“My name is Roger. I am a 29 years old, white, a little skinny , and a married (secret) crossdresser. I really love wearing women’s clothes and I am crazy about pantyhose (and tights. I love the total coverage and the sensation that pantyhose gives me.
One afternoon my friend, Bob called me and asked to house-sit while he went on vacation. The house was empty, save for a table and four very comfy chairs. It had been renovated and listed for sale, so it was all new, but empty. He asked if I could keep an eye on things, take calls from realtors if they called, and go make sure everything was okay.
He gave me a key, and said I could do whatever I wanted while he was gone. I could ‘hang out’ or whatever. He knew I was studying for a certification, and mentioned it would be a nice, quiet place to get away. Immediately I formed a plan, seeing this as a golden opportunity unlike any other I’ve had in a very long time. I already knew what I wanted to wear, and I couldn’t wait until late at night when I could leave home, go to this empty house, change into my female persona, and enjoy some ‘me’ time.
I love dressing completely from head to toe and always put on a wig, makeup, nails and the clothes when I dress up. It’s an exhilarating feeling. I had just bought some purple patterned pantyhose on clearance as well as a beautiful pink bustier with black lace. I would wear that under a shiny black 3/4 sleeve top, and a very tight, sexy, ribbed black tube skirt. I would of course finish off the ensemble with bright red nails to match the hooker-red lipstick I would apply, and a pair of patent black Mary Jane’s with a 4″ heel. I was already hard just thinking about it.
I got everything together, making sure I had what I needed, including a spare pair of hose (always have a spare, I hate runs), my makeup, lube, and the rest of the outfit that I couldn’t easily wear under my man clothes. With that all done, all I had to do was wait…for two more days! That’s like two MONTHS for my level of excitement and anticipation. I wasn’t simply planning on dressing up and prancing around an empty house at night…I wasn’t planning on being the only one to enjoy what I would be wearing!
With plenty of time to plan and wait, I crafted an ad online. I had always fantasized to spend some time with other crossdresser. Having a place to host, in this case the empty house, while not glamorous, gives me a much better chance than I would otherwise have had. So as you might imagine, I got quite a few more replies than usual…of course, that means nothing if they’re all flakes who just want dirty talk and pictures to get them off.
I eliminated most of the replies and narrowed it down to two that seemed promising. One of the ‘finalists’ was only available that night, which was not possible, so now I was down to one. I was hoping this would pan out. I’d hate to miss out on this opportunity. I only had a few days. So this last prospect sounded really serious. He just needed 20 minutes notice to get there, and promised he would show up. Believe it when I see it, but nonetheless, I was pumped, excited, nervous, scared… all the normal emotions I always feel when arranging a meet up with a complete stranger.
My biggest fantasy is to find a regular who lives alone and lives really close to me, like walking distance, where I could keep a closet full of clothes and shoes at his place, and a drawer full of makeup in the bathroom. I guess I’m looking for a ‘double life.’ So far, this is still just a fantasy. Back to reality…
We agreed on a time, and he wanted me waiting inside the house, where he would come fully dressed up as well. We would simply both enjoy the moment as pretty women. The next two days dragged on and on…
The day had finally arrived. I had been imagining to the scene in my head for the last 48 hours, and finally the day, or more accurately, the night, was finally here. At about 8 pm I put everything I needed.. my makeup, wig, fake tits, shoes, dresses etc. in my gym bag. I told my wife I was going to a get together with school friends. I threw the bag in my car and drove the short distance to the empty house. Letting myself in with the key my friend had given me, I locked the door behind me and went upstairs to the bathroom.
In the bathroom I removed my outer clothes, put on the bra and panty, my fake breast form and applied my makeup. I felt really sexy and hot while I was feminizing myself fully from head to toe. After my foundation, bronzer and blush, I applied my eye shadow, eye liner, and hooker red lipstick. Then I put on the red dress and black pantyhose that I just brought recently.
I then put on my wig, clipped on a pair of dangly earrings, and slipped into my Mary Jane heels, my legs looking hot as they maneuvered into the shoes. Looking at myself in the mirror, I was exploding with feminine sensation throughout my body. I would so love to go out like this any time I wanted, day, night, to a mall, Wal-Mart, around town…but obviously, that’s not a reality.
Then, I get a text from him. He asked if I was there. I told him I was, I was ready too. He said he was leaving his house now, which would put him about a half hour later than what we had set up, already being ten minutes late. I have hours, so it’s not a huge deal, but I hate waiting around for someone. Then of course I start to think he’s just playing games, it’s happened before…I’d be all ready, fully done up, guy said he was on his way, never hear from him again. Some people just like playing games.
My phone was almost dead, so I hoped it lasts long enough to continue communicating with him, that is if he’s really coming. About 20 minutes later he texts me again…he’s pulling in the long driveway. He finally arrived at the doorstep, I went to greet him, a bit nervous but excited at the same time. He seemed to be excited and a bit nervous to see me as well. He was looking hot in a beautiful red flouncing dress with nice heels. He was slim and looked quite feminine indeed. I was happy with what I was seeing.
“Hi, you look lovely. Thanks for having me.” He said.
“You look great too and it’s a pleasure.” I replied.
We go inside and sit on the chair. We start our conversation by telling each other a bit about ourselves. He tells me her feminine name is Samantha and he has been cross-dressing for the past 10 years. It was really exciting to have another crossdresser to talk with. I was really enjoying the moment and I had a lot in my mind about what to do next. But then, all of sudden, he comes really close to me and kiss my lips.
I get shocked not knowing what to do but it felt good. I wanted to stop him but he was just too good to resist. I did fantasize about making out with another crossdresser but that was just a thought. Now, it was happening right before my eyes.
He then slides his hands inside my dress. I was turned on immediately and my feminine senses go off the roof. We kiss each other passionately.
Then, he puts his hands around me and unzips my dress. I feel very submissive at that moment; Samantha was really good at this I thought. Then he grabs my fake breast and the sensation was something I had never felt before. He gets me out of my dress and makes me sit on his lap. He then starts caressing my legs and my chest very gently.
Then as he was going for the back of my bra, the front door opens suddenly. It was Bob; he was back from his vacation early. He instantly turns red with anger realizing there was unwanted visitor in his house. He starts yelling. He doesn’t realize it is me, his old friend. I don’t know how I would ever get out this situation now, I thought inside my head. I was caught.. caught in the act.
I picked up my dress, put in on as fast as I could. Bob was still yelling. He was threatening to call the police now. I had no other choice but to admit that it was actually me.
“Bob, It’s me.. Roger! I am sorry but I didn’t expect you to come back this early” I said in an ashamed tone.
“WHAT?? What the hell Roger, what is all this?” He replied, still very angry.
“It’s okay Bob; I will explain everything to you.” I said, feeling very ashamed.
I push Samantha to go and he leaves immediately. Now, I had to face Bob and explain everything to him. I was never so embarrassed in my life. Bob had calmed down a bit. Then, I sit down on the chair and with a deep breath, I start explaining everything to Bob about me being a crossdresser and what I had planned to do this evening. Bob then comes a bit closer.
“I will forget everything that happened today if you do a favor to me.” Bob speaks.
“YES! I will do anything” I reply back immediately.
Then Bob comes really close to me and holds my hand. I look at him, I was nearly about to cry with guilt. Then with a smile on his face, he says “Well, actually.. I did fantasize about making out with a crossdresser someday. Are you up for it?”
I was shocked. ““No.. Bob, please don’t do this.” I cried, trembling. But it was already too late.
“You actually do make a beautiful woman, Roger.” Bob then holds me in his arm. This was going to be a long night for me, something that turned out to be even crazier. ”