Tammy

I met Tammy a few years ago. There is a local coffee shop where the owner would display local artists on the walls. I don't consider myself much of an art buff, but I noticed one of Tammy's paintings, and it caught my attention. It was an abstract piece, almost like a Salvador Dali or a Picasso. I really liked it, and it was very reasonably priced. At the bottom of the painting, on the frame, there was her name and email address. I sent her an email asking questions about her painting, and for more information. A few days later she responded to my email, asking when I wanted to meet her at the coffee place, and discuss her painting in further detail. I made plans to meet her the following week.

When I finally met Tammy, she wasn't at all what I expected. I imagined her as an older woman, maybe in her forties, quiet, artistic, deep, ect. She turned out to be much younger than I imagined, I guessed maybe seventeen years old, (twenty four, I later found out) and she was a little quirky or nerdy. We talked about the painting for a few minutes before I finally decided to buy it. She gave me her phone number and wanted to set a time for me to visit her place, too look at more of her paintings. I wasn't going to call her, but I really did like her work, plus she was pretty cute. On my way out to my car I noticed she was carrying another painting into the coffee shop, to replace the one I bought. I didn't get a good view of it, but from what I remember seeing, it was another really good piece. I decided to call her and set up an appointment.

A few days later I called Tammy to look at more of her art works. I wasn't planning on buying anything, but I really wanted to see what she had to offer. Plus she was really cute, and I thought maybe I'd try my luck at asking her out if things went smoothly. She agreed to have me over to her place to have a look at what she was selling. When I arrived, Tammy greeted me and invited me in. She was looking very sexy, and I immediately noticed a strong attraction to her. I wasn't sure if she shared that same attraction with me, as she was mostly just trying to sell me paintings, and keeping it strictly business. I ended up buying two more of her paintings. She was very happy to be selling her art works, and mentioned I was her first buyer ever. I told her I was happy to oblige and offered to take her out for drinks sometime to celebrate. She accepted my offer, out of excitement, and we made plans for that following evening.

I met Tammy the following evening at a local  jazz lounge, Jay's Bistro. I noticed she had a new Louis Vuitton purse, probably bought with the money I paid her. I complimented her on her purse, and she seemed impressed by my knowledge of fashion. We ordered a bottle of champagne to celebrate. We had a few glasses, and eventually finished the bottle. Soon after we ordered more drinks, and we were getting good and drunk. By that point I didn't feel as if she was into me, and I wasn't sure why at the time, so I just kept it casual. I could tell she had a few too many, because her speech started too slur and our conversation became  more bolder. She mentioned at some point, that her friend Gary, would absolutely adore me. I was very confused by that. Did she think I was gay? I asked her why she thought that, and she laughed and said "you're gay aren't you?" She mentioned my taste in art, my knowledge of women's handbags, the swanky jazz bar, my nice clothes and peak physical condition. I laughed for about a good five minutes, uncontrollably, and assured her I was straight. She refused to believe me at first, insisting I fit most gay stereotypes. It took a little convincing, but eventually, she believed me. She looked more embarrassed than anyone I've ever seen. We both had a good laugh after that, and that's when I noticed she seemed a lot more interested in me. She asked me "are you single?" I assured her I was, and she said "I can't believe someone like you is single." We talked and flirted with each other for about another hour, before she decided it was late and she needed to head home. I called her a cab, while she was in the restroom, because clearly she wasn't ready to drive. After she came back from the restroom I told her a cab was on the way, and she thanked me. When the cab arrived I walked her out and helped her into it. She kissed me softly on my neck while I did that, and thanked me for being so sweet and understanding. I gave the cab driver a twenty and told him to take her home.

The next day Tammy called me and wanted to apologize for her behavior the night before. I assured her an apology wasn't necessary, but she insisted on it. She mentioned how rude it was for her to make such an assumption of me. I told her it really wasn't a problem and offered to take her out again. She asked if it would be a date, and I told her I was feeling a little demasculinated after my sudden realization that everyone might think I'm gay. I told her I always thought she was cute and mentioned yes it would be a date. After a little hesitation, something about not wanting to get involved with clients, she eventually agreed, and we made plans for the following evening.

I picked her up the following evening, and we set out for dinner and drinks at one of my favorite date spots, The Moot House. She was looking very sexy that evening, wearing a spaghetti strapped shirt and a skirt. I immediately started flirting with her and hitting on her. She responded to my advances with a little flirting of her own. I started feeling a strong sexual tension between us. During the course of our meal I started making more vulgar sexual advances and suggestions, just to see where the line was, and each time I thought I might have crossed it, she responded positively to my crudeness. It's rare to find a girl like that, a girl that likes you so much, they let you get away with just about anything. They will usually do almost anything to please you, but that period of time usually only lasts for so long. Eventually she asked about her paintings. I told her I had them framed and hanging in my living room, and she insisted she wanted to stop by my place after dinner to see it. I knew that was just her way of saying "take me back to your place and make love too me" but I played along anyways.

Soon after dinner we set off for my place, so she could see her paintings. I poured us a few glasses of wine while she examined her art work. She was very impressed with the frames I bought for them, and how they were displayed. We sat on my couch and drank our wine, while we examined her art work and chatted casually. It didn't take long before I made my move, leaning over and kissing her. We kissed for several minutes, before I started exploring her body with my hands, and slowly undressing her. She was a little chatty while I did this and I found that very annoying. I usually try to pay attention to what I'm doing while I'm kissing someone, but she seemed more focused on keeping the conversation rolling. Eventually I made me way up her skirt and started fooling around, thinking maybe that would shut her up, but she was still talking my ear off, making it very hard for me to get in the mood. Try to imagine yourself in my position, you have your fingers inside a cute girl, trying to please her, and she keeps saying stuff like "oh you're good at that" "I bet you do this to all the girls you meet" "I still can't believe I thought you were gay" "I can't believe I'm letting my first customer get this far" It's gets really annoying. It was very hard for me to tell what she liked ,or whether or not if I was even turning her on. I thought maybe she'd stop talking if we were having sex, so I offered to take her into my bedroom. She accepted, and I led her into my room, by the small of her back.

The sex, at first, was no different than the foreplay. She kept talking to me, even while I was inside of her. It was a very unusual experience for me and I really didn't like it. I've had girls talk to me in bed before, but it was usually just short quick instructions like "faster" "deeper" "that hurts" "oh god" "oh daddy" or even "wrong hole" Tammy was more interested in having a full out conversation with me. It made me feel as if I wasn't doing a good job, and I couldn't get her in the mood. It was very hard for me to focus as well. Eventually, out of sheer frustration, I said "shut up and take my cock." That little phrase immediately turned her on, and just after I said that, she started moaning. It took maybe twenty seconds, before I made her cum. She got off several more times over the course of the next fifteen minutes, before I myself finished. I rolled over onto my side and she mentioned my little phrase. She said something about how that turned her on more than she had ever been in her life. She said she loved how I took control and showed her my dominance, and how it really turned her on that I talked so dirty to her. I didn't have the heart to tell her that phrase was actually literal, but at least now I knew what to do in the future.

I dated Tammy for a few weeks. I told her I wasn't looking for anything serious, and she assured me that was fine with her. She seemed mostly interested in sex, which was fine with me. I told her the dirtiest things every time we had sex, and she just loved it. It seemed like the more aggressive I was with her, the more it turned her on. After a few weeks had passed I started hearing less and less from Tammy. It was to be expected, we both knew our sex fueled fling wasn't going anywhere. After a few weeks of dating, we lost contact.