Shemales Porn Stories
Page 81

Delilah and the Deep Blue Sea. (part four)



The skipper of my boat was a man of few words it seemed for he maintained a taciturn silence as we sailed away from the island. I didn’t mind the lack of communication. I huddled miserably in the stern of the fishing boat, lost in my own thoughts and hardly in a mood to talk. My tear blurred eyes were fixed upon the dwindling view of the island as we left it far astern. Soon it was nothing but a pinprick on the horizon and shortly afterwards I lost it in the afternoon haze. It felt as if something had been torn from my soul.
I blinked away my tears and glanced ahead. A sliver of land had ... Continue»
Posted by Mikebasil 3 years ago  |  Categories: Shemales  |  
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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 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Moms teaches son to become a sissy sperma slut

I never knew my dad.

That's not an excuse for what I've become – and that's not to say I need an excuse – it's just a simple fact that some people find relevant when trying to examine what I've become.

Anyway, he was killed in a plane crash before I was born. Technically, he was killed in a plane crash while I was being born, but he died without knowing that. He'd been overseas at a business conference when my mom called to tell him she was going into labor, and had boarded the first plane he could back to North America. Ironically, it wasn't that long, turbulent, twenty hour flight that... Continue»
Posted by momandboys 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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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  |  
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The MILF next door [parte uno] (Karen)

This a story, fictional, nothing more!

I have lived in the the out skirts of this big city for quite some time now. I do have a great relationship with most of my neighbors and the community in general.

Across the street is the old grumpy George, he sits in his porch and drinks his coffee every morning looking at people gone by, always complaining about something. Next to him are the Rogers, nice f****y, and on the other side are the Smiths, and on my right side are the Ortegas, nice Mexican f****y, on to my left were the Chavez, now only one member of the f****y left in the house duri... Continue»
Posted by ilialenyc 1 month ago  |  Categories: First Time, Shemales, Voyeur  |  
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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 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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First time dressed in a club Pt # 1

I had been wanting to go out to a club dressed for sometime but was having a hard time deciding to do it, up to this point I had been only dressing in my apartment and for my friend Bill who live upstair from me mostly when he would come down and we would have sex together. I had told him several times of my need to do this and I asked him if he would go with me but it seemed he was into only seeing me dressed here and having sex with me.
I decided that I needed to do this for me just once to actually see if I could be around people dressed as a girl so one night I got a hotel room away fro... Continue»
Posted by MonicaBond 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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The story behind the small penis...

Some guys are not well endowed, or are, because of genetics. Not so with me. I have hypogonadism, basically my body doesn't produce testosterone in amounts higher than females (and yes, females have it too, just less). It results in a small penis, large breasts and receding testicles. Everything works just fine, but those are the physical effects of the condition in extremely abbreviated terms.

It does grow disproportionately large because of the relative smallness to begin with, but gets to be about 6 inches when erect (almost average, just a little on the short side for a male). I am real... Continue»
Posted by or1212 3 years ago  |  Categories: Shemales  |  
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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 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Sissy Emma is Turned Chapter 5

After that they let me go home.

Everything had been removed other than the cage which they said should remain on throughout the week to ensure my mind was attuned to being a sissy. Once home I showered myself completely and fell into a deep exhausted sl**p.

The following day I went to work and tried to act as normal as I could despite the fact that I was wearing stockings and panties underneath as instructed, not to mention having a butt plug stuffed up me and my 'sissy clitty' in a cage. All day the sensations reminded me they were there, the silkiness of the stockings against my hairle... Continue»
Posted by emmahighheels 3 years ago  |  Categories: Shemales  |  
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He shared me with his friends

I was in an adult book store in Bradenton Florida. I had my sissy cloths on under my male street cloths. Once I was in a private booth I took of my male cloths and was left in my bra, panties, and thigh high stockings. Some lipstick and I was on my knees at the glory hole waiting to suck some dick. The first one through the hole was nice. Clean. I suck him for a while when he bent down and asked to come into my booth. I said sure and he went around to the door and I let him in. I dropped to my knees again and took his dick out and took up where I left off. As I sucked him I played with the nex... Continue»
Posted by firstknightd 4 years ago  |  Categories: Shemales  |  
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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  |  
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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 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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sissy wants to be black man's slut

Hi Sweeties! Guess what? Well, adult arcade sissy, Miss Terilyn Bardot, got her ass whipped but good the other night. It happen at an adult video arcade in Providence, RI.

One of the reasons Terilyn likes going there is because they could care less what kind of sex goes on in those preview booths. in fact they installed larger booths that hold up to 6 occupants. A lot of the adult bookstores, mainly the ones in Massachusetts, have signs posted to the effect of no sexual behavior allowed, or, one person per booth - violaters will be ejected...legal prosecution, etc. So that's why Terilyn lik... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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 11 months ago  |  Categories: Group Sex, Sex Humor, Shemales  |  
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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 4 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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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 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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14 Days to Gay - a sissy Training Guide

i wrote this as a guide for sissies to finally shed the inhibitions and go gay - for real - like they know they should. Be a gay little sissy like you were meant to be.......

14 Days to Gay
1. Wear panties all day. Listen to Permanent Princess as you fall asl**p.

2. Wear a thong all day. Watch Bimbo Blessing before bed. Listen to Permanent Princess as you fall asl**p.

3. Wear a thong all day. Use lip gloss throughout the day. Buy a women’s magazine (like Cosmopolitan) from the local grocer. Watch Bimbo Blessing before bed. Listen to Permanent Princess as you fall asl**p.

4.... Continue»
Posted by jamie_anne 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
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