My first experience was about 5 years ago. I had been dressing for two decades before Over the previous 5 years I had been posting photos on various sites and getting interest from horny guys. This had led joining fabswingers. Initially I had been looking for MF couples, but along the way I had attracted some attention from guys. This led to fantasies about meeting guys and after chatting to an experienced admirer I decided to expand my horizons.
I parked in his drive and let myself in, following instructions to the spare room. I got dressed and made up surrounded by unfamiliar signs of this man's vanilla life. I was nervous, excited and sort of in a trance. I got made up in his bathroom (badly!), put my heels on and then my blonde wig. For me, the moment I put on my wig is the transformation to Kelly. I looked ok and walked across the landing in my black Pleasers platforms (such fab shoes!), my skirt hardly long enough to cover my caged clitty. I knocked and in my best feminine voice said "hello".
I heard a reply and entered his home office, although the images on his laptop were not ones you want the IT department to see. He inspected me, asking me to turn 360 degrees. He sounded approving. Next I followed his direction and fell to my knees. Within seconds he was unzipping - 'no backing out now, Kelly'- ran through my mind. Presented with a semi hard cock I did what was expected and took it into my mouth. It was only the second cock I had sucked, the first much bigger and belonging to a beautiful Brazilian TS I met in a Parisien bar.
His cock was a bit 'pissy' but I stuck to it being a good girl. It hardened in my mouth giving me a thrill and his moans sounded like I was doing ok. I cupped his hairy balls as I tried to take him deeper, causing a few gags, which he seemed to like. He was mild mannered and gentle, rather than the controlling Dom I wanted but was terrified of, too.
After some 15 minutes he led me up some steep stairs, me first, him pinching my barely covered ass. In the bedroom was his 'fucking bench'. He strapped me to it causing mild but unexpressed panic. 'Fuck... he could do anything'
Aromas appears at my nostril and I sniffed as instructed and soon the now familiar woosy horniness took over as I heard him slipping on a condom. Pain followed by the popping release of my hole. I was being fucked...dressed as a slutty woman by a guy... wtf!
He came pretty quickly and then put another condom on and was back fucking me, presumably recharged by the blue pills in his system. He came again and repeated a third time. I had been sniffing and taking it like a good girl. Was is mind blowing - no - but he was a thoughtful and caring guy who popped my cherry.
After I showered, removed make up and dressed back in my drab males clothes as he hid in his office. I walked out, got back in my car and drove off. I remember saying out loud..."Kelly, you naughty girl!"
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