It started with an internet conversation. SgrdE8 was new to the chat rooms I had been on recently. My fascination with cross dressing and deviant homosexual behavior was completely in my head and online to that point. I'd never expressed it with anyone in real life, and certainly never done any thing about it. Many people I'd talked to were in the same boat, and I often wondered how many people I'd pass in a day that were like us. This guy was named Greg and he was very cool. He wasn't an arrogant cock like many, nor was he belittling about the fact that I never had the guts to try anything like many "out of the closet"-types were. I'd told him I'd flirted with a few guys and almost brought myself to do something once, but the situation just wasn't right. He asked me what the right situation was and I said I didn't know. After talking over the course of several weeks, I decided I was going to try to actually meet him. No pressure, he assured me. He knew all about me and was eager to meet me, without reservation or judgment.
We met over lunch (he bought) and I was very relieved. We had a pleasant conversation that didn't include anything about my fantasy life. Just sports, politics, like any of my regular guy friends. Later we talked online again and he invited me over for the weekend. Again, no pressure. After a few weeks of busy schedules, a weekend opened up. I was nervous as hell, but it was a great feeling. I felt excited and scared, horny and cautious. I felt alive, like I hadn't felt before in my life.
When I arrived at his house, I couldn't hold my hand still to knock. I paced around the front yard of his beautiful secluded home. It was gorgeous. He'd made a lot of money and bought a nice home with lots of land. It was well lit, and I kept asking myself what am I doing here? Thinking he was probably watching me out the window or through a security camera. Finally, I knocked. After a long, long two minutes, he opened the door and greeted me with a handshake. Very simple, no pressure. It was very comfortable. He welcomed me in and I toured the house. We talked sports and watched part of a game on his giant TV. He asked if I'd mind if I had his assistant fix us something for dinner. He didn't want me to get nervous with another person, but I was very comfortable and didn't have a problem with someone else. Afterall, we were just two friends hanging out, nothing out of the ordinary.
After dinner, we had more of the same. He never once even brought up what we'd talked about, and I was too nervous to do it myself. We got very very drunk. The more we drank, the more it slipped into conversation, but still, mostly in a joking way. He told me tomorrow, we could have all day to escape to fantasy, but only if I was very comfortable. I ended up very drunk and about to pass out when he convinced me to go to his bedroom. At that stage, I was fine, although I was not where near a position to do anything. He wasn't either, and very soon, we were both asleep, although in the same bed.
When I awoke the next morning I was in a good mood. I had no ill effects of the alcohol the night before. I was ready and committed to following through. I turned over to see Greg, but he wasn't there. Instead there was a note: So sorry, I had to run into work this morning. Make yourself at home. If you are ready, my assistant Claudia would be ready to assist you in your transformation.
Hmm, now I was having second thoughts. But in a way, I was more excited about doing this. I wanted to get myself ready for "my man" and surprise him when he got home. I found Claudia, and told her I was ready. She smiled and told me to follow her. She was a fair-complected girl in her 30's she didn't wear much makeup and seemed to have simple tastes in clothes and no jewelry. She wore glasses and had light auburn hair.
"Greg told me about what you wanted, and I'm here to help you with everything." she said. "I understand you are very nervous, and I want you to be comfortable. Please let me know if there is anything I can do to help you." She smiled. She was very non-threatening and I found ease with her. We chatted a little about clothes and fabrics and I was ready to begin. I realized that Claudia was going to be my fairy godmother.
First step was a very hot bath and removal of all my body hair. I soaked in the hot bath for bath for over an hour. My muscles were completely relaxed and baths have always made me horny. Claudia assisted me with removing my hair. She showed me how to shave my legs and arm pits. She shaved my ass and crotch area - I didn't trust myself. I was quite embarrassed (for some reason) to have a huge erection while she was shaving me. Maybe it was the bath; maybe it was the fact that another person was seeing me naked and touching me or maybe it was the excitement of what was to come with Greg. I was so giddy and nervous just thinking about. Regardless, I had a huge boner and Claudia was having a hard time shaving my pubes.
"We need to do something about that." She said. I figured she's want me to masturbate - which would take less than 10 seconds as turned on as I was. Instead she, without warning lowered her lips to my dick. her hands rubbed the shaving cream into my legs and she fingered my ass. It didn't take long, she was very good at giving blow jobs and I was very horny. I blew a load into her mouth and she licked every bit of it.
It took me longer to figure out what just happened than for it to happen. Getting over the feeling of an orgasm, being completely naked and hairless and in a strange place, I was a little discombobulated. Claudia gently spoke. "That was quick."
"You're good." I replied. "It wasn't my first time," she said with a sly grin. "but please, don't expect that again." She said. It was for convenience-sake. She smiled as she said that, as if to say she enjoyed it and was glad to do it, she just didn't want me thinking she was a whore, which was understandable.
"Now it's time to do something about your skin.," she said when I was ready to move on. She used the softest towel I'd ever felt to dry me off and put me in a girlish pink robe. It was very comfortable. She led me to a room with a message chair in the middle. She instructed me to lay down and remove my robe. It was a warm room, and I was very comfortable not being covered. Claudia gently applied some skin cream on every inch of my body. She applied some special cream to my breast and squeezed and pulled them a lot. She told me to relax and let it soak in. She then gave me a mud mask for my face and put cucumbers on my eyes. Some sort of goop was applied in my hair, which felt good because I've always enjoyed people playing with my hair. She told me she'd be back in a half hour and for me to rest and relax. She turned on some relaxing synthesizer music and left. I was alone with my thoughts which were quite peaceful and horny. I thought about what was to come and got excited. A slight hard on returned. I was also very very comfortable. It wasn't long before I dozed.
When I awoke Claudia was removing the skin cream with a towel - all by my breasts, face and hair. I turned over in the chair and faced the floor, still with my face covered in mud, so I didn't open my eyes. Claudia applied the cream to my entire backside and left as before. I was quickly asleep this time. When she came back she told me she had to remove the cream with the towel. Then she was going to do my nails, then give me a full body message. I was going to shower off, then my body would be ready. I was so thrilled with this plan. She removed the cream from my back side. I was getting really turned on as she worked all around my anus and rubbed my ass. Once the cream was removed, she did my nails. The smell was awful and broke my moments of beautiful comfort. When I said something about it, she lit a candle which was a beautiful flowery fragrance and it mostly covered the smell. I was still facing the ground when she finished my nails. My hands and feet were dangling as they dried. While I waited, Claudia found some body oil that warmed to the touch. She rubbed it in and gave me a thorough message. I was in heaven, I love messages. She rubbed every muscle on my back side. I was still horny from the ass-rubbing and thoughts about what was to come. Now, she messaged and rubbed oil on my ass, I had to adjust my position as I was now laying on a full-fledged hard-on. She continued the message and I continued to be turned on and very relaxed. She told me to turn over. She re-applied cucumbers to my eyes. I heard sounds of the chair and she told me to lift my legs. She moved out some sort of stirrups and my legs were now in the air. My ass and dick were now quite exposed and my hard-on was still hard. She told me she was going to give me an enema, then wash out and relax my ass.
It was a little painful, but very stimulating to have my ass cleaned. I never felt so clean down there before. Then, she applied something that felt like Ben Gay, without the smell. She told me it was to eliminate any pain, if ever I need to have something inserted in there. I smiled and my still-hard dick moved in anticipation of the thought. When she was done, it felt like girls must feel after getting fingered. I was so turned on.
She started messaging my feet and worked up my legs. She briefly stopped. Once again the message started, this time with my hips. It was more firm now. It was still relaxing, but it felt... different. I could feel the fabric of pants against my crotch. I gently, subconsciously grinded a little imagining it was Greg. Slowly the message reached up my torso. In my mind I was getting messaged by my lover who was about to fuck me. As the hands reached my breasts, they grabbed and twisted and groped, more than messaged.
"What do you want?" Claudia asked, seemingly from far away.
"I wish Greg were here right now.," responded
"Why?"
"I am sooo turned on right now. I can see him and feel him fucking my ass. It feels so good."
"So if he was here right now what would you do?" I imagined her sly smile since I still had the cucumbers on my eyes.
"I would beg him to fuck me." I exclaimed.
"really?" - A man's voice- Greg's voice.
"Yes! I said loudly. Yes!. Oh my God! Greg.. please fuck me!"
"Are you sure about that? he asked, hands on my breasts. I could feel his crotch getting hard through the fabric of his pants which were now grinding into my exposed crotch.
"Please! Greg, fuck me! I want you so bad. Please fuck me!" I yelled.
"as you wish." he said.
I heard the unbuttoning and unzipping of pants. I didn't realize it, but quickly, lubricant was being applied to his now-hard dick. He rubbed his dick all around my ass hole. I moved my ass, trying to find his dick. Finally, cock and hole met. He slowly, firmly put his dick inside me. I was ecstatic. It felt wonderful. I was being fucked like a woman for the first time. It was soo fulfilling. I was about to come right there. Gradually he pulled out and slowly went back in. He was very slow and methodical, going in, out, in, out. The more he pumped, the more comfortable I got, the hornier I got. I moved my pelvis in time with his thrusts which got deeper and stronger each time. It felt so good, unlike ANYTHIHNG I ever imagined. He was going faster now, pounding my ass. He paused for just a second before a final strong push and came inside me. I was so turned on, I came immediately. My eyes, not able to see because of the mask and cucumbers, were just about glued shut from being squeezed so tightly. I was in a new phase of post-orgasm that I had never approached before. I flailed my arms a little bit as he withdrew.
"I take you enjoyed that." He said.
"That was amazing " I moaned.
"Just wait until tonight he said as he bent down and kissed my lips. I shuddered as my skin now felt a little breeze. I realized once again my nakedness, lying there, freshly fucked for the first time, recovering from the most amazing orgasm, still on the cusps of making my fantasy fulfilled. Suddenly, I felt something light cover my skin.
"Here's a thousand dollars." My lover said coldly throwing apparently large bills on me. "Go buy yourself some nice things." and with that he was gone. I could feel the slivers of money on me. In a way, I felt like a whore, I thought. This brought a smile to my lips because I was his whore. Another shudder ran through me as I thought about being Greg's personal whore. Then I thought about all the wonderful clothes I wanted to buy.
It didn't take me long to figure out what I wanted. I tried on lots of things and bought more. Every piece was sexier than the next. All of the best fabrics =- silk, rayon and others I had never heard of. I bought a lot of lack, especially lingerie. And some white, as well. I wasn't sure what he had in mind for the night, so I bought sexy, slutty and sophisticated. Also a few leather pieces, because I got hard just looking at them.
I was very excited to get back to his house and try everything on. I ripped the tags off and decided what I wanted to wear for my man when he came home. I decided on a simple black mini skirt with matching black "fuck-me" boots. and a pink silk cami. I felt very sexy wearing it, as I stood in the mirror admiring Claudia's handy work. I looked like a very hot chick.
When I heard his car pull up, my heart actually fluttered. I was so excited, it was hard to try to contain myself. I opened the door for him and he rewarded me with a very sensual kiss. We kissed for about ten minutes. Just kissed at first. When we finally broke, he told me "you look amazing." I just kissed him in response. He grabbed and squeezed my ass . It felt so good having his strong hands on my ass which was basically exposed. I ran my hands all over his back as he kissed my neck. His hands found my breast forms and he played with them as if they were real. I could tell it was turning him on. I could see him getting hard in his very expensive pants. I rubbed my hands over him and felt his dick. It was very strong and just begging to be released. I obliged and slowly removed his belt, unbuttoned his pants. They fell to his feet. He kissed my mouth again, forcing his tongue down my throat. He ran his hands through my hair and seemed to be lightly pushing me down. I was excited to oblige. In moments I was facing his rock-hard dick. It was the first one I had ever seen. I remembered it being inside me earlier and that just made me even harder, myself. I gently placed my lips on his dick. I kissed it all over. Then I licked his head and under side. I heard him moan in pleasure. he moved his hand back to my head and brought me closer. I took the hint and put his whole cock in my mouth. It was a wonderful feeling. I was so hard and excited thinking about his impending orgasm. I performed as I would liked to get serviced. It was very sensual to actually be in control. As he was getting close he grabbed the back of my head and forced me to deep throat him. I was happy to oblige. The precum was amazing. It tasted like my own sperm I had several times tried. Finally, he came in my mouth, still forcing me to suck by keeping my head in place with his hand. I let his hot, sticky load ooze down the back of my tongue. I licked him clean and swallowed his gift. I had soaked my own panties. It was an amazing and very pleasurable experience.
He stepped out of his pants and pulled his socks off. I slowly unbuttoned his shirt. He removed his own undershirt and was now naked before me. In one motion, he picked me up and brought me to his room as if I was his bride. I was so euphoric, I was in another state. He gently laid me down in the bed. He started kissing me, very softly, on the lips. He moved to my ear which made me wild. He used the weight of his body to hold mine down as he drove me crazy with his kisses on my neck and ear. He moved down, with his hands touching my skin, under my pink cami.It was an amazing feeling. his lips followed his hands down my torso, and then around my belly button. I was a bit ticklish, but didn't feel much like laughing. No, I was in another zone. He kissed up and down my legs before moving to my hard cock springing from underneath my skirt. He played with my dick briefly. He then stopped momentarily to apply some lubricant to his hands. while facing my dick, his hands explored my ass. He was pulling and prodding. When two fingers simultaneously entered my ass, his lips were on my dick. He sucked and worked my ass. It was a continuation of the amazing experiences. He let go of my dick, and just worked on fingering my ass. He found my spot and drove into me. Soon my back was arching and I was blinded by orgasm.
He moved back up to kiss my lips and I tasted my own cum in his mouth. My hands found his dick, and it was already lubed and ready. I grabbed him by the shoulders and turned him on his back. Slowly I sat down on his dick. I was getting addicted to having him inside my ass. It felt so good, I wanted to ride him all night. I bounced up and down with words and sounds flying out of my mouth from deep within. I wanted him deep inside me. I slammed my ass down on his pelvis. His hands were on my breasts before grabbing my waste. He timed it to pump into me as I slammed down on him. We were in rhythm. I could tell he lasted longer with me on top. That was wonderful because it allowed me to prolong the sensation. I was on the verge of orgasm, myself for about 20 minutes. It was such an amazing ride. He grabbed my waste and squeezed really hard as he ejaculated inside me. He was bucking wildly and I was just trying to stay on. Cum came out of my dick inside my skirt. I collapsed beside him. He squeezed me and I could feel his semi-hard dick against my bare ass. It was a wonderful sensation to drift off to.