Shemales Porn Stories Page 59
A Day at the Beach
I lay face down on my towel, basking in the sun, almost falling asl**p. My boyfriend Jake, he would be my husband if it were legal where we live, walked up and sat next to me. He gently stroked my left arm, "The water is great, Loren. You should try it."
Without opening my eyes, I turned my head towards him, "I think I'd rather just lay here in the sun."
He started rubbing my shoulder a little harder, "Come on, sl**py head. Get up."
"Stop it Jake!"
He gave me a quick kiss on the cheek then he whispered in to my ear, "Or, would you like me to ma... Continue»
On my 18th birthday, I had a job interview with a local e****t service. It was actually my 16th birthday but I had managed to get a fake ID ;-) I had a female cousin that was e****ting for this service and when she told them that she had a crossdressing bisexual male cousin, they wanted to meet me!
I showed up to the interview completely in drag: black stockings, garter belt, stiletto heels, black miniskirt, red blouse, wig, face painted like a fucking whore! It wasn't long into the interview when I was informed that the job would involve getting naked with mostly male clients and asked ... Continue»
Since my roommate has moved out Ive taken it upon myself to begin exploring my Transgender tendencies. I shaved my legs, cock, chest everything. As I walked through work the first day, just feeling my jeans against my smooth shaven skin was a huge turn on, I felt my little sissy clit getting harder and harder as the day went on, tugging my panties tighter and tighter against my little bitty pussy ass, as they get stretched out. Its so erotic knowing that I am such a slut, that underneath my dirty grungy work clothes is a sexy soft girly sissy begging to be abused by cocks. mmmm. Spending all d... Continue»
I had been a submissive with ever more disgusting fantasises for several years now and had acted out a fair few of them over that time.
I was a manly, muscular lad who everyone looked up to and would think was the textbook "normal man".
I held a professional job, steady girlfriend and a good standard of living, to the outside world, the perfect existence.
Behind closed doors i had harboured a strong, submissive streak which i could simply never satisfy and a desire to be controlled and humiliated that just grew day by day.
I love to serve Dominant women and adore total degradation, shame ... Continue»
A couple of weeks ago my wife hosted an Ann Summers party. I had hoped to sneak away for the evening as, though I would have been more than interested in the lingerie on display, I didn't fancy listening to the constant cackling common to "women only" parties and also the inevitable anti-partner jibes such as: "I ask are you in yet and he says I'm finished", "he picks his nose and farts afterwards" and "you'd think he was rodding a drain the way he goes about it" etc. The wife had other ideas however and I was drafted in to prepare the nibbles, pour the drinks and answer the door, the latt... Continue»
I had been dressing for a while but kept it very secret. I am a 5’11, 175 lb gurl who feels very sexy when I was dressed up. When I was alone in my dorm room I would put on sexy little outfits, make-up, and a wig and play with dildos that I had hidden in my dresser. No one in the dorm knew that I dressed up. I tried to keep it very secret. It was hard to do. I was on an all-male floor with a communal shower. There would sometimes be 5 or 6 guys showering at the same time. I would try to keep my excitement from showing and was successful most of the time. It was so hard not to stare at some of ... Continue»
Shemale, tranny or as some like calling them t-girls, I like them. Im not talking cross dressers, I'm talking about the ones with titties, curves and sound like a woman. Being a bi male, to me its the best of both worlds. I like watching porn of them and honestly I prefer the ones of them doing a strip tease, ending with them stroking their cock and cumming all over themselves.
I met one, unknowingly, once while playing around on a chat site. I was cruising thru the members "online" when I came across her profile where she had a good picture of herself. I sent her an Instant message and af... Continue»
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him.
It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willing to do anything."
Now what I had written was the following:
"Young 48 year old, looking for an older man, early to mid sixties, still sexually active willing to be my top. Would love to get together and decide what our roles would be and then keep them going whenever we meet. I am a submissive who lo... Continue»
After lying on the bed for some time enjoying the wonderful ass I had just had she went to refill our drinks. The rum and coke had been flowing at this point and she felt that I was ready for her. As I was lying on the bed I noticed her get on her knees next to and to my surprise her hard cock was now 3 inches from my mouth. She didn't say a word, she just began to tease my lips with it. Having not had a cock in my mouth before, I was unsure what to do although heated in the moment I gave it my best.
I took her hard cock in my mouth and began to suck it while stroking it. From what I c... Continue»
I was about 15 when i found a bounty of porn magazines and female lingerie in the park near my parents house. Without thinking at all i grabbed it and took it home. that night after getting horny reading some of the porn magazines I tried on some of the stockings and silky lingerie. it was the sexiest feeling i had ever felt. they seemed like a natural fit for me, as i had a slim and somewhat girlish figure.
Over the next few months i regularly played with myself while dressed up and reading the mags. but after a while, without the magazines, imagining I was a girl, with my legs spread wi... Continue»
However, Nancy’s stay with us that summer was going to prove even more eventful than ever I could have imagined. Even after having been caught wearing her things by the neighbour’s son, Lesley, which led to a whole new dimension in our friendship, as you’ll know if you’ve read “Caught in the Act…”
Once again I found myself alone in the house. Dad was at work and Mom had gone to her Bridge Club and wouldn’t be back for ages. As you’ll know if you’ve read “Caught in the Act…” Nancy was really hot stuff and didn’t care who knew it. At 18 she’s a couple of years older than me, in the full bloom... Continue»
This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and opened my pants. She pulled out my cock and began to suck it really good. She was licking my balls, ... Continue»
It was about an hour after dawn on the third day of our Mediterranean cruise. I’d left my wife Melissa, asl**p with our neighbour Roger in his cabin. We’d spent the previous day fucking with Roger in the ship’s sauna and in his port-side cabin. I awoke to watch Roger and Mel making love, but once they went back to sl**p I was wide awake and slipped out to go for a swim.
I had swum about half a mile and was looking forward to the rest of the day as I walked back to our cabin. When I got there, our Brazilian maid, Maria, approached me looking concerned.
“Meester Jac... Continue»
I had been curious and excited about being with a ts girl for a long time. So when I was in a hotel in another city while traveling for work, I searched craigslist. I posted an ad and received a 6 or 7 responses. One girl made me very excited and seemed like a nice and real person. She was slim and feminine and 30 years old. She was very pretty in her pics. I sent a message to her and wondered if I would hear back from her. I told her I was a curious guy and what I was hoping to share with a ts girl.
To my surprise she responded within 10 minutes. She told me she liked what I said in my mes... Continue»
I couldn’t believe I was doing this, as I stood by her front door I struggle to find breath on a surprisingly clear day. It had started some months ago, and internet chatroom, boy those things can be dangerous. I had spoke to Mary almost every night, soon chats turned to sex then to fantasies. The difference was she only lived in the next town so when she asked to meet I jumped at the idea, she was so sexy in her pictures. Admittedly Mary was 41 and I was 26, but still. She stood at 5ft10, long straight red hair, a body most twenty one year old girls would be jealous of. Stunning was the word.... Continue»
We live in a very very small town, and now I am the town slut. This is the story of how my obsession with one mans cock turned me into the town slut.
I had been sneaking over to see Phillip every chance I could after he had fucked me and let me suck him. I couldn't get enough of his cock. I tried to see him at least once a week. I would usually blow him, but sometimes he would have the time to fuck me good and hard. I get off work hours before my wife and Phillips wife works later so this gives me time after work to dress up and head over to their house for some sissy fun.
One part... Continue»
I was very surprised when my b*****r-in-law Tom invited me to watch the super bowl with some of his friends. The only reason he would “invite” me over was to be his little sex sissy, since he had enough pictures of me dressed as a girl sucking and being fucked by him I had no choice but to do as told.
This would be different, I thought because his friends would be there and he would never let them know he did any homosexual acts.
When I arrived Tom immediately hustled me into the bedroom. I saw right away the little French maid outfit on the bed and my heart sank. I protested, and said t... Continue»
“God yes,” Lisette moaned as her husband flicked his tongue in and out of her hole. The five-foot-ten-inch brown-skinned beauty grabbed his head with both of her hands and pushed his face deeper into her ass crack. As he made love to her tranny pussy, her body, all one hundred and forty-five pounds of it, squirmed. She wiggled in every direction effectively working the fitted satin sheets off of their California king size bed. Her barely functional clit stiffened. “Fuck me,” she squealed.
Sensing his oral work was finished; Deitrick emerged from her anal cavity and stood on his knees. He ad... Continue»
I asked my 18 year old Asian Boy James if he would consider dressing up for me ? He seemed reluctant at first but the next day he told me he would only wear a little makeup and panties , that was good enough for me cause within 20 minutes I had him bent over and I was licking his tight hole getting it ready for my throbbing cock . My problem with fucking James is that his hole is so tight and warm that I cum almost immediately but I guess that's not much if a problem cause I fuck him multiple times when we're together .
So I'm anxiously wanting for him to dress up for me do we picked a date ... Continue»
When she walked in to the restaurant I knew I was in trouble.
It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.
Convincing she was not, a crossdresser without question. But pretty, really pretty. And the way she walked, shit, I was getting hard just watching her. She wore a tight bla... Continue»