Where it happened: Home, my bedroom
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My sister’s best friend would spend the night every two or three weeks on a pretty regular basis and I was ok friends with her. After my sister would go to sleep, her friend and I would stay up and watch TV, talk, play SNES or whatever but on one fateful night, I clicked past “Cinemax Afterdark” which of course was softcore porn. Needless to say I was completely enthralled at the naked woman on the screen and my sister’s friend didn’t complain either. After the soft sex scene we started talking about what little we knew about sex (I was 13, almost 14 at the time, she had just turned or was almost 13) and tried kissing and making out. We didn’t go much further that time but that didn’t stop me from looking at her in a different light. She was pretty but she wasn’t some perfect 10 (she was 12 or 13…). She had only recently graduated out of a training bra but didn’t have much there but she had really long legs, a pretty face and long curly brown hair that went past her shoulders.
Each time she’d come over to spend the night we would wait for my sister to go to sleep and we’d either try to find something dirty to watch or we’d just talk about sex and then make out. I felt her boobs as often as she’d let me but most of the time we would make out and after she’d go to bed, I’d go beat off…twice. 🙂 Fast forward to right after my 14th birthday and her and I had been at this a 1/2 dozen or so times. I had acquired some porno mags and she snuck into my room after my sister was asleep. Most of the mags were of women posing but I had two hardcore mags that showed penetration. As we looked through them I told her how hard I was (it was obvious, I was stretching my tidy whities) and she asked to see it. I told her only if I could see her too. She was quicker than me; lifted up her nightshirt, pulled down her panties and there is was in front of me, my first live pussy. Puffy lips, a little bit of moisture on the slit and a tuft of light brown hair on top and starting to creep down her lips. My underwear came off as well and I kinda wagged my boy boner around. We spent some time touching and exploring each other, talked about masturbating, I even jerked off once for her (god to be 14 again and recover in no time).
We touched and played for well over an hour before we started to make out again with her lying flat on top of me. She would press her pussy against my hardon and we would grind against each other and we did that until we both had an orgasm. Needless to say, she was a bit sore from the friction but it was very satisfying. The next time she came over to spend the weekend, we went all the way. I showed her some pics of people having oral sex and we both spend the first night sucking and licking, fingering and jacking (we both even fingered each other’s anus to see how that felt). The second night she stayed over she was laying on top of me again but this time I asked her if we could “do it” and she said yes. I remember her asking me to slow down when I pushed inside of her and broke her cherry and I also remember lasting a whole 20-30 seconds before draining my nuts inside of her.
Thankfully I recovered from my short performance and we had many great times until her family moved when she was 16. That girl and I learned a lot about sex together and for almost 3 years had a very fulfilling sexual relationship (we never actually dated nor considered ourselves “together”) that I’ll always look back on fondly.
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