Here I am in the bathroom buck-naked and hairless. An amazing thing happened in the tub of my best friend's bathroom. My secret love and best friend Tracy, just had an amazing love making session. We were starting to get hot for each other after I dried off when the door bell rang, and her beautiful naked self ran out of the bathroom to answer the door. I started reflecting on what just happened. Mister shy guy, loses a bet, has to dress up as a woman as payment, and just had amazing sex with his secret love interest. It was definitely turning out to be an interesting day.
I started hearing different women’s voices approaching the bathroom as I came out of my day dream. Tracy walked in with two of her friends, and I turned toward them, totally forgetting that I was still naked.
Tracy’s redhead friend said, “Oh wow, Tracy! What a catch you have there!” as she was staring at my manhood. “By the way, my name is Susan, you can call me Suzy.”
I reached out and shook her hand.
The brunette friend smiled at me, “And he looks so excited to see us! I’m Brooke.”
“Nice to meet you, Suzy and Brooke.”
Tracy interrupted, “Okay girls, you’ve got plenty of time to be with Jesse. No need to get him all riled up so quickly.”
I was wondering what my love was implying. I let it go thinking she was just participating in the bantering.
“Let’s get Jesse all ready to payback his bet,” Tracy continued.
Tracy escorted the girls to her room and had them set-up their make-up and clothes in preparation of changing my appearance. Tracy came back to the bathroom and did a final look at my body. Any hair that was left after my original shave was now totally gone. I looked at myself in the mirror and saw a hairless body that had some form of a woman. I was never a sporty person, so none of my muscles were well defined. My stomach was flat but not six packed, and it was the first time that I realized my waist did come in more than a typical male. I actually had a slight hourglass figure. I was a little taken aback by what I truly saw. Tracy finished her touch-ups and told me it is time to have Suzy and Brooke help me out.
I walked into the room to two women giving each other some soft kisses. They turned and looked at me, one with a measuring tape. Suzy quickly measured my waist, hips, chest, and inseam. Finally she went to her car and returned with several articles of clothing. I started trying on several skirt and blouse combinations. I got to one that was a low cut red blouse that would show lots of cleavage, and a black leather mini skirt that just barely covered my butt cheeks.
Finally, Brooke said, “That is the one for you. Now we need to start accessorizing you.”
They took off the skirt and blouse and started working on my body. Suzy took out a pair of silicon breast forms that looked to be C cup worthy. She applied glue to them and carefully stuck them on my chest. Next came a matching bra and panty set. The bra was the same color red as the blouse and had some frills around the edge. I was handed a pair of red panties that had garters attached to them. As I was putting on the bras and panties, I was starting to become hard. Suzy had me sit down, and she painted my toenails a nice cherry red color. My manhood was hard as steal. As my toenails were drying, Suzy mentioned to Tracy and Brooke about my hardness.
“Well, well, it looks like Jesse is getting turned on dressing up in sexy women’s lingerie. We can’t have a girl sporting wood. Suzy, go ahead and take care of his cock,” Tracy stated.
I was flabbergasted. My love, and the one who said she loved me is willing for me to have sex with her friend? I was in a state of shock. I asked Tracy if she were certain about this. She told me that today and tonight is about me, and I should have a free pass and enjoy myself.
Tracy finally said, “After tonight, you are all mine Jesse.”
Suzy wrapped her fingers around my cock and started stroking it. She coaxed a drop of pre-cum out of the head and she quickly took her tongue and licked it off. Next she wrapped her lips around the head, and slowly but sensually took my cock deeper into her mouth. She rhythmically took my cock in and out of her mouth, occasionally pausing to lick my taint all the way up to the helmet and then starting the process all over again.
Tracy and Brooke watched the whole thing while they were kissing passionately and starting to rub each other’s pussy through their panties. Suzy stopped giving me head, and I had a look of disappointment as I was really enjoying what she was doing to me. My disappointment however didn’t last long. Suzy lifted up her skirt, moved her thong aside to expose her flowering pussy lips and straddled my waist. As she started lowering herself, she grabbed my cock and stroked it to fill hardness. Pre-cum was oozing out, and I was anxiously waiting for relief. Finally, she lowered herself so my cock head touched her pussy walls. She slowly rocked up and down. Each downward motion sucked my cock deeper and deeper into the depths of her womb. She started a grinding motion as she rocked up and down on me. After ten minutes of grinding, Suzy started to shudder. She was starting her orgasm. I could feel her pussy muscles clamp down on my manhood and I suddenly shouted out, “I’m going to cum!”
Suzy kissed me and whispered in my ear, “I want you to cum inside me.”
She bounced up and down a couple of more times and then I started my release. My cock twitched and a single spurt came out into her womb. Then another contraction followed by more sperm entering her. I shot five times inside of her which surprised me because I don’t usually recharge that quick. She got off of me and some of my cum started to drip out of her pussy and onto her thigh. Suzy casually scooped it up and licked her finger clean of our juices. She then gave me a passionate kiss and shared our coupling juices with each other.
Tracy and Brooke kept finger fucking each other while Suzy continued to prepare me for tonight. She made me wear a corset. As she was tightening it, it felt oddly uncomfortable yet comfortable at the same time.
It definitely made my posture straighten out as with the steel boning, there was little to no flexibility for my waist. Now that my toenails were dry, Suzy carefully put my foot into a black thigh high panty hose and lifted it up my leg until it rested mid thigh. Suzy then connected the garters to the pantyhose. Suzy repeated the procedure with my other leg. I then put the red silky blouse back on as well as the mini black skirt.
By this time Tracy and Brooke finished their petting session and directed me to a swivel chair. Brooke told me that it is time to finish getting ready. She found a sexy brunette wig with curls. Brooke placed the wig over my short hair and started shaping it so it looked natural and sexy. After ten minutes of primping the wig, she felt it was time to do the make-up. As Brooke started applying foundation onto my cheeks, Suzy started working on my fingers. Fake nails were glued onto my existing nails. They were shaped and then painted the same sexy red color as my toenails.
After the foundation was applied and softened, Brooke added blush and finished off my cheeks and chin. Next she plucked my eyebrows to a more womanly shape, and then applied mascara and eye shadow. After my eyes were all complete, Brooke took a device and placed it on my ear lobe. I felt a sudden pain as my ear was pierced. She repeated it to the other ear, and placed a small pair of dangling earrings in my newly pierced ears. The last thing she did was add a sexy necklace and bracelet to my accessories.
Suzy gave me a pair of 4” sexy red strappy heels to put on. As I inserted my foot into the shoe, I started to become hard again. I got both shoes on and was told to stand up. As I stood, I pulled down my skirt as much as I could. It only served to expose the fact that I was hard yet again.
Tracy said, “For Pete’s sake, girls don’t have hard things poking out of their skirt! Brook, what will you do about the problem you caused?”
Brook came up to me and whispered in my ear, “I love it when men play dress up. It makes me all wet inside.”
Brook started stroking my penis through my panties and continued to whisper, “I want you to eat this fine little piece of pie until it shakes your world, and then conquer it with this nice hot piece of meat. Now take off my clothes and be a good little sissy girl.”
I complied with her request by proceeding to take off Brook’s pants. Next to come off was her thong. She asked me to lick her flower and get her good and wet. I truly could not believe that all of this was happening. The events unfolding at Tracy’s house was more like the events that my friends would experience, not me. I gently spread Brooke’s thighs and slowly moved my hand to her vaginal region. I spread the lips and slowly breathed on her. She was calling me a tease, but I could tell deep down that she liked what I was doing. I finally placed the tip of my tongue at the bottom of her slit, and worked my way up to the front. I reached her clitoris and did a gentle swirling motion. She was starting to get wet, very wet. I continued a teasing, slow, and sensual eating of her pussy. Brooke suddenly grabbed my head and pushed her pussy against my mouth. “Eat me to orgasm! I want to squirt all over you!” I complied with Brook’s wishes.
I finally got Brooke to her climax and she started bucking into my face uncontrollably. She was moaning like crazy, and finally made her orgasmic noises as my tongue continued to lick her clitoris. “Alright big boy! It is time for me to cum all over your face!” With that, she squirted in orgasmic heaven. Streams of her juices were spraying on my face and in my mouth. I couldn’t believe how much she squirted. After she settled down, she asked me to fuck her silly.
What I learned about Brooke is that she was a dirty girl that didn’t want a slow and sensual fuck. She wanted me to play a little rough with her and slam my manhood into her womb over and over. We spent ten to fifteen minutes fucking hard and varied positions. She then said, “I want you to pound my ass hard and shoot your load into my backside.” I rolled her onto her hands and knees and quickly penetrated her anal ring. She yelped in surprise and a little pain be being taken so hard. Brooke quickly got used to the pounding and started pushing her ass hard into my thrusts to deepen the penetration as deeply as possible. Finally, I couldn’t take it anymore and I shot three times into her ass. It was apparent that I was starting to run out of juice.
When we were done, Brooke realized she needed to fix some of my make-up as it smeared when I pleasured her pussy with my tongue. I finally got the last of my make-up fixed, and Brooke asked Tracy and Suzy to look at me.
“Oh my god Jesse, you are absolutely stunning!” Tracy squealed in delight.
“If I didn’t know any better, you are the hottest girl I’ve ever seen,” Suzy replied.
I finally looked at myself in the mirror. I couldn’t believe it. The reflection in the mirror was not of my own. It was the reflection of a hot woman, wearing a sexy red blouse, with a nice set of breasts, and a hot hourglass figure. I admired that reflection in the mirror. Suddenly, I had this odd thought pop in my head. I wished I could be her, not just now, but forever. As I was having that thought, I sported wood again through my skirt.
“Jeeze Jesse, stop with the hard-ons. You are a girl now.” Tracy sneered.
All three of the girls took turns sucking me off until I finally came in Brooke’s mouth. She promptly shared my small load with Tracy and Suzy with passionate kisses.
For the rest of the afternoon, they taught me female mannerisms, how to walk in heels, and how to talk womanly. It was pretty easy to falsetto my voice as it wasn’t too deep to start with. I also tried to sport wood, but it was no use. I was spent. It was approaching 9:30 PM, so Tracy said, “Time to show off our new girl friend at the night club.”
With that, we headed out the door to go eat and meet my friends to pay off the debt. I secretly felt super womanly and a little jealous that I was not a real woman. It has been an interesting day.
