Shemales Porn Stories
Page 12

Chubby Fag & Army Bruh

Drill Wknd Nig 4 Chub Sissy

That’s what the ad title read. When Devyn clicked on it , he found that the poster of the ad was a six-foot-four-inch, two-hundred-forty-pound, Black Adonis with a nine inch dick. The man said he was married to a Black woman, but loved fucking big ass sissy bois.

Lonnie, being the fem sissy that he was, replied to the post. He included a few pics demonstrating his ample, wide ass and moobs. He hoped that this Black god would be cool with a white boi like him.

Moments later the man had answered back and invited Lonnie over because he admired the big wide ass... Continue»
Posted by faggyboi 4 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Big Titty Young Boi Gets Owned

Baby Joe had always known since was in the seventh-grade and his gynecomastia, which is the condition that cause female looking breasts in males, never went away at the age most boys were already starting to see the androgen clock in to make them look like men. At the same, Baby Joe’s ass had begun to plump up and his hips started spreading wider. He had been effeminate since before he could remember and now he was developing a body to match.

At that tender age, the k** raised by a single mother in the small town, was taken under the mentorship of his older second cousin. Lawrence was 28 y... Continue»
Posted by faggyboi 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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My First Time

many of you have asked me about my first time. I had posted a story about it but it is gone so here is a re-post. Let me know what you think.

My 6th grade teacher was my first when i was 12. Being transgender and more girl then boy I would wear stockings, panties sometimes garter-betls under my boy things (UGH) when going to school. One day as I sat at my desk with my feet on he wrung of the chair my tight pants got even tighter. The clasp of my garter-belt I was wearing were clearly showing. I did not realize the were we were taking a test. The teacher walked down the isle and stopped... Continue»
Posted by MichelleSissy14 4 months ago  |  Categories: Anal, First Time, Shemales  |  
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Wank buddy 2

This is the follow on from my first story of the same title and the 2nd (and last) time I met with my wank buddy, Nick.

Quite a few months passed since our first meeting, we kept in touch on ‘Dick.net’ but our respective jobs prevented us from meeting up again. Eventually after much communication we managed to agree a date. Again it was a Wednesday but this time in the afternoon, around 14:00. Again we met at the same gay cruising spot and leading up to this meeting, Nick constantly talked about taking my cock in his mouth again and tasting my pre-cum. I, in turn, talked about taking his w... Continue»
Posted by LeedsXdresser 4 months ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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Wank Buddy part 1


The following story is true, sadly I only met my ‘wank buddy’ twice but the following is what happened:

I met Nick through a website called ‘Dick.net’, we had chatted and shared pictures for a few weeks and we then arranged to meet. Unlike me, Nick had never done anything with a guy, he only wanted to meet for mutual masturbation and may be oral but he refused anal completely, saying it wasn’t his thing as he wasn’t bi or gay. I found this funny as he kept referring to me as gay because of my previous experiences with guys (Including anal) and was surprised I was still married – Like I ... Continue»
Posted by LeedsXdresser 4 months ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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Crossdresser teacher violates 18yo sissy schoolgir

I am a home schooling teacher, short skirt with side splits tight but stretchy over my right bum, black stockings and black lacy see thru panties wig, white sparkly heeled sandals and Lacey see through top sat opposite you on the couch. You are wearing a shirt and tight school skirt, white see thru Lacey panties and nude colour tights and black boots, tight school shirt white bra and pigtail wig.
I sit opposite you on the couch occasionally opening my legs slightly giving you a glimpse of my bulge. You see I'm a sissy too and get upset, I come over to comfort you, stroking the inside of you... Continue»
Posted by shysissyfitbum 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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My first time part 2

Its been a while since my last story so I thought it was time for an update. My transition is almost complete, my breasts are round and firm and my body is taking on a more female shape. I was at the shops the other day and was chatted up by a good looking guy, so must be doing something right lol. I have sorted my business to having a few well paying clients, so I have a bit of me time.
I was out with a friend having drinks the other day, of course this involves shopping for new clothes and heels, when she happened to mention that she had been to a sauna. I asked her what happened there and... Continue»
Posted by ambu99977 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Motel Blackout

I always enjoy my sales trips. The trips fit into my crossdressing lifestyle and the thrill of being in a different town and different people.
After a long day on the road, I had just checked into a motel just about 30-miles outside of Nashville, TN. For my overnight trips, I always bring my special suitcase that has my “girly stuff” (panties, dresses, makeup, lingerie, etc.). Sometimes I would just dress up pretty and cam or play with myself. On a very few occasions I would run into a very horny stranger, tease him, but not put out and be satisfied knowing that poor guy was back in is room ... Continue»
Posted by MatureBrownMan 4 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Motel Blackout

I always enjoy my sales trips. The trips fit into my crossdressing lifestyle and the thrill of being in a different town and different people.
After a long day on the road, I had just checked into a motel just about 30-miles outside of Nashville, TN. For my overnight trips, I always bring my special suitcase that has my “girly stuff” (panties, dresses, makeup, lingerie, etc.). Sometimes I would just dress up pretty and cam or play with myself. On a very few occasions I would run into a very horny stranger, tease him, but not put out and be satisfied knowing that poor guy was back in is room ... Continue»
Posted by MatureBrownMan 4 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Picking up mom was early had some time

Well, just a recap if you do not know anything about me. Grew up and raised as a girl, just mom and I, She works at a dinner and spends Thursday nights at my house (you can catch up if you read some of my post)
Anyway, Last night I went to pick mom up from work I was early and pulled behind the dinner. Was such a hot night I had the tops down on the 65 t'bird was wearing a short wrap-around flowered pattern skirt, a black danskin leotard, white flats, black wig in a BOB style, full makeup.
Anyway, I parked in the alley and got out leaning on the car having a smoke (yea I smoke but do not dr... Continue»
Posted by MichelleSissy14 4 months ago  |  Categories: Anal, Shemales, Taboo  |  
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My first driving lesson! - A sissy’s path to freed

My first driving lesson!

A sissy’s path to freedom.

One late winter evening after my last day of secondary school I went around my neighbour’s house, as he said if I’d do a good job of cleaning his house he would give me some driving lessons for free as this was his job. He was expecting me to clean his house this evening and he opened the door to me as I knocked. “erm hi Vince , it’s still ok to clean up and go for a drive later?” I ask holding a pink feather duster, unfortunately the only one that was in my house. “yes girl come on in and get started.. arh sorry I mean boy” Vince repli... Continue»
Posted by dirtyjenna 4 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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YOU MUST SUBMIT!

If you take on the role of Sissy Slut Cock Bitch then you must be that bitch for everyone! No cock presented to you can be refused you must be like a slutty dirty girl in high school just looking for boys to suck and fuck she can enter a room and know who has the biggest cock she can spot him from a distance...Never go after the macho guys they think they are too good for you go for the kind of girly guys who look sweet unless the macho guy comes on to you and knows what you are then it is okay you may fuck him to your hearts content and he will satisfy you but you must do whatever he wants no... Continue»
Posted by laceysgirl 4 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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Sissy Ex-change student in Asia

Sissy Ex-change student in Asia

The warm night air was drifting in through the open window along with the scent of the nightly food stalls being ferried around the oriental streets. Hustle and bustle carried on here regardless of the night’s plans for us all to come to rest. Yet the a****l in us likes to play at night especially at night and especially for an in-experienced sissy exchange student like me wondering what these Asian’s have to offer on the sex scene.

Already in my prime sissy condition due to my inner slut getting horny and needy of expressing my kinky sexuality, I’d shaved... Continue»
Posted by dirtyjenna 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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my 2017 Dr's appointment


My Dr visit 2017


Like the previous years I had my annual Dr. appointment and since now both the nurse and the Dr. know I'm a feminine male (the male term I use very loosely:) I really don't have to hide the fact and as before my recent visit certainly validates that. I showed up wearing cute white shorts with a very pretty lacy bra and cute panties underneath, topped off with a somewhat feminine blouse that did not really conceal my bra if you looked. After checking in with the receptionist I took a seat and waited to be called back to the Dr. My hair is only down to my shoulders an... Continue»
Posted by sissygirl 4 months ago  |  Categories: Gay Male, Shemales  |  
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My Dark, Sadistic Side.

Finally after 10 months of chatting exchanging photos and even Skyp'ing twice, by a miracle of fate, I was going to actually be with Kim. Kim is my FANTASSY, ON-LINE TRANSEXUAL LOVER. Kim lives in the UK so it always was just a mutual fantasy that we would ever meet. Then fate smiled on both of us, Kim is earning her PhD and has taken a sabbatical. She is coming to the states to attend a world class mathematical seminar at the Courant Institute in NY City. She will be here for two whole weeks!! NYC is only a 3 hour drive from where I live , so of course I was honored and overjoyed when Kim tol... Continue»
Posted by Lossst 4 months ago  |  Categories: Anal, BDSM, Shemales  |  
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You're My Bitch Now Part 10

Part 10

Rick scurried into work, determined to stay away from Rhona as much as possible. It was as busy day and he had to go sort out the Marketing Director’s laptop, which she had screwed up somehow. Rick spent an hour trying to fix it remotely, but in the end had to her office to pick it up and take it back to the office. Rhona, of course, was there and wanted to know what he was doing. ‘She's important, Rick, don't screw it up. Don’t make me mad with you.’

Rhona’s mood became worse and worse during the day and she gave everyone in the team a hard time. Rick began to worry about the n... Continue»
Posted by nikkiesilk 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Sissy's Play Date with a Real Girl

Some days had passed since my last adventures in the woods where David had me all dressed up to be a fuck doll for whomever was fortunate enough to pass through that patch of land. Nothing out of the ordinary there, the surprise was he had a new girl there to join in the action. Though hurt at first I found I was kindered spirits with her and we took our mutual love of cock and formed a friendship. We made plans to hang out at my house, which pleased my father no end to finally hear I was with a girl. Little did he knowwhat we were to get up to.

Amy called round at four, she had her long b... Continue»
Posted by emmadeevine 4 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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How I Started

Hey- This is a personal story. Let me know what you think. Mostly true...'cept names and a few other things...enjoy!!!!!!!!

How Rebeca Started

Then, out of the blue, I received a friend request on F-book from the man who started me out. At 43, he was 31 years older than me when he and I played.
I was on summer vacation and discovered masturbation in an unlikely way. Mom and dad had split up, so mom was at work during the week.
I’d watched a series of movies that involved prostitutes that looked really hot and easily captured my imagination.
I had been touching myself, but no... Continue»
Posted by 6988slutty_rbckyy 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Bianca Behind Bars (Part 1)

After a night of d***ken debauchery, the futa goddess Bianca found herself locked away in a cell in the local county jail. She was being charged with disorderly conduct and indecent exposure, and was e****ted out of a dive bar called the Hot and Heavy Lady last night. Now, the morning after, Bianca woke up in a cell by herself, confused and incredibly hungover. This was the first time she ever got arrested, much less found herself behind bars, and the entire situation seemed so surreal.

"I see you're finally awake, Miss Thickrod. I'm Officer Goldsnatch and you're in the Cuntsville County J... Continue»
Posted by BiancaBigTits 4 months ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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Mark, MJ and me II

{Some of my stories are factual butt much is poetic license}


We smoked the MJ. Then we lay together and took a nap on his s****rs bed in her BedRoom {BR}. I woke up still in my girly lingerie. M. was totally naked. I looked , rather stared at his soft pinkish cock. I now knew my summer plans were to get his cock in me and be his part time {prefer full time} GF. He stirred. I reached over and played with his cock. It hardened in my tiny hand.
Slam we hear a car door. ”It’s my mom home from work early. Quick get dressed.” He quickly began t... Continue»
Posted by robin48 4 months ago  |  Categories: Gay Male, Shemales  |  
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