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


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#1 RENTfan87

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Posted November 16 2008 - 12:39 AM

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!

#2 Panther28

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Posted November 16 2008 - 07:43 AM

Great Story, thanks for sharing!

#3 KyleDaKid

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Posted November 16 2008 - 05:20 PM

Nice story, cant wait to read more.

#4 sophieclair

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Posted November 16 2008 - 05:42 PM

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!


Nice

Who are they to judge me? I know I am not perfect and I don't claim to be. But before you start pointing fingers, make sure your own hands are clean.
-Anonymous


#5 KatelynPaige

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Posted November 18 2008 - 02:40 PM

That sounds like a lot of fun. I'm jealous. ;P
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#6 flea66

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Posted November 26 2008 - 10:39 PM

holy shit that was amazing you lucky bastard!!!

#7 Severely stoned

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Posted November 26 2008 - 10:46 PM

Boner achieved.

#8 brianlara

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Posted January 08 2009 - 11:52 AM

Lucky..!

#9 sir jerks alot

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Posted January 10 2009 - 03:58 PM

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

#10 Jack8274

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Posted January 10 2009 - 04:08 PM

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

#11 PineMan

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Posted January 10 2009 - 06:17 PM

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.

#12 menagemoi

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Posted February 08 2009 - 05:07 PM

I am really wanting to do stuff now.

#13 PigWig

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Posted June 06 2011 - 04:21 AM

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!