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 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 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 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.

As I was starting to reply back to Tracy, I had the wind knocked out of me as several laces were pulled. A lot of pressure was applied just above my hips. “This will feel very uncomfortable,” Tracy stated, and then paused for a couple of seconds while she tied some laces. “At least for a little while. Your insides will get used to the tension and gradually will adjust. It does get easier and more comfortable for you.” She then proceeded to tighten up the laces near my ribcage which knocked the wind out of me again.

“Holy crap! Tracy! Does it have to be this tight?” I loudly but barely got out.

“Quiet hun! Just relax. It will feel better in a little bit. Besides, making all that noise is just going to give you away.”

After she finished tying the laces, she smiled and directed me to the mirror. Even though it was tight on me, I could hardly bend my lower back, and that it was hard to breathe, I have to admit that it looked sexy as hell. I also saw what it did to my body, and then I realized that I really could have the stature of a woman. I started imagining all of the cute and sexy things I could wear if I really had this figure full time. My thoughts were interrupted when Tracy started loosening the laces and my figure started to transform into a manly figure again. Internally, I was disappointed.

Tracy saw my saddened look and replied, “Don’t look so sad hun. This one is a keeper for you. We have one more to try.”

She then released the clips and wrapped the white one around my body. She proceeded to repeat all of the steps with the white corset and once the laces were firmly in place, she smiled. “Damn you look sexy!“

I looked in the mirror again and immediately started getting hard. I couldn’t believe what a simple corset would do to a body. With this simple change in wardrobe, I felt a part of my masculinity fade away forever. And, I loved it.

Tracy once again interrupted my thoughts, “Hun, put your clothes back on.”

I gave her a quizzical look. “Come on hun. You are going to wear this while we finish shopping. “

“But… But… People are going to see me like this.”

“No one will know. Quit being such a macho man and get going.”

I slipped on my clothes and saw that with the cut of my shirt, it did look a tad bulky but nothing that would be obvious. Tracy looked for some more lingerie in the store which included hot pink frilly panties, sexy fire red bra and panty set, and several more surprises for me. Finally, we got to the lady at the counter to check out.

The lady rang up everything, and then Tracy handed her the tag for the corset I was wearing. The lady asked, “Where’s the corset?”

Tracy looked at me and smiled, “Jesse here liked it so much, that he decided he wants to wear it while we shop some more.”

The lady behind the counter turned toward me and winked, “Well, it is one of our most popular corsets and it does a wonderful job in shaping your womanly body. I hope you enjoy every moment wearing it.”

After Tracy paid for the lingerie and corsets, we walked into a woman’s shoe shop.

“May I help you Ms?”

“Yes, my friend here is looking for some sexy shoes with a minimum three-inch heel.”

The clerk looked at me with a smile. “Certainly. What size do you wear?”

I was a little stunned at what Tracy did. Nothing came out of my mouth, so the clerk replied, “Sir, what size are you?”

“Um… Ah… Size nine-point-five men’s” I blurted out.

“No dear, I need a woman’s size. I would guess a size eleven, but since it appears you don’t know, we’ll measure out your feet to verify.”

The clerk got out the Brannock Device so she could measure out my foot length properly. After prodding me to stand up, she looked down and stated, “Size eleven, medium width. You’re in luck, we have lots of choices for you.”

I walked with Tracy and the clerk around the store. Several options were immediately set aside by Tracy for one reason or another. When the clerk got to a pair of cherry red five-inch stiletto heels, Tracy instantly replied, “Those! I think he’ll love wearing those.”

“I’ll be right back.” The clerk turned and left for the back of the room.

“Tracy! Are you kidding me? There’s no way I can walk in something like those. They’ll kill me.”

“Settle down hun. Trust me, you’ll get used to them in no time, and you’ll want to wear those shoes.”

I replied, “No way will I wear those shoes. They are too… Too…”

“Sexy?” Tracy finished for me. “These shoes will be perfect for you. I want you to love wearing high heeled stilettos. They will accentuate your sexy legs, force you to push out your rear a little more, and you’ll have no choice but to walk womanly in them.”

“I don’t know.”

“Humor me and try them on. If you don’t instantly fall in love with them, we’ll find you something that you will fall in love with.”

The clerk came back with two pairs of shoes. “Let’s try these on first.”

The red stilettos. The clerk kneeled on the floor and helped me put on a pair of nylon socks so protect the shoes, and then she helped me with the right stiletto. As the shoe slid down the length of my foot, it felt different as it forced my foot into an arch that I wasn’t used to. When the clerk used the shoe horn to get the heel of my foot into the shoe, something inside of me thought these shoes feel really nice. The clerk repeated the steps with my left foot. When both stilettos were on, it felt like these shoes were meant for my feet. They felt like they were meant for me. A small smile came out for Tracy and the clerk to see.

“Jesse hun, what do you think? You love them, don’t you?”

“They’re alright.”

The clerk added, “Don’t deny it. You’re in love with them. I have seen enough women with that look when they find a shoe they love.”

“Yeah… I love them!”

“Welcome to the world of shoes, Jesse. Now that you will have your first pair, you will never look back. I guarantee you in no time you’ll have a collection of shoes for every color dress wear and situation. You’ll be addicted to shoes.” Tracy commented to me.

“Now let’s try to walk in them to make sure they fit well and they are comfortable for you.”

I stood up with some wobbly legs. I took my first step in them and almost fell over.

“Careful hun, you’re not used to the height. Take small steps, one foot in front of the other. Don’t walk like a guy.”

I took Tracy’s advice and slowly put on foot in front of the other. Several small measured steps later and I had the balance thing almost figured out. The shoes were surprisingly comfortable to me. With the small measured steps, one foot in front of the other, I could feel my hips sway. As I walked to the end of the aisle and turned around, I saw Tracy whisper something to the clerk. The clerk nodded, smiled, and whispered something back to her. When I returned to the girls, I sat down.

Tracy looked at me and asked, “Well, what do you think?”

“I.. I.. love… them.”

“I knew you would! Now try on the other pair.”

It was the same shoe only in black. I repeated the same trial with these shoes and then with a glow, I told the clerk, I want those too. We went down the next aisle, and I didn’t even wait for Tracy to suggest a shoe. I pointed to a pair of red strappy sandals with four-inch heels. The straps went above my ankle and to my lower calf. “I’d like to try those, please.”

The clerk smiled and said she’d return. Tracy in the meantime picked out five more pairs of shoes for me to try. After twenty minutes of trying on shoes, I ended up purchasing six pairs. Not a bad start for my collection. I took the bag and proudly carried it out into the mall. Yet another sliver of my masculinity disappeared, and I wouldn’t have changed it for the world.

Next, we went into the anchor department store to look for some clothing. I was really starting to get into shopping which was weird because I really hated to shop. Tracy and I spent about an hour looking through the racks and collecting a bunch of clothes for me to try. I hardly noticed that several people were staring at me, but I really didn’t care. For all they knew, I was the bag and clothes carrier for my girlfriend. After Tracy was satisfied that there was enough clothing for a couple week’s worth of dress-up, she walked into the dressing room. She came most of the way out, looked around, and saw the coast was clear. “Quick Jesse, come inside.”

I quickly entered the dressing room and into the stall. Again, Tracy asked me to take off my clothes and start trying them on. Some of them didn’t fit too well, but there were a couple that really accentuated my now womanly figure via the corset. The familiar growing of my manhood started as I saw just how sexy I would look as a woman. I couldn’t stop thinking that I was on the slope to womanhood and I’d lose my manliness. The conflict within me boiled. I so badly wanted the best of both worlds, but I knew a choice would have to be eventually made.

Tracy noticed the bulge in my shorts, so she proceeded to take them off and lightly stroke my manhood. “Looks like my girly boyfriend could use a little release.”

I nodded in agreement.

She continued, “You will have to wait. A woman sometimes needs to pleasure herself immediately, other times the torture of waiting for pleasure will greatly enhance the experience later on. Today, you’ll have to wait.”

Great, a case of blue balls is in my future.

Tracy reached into the lingerie bag and pulled out a real cute hot pink set of panties and asked me to put them on. I willingly did so and immediately felt the soft cottony fabric incase my balls and shaft. It felt so divine. I just wish this was the same for men’s clothing. After thirty minutes of trying on clothes, we agreed what would look best on me and went to the checkout.

It was obvious by the size of the dresses, blouses, and clubwear that these were not Tracy’s. The lady behind the counter asked if we found everything alright. Tracy nonchalantly told her that I found everything I needed. I blushed from the comment, and the lady gave a little smile. Tracy told me she would be by the make-up counter and left.

After ringing everything up the lady handed me the receipt and said, “Anytime you want a private shopper, please look me up. I’d be more than willing to find other sexy items for you to wear. My name is Nadia.”

I replied, “Nice to know about the service you offer, Nadia. Thank you very much for the offer.”

“Anytime. I love guys who are in touch with their femininity. Your girlfriend may want to watch out, after having a taste of me, you may never go back to her.”

I walked off all blushed. It was a little shocking that I was hit up by another female cross-dresser lover. I quickly made my way to the make-up counter and saw Tracy sitting in one of the chairs.

“Hi, Hun! I have an appointment with a cosmetologist. You’ll love what they will do for you to turn your masculine facial features to more feminine.”

“Um, I don’t know if I want to go that far yet. Can’t we do this in private? I don’t want someone knowing me walk past and see make-up being applied to me.”

“Oh, you little worry wart. Just go with the flow. I haven’t steered you wrong yet, have I? Trust me, you’ll love it.”

I sat down and shock hit my face. Suzy was the one that was going to help me with my make-up.

Suzy came over and said, “Hey sexy, looks like you really enjoyed last night. Let me teach you how to apply all the make-up that I have prepared for your purchase.”

Already prepared? What in the heck is going on? After a few moments, I replied, “I did enjoy last night, but do I really need a lesson in applying make-up here in public? “

With a bubbly voice, Suzy said, “Come on Jesse! It will be fun!”

I looked around and after not seeing anyone else around us, I sat down.

For the first several minutes of my lesson, my eyes darted around anytime I thought I saw movement. I really didn’t want anyone to see me here. Tracy saw I was distracted so she moved herself such that I couldn’t see much peripherally. Suzy was getting down to business by describing and showing me how to apply moisturizer, cover my five o’clock shadow, apply eye shadow, and all sorts of neat tricks to get the look that I want. Suzy put me at such ease, that I forgot I was in the middle of a department store having make-up applied to me. Next thing I knew, she was doing the last step and showing me how to make my cheeks more feminine looking by using some shadowing techniques. When it was all done, there was an odd sense of let down. I was really getting into what she was doing to me and showing me. I wanted her to keep pampering me and continue beautifying my face.

After I expressed my let down to Tracy and Suzy, Tracy stated, “Don’t worry hun, I have this entire make-up session on video for you. Now you can watch and repeat whenever you feel you need a refresher.”

After completing the make-up session, Tracy and I got side by side pedicures and manicures. The feeling of having someone care for your fingers and toes was something that I never experienced. It was fun being a part of the gossip of several other women while waiting for our nails to dry. I learned a lot about fashion trends and how to properly care for my hands and feet. After the manicurist painted my fingernails a hot cherry red color, she gave me a nod of approval for the color and how it matched my make-up. I actually was surprised about what I had done as I never paid a lot of attention to details. Here I am now, paying attention to matching colors, to women’s shoe styles, and how they use various accessories to help complete their image. Being a woman was totally different. I determined right then and there that I would love to do this full-time.

After the mall, Tracy and I headed back to her house. On the way home, my phone rang. I answered it to hear the voice of Adam.

“Hey, Jesse! We need you to come join us tonight! There was a hot sexy woman and a group of her friends at the nightclub last night that we were hoping to see if we can meet up with them.”

Tracy overheard the conversation and mouthed to me “Tell them you can’t make it.”

I replied, “Sorry Adam, I can’t make it tonight.”

“Come on Jesse! This woman was so hot, I think she would even want to do a shy guy just like you. Live a little bit!”

“Sorry Adam, I can’t tonight. Even if I could, I’d have to be dressed up as a woman because of the bet I lost.”

There was a moment of silence, then Adam said, “Oh yeah. I forgot about that. I don’t think she’d dig a man in drag. Well, maybe next time. Later!”

I hung up the phone.

Tracy looked at me and said, “Good job hun. You had to do that.”

“I don’t get it, why did I have to do that?”

“Because, the male Jesse is no more, for the time being, it is womanly Jessie that needs to go.”