Chapter 4: Crossing the Line With Jen

So it went until it was the week of Thanksgiving break. It was a short week and everyone was waiting impatiently to go home Wednesday afternoon. Jen had tickets to fly home and from her most recent phone calls with Alex, I had a feeling Alex had better be ready for some serious sex when she got there! She was as horny as I had ever seen a girl be and was masturbating two and three times a day - at least so far as I knew. I figured if there was ever going to be a time to try to make that next step with her, this was it!

Monday morning arrived and we were both up early going at it in our respective beds. The covers were thrown back and we both were on our backs with our knees bent and spread apart to let the other see as best as possible. Neither of us had an early class on Mondays so usually on this day we would get off and then hit the bed for another hour or so of sleep to let ourselves wind down. I climaxed first as I dreamed of what I was about to do with Jen if only I could work up the courage.

Jen was fingering herself with one hand while she cupped one of her small boobs with the other. I could smell the distinctive odor of her wet pussy as she stroked two fingers in and out of her. Taking in a deep breath, I released it slowly as I got out of bed, went over to hers and sat down next to her. She opened her eyes as the weight of my body tilted the mattress under her but then just closed them again as she continued without another moment of hesitation. At first I just sat there, my heart pounding as I looked at her pussy from as close a view as I had ever had.

Her fingers were wet as she put one of them in her pretty pussy and then used the others to spread the wetness over her pussy lips and clit. I couldn’t help but lick my lips in anticipation as her finger moved over her swollen clit making her body convulse as the pleasure it created spread out through her. I put my hand between my legs and felt my own wet pussy, the bare skin around it slippery from my pussy juices and moaned softly as I touch my clit and felt a shiver go up and down my spine. For the next few minutes I masturbated with her on her bed, the two of us next to each other but other than the feel of her bare hips against me as I sat there, still not touching one another.

I knew that if I didn’t do something soon I would lose my courage so with my heart beating so fast I was sure she could hear it, I took my left hand and gently placed it on her upper leg, letting my fingers lightly touch her inner thigh and then slowly dragging my fingertips over her skin which was as soft and warm as I had imagined it would be. Now THAT got her attention and she opened her eyes and stopped her masturbating. I took note that she didn’t take her hand off her pussy though which was hopefully it was a good sign.

“Um, Kelly ... what are you doing?” she asked softly, a sly grin coming to her face.

“Shhhhhh,” I replied softly as I lifted my hand off of her, “Nothing, don’t worry ... don’t let me stop you.” She closed her eyes again and soon started to finger herself again so I put my hand back on her leg again and this time she didn’t’ do anything to stop me. Encouraged, I let my hand move quicker over her silky smooth thighs, going from leg to leg but passing north of her pussy and over her belly as I did. Jen opened her eyes and looked at me as if seeing me for the first time.

“Kelly ... I mean really, what are you doing?” she asked but not stopping her masturbating this time. I didn’t say a word but just let my fingertips continue to lightly trace little circles as I moved my hands over her lower body. “Kelly, you know I have never done anything with a girl before,” she said, this time in a bit louder voice. “I’m not a lesbian!”

“Mmmmmmm, don’t worry Jen,” I said, trying to reassure her, “I’m not one either so don’t worry. I love boys but it can be fun with a girl sometimes.” Her body seemed to loosen a bit and she giggled when my fingers passed over her side just above her hips.

“Oh that tickles!” she giggled.

I slowly moved to her stomach and made little circle around her belly button. She giggled again and twisted just a bit as she said laughingly, “Kelly! Stop tickling me!”

I grinned at her and slowly worked my hand down to the top of the short line of pubic hair she kept when she shaved her pussy. “C’mon Jen, just close your eyes and imagine it’s Alex touching you.”

Fortunately her incredible lust for Alex won out over any concerns about me and she did indeed close her eyes and resumed her masturbating. Oh my god she looked so hot! She was so incredibly small yet had such a beautiful petite figure. Her pussy scent was so much stronger this close up and I licked my dry lips in anticipation of tasting her for the first time. I knew that I still had my work cut out for myself if I was going to make THAT part of my dream come true! I continued to slowly trace my fingers all over her body, moving from her legs to her hips (where I she was still incredibly ticklish!) over her tight little stomach and then at first just around her boobs which were so petite like the rest of her naked body. My fingertips moved in ever reduced spirals around her boobs until they were touching her pointed nipples.

Jen gasped as I pinched them softly between my fingers, pulling on them gently. I put my finger in my mouth to get it wet and then used it to rub her nipples, the moisture lubricating her hard nipple under my fingertip.

“Ohhhhhhhhh yes,” she moaned softly, “That feels soooooo good.”

Emboldened by her response, I worked my way back to her stomach and then just touched the top of her hairline of her close-trimmed pussy hair. Jen trimmed her pubic hair but didn’t shave it off the way I did. Apparently Alex liked to play with it and so she made sure there was some for him to have fun with. I gently lifted her hand off her pussy and place it on her breast. Her wet fingers immediately started to knead her boobs while mine went back to her now empty crotch. She was soaking wet from masturbating for the past hour and probably cumming at least once or twice in that time. My finger easily slid over her clit and I felt her tense up as I started to play with it.

“Oh I don’t know about this Kelly ... I just don’t know,” she whispered in a hoarse voice.

I noticed her hips were starting to move under my fingers so whatever uneasiness she was trying to vocalize, her body was betraying her true intent.

“Just imagine Alex’s big cock forcing its way into you,” I said as I began to push one of my fingers just inside her swollen pussy.