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Shemales Porn Stories

Sissy all dressed up at a rest area

Gay MaleShemalesHardcore

Sissy all dressed up at a rest area So, i had a bit of a scary encounter recently. But it was totally worth it =]. I was driving from my home town to the town where i go to school. It is a windy little road that goes right through a big slice of nowhere, with very minimal cell service. And it was night time. I had been all dressed up and hoping to find someone at a local wildlife area that is an OK place to find guy sometimes, but no dice. I am pretty shy, and don't go to places like that much, i am almost relieved not to have seen or been seen by anyone. It was getting late and i had school… Read more

Posted by sluttami 12 days ago 4 2,393 92%

A conversation


You’re stood in front of me, your 8” heels pushing your calves high, nyloned legs silky, smooth and shiny in front of me. Your cock straining as I work it with my hand and mouth. My cock hard with precum dripping off the swollen end. You rub your cock on my nyloned legs, up over my nipples and towards my mouth. You stand before me with your hard cock looking at me, longing to be kissed, licked and sucked. I take you in my mouth, slowly drawing you in, my fingers wrapped around your hardness, my reds lips sliding over you. I push you back and you lie down, your legs open slightly. I lie down… Read more

Posted by beccy69 12 days ago 1 728 100%

You and me


You’re stood in front of me, your 8” heels pushing your calves high, nyloned legs silky, smooth and shiny in front of me. Your cock straining as I work it with my hand and mouth. My cock hard with precum dripping off the swollen end. You rub your cock on my nyloned legs, up over my nipples and towards my mouth. You stand before me with your hard cock looking at me, longing to be kissed, licked and sucked. I take you in my mouth, slowly drawing you in, my fingers wrapped around your hardness, my reds lips sliding over you. I push you back and you lie down, your legs open slightly. I lie down… Read more

Posted by beccy69 12 days ago 2 684 80%

Tales Of Espermia

ShemalesGroup SexMasturbation

“The Lord Creator looked upon this world and its vast emptiness and it saddened his heart so…“ The Reverend Mistress proudly preached; her loud but soothing voice echoed gracefully off the walls and through the sanctuary hall of the cathedral that stood in the center of the large trading town of Magna Cazzo The Reverend Mistress stood behind the polished wooden alter reciting “The Aria Of Creation” to the crowd of faithful that had arrived in the town of for the Gathering of The Clerics. “So he took his mighty Sacred Phallus and begun to please himself until The Divine Seed spurted from The L… Read more

Posted by Rust1 12 days ago 2 432 100%

Indian CD in small town Hotel.

Gay MaleHardcoreShemales

Hi All, I guess you all know i am bisexual and i love to CD. This is another one of my experiences which happened a week ago, in a small town in Chattisgarh. The nearest flight connect was Raipur so i reached there and my onward journey was by trian so i had a few hours to spare. The trip was for 3 days and I was alone so i went in search of lingerie shop. I found one ( which has become my regular shop since last 3 visits in 3 months, since Raipur being my town of entry for chattisgarh state visits as there is the only airport there and then i take train to various smaller towns.)and bough… Read more

Posted by hornyboyind 12 days ago 895 100%

Me and My Brother

First TimeMasturbationShemales

This is a true story A couple of years ago, when I was still living a home, I was just learning how fun it was to dress up. I was only 15 at the time. I had bought a dress from a charity shop super cheap, some girl’s underwear from a super market, and had “borrowed” my older sisters wig (she had a lot of wigs). One day when I thought the house was empty, I got naked, then put on the underwear (I stuffed my bra with socks), the dress and the wig. I had just put everything on and was checking myself out in the mirror, when I started from hearing noises from the next room. It was my… Read more

Posted by Jane_bae36456 13 days ago 3 3,352 92%

Girlfriend's Sissy Cousin

AnalGay MaleShemales

Jarrod Rodgers didn’t mind that his live-in girlfriend had a relative moving to town. But he did mind that Amber’s cousin had to stay with them for about a month. This meant he could not walk around the house in just his boxer briefs like he usually did. It was a Saturday so he was watching college football. He also had a beer in his hand. Amber walked out of the bedroom and announced she was heading to the bus station to pick up her family member. She left the apartment and started up her black 2015 Ford Focus sedan. Jarrod pulled out his dick as soon as she was gone and flipped on some… Read more

Posted by faggyboi 13 days ago 5 3,591 86%


ShemalesFirst TimeFetish

It was getting late, I turned off the car and stared at the wheel for a while, contemplating my thoughts, I was trying to decide if I should return, but at the same time I felt a fast pulse, the adrenaline was running through my body. When I entered the room, Violet recive me with a kiss on the mouth, and asked me why it took me so long to enter, she told me that she had been watching me from the window for some time but I seemed motionless. I commented that I was a bit nervous about what we were going to do and for that I needed to drink a glass of wine first. She was very relaxed, you co… Read more

Posted by DirtyMarieAnne 14 days ago 5 1,096 88%

taking garys loads

AnalGay MaleShemales

i was 21 when i met gary who i liked to call daddy gary at a porn theater. after hooking up a few times at the theater he gave me his number and told me he would love to have me over his place sometime. turns out he lived pretty close to me, a 10 minute drive. a couple days later i gave him a call. he said he had a few things to do but would be free a little later. he told me that he would pick me up at 4 in front of a fast food place that was a block from my house. at 4 i was where he told me to wait. i had on tight low rise jeans, a pair of tan boots with fuzzy trim and a white hoodie, big… Read more

Posted by cxdboi 16 days ago 2 9,387 100%

Dear Diary _ Prolapse surprise


HI Sweeties (love you all) - If you have read any of my post you would already know that I was gaped and my sissy pussy was wreaked at a young age. If you are not aware send me a message and I will explain how and what happened. Anyway, In my early 20's I was scanning the hook-up sites looking for a stranger who was staying in the area. I came across a trucker whose truck broke down and he was looking for someone like me. We exchanged emails and agreed to meet at his motel. He opened the door and his eyes lite up seeing me. I was dressed in a short brown and yellow plaid mini skirt, tan… Read more

Posted by MichelleSissy14 17 days ago 2 2,220 79%

My TS Girlfriend


I'm bisexual and I love women but I also love cock! I got it in my head that a TS would be the ultimate partner. I'm not "out" and I know where "the clubs" are but have never been. I assumed my task would be daunting, at best. So the hunt for a TS girlfriend took several months and down many an incorrect path! Which I'll skip and get to the good parts. Not all gay bars are crazy disco, drag queen show having chaos. In fact many located in the "gayborhood" (as its affectionately known) are just bars or pubs. I was at one of these in an isolated booth on a weeknight, it's a low key place and i… Read more

Posted by billytheg 17 days ago 2 4,304 97%

Just what the Doctor ordered part 3


Part 3: If you haven’t already, please read “Just what the Doctor ordered” parts 1 and 2 on my home page. It had been several weeks sense my last encounter at the doctors office. The stars and the moons had not aligned to allow me to go back to be serviced again. I’m Trying hard to get used to my caged cock, keeping me from masturbating on an average basis. Funny, when you can’t masturbate, all you can think about is masturbating! The day finally arrived. I get dressed up in a cute black skirt and long sleeve top, bra and panties matching, and a pair of lovely red pate… Read more

Posted by 04ltmwco 18 days ago 1 1,601 91%

Gurl Story – The New Tenant’s Secret

AnalGay MaleShemales

Occasionally in passing you have seen a few different women go in and out my apartment. Today, you had to sign for a FedEx delivery for apartment A12; addressed to Allison. A few minutes ago, you saw a girl bounce up the stairs and enter the apartment, so being a good landlord, you thought you would just go up and drop off the package. You knocked on the door, I forgot to close it all the way, and it slowly creeks open on the first knock. You creep in holding the package asking if there is anyone home, I can’t hear you because the music is blaring my favorite songs getting ready to go out.… Read more

Posted by Browncherrygurl 18 days ago 1 2,969 93%

His first time

First TimeGay MaleShemales

I used to and still do peruse a couple of websites that have chat rooms and IM capabilities geared toward ts/tv and cd chat rooms and have met with several interesting guys and other CD’s thru these sites. I easily get bored having sex with the same guys over and over, so I am always looking for new and exciting hookups. I love to dress up and look and feel sexy and just the same way a woman likes the attention that men give them, I am no different. Being retired allows me more time and freedom to be as sexy and feminine as I like and mostly live as a woman all the time when at home, staying f… Read more

Posted by LisaTn 18 days ago 2 3,290 100%

Taken to Dinner


We met at his place. I’ll refer to him as Mr. X. We’ve met a few times. This time he asked me to dress as a man. Typically he’ll take me out someplace fancy and I’ll be totally passable which makes him super horny. Then we go back to his place where I typically find myself tied up with his evil cock in my mouth then him perving on my feet until he eventually blows his huge load onto them. Which i fucking love. I went as “Troy” his assistant which was our generally agreed-on cover story when I wasn’t dressed as Valerie and as usual under my suit i wore garters, fully fashioned stockings and a… Read more

Posted by subval79 18 days ago 3 1,383 85%

Jenny 1


Jenny 1: It was way back in 1972, I was 18 and my parents had decided to move to Australia. They said the USA was no good any more. Nixon was president and they did not like what was happening. Much like today with our new president. We decided to drive across country to California from our home in Indiana. We packed up and headed west in an old 1965 Dodge pick up and a 1965 Ford van. My three sisters, mom and dad and me. Somewhere in the southwest; I th… Read more

Posted by jennysissycd 18 days ago 5 2,105 89%

Sex with a CD on a boardroom table

AnalGay MaleShemales

Like all of my posts, this is a true story and one of the wildest things I have done when having sex. At the time of this experience, I had been crossdressing in one form or another for 20+ years. I had started off with wearing pantyhose, then slowly moved into lingerie, heels, nylons, and wigs. As my enjoyment of crossdressing expanded I took to quite a few message boards. First to find out what else is out there, but then to make connections. Some connections were for sex, and some for friendships with like minded people. One Fall day I was on Flickr and I ran into another local CD and we… Read more

Posted by cgy_online 19 days ago 12 1,873 89%

First time transvestite dogging

Group SexShemalesMature

I have been cruising since I was a teenager. As I got into my 20's I became more adventurous and began wearing women's underwear underneath my male clothes. Some men I met loved it, others didn't. Online one day I chatted to a transvestite who agreed to meet me fully dressed that evening in a toilet in a country park. I went at the agreed time but to my shame I really did not think it was seriously going to happen. I just could not picture someone taking such a risk with a stranger. When I pulled in there was one car already parked and so I went into the toilet as agreed. It was very dark and… Read more

Posted by TVinBristol 19 days ago 5 2,248 92%

a weekend away

AnalGroup SexShemales

this happened about 20 years ago when i was 19 or 20. at the time i had a couple different boyfriends, one of them was terrence or terry as he was known. terry was in his mid forties, nicely built and had a thick cock that stood close to 10 inches. i've been with countless men over the years, some with huge cocks and terry has to be in the top three if not the biggest. he could fuck too, good and hard for a long time. after terry and i had known each other for a little while he introduced me to his 29 year old nephew daryl. i remember thinking daryl was super hot. he had a bmw and a range rove… Read more

Posted by cxdboi 19 days ago 2 2,161 82%

2 TV CD Sissy have wild time in gloryhole

Group SexInterracial SexShemales

A TRUE story I wrote a while back about a TGirl friend from the Dalles, Or. who would cum to PDX once in a while to dress and play. She always had a tight asspussy and she would easily cum when a cock was fucking her. So I would make her jack off while I was fucking her so I could feel those gripping convulsions her orgasm would give my cock. Makes me hard just remembering those orgasms. ~ "Oooh, Yeah, suck that cock you tranny bitches". The 6'2' black man growled as he closed his eyes in ecstasy. He was quite a specimen, skin almost coal black, shaved head, brutish face, heavil… Read more

Posted by CrimsonQueen17 19 days ago 2 1,370 100%