lost it' to my hairbrush handle. I still hear stories about other women having similar first times with hairbrushes. (Back in college, I remember a friend bringing a gag gift from home that was a brush with a realistic phallic handle. I always wanted one.)