Kelly's Diary 103 - First Time With My Junior Roomie - Cover

Kelly's Diary 103 - First Time With My Junior Roomie

Copyright© 2025 by Kelly85

Chapter 2: Jen Misses Her Boyfriend

Erotica Sex Story: Chapter 2: Jen Misses Her Boyfriend - Jen was my Junior year roomie and cute as a button. She had a boyfriend with whom she is definitely no prude but had never been with a girl. From the day we met I dreamed we could be closer but never actually dared to hope that our relationship would get as close as it did!

Caution: This Erotica Sex Story contains strong sexual content, including Fa/Fa   Consensual   Lesbian   True Story   Masturbation   Oral Sex  

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!

 
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