Chapter 2: Jen Misses Her Boyfriend

As the weeks went by I could tell Jen was missing Alex more and more as it seemed she was getting hornier with each passing day. This worked in my favor as gradually we opened up to each other more and more in terms of discussing sex. I love to sleep nude and I can still vividly remember the shock on Karen’s face the first (and last as it turned out) time she saw me slip under the sheets with nothing on. In contrast to my previous roomie, Jen’s eyes may have widened a little bit the first night but she didn’t say anything and in fact the next night I noticed that she was sleeping nude as well. I smiled at her as she dropped her robe, revealing her uber-cute petite nude body before quickly covering herself under her blanket. Her face reddened as she held the covers up to her chin and told me that sleeping naked was something she’d always wanted to do but her parents would’ve had a fit! After that night we didn’t say anything more about it but it was the last time either of us wore anything to bed.

I loved to chat with people on-line about sex at night and while I could never get Jen into it (none of my friends do either unfortunately) at least she didn’t interfere with me. Although she knew I was chatting a lot she never really knew about what and certainly never knew that at times I was discussing my incestual relationships!

Sometimes she would get on the phone with her boyfriend as I was chatting and it was at those times when I could tell she was missing him a LOT, and in more ways than one judging by the way she squirmed when they talked. Sometimes she would get up and take her phone to the bathroom. I would just sigh, wishing she wouldn’t feel she had to hide when she played with herself while she talked to Alex. I would’ve loved to have heard what she was saying to him as well!

The real breakthrough came after about a month or so of us being together. Although I tend to be a night owl, mornings have always been my peak sexual time. I seem to always wake up horny as hell, my pussy wet from whatever nasty dreams I must’ve been having. At home my dad stops by my room before he goes to work which helps me out but usually he doesn’t have a lot of time and I still will often masturbate even after he has fucked me. At school now I’m left to take care of myself - literally. At first I just fingered myself quietly under the covers, trying not to wake Jen. Apparently I wasn’t totally successful because one morning when I thought she was sound asleep I must’ve been a little louder than I should’ve been when I came. Jen was on her side turned away from me but to my complete surprise I could tell from the way she was moving that she was doing herself!

When she had finished she turned over and we both looked at each other and then broke out into laughter. Apparently we were both horny in the morning and each of us had been trying not to let the other know. Well, from then on we didn’t try to hide it when we played with ourselves and as we grew more comfortable with each other we got more open about it. It wasn’t like we were putting on a show for the each other but at the same time we didn’t hide it either. For me it was almost like being home where masturbation was nothing to be ashamed of and I felt free to do whatever I wanted at any time. For Jen though it was an entirely new experience. Her mother had always told her masturbation was something only the “bad girls” did and so she had always been shamed when she did it but at the same time couldn’t stop herself no matter how hard she had tried. She had never masturbated, or even touched herself for that matter, in front of anyone, not even Alex and certainly never another girl. I asked Jen if she hadn’t done it together with any of her friends during a sleepover or anything like I had when I was in high school. Jen looked shocked when I asked as if she couldn’t believe a bunch of girls would ever even consider doing anything like that. Well, I guess they raised them pretty conservative in mid-Wisconsin!

Although Jen had never been with a girl and so far had really showed no interest in it, I have to admit that during many of our masturbation sessions while she was dreaming of Alex I was imagining being closer to her. Once we started playing in front of each other in the morning she started being more open about her feelings when she had phone sex with Alex, something that seemed to get more frequent and naughty as time went by and she got hornier for him. While she was fingering herself telling Alex how much she wanted him in her pussy I would be sitting in bed alone with my laptop, chatting with people on Yahoo! and fingering myself. I am sure she thought I did it because of the conversations I was having with my on-line friends but in reality I was imagining what it would be like to help her get herself off as she masturbated while she talked to Alex.