Jessie’s Fantasy:Chapter 1Losing a Bet

Nearly everyone has a sexual fantasy that they would love to act on sometime in their life. Unfortunately for some, it never becomes reality. There are many different reasons, ranging from having fear or hesitation, to fantasizing about someone they can’t have, or the situation just never presents itself. This is a story of one such fantasy. Hope you enjoy! It was a Friday evening and I was on my way to meet my usual group of friends. The eight of us had been friends since high school, and we were a tight group. Our usual Friday and Saturday night would entail going out to a bar or nightclub to relax, have fun, and most of all meet women. The majority of my friends had the knack. They could go out and hit on some very attractive women without missing a beat. Sometimes they succeeded, and sometimes they failed, but they never hesitated. I was the shy one of the group, especially when it came to women that I found highly attractive. I would never approach the women I was attracted to, but instead would admire them from afar. Now I did have several female friends, but as I was shy, I never asked any of them out on a date even though I wanted to. One Friday night we were at our usual hangout. A simple dive bar, always busy, and the bartenders Escort ankara knew us all by name and what we liked to drink. On the TV, the Dodgers and Giants baseball teams where hammering it out. The Dodgers had a commanding lead 6 to 1 at the bottom of the eighth inning. My friend John said, “Anyone want to bet that the Dodgers will lose?” I looked at him like he had a screw loose in his head. I retorted, “Have you gone loony? No way will the Dodgers lose. The Giants will be at the bottom of their order and no power hitters will be up to bat.” “So it’s a bet?” John replied. I quickly said, “What’s the wager?” “Whoever loses, will have to go out with the group dressed up as a woman, and get a phone number from a guy. Loser has to keep going out dressed as a woman until they succeed in getting a number.” I laughed really loud, “You’ve really lost it Johnny boy. I’ll take that bet!” We shook hands, and several friends vouched as witnesses. They all commented that John was a sucker and made a really stupid bet. As the bottom of the eighth inning progressed, the Giants scored a run. 6 – 2. Eventually, the Dodgers retired the side. I was feeling pretty good, knowing there was a four run difference with three Balgat escort outs left for the Giants. When the ninth inning started, the Dodgers quickly loaded the bases. I turned to John and said, “Be prepared to wear a dress for a long time.” The Dodgers scored two runs before the third out. It was now 8 – 2 and I was smiling and ribbing John for such a poor bet. All of my friends were laughing and giving John major crap about what a manly looking woman he would make and no guy would want to give him their number. The bottom of the ninth came, and the Dodgers quickly dispatched two Giants batters. Then it all started. The Giants got on a roll. Soon it was 8 – 5, and bases were loaded. First pitch and the batter connected to the ball. I will always remember the announcer say, “It’s a deep drive to center field! The center fielder is back at the warning track, and gone! The Giants won with a grand slam!” All the blood drained from my face, and I placed my forehead on the table. All of my friends were totally stunned with the exception of John who rightfully let me have it and gloated on how he won the bet, and I would be the one wearing the dress. As we left the bar, all my friends started teasing me saying Batıkent escort bayan I would look sexy as a woman. Finally they said, “Okay, Jesse, can’t wait to see you all dolled up tomorrow!” They laughed as I got into my car. I got home and had a heck of a time falling asleep because I was wondering what I had gotten myself into. Saturday morning, I called my good friend Tracy and asked her if I could come over and ask a huge favor. She told me to come over whenever I wanted. Tracy is my best friend. We were always there for each other through thick and thin. She was one that I always wanted to date but was too afraid of being rejected by her. Tracy had several boyfriends over the years, yet none of them became serious. I always provided advice even though deep down I was envious of the guys she dated, as I wanted to be in their position. I rang the door bell, and Tracy answered. “Hi Jesse! What is going on?” She gave me a big hug, I could feel her soft breasts press against my chest and I was starting to get aroused. “Come on in, Jesse and let’s talk.” I walked into her house. “Tracy, I hate to ask you this, but I took a bet with my friend John and lost big time.” “How much money did you lose? I can spot you some if you need it,” Tracy stated. “It isn’t money that I need. I need someone who can help me look like a woman,” I replied. Tracy gave me a funny look and said, “Is there something about you I didn’t know about?” I proceeded to tell Tracy about the bet and how it went from a sucker bet to one that I completely lost.