First Experience. (sorry if anything is spelled wrong, i was never great at spelling).
This all started out at my house around seven in the afternoon. I had invited my girlfriend of four months over to eat, hangout and maybe watch some tv. Well it's summer time so it doesnt really get dark until 9 to 9:30 which was unfortunate for us because the only room we were allowed to be alone in was very well lit by many windows. It was getting close to 11 which was when my girlfriend (we'll call her Katie) was supposed to be home. By now it was obviously dark and my mother had gone to sleep and my father was staying with my grandmother that weekend. It had been four months and nothing really great had happened between us, and it was really getting to me. Well we were laying down on a huge body pillow, I suppose we were in a spooning position. We had 30 min before she was to leave. (By the way she is my neighbor) I decided to take a chance, which isn't really a big deal now, but when I was 16 this kind of stuff is what it was all about. I started to tickle her and 'accidentally' brushed against her breast. After a few of these we settled down, but I kept my hand on her breast. Eventually I slowly moved my hand around trying to massage her. I was so nervous I was hardly touching her, and to this day I doubt she could even feel my hand through her bra. But soon enough I built up enough courage to just go for it. I began to massage her back and slowly up her side until I reached her bra strap. I moved my hand to the center of her back where the clip is and amazingly, even though it was my first time undoing a bra strap, I got it loose without and trouble. During this time I had been staring deep into her eyes, watching every movement, making sure she was confortable with this. Of course I worked my way around and made contact with her breast. I remember thinking it wasn't anything like I had imagined it feeling like. We laid there for 30 min while I massaged her all over. After awhile the time came for her to leave.
The only one home at her house this whole weekend was her older sister who was back from college. As I was walking her home her sister calls and says that she is leaving that night to drive to the next state over to see a wedding of her friend from college. As soon as Katie got off the phone she looked at me and asked if I would like to stay for awhile and watch a movie. There was no way I was going to turn this down, so I ran home turned out the lights and closed my door so my mother would think I was in bed asleep. I crept out and back to Katies. So fastforwarding a bit, we had eaten, and played some cards, now we're watching the movie. so about half way through the movie I decided to get back to where I was. So I went through the same procedure and eventually was feeling her up again. Because we were lying down on the couch and there wasn't much room it was hard to get to her. After earlier that evening I had an unusual amount of courage built up, so I asked if she would remove her top and bra. Without hesitation she did, which was very surprising to me. To be fair I too removed my shirt. For the longest time we layed there making out and really feeling each other's bodies. During all this the tv suddenly went staticky from overhead clouds. So no more movie. We decided I would stay until early in the morning so I could get back to my house before I was found missing. Once the movie was no more we moved to her bedroom to lie there.
For the longest time neither of us moved. We just lied there and stared at each other. Eventually my mind started wandering and thinking about everything sexual I wanted to do with this girl. Now Katie is one of the most beautiful girls i've come to know. She isn't the type that wears all the makeup, but still she has something about her that makes her very, very attractive. So as you can imagine my mind was wandering Very far. With this confidence still built up I steadily moved my hand to where her shorts were on her hips. We had talked about sex and she wanted to save that for marriage, as did most of the girls I dated in highschool. Knowing this I asked her if she wanted to 'try' different things besides sex. At first she wasn't sure and didn't give me a definate answer. After waiting a few min I started the tickeling again. Knowing that she is ticklish on her butt I quickly moved my hand under her shorts and underwear and sqeezed. At first I think she was unsure what to do, but slowly I started to again massage her, this time on her butt. She didn't seem to mind, but quietly I whispered to her 'tell me if I go to far'. While still massaging her butt I carefully worked my way further and further between her legs. Suddenly she jerked and said 'that's good' which I took to mean that's far enough. So now I figured I had a stopping point to which I couldn't go past. I continued at it for another five min until Katie mumbled something. I asked her again and again what she said, until finally she said these exact words 'You can if you want to'. Hearing this I was a bit confused and didn't realize what she was talking about. Then it came to me, I reached down her shorts a few inches, stopped, and looked at her. She nooded approval. My heart almost stopped. Once the thought actually hit me my heart started to race rapidly like never before. I could almost hear it. As with her top and bra, I asked her to remove her shorts and thong. And again she supprised me by doing so. All this time under the covers and in the dark. So I can't really see anything at all. At this time I had never seen a pussy (except in pornography), and definitely never felt one. So basically I had no clue what I was doing. Well I move my hand down there and feel around. It was amazing, and all I was doing was feeling with my hand. It was so wet and warm. For a few min I just moved my fingers around and watched her reactions. Some time had passed so I decided to go further. I pushed my finger to what I thought was her vagina (i couldn't tell because I had never done this before, and I was doing this in the dark, under the covers). It too was amazing. About 5 min had passed and she started to jerk around. I had no clue what was going on, so I continued. Soon she was lifting her thighs in the air and suddenly, her legs buckled and she fell quiet. She then grabbed my hand that had been working her and held it close to her breast and just layed there quietly until she fell asleep. I too just layed there. It's all I could do. I wanted to start on myself, but I just couldn't. All I could do was just sit there and reflect on everything that had happened. It almost didn't feel real. Her alarm went off, telling me it was time to go back to my house. I got my shirt and kissed her goodbye and walked home. Still in awe of what had happened.
More between us happened, and I have plenty more stories to tell about my college years. I hope you enjoyed my story.