Shemales Porn Stories
Page 69

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: 1427  |  
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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 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1426  |  
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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  |  Views: 1426  |  
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The Long Road To First BBC part two

What's wrong with me? I love pussy. I love women. I was so paranoid, I just knew everyone was looking at me by the time I got back to the motel. I was certain that everyone I saw could tell that I had just sucked a cock. The desk clerk asked if I had a "Good" time while I was out. How did he know? Do I still have some cum on my face? I could still smell and taste the cock that I had just let explode in my mouth mere moments ago. I just needed to get to my room. No one could bother me there. Finally I arrived at my room.
As I stated earlier, I have an average size dick 6" no more or no less.... Continue»
Posted by proudman2 17 days ago  |  Categories: Interracial Sex, Shemales  |  Views: 1430  |  
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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 10 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1423  |  
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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  |  
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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  |  
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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 2 months ago  |  Categories: Group Sex, Sex Humor, Shemales  |  Views: 1420  |  
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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  |  Views: 1418  |  
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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  |  
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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 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1418  |  
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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  |  
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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 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1416  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 1416  |  
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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 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 1415  |  
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My very first experience with my classmate (episod

He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i felt the tears running down my cheeks as a result of this emotional discharge and hugged him,saying ''I was scared to death..of losing you...I thought you would never talk to me again''...Maybe i was being hysterical but i really wasn't thinking healthy at that moment..a typical girl:) I started to ... Continue»
Posted by Slave4str8twinks 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1413  |  
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Summer Fun

*Crossdress Story*


Living with your parents is exceptionally annoying, especially when you're 26 and have a fetish for crossdressing. It kind of hampers your "need" for putting on slutty outfits and parade yourself in front of a webcam with a pink-glass buttplug up your ass and a giant rubber cock vibrating away as it burns down your last pair of batteries.
But alas, it's the position i'm in and somehow i've made it this far without too many suspicions.
There was the incident a few months back when my mum and dad were at work and I took the opportunity to clean all my sex toys; taking t... Continue»
Posted by KitsuneTV 3 years ago  |  Categories: Shemales  |  Views: 1412  |  
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Amy The Tranny Chapter 1

I met Amy at an adult theatre in town.
She was dressed to nines in a mini skirt, tight
halter top, and pumps leading up a pair of fishnet
clad legs. I invited her into a private booth
and once inside, went over her price for some
adult fun. She told me I couldn't fuck her as she
was on her period but I knew something was up and asked
her flat out if she was a tranny. She looked at me wearily and slowly nodded her head. I assured her I was into tranny sex and she relaxed and asked if I was into just a quicky or a longer more relaxing session back at her place. Of course I opted for th... Continue»
Posted by panteeluvr 3 years ago  |  Categories: Hardcore, Shemales  |  Views: 1411  |  
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Found my Way

New Years eve I met some guys at a bar that invited me to a party. There were about five couples and they were leaving and going to a house a few miles away. Follow us and don't drive d***k they told me.
Another two rounds of shooters and we left.
Fifteen minutes later I followed the group into a big house in Buckhead.
Ten minutes later I was sitting back on a couch smoking a joint sipping on a mixed drink.
I was so high my vision was blurred and I dropped my drink. I was about to pass out. Billy was one of the guys that invited me to the party came to me and helped me get up and he moved... Continue»
Posted by CrossdresserAtlanta 4 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1411  |  
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Hedonistic Crossdressing, Part 3

The best way to describe Vince, probaly is that he was a socially functioning pervert. I had no idea just how varied, and intense, his sense of erotica was, but I was going to find out as time went on. Perhaps the worst thing is (or best perhaps, depending on your point of view), is that I became quite the little "apprentice", you might say.

I'd been his "guest" for only a few hours, and I'd experienced more than I'd ever dreamed. I've dressed, I've sucked my first ever cock, been fucked hard up the ass, taken cum, been made to cum like a girl, been made to take ass to mouth, w... Continue»
Posted by elainetgrl 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1410  |  
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