It started as an online lark. Jennifer was into playing and I enjoyed how detailed and stimulating she was, making it impossible not get hard just seeing HotwetnReady was online.
My infatuation started with her picture. She was like a wet dream, blonde, long erotic legs and perfect tits that would make any man stare no matter where or when you saw her. Each time we enjoyed each other she'd send me a new picture, showing just a little more. First her naked breast, nipples erect as she pinched them. Then Jennifer sent a photo of herself on her knees with just a glimpse of her tits and beautiful ass. She looked so coy and seductive and she'd attached a note "a picture of me wishing you were here to fill all my needs." I knew our relationship was more than an online fantasy when she finally sent a picture of her shaved pussy filled with a massive dildo with the note, "I have to find something to fill my emptiness, wish you were here."
The fantasies started to get more intense and we progressed to enjoying phone sex. I couldn't believe how her voice effected me the first time I heard her whisper how much she wanted me on the phone. Her voice could nearly make you cum, especially when Jennifer would say "Please baby fuck my hot tight pussy, I'm so wet, I just want you inside me, please fuck me hard Jason." Jennifer always got me off and she would make it so so real when we role-played our fantasies.
Jennifer confided in me that she was involved in a lifestyle I might not believe and although she wouldn't tell me any details my curiosity began to drive me crazy. From time to time she'd ask me if I had ever enjoyed group sex or ever considered being with another couple. It occurred to me that maybe our little games were tame compared to Jennifer's real lifestyle.
We role-played with another couple online once, really just fucking together in the same chat room, the other couple was almost as detailed and descriptive of their sex play as Jennifer and I had become, even though we never really engaged in anything like group sex, but I think I'm getting ahead of the story.
We'd discussed meeting for real a few times. Since I traveled to LA occasionally we role played turning our fantasies into a reality - I actually had a trip coming up and for the first time I was seriously considering making her my first real-time exploration with an online partner.
When I finally got up the courage to tell her I wanted to spend a weekend with her she told me it could only happen on one condition - I had to agree to join her for an adventure in a no holes barred fantasy weekend - totally committed to doing whatever was required. I didn't think with anything but my cock and curiosity, which had me so hooked I agreed almost immediately - I had no idea... That's where this story begins...
My plane arrived in the early afternoon and I was prepared to find a shuttle to the hotel when I noticed a limo driver with a sign "Jason Miller" I did a double take. I've walked by those guys a 100 times, but never had one looking for me. She actually recognized me and took my bags while I was still in shock. She introduced herself as Linda and lead me to a stretch limo "Get in and relax. From now just relax everything you desire will be done for you." With that she got me my favorite drink and then after giving me a delicious view of her tight ass closed the back door and got into drive.
My mind started to spin as she drove, and I began to wonder what Jennifer had in mind. For the first time I began to get butterflies and sweaty palms wondering what I had gotten into. I had the impression that Jennifer had money, but this fantasy felt like it belonged to a world I'd only read about. Even Linda's tone, when she said, "everything you desire" had an envious to it as if she knew what sexual adventures awaited me. I enjoyed my drink and tried to relax.
Linda, parked in a private underground parking garage and lead me into a very upscale spa, I was greeted by a man who had to be a model - perfect body, perfect face, he was incredible. I mean this guy - even other guys would be jealous of him - he was so sexy. He was dressed in a long loose robe. Stephen, who informed me that this was to prepare me for this evening and said "This is going to be an afternoon, Jason, you'll remember for the rest of your life." Even his voice was sultry and I was surprised how sexy I found it. I was beginning to wonder when I'd actually meet Jennifer, but I went along. Stephen lead me into a private dressing room and "You will not need your clothing any longer." I'm not a prude, but this made me wonder. Stephen started to undress me and I wasn't prepared for that. He assured me "This is part of the service and just relax and let myself be pampered". I now began to wonder why everyone was telling me to relax.
I started to stutter an objection and for a moment Stephen looked me in the eye and said "You shouldn't forget you agreed to 'do whatever was required." I thought, "how bad could it be?" – although after his quote of a private e-mail conversation, I was wondering if Stephen was part of this fantasy weekend, in some way Jennifer and I had never explored. If you're a guy and you've never been undressed by another guy before, I can't describe quite how it felt. Lets just say it was a lot more surprising than getting picked up by a limo at the airport. I have to say just being this close to Stephen even clothed was some how sexually charged. You should know I consider myself straight and have had some bi-curious fantasies before, especially in my teens.