Jessies surprise part 2
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Jessie's Fantasy: Chapter 1 Losing A Bet free porn video
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 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 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 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. Also mentioned is that I have to dress up starting tonight. Her funny looks changed to one of sympathy then to pure laughter. “Jesse dressed up as a woman! I have to see this.”
After Tracy stopped laughing, she finally said. “Okay, Jesse. I have a couple of friends I can call, and we’ll help you out. One of my good friends is a cosmetologist, and another works at a woman’s department store. I’m sure we can help you out. I need to know a couple of items so we can get you the best fit possible. But first, we need to take care of some man items as women do not go out without being well groomed.”
Tracy took some measurements of my hips, chest, waist, torso height, and inseam. After that she proceeded to start a bubble bath for me. “Get naked and hop in the bath. I’ll make a couple of calls and help you get prepared for your transformation.”
With that, she left the room. I started soaking in the tub and started thinking what was going to happen. The more I thought about my dilemma, the more aroused and hard I became. I got lost in my thoughts and started playing with myself.
Just then, Tracy came in and said, “Jesse, I got a hold…” She paused as she stared at what I was doing. I stopped in embarrassment and apologized to Tracy.
Tracy replied back, “My, my Jesse. It looks like you are really aroused by this being a girl bet. I’m thinking that you were hoping you would lose.” As she stated this, she took off her shirt. A nice firm set of breasts secured in a sexy red laced bra popped out. I got harder yet.
“You know, a real girl doesn’t have a big hard penis when she gets aroused. If you want to pass as a woman, we’ll have to take care of this.” She placed her hand on my penis and stroked it gently. Tracy then proceeded to take off her bra, pants, and panties. My jaw dropped. Before me was a totally naked goddess. Tracy was a perfectly formed woman whom I loved, but never once conveyed that to her. She gave me a sexy smile, leaned over, and gave me a soft passionate kiss. I was stunned. Did this just happen?
Tracy gave me a couple more passionate kisses as she stepped into the tub. No words were spoken. It was just a silent understanding that something magical was going to happen. Tracy took her hand and lined up the head of my penis to her womanhood. She continued to lower herself onto me. As I entered her, she let out a small gasp as she lost her breath. Tracy was in control. She quietly let me slip deeper inside of her. I was in heaven. I never imagined in my wildest dreams that I would be having sex with my best friend and one who I secretly loved.
Our lovemaking was pure magical bliss. We shared many deep passionate kisses as she slid up and down on my manhood and rocked back and forth. All of this motion was getting us hotter and hotter for each other. We still hadn’t spoken a word, yet I could see by the look in her eyes that she was enjoying our lovemaking session.
As both of our climaxes were building, she quietly said, “Oh my god Jesse. You have no idea how long I have been waiting for this moment. Ever since we became friends, I started falling for you. I have fallen in love with you. I have never had anyone take my breath away from me as you have done today.” Tracy was losing her breath as her climax continued to build. “Oh god, Jesse, you feel so good inside of me. I want you to cum. Please cum inside of me. I have never wanted to have a man cum inside me except for you. I love you Jesse!”
She lost her breath again and her body started shaking. “Oh god! Oh god! Oh….” Tracy’s orgasm took control of her body and she shook uncontrollably. I could feel her pussy contract around my penis. The sensation was too much for me.
“Oh, Tracy, I am going to cum!” I pushed myself into her as deep as I could. I shot several shots of cum deep inside of her womb. After our orgasms subsided, she laid on top of me. I was still inside of her while she lowered her breasts onto my chest, and nestled her head by my neck. We remained that way until the bath water got cold.
“I love you, Jesse. I always have.”
“I love you too, Tracy.”
We put more hot water into the bath tub, and Tracy displayed a woman’s razor and shaving cream. Tracy sensually applied flowery scented Skintimate all over my legs. She started removing all of my leg hairs and then proceeded to move her way to my stomach and then my underarms. Tracy spent the better part of an hour making sure that all of my body hair was removed. I was really amazed at how good I felt and how smooth Tracy shaved me. Tracy applied a womanly scented lotion all over my body. While she was rubbing the lotion in, we started making out again. I was staring into her beautiful doe eyes and then I moved in to kiss her, only to be interrupted by a door bell.
“Well, Jesse, it looks like my friends are here to help you with your transformation to a woman.”
With that, she walked out of the bathroom still naked and answered the door.
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 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 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 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. Also mentioned is that I have to dress up starting tonight. Her funny looks changed to one of sympathy then to pure laughter. “Jesse dressed up as a woman! I have to see this.”
After Tracy stopped laughing, she finally said. “Okay, Jesse. I have a couple of friends I can call, and we’ll help you out. One of my good friends is a cosmetologist, and another works at a woman’s department store. I’m sure we can help you out. I need to know a couple of items so we can get you the best fit possible. But first, we need to take care of some man items as women do not go out without being well groomed.”
Tracy took some measurements of my hips, chest, waist, torso height, and inseam. After that she proceeded to start a bubble bath for me. “Get naked and hop in the bath. I’ll make a couple of calls and help you get prepared for your transformation.”
With that, she left the room. I started soaking in the tub and started thinking what was going to happen. The more I thought about my dilemma, the more aroused and hard I became. I got lost in my thoughts and started playing with myself.
Just then, Tracy came in and said, “Jesse, I got a hold…” She paused as she stared at what I was doing. I stopped in embarrassment and apologized to Tracy.
Tracy replied back, “My, my Jesse. It looks like you are really aroused by this being a girl bet. I’m thinking that you were hoping you would lose.” As she stated this, she took off her shirt. A nice firm set of breasts secured in a sexy red laced bra popped out. I got harder yet.
“You know, a real girl doesn’t have a big hard penis when she gets aroused. If you want to pass as a woman, we’ll have to take care of this.” She placed her hand on my penis and stroked it gently. Tracy then proceeded to take off her bra, pants, and panties. My jaw dropped. Before me was a totally naked goddess. Tracy was a perfectly formed woman whom I loved, but never once conveyed that to her. She gave me a sexy smile, leaned over, and gave me a soft passionate kiss. I was stunned. Did this just happen?
Tracy gave me a couple more passionate kisses as she stepped into the tub. No words were spoken. It was just a silent understanding that something magical was going to happen. Tracy took her hand and lined up the head of my penis to her womanhood. She continued to lower herself onto me. As I entered her, she let out a small gasp as she lost her breath. Tracy was in control. She quietly let me slip deeper inside of her. I was in heaven. I never imagined in my wildest dreams that I would be having sex with my best friend and one who I secretly loved.
Our lovemaking was pure magical bliss. We shared many deep passionate kisses as she slid up and down on my manhood and rocked back and forth. All of this motion was getting us hotter and hotter for each other. We still hadn’t spoken a word, yet I could see by the look in her eyes that she was enjoying our lovemaking session.
As both of our climaxes were building, she quietly said, “Oh my god Jesse. You have no idea how long I have been waiting for this moment. Ever since we became friends, I started falling for you. I have fallen in love with you. I have never had anyone take my breath away from me as you have done today.” Tracy was losing her breath as her climax continued to build. “Oh god, Jesse, you feel so good inside of me. I want you to cum. Please cum inside of me. I have never wanted to have a man cum inside me except for you. I love you Jesse!”
She lost her breath again and her body started shaking. “Oh god! Oh god! Oh….” Tracy’s orgasm took control of her body and she shook uncontrollably. I could feel her pussy contract around my penis. The sensation was too much for me.
“Oh, Tracy, I am going to cum!” I pushed myself into her as deep as I could. I shot several shots of cum deep inside of her womb. After our orgasms subsided, she laid on top of me. I was still inside of her while she lowered her breasts onto my chest, and nestled her head by my neck. We remained that way until the bath water got cold.
“I love you, Jesse. I always have.”
“I love you too, Tracy.”
We put more hot water into the bath tub, and Tracy displayed a woman’s razor and shaving cream. Tracy sensually applied flowery scented Skintimate all over my legs. She started removing all of my leg hairs and then proceeded to move her way to my stomach and then my underarms. Tracy spent the better part of an hour making sure that all of my body hair was removed. I was really amazed at how good I felt and how smooth Tracy shaved me. Tracy applied a womanly scented lotion all over my body. While she was rubbing the lotion in, we started making out again. I was staring into her beautiful doe eyes and then I moved in to kiss her, only to be interrupted by a door bell.
“Well, Jesse, it looks like my friends are here to help you with your transformation to a woman.”
With that, she walked out of the bathroom still naked and answered the door.
Brandy
- 09.12.2022
- 23
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- Category:
- Crossdressing
