07/02/2016
My roommate left for a week on a business trip, and asked me if I would take care of his girlfriend while he was away. I had no problem doing that, and my mind instantly went to a very dirty place. She was one girl that I had always felt like I would have a chance to get around the bases with. She always sat very close to me on the couch when we watched tv, and often rested her hand in my lap or pulled one of my arms around her shoulder.
Whenever we would go out, she also loved to dress to show off her amazing cleavage. Plus, she would be even more handsy with me than she would be at home. I loved dancing with her, and she clearly enjoyed grinding on me. I would put my hands all over her, feeling her move and shake to the music. One night, after she had had several drinks, we were dancing and she moved one of my hands underneath her short dress to hold her bare ass. As much as I enjoyed giving it a good squeeze, I only held on for a few seconds because I was nervous about what my friend would say. Later that night, he asked me if I enjoyed what I felt, and told me not to worry about it. He liked that I got to have fun with her too.
On the first evening my roommate was gone, she came home from work. She worked in an office, and had worn a transparent blouse under a blazer with a black skirt. I watched her come in the door, drop her blazer and purse on the floor. As she walked toward the couch she reached up and unhooked her bra, then worked it out from under shirt. Her pale breasts shone beneath the sheer material, and her pink areolas and nipples were clearly visible to me. She smiled sweetly at my shocked look and then threw her bra in the direction of her room. Then she plopped down on the couch and swung her legs across my lap.
There was nothing else to do with my hands, so I rested them on her legs, feeling the silky smooth skin of her pale thighs. She made small talk with me for a few minutes, but I wasn’t really listening. As I looked in her direction, it was very difficult to tear my eyes away from her breasts, clearly visible under her shirt. At first, I wondered if she somehow did not realize that she was showing them to me. Then she told me a story from work that I did listen to. She told me that the office had been very hot today, so she had taken her blazer off. As she saw man after man subtly trying to gaze at her ample breasts spilling out of the bra under her shirt, she started to get very horny. She told me she had wanted to take off the bra all day so she could feel the thin material brush her nipples. But then she really shocked me. She told me then that she decided that since she had always wanted to show her tits to me, she would give me a little show when she got home. She had planned that for me! As she told me this story, she kept lightly brushing her hand around the edge of her breasts, and I could clearly see that her nipples were responding to the light touching.
I smiled, and moved my hands a bit more aggressively on her soft thighs. My hand was fully inside her skirt now, feeling between her thighs. She stopped her story, and smiled as she watched me feel her. She parted her legs slightly, allowing my hand to reach further. Then she laughed as she squeezed her thighs together, trapping my hand just short of her panties. “Careful!” She teased. Then she got up from the couch and went to her room.
I was worried that I might have gone a little too far for a second, but then I remembered that she told me she had planned that whole thing. She came out of her room wearing nothing but a thin, boob hugging t-shirt and panties that almost covered her ass. She spent the rest of the night on the couch with me. I played with her legs for most of the night, and enjoyed the feeling of her boobs on my arm when she leaned against me. It was getting hard for me to remember she was my roommate’s, but nothing else happened before we went to bed.