A few days had passed since I sucked cock and took it into my ass for the first time. Greg, my coworker and good friend, had easily seduced me into worshiping his big cock and plum-sized balls with both my mouth and my ass. I considered myself extremely lucky because my first gay experience was with a well-endowed man in every aspect. Just the thought of his big, thick tool throbbing and shooting a strong load of cum made me INCREDIBLY horny.
Just as a review, I was 22 at the time and I had been blessed with a thick bubble butt on my thin and athletic frame. It has attracted attention from both guys and girls my entire life and my experience with Greg made me realize that my butt was made to be fucked. It helped that I had a very thin waistline with virtually no fat on my stomach and sides. On top of having a healthy girl's ass, my first cock sucking experience also taught me that my gag reflex was almost non-existent and I was able to take cock into my throat without much trouble at all. I had a dirty, almost unhealthy, obsession with big, fat balls as well.
When I was leaving Greg's house a few days prior, I had made a comment that I would love to dress up like a girl for him since I had indeed become his little bitch. Although I hadn't talked to Greg for a few days, I wondered if the day would come that I could live out this fantasy. I spent the next few days on Literotica searching for and reading stories about submissive cross-dressers. Reading stories about guys taking time to "do themselves up" to look like a girl for their perverted partner(s) continued to fuel my sexual curiosity. Not only was I turned on by the thought of wearing sexy female clothes for Greg, but I imagined myself doing everything I could to make myself into a sexy girl. This included using full make-up, a wig, and painting my nails among other things. If this fantasy was going to play out, I wanted Greg to believe 100% that I was a girl.
Google is a wonderful tool for many reasons. I spent the next day or 2 doing research on how to best cross-dress and appear as a woman. I learned how to apply make-up and fake nails, how to choose the best clothes to accentuate my thin frame and thick ass, and how to strut like a sexy girl. I took time to get accurate measurements of my entire body to determine the size of clothes I would need because my plan was to order everything online in order to avoid odd glances at the mall.
I ordered my make-up which included fake lashes, mascara, blush, eyeliner, eye shadow, and a tube of cherry red lipstick. I then hunted down a fake nail kit and red nail polish. After the make-up and nails were in order, I proceeded to find a sexy, rather expensive blonde wig that was promised to not come off my head too easily. I found a sexy, heavily padded pink bra that would make it appear that I had relatively large breasts and a sexy pair of pink, low-riding "boy shorts" from Victoria's Secret online that would hug my butt snug and match the bra. I always loved the way those "boy shorts" made girls' butts look so good. It took awhile to find the clothes I wanted, but I found a short, tight-fitting white skirt that was sure to cup my big bubble butt and show off my long legs. I then came across a pair of black high heels that would be perfect to tone my legs and accentuate my feminine butt even further. I would just have to train myself to walk in them! The shirt I chose was a simple, black woman's t-shirt to match the heels. I learned that wearing darker tops would draw attention from my upper body and focus it more on my hips and ass.
It took about 5-6 days for all of my clothes and accessories to arrive at my house. During this period of waiting, I took 2 showers a day and really scrubbed my entire body vigorously in order to not have any blemishes and I took care to use expensive lotion on my body(especially my ass and legs) in order to get the very soft, feminine skin that I desired. When everything finally arrived, I decided to go through the process of trying everything on for a "test run."
I got into the shower that day, cleaned myself well, and took the time to fully shave my entire body smooth. When I got out, I turned my ass to the mirror and involuntarily said "wow!" under my breath as I looked at my smooth, hairless butt. This was going to be so much fun!! I started by applying my fake eyelashes as well as all of my make-up, making sure to take my time and do it right. I then applied the blonde wig securely. What I saw in the mirror was a young, feminine girl's face staring back at me and I couldn't help but grin. It was at this point that I decided I wanted Greg to have an idea of what was in store for him, so I took a picture of myself from the neck up with a slutty, sly grin on my face. I didn't want to send him any full body pictures with myself dressed up because I wanted to make him wonder and keep it a surprise. About 5 minutes after sending the picture, I received a text message reply from Greg. Upon opening it, a large picture of his thick, erect cock and fat, shaved balls popped into view with text under it reading "Wow! Such a sexy little girl! I need that pretty little mouth on my balls!" I instantly became hard and just stared at the picture while licking my cherry red lips.
A few more minutes passed and I received another text from Greg. It read "Send me a shot of your body so I can stroke while I think of you." I didn't want him to stroke it though. As I said, I wanted to surprise him and leave him wondering, but I also wanted him to hold off masturbating over the next few days so he could build up a big, juicy load to share with me.
"Be patient Greg," I replied. "And you have to promise me you won't jerk off and waste that cum. I plan on coming over in a few days and I need you to have a nice, thick load built up for me." I was so horny that I was shaking.
"FINE. If you promise to come over this Saturday around noon, I'll try my best to hold off cutie. I have a little surprise for you as well.." he shot back. Surprise? What surprise? I was curious and excited. What could he mean? I decided to play it cool and not pry with questions. After all, Saturday was only 3 days away and I loved surprises.
"Deal! :)" I replied.
After the text convo ended, I resumed my little game of "dress-up." I wasn't totally sure if the clothes would fit right, but I was hoping that the time I put into research would pay off and everything would work out. I first slid the pink panties and bra on and looked in the mirror. Perfect fit! The padded bra made me look like I had perky tits and upon turning around, I noted that the boy shorts fit nice and snug and my plump butt cheeks poked out of the bottom a little. Next was the white mini skirt and black shirt. The shirt fit perfectly, but the skirt took a minute or 2 to get into. When I was finally done, I looked into the full-length mirror and my jaw dropped. The skirt couldn't have fit any more perfect and it hugged my hips. The shirt showed off a little of my thin waist (as intended). I turned so my butt was towards the mirror and my jaw dropped even more. The white skirt cupped around my cheeks PERFECTLY. Next, I fit my feet into the black high heels. They were a little snug, but not too small. I didn't have much trouble standing up in them, but I knew I would have to put some time into getting used to walking in them. Standing in the heels made my calves look well defined and made my butt look even better than it already did. I was so damn excited that I wanted to scream! Everything fit perfectly! The final step would be applying and painting the fake nails, but I decided to wait until Saturday to do that.
The next few days went by slowly. I spent some time learning to walk in the heels so that I was comfortable in them. Although I started the summer off working with Greg, we were laid off at this point in time. My uncle didn't have a job lined up for us and he was preparing for a lucrative construction job with a multi-millionare who wanted to build a mansion. This meant that I could do nothing but wait around the next week or so until work picked back up. I didn't really mind, though, because I had some money in the bank.