Cross Dressing
14 Jan 2025


Well Christmas and the new year over we start to think about Holidays, Let me introduce myself, I am Cathy, A mature CD from Cambridge, If you have read any of my past experiences you will know that i still live in the same house as my wife, We have had seperate lives for twenty years, after she discovered my desires were for men, As we both got older we gave up the desire to holiday abroad and went for the more relaxing fun holidays in the uk, Last year Pam , my wife had met a much younger man, something she has always had fantasys about, I think it stemmed from when we used to host young language students, I was never impressed by her choice in men, The teenage biker type, Hardly fitting for a woman in her early sixtys, Anyway, not my business , Her current man is in his early forties, A chap from our local pub, He has a caravan in Skegness, he and his younger brother were going for a weeks beach fishing and invited her along, so that was her holiday taken care of, I had enjoyed a quite active summer cruising around in my van and fancied a quiet holiday with no driving so i settled for a weeks coach holiday in Eastbourne, The drive down was idylic, The east beach hotel was perfect, i was given a lovely double room, I had dressed down for the holiday, mostly wearing slim jeans and shorts, The first two days were spent discovering the town and surrounding walks, It was the afternoon of my second day, i had had a busy morning, had a late lunch in Wetherspoons , i had popped into the toilets to apply just a hint of eyeshadow and some modest pink lippy before continueing my walk back to the hotel, I was approaching the hotel from the street that runs along the back when i spied a small charity shop, I adore charity shops so i couldn't resist going inside, It was quite late and there was just an elderly lady looking at the racks of clothes, The shop was staffed by an elderly gentleman with a tiny goatee beard, he was immaculately dressed, The elderly lady left the shop, I was browsing a rack of size sixteen when my eyes fell upon a pretty short pleated skirt, it matched a purple blouse that i had selected from aanother rack, I suspect that the gentleman was keen to shut the shop before another late customer entered , he approached and stood in front of me "Oh a lovely choice if you don't mind me saying, I am sure she will be pleased." Whether it was because i was on holiday and a stranger here but i felt so confident and quite excited when i smiled and said, "They are for me actually, I know the blouse will fit, I'm not quite sure of the skirt, my hips are a little on the big size," For a moment you could have heard a pin drop, The gentleman coughed, "I am sorry, no offence intended, " " none taken i assure you," He took a step backwards and looked me up and down, "I think you are mistaken about the skirt, i think it would look quite fetching, We have a small fitting cubicle at the rear of the shop if you would care to use it". As i turned to walk back i noticed him got to the shop door and lock it and turn the sign to closed, when he returned he said, "I was about to close anyway, My wife collects me in half an hour", His eyes never left me as i removed my leggings and stood in red holdup stockings and and black panties, He handed me the skirt, He was right, it fitted perfect, Agave a small twirl the skirt lifted showing my stocking tops, "God you bottom looks wonderful in those panties, it has got me quite excited , I smiled at him, "What a shame, your wife will be here soon,, I better get changed, I quickly slipped out of the skirt and replaced my leggings, The gentleman looked quite desperate, "Look i would love to see you again, do you live here?" i explained that i was a holiday maker staying at the hotel that backed onto the shop, I told him that i was a transvestite on my holiday alone , He told me his name was Adam, "I have never been with a transvestite before, Do you? before he could say anything else I stopped him, "Yes i do go with men, If we get on i let them fuck me, I am also a very good cocksucker, I am sorry if i have shocked you but i know how men think, I can pay you for the clothes now and we can part as friends," "Oh.No No please don't say that i want to see you again." i must admit i was quite smitten by him too, "Well i am staying in the beach Hotel, i am having a night in, if you care to join me you will be welcome, , Oh yes that would be wonderful, As we stood there i heard a car horn pip from outside, "That will be the wife,I will let you out the back door." He stood frozen to the spot as i leaned in and kissed him, I reached down to stroke his trousers as my tongue snaked into his mouth, Eight oclock i sat in my room, i had showered and was wearing my new skirt, I was certain he would come, i had told the desk porter to send him up when he arrived, I know men, i knew he had a fantasy, , There was a soft tap on the door , i opened it and he came in, This time it was he that leaned into me, It was his tongue that snaked into my mouth, "Oh Cathy, the skirt looks divine, he placed a bag on the floor, "I hope you won't be offended but i have bought a selection of my wifes panties, want you to choose a pair to wear when we do it," I smiled at his coyness, "She wears a fresh pair every day so they are quite clean" i reached into the bag and withdrew a pretty blue pair i held them to my face, i could smell the musky smell of a womans cunt. "The red pair are the ones she has been wearing today", again i reached into the bag and selected the red pair, The musk was much stronger and there was even a hint of dampness, I quickly removed my black panties and replaced them with the red pair, I felt my clitty leak a little as her dampness mingled with my own, Looking back at Adam i could see he he had released and was stroking a fine curved eight inch penis, I reached and gripped the hot shaft, very slowly i eased the forskin back , revealing the purple head, i bent forward to take him in my mouth, he groaned as i sucked him deep, the speed he moved quite surprised me "No Cathy , Not like this the first time" he had withdrawn and was forcing me to my knees , With my head on the bed he lifted my skirt, gripping my hips he pulled his wifes panties to one side then positioning his penis against my cunt he lunged , My cunt seemed to suck him in, I gasped as eight inches of rigid penis burried itself deep in my cunt. "Steady, Adam , please take your time, your hurting me," it fell on deaf ears, again and again he withdreww until just the tip remained inside before thrusting all the way in again, It was me that cried out first "Oh my god Adam, i am cumming, Fuck me , fuck me harder, " i felt my little clity spurt into the red panties to mix with his wifes musk, I felt Adams hands move up to my shoulders, hauling me back as he thrust deep inside me, i collapsed on the bed, allowing him to ravage my cunt, Relief came with a deep groan, spurt after spurt of warm spunk spread inside me, We lay together for what seemed like hours, When we finally parted He kissed me again, "My first time was awesome Cathy, far better than i could ever imagine ," I smiled at him, I know i am good but a girl can't have to many compliments, "I am glad you enjoyed it, But you still haven't been sucked off by a tranny," He smiled as i watched his penis begin to stir, It was still flacid as i leant over him and took him in my mouth , I sucked for about ten minutes before he was fully hard, My tongue had explored every crevice and he was leaking precum, "Oh yes,Suck it Cathy , " He withdrew and rolled me onto my back on the floor, i could see his peniis bobbing about as he straddled my face, i opened wide as his penis found my mouth, I felt such a wanton whore as he fucked my mouth, even a cock sucker with my experience couldn't refrain from gagging when he went deep, He paused to rest, i could feel his cock head resting at the back of my throat, I noticed he still had over an inch of shaft exposed, Holding his hips i slowly raised my head, The pressure at the back of my throat increased, i still kept lifting, when i thought i could take no more i felt his cock head pass the barrier into my throat, "Oh fuck, yes" he Groaned,, neither of us moved, then i began small swallowing movements as my throat began to milk his penis, I felt it before he cried "Fuck,Fuck, I am cumming, " there was no taste just the hot spurt after spurt of spunk directly down my throat, Afterwards we lay in each others arms , "It's tuesday Cathy, I can't believe your here till Friday , I still wear her panties , Cathy xx

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