First time sexual intercourse or penetration stories...

[WhO2]

From what I read on other similar threads, I think the hairbrush is fairly common. Thanks for sharing.

 

[Sgts19]

Not off to a good start. My HS girlfriend and I had gotten each other off many times, usually in the room besides where her parents watched tv.....Always made sure that I wore a long tee shirt...cum stains in my pants. When they weren't around, we'd practice oral sex on each other...her sister did catch us once..not good lots of crying...sorry but it wasn't a Lit moment that her sister climbed aboard. We'd been talking and talking about the big deed (mostly me) and finally decided we'd go out behind her property. Woods and fields. We stripped down and fumble around until we get off. The bad/sad thing was we were laying in poison ivy, lucky my dick and her pussy didn't get it. She ended up going to the hospital needing antibiotics. Me I found out I wasn't allergenic to the stuff. 2 Great things to remember about her, getting caught in a 69 by her sister and fucking in a patch of poison ivy

 

[YourSecretDesires]

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.)

An lover of mine and I got to talking about our masturbation experiences. Then we decided to have fun and show each other. She got out a hairbrush and fucked herself with it like she used to. I showed her how a guy might fuck sofa cushions. She also rubbed her pussy on the arm of the sofa. It was a really cool experience.

 

[Fisher0382]

My first time was with a girl that we were actually broken up at the time. She asked if I wanted to go out to lunch so I went over to pick her up and noticed her parents or sister weren’t home. At lunch she said they were away for the weekend and if I wanted to come in and watch TV I could. So we sat on the couch and she started cuddling up to me. I could feel her big tits rubbing against my side. I went in to start kissing her and we started feeling up on each others body. We got out of our shirts and sucked each others nipples. I got completely naked first and she started sucking my cock as I played with her tits. I then told her I wanted to try eating her out. So she stood up and showed me the thong she wore that day before exposing this hairy red headed bush. I didn’t go down on her for long because I had no clue what I was doing and I don’t think she was enjoying it. I then luckily had a condom in my wallet and I fucked her on the living room floor. She bled a little and she had me pull out before I came which didn’t take long.

 

[Ramone45]

It's my wife's favorite story to share with me. She and the young man were entirely over the age of consent.She had given lots of head, but had not been penetrated. She was mega hot, but not pretty in the traditional sense and she was very tall and skinny. She never wore a bra, so her nips were always visible under her shirts. She was the last of her group of friends to lose her virginity. She said she was really ready. It was at a party and it was kind of set up in advance. The girls trusted this one particular guy who took the virginity of most of their group, including my wife's sister! She said they got high and went into an adjacent room. She said it was really good. She said they were making quite a bit of noise and she was self conscious about that. She told me he was good. He had a big dick. He ate her out to get her ready, but she said she was already dripping. She enjoyed the feeling of connection to a man. She said no other man could have what she gave him and she will never forget him for making her a woman. He inseminated her, which she enjoyed. She wanted to be claimed by him. She also felt more a part of her group of girlfriends after she had been fucked by the same man that fucked them. Sh was flattered because a couple of years later, he contacted her and wanted to fuck her again, but she had another boyfriend by then.

 

[Lucy_Lastic]

That's a story I can't tell due to age.

 

[Ramone45]

That's a story I can't tell due to age.

You can lie.

 

[Lucy_Lastic]

You can lie.

when I was 18 I was groomed in a video chatroom. Happy?

 

[Wonderer67]

I was working at a restaurant and there was this cute salad prep girl. She had a reputation for being pretty slutty but she was cute.

We started hanging out with each other and then a couple of nights later we wound up in my bedroom after work. She was far more experienced than I was altho she was a year younger. I did not really know what I was doing.

I went down on her because that seemed like the right thing to do. Then I entered her and went all the way in. I will never forget that feeling.

I had the opposite problem of premature ejac that night. It took me a long time to cum (esp since I was a bit nervous). So we fucked for quite a while and we tried a few positions. We started in missionary, then she rode me in female superior. I think she was waiting for me to cum.

Finally, in doggy style, I blew my load all over her ass and back.

It was prob not my best moment.

But she was nice and understood. We fucked for a few more months after that.

Swear to god, as I was walking her back out to her car, she started it up and Meatloafs paradise by the dashboard light was on. We got a good chuckle out of it and a nice long goodbye kiss.

 

[magicalmoments]

I know I've told this story before. Let me start by assuring the moderators that we were both of legal age.

My first was the woman who was to become my first wife. We'd been going steady since the graduation year of high school. We'd been "heavy petting" for some time, although that was pretty one sided. I would finger fuck her but she only rarely touched my cock and had never given me a hand job or caused me to come. I know she ever orgasmed from my fumblings although she did get very wet. Anyway... I suggested we have sex, she was reluctant so I pressured her a little. I said "Look either we have sex or I go find someone else to do it with." Yes, I was a real asshole! She should have told me to piss off! But it convinced her and she gave in. It happened in the shrubbery of a local park walking her home from the movies. It was a cold windy night, her with her dress pulled up to her waist, panties removed, lying back on her overcoat. Me with my cock out of my fly, trousers still on, condom slipped on. I lowered myself over her, thrust my dick into her, not without some difficulty, she let out a squawk of pain, I thrust maybe half a dozen times and shot my load. 30 seconds of absolute bliss. I was the man! So that's it, my first, a date rape situation. Jesus I was a bastard.

 

[hiker283]

My first time was on our wedding day and was fantastic. I could not believe how good it felt. Of course I came too soon. Next time, a couple hours later I did much better and she climaxed.

My wife's first time turned out to be around a year earlier. While I was away for what turned out to be the summer and all of senior year she met a guy. She enjoyed his company and they ended up making out and then with her dress around her waist they dry humped. Three weeks later they were fooling around. She was wearing the same dress and this time he got her panties off. Pretty soon he had his dick in her. She had sex with him quite a bit and then with some other guys before I got back. I did not find out about it until a few years after we got married.

 

[remypare]

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!

My first time was...not great, but funny. My girlfriend and I had been messing around for a while and had planned out the first time we'd have sex. We made out for a while, got naked, and decided...it was time. Put on a condom, she laid back, and we rubbed my cock along her lips and experimented until we figured out where it went...I, sadly, lasted about five seconds and came almost immediately -- she was not 100% satisfied with the encounter for obvious reasons, but I guess the first time is probably awkard more often than not.

 

[Lucy_Lastic]

I know I've told this story before. Let me start by assuring the moderators that we were both of legal age.

Nobody on earth ever lost their virginity below legal age.

So that's it, my first, a date rape situation. Jesus I was a bastard.

So why are you proud of it?

 

[magicalmoments]

Nobody on earth ever lost their virginity below legal age.

So why are you proud of it?

Goodness. Whatever is there in my confession that makes you think I am proud of my actions?

 

[Lucy_Lastic]

Goodness. Whatever is there in my confession that makes you think I am proud of my actions?

The fact that you feel the need to repeat it.

 

[magicalmoments]

The fact that you feel the need to repeat it.

You are of course entitled to your opinion, even if is poorly formed and ignores the facts placed in front of you. I can assure you, I'm not proud of myself. I take the view that confession is good for the soul.

 

[UtilityCurve]

I guess the first time is probably awkard more often than not.

I'd say awkwardness is all but guaranteed for a virginal participant and the odds become overwhelming if both are.

I gotta believe that most guys made Minute Men look like patient lovers. Honestly a shame for the girls, but if they had pain or discomfort, perhaps this is a case of "if it were done, it would be best done quickly."

I have read many, many comments from women that started "The second time went so much better."

 

[Serge69]

Not very spectacular compared with other stories or other people's backgrounds here, but here goes in my case. Mind you, this happened 50 years ago, so mentalities and the World were quite different back then.

Here I was, 22 and still without the experience of penetrating a girl. I was from a very catholic and repressive milieu where in my days we attended gender-segregated schools. I had a girlfriend who was VERY prudish: no kissing for at least a year after we started dating, to give an idea; shouuld have been a huge huge red flag, but I stupidly put up with that. I was now in Central Europe, where the post-war rebuilding was still ongoing; I got a seasonal job in a factory, far from overbearing family and society. People were nice. my foreman would warn me against girls who seemed attracted to me who were known to have VD that's how STIs were called back then). A few (female) students joined our assembly line for the summer.One of them, a 19-year old, took a liking to me, which was reciprocal. Did not take long that we were confiding in each other, hanging out, going to movies, etc. She once told me at break that she would love to do petting with me. She also had a boyfriend, who was getting jealous and in the process of progressively dumping her; weird guy, who had insisted that she sould have sex with him if she loved him, etc., but who, after she had sex with him, called her a whore for having pre-marital sex and that he could not trust her not to have sex with other guys if they were to marry! One more boyfriend with whom she had had sex and dumped her shortly thereafter.

To get back to the point (sorry, I felt the need for some background), she knew I had never had full sex with a woman, so she was very eager to help me with that aspect of my life. We had previously had a few heavy petting sessions, but now that the boyfriend was no longer in the picture, she was more than willing to go ahead. We finally got on with it in the relative comfort and quiet of my assigned quarters at the workers' residence. She was quite pretty, with long, curly auburn hair, B-cup or so firm breasts the colour of milk, topped with ruby-red nipples surrounded by lighter coloured areolas about 4 cm across. Her pussy had ruby lips hiding beneath equally auburn curls, lovely sights all. Her pussy juices were abundant, and with a very pleasant taste. Somehow, she had sad-looking eyes. I lit some candles, we proceeded to kiss and caress each other, slowly and progressively unbuttoning and opening items of clothing, before taking them off completely. When came time to free my very hard cock from its confines, she gasped; I was no John Leslie, but still packed a bit more than 16cm, with about 13cm girth. She called my cock a little giant, and said she had expected it to be smaller since I was a virgin! I was now rubbing my cock alongside her slit, while also stimulating her clitoris. Penetration took place, a new senasation for me, actually a unique one since I never again had the type of stimulation her vagina was giving my cock, as if it had been sliding just beneath the skin of her lower stomach. So wet and warm was her vagina, clasping my cock and generating such pleasant sensations. I was starting to feel that I was about to cum, and I warned her, since at the time she had just sarted to take the pill a few days earlier, relyiing on withdrawal until then. We did not want to take any chances, so I withdrew, which summoned quite a bit of willpower, and shot on her lower belly. I still kept stimulating her with my fingers, wwhile kissiing her, nibbling at her nipples, licking her neckline, when all of a sudden she gasped and thrashed about. After she sttled down, I asked her whether she was OK; she replied she had just climaxed and thought she was going to die! Confided this was the first time someone else made her cum!

We kept seeing each other for a couple of weeks, until I had to vacate my quarters during the factory holiday season, and she was going on an apartment-hunting trip in the town where she was to start Uni.

I had left some luggage in storage at her place so I could travel light for the next couple of weeks before returning home. When I got back to her place to retrieve the luggage, I asked her dad if I could see her; he rolled his eyes, smiled and, shaking his head, informed me that she now had yet one more new boyfriend, a Japanese this time. She called out for me to come to her bedroom and meet whatever his name was.

This, and another experience helped me tremendously when came time to have first sex with my wife. I never told her, but she should be extremely grateful to those two other women... like I am!

 

[SubmissiveSnowflake]

Mine hurt like hell. It was me who initiated it the second time though. I had used a hairbrush for years before having sex, but it was impossible to relax with my guy that first time in the same way as I would automatically relax with my brush or fingers.