Caught Crossdressing by Aunt Sharon
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My Qualifications to Write About Crossdressing By Ricky How ironic! While looking for something in my files the other day I found I have been writing about crossdressing more than 10 years now. The problem is, I now realize I am completely unqualified to be a crossdresser, let alone a writer on the subject. Think about it, just what are the qualifications for a crossdresser? Surely you've read a multitude of "true life stories" in the crossdressing magazines. Perhaps if we...
I had an affinity towards women’s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours – I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my mom’s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a...
Cross DresserHii, mere naam ankit hai. Main mumbai ka rahnewala hoo. Yeh kahani meri or meri mami ki hai jab hum sath me crossdressing kiya karte hai. Meri mami ma naam sabita hai. Unki lambai 5ft or woh thodi moti type ki hai. Unka koi baby nhi. Lekin fashion ke mamlo me save age rahti hai. Jab mai 10std me padta tha tab meri mami or mama culcutta se mumbai aaye. Yaha aane ki unki ek hee wajah thi paisa. Mujhe pahle se hee porn video dekhna achcha lagta tha. Mujhe femdom, bdsm, bondage jaisi porn bahut...
SOME NOTES ON THE DESIGN OF CROSSDRESSING HARDWARE There are several difficulties to be overcome in the design of self-crossdressing hardware. This paper will enumerate them and offer suggestions to remediate the problems. 1) Determining the sex of the hardware. Actually, determining the sex of the hardware is not a formidable task. The primary problem occurs because design engineers have no discernible knowledge of sex. After all, anyone who spends their day in front of a...
HumorI live in a high-priced apartment in a big city and recently I got new neighbours. They were couple in their mid-thirties and they politely introduced themselves to me. He was a businessman named Arnold, she was a housewife called Paula, who was pregnant with their first child. They seemed friendly enough folks, but I didn’t pay much attention to them. I like to be by myself and usually have as little to do with my neighbours as possible. A few weeks after my new neighbours had moved in next...
I was a single male in my late fourties, who has a really good job and therefore really hardly any time for relationships. I live in an apartment in a city and recently I got new neighbours. They were couple in their mid-thirties and they politely introduced themselves to me. He was a businessman named Andrew, she was a housewife called Paula, who was pregnant with their first child. They seemed friendly enough folks, but I didn’t pay much attention to them. I like to be by myself and usually...
Straight SexNafis stood at her back spare bedroom window, which just about overlooked her neighbours garden. When she pushed her face and ample tits up against the window, she could see parts of her neighbour's deck area, where a week ago she saw a 2-day orgy take place. Her clit was still sensitive from all the rubbing she had given it while watching the events take place, she changed her dirty cum soaked panties 3 or 4 times a day as her cunt leaked in the gusset, At night, laying in her bed next to her...
Mary stood staring at the flat passenger side rear tyre of her car in horror. This would definitely have to be the proverbial straw on the camel’s back. She felt the beginnings of desperation start to settle in and fought hard against it. She was not going to give in. She was determined not to give in. Not today of all days. Stating that she had had her share of ups and downs would be an understatement. As the very first drops of the forecast rain started to fall, she bit down hard on her lower...
Straight SexUp until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole deal at least one time to see if I’m really as into it as I thought I was. I also mentioned that it wasn’t...
CrossdressingDonna and I were watching a movie one Saturday night, when there was a knock on the door, I answered it to find our neighbour, a young pretty Asian girl, crying and obviously in some distress, I invited her in and she came into the lounge, I told her to sit on the sofa, where my wife was sitting, she was crying and we put our arms around her and she told us the problem.Her husband had been screwing her sister, and she'd just found out, it had been going on for a couple of years, she was really...
This is part one of a story, from a former user. I’d like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great. First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. —– It was the height of summer, and my girlfriend was out of town for 2 weeks. I’d had a handful of experiences with guys before, but ever since I...
This is part one of a story, from a former user. I'd like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great.First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. ----- It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I...
Hi, I am Sumaiyya. Yes, this is my original name but then, I don’t care since there are thousands of Sumaiyya all across India. Please don’t try to hit me on Instagram since social media is not my cup of tea. Since this is my first installment of the story, the introduction might take a bit of time but I request you to bear with me. I am pretty sure you will love it. I remember I was in my teens when I came to Calcutta with my parents. I looked a bit like Hina Khan, but was not so fair in...
Friday night crossdressing. Doing a favor for a gay neighbor gets me more exposure when a friend finds out I like crossdressing. Continued… Gail walks up to Candice, leans over and they start making out. Before I knew it everyone had a partner and they were all making out except Mark and I. As I said before, Mark and I have known eachother since grade four. I heard he made a pass to another guy once but I thought it was just a rumor. I've always liked crossdressing but didn't consider...
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to...
Hi all, this is Raj from Mumbai, sharing the experience that I had with my hot neighbour, Nandini over the course of two afternoons. About myself, I am a 28-year-old professional working and living in Mumbai, 6 feet tall with a normal physique and a 7-inch dick that can satisfy any woman. Coming back to the story, across from where I was staying, stayed the heroine of this story, Nandini. Nandini was this bombshell MILF. She was 45 years old, about 5 feet 5 tall, with a beautiful face, big,...
My older neighbour was always looking at my girlfriend. He's nearing his 50's, large built, shaved head, likes to think he's quite aggressive and dominant. My GF is in her mid 20's, slim but with a decent sized bum, a bit like a porn star...it's noticeable and always attracts the attention of other men. She has quite a dirty look about her even if she doesn't mean too. She looks like she has a high sex drive but doesn't want to make it obvious. Basically, my older neighbour imagines her to have...
Well, the 3 weeks that were supposed to pass before we met up again, became 3 days as we hooked up again yesterday. His friend really enjoyed his gay experience and he bugged my neighbour so much that we wound up in a motel last night. I told my wife that I had to go away on a last minute overnite trip and I met them at a clean motel not too far from my house. They had gotten a room with plenty of space for the 3 of us to sleep and the general idea was that we would have some drinks, watch...
‘Shit!’ Chrissy swore to herself as the heavy box slipped out of her hands and fell onto the floor in the middle of the hallway. She wiped the sweat from her forehead and sighed heavily. Thankfully this was the last box. They had been lugging her stuff up to the fourth floor apartment all morning and she was just about wiped out. ‘They’ were she and her boyfriend Robert. After months of hounding on his part, she had finally agreed to move into his little one-bedroom apartment. The two had...
A tight circumcision from my Muslim neighbourTime to tell a story. One that’s just happened, recently. My name is Paul. For my 18th birthday, last year, Dad bought me a used Ford, as my first car. Nothing too flash. I shouldn’t have had a beer with my friends because when I returned home alone with my new prize, I made a mistake. We live in a cul de sac dead end street and as I was parking, I scraped the neighbour’s car. Not just any car but my neighbours European Merc. Just a small scratch on...
Well if you have read my previous stories about my neighbour you will have an idea of whats coming.If your all settled i'll begin.It was the Friday before christmas, Crazy Friday its called and we were going out with friendsfor a few drinks we intended to start early and finish at a reasonable time before alot of the dickheads started to get pissed.I lay on the bed reading after my shower and waited for my wife to come into the bedroom after her shower she did with a towel wrapped around her...
Hello friends, this is Ajay. This is about how i had sex with my neighbour girl who is just 19 years old. My neighbour is a Orissa family who recently got a baby girl. Since both are working, my neighbour brought her sister to Bangalore. She is the heroine of the story. She is just 18 years old. But has a very good body & structure. She is definitely a virgin. The most beautiful asset of her body is her ass. Her ass is well shaped and tightly packed. I always had an eye on the girl from the day...
I moved into a house in a quiet town after a long soul sucking marriage and a bitter divorce, and now I was looking to start fresh.Late in the afternoon I saw my new neighbour for the first time, she was fairly tall, slim, pale as snow with bright red hair hanging down her shoulders and a bosom that was trying to fight it's way out of a very tight t-shirt."Hi!" I said smiling as she pulled her car up a few meters away."Hi to you too!" she replied back with a smile."I'm Joe" I said staring at...
Many of the crossdressing life stories I've read on Lush have similar beginnings. The early adolescence, the mother's or sister's clothes, the masturbation! It's fifty years since my first urge to dress in feminine garments, and ever since then, it has been an integral part of my colourful life.I remember the day fairly vividly. I was settling down in our bathroom, to do what EVERY adolescent does at that age. Wank! My inspiration back in those days were my mum's pals, her sister, and a couple...
CrossdressingI have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained.I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...
CrossdressingI went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...
Introduction: With sisters help on New Years Eve, he fucks his MILF Neighbour. BEST PRESENT EVER: MILF NEIGHBOUR Summary: With sisters help on New Years Eve, he fucks his MILF Neighbour. Note 1: This is the third part of the Best Present Ever series. In Part One (Bitch Sister), Matthew turns the tables on his bitch sister making her his personal sex slave. In Part Two (Cheerleader Orgy), Matthew has a fun foursome with his sister and two other cheerleaders. Of course, I suggest you read the...
Hi friends, I am j*** and I am from Cannanore in Kerala.i am narrating my first experience with my neighbour house wife her name is Sindhu whose hubby in abroad about 5’4″ tall, 40yrs old lady she had big boobs and nice round butts She had a sexy walk as she swayed her hips oblivious to the reaction she caused in men who observed her. She dressed in pastel colored sarees and usually wore a pleasant jasmine perfume that was very sensual. She was a good lady and I considered myself lucky to be...
For the fourth time in as many days, my cock erupted into the pair of red satin panties wrapped around it. In my mind, it wasn't the panties I was shooting my load into, but what they normally covered. At sixteen years old, I was technically still a virgin. I'd had the odd grope of my girlfriend's tits and once, even got to feel her cunt through her panties but as far full sex was concerned I was a virgin and relied on my fist for my satisfaction. Of course I knew it all in theory, I had a...
Hi everyone, I am Karthik, 26 years old from Bangalore. I work as a senior software Engineer in a product-based organization. This story is about a real incident where I fucked my hot, sexy and busty neighbour. So, we were neighbors in Noida. They have been staying next to us for around 6 years. It was a family of 3. An old couple and their 29-year-old daughter, Dipali. Dipali is an assistant professor in an Engineering college. Dipali is a beautiful and sexy woman. She is 5.6 feet tall, has a...
When we moved in one of the first things that I noticed was that our neighbour liked to smoke out of one of her roof windows which over looked our sitting room. Sometimes I would be sitting on the sofa watching TV or browsing the internet, well lets be honest, looking at porn!!!!, I would see her swing the window up and light up. Once or twice I had thought she might have caught me stroking my cock as I looked at porn. I do this sometimes when my wife is at work,, well don't most men!!!. Of...
Sue and I have lived in the same house for 18 years and we have watched our k**s grow and move out, our neighbours have been in their house longer than us but decided to move, downsize. we asked them who was moving in and they said a young lad on his own, he works away a lot so bought as an investment. ok lets hope he doesn't have parties when he's home! lol. don't worry they said he seems sensible. Sue and I continued with our lives and we never really seen the new neighbour only when passing...
My name is Justin. I'm in my mid-thirties, which is a pretty good age to start reflecting on your past, and take stock of where you are today. I've been looking at some old pictures from when I was in my early twenties. I wore the cool slacker/skater look quite well. I was a tall, with long wavy brown hair that hung down to my jaw line. I wore jeans and retro T-shirts all the time during the summers. In the winters I'd add a thick sweater and jacket to the ensemble. I was very skinny at the...
MILFTHE LATE CROSSDRESSING HUSBAND by enduringshades Edith and I had known each other since we were teenagers. We went shopping together and often met for lunch or coffee. Friday night used to be our Girls Night Out when we dressed to the nines and headed for our favourite bar. Then we got married (not to each other!) and stopped going out together. Edith was still a party girl, but I stayed at home with my wife, Betty. I never told Betty that I was a crossdresser. I missed being...
It was a tuesday evening, i had just pulled up in my car and my neighbour Rachel was waiting outside for me. Rachel had recently divorced her husband and we had started to chat over the fence since, she was a very pretty brunette with what i could see a very good figure, she had only been my neighbour a couple of months before her husband left her. Anyway it was nothing new that Rachel was outside, she was normally out there watching her k**s playing in the street. As i walked down my path, she...
I was over the moon when the live in warden of the block of sheltered accommodation flats where I lived told me the new tenant of the next flat to mine was a single woman around my own age. “At last,” I thought, “someone I can talk to.” Pretty well every tenant in the block was much older than I was and I had little if anything in common with them so someone my own age, early sixties, would make a pleasant change. It was about a week later on Wednesday morning when she moved in. I saw the...
I live opposite a single woman who I fancied something cruel. She appeared to have a very active social life with lots of men friends. I thought her unapproachable since my partner would very quickly be suspicious if I was to have an affair so close to home. We actually nicknamed her trollop due to the many men she entertained.One Saturday my partner was out for the day and there was a knock at my door. I was amazed, and delighted, to find that it was the neighbour from across the road. Could I...
So it happened. My wife had a sexual encounter with our young neighbour. Unfortunately it was not something I was aware of until I accidentally discovered them together.Let me start by saying that my wife has had many fantasies involving our young neighbour Troy. He’s currently 22, blonde and a muscular 6 foot, hitting the gym every day after work. She is 45, fit, petite and extremely hot. We’ve dirty talked many times about her fantasies with Troy but she has never had the courage to try to...
With a groan I slammed my almost emptylager bottle onto the table and stood up. I briefly debated putting on some trousers but then figured what the hell – if someone wants to knock at the front door ten minutes after I've got home from work then they'll just have to put up with me in my white Calvins and shirt. Opening the door I was a little surprised. It wasn't some kind of charity mugger or local councillor garnering votes. No, it was my hot as fuck neighbour, Warren. I could qualify that...
Gay MaleAfter seeing the overwhelming responses from the ISS readers, this story is about how I fucked my neighbour a month ago. I live in Chennai and her name is Savitha (name changed) and she is from Andhra. She lives with her husband and her kid in our flats as they have recently shifted to Chennai due to her husband work location changed. To tel about her, she is little bubbly, not too much of over weight, but the weight a woman gains after giving birth to a baby. Am not sure about her size as I...
Hello All Hope everybody is doing good. I am here to share my sexual encounters with my neighbour. To start with, I am a software engineer from Hyderabad and I am 27. I am fair and good looking guy and I stay at Miyapur in a single bed room flat. There is this lady around 35 who stays next to my flat. I met here few times earlier while coming and going out of my flat and exchanged some casual talks. Her husband too works for an IT company and had been to US and she was staying alone. She is a...
1 The Early Morning Show I’d never thought of my neighbour, Hazel, as anything but that, a neighbour, a good neighbour, but just a neighbour. She was in her late sixties so the thought of her having sex had never entered my mind. That was until late last night!!! I’d been out with the lads and it was late, very late, around two in the morning. Most of the tenants of the small block of flats where I live are in their seventies and eighties, definitely not your typical night owl, so I was...
1 The Early Morning Show I'd never thought of my neighbour, Hazel, as anything but that, a neighbour, a good neighbour, but just a neighbour. She was in her late sixties so the thought of her having sex had never entered my mind. That was until late last night!!! I'd been out with the lads and it was late, very late, around two in the morning. Most of the tenants of the small block of flats where I live are in their seventies and eighties, definitely not your typical night owl, so I was...
Erotic FictionI've decided to switch the category for these over from blog post to sex story, as at this point in my adventures as a gay crossdresser, I had pretty much hit my stride dressing up and finding men and other crossdressers online to have sex with. So I guess you could say my posts moving forward will be a little more "action" oriented. Plus at this point it is hard to remember all of my experiences chronologically, and for the most part that's really kind of irrelevant. If any of you are...
As you know i was trying to buy a new property but was having no luck.The only good thing to come out of my search had been that the estate agent had become a regular fuck buddy.When i did eventually find a place i was hoping that she would help me christen my new place.As it was one of my new neighbours achieved that honour.I had only been in there a little while when my next door neighbour came round.She was in her late fifties,long blonde hair,with nice pert breasts and a tight,firm ass.She...
The new neighbourFall arrived and with it the annual ritual of moving, people seeking new places for the winter. This year the usual influx of students was curtailed by the ongoing “emergency”.Of interest to me was a flurry of activity next door. A moving van, people bustling around, unloading, carrying boxes and furniture inside, could this be new neighbours?The house had stood empty for four months. The backyard was a wasteland of discarded clothes, toys and broken furniture. Contractors had...
I am now a 31 year old male, who had an experience with a woman 18 years older than me. Soon after my 14th birthday, we had new neighbours moving in next to us. They were a young couple both in their late 20's. They had one son only, who was only 3 years old. They had a second child a year later. But, the husband was a wild guy. Enjoyed partying with his buddies and going out every weekend. She on the other hand was a more homely type. She was'nt the most polite of people, but greeted when...
FetishI left Home at 18 but whilst I was living at home we had an incredibly attractive neighbour called Mrs Stevens and she lived at the back of our house, our gardens backed into each other and my bedroom was situated looking into her garden and was opposite her bedroom.I used to masterbate a lot and I often used my imagination as the internet was so slow back then.Mrs Stevens used to walk around her house at night sometimes not wearing too many clothes and now and again I’d see her pop into her...
Sarita hesitating removed her old blouse and was now in her bra exposing some amount of her boobs. I was pretty excited. Lata remarked, "Oh, you have not nice boobs, you need not feel shy in exposing it in front of both of us. I shall be glad if would remove your bra also before trying on the new blouse." I was shocked; I could not believe my luck; I hoped Sarita would do as requested by my mami. Sarita said, "Nothing doing; how can I expose myself in front of this boy;it is all right...
A good few years ago I lived in a little flat in the suburbs. It was a small, two-story block, with only 6 residences and a little parking area with garages out the back. I was living there with my girlfriend at he time, a dark haired, B-cupped woman with whom I argued incessantly.Often, on my way out to work in the mornings I would pass one of the neighbours, a woman of about thirty with shoulder length, mousey hair cut into a neat sort-of bob. Her eyes were amazing. The little laugh lines at...
Hi all ISS members and sex story readers. I am Jayanth from Bangalore writing this sex story for the first time since I became member of pride ISS club (). This is my true story written without hiding anything from my heart except the real names of us. Please read this story and send your sincere comments to enable me send some more real stories happened in my life. I am basically an engineer working in some reputed private organisation in Bangalore. I am married to mirmala in 1991 to a bsc...
THE NEIGHBOUR Joanne Pare At the age of 18, I spent the summer at my parent's country chalet. Our neighbour had promise them that he would keep an eye on me. He lived there year round and was always alone. Our family came on the week-ends and I would be alone during the week. Andr?, the neighbour, would often come for supper with us and he proposed to my parents to take me for three days on a canoe trip. Since they had known him for years, they accepted. Our trop was planned for M...
I giggled into my scarf so as to muffle the sound. The faint scent of brandy and rum assulted my nose as my breath caught in my scarf's blue silken folds. Attempting to tiptoe lightly to my appartment door, I stumbled into a thin side table which thanks to my imbalance slammed against the radiator, sending in turn a deep metallic bang through the buildings heating system."Right you little cunt, 19 is old enough to have gained respect for elders..." I heard Mr Linton mutter as the door...
Introduction: When I was a teenager living at home with my parents house I was increasingly attracted to our next door neighbour Christine during my teenage years. Unfortunately the following story is only a fantasy as much as I would wish otherwise… When I was a teenager living at home with my parents house I was increasingly attracted to our next door neighbour Christine during my teenage years. Unfortunately the following story is only a fantasy as much as I would wish otherwise… My parents...
I live in a quiet neighbourhood. My house is surrounded by grass for the most part, but quite a lot of vegetation is present on the edges of the garden, so I'm completely shielded from the street. The only place from where people can have a look at me is when I'm sitting in the garden, from a window on the upper level of my neighbour's house. The same goes for my neighbour's garden and boy, I've been peeking a lot at that garden since I moved to this area... My neighbour Doe is a rather small...
MatureJenny was thrown when she heard the doorbell, opened the front door, and saw her neighbour’s twenty-two-year-old daughter, Samantha, standing there. She smiled uneasily as she had just this moment come back downstairs after masturbating on her bed. The thing was that she had been fantasising about Samantha. Jenny was thirty-seven-years -old but was so taken by Samantha. “Hi Samantha,” Jenny managed to say looking her up and down. She looked so gorgeous in her pink cropped vest top showing off...
SpankingMy neighbour is in his 70's but a fit old chap he's very friendly to both myself and my wife, his wife died about 6 years ago and as far as i'm aware he doesnt have any lady callers.His bedroom is the other side of our bedroom wall so i would imagine he has heard us fucking a number of times as my wife isnt the quietest when she is in the zone.Let me set the scene we had been out for a number of drinks at out local so she was not dressed up just jeans and a blouse i wasnt even sure if she had...
TO CANE A NEIGHBOUR he was born in 1957 and over the years developed an interest (perhaps an obsession) with spanking and especially caning since way back, in fact he said; “I guess the first time I can definitely attach a date to this ‘obsession’ was 1967. My elder sister (6 years older than me, she in the seniors and me in the juniors) went to the same school and at the end of one lunch break I saw my sister’s best friend, Sandra Fletcher, standing outside the Headmaster’s study sobbing...