3245 Views |  Like

My Insane First Time

Age when it happend: 17
Where it happened: My Bedroom, circa 3 AM.
Langauge: Portuguese, Brazil
Sex: Male
Rating: 1
Category: Straight

I had a virginal girlfriend at 17 and we did not lose our v-cards together. She wasn’t exactly holding out for marriage either, but nothing I could do or say could convince her to give up the cherry. I’d seen her naked many times, and I felt like a dog staring through a butcher’s window when I saw her pussy all shaven and puckered between those tightly bolted thighs. My final frustration came after we took a 2 day, 2 night trip to Disneyworld and I got to ride everything but her. This was my blue-ball limit after dating for two years and I decided to say “the fuck with it” and cheat on her. How quickly and easily it happened still amazes me till this day.

I had just joined a friending community on a cell phone application called BLAH. This was 2002 when apps were still pretty primitive. All it displayed was age, sex, city, and interests. Feeling overhorned and desperate my only listed interest was sex. Hell, this was anonymous, why not? I got several texts in the first day from different people, but mostly from dudes-not what I set out for. A few days later, I got one that was so sexy, I must have paced a half mile while I tried to think of a worthy response to send back. That same day we texted for about 3 hours, eventually switching numbers. I called her and immediately it was like our texts were starting to come to life. I didn’t care if she was a fat 44 year old Bette Midler stand-in, in my mind she was hotter than the Carmen Electra Baywatch poster on my wall. She started moaning and told me she was touching herself and that she wanted to hear me masturbating. I remember saying some dirty shit for a 17 year old virgin but I came pretty hard as she was telling me how tasty I was. After I cleared my other head I told her that we should meet up tonight. Immediately she said yes – I hung up and giggled like a 13 yr old schoolgirl.

Somehow I was going to sneak out and we were going to meet at midnight at the bus stop near my house. Like clockwork, the ‘rents went to bed at 10 and my sister at 11. All the lights were out when I made my move and was out like Richard Simmons. I stopped at the pharmacy and bought a pack of condoms then proceeded to the meeting point, mentally shitting myself about what she would look like. From her descriptions on the phone she sounded hot but as the saying goes, “beauty is in the eye of the beholder”. Here I was prepared to lose my virginity to a stranger, and I remember thinking that “virginity” really is overrated! (though I was probably just bitter from my Blue Ball stretch). As I approached the bus stop I could see a tall dark figure. To my excitement she looked in shape!! As I closed in like a cheetah, what stood before me was a dark woman oozing with sex appeal. Being that I’m a white guy, I just smiled in amazement. I had never even hit on a black woman, and now I was about to score some chocolate coitus! She was my height, over 6 feet, had very large breasts, and wore a skimpy two piece getup that made her look like a contestant on “So You Think You Can Dance”. I couldn’t believe I hit the motherload with a goddamn cell phone. (Thank you, Nokia) We talked for a bit, and then she made her move and kissed me right there in the street.

I offered to go back to her place and she said “No, my parents are home, Lets go to yours.” I still don’t know what was going through my head at that moment, but I didn’t even hesitate. Before I knew it we were on my bed stripping down. She took me all in her mouth and I told her I wanted to put a condom on. I stuck it in, and we did the glorious deed for a good 20 minutes when she told me to come in her mouth! It was the best orgasm I’ve ever had till this day…. Just so naughty to know my family was asleep and my girlfriend was out there somewhere thinking she had me on a leash. I was very pleased with myself for lasting that long, but I realize now it’s probably cause I jerked it earlier on the phone. We did it a second time doggy style and it was a dream come true after watching that position so many times on my VHS collection. Afterwards, was the craziest part. She told me she was actually 25.

She asked to take a shower (my bedroom had a bathroom). Reluctantly I agreed, and when she came out glistening in waterdrops, she asked if I could give her something to remember me by. I knew it seemed to good to be true. I thought she fucking wanted money and that I had been played by a hooker…but then she went to my closet… and took out a t-shirt that smelled like me. I started thinking paranoid thoughts about how she was going to start stalking me and my family would find out, or worse my g-friend! I said no, but she kept scrummaging wanting my cologne and one of my caps. I told her she could take my toothbrush if she wanted and then she turned on her bitch switch! She started talking loudly and saying how none of this meant anything special to me and that I am selfish. Worried the rents would awake, I told her she had to leave and she actually took my effin toothbrush with her. (lol) We snuck out the window and I walked her to the bus stop anyway. I told her we couldn’t see each other again and she told me that’s fine, she wasn’t planning on it either. Then she kissed me really passionately and told me I fucked her really well. It was all too much to process…is she was sane or not? was she just a sympathetic prostitute? or was she just a sex addict? All I know is I really enjoyed my first time. It is still the most adventurous thing I’ve ever done in the name of sex. The best part of my memory is her name: Neurylane.
My first time was with a girl named Neurylane and yah, it was a little insane. No one ever had a clue and I’ve only told this to one person that knows me, and now you, viral and anonymous crew.

Processing your request, Please wait....
  • 0 - very bad experience 10 - very great experience