Shemales Porn Stories
Page 68

You've Got Shemale.

This is my first story of this type, so please, be gentle ;) It's a semi-true story, but definitely more fiction than fact, and it will be at least two parts.



I moved to a smaller town when I was in college and found that I didn't fit in at all. I actually got so lonely that I took up a friends advice and joined a dating site.

I had gone through a large number of messaging women on that site to find most remotely near me wanted nothing to do with me. My age range of early twenties had little selection and those that were in that range were surprisingly stuc... Continue»
Posted by MysticDude 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1437  |  
95%
  |  5

She became He

The day started as normal, wake up get dressed, have breakfast,but today was going to be anything but any normal day.

I decided that i would take the day off work and visit a local sex cinema,i had never been to one before and was a bit aprehensive but i thought sod it let's just do it.

Upon reaching the cinema i stopped as my heart started to race,after a minute or so i carried on in and paid my money and went inside.

I took my seat about 3 rows from the back there were a few people inside but not too busy,anyway after about 15 minutes of the film and with my cock starting to throb i... Continue»
Posted by carlosos 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1436  |  
98%
  |  6

My Shemale Girlfriend 8: My Mistresses

Sorry i haven't been writing stories, I've been a full time slave of multiple mistresses the past year. if you read any of my other stories, you'd know my beautiful girlfriend/mistress Christy, who is my main mistress, Brittany, her friend from Denmark, is my secondary mistress and has moved in with us. My third mistress is Jennifer. Jennifer is usually only my mistress when one them are gone, but still often there. Often, all three of my mistresses are present to use me as they please. They own me, i am nothing but a toy used for their pleasure and entertainment. They dress me up in whatever ... Continue»
Posted by germanface 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1435  |  
100%
  |  1

The best s****r ever part 6

Yes this is all true and please start reading from the first story please.

The next morning again me and my s****r were the early rises and had a fun idea for revealing the f****y secret to my girlfriend. First we went to our parents room to tell them that we were about to tell her this morning everything so we went downstairs to the kitchen and started to cook some toast.

Just before all the toast had been made, my girlfriend came down and walked over to us. She came over to me and when she went aroud the counter she saw all of us had no bottom cloths on and all had hard cocks and she j... Continue»
Posted by horndogs 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 1431  |  
94%
  |  4

Girlfriend's Hairdresser

“Look, honey,” proclaimed Kamron as he held a mirror in front of his client.
“I like it,” she declared with a smile. “How much,” she asked.
“Fifty-five,” the five-foot-nine-inch big booty effeminate hairdresser replied.
“Alright,” she said digging through her purse. “Oh damn. I left my billfold in my other purse. Do you mind if I get Tavares to drop it off when he gets off work,” she inquired referring to her live-in boyfriend that worked at the auto parts factory in town.
“Yeah, chile. That’s fine. What time does he get off?”
“Seven.”

“That oughta be fine. Just text me when he’s on th... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1430  |  
82%
  |  5

He Got Used and Didn't Mind (Part Three)

Great responces so once again 10 comments or 1,000 views gets part 4. I hope the categories are listed correct this time. Part 4 may be the last to this series unless I get fed some ideas after it. If you like the series please comment.

The next morning Dave woke up at Lucy and Carla's feet at the foot of the bed. He went to wake them and they each smacked an ass cheek. "Dave come take a shower with me." Carla beckoned as she nibbled his ear. Lucy nodded in approval and off they went. Once in the shower, Dave started to wash Carla's soft, chocolate body from head to toe with a gentle massag... Continue»
Posted by mrman1982 1 year ago  |  Categories: Voyeur, Shemales  |  Views: 1430  |  
100%
  |  2

Halloween Disguise: pre-story by DanaWu

an original story by me. its not true more of a fantasy...

this story starts october 14th. first of all i am a 23 year old boy, i just moved to a different state to go to college, i dont have many friends and have only been her a couple of months.

today was like any other day, had to wake up early and go to work for a couple hours before school. julia, one of the first people i met here, approached me today and told me about an "awesome" party tons of the students have every halloween. she tells me about the last years party and some of the crazy things people dressed up as. she mentions... Continue»
Posted by DanaWu 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1430  |  
84%
  |  6

my first tranny pt. 2

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»
Posted by radec_24 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1427  |  
96%
  |  3

Gift of a blowjob

Some years back when I was younger and occasionally crossdressed, I was staying in a motel out of state. My room was on the second floor and had a full floor to ceiling window overlooking the parking lot. I was dolled up very sexy, and drinking wine. It was early evening but already dark. I noticed a man walking around the next building several times, and as he'd come around his walk placed him walking straight towards me. I think he was just walking for exercise. I thought he might be a good candidate for me to tease a bit, so I watched until he came around again and stood in the window with... Continue»
Posted by dana213 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1426  |  
91%
  |  10

transvestite in trouble

i pulled up on the pub's carpark. I was nervous, i'd been speaking with Andrew for about 2 months online and for 2 weeks on the phone, we'd always end up jerking off when we spoke. it was during these chats that i'd told him of my fantasy. The one where i'm overpowered and f***ed.

I was dressed as instructed, black lingerie, suspenders and black stockings, tight high wasted skirt, just above the knee, white blouse and black jacket, i had on 4" heels, Andrew liked the secretary look. there were only 3 cars on the carpark, Andrew had said this pub would be quiet at this time on a Thursday, it... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1423  |  
83%
  |  10

Bad Habits CD Fantasy

Why did I keep making bets like that, was the only thing I could think of while in line. Why did I keep making bets I was destined to loose, and then have outcomes like...well, this. I was standing in line to go to a cosplay convention, and was in full costume, but of the wrong gender. I was dressed up as one of those Vocaloids, with knee length blue pigtails, A black skirt that was barely at my knees, a set of black and blue boots that went up to my thighs, a sleeveless vest like shirt, a weird belt thing, weird glove-like sleeves (that left my armpits and upper arms open for the whole world ... Continue»
Posted by RosalynLee3 9 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1423  |  
100%

Swimsuit summer 2010

This really happened and even now I got both excited and scared thinkig about it.
Near me there is a bay that's very quiet, even in the height of summer its rarely visited, and I took to driving there in my car and sunabathing in just my swimsuit and hairpiece...seeing as many females of my age ar'nt stunning beauties and rarely wear make up whilst sunbathing I knew I'd pass at a distance .
On the first occasion, a man came quite close and said 'hi' as he passed and I just raised my head and nodded as I lay on my tummy. A couple passing by also gave me a wave and I waved back , apart from th... Continue»
Posted by holaryhilary 3 years ago  |  Categories: Shemales  |  Views: 1421  |  
71%
  |  2

The best s****r ever part 4

Yes these stories are true and please start from the beginning. So far me and my s****r have been fucking for about 4 or 5 years and our dad has recently caught us and joined in.

Out of our parents our mom spends the most time at work so we always found it easier to have sex now that our dad knows whats going on. Over time he let us fuck him anal and he enjoyed it as much as I did and we started to do something called "naked hour" which happened every friday evening, where our mom works until 11pm if she comes home early.

After several months of doing this naked hour sessions and we coul... Continue»
Posted by horndogs 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 1420  |  
95%
  |  3

Drama queen part three

Drama queen part 3

The next day (Friday) I got up and dressed in clean lingerie and a mini skirt with top, I did my make up, I was getting better; especially after the tips Alice had given me. I took my dirty lingerie and loaded it into my washing machine. I did notice there were no male underwear, and did a smile to myself. I checked the skirts, top and dress I had worn and decided that they needed a wash too so they were set aside for the next load. I remembered I had some essays from Drama school to mark. The rest of my day was spent reading and marking with the occasional break for natu... Continue»
Posted by hottvcarole 1 month ago  |  Categories: Group Sex, Sex Humor, Shemales  |  Views: 1421  |  
100%
  |  3

Superbowl Party

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»
Posted by pandys 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 1419  |  
100%
  |  7

my first cross dressing play time

i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and would like to find somebody to dress up with and take turns being sluts to each other and then i posted a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks but i finaly found somebody that like to dress up and he came over during the day and we started watching porn and i pulled out all my slut clothes and we picked out things that we wanted the other person to wear. he wanted me to dress up just like the pics i sent him so i did, after we got dressed up we... Continue»
Posted by floyd1985 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1417  |  
75%
  |  5

Allison the pool slut part 2

After using and abusing Allison’s white asspussy, and giving her a refreshing and kinky golden shower, Jay informed her that they weren’t done being kinky yet. He was not lying…

Jay’s hand gently grabbed Allison’s and pulled her to the house. Their intense poolside fucking had left Allison’s teen butthole full of warm seed and as she followed him inside it began to run down her thighs and her strappy stripper heels. “Go on up to my b*****r’s room and put on some of yo sissy stockings babygirl.” Jay commanded. Like a good white whore, Allison’s heels clacked on the hardwood floors as she did... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1419  |  
100%
  |  1

horny

It was a Friday night and my boyfriend Conrad and I were at a sports bar getting wasted and watching games. Conrad loves watching me flirt and this night was no different and there were lots of men to flirt with. We were playing darts when we were challenged to a game by these two black guys. They introduced themselves as Travis and Kevin and in no time, we were having fun playing and drinking. Kevin was the larger of the two at about 6’2”, 250 lbs. He was really dark and the quiet type. Barely spoke, just smiled. Travis was light skinned and tall and thin, the outgoing/player type and instant... Continue»
Posted by conradherts1 1 year ago  |  Categories: Shemales  |  Views: 1417  |  
100%
  |  1

A true story: me and a transvestite man - part 2

OK this is the second part of my true story. I was going to leave it at two parts, but I think there's enough to make it three parts, now!

I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd not had any experience of men. You won't, of course, get many straight men who admit to this. But I'm not like most men.

However, this early experience was enough to leave me curious as to what it would be like to have fun with a cock. As you may have read in part one of this story, I was rapi... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1416  |  
96%
  |  3

Confessions of a She-male Toilet slave.

CONFESSIONS OF A SHE-MALE TOILET SLAVE
CHAPTER 8 - TESTED AND FOUND WANTIN'...

This is a short story about my first wife, about the day the World changed for me. When we married she was bi and a swinger, an older woman (40), and lot's of fun, I was young, barely 18, we swung all around town, her and her pretty boy. As soon as she got into my ass it was her friends using me, not her sharing her 'toys' with me... By the time we split up she was living as a hardcore biker dyke, and I was chained in a k**die pool in the basement serving as a human toilet, urinal, cum dump, and fist hole for w... Continue»
Posted by bucketkunt 11 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1419  |  
100%
  |  3