A couple of months ago I was on a business trip to a major city. I was looking forward to visiting the city and the opportunities that it should offer to have some extramarital fun as I like to have some man to man action on my business trips. To my disappointment the meeting was held at an office in a remote industrial park far from the city where there was one lone hotel and nothing else but empty office buildings after hours. I had to endure a business dinner at the hotel dining room and there was no real chance of hitting the city that evening.
During the dinner I discreetly looked at Squirt and the closest hook up was 20 miles away and not even an interesting one. After the dinner I decided to have a beer alone at the hotel bar. I pulled up my phone one more time and to my delight there was a hot daddy bear less than 100 ft away. I wrote to him immediately and got a quick response that he was looking for a cross dresser and asked if I was interested.
Cross dressing is not in my palette of sexual proclivities, but I hated to turn him down so quickly since he was hot as hell and the only game in town. He was 49 years old, 6 foot 2 inches and 220 pounds. He sent some more pictures including his face and I was immediately hooked on him. He was adamant that if I wanted to play, I would have to cross dress. I wrote back that unfortunately I did not have any women's clothes with me hoping he would agree to meet me mano a mano. He quickly shot back that he was only interested in CD and it was no problem, he had everything I would need.
Mentally I was pissed at myself for being so desperate, but my hungry hole and cock overruled, and I texted back my agreement to his terms. I reached his room, knocked on the door and he opened up to let me in. He seemed aloof and I was uncertain if he was still interested.
He told me that everything I needed was waiting in the bathroom and I should go and get ready. He asked if my ass was smooth and fortunately, I had shaved my privates prior to this trip. I was concerned that he would start to ask me to shave my legs and chest, but fortunately he didn't. He did say that I had to put polish on my finger and toenails. When I heard this, I was just about to back out, but I looked at his crotch and saw his dick snaking down his trouser leg and I went into the bathroom.
There was quite an array of advanced equipment. There was a long blond wig that actually fit quite well and didn't slip or move around. There was a bra made of some type of memory foam that actually felt like real breasts when squeezed. There was a jockstrap-like pair of panties that gave full access to my ass but discreetly covered my cock and balls. I dressed, painted my nails and applied lipstick and I could feel my cock starting to expand and fill the panties.
I exited the bathroom to find him sitting on a chair still in his suit sipping a whisky. His demeanour of aloofness vanished when he saw me. He became very attentive, he arose, took me by the hand, put his arm around my waist and leaned in for a kiss. His tongue filled my mouth with a masculine mixture of the tastes of whisky and cigar tobacco. I enjoyed his attention and massaged his massive bulge.
He picked me up and threw me on the bed, held my legs up in the air and started to lick my ass which he called his cunt'. The sensation was overwhelming. I held his head down in my cunt' and he lapped, slobbered and tongue fucked me roughly. He stood up and disrobed and I got a good look at his manly body, hairy chest, his long, fat cock and shaved balls. My cock was straining in the panties, but his only focus was my ass. For him, my cock did not exist only the `cunt' before him.
He was massively strong, and he picked me up, I placed my legs around his waist, and he kissed me deeply. I could feel his hard cock teasing my cunt, moving around the hole and up and down my ass crack. Still holding me up on his body, he lowered me down to where his cock could penetrate me. He teased the head in and out of my hole but held back on full penetration and all the time kissing me deeply. I felt his strong back muscles and moved my right hand to play with his nipple. He found this exciting and began to push his cock deeper into my horny hole. I could feel it moving in inch by inch expanding the tract with each small inward thrust.
I looked into the mirror on the wall and the image that appeared back was striking. I did look like a woman. My red painted fingernails on his strong shoulders, the red toenails topping my feet that were wrapped around his waist, and the long blond hair in contrast to his manly hairy back. I suddenly became so turned on because I felt like I was his woman. There was something to this visual image that encompassed my and I embraced it. I bucked gently up and down so that his cock would thrust deeper in me and he reciprocated by increasing the rate and power of his fucking. He was damn strong as he continued to hold me up and fuck me for a good 10 minutes. My hole was quivering from being attacked at this strange angle and I felt like I was going to cum right then.
He apparently sensed I was about to reach climax and he withdrew his cock, turned me around and threw me on the bed. He got behind me, pulled me up and starting to fuck me doggy style. He had good a technique where he switched between a hard, fast fucking rhythm and a slower more powerful stroke. Each time his balls slapped my ass with a sound that was starting to become hypnotic. He panted and called me baby and asked me if I enjoyed daddy's fat cock in my pussy. I could only groan yes daddy! Fuck me daddy, Fuck me harder! I was completely focused on the pleasure that he was providing my hole and had not even thought about my own cock during this time.
After pounding me doggy style for a good 15 minutes, he turned me over, threw my legs over his shoulders and plowed deep and roughly into my cunt. His hands were working the fake breasts and he leaned in and kissed me hard. It was a turn on to see my red lipstick all over his face. He was like a fucking machine pounding my hole like a metronome, his balls slapping my ass. He started to get rougher and was slapping my thigh and buttock and asking me who was his bitch. I could only muster enough to say "me, daddy, me". This continued for long enough that I lost track of time.
I could feel that he was starting to build up to an orgasm and at that point he asked me if I wanted to play with my clit so that we could cum together. I reached down and felt my hard cock in the panties. The panties were dripping wet with my pre-cum. I stroked my `clit' in rhythm with his fucking until we both exploded into a mutual orgasm, both of us moaning and growling so loudly that everyone in the hotel must have realized that this was the greatest orgasm to ever happen at this place.
We relaxed back onto the bed and I laid my head on his shoulder and we fell into a deep post sex slumber. We were both so spent that it was already 7 am when we awoke. We both had to rush around to get ready to go our separate ways.
I went to my room and took a shower and as I was tying my tie, I noticed that my fingernails were still red! I rushed down to the reception to see if there was a gift shop where I could buy nail polish remover, but alas, there in the boondocks no such thing. I asked the female receptionist if she knew where I could get some nail polish remover. She told me she had some in her purse I could use. As she handed it to me, she saw my hands......I wish I had a photo of the look on her face....
While this was an exhilarating experience, I have still never embraced cross dressing and that was probably the one and only time I will ever do that.
Feedback is welcome!