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My long term girlfriend knew that I had a passion for lingerie and would (when the mood took her) let me wear her panties during sex but she never knew the full story about my crossdressing. As well as dressing up in my girlfriend’s sexy undies at every opportunity, I had a large stash of my own hidden away in the garage where it wouldn’t be discovered for special occasions when I had a few days to myself to indulge my secret passion. I have a sissy maid fetish and when my girlfriend was working away I’d fully transform myself into a sexy maid. Makeup, wig, nails, jewellery, stockings, heels, the lot. I’d then do chores in a sexy feminine manner, cleaning, ironing etc while plugged and in a chastity cage. My desires had progressed to wanting to be dominated, humiliated and cuckolded, for some reason the thought drove me wild! I also fantasised about being forced to suck my girlfriend’s lover’s cock when she cuckolded me. At the end of my dress-up sessions I’d usually end up eating my own cum or lying on my back with my bum wedged up the wall so I could give myself a facial while imagining it was another man or TV cumming on my face and ruining my makeup. On one occasion, my girlfriend’s daughter stayed over for a few days before heading back to university and brought her boyfriend. They tried to be quiet while they were having sex but they were fucking literally all of the time. I was in the house during the day and listened to them whenever I could. After the second day of listening their constant fucking I decided to spice things up a little bit and slipped on a pair of my wife’s lace panties and sheer hold-ups on under my jeans and it certainly did the trick for me! I couldn’t wait for them to leave for lunch and as soon as their car was out of sight I raced up their bedroom to satisfy my curiosity. There was some gorgeous underwear strewn around and some lace top stockings discarded in the corner. I held the soiled panties to my nose to smell her freshly fucked scent which immediately made my cock harden against my wife’s panties and then I noticed the bin. It was full of used condoms! I picked a few up and examined it as I held another man’s cum and my girlfriend’s daughter’s juices. Without hesitation I licked it. Nothing much to taste to I tentatively rolled the condom up so I could touch the cum with my tongue. I was so excited that I was shaking at the thought of doing this humiliating act! I took the condom, stripped off to my sexy undies, lay on my and masturbated while rubbing the condom over my balls and face. Just as I was about to cum I emptied the cum from the condom onto my face making sure some went into my mouth. I was immediately disgusted with myself, put the condom back into the bin and returned to my normal clothes. I couldn’t stop thinking about degrading myself with a used condom and was considering doing it again but they arrived back. I thought about nothing else until they left for Uni and my girlfriend left for a three day conference. As soon as I had the house to myself I grabbed my secret stash from the garage. In record time I’d shaved, changed into a sexy basque, waist cincher, stockings and black patent heels. Nails next and then a sit down in front of the makeup mirror. I took my time and when my wig was adjusted I looked quite stunning! On with my maids dress and on with my chores. It wasn’t long before I was drawn to the condom bin. I played with the cum, tasted some, rubbed some on my cock and even dared to swallow a little which I loved. I took plenty of pics to remind me of my degrading humiliation. I decided that I needed a butt plug so opened the bedside draw and picked out my girlfriend’s pink plug. I then put my ass into the air and emptied the cum from a condom onto my gaping and ready ass. The feeling was amazing as I felt some of it enter me. I lubed the plug with another condom and slid it into me. I was so excited that my cock was leaking pre-cum by the pint! I removed the plug but made sure my hole was relaxed and open as I emptied the contents of another four condoms inside me and replaced the plug to keep it all inside. After this I knew I was hooked on condom humiliation. When I split from my girlfriend a few months later I had time to advance my little hobby. I’d crossdress under my male clothes and frequent car parks late at night to find couples having sex. I’d park nearby so I could hear them and strip off to my lingerie as I played with my cock and wishing it was me getting fucked. My heart used to skip a beat when I saw the door open and the condom get discarded. As soon as the coast was clear I’d strut over in my stockings to retrieve it. I loved picking up a warm condom full of fresh cum and covered in juice to play with. Sometimes I’d roll it onto my cock and add my cum to the contents. I still do it to the present day and have hundreds of pictures to remind me of my degradation. I hope you like my confession. X
My adult step-daughter knew i was a crossdressing sissy, & came in from a date drunk one night....She stopped by my bedroom, saw i was watching IR gay porn in my French maids uniform....She laughed, stripped off her wet, dripping panties, tossed them to me & said, if you can guess whose cum it is, you can lick the rest of it out of me....i guessed, but it was the 3rd guy i guessed, so i had to be happy sucking cum off the panties!!! She knows me SO well!!!
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Over on the wrong side of town, there's this secluded park, right next to a nightclub. The club opens 11pm sharp, and for half an hour before then, the park's filled with couples. You can hear them in the bushes, fucking like rabbits before the club opens. I guess they have nothing better to do besides screw each other in the bushes. Then, one minute past eleven, there won't be a soul around. They all rush off to dance at that nightclub. Don't believe me? Neither did my fiancee. My fiancee's name is Katie.
"Come along then if you don't believe me," I said. Katie and I were lying in bed cuddling.
"I would've heard of it," said Katie. "Remember, honey. I'm in a sorority."
"This isn't the kind of club fancy college girls visit," I said.
That piqued her interest. "Let's go tomorrow night," she said. "I have to see it to believe it."
So that's how I ended up taking my sheltered rich white-girl fiancee to the wrong side of the train tracks. Imagine a girl like Katie walking around that seedy area, with her perfect skin and her perfect blonde hair. To make matters worse, she was NOT dressed appropriately. Her Ugg boots told the whole entire world she was a naive little co
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