Shemales Porn Stories
Page 56

The continued adventures of Allison the cumsissy

The Continued adventures of Allison the cumsissy
This is a continuation of the same sissy slut’s story from my two previous works about Allison the sissy schoolgirl and her black daddy.

After the week long fuckfest, Allison the sixteen year old sissy schoolgirl boybitch had with her black daddy neighbor, she realized she was meant to a be a sissy cumwhore and decided to shop for as many sissy items as she could afford as soon as she could discreetly do so. As luck would have it, the following weekend her parents informed her that they would be going out of town yet again to visit his mothe... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1901  |  
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My first time as trany


Many times in my puberty secretly wearing panties of my mother or my s****r, and I looked in the mirror and I exitaba much finished masturbating several times.

One afternoon when he was almost 20, my aunt asked me to help you move from flat boat that calls me a bag of old clothes which I call my curiosity and take her home; Upon arriving home I looked it had in the bag and found three pairs of socks one corsel league, thong panties and some several gowns. Which used at night and in secret of all.

For hallowing night we had a costume party at the home of my best friend Manuel "Manuel wa... Continue»
Posted by elsuper-raton 1 year ago  |  Categories: Shemales  |  Views: 509  |  
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My first time as trany


Many times in my puberty secretly wearing panties of my mother or my s****r, and I looked in the mirror and I exitaba much finished masturbating several times.

One afternoon when he was almost 20, my aunt asked me to help you move from flat boat that calls me a bag of old clothes which I call my curiosity and take her home; Upon arriving home I looked it had in the bag and found three pairs of socks one corsel league, thong panties and some several gowns. Which used at night and in secret of all.

For hallowing night we had a costume party at the home of my best friend Manuel "Manuel wa... Continue»
Posted by elsuper-raton 1 year ago  |  Categories: Shemales  |  Views: 349  |  
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She tricked me & am I glad

My most frequent fantasy is to be dressed like a slut for black men. I think about it at least 3 times a day. The most recurring fantasy is when I meet this black woman that turns me on. We talk for awhile and it seems like we are hitting it off pretty good. Then out of the blue she asks me if I want to continue this conversation at her place. Could I be this lucky? This fine black woman was inviting me to her house? Yes I told her smiling from ear to ear. She smiled back and told me to follow her. We get to her house and she tells me to have a seat while she gets more comfortable. I am sittin... Continue»
Posted by iwannabeacumslut 1 year ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1587  |  
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A Slut is Born

A Slut is Born
I am a bottom for sure. It has been a long time, 20 plus years, but do miss it alot. Back then, I was in my 30's and this guy I met while I was tending bar talked me into coming to his camp for some fishing. Needless to say I was the fish and did not know it. He picked me up and we went to his camp which was 1 big room with a kitchenette and a big bed, sofa and a TV. The bathroom was small with a shower only. I noticed right away he had a wall filled with VCR tapes and I am a movie buff so went over and started checking them out. HMmm, I did not recognize the titles but felt t... Continue»
Posted by iwannabeacumslut 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2098  |  
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A Very Good Night

I sat on the edge of the bed waiting for his text. He told me he would let me know when he pulled into the parking lot so I could be ready. He wanted it to be completely anonymous. The room was mostly dark and I was to be blindfolded and on all fours, ass up and at the edge of the bed ready to be fucked. I LOVE anonymous sex. Sex clubs, video stores, cruising spots. The act of taking an unknown cock in my hungry cunt had my heart racing. I had no idea how old he is, age, or his race. All I knew about him as that he loved to fuck tranny pussy and fill it with cum.

My phone went off and I ope... Continue»
Posted by kbking70 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1791  |  
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My new ladyboy- LittleLi - Part 1

It was nice to meet my new freind littleLi. I met her at the library at college one day and was immedietly attracted to her. Her long dark hair and big brown eyes, with a lovely sweet smile. She was wairing a little cropped T shirt with a hello kitty picture on it, showing off her smooth honey coloured tummy, cut off denim shorts, white frilly ankle socks and black patent pumps. I thought to myself, only an asian girl could wair little frilly laced ankle socks and mary janes and get away with it! I had known for ages i was bi, so i was not suprised that this fanatastic girl standing in fron of... Continue»
Posted by igglepiggle 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1885  |  
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My Ladyboy- LittleLi- Part 2

After LittleLi had finished swallowing my cum, she fell back and i noticed she still had on her frilly ankle socks and MJ,s. Now that I knew LittleLi was a ladyboy i could tell her about my collection of stockings, panties, shoes and dresses that i liked to get dresssed in. LittleLi loved the the fact and took off the rest of my man clothes. I got up off the bed in front of her naked and went to my cabinet with all my fave clothes in it. I lay out satin frilly panties, stockings of all different colours and school uniforms with knee socks from Japan to England. LittleLi immediately ordered me ... Continue»
Posted by igglepiggle 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 1274  |  
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my first gay experience

it was the christmas party and last orders were finished, so i was making my way out when debbie and jenny two lesbians who i work with asked me if i fancied another drink. yes i replied where are you going? we are going to the gay bar wanna come? after a brief pause i said yes but only because i want another beer. we entered the club and i bought the girls a drink, after about five minutes this stunning brunette came over and started hugging the girls, then they introduced me, paul amanda amanda this is paul. i just stuttered as i shook her hand she was amazing a tight fitting little black mi... Continue»
Posted by pabs42 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 2940  |  
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Sissy crossdresser and her Black Daddy Part 2

After nearly a week of almost nonstop creampies, facials,deepthroating blowjobs and bareback anal fuckings, my black daddy and I were sad to know we had one more night in which to have our nasty, kinky fun before our respective f****y remembers return. I had dressed in all manner of nasty lingerie and costumes for his black cock to use and I loved every second in which he entered my holes. This being our last night together my daddy told me to "take a shower white slut, and make yoself pretty. I got a surprise for dat ass babygirl". My cock could hardly get any harder I was so excited. I enter... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3062  |  
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First time giving a blow job.

I was a bit younger than I am now when I met a boy a bit older than I was who just caught my attention. He was a closet gay, I was bi-curious. He was so attractive. 6'1", 80kg, tan, short hair, brown eyes with a great fashion sense. For now, we can call him, Joey.

My friends and I were out clubbing one night when we stumbled upon Joey on his own at the bar. My friends were more interested in dancing, but I wanted to sit with him and see what was up.
We chatted about minor things like school, parents and our sexuality. He was the first person I told that I was curious and I was the first to... Continue»
Posted by ShulaV 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3947  |  
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Cruising and Swinging 3

Blackmailed
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»
Posted by lankybacon 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2569  |  
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Schoolgirl Sissy Crossdresser and Her Black Daddy

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»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3204  |  
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THE Sissy a*****ion

You are walking along, you feel a presence, a person quickly comes up behind you and chlorophyll you. You pass out but you catch a glimpse of his green army officer hat.


You wake up several hours later chained to a rack naked. Two identical women come out with a cart filled with cosmetics. First they take this special soap that when it touches your skin it makes your skin very sensitive and a sensation of pleasure takes over at the slightest touch, then the two women grab nail polish and paint your toes and the your fingers. Then, they grab a special foundation that they apply to your wh... Continue»
Posted by thegoods699 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1708  |  
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Ice Cream Sex

Amongst the contemptuous gender variant community in Springdale, Fernander Kago had earned the reputation of a pussy maker. The thirty-one year old immigrant from the Central African Republic was addicted to fucking boipussy. It was impossible for him to be faithful for two reasons. Firstly, because he was always horny. And secondly, because the first tranny in fucked in town told her friends how big his dick was. Now any half-way effeminate being with a penis was after him.

Tonight the dark-skinned five-foot-ten-inch, one-hundred-eighty-five-pound man was headed to the Roadside Motel to sp... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1277  |  
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A Fantasy

For leannaxtsx

During the flight he had a hard time falling asl**p. He kept all her posted pics in his phone and went a few times to jerk off in the bathroom while looking at her body. When he found out he was about to go to a convention for 3 days and as it happens to be the convention was at New Orleans he arranged to stay for a few more days "to see the sites". Now he was on his way and he knew he had to wait for 3 days until he could meet her. He contacted her a week before, at first she wasn't very cooperative but he managed to convince her they should meet. He promised to... Continue»
Posted by mobi_dick 1 year ago  |  Categories: First Time, Shemales  |  Views: 1065  |  
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Their First Adult Book Store. Part 3

Gary loved seeing Albert's big cock, jacking off, on the other side of the glory hole. He guessed that Albert was sporting at least seven inches. Maybe eight. Gary wanted that cock. He put his fingers through the glory hole, beckoning. "Albert, gimme your dick."
Albert couldn't believe what was happening. He was so excited that his mouth had the taste of extreme forbidden horniness. Albert stopped jacking and put his dick through the glory hole.
Gary was in heaven. When he first saw the two twinks, it was pure fantasy that anything would happen with either of them. Now he was about to wrap h... Continue»
Posted by Michelle_Satin 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1308  |  
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He has made me the town slut

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»
Posted by firstknightd 1 year ago  |  Categories: Group Sex, Shemales  |  Views: 3120  |  
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Online Hookup

Jamie Harris typed in the user name and password of his account with his favorite online amateur porn hosting site. He was alerted to a new message. He clicked the envelope icon and viewed the correspondence from screen name ‘DLdriller’.

Damn fembunnybttm!!! I wanna get in that ass. Where are you located? I think we stay close.

Jamie fired off a reply with his location along with his email address and the number to his spare prepaid phone. He logged off the computer and hopped in the shower before heading to work at the clinic where he was the administrator. Later that day, Jamie retu... Continue»
Posted by faggyboi 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1791  |  
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Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossd... Continue»
Posted by gypsy61 1 year ago  |  Categories: Mature, Shemales  |  Views: 1333  |  
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