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Crossdressing Confessions Part One
Here are some confessions about crossdressing. These are real stories from real men...ADULT MATERIAL!
***I was on a business trip and decided to dress femme for the nite. I shaved every hair I could, did myself up in a bra, camisole and see thru top with bikinis, a short skirt, thigh highs and sandals. I thought my makeup job was pretty good. It was a big chain hotel but kind of away from most things so pretty quiet, especially after 7 or so. I knew no one at the hotel so it was the perfect time to take a chance going out dressed for the first time. I am bi and I was horny as hell. I went to the bar and ordered a margarita. The waitress giggled a little when I spoke, trying to sound femme probably made it worse. There were only a few guys in the bar, most in pairs and ignoring me. I was half scared, half horny. This older guy at the bar started watching me, smiles and nodded. I grinned back, tried to act sexy. Nothing. Couldn't quite catch his eye. He was discrete but definitely watching me, nothing more. I worked the drink as long as I could then decided I might as well call it a nite. I went outside for a last cigarette and half way thru, guess who comes out to see me? My admirer. He told me I was cute but was embarrassed to be seen hitting on a guy cuz people from his company might be around. Then he asks of I wanna be a real woman tonite. I smiled, licked my lips and said sure. I felt his hard on all the way up to his room and down the hall. He could barely get the key from his pocket, lol. Once inside, he poured drinks and I kinda paced, teased and posed a bit, trying to act sexy. I was lying on my side on the bed when he comes over and shows me the bulge in his pants, says it's my fault. I unzipped him and went to work slowly on him for a little. Then I stopped. Undressed him and he lay down. I let him watch as I greased myself up, slipped a rubber on him and slid onto him. He decided to go doggy so we stopped and shifted then he went for hot and heavy. He got it up twice more before dawn and I took it every which way he wanted. Neither of us were worth a damn at our meetings the next day….wish I'd gotten his number.
***The best naughtiest thing for me was at a a road side park in OH sitting there close to the restroom so they could look if they wanted too. Wearing a black pullover dress thigh highs minus panties, an older gentleman stop and asked for a light, and then asked if I would follow him to a picnic table in the shadows. Getting out there was about 5–6 cars and an older couple walking to the restrooms watching me as the guy took my hand and lead me out of sight (omg what a rush)
He leans me against the end of the picnic table and starts kissing me then pushes down on my shoulders, going down and opening his pants felt like the most natural thing in the world, revealing a very nice cock average length but thinner. I thought to myself ohh I so hope he wants to fuck me with this thing! After sucking him for a bit he leans down and asks if I go all the way I smiled and nodded, he pulled me up, sat me on the table it was the perfect height, hooking my knees he told me to get him inside, reaching down and doing this I then reached up to hold his neck while he slow fucked me. After maybe 5 minutes he picked up steam and drove deep to cum, I was hugging him and kissing his ear I could feel him shuddering hard!
After he calmed and we were heading back to our cars he asked if I wanted to go to his place for a night cap, it was a great evening in his bed!
***I was the ”acting” assistant manager (meaning I did the work but didn't get paid the salary) of a now-defunct office products store in a suburb of Chicago. One night, I came up with an excuse to stay behind after I'd sent all the other employees home for the night and locked up. I'd had a fantasy I'd been wanting to try for some time in spite of the potential danger (I was not the only person with a key!). I'd done a little testing and my fantasy seemed doable, so this was the night!
I retrieved my feminine clothing from where I'd stashed it earlier and headed for the dock, where I started changing. I should note that the store and the dock was a large, open building with display windows looking onto a busy street and only retail shelving to hide behind, so it felt quite naughty to me at the time.
The clothing I donned consisted of opaque beige dance tights, an ivory, stretch-lace, long-sleeved mock turtleneck bodysuit with ruffles around the bodice and at mid-forearm and a long row of fabric buttons going down to the wrist (essentially, it was a theatrical pioneer woman costume that I “borrowed” once and I've not found the like since), and a heavy, powder blue, nylon pioneer skirt that reached to the floor and had a row of ruffles around the knees and ankles to match the bodysuit.
Now the really risky/naughty part…
There was a large outer dock door for trucks to enter and a smaller, inner dock door for unloading merchandise. I'd noticed that if I stood on the lip of the rolling door and hit the 'up' button, it could lift me. This night, I would put the door's motor through its paces!
Removing a bolt from the bottom of the door, I tied a rope through the hole. I then bound my ankles together and tied then to the other end of the rope. I bound my knees together with another rope and bound my wrists together. Then I hit the ’up’ button on the wall and quickly sat on the floor.
Sure enough, the motorized door inexorably rolled it's way up to the ceiling with my ankles attached to it. I hung there with my head several feet above the hard concrete floor for several minutes, enjoying the view and feeling of a helpless damsel in distress. Hearing a distant sound, I soon came to my senses and realized how exposed I actually was and that I would be completely unable to explain myself if I were caught. So I worked my way up to the buttons on the wall (using some core strength and by pulling myself up on the door channel) to hit the ‘down’ button.
All went well and I returned to earth with nobody being the wiser and with a very pleasant memory that I hold fondly to this day, some 30 years later.
***The best naughtiest thing for me was at a a road side park in OH sitting there close to the restroom so they could look if they wanted too. Wearing a black pullover dress thigh highs minus panties, an older gentleman stop and asked for a light, and then asked if I would follow him to a picnic table in the shadows. Getting out there was about 5–6 cars and an older couple walking to the restrooms watching me as the guy took my hand and lead me out of sight (omg what a rush)
He leans me against the end of the picnic table and starts kissing me then pushes down on my shoulders, going down and opening his pants felt like the most natural thing in the world, revealing a very nice cock average length but thinner. I thought to myself ohh I so hope he wants to fuck me with this thing! After sucking him for a bit he leans down and asks if I go all the way I smiled and nodded, he pulled me up, sat me on the table it was the perfect height, hooking my knees he told me to get him inside, reaching down and doing this I then reached up to hold his neck while he slow fucked me. After maybe 5 minutes he picked up steam and drove deep to cum, I was hugging him and kissing his ear I could feel him shuddering hard!
After he calmed and we were heading back to our cars he asked if I wanted to go to his place for a night cap, it was a great evening in his bed!