There was a girl, Alison, who hung out in my circle of friends. She was five years younger than me and would come over on the weekends or after school. I had noticed her about a year before at this party or that and it just ended up that we knew a lot of the same people. There was another girl, Lacey, who went to the same school as Alison but Lacey lived at her mom's house just a few blocks away from my place, which I shared with two girls I went to college with. They had the two downstairs bedrooms and paid the rent. I was "the cabana boy" and didn't pay rent, but I also didn't have a room and slept on my futon upstairs. It was actually a pretty cool set up because the upstairs was this awesome open area with a vaulted cathedral type ceiling and one wall was all windows and a sliding glass door that led out onto a small wooden balcony. It had an alpine chalet feel to it.

We had a lot of good times in that duplex. (There was a matching unit on the other side of us). One of those times for me was with Lacey. We had gotten some mushrooms and stayed up all night having a heady adventure. I don't even know if we left the house at all but somehow or other Lacey ended up with me upstairs after everyone else had gone to bed. Now that I think about it, she probably planned it that way. Now that I think about it, it's even possible she lost her virginity to me that night, I don't know.

High school girls are a lot of fun in that they can be so shy and nervous it is just so precious and fragile, but also it can be a little frustrating because they are so scared to be honest about things so half the time you don't know if they are telling you the truth or not. 

 We started making out, just laying there in the living room/(a.k.a. my "bedroom"), cuddled up in a heavy sleeping bag and a quilt. We both wanted to have sex with each other but there was a fear that something might change between us as we enjoyed a good friendship, so we had a short conversation about it and agreed we were not going to be boyfriend and girlfriend but that we could enjoy each other that night. 

 I took her clothes off and mine. I ran my hands over her perfectly smooth skin. She was more of the tomboy body type, not terribly curvy with small breasts, but her ass was just so perfect, tiny and firm. She had a trimmed but not shaven bush. We kissed some more and rubbed the smoothness of our bodies together. I guided my hard cock to glide up her thigh, across her outer labia and down her other thigh, then kept rubbing and gliding over her smooth skin.

After a little bit more of this, I started to rub the head of my cock in between her labia, where the lubrication was seeping out of her pussy. Once the head of my cock was covered in her juices, I set it just inside her inner labia and moved my hands up to hold her head and run my fingers through her hair. I kissed her as I slowly pushed my cock inside of her incredibly tight and wet pussy an inch or so, moving the lubrication further onto my cock.

 I have always loved this moment, when my cock is dry and my partner's pussy is wet. When I push and of course I could force it in dry but I prefer to go slowly, wetting the first inch, pulling back out, sliding in again, maybe another half inch deeper this time, getting that much more of my cock wet. Then pulling out and going back in, a little further still but not all the way in yet. This is just the best, especially in a tight teenage pussy, the flesh so firm and her eyes so full of emotion.

 I looked at Lacey and kissed her again, then held the eye contact with her as I entered her fully for the first time. We stayed close like that in the missionary position the whole time. I don't remember how long it was but I don't think we changed positions, just stayed under the covers quietly and slowly making love.

There was a certain amount of intentional stealth to our actions, I don't think Lacey wanted my roomates to know she was having sex with me. There is a thing among girls or at least there used to be, the judgement of "sluttiness", which I am hoping is starting to pass with the feminist movement and the empowering of women as we move forward ethically towards equality and also away from fundamentalist ideas about sex being bad/evil/taboo. I also liked to keep things a bit private since I enjoyed sleeping with various girls but didn't need to broadcast my sex life to everyone. 

 That same week, I forget if it was a day later or two days later, I had a similar experience with Alison. I have to admit, I was more attracted to Alison and now that I think about it, I think she probably knew about Lacey and me and made her move on me thinking that she needed to act fast if she wanted to get with me. However it went down, shortly after I had my escapade with Lacey, Alison figured out a way to spend the night (she lived a few miles away so had to give her parents a story why she was staying the night in town) and we found ourselves alone at the end of the night.

Alison was a little more curvy than Lacey. She had small breasts the same, but her hips and butt were more curvy and I adored her cute little face. She had freckles, brown eyes that sometimes had different colors in them like green, yellow or hazel. She had such an incredible playful spirit, always hugging everyone and making or getting little gifts for people. Just a peach of a girl, through and through. Her hair was short (not as short as Lacey's, who had a bob-cut sort of thing) and straight and she often put it back with barrettes. That night she had on a thin t-shirt and some baggy cargo shorts.

 We had the make out session and then it came time for the talk. I told her I had liked her for a long time and that I wanted to be her lover/boyfriend so that I wasn't just interested in a one night stand. She didn't really say a lot in return, just that it would be okay with her. She seemed a mixture of scared and happy, I could tell she just really wanted to please me. At the time, I wasn't as good at communicating or developing a girl who had such potential but I see now she had a lot of submissive tendencies and would have probably loved being a slave/sub if I had been more experienced. As it was, she just wanted to do whatever I wanted.

 So I took off her clothes and made love to her. I had such incredible orgasms with that girl, her hair was so soft and perfect for getting a handful of. She made the sweetest little moaning sounds as I would grind on her clitoris, sort of a mix between a moan and a whine as my cock penetrated her. Her pussy was so tight if I just relaxed and stopped pushing, it would start to squeeze out of her. It would never stay long after I came inside of her, because as soon as it started getting limp it would get forced out.

Those days with her were definitely some of the best, though she reminds me a lot of Brianna, who I didn't meet until years and years later when I was in my 30s. Actually, I will make another post about Brianna later but one last thing about Alison.

It was one night I had been up but she had gone to bed early, maybe an hour before me. I came to bed and started to cuddle with her, which turned me on and soon I had a hard on. I got on top of her and my cock was betwen her legs, the wetness from her pussy was incredible. I couldn't resist, so I put my cock in her and to my surprise she was soaking wet, way more than usual and way more than would be normal since we had only been cuddling, not really having much foreplay. I said something about how wet she was and she said, "I wanted to be ready for you". I don't know how she did it or when but she must have heard me coming to bed and taken a bottle of AstroGlide that we kept next to the bed and she put a squirt inside her pussy so it would be totally lubed up for me to slide right in.

That's the kind of lover that just turns me on so much. Who wants nothing more than to please me, so much that she thinks of something like that on her own and totally surprised me with. Now I am more experienced at sub/dom relationships so I can take charge if I want to and say, "Go to bed and play with yourself. You can put Astroglide in your pussy or masturbate to get yourself wet for me, but you need to prepare yourself. I will come to bed in a half hour and I want you turned on and ready for me to fuck."

 But it is still nice for a girl to take the initiative now and again. Just because I like to dom doesn't mean I want to always have to do all the thinking as well. An intelligent and proactive sub is a wonderful partner to have.