Shemales Porn Stories Page 66
I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.
I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.
I took a shower and completely shaved... Continue»
My boss had sent me to Brighton at short notice as she decided at the last minute that she didn’t want to go. Apparently she had something better to do. The fact that it was my birthday didn’t seem to bother her too much. I usually liked the chance to get away for a couple of days as I’d sneak in some of the wife’s sexier things in my bags and spend my evenings in my room all dressed up and nowhere to go. But this time I would be missing out on spending quality time with Suzy. We’d only been married three years so we still made the effort when it came to birthdays. I had thought of bringing Su... Continue»
The Story of Sissy Slut Amanda
This is a story of fiction
Part 1: The Beginning
When I was twenty-three I meet my Sissy Slut Amanda for the first time. Now he was only eleven at the time and it would be many years before I would know him as Sissy Slut Amanda, but still funny to look back at now. The first time I met my future sissy slut, he was Mark, son of the woman I was dating. He seemed like a nice k**, very shy and timid but sweet nonetheless. It’s wasn’t too long after our first meeting that I would be asking his mother to marry me. We had a good marriage and although I nev... Continue»
There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends.
I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town,
dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?
It had all started a few months ago. I was locked out of my house in the pouring rain,
and I went over to our neighbor’s to see if I could hang out with him until my parents got home.
He was a cool guy... Continue»
I met Gina at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to find such a babe here and she likes ... Continue»
when I started crossdressing,I was bout 15,a few later I got my own place,and was able to do more,except getting in clubs.I was 19yrs old when I got my first appartment,and was not able to get in,cause at the time,the drinking age was 21.and the club,Call club park avenue,hottest gay cub in town,well it was the only one.well I would crise the park where the club was,which was uptown in a very nice setting.so on fridays,and sats nights,I drive around the park looking for hot guys to have sex withI would all way wear a short sexy skirt,and a low cut top,under that a bra,panties,matching gartbel... Continue»
My eyes open with the gentle humming of my small alarm clock. I quickly shut it off so as not to disturb anyone else in the room. Its 4:30am, well before light creeps into the day and the room is now pitch black. Very quietly I rise up on my hands and knees and crawl off of the small doggy bed on the floor next to the big bed. It‘s embroidered with my name “Heather” in pink because it’s my bed and I’m the pet of my Mistress.
I’m silent when I move because I have done this so many times before. On all fours I make my way to the master bathroom and gently close the door behind me. I then st... Continue»
it hurt so bad but felt so damn good. I told her just to stay still so I can get use to it. get use to having a cock in my ass. that was a totally new feeling. it was something I always wanted to try. now I was.
she slowly started to move back & forth. not really pulling out, just enough to make me feel better about it. she was stroking my cock, which was rock hard. I could feel her balls on my ass. deep down i was freaking out. this is really happening. I knew that coming here I was going to fuck some ass. not get my ass fucked.
eventually, I got use to her cock in my ass & she was pu... Continue»
I wrote this last Christmas Eve and sent out to friends who've provided me their email. I tried to include the photo that was the inspiration but couldn't get it to show ... it was stellar! So enjoy ...
"Oh Michael, you're company's holiday party is always so boring! Do we really have to go?"
"You know Courtney that I am expected to be there. I AM the Senior Vice President, after all."
Michael wore his typical grey business suit with a festive tie to the event. Courtney, a tall, shoulder-length blonde, wore a black mesh dress with black stockings and boots. The party was held ... Continue»
Dressed with my red 17cm boots, fishnet stockings, transparent skirt and transparent top I was waiting at the bus-stop to go back to my hotel in Barcelona, but suddenly a car behind be honked.
A beautiful Spanish guy stopped and looked at me, he couldn’t leave his eyes from my beautiful huge tits under the shirt. He whispered into my ear, “Need a ride?” I wasn't even startled and thought if this guy would have a nice cock as his body it would be a good start for the night…. I said “Sure, let's go.”
I saw tha... Continue»
My friend that you all see fucking me and me sucking his big cock in my pics and videos. We will just call him Mister. Well he came over this morning for some Sunday fun. He is so good to me he really knows how to make me feel like his girlfriend. Today was so yummy I am still sexually excited just thinking about it.
I was dressed and ready for him when he arrived. I was wearing my sexy white lace halter top and black thigh high stockings, with the cutest little white G String with a sexy little flower in the back. Topped off with my silver jewelry and 6 inch black heels. I was so excited to... Continue»
As long as I can remember I have had a penchant for wearing nylons and lingerie: pantyhose; stockings; silk, satin or nylon panties (not those horrible cotton things or G-strings that are like candyfloss in your arse crack -- I mean, full cut panties, cami-knickers, or boy leg panties); garter-belts; slips -- both half and full; basques and corsets.............I can go on but you get the picture.
I also have a fetish for high heel shoes: sandals, pumps, courts, stiletto heels, kitten heels, stacked heels, Cuban heels, platforms, open-toe, "Pilipino bar girl fuck-me shoes"; you name the hig... Continue»
Becoming a Bitch
It was supposed to be simple. A blind date, set up online. A hot chick. Me getting laid for the first time
in a while. You know. Simple. And that's what actually happened. Sort of.
I get to the bar, I see Meghan across the way, sitting pretty in a short black dress, legs crossed,
sipping on a martini like she's sucking my cock already. Far as I'm concerned, I'm as good as fucked,
the way she's making herself out to be: smooth thighs, big, round tits, lips that could blow the cap off
a bottle of Bud, legs long as tomorrow and an ass as big as today. Fuck, I feel I'm in th... Continue»
"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an hour see you." She hung up.
The phone call made me really nervous.I had reasons to get nervous if not get a nervous break down. Tara and her husband owns a few restaurants in different cities across the States. I have known Tara since 6 months now since she busted me from one of the restrooms of her restaurants. Well wh... Continue»
This isn't a 'story' at all, in the sense that it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.
There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.
OK, about 10 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale is a casual term for transsexual men, that is, they were born with a male body, male genitals, but for whatever reason, don't want to live as men. Today,... Continue»
I walked into the booth excited to use my new toy, while dressed in garters and sexy panties under my loose fitting jeans. I had just purchased a lovely new butt plug and could not wait to try it out on my pretend pussy.
Taking my jeans down I deposited a token into the slot and got out my lube and started pretending my tight boi pussy was that of the woman on the screen masturbating. I commenced rubbing the oily lube all over the rather large plug, while running my free hand all over my stockings and sheer back see through black panties.
I started sitting down on the plug, and gently ea... Continue»
Fulfilling my babys fantacy
You and I have been having trouble letting each other know what our fantasy's are.
You finally told me about your transsexual interests thinking that I would think your weird.
But was happily surprised that I fully supported you.
We had been chatting with fairdesire for a few months and I wanted soo badly for you to fulfill your fantasy.
I seen several raffles for to win trips over seas and bought several.
I WON THREE !!!!!
Oh my goodness, I had a hard time keeping my mouth shut about winning 3.
I only told you about 1.
And sent on... Continue»
First of all I would like to apologize for my English.
Hello there! I live in a small country's biggest city and here people are strange. If they are crossdressers, shemales, trannies, tgirls, gurls (actually we have only 2 words for a shemale, so I don't know which one is NOT offending please excuse me I do not want to offend you or what so ever) usually do everything for money, or they lack good health, hygiene or I haven't met the right one. This is was a bit new for me. I've always wanted to date a gurl. Not just the sex part, but actually get to know the person, to fall in love and thin... Continue»
WARNING: This fictional story contains graphic sexual/profane terms and scenes. This is a work of fiction, a fantasy, and is meant to be enjoyed by horny fucking perverts like myself.
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning...
It was summer time. As always I spent my summers hanging out and occasionally mowing neighbors lawns for some extra cash. Although I wasn't exactly th... Continue»
The other day i went shopping for a sexy fetish outfit for a fancy dress party , the theme was doctors and nurses so i decided to suprise everyone at the party and turn up in a naught nurse outfit with platform heels . Looking online i found a sex shop that had the outfit that was going to blow every girl away at the party. It was red and white extremly short and tight , they also had all yhe accesories to go with it . When i got to the shop there was this big fit and very hot black guy w... Continue»