Jessie’s Fantasy Chapter 5: Afterthoughts

Ahegao

After Tracy mouthed, “I love you” to me, I knew right then and there that Tracy not only loved me as a male but also me as Jessie. I could feel my cheeks get warm and flushed from her comment and my thoughts. This was turning out to be the best day of my life. My thoughts were interrupted when Mark’s cock softened to the point that he slid out of my backside. Now my thoughts were replaced by something totally different.It was the thought of sudden emptiness. Something that truly belonged, but is now vacant. As I was coming down from my orgasmic high, I suddenly felt that a part of tonight was gone forever. A small frown replaced the expression of fulfillment and pleasure. Then it hit me. I had just experienced something new and way outside my comfort zone. It was something that I feared just hours ago as I was getting ready to fool my friends. It was the pleasure of experiencing what a woman experiences with their mate. It is the experience of a male penetrating a woman’s most intimate area, and I already missed the feelings that washed over me when I was riding Mark.When I finally raised myself off of Mark, his semen was already dripping out of my boy pussy and in between my thighs. Part of me thought it was dirty and slutty, yet another part of me felt it was one of the most intimate feelings a woman can have. I curled up next to Mark and placed my head on his chest while we watched the orgy continue to progress on the floor in front of the fireplace. John had finished with Tracy, and when I looked over to her, she made a yawning motion. I knew that meant that she was not impressed by John’s handling of a woman. Deep down, I had a feeling that would be the case as John always tended to think about his own needs and not the needs of others. For tonight, I was grateful that he also acted that way while bedding women. The last thing I wanted was for John to be a superior lover to Tracy, and then he beats me twice.After the sexual escapades were completed with Brooke, Suzy, Adam, and Brian, us girls bid the guys a farewell kiss, and then hopped into Tracy’s car for the ride home. Once in the car, Tracy opened up, “Sweet mother! You sure were a hot one there Jessie!”Suzy replied, “I have never once had an urge to stop in the middle of having sex to view something. You were absolutely gorgeous riding on Mark’s cock. It looked so natural and you were just glowing from what he was doing to you. Are you sure you’ve never done this before?”I nodded my head. “He took my cherry! I could not believe the wash of emotions that overcame me while I was riding him. I was so surprised how natural it felt, and how aroused I became. When it was all done, I felt content, yet empty inside.”“Well, Jess. That’s exactly what I feel like when a guy totally satisfies me. I hate that moment when he slides out of me as well.” Brooke stated.“So I have a question. Did you hear me say boy pussy and make me a woman to Mark?” I asked.Tracy replied, “Yes. I thought for sure that you blew your cover. I can’t believe Mark didn’t freeze up and call you out on it.”“I was terrified that I was caught.”Tracy finished the conversation with, “So, let’s all go back to my place and celebrate Jessie’s first successful night as a girl, and for many more adventures!”I blushed and started thinking about Tracy’s last statement, ‘Many more adventures’. Did Tracy intend to do this more often with me? I have to admit, it was an intriguing thought of doing this again, yet part of me just wanted to be my old self. More conflict rose within me now that I had a man. I Escort ankara am totally into women, and not men. Yet having that cock in my mouth and the power I felt over Mark when I told him it was that time of the month, was something totally different. However, now I wanted to be a man, yet also be a woman. I was so conflicted that I wanted cock and pussy. One day is all it took to go from a completely heterosexual male into a confused potentially bisexual cross-dressing sissy. I was about ready to tell Tracy never again will I dress up as a girl. But then I remembered Brooke’s comment to me before entering Adam’s house. Tracy absolutely loves cross-dressing men. Maybe Tracy really wants a submissive male willing to be a sissy. Maybe she wants to share a sissy boy with other men. Whatever other questions that came up in my mind about Tracy’s wants and desires, none of it had to do with me just being a man with her. It all revolved around me being her sissy boy boyfriend willing to do anything for her. Surprisingly, I was beginning actually enjoy those thoughts, to let go of some of my masculinity, to be very much in touch with my feminine side. It was definitely something that I need to approach her about when the time is right.We got back to Tracy’s house and settled in. After a final drink, we all retired to Tracy’s king side bed. All of us slipped into some comfortable nightwear. Brooke gave me a sexy hot pink babydoll to wear to bed. I put that on and instantly fell in love with it. It was so sexy and comfortable to wear. Once I laid down on the bed, Tracy got in bed behind me and spooned me. I felt so feminine with her arm wrapped around my body. Brooke slid into my front side so I was spooning her. She quickly noticed that my boy clitty was in between her butt cheeks. A little snicker came out of Brooke as she purposely lifted her left leg slightly and backed up into my crotch. Then she lowered her leg, effectively trapping my manhood between the flower petals of her womanhood. I swore I felt some fingers wrap around the tip of my cock. Suddenly she backed up a little more, and I felt some resistance. Brooke was insatiable tonight. As my cock slid inside of her, she gave a little moan of content.Suzy, in turn, snuggled up against Brooke, completing the pile of women on the bed. We all quickly drifted off to sleep. A huge smile was on my face knowing that Tracy was with me and that I had fooled my friends tonight. It was the first night of my new life.********************************************************************I woke up around 9:00 AM to my cell phone ringing. Tracy and Suzy were already up, making coffee and breakfast for all of us, and Brooke was still next to me in bed. I tried to ignore the phone, but after a couple seconds of pause, the phone would just start ringing again.Picking up the phone, I answered, “Hello?”“Jesse! Where the hell were you last night?” the voice on the other end asked.It was my friend Mark. My heart skipped a beat from hearing his voice. Finally, I calmed down and replied, “I had some business to take care of.” “Well, did you miss out last night! The nightclub was just rocking!”“Oh yeah?” was my response.“We met up with four real hot ladies last night. They were smoking hot. Damn! I couldn’t believe we got so lucky to meet up with them. Oh, Shit dude! They were the hottest, most sexy gals we’ve met in a long time!” Mark was obviously excited.“That’s cool Mark. Sorry, I missed it.” I answered.Mark quickly replied, “Hold on! Let me tell you Balgat escort what happened! They ran into us at the nightclub, and we quickly paired up. The girl that I had, oh my god she was incredibly on fire! Oh, how I wish I could remember her name right now.” The smile on my face was replaced with a slight frown. He’s had so many women, he doesn’t even remember the name of the woman he last slept with. I felt dejected and slightly insulted.“Well anyways. We got them to go with us to Adam’s house for a little post nightclub fun. Two of them started stripping and eating each other, while this hot babe was all over me like a cock thirsty slut.”So now I went from hot, to on fire, to a hot babe, to a cock thirsty slut, real classy there Mark. Even though I not only felt dejected, slightly insulted, and now majorly insulted, I couldn’t help the fact that I was getting hard. Brooke noticed the hardness on her butt cheeks and she smiled. Brooke mouthed to me, “Your friend?” I nodded. Brooke had me roll over onto my back and she started playing with my boy clit.Mark continued one, “So anyways, she gave me the best head I’ve ever had. She worked me on edge and kept me there for a while. I was almost ready to bust my nut in her mouth, but I had to have more from this bitch.”Great, now I’m a bitch. Brooke started shaking from holding in her laughter at the overheard crudeness of Mark. “So I asked her to stop, and I wanted to ride her fine little pussy. But that damn time of the month stopped that. I was thinking she was a cock teasing skank when she suddenly offered something else.”So now being on the receiving end of Mark’s crudeness, I fully understood why my friends always had one night stands with the women they pick up. They were all insensitive pigs. Yet for some reason, I wanted to go over to Mark’s house and ride him all over again. Damn, it was a mix of emotions that was confusing as hell.As Mark continued, Brooke slowly sank down on my pole. God, she felt so marvelous. Suddenly, Mark’s voice caught my attention. “Hey, Jesse. Are you still there?”“I’m here. I just got a little distracted.” If he only knew why. “What did you say after she offered you something else?” “O-kay. She offered me her to take her backdoor bare. I was a little surprised as only cock hungry whores offer their ass bareback right away on the first time. Normally I’d have to work at it and convince them for some ass action. But this fine piece of ass offered it up right away.”My eyes rolled back, not only from Mark’s degrading comment about me but also due in part of Brooke’s amazing ride on my own cock. A moan escaped my lips as Brooke started gyrating on me.“Jesse, is everything alright?” A quick question and evidentially Mark was not willing to wait for a response. “So I slid her panties aside and shoved my cock inside of her ass. It was such a nice tight ass, and feeling it bareback had me on edge almost immediately. She started moaning and getting very vocal about wanting me to fuck her ass harder. Suddenly she was starting to cum.”Oh god. Mark is setting me up for exposing me from my comments of wanting it in my boy pussy and make me a girl.Mark continued on, “I rammed my cock nice and deep into her, and I came inside her nice tight ass. It was so amazing dude! I have never had a woman get me so hot and bothered so quickly. God, I wish last night didn’t end.”Another moan escaped my mouth as well as an “oh god” as Brooke had me near the edge.“Jesse? What’s going on? Are you masturbating to my story?”I lied Batıkent escort bayan when I replied, “Yeah, what you’re telling me made me horny.”“So anyways, I wish I could remember her name. She was such a hot little piece of ass, I wouldn’t mind fucking her ass and shooting my load deep inside her again. Wow! Was the first thought that entered my head. Not only did I get Mark all hot and he wanted my ass again, but he genuinely had no clue that I was that girl. Suddenly I blurted out, “Oh Shit! I am cumming!”Brooke smiled as I my cock hardened inside of her and shot several spurts of semen deep inside her.Mark replied, “Shit dude! This piece of ass I had last night also made you cum! We have to go back there tonight and see if her and her friends show up again. You really need to go out with us tonight. Brian, John, and Adam also commented that they wanted a piece of her ass as well. I wonder if we met up with her again, she’d be up for an anal gangbang? Hell, I bet she’d even take mister shy guy Jesse on as well. God, we have to find her again.”I was floored. I said good-bye to Mark and hung up the phone. A look of shock had come over my face from Mark’s last comment. Not only did I fool Mark, but all my other friends wanted a piece of my ass as well.****************************************************************Once Brooke and Suzy said their good-byes to me and Tracy, Tracy turned to me and asked if we could go shopping. Since I had nothing to do, but to spend time with the love of my life, I quickly said yes. We went to the local mall as Tracy wanted to look for clothes and shoes. I quickly told her that I would meet her at the food court in an hour. As I turned to walk away, Tracy grabbed my arm and said, “Not so fast there babe. I didn’t come here just to shop by myself.” Well, it was worth the try.We first walked into a woman’s lingerie shop. While in there, Tracy was totally focused on corsets. She explained to me how the waist on the corset matches your waist size but in reality, they help shrink the size of the waist by two to three inches. Seeing that Tracy already had an awesome hourglass shape, I didn’t quite understand why she felt the need to make her waist appear smaller. After picking out a couple of sizes of two different ones, she looked at me, “Come on Jessie. Let’s go into the dressing rooms. I’ll need some help with these.”I took a look at the corsets and saw a lot of lacing that looks like it needs to be tightened. I understood why she wanted me to join her in the dressing room, but I still didn’t get her need to bring in her waist more. Tracy talked to one of the sale’s associates and pointed at me. I saw a smile on the sale associate’s face and then a nod to Tracy. Tracy came to me, grabbed my hand, and led me inside the dressing room. When I looked at what Tracy had grabbed, she had two steel boned corsets, one was a no frills white one, and the other was a sexier looking black one with some lace. I asked Tracy what I could do to help her out. With that question, she turned to me and stated, “Take off your shirt and pants.”Ok, that was an odd request. I did what she asked me. It was very awkward to be standing almost naked in a woman’s lingerie shop. Tracy ordered me to turn around and stick my arms out. I followed her instructions. Next thing I knew, Tracy had the sexy black laced corset around my body, and she quickly secured all of the clips. Astonished by what happened, I asked, “What are you doing?”“Well hun, since you liked what happened last night, we need to start making a wardrobe for you. The first thing we need to do is help feminize your body by giving it a more womanly shape. We are starting at the waist as a sexy women has a nice hourglass shape and not a manly box shape.”Then this all clicked in my head. Today’s shopping was not really for Tracy, but for me.

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