After having to wear a shell in public, then having an orgasm in the presence of my friends and watching my friends have an orgasm virtually naked, I didn’t think that any of the challenges could get any worse. I was wrong.
A few weeks later, I was talking to my friend on the Internet and I was telling him about how my friends Terra, Cindy and I had been talking in bed one night and we were discussing our fantasies. I mentioned that Terra’s fantasy was to sleep with another woman to see what it was like. I should have kept my mouth shut. I mentioned to him that I thought she was very good looking (for a woman). He mentioned having sex with her and I immediately shot that idea down. That was not in my realm of thinking or even close to something I would be comfortable with.
So my next challenge was to let Terra give me a full-body massage. Here was the kicker. I had to let her touch my breasts and vagina for at least one minute each. I vetoed the challenge, until I had the right to tell her to stop at any time, if I felt too uncomfortable. At that point I agreed.
Saturday night arrived and I was very nervous, so Terra and I chatted awhile and just hung out. I could tell how excited Terra was to be able to give me a massage, even though she didn’t say it. She had a twinkle in her eyes. We went over the details of the challenge before we got started and I felt somewhat comfortable, was as comfortable as I possibly could at this point. Several times during the night I considered canceling the challenge. “I was too conservative for this,” I told myself. It was only a full-body massage after all and I didn’t have to have sex or anything.
I lay face first on my bed with nothing but black panties on as Terra entered the room. Terra had brought a few candles with her, which she lit to give the room a relaxing aura. Terra was only wearing a t-shirt and panties herself. She slowly climbed onto the bed and gently straddled my hips. I was very tense and nervous, but there was no stopping now.
Terra began by softly massaging my shoulders and my neck. She talked to me while she was giving the massage, which helped relax me a little. She massaged my shoulders and neck for probably five minutes before she began moving her hands down to my shoulder blades. Her soft hands felt very relaxing, though I didn’t want to admit it.
My eyes were closed and I was enjoying the feeling of her soft, gentle hands working on my upper body. Her hands continued down lower and I tensed a little. Her hand moved down to my hips and she masterfully massaged out the knots. The mixture of my relaxation and the candles helped me drift into an almost trance-like state. As her hands moved down to my butt cheeks I became a little nervous again, wondering if she would go in deeper. She massaged my outer cheeks first and then slowly moved inward. When her hands were to the point they were practically touching each other, Terra began to lift my hips. I instinctively helped as she removed my panties.
I was embarrassed because I knew there was wetness in the crotch area of my panties. Here I lay naked, with a female mounted on my body, massaging me. This was my best friend to boot. I tried to let my mind wander as she slid her hips down onto my upper thighs and massaged my butt. What happened next shocked me.
As she was talking to me about her visit with Doc at the hospital, she spread my ass cheeks a bit and began massaging my anal opening. I almost cancelled the whole damn thing right there. I had never had anyone touch my butt that way and it was very uncomfortable. After a few seconds passed I was surprised by my body’s reactions. I began to feel my body warm up and wetness form inside my vagina. The problem was that I was enjoying her fingers a little too much. The pleasure of the massage was transferring from relaxing to exciting and I wasn’t sure I was comfortable with that.
I let out a very soft moan and hoped that Terra didn’t hear it as her hands moved down to my legs. Her fingers worked their way down to my feet and then back up to my inner thighs. At this point, she asked me if I was comfortable. I wanted to say no, but I didn’t. For some reason I wanted her to continue, though I thought I would never have felt that way.