I’m a pretty ordinary guy, I suppose, but ever since I was sixteen, when I discovered the thrill of wearing female underwear, I just have to cross dress whenever I can. My wife doesn’t mind as long as my transvestism doesn’t take over. I am bisexual; my wife believes that aspect of my character is behind me. So, all of the following episode was unknown to her and yes, I am ashamed but my wife (let’s call her) Kay never found out, so the only harm was to my conscience.
I had been using an online dating site but with little success. Most people liked to chat and swap pictures but the relationships rarely went further. This was one of the rare occasions.
I had advertised myself as a more mature man, tall, slim, small attributes and a bisexual cross dresser, ‘wannabe cuckold’ and sissy.
One evening I had a reply from (let’s call him) Gary saying that he and his wife liked to play and that they were interested. We started talking, swapped a couple of pictures and contact numbers. From the pictures, Gary and (let’s call her) Sue looked very nice, both fit with good figures. Sue had a gorgeous figure, curvy and just perfect. She was Asian with lovely coffee coloured skin and Gary was white, slim, a little shorter than me and with ( I suppose) an average sized circumcised penis. I admit I wanked my small sissy cockette a few times when I looked at their pictures.
Two weeks or so into our relationship we arranged to meet at their house. I got the ferry over to Gosport and Gary picked me up from the taxi rank and drop off/pick up point. Driving to his house I asked if he minded my dressing up. He said that he and his wife did not judge and if that was what I wanted then that was fine. Gary drove ‘around the houses’ to get to his place – he clearly didn’t want me to remember the address – a sensible precaution for a first meeting.
The house was very nice and Gary said he was in the building trade and he’d spent some time getting the house just how he wanted it. The small talk continued for just a few seconds, then Sue appeared in a little white dressing gown. Wow! Gary was a lucky man. We had a cuppa and broke the ice, then Gary invited me to follow him and his wife upstairs.
In the bedroom I stripped off to my lingerie. I was wearing a black padded bra, a black pair of frilly knickers, a black girdle with six suspenders straps and black seamed stockings. If Gary or Sue thought I looked daft they didn’t say so and they both stripped off.
Gary invited me to lick his wife’s ass. I’d already told him I was into ass worship so he knew what I wanted to do. Sue stood up but leant over the bed so I could really get in there. I was so turned on that my cockette was all ready to explode. After a few minutes Gary told me to suck his cock. Oh God! I loved it – umm umm. He was fucking my mouth and I wanted him to cum but he stopped just in time, to allow him to cool off a little.
Gary asked me to lie down, facing up. Then Sue straddled me, in the 69 position. Sue did not lower her wet pussy to my willing lips though. She supported her weight on her knees and Gary stood at the end of the bed and slowly shoved his splendid shaft deep into Sue, just a few inches above my eager face. Gary was very excited, thrusting hard and fast into Sue’s beautiful cunt. Sue was sucking my cockette and I was in heaven, I was loving this.
Gary said he was close and I pleaded, “Please sir may I lick your cum from Sue’s pussy?” Gary told me to beg him. “Please, sir, I beg you, may I clean Sue’s pussy after you cum in her?”
Gary quickly stiffened, grunted like a wild animal and slammed into Sue one last time. “Fuck! That was a good cum,” he said. He slowly pulled out and backed off a little and Sue just leant back and sat on my face.
I loved it.
This was what I was born to do.
It was one of the best moments of my life. I was loving it. Gary must have cum an awful lot because I was licking, slurping and swallowing for a while. Gary told Sue to lift up and for me to open my mouth. (Sue was as submissive as I throughout this, hardly saying a word but she clearly enjoyed kinky sex as much as anyone I’ve ever known.) Gary could see all his milky white cum in my mouth mixed with Sue’s juices too. He ordered me to swallow it and to finish the job, like a good sissy slut.
Sue sat on me again. I was loving this. I kept licking, kissing and sucking and I’d probably still be there now if Gary had not ordered me to clean his lovely cock.
I sat on the bed and he demanded that I do a good job of cleaning his cock while Sue cleaned herself up in the bathroom.
I asked if I may be allowed to cum now. Gary said I had to get myself off while I continued to clean his cock and balls. He was pinching my nipples under my bra – I would not last long
I was soon cumming all over my stocking tops. I of course, scooped and licked it up as well as I could. Gary nodded his approval.
I thanked Sue and Gary and I felt so good I may have even shed a tear of happiness. Gary took me back to the ferry and he said that he hoped that we could do this again. We did. We did it once more before my circumstances changed and I was no longer able to disappear for a day.
I never fucked Sue, Gary didn’t fuck me. I never fondled or sucked Sue’s beautiful tits but this was still the hottest thing I could remember doing.
On the way home I could still smell Sue and Gary on me. I could feel my sticky stocking tops, I could feel my sissy little cockette leaking more cum and I wondered what people would think of this respectable looking middle aged gent?
