Ashley s Crossdressing Adventures
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Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...
CrossdressingCaught Crossdressing by Aunt Sharon Story by Kresha Matay "I wonder where Brad is? He knows you're coming, you'd think he'd stick around. Oh, I hope he'll turn up soon, otherwise you'll have to drive back in the dark." "Rita, don't worry about the boy so much. Brad is like every other sixteen year old boy. He's probably driving around with his friends looking for girls and forgot I was coming!" "Well, aah, I don't think so!" His mother stumbled to say. "That's something you and I...
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 DresserSometimes I become obsessed with thoughts of all the guys my wife has had sex with before we were married. When that happens, I often get her to jerk me off while telling me a story about someone she has given sexual pleasure to. Recently I became fascinated, fixated thinking about guys creaming on her naked nice-sized tits. Tuesday evening I got her to tell me one of my favorite stories about a guy who tit-fucked her bare boobs in a motel room when she was in college. Her boyfriend’s parents...
Hii, 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...
HumorUp 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...
CrossdressingThis 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...
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...
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...
Do you know a crossdresser who got caught in the act?This is a real life story of a crossdresser caught in the act!This happened around when I was 15 yrs. old.As my sisters were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my...
THE 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...
Before I start the story I want to describe the setting so you get a better idea: it’s a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that’s for sure. The layout of the motel is a rectangle. The rooms surround the rectangle’s perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...
*** Night 1 Friday "You joking!" cried Newlyn. "No, I am not. Some things are not funny," responded Eric, Newlyn's father. Newlyn had just been informed by his father of the accident. The power pole in front of their house had just fallen onto their house. Easy to say Newlyn did not really believe it nor did his sister, Juliana. Apparently a drunk driver had hit the pole and knocked it over. Newlyn's father had just picked them up from school and had finished explaining what...
I couldn’t even tell you how many years it had been since my mouth and tongue had touched a pussy. I hadn’t dated anyone since my divorce three years prior; and as for before that – well, my ex-wife was never much into oral sex even in our early years, and not into any kind of sex toward the end. If I got to stick my cock inside her now and then, I counted myself lucky – never mind any of the frills.In all that time, though, I’d had hundreds of fantasies about kissing and licking, fingering and...
Oral SexI'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...
*** Motel Week Ending 2 "What if you knocked up your sister?" That was the exact thought that had been on Newlyn's mind for the past two weeks. The thought permeated his entire being ever since they had left the motel. The family had been forced to into a motel for a week while the house was under repair. It was during this week Newlyn had shared a bed with his younger sister Juliana. It started as an accident and seriously bad judgment on his part that had then cascaded into the...
Motel Pool by SpectreOfHell Part 3 of 3 John was visibly shaking as he pulled his car into the parking lot of the Timmonsville Motor Lodge. He was ten miles from home. Timmonsville was just a hole in the road, an abandoned mill town with a single gas station and one run down motel being the only two businesses around. Teens kept the motel in business renting rooms by the hour. When John told the clerk he needed one for a couple of days, the old man raised one eyebrow but didn’t comment. Ten...
I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already. I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm. I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair...
As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in a long time, I start to feel fearless. Being fearless is one thing, but making sure we look hot is...
CrossdressingAt this point I have been crossdressing for many years. I started out with my mother’s panties and bras. I would wait till she had gone to work and then go to her room and pick out one of my favorite matching bra and panties. I would lay on her bed and stroke my cock though the soft silky material, dreaming of her walking in and catching me and telling me what a little faggot I am. It never took me long to cum. This fantasy never came to be, but wanting to get caught stayed with me.A few years...
During my second year in college I was in between girlfriends and at the time I was greatly indulging in my crossdressing fantasies. I spent a lot of time in lingerie sections of stores buying bargain panties and bras since that is all that I could afford. The pickings were fairly slim for a big guy, so I developed a love of granny panties because those are so easy to find at a store like Walmart or Target. Craig's List and similar websites did not yet exist at this time (including Fet-Life)...
JOANNE SLAM - A LIFETIME OF CROSSDRESSING…..Almost!!!I have been doing this for a long time, cross dressing and my wanton ways with my transvestite fetish, my feelings of bi-sexuality and the thoughts of being “The Nasty Looking Slut” when I would look at porn magazines. This was in the late 60s and early 70’s mind you so I was seeing very cool, I thought anyway, looking back now it was that vintage lingerie and under-garments style and as a teenager it was most likely finding these kinds of...
I started with crossdressing a few month ago, first just panties or strings when i had a wank over videos and pics of other crossdresser getting taken or dominant trannies and women humping devot men.By now i wear black stockings and suspender belt, a white lace string, black shiny mini skirt, white blouse, 4" black heels and a blonde wig.I also had an extreme urge in me to feel a real cock in my arse, to satisfy these needs i began to visit adult cinemas in my area, first just with stockings...
Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She told me she’s looking for a slave to entertain “them”Thought it was a spelling mistake (since it was german its not really much of a difference)So i agreed...
crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs and heels. it started when I was younger but evolved as I got older, now as I got older ive refined my skills and abilities and can pass as a girl when dressed. I had fooled around with guys before but I had never dressed for one only indulging in self pleasure with toys and my fingers. when I got off work on friday I was excited for the up coming three day weekend going home to get dressed up maybe go...
This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be therei did think it would be nice to have it up here as well though :)Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She...
Hello indian sex stories dot net friends , my name is preeti(fake name) age 20. Ye baat kafi purani hai lagbhag 3 saal pehle ki . Mai ek part time crossdresser tha aur mujhe meri chachi bahut pasand thi aur hain . To mai jab vo aur ya koi b ghar pe nahi hota tha to mai unke room mai jake unke innerwear pehnta tha . Aur jaise ki mujhe bondage bahut pasand hai to chachi ke kapde pehnke self bondage karta tha jab ghar pe koi ni hota tha . Isi tarah ek din ghar pe koi ni tha aur mai chachi k room...
CROSSDRESSING CHARLIE Episode 11 UNDER HIS THUMB Prue watched him get into the car from the top of the steps. Dave, who was still standing outside of his car, stared at Prue maliciously. She returned the gesture, glaring intently with apprehension before watching him swing into the car. Dave was quieter than usual as he settled himself at the wheel. He looked unnerved, doubtful, and even a little irritated. He turned the key in the ignition and the engine revved up like a vicious...
I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my ex boyfriend. It started one afternoon when he came back from playing basketball. I had just finished...
CrossdressingTo tell you the truth, she wasn’t much to look at. But then, neither am I.Don’t get me wrong, she wasn’t scream and run away ugly, she just wasn’t the kind you would look at twice. Or even once. That’s the way it is with motel maids, few actually look at them.I was stuck in a motel in South Carolina after my car broke down on the Interstate. BMW parts for older models are scarce and expensive, and I had to wait while the part came in from some place far away. Probably Tibet. It was hot and...
*** "...of the total number of baryons predicted by Big Bang nucleosynthesis, as inferred from density fluctuations..." there was a knock at the door. Newlyn had been studding again. He did this when ever he could. It started about eighteen years ago as a cooping technique to deal with the pain of his greatest regret. As part of this he had next to no social life so, the knock at the door was a surprise to him. The only time any one ever knocked on his door was for mail but, Newlyn could...
Motel Pool by SpectreOfHell Part 1 of 3 John slipped into the cool water of the motel pool with a sigh of relief. It had been a long, hot day, and he was glad to be done with it. Tomorrow he would be on the road again, making the long drive back home where he could report to his wife that their business would survive another year. The sales he had made at this year’s convention exceeded expectations. Hell, he might even be able to afford that divorce now. He dove under the water, relishing...
I could feel everyone's eyes on me as I stood outside the motel room door, As per our chat a few days prior, we agreed on a few specific facts before I ever arrived at the motel room.****1) It was undeniable that I was a cock-addicted, cum-hungry sissy faggot that needed to be used and abused by men. It was a universal constant that I couldn't ignore, 2) Once I stepped into the motel room, I would be acknowledging the aforementioned facts, and the understanding that a sissy faggot cannot be...
My heart was racing as I pulled into the parking lot of the motel off Route 25.The location of the motel would make one feel as though it would be the kind of place that would be desolate and run down, but apparently it was quite popular. I hadn't expected to see so many vehicles parked in the lot of the place; many with people still sitting in them looking at their phones, or just watching people come and go. I was going to have to get out of my car, and they were all going to see me.The fact...
My lovely new Malaysian friend emerged from the bathroom, moving shyly in the low light. He was wearing thigh-high stockings, cute little panties and a matching top that was tied at the front.My heart leaped at this gorgeous sight. He had advertised that he wanted to hook up with someone who appreciated fembois, and I was very eager to indulge his fantasies and mine!We had agreed that we were going to enjoy a girl's night together, and so he started playing some lesbian porn on his computer....
CrossdressingFriday came and I'd bought a new outfit just for the occasion. I slipped into my low rise boy shorts (black with white spots and white lacing), tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my C cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd...
I 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...
All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't your thing but you have ideas, send me a message. I'd love to hear of anything you come up with.
TranssexualThe act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...
Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the hotel, before you run dry,” I said. But that didn’t seem to deter their enthusiasm, until Susan walked up. “I’m done...
CrossdressingAfter Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls under my panties.” Jackie interrupted with, “Forget about the dance floor, tell us what happened in the...
CrossdressingIn Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’. As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman....
CrossdressingIt was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious...
Crossdressing“Mikki?” Caz asked. “Yeah, babe?” “I’ve been thinking...” “Always a dangerous thing,” I said, cheekily. “Yeah, whatever. Seriously, I’ve been thinking about what happens next.” “What do you mean, what happens next?” “Well, you are really beautiful but I was thinking of stepping it up a notch.” My wife Caz is the most beautiful woman I know. I love her with all my heart. She is sexually voracious. We played a little game a while ago. She saw how turned on I got when she treated me like a bitch...
CrossdressingCaz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was making record profits and she had already had a pay rise. She was also in line to get a huge bonus at the end of...
CrossdressingI was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover. I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She was finishing her degree in International Finance. She was the most beautiful woman I had seen and I thought I had...
CrossdressingAs I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...
CrossdressingSo as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...
CrossdressingHello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...
***A crossdressing story***(All characters are fictitious...maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her...
My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please.Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land Steve has that he'd keep a couple of horses to ride but no. The barn is filled with cats that curl up and sleep...
CrossdressingMother and Crossdressing Son FantasyThe story is about how my passion for wearing women's lingerie helped me to establish a more intimate relationship with my mother.I'm a 42-year-old man and I still live at home with my mother. My Father passed away 20 years ago. We live in a suburban bungalow and I have a nice little apartment in the basement. It's not as private as I would like. That's important because four years ago after discovering a number of chat sites where men present themselves in...