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True story, Some few years ago in the mid August my wife was taken to work by me. I returned home and started to change in to some nice feminine clothing (a black nylon body with a nice sheer nylon bra under, and garter belt and black sheer nylons. My short dark grey skirt and my black nylon/microfibre topp and on my feet I had my 8cm high heels pumps) I put my slacks and thin jacket on topp and went out to the car where I removed my slacks and jacket. I took off to a sex shop 30km away. Upon arrival didn't try to hide anything and went in to the shop and started to look around. The lady (owne… Read more

The next week my uncle continued to take pic's but now of me sucking him and him fucking me. He also got me some more makeup and to my surprise showed me how to apply it. My eyelashes were longer and my eyeshadow was very pretty and my cheeks were red. The next day he told me to get ready again because we were going out. So I put on my sexy clothes and applied my make up (I knew how now) he looked at me and gave me a kiss on the cheek. We got in his car and we drove to a motel next to the highway. He got out and I guess got a room. When we got into the room he also had some wine coolers for me… Read more

The next morning my uncle went shopping and he said he was going to get me a present. I was kind of excited by it but I was sore from yesterday. He was gone a couple of hours and when he came back I saw he had some bags from a department store near by. He went into his room and a few minutes later asked me to come in. Laid out on the bed was a very lacey bra matched panties a garter belt tan stockings and heels. Now I do have to admit I had went into my moms panty drawer and tried on some of her panties which was very exciting to me but seeing all this laid out for me was mind blowing. He help… Read more

I was twelve years old and it was the beginning of summer. My uncle was comming to live with my family (I think he lost his job) As he was moving his stuff into the spare bedroom next to mine I saw that he had a VHS and TV. That was pretty cool back then. Both my mother and father worked during the day so it was just me and my uncle home alone. After the first few day he seem very nice and really paid attention to me which I liked. I was walking by his room and his door was open slightly and I could tell he was watching a video. He saw me walking by and said to come in.... I did..... He was wa… Read more

WHERE IS THE LIMIT ?? We dont know Yet!… Read more

Your little sissy cock aimed at right at your mouth - a dildo fucking your faggot ass - this is the only way you get to cum from now on sissy. I'm going to train you into becoming a sperm-addicted cumslut. You'll dress like a slut, you'll jerk-off like a slut, you'll cum like a slut and then you'll drink every drop - just like a fucking slut! I'm going to O-gag your mouth wide open so we get as much of your beta-sperm down your throat as possible. I'll get you all dressed up to look like a slutty little missy - bra and panties, stockings and heels. I'll get you to plaster your face with trash… Read more

So how did you become a gurl? That's the question almost everyone I meet or chat with asks me... how did you become such a sexy transvestite, when did you figure it out, when did you learn you liked cock. I actually love the question, because it turns me on to answer it. When I was 15 or 16 I used to sneak into my parents room, find my dad's stash of Playboys and jack off to them. The girls were sooooo beautiful, I just couldn't believe it. I wanted to see and touch one, which led -- I guess this is common among us gurls -- to digging into my Mom's stuff. When I was left alone I would put… Read more

I am still not sure why I put on a pair of my wife's knickers when I had not crossdressed for such a long time, but I enjoyed it very much. After being married so many years our sex life had faded away. I had always looked at pornography throughout our marriage, firstly men's magazines and then on the internet. I liked wearing the knickers a lot but I felt uncomfortable about wearing my wife's. So I bought some of my own and kept them hidden from her. I bought tights as well and stockings and suspender belts. Then I bought a dress on eBay in an auction. It was a teal colour and was clingy and… Read more

I was usually very careful about hiding my crossdressing clothes from my wife but I got careless. One day I put a pair of knickers in the laundry basket instead of washing them myself. I found them in my normal underwear drawer. My wife had washed them and put them way for me. It was obvious that she knew they were mine. I could have pretended that it hadn't happened, but I decided to talk to her about it. That evening I thanked her for washing my knickers. She looked at me and smiled. I told her that I liked crossdressing, that I found it relaxing. I told her that I still loved her very much… Read more

When I was young I went to a village school. I idolised my first teacher. Let's call her Jayne Carstairs which is similar to her real name. She was blonde and pretty. I suppose she was in her late thirties. By chance I met an old friend last year and we sat and chatted in a pub over a few drinks. I happened to mention the teacher. "Did you know she was the village slut?" he laughed. I thought he was joking at first but he told me it was quite true and it was well known in the village. She had an affair with the shopkeeper although he was old enough to be her father. She often went to see hi… Read more

After the agreement I made with my wife I soon arranged to meet with a man I had been chatting with that I met here on xhamster. We arranged to meet at a supermarket café. I wasn't cross-dressed but I was wearing tights and knickers under my jeans. We got on well and agreed to meet for sex at his house the next day. As we were leaving he suggested I follow him in my car. He drove out of the car park and to a disused cinema just across the way. I followed him down a quiet side road and we parked there. He got out of his car and sat in my passenger seat. He asked if I wanted to suck his cock… Read more

I am a slutty whore in my 50s, and I am so in love with black men. It wasn't until 12 years ago that I realised this truth. Consider this my confession, if you must. I’ve had the idea of writing one for months, but too many things kept consuming my attention. I’m referring to the number of black men I’ve been servicing lately. I’m not a prostitute, nor am I a call girl; I love to fuck black men, and they love fucking my asshole and pussy. It is my choice of wanting to give back what has been denied them for hundreds of years. This is my Reparations that I am committed to achieving. I know… Read more

After that first night I was so sore and satisfied, we continued with our strapon play doing it in every possible position: standing up, doggy, missionary, and sideways. She was really into it and loved talking raunchy. Then she stopped using the strapon altogether and shortly after that we stopped having sex for a couple of weeks. I was getting nervous that she might be having second thoughts about the direction our sex life took. A few more days passed and I decided to bring up the subject. “Honey is something wrong?” I asked. “No, why what’s up?” she replied. “Well … it’s just that w… Read more

I started crossdressing at quite an early age, 'borrowing' items of my mum's underwear and furtively dressing in them when she was at work. I used to love wearing her tights, the sexy feel of them encasing my legs and cock, and the way they made me feel so girly when I admired my reflection in the long mirror in our hallway. I would also wear her big full-cut knickers and doreen bra, and complete this with a lace slip and a pair of strappy heels or mule slippers that I could fit into then. I used to get so turned on that I would come in my tights without even touching myself, and I would stay… Read more

Let me first say Im a dirty old man. I first discovered the pleasure of sex when I was 12. My friend Pete and I shared mutual jerk off and cocksucking sessions. It is 1957 and this was definitely taboo so we were careful about where and when we had our sessions, still we got busted by his dad when we were 14 . Pete got shipped off to his grandparents for a few weeks and I figured his dad was going to tell my parents about our sexual escapades. Boy was I in for a surprise. He called me to his house and when I got there he opened the door, was standing behind it, all I could see was his face. I… Read more

I checked the time and looked outside, deciding if i should got to my favourite bar. I checked my wardrobe deciding on a high neck satin blouse in black with a sheer black body stocking and open crotch girdle with 12 strap deep suspender belt gios seamed nylons and strappy heavy open toe patent leather heels. Finishing it off with a very short shiny pvc mini skirt. i applied a light foundation with dark eye liner silver eye shadow and deep red lipstick with a cherry lip gloss . A long blond bob wig. and my fav BBC earrings and ankle chain. i quickly checked my look in the dressing table mirror… Read more

Oh my it's the masked mad doctor he's going to give me a physical to make sure everything works great. He started out by slowly using his finger he asked me to squeeze his finger with my anal muscle to see how hard I could squeeze his finger. OH he's putting in more fingers to make sure my muscles are in great shape. OH fuck he put his whole hand inside of me shit he's fucking my sissy/pussy slow and deep! He told me everything works great and he needs to check my pussy lips now to see how sensitive they are. First though he strapped me to his bondage bench put straps across my tummy and under… Read more

Oh my! Had the greatest anal fuck session ever in a long while. It started out waking up in a slightly good mood. Did the typical. You know, shit, shower, and shave? Got dressed. Prepared my coffee, and on my way to work, that's when it hit me. Ugh!, and I mean that in a good way, I felt my trousers begin to tighten up. Oh yes. Getting hot and bothered. From what? I don't know yet. Sitting in my vehicle in the parking lot I hesitated to get down, until my engorged cock began to recede, and not be the center of attention. Trying not to look so suspicious I walked in like normal putting all t… Read more

My given name is Joseph Jutras, I am a sissy slut. My chosen name is Ashley Jolene. I have been a sissy all my life. I no longer care who knows. I tried to be a man and was a complete failure. trying to have relationships with women never felt right. even at a young age I toyed my ass while masturbating and love to wear woman's clothes. eventually i found a woman that embraced my sissyness and did my make up and dressed me sexy and fucked me with her strap on regularly. And I was happy for a while. Earlier relationships taught me that i could never be a real man. my so-called cock was less th… Read more

A few years back I met C on a job site, She was hired by my company to come in and analyze the ground we we're working on. One thing led to another and I ended up getting her phone number, we texted back and forth for about a week until I asked her out for a drink one Friday afternoon. We made arrangements to meet at bar downtown at 730. We had a few drinks she asked if id like to join her outside for a smoke, so I did I kept her company we chatted some more and went back inside and had a few more drinks and before we knew it, it was 11 o'clock. She said she needed to get back home so I picked… Read more

I've always had a big cock. I was around 11 years old, the first time I knew I had a large cock. I was playing in my mom's friend Sandra' pool with her daughter Vicky,(about a year and a half younger than me) and her son Damon, ( my age). When Damon went in to get a snack for us, Vicky and I were horsing around at the shallow end and I started to get an erection, I didn't really think about it as I climbed out to jump off the diving board, but Sandra did. She asked me to come over. She said " are you ok honey?". I said yes why? She said, " well you seem excited", as she gently flicked the head… Read more

I was just looking at pictures of sexy matures, when I happened on this picture and was instantly taken back 42 years. I was in the summer of my 13th year and on Thursdays, I had to collect for my paper route. I Rang the door of Mr.and Mrs. Abrhamson, when she opened the door, just like the woman pictured here. I must have made an audible gasp, and caught her smile at me. She invited me in, while she got my money. I could feel myself getting a bone and she noticed right away. She handed me the envelope and brushed the growing bulge in my shorts, with a slow hand. She said see you next week, as… Read more

I was in his apartment. He was older than me by a few years and I suspected he was at least bi-sexual but he was a nice guy and it was just to watch the game on his big-screen, so no big deal. Had a few beers and the game ended. "Feel like watching a dirty movie?" "OK, sure. " I was pretty comfortable but I'd only watched a porno with other guys once, at a stag party when there loads of other people there. The conversation then was bravado and bluster. This would be different. More different than I realized when the movie turned out to be all-male. "Do you mind?" "It's not what I usuall… Read more

I became carol as my wife wanted a female friend. She knew I was Interested as left the house and I could feel a bra he was wearing.in bed we would watch porn and I love the blacks fucing and he loved tyranny girls. I started leaving soiled panties in te\he bath room. I knew he was sniffing and wearing them and he thought when the were washed no evidence. We went shopping and I picked out panties and bras.I asked for his help and he helped with the bra. He said it didn’t fit and I said I guessed it was his size. Embarrassed he let me put the bra and red matching panties.I said your so fem and… Read more

So one snowy Saturday last month I was hosting a wedding at work and I was making my way through the hall checking on things and a pretty woman Ana around my age stopped me and said that's a beautiful Louie ( Louis Vuitton ) dress I said well thank you , she had a good eye, she said size 8? I said yes but my boobs need a size 10, she laughed and said I doubt anyone minds your ample cleavage ,I said you're probably right, she said but I love your Manolo shoes size 7?, most ladies would wear black or silver to match your silver dress, but you chose gold just stunning, I said thank you again and… Read more

I was raised in the 50s My mother's best friend was her younger sister who lived 10mins away, Aunty Martha would walk down to my mother's house and they would sit and chat before they went shopping together. My mother was a plain housewife but Martha was a barmaid and dressed like one with stilettos and jewelry, her hair was set and sometimes tinted pink or lilac, her makeup was heavy and her nails varnished and They would sit in the dining room chatting and Martha would leave lipstick stains on the teacups and cigarette ends. Before they left they would use the toilet and I would hear Martha… Read more