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Kiss and Tell, Stories Of Growing Up

Posted by: Age: 30s Posted on: 0 comments
2 likes 4907 views Category: Masturbation Male-Female Tags: masterbation, mutual, girlfriend, finger, stroke

This is a collection of quick stories about my girlfriends and I sexual explorations while we made out in my school years.


My first girlfriend in high school and I used to make out every chance we could get. That was often since her parents worked the overnight shift and spent most of the afternoon asleep in their second floor quiet oasis of a bedroom. They were on the night shift for many years and with the kids coming home from school the parents built themselves into a quiet zone on the second floor. From what my girlfriend told me they very rarely heard any noise or saw any day light for years. With us in her bedroom, after school, the only way her parents would know I was over so much was if her brothers told on her. She said they would never because she had dirt on them and she would spill the beans on them in return. Plus her brothers were cool. One brother once asked me if I needed any extra condoms. Anyway, we would kiss for hours and almost never actually say anything to each other.

About a week into our make out sessions she started to rock up and down on me, or under me while we kissed. I never once had a clue what she was doing since I never thought girls played with themselves. Once I did figure it out and realized she was using my erection, under my clothes, to rub herself to a fine orgasm, I figured I would get in on the action. Only once did I get close to busting a load in my pants. She was on top and riding me like no tomorrow. I found if I held her knees out to the sides I could get more of her rubbing on my erection. I think it helped I was wearing a swimsuit that day as she had said she wanted to go down to the beach that afternoon. We ended up staying in and making out. She must have climaxed and wanted to stop just as I was about to lose it. That sucked! We ended up splitting shortly after that. But I always now think about how used I was, without first knowing it, so she could get herself off.

My second girlfriend would let me finger her once in awhile. She was a bit slower than most in the natural progression of first base to second base. We would sit on the couch or occasionally in her room or mine and make out by mostly kiss and I would finger her from time to time. I was granted permission from my parents to paint the walls of my bedroom. My girlfriend was allowed to help, as well as her friend. Just as we were about done with the room her friend calls home to find out she is needed at home asap and no one from her family can come get her. My mom had to take her home. That left me alone with my girlfriend. We were to clean up and wash the paint brushes out before they dried up. My father was expected home from work any minute.

While walking out of the bathroom with my clean paint brush my girlfriend comes into the bathroom and almost walks into me. She jokingly points the paint brush at my crotch saying she will paint me if I don't move. I felt extra bold that day and dropped my shorts in front of her, causing an instant erection. She took one look and said I should not have done it because now she is going to have to paint my dick. I thought she was just kidding and would not do it. She slapped that paint brush left to right across my dick painting my dick green. She stood back and admired her work. She then stepped forward again and said she missed a spot and painted the tip of my dick. I was a bit in shock she actually did it. I told her she now has to help me clean it up. She said she was all for it and would wash me with no problem.

She got a wash cloth and soap and she washed the green paint off me. Of course it felt oh so good and I let her stroke me up and down. She of course was just removing the paint, until she realized I was enjoying it a little too much. She got most of it off and told me to finish the rest of it. I begged her to continue, even if she did not get the paint off me. She stayed for about two minutes stroking me and also twisting around the shaft. I did not cum at that time but told her she could stop. I grabbed a towel and dried myself and raised my shorts. We kissed and went to walk out of the bathroom when my mom walks down the hallway looking for us. Had she come home twenty seconds earlier she would have seen me half naked in front of my girlfriend.

About a month later I lost my virginity to that girlfriend. We would always use condoms or no sex and we would only have sex about once or twice a month. She moved about three months later and we lost touch with each other due to the distance. I stayed single for about a year, beating off almost every day. That is until I met my third girlfriend in high school. She and I would kiss and she would let me rub her boobs from time to time. About a month into our dating I ended up bringing her around the corner of this building where we were hanging out with friends, to talk. We ended up kissing and I fingered her for the first time. She was so wet and her pussy lips were extremely puffy. She ended up agreeing with everything I said or offered. It was like she was wrapped around my finger, figuratively and actually. I finger banged her so much that night, for about two hours straight. I really wanted to go down on her but she would not let me due to us being outside and our friends were right around the corner. She did not want anyone to catch her half naked. Every time I tried to take a break and rest my wrists she would guide me back to her pussy. She must have been in heaven.

Later that night I drove her home and we stopped in a parking lot and jumped into the back seat. When I took her panties off I could tell they were soaked! We had sex in my back seat that night. She said she did not like being cramped in there like that so in the future we would find a place we could lay next to the car, outside, but secluded from anyone. We would do it in the woods or playgrounds almost every other night. She never beat me off or did oral sex on me. She finally admitted to me she did not want me to go down on her because she was afraid I would smell her sex. I told her that was the best part and I craved her scent and really wanted to do it.

She found out how good I was and would ask me to eat her out from that point on. She also told me she thought her mom would sniff her panties and could tell which days we had sex. I told her we could stop having sex and she told me I was crazy, at that point she did not care who sniffed her panties. I once fingered her while we sat on the couch watching cartoons. Her dad and step mom were in the dining room and could see us, if they turned in our direction. We used no covers of any kind. It was pretty much out there in the open and we could have been caught by anyone in a split second. We ended up going to different schools and losing touch.

My first college girlfriend would not let me finger her. Play with her boobs and kiss was all she ever wanted to do. I finally went and bought a large pack of condoms and told her we would spend the snowy weekend in bed having sex until all the condoms were gone. From that point on we would have sex just about every day, so long as I wore a condom. She once had a sex conversation with her roommate in the room. I thought we would end up having a threesome. But her roommate ended up leaving us alone. I later found out she had been missing her boyfriend and was very sex craved. The roommate ended up getting caught by the RA in the female showers rubbing one out to completion. My girlfriend told me the details on how her roommate did not know she was being watched and by the time she found out it was too late, she rubbed herself to an orgasm in front of the RA.

I have also had female friends that would tell me about finding out how great it felt to let the tub water hit them in that special spot, or use the handle in the tub to insert it in their pussy and pretend it was a ever erect penis made special for them. I even had gone over to a female friends house mere minutes after her boyfriend left after them having sex. She tells me to wait in the kitchen she had to go finish herself off one more time while the feeling was there. I sat there like an ass awaiting her return. She comes into the kitchen, smiling ear to ear saying how great sex is but how much more satisfying the after sex masturbation is.



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