Story Of My First Time Masturbating...With A Girl! lol

Since I got so many views (but oddle enough only one reply lol) to my story of my first masturbation, I thought I'd tell more.

Ok, spring 2004, my best friend loses her virginity to her then-boyfriend. Early summer of that year, they break up, but she keeps telling me about how much she loved sex, how much he made her cum everytime they did it. We both knew, & know, each other VERY well, & 1 of the things we knew about each other is that we both masturbate. She suggested we try it together. I still hadn't gotten my first kiss yet, let alone seen a topless or naked girl in real life lol. I was a little worried about it ruining our friendship, but I was also really horny & so was she, so I thought "why not?"

We went up to her room when no one else was home. She was wearing a tank top & shorts, & was barefoot. I was wearing a tshirt & jeans, & I was barefoot, too. (BTW, she knows about my foot fetish, & shes always barefoot almost all the time, & shes played footsies with me MANY times, just because she knows it drives me nuts lol).

Anywho, we lay down next to each other & we agreed that we wouldnt look at each other nor touch each other. For me, though, she agreed we could play footsies while we do it, & our bare feet were rubbing together & our toes were interlocking the whole time we did it. She put her hand down her shorts & I took my dick out of my jeans & started stroking it. As if I wasnt hard enough from those soft feet rubbing on mine, now I was hearing her moaning which made me even harder. After awhile, she leaned up & took her top off, then laid back down next to me & started playing with her tits while she fingered herself. I wanted SO bad to just look over & see her bare breasts, but I couldnt because we had a deal. Then, about 2 mins later, I hear her say "Don, I just peaked at your cock! I guess you can look at me now." So, I glanced over, & there I saw her in all her topless glory, her tits are small, but they are SOOO cute! And she was rubbing her nipples & sweating just as much as I was. She told me to try rubbing my nipples because it felt so good. I took my shirt off & tried it, & my God, she was right! lol

Pretty soon, she started to moan even louder & shake. Suddenly, her whole body arched up & she screamed & started to cum VERY hard. Seeing her do that made ME cum. I shot a huge load out, & because of the angle I was at, it shot onto her bare chest, right in the middle of her orgasm. It was amazing.

We've done this a few more times since. We did it a few more times that summer, basicly the same way, did it once in early fall 2005, & did it ALOT in Spring/Summer 2007. But I'll have to write those later lol.

Hope you like!

 

Great Story, thanks for sharing!

 

Nice story, cant wait to read more.

 

Nice

 

That sounds like a lot of fun. I'm jealous. ;P

 

holy shit that was amazing you lucky bastard!!!

 

Boner achieved.

 

Lucky..!

 

your story made me just about cum just reading it wow i wish i was that lucky

 

I am so jealous. I would kill for that experience.

 

The first time I masturbated to climax with a woman was when we were unable to go all the way as she was having her period, but she didn't want me to have to go without.

Surprisingly, when I ejaculated it appeared that, despite having 4 kids (she had just left her husband) that was the first time she had ever seen a man climax.

It was also with this woman that whilst we were having sex my condom split, and I didn't have any spares, so I had to masturbate to finish off and, not wanting her to be unsatisfied, I also masturbated her to orgasm which, as it turned out was the first one she had ever had. Having had a strict Catholic upbringing in her childhood she had been brainwashed into believing that self masturbation was sinful, and apparently her husband had never given any consideration to her sexual enjoyment - once he climaxed inside her, that was it, so for her the female orgasm was a totally new experience - as was actually getting to see an ejaculation.

 

I am really wanting to do stuff now.

 

Great story pineman. I don't remember giving a woman her first ever O, but I have been told many times how nice it is to be with a guy who makes sure the woman comes. Seems to be a large number of guys who just dont focus on helping their girl reach orgasm, which in my opinion is the most fun part. Just hearing a woman say "I'm gonna come, I'm gonna come!" is probably the nicest thing you hear in the bedroom!

 

I got hard just reading this but when. The story started I was like oh hey it's girl telling the story then I heard the dick part and I was like oh shut this just got even hotter

 

I agree---great story. I didn't read your first one, and I probably won't, but I dig this one, and hope to hear more how your sexual exploits with your friend develop---did you ever have sex with her?

I remember in my early years of sexual exploration, that I masturbated with several girls---though it was more like them jerking me off while I fingered them to a mutual orgasm. I always had to help them get the rhythm right with my hand as I started to cum. The second girl I was with sexually, before we actually had sex, spent a number of nights with me doing this. And several times after we started having sex too, when we were worried about her getting pregnant, because I was still pretty young and didn't yet realize how easy it was to get condoms. (In fact we were pretty lucky I guess because we never used protection other than the rhythm method based solely on when her last period was---and even then our passions sometimes got the best of us.)

My wife and I have an open marriage. She sees herself as sexually conservative, but that is really a mask she wears from her Philippine catholic upbringing. When we met we were both in unhappy marriages, and spent months dating before we actually hooked up. Then she was my mistress and I her lover until we both got our divorces several years later. There was a lot of sexual energy and excitement in our affair, and there was an added excitement on the days when, as she put it, her husband had 'used' her. (For her it didn't work the same on days I had been with my wife, because she was very jealous back then.)

Several years after we had gotten married, we relived some of that excitement a few times through a one night stand here and there--a Japanese businessman who wanted very much to get into her panties, a doctor in the Philippines who would jog with her whenever he saw her jogging at the park---always in shorts and a t-shirt with no bra. When we came to the States we didn't do anything for a long time. It was harder to be discrete in front of the kids and so forth. But she's very hot and always gets a lot of attention. We had been here for about 7 years and she was working at a casino as a bartender/cocktail waitress. She caught the attention of one customer who spent a good 7 or 8 months trying to get her to go out with him. She was reluctant at first, but we agreed it was time to liven things up again. So she finally agreed to go out with him.

The first date he got her tipsy and they ended up in a park that is well known as a make out place. They made out for a while and she allowed him to play with her boobs, and he tried to get into her panties which at first she stopped him, but then finally allowed him to finger her, and then lick her to orgasm. She wouldn't allow him to do any more so he returned her home, still pretty tipsy and her lipstick smeared, and her bra was pulled down because she let him play once more with her boobs as they kissed goodnight. We then had a hot session of sex while she told me everything he did.

They went out a week later again, only this time he had a pickup truck with a topper over the bed of the truck. He had put a mattress in the back. That's not how you woo my wife, but, they ended up in the same park and in the back of his truck, where she once again allowed him to suck her nipples and lick her pussy, this time allowing him to take her dress completely off. But she wouldn't allow him to go any further.

It was probably a week and a half later when they went out again, and this time he undressed in the back of his truck with her. He is a tall guy, well over 6 feet, but she was surprised by the size of his dick, which is apparently 9" erect, and fat. She still wouldn't allow him to have sex, and now she was even less willing thinking that it was too big. He rubbed his dick while eating her pussy, and after she had an orgasm. She watched while he masturbated his massive cock. She described to me how it jerked when he came, and how the first several spurts of his warm cum landed on her belly, which she pointed out was still dried on her as we had sex that night. Watching how he came and having his load land on her did make her hot, but she was reluctant to take on that much size.

On their next date, they made out naked, bodies pressed against each other, his massive dick pressing against her stomach and then he got down and ate her pussy. I think he was expecting that she would allow him to have sex, because rather than bringing her to orgasm, he slid up alongside her body and started kissing her on the mouth again. She said that she would not yet let him do it, but that she would jerk him off. Again she was amazed at the size when she wrapped her hand around him. She started moving her hand up and down and after a bit he helped her. She said his dick seemed to get harder and then started jerking in her hand as he came all over her belly and chest and on her hand.

This was repeated on the next date, only he put his body over her, supported on his legs and arms while she jerked him off, his cum landing all across the length of her torso. Afterwards he watched her masturbate and then licked her pussy to an orgasm. This went on for months, she would never let him actually do it. Sometimes they masturbated each other, or watched each other as they masturbated together. One time he sat between her legs, while she jerked him off, and the first several spurts of cum went across her belly, but the last ones came down on her pussy. He had already licked her to an orgasm, but she told him that it was wet and warm on her pussy and felt good. He laid down next to her, and she allowed him to rub the cum on her pussy, and then he stuck his fingers, wet with his cum, into her pussy and fingered her to another orgasm. She doesn't really like the taste of cum, but on subsequent dates she licked his cock and several times gave him a blowjob.

He was getting more and more anxious to have sex, and was telling her that he would be gentle and that if it started to hurt he would stop, and they would use lubricant and so on and so forth. She still wouldn't let him do it, and besides, I would bring her to multiple orgasms during sex after their dates. But she would allow him to cum onto her pussy in most of the dates that followed. Then one time he was over her, on his arms and legs, and while she rubbed his cock, he begged to let her just touch it against her pussy lips. He insisted that he would not push it in, but that he wanted so much to feel it against his dick. She finally agreed so he rubbed his big cock across her lips and in between her lips. She felt his fat head against her hole and it felt so good to her. He started rubbing his cock with his hand and immediately came all over her pussy and her groin. It was such a turn on for her. They went out on a date the following night and they did it again, only this time she let him rub his cock on her again after he came, which he did smearing his semen all over pussy. It was so hot for her that she started moving on it. She knew it would be too easy for her to do it, so she stopped him and made him finger her to completion.

She was starting to become too frustrated, and we knew he was definitely very frustrated, so we decided that she would have him take her to a hotel about a week later on the following Saturday, and she would finally, after months of this, let him do it. We were both excited about it, as was he (only he didn't know that I knew all about it). However, what I didn't know at the time is that on the Thursday before that weekend, he showed up at the house while I was at work, and asked if she would would go fishing with him. She agreed and had the older kids watch our son until she got back. They fished for an hour or so and then ended up in the back of his truck. She did make a comment about it being only a few days before he could have her completely. Once again she allowed him to rub his cock on her pussy lips, only after a few moments, she grabbed his cock and started rubbing it across her pussy, masturbating herself with it. After rubbing her lips and her clit, she started rubbing her hole, and naturally she was moving against it with her groin as well. She then went back to the lips and her clit, and back onto the hole. She was in heaven and her hole was opening up, as if to accommodate this large hard cock. She moved it side to side against her hole, and in the center. Her body seemed to naturally slide down, and the head of his cock was now more or less inside of her. It felt so good, and she was moaning loudly. She continued to move it side to side, and it seemed to make her wider. At this point he gently pushed and it went in a little bit more, which felt incredible to her, so she let go of his cock and put her arms around his back. He gently pushed it in a little deeper and pulled it out, before another gentle push in. She was so turned on, there was no way of stopping him. Gradually with each push he was deeper into her. Once he had it all the way in, and he rested for a moment, she said to him, "Hey! I didn't say you could do that." They both laughed, until he moved his cock in her and she responded with an ecstatic "oh!" It didn't take too long for him to start cumming. She has a very sensitive vagina, in this regard and loves the feeling of someone cumming inside of her. (If I didn't cum enough in her opinion she would always accuse me of being with someone else, so like I said her vagina is very sensitive to such things.) As soon as she felt his hard cock contracting inside of her, she too started cumming.

Since this was not how we planned it, she didn't tell me about it until sometime later. I was still under the impression that the following Saturday night at the hotel was their first time together. That night proceeded about the same way, with her rubbing his cock all over her pussy while her hole opened up. It was a little more painful though because he was not as gentle at first. They had to stop and rub ky jelly on him. But it was a little less hurried then the last time, and this time they took more time to enjoy each other’s bodies Afterwards she fell asleep in his arms for about 45 minutes before he brought her home, about 2:00 am. As she related what I thought was their first time, I found her to be very loose, and of course very slippery and wet. We had sex twice that night, and several times the following morning. She always says that the first couple of times he ever came inside of her were so intense---he completely filled her and the contractions seemed to run up inside of her pussy.

 

^^^ very hot

 

The first time I jerked off in front of a girl, we were on a date, with my steady girlfriend and we had been having sex regularly. We were necking and petting each other in the car that night and for whatever reason ( her time of the month, mood or whatever ) she did not want to have sex. I had a raging erection and was at the point I needed release. I pulled my cock out and jacked myself off sitting in the driver's seat with her sitting beside me watching until I exploded. Though I had an orgasm, I was pissed that she put me in that position. That was the first time I masturbated in front of a female.

 

I don't find this tale credible. It's impossible for me to believe that two opposite-sex friends who are obviously attracted to each other would so easily be content with simple masturbation and never once be tempted to have sex.