Samantha Pt 7
Please go read part 1 through 6 before reading this...
After my surprising make out session with Ashley, I decided it was time for me to completely put Jennifer behind me and just date whomever I find and want to be with. I got back into working out and noticed a guy at the gym who I crossed paths with a few days a week. He was cute and wasn't there to be a show off or flirting with everyone, he was just there to better himself. One day we were both heading to the same machine and he gestured for me to go first. I thanked him and introduced myself. He introduced himself as Bobby. Bobby was about 5'10, medium build, with a bit of a pot belly (that I thought was cute) he had short brown hair and seemed like a normal guy. I wasn't quite sure of my feelings for him, but I liked talking to him and found myself more and more interested as we become friends. Plus, I needed some dick.
Bobby finally asked me out and we went for a bite one night after the gym. Over the next few weeks, we started talking, texting and hanging out more and I truly enjoyed getting to know him. We started dating exclusively in late October and began our relationship. It was weird at first being with a man again, but just like riding a bicycle again, I started riding Bobby. LOL. He was so nice and kind and made love to me like a woman should be made love to. We were working on building a great relationship and things were progressing as they should have. I was happy being with him and being back in a more normal situation. Almost two years later when I returned to work for the fall school year I found out I had to go to Nashville for a week-long training class on curriculum development. The classes were slated for in late October, a month before thanksgiving break and would be attended by teachers and administrators from around the U.S. According to the curriculum there were daily training modules and every person would attend all the modules throughout the week. The school booked me and three other new teachers into hotel rooms, each having their own and paid for everything including the travel costs. I was nervous to go, but excited.
Bobby and I celebrated our two-year anniversary just before I left and I hoped he could have gotten some time off of work to go with me, but unfortunately, he couldn't go. So, I ended up heading to Nashville by myself. I left my house early Sunday morning taking the 12-hour drive to Nashville. I arrived later in the evening, checked in, found out what rooms my co-workers were at in the hotel, had a bite and went to sleep.
Monday...And the start of my third lesbian experience.
My first day of class I sat next to a female Filipina Assistant Principle from suburban Indianapolis, her name was Anna. In conversations I learned she was here to add on to her credentials for a Principles job. She was very sweet, had medium length brown hair, brown eyes, a soft rounded Asian face, with sexy voluptuous lips, a medium sized build with normal to bigger sized tits and a great big smile. Anna was 45 and had been teaching for more than twenty years, with a recent promotion to AP. As the day progressed, we chatted more and got to know each other a bit. Turns out she was divorced and getting over a man she had fallen for a while ago and was just here to get away from the woes of back home. After the first round of classes ended, I headed to lunch and when I arrived at my afternoon training module, I saw Anna again. I went to sit by her because I knew no one else in the room and the other teachers from my school were in other modules. We worked in groups throughout the afternoon sessions and by the time the day was done we were all mentally spent. I went back to my room that night and just hung out with my other teachers from work.
I didn't see Anna on Tuesday, or Wednesday morning, but I did see her sitting in the hotel café at lunch time on Wednesday afternoon, so I asked her if I could sit with her. She seemed happy to run into me again and we spent the entire lunch hour talking about the classes and educators who were teaching. When it was time to go back, Anna asked me, "What classes I had and what time I was done?"
Unfortunately, we would not have any modules together today, but I told her maybe I'd see her later tonight because some of the teachers where going to the pool area to blow off steam after dinner. I had told Bobby along time ago about my lesbian experiences and he told me that he had been involved with some Transgendered women before and was "somewhat Bi-Sexual". On Wednesday afternoon when I talked to him on the phone, I guess I had mentioned Anna one to many times, because he asked me about her; implying she was all I could talk about. I did admit to him that I found her very beautiful, interesting and I was curious about her, but didn't want to do anything behind his back. Bobby said, "If something happens, I'm okay with it as long you tell me about it and I get some pictures. LOL."
Wednesday night pool party --
A lot of the teachers had come down to the pool area, there was a hustle and bustle throughout the room. People sitting around the pool deck and at tables drinking wine and conversing. I was sitting back with my co-workers enjoying a well-deserved glass of wine, when I saw Anna walk into the room. She was wearing this sexy white two-piece bikini over her light brown skin. Her body looked incredible. I was in awe. I hadn't even looked at another woman sexually since Jennifer, but I tell you the way she looked was stunning. Anna saw me sitting at the table, smiled and waved hi.
My co-workers asked who that was? I explained she was one of the AP's I had been working with the last few days. Anna came over and sat with us. I introduced her to everyone. After a bit of talk, I wanted to swim and so did Anna, so we excused ourselves and climbed into the pool. During our time in the pool, we started flirting with each other. We were trying to not be obvious with all these people around, but it was hard to hide. We spent time pulling each other through the water, throwing pools toys at each other, using the pool noodles to poke and prod each other and at one-point Anna even pulled the strings of my bikini top open. I was so enamored by her. I had feelings in my stomach that I hadn't had since my first few times with Jennifer. And even though I was with Bobby, I was absolutely attracted to her, and wanted to fuck her. But, did not know if she was Bi-sexual or even Bi-curious.
As the night progressed the pool area started to quiet down and people started to leave. Anna and I were sitting in the hot tub. We were sipping wine, laughing and enjoying each other's company. The last of my co-workers got up to leave and she gave me a dirty look -- as if she knew Anna and I were interested in each other -- almost angry that I was spending time with Anna and not her. Once everyone I knew was gone from the pool, I decided to make my move. As we sat, I placed my hand on top of Anna's hand and began rubbing over it. She looked at me and smiled. Over the next few minutes, our fingers swirled and twirled in and out of each other's fingers and rubbed around our wrist areas. I moved closer to Anna and whispered in her ear, "I am so glad I met you here."
Anna replied, "I am too."
I placed my hand on her leg and was slowly stroking up and down her leg. Anna didn't seem to mind and shyly smiled at me. We sat quietly staring into each other's eyes as I felt butterflies in my stomach. Every time someone walked by, we acted as if we were just chilling out and nothing was going on, but I think we both knew we were getting turned on for each other. I wondered if Anna had any experience with women, because I know she was married. Maybe she is Bi. Maybe just curious, maybe just drunk, either way I haven't had these feelings for a woman since Jennifer and I'd really like to kiss her right now. We sat a bit longer and Anna's hand was on top of mine as I rubbed up and down her leg. She opened her legs and pressed her left leg up against mine. I felt her guide my hand deeper between her thighs, but I never pushed my hand all the way up to her pussy, although I did slide up a bit further than I should have on occasion.
As her hand guided mine up and down and in-between her thighs a million thoughts ran through my mind. Did she want me? Was she just being a flirt? Should I move further up and touch her? We kept our conversation going as if nothing "out of the ordinary" was going on. I was confused on what I should do. We smiled at each other a lot, starred into each other's eyes, but neither of us made a distinct move. Maybe because people were still here at the pool, maybe she was scared to, maybe she wanted to, but wasn't sure if I was interested. Either way we both sat there and neither of us made a move. As the night was winding down, I knew I had an early start tomorrow and as much as I want to stay here with her, I said, "It's getting late, I think it's time for me to head back to my room."
