We had met online in an alternative lifestyle chat room. I had never really thought too much about the D/s lifestyle, but I always knew there was something more I longed for, something missing in my life that I wanted to give to someone and was never able to even recognize exactly what that was. A dear friend who I believe recognized this in me even before I did had directed me to the Castle website, and I was completely enthralled, reading everything I could find on the bdsm topic. I finally felt as if I had discovered that missing piece to myself, and it was a true joy, a falling into place of that last missing puzzle piece. When I read Jade's writings it felt as if she knew what was in my heart and my soul, and when I met Him I felt as if I had met my soul mate, finally.
It took me a very long time to work up the courage to actually agree to meet him, I was afraid, I had never done anything that sounded so crazy in all my life. To actually go off and meet someone from the internet seemed as far fetched as jumping to the moon. We had spent months and months preparing for the meeting, working out safety issues, so I would feel very safe at all times, and he had directed me to read things about the lifestyle including safety. We were both educated adults, and chose to embrace this as a lifestyle and not a sexual escapade or a game, and we were also both very concerned with being healthy and safe. And also very excited at the prospect of finally meeting, of being able to see into each others eyes, and touch each other for the first time.
We had planned 4 days in a location where I knew people and knew the area, so I could feel comfortable and free to leave at any time. He was flying in and renting a car, and we were meeting for dinner in a hotel restaurant, the same hotel where we both had separate rooms reserved. We had agreed that first night was strictly dinner and talking, no sexual contact or being alone in the room would be permitted on that first evening. And I was to bring a friend with me to stay for a drink and then leave when I felt comfortable. I was also to call my friend at designated times throughout the 4 days with a safe word we had worked out that meant I was okay and enjoying myself, or that I wanted her to come and rescue me immediately!
I was still a little nervous, but actually felt ready to meet him and to get on with my first D/s experience. I pulled into the drive of the hotel and was very pleased to see it was an attractive, very nice place. I checked in to my suite and reached for the phone to call my friend Kelli, who was joining us for drinks in the lounge very soon. She said she'd be over in a few minutes, so I decided to take a shower and get ready to meet him. The hot, steamy shower felt wonderful after the long drive downstate, and I was beginning to feel very relaxed yet very excited. I had always been an extremely tactile person, and the feeling of the hot water beating over my skin was very arousing.
For a moment I let my fingers trail down my body across my breasts and to my neatly trimmed blonde pussy, and I was very tempted to bring myself to orgasm right then and there, but I knew I needed to wait. That was part of our agreement, he would control my pleasure at all times, and my pain. I regretfully pulled my hands away and finished showering, getting out and drying myself off. I put the rose scented lotion all over my body as he had requested, dried my reddish blonde hair and began to get dressed. I was wearing a discreet black halter dress, high in the front and fairly low cut in the back, with black strappy little sandals. No nylons, just bare legs, no panties, no bra. I didn't really need one anyway, my breasts weren't large, but they were still firm, with rather large pinkish nipples and very sensitive. I finished my make up and sat down to wait for Kelli to show up.
There was a knock at the door and Kelli was there. We were so happy to see each other, it had been ages, and we had been friends for many years. She knew exactly what was going on as we had always been very close and told each other everything. That is why I chose the town she lived in to meet him. She looked great in a tight, blue very short dress and high heeled sandals. She always looked good, with her perfect little body and long dark hair, she was only 5'2" but she looked taller as she was all legs and breasts. She had actually had a breast reduction and was down from a 34DD to a 34C. We hugged and laughed and chatted away about how exciting this all was and how glad we were to see each other. We were just sitting down to talk when the phone rang. I answered it and it was him, ready to meet downstairs in the lounge.
"Hello Lynn, I was glad to see you had checked in right on schedule. How was your trip?" he asked me. "It was nice Jimmy, I am so glad to be here and Kelli is here too. Shall we meet downstairs then?" We made plans to meet in 15 minutes downstairs in the lounge as prearranged and said goodbye. My heart was now beginning to beat very fast, and I realized I was nervous! Kelli got me calmed down and out the door we went before I could change my mind. She gave me one last hug for reassurance just before the elevator door opened and we stepped out into the lobby. She was the only woman I had always felt comfortable having so much body contact with, that’s just how she was, very physical. We walked toward the doors to the lounge... I saw him as soon as I entered the lounge, he was sitting at the bar a fresh drink in front of him.
I recognized him immediately as we had exchanged several pictures over the past months. My heart jumped at the sight of him, in my eyes he was perfect. Tall, broad shouldered, dark hair with a goatee and mustache and very handsome. He must've sensed me as he turned on his barstool, and our eyes met for the first time. It felt like an electric shock in my abdomen, and suddenly I was calm and everything felt very right and very in place. He stood and walked across the bar to meet us, smiling. I couldn't help myself, my arms went up and around his neck and he pulled my body close to his for a brief hug as he whispered, "hi baby" in my ear. I introduced him to Kelli and saw the look of pleasure in his eyes at her beauty. I felt no jealousy, she was my best friend and I was proud of her and very glad she was there, for now. We sat down at a table, ordered cocktails as Kelli chatted away in her usual manner. We all laughed and talked easily, feeling very comfortable and really enjoying ourselves.
After a while he excused himself to use the men's room and Kelli leaned over and said, "oh my god, he is gorgeous! How are you doing? Are you okay?" I laughed and said, "I have never been more okay in all my life." We agreed that all seemed well and to progress with the evening as planned. She said she would be leaving soon but to be sure and call her if there were any problems or I felt uncomfortable at any time. We both had our cell phones in our purses just in case.
Jimmy came back to the table, we finished our drinks and Kelli said she had to go. He offered to walk her to her car, which seemed very sweet, as it was dark outside. She said no, that she would be fine and for us to enjoy our evening and she would talk to me tomorrow. She bent over and kissed me on my cheek, giving my hand a reassuring squeeze as she stood to leave. I really missed living closer to her and all the wild times we had together in the past. It was wonderful to see her again, and we made plans to spend time together on Saturday. We watched her saunter out of the bar and laughed after she left at her wild, outgoing way, she was truly a gem and a very dear friend. Then, he suggested we leave for the restaurant as he had made reservations and it was time to go. As we stood up and walked out the door I felt his hand on my bare back, and it gave me little tingling shivers all the way down my spine. I knew I wanted the feeling of his hands on me, and it was going to be a long wait until that moment finally came.
We went out to his car and got in, it was a hot evening and the air conditioner was on as he pulled out of the parking lot. I could feel my nipples tightening in the cool draft from the a/c and the sensation was intense, my nipples had always been so sensitive. He smiled over at me and said, "chilly?" staring directly at my breasts. I could feel my face turning pink. I hated that I got so embarrassed so easily but it was just how I was made, I had come to accept that about myself, and that was one of the things I loved about him, he never made me feel that my shyness was something to be ashamed of, rather something he liked about me. I just smiled back at him and said, "yes, I must be a little chilly."