Shemales Porn Stories
Page 74

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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becoming Rachel 2 - A night out at a fetish party

So I had been Rogers trans-mistress for about 2 years. as he was also a p/t Tranny he had taken me on as his little teen (19 year old) apprentice tranny.

he was in his mid-40's, he taught me how to walk, how to sit, how to talk, how to suck cock and deepthroat, how to fuck. lately he had me taking some estrogen tablets which had made my skin softer, changed my voice and given me little cheery nipples. I liked all these changes and Roger told me that we would eb going to a 'party' i was very excited by this, as I hadnt been out dressed much and really liked it when I did. Roger bought me a h... Continue»
Posted by rachel_cd 1 year ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 1064  |  
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THE RECREATION OF BILLY ZERO

Life was okay before I lost my Mom I was a teenager and in my final year of high school I liked to play soccer and was on the team and it was when Mom was coming to pick me up from practice that it happened a d***k driver ran a stop sign and smashed into the drivers side of her car she was killed instantly I found out all this later when after a long time Jerry who was Mom's second husband showed up he looked bad and had been crying I could tell he said something bad happened to your Mom she was killed on her way to pick you up a d***k driver ran a stop sign and now shes gone! I was in shoc... Continue»
Posted by laceysgirl 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 1064  |  
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first time meeting with another CD

I was online and a message popped up from another Cd who lived local. He was married just like me and loved dressing up. We chatted for a few days and then he asked me over to his place as his wife was working. I had a few hours spare so i packed a few things and went over to see him.
when i turned up he was ready dressed and waiting, So as soon as i was in there i stripped and dressed up and aplied my make up. We admired each other for a while and donme all his house work between us.
We got close and looked into each others eys and then we just kissed. It was wierd at first but so nice.We ... Continue»
Posted by xdrespauline 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1064  |  
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My meeting with tranny milf Sandy 54 part 1

Wanna tell you about my meeting with Trannymilf Sandy 54!

I met Sandy through an add in a pornographic magazine I was 23 then so she was 31 years older than me. Wanting for long to meet a much older tranny beauty I got really excited when she agreed to meet me. We met in her apartment after I rang the doorbell a beautiful woman in her midfifties with a white dress long blond hair,white nylonstockings and white high heels opened the door. Her face had a heavy-makeup I was stunned by her looks. Welcome Nellie she said I guess you would like to change? Yes I said with a trembling voice and she... Continue»
Posted by NellieTranny 2 years ago  |  Categories: Shemales  |  Views: 1062  |  
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Stephon fucks Sora and her sexy ass tranny ass

Ya know what fuck it since my last story wasn't good apparently imma just cut the bull and tell the whole story now shit.

So my dick is in her ass and im in heaven, like on some cloud nine shit.the head board is knocking she screamming, im not sure how loud though cause im pretty focused.And like i said before she released the dragon or sme shit like that i mean, what she did quite literally was with me inside her flip her whole body so she is now all fours and im like... the fuck did i get myself into. but still i don't punk out. the she told me to go deeper. Alright how hard can that be. ... Continue»
Posted by cooler34 2 years ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1061  |  
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A Cross-Dresser's tale

You may think of me as Fiona, and I am a cross-dresser.
A story by Erica inspired me to pen my saga of cross-dressing.

I am also a recovering alcoholic, with a few days over 19 years without a drink as I write this, and I suppose the two tales are intertwined to some extent.

Not that I am a saint by any means, a lot of people with a lot less time have a better sobriety than I. But I learned that alcohol is a poison to me, so I avoid it. I just do irrational things when I add alcohol to my system.

For a while, I blamed my cross-dressing on the booze. But I discovered that feelin... Continue»
Posted by prairieFreak13 1 year ago  |  Categories: Shemales  |  Views: 1061  |  
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Sweet Charity

You may have heard of the phrase sweet charity, well in my case it was certainly sweet to me. I have built up a large part of my CD wardrobe through judicious visits to charity shops wherever I may be in the country. In one of my local charity shops there's an assistant called Wendy who I would judge is in her mid fifties but looking well on it. She's always well turned out in neat blouses, always a just above the knee skirt, never bare legs and 3 to 4 inch heels of various kinds. I must admit that my fairly frequent visits to this particular shop engender a feeling of hornyness on two counts.... Continue»
Posted by MichaelaCD 3 years ago  |  Categories: Shemales  |  Views: 1060  |  
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new job part 3

When I work up in the morning I was alone on the couch. At some point in the night Bethany must have moved to her bed and covered me with a blanket. I looked around the room and saw the remnants of last nights romp. My clothes were in a ball in the corner. Her dildo and harness were on the floor. And as for me, my stockings were ripped, my make up was smeared and my ass was sore and still slippery with lube. I looked like a wreck, but somehow I felt more like a girl than I ever had before. Still I was a bit embarrassed and didn't really want to face Bethany. I tip toed into the bathroom and lo... Continue»
Posted by cinful6767 9 months ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 1060  |  
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stranger at a hotel

this is very true,few years back my mother passed away,left me a bunch of money,afterward,i now had money,but no f****y,so i was wild,parting,having alot of,hot man sex,by the way,im a chubby,very fem. tan, smooth,i look, act,an love to be treated,like a girl,an love it when a well hung horny man is turned on by me..i was at a riverboat casino,staying at a very nice hotel..i always,had plenty of very sexy,outfits an loved to dress up an leave the curtains,half open (pretending i didnt realize it)an just like a worm on a fish hook,sure enough someone would walk by an see me as i was,walkin arou... Continue»
Posted by burds67 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1062  |  
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A Sissy Slave for a Transvestite...continuation

Gwendolyn giggled and hung up the phone and begin to grind more exuberantly as her penis harden. Gwendolyn rode me for nearly an hour, my bung hole was full of her seed and made obscene sloppy sounds before she stiffen and flooded my bung hole once again. Gwendolyn laid there for a little while before pulling her flaccid penis from my bung hole and admired her handy work. '...Look at my cum oozing from your pussy, my girls are gonna luv you boy. I've got to get cleaned up, just relax, I'll be back for you in a sec...'

Laying there, feeling Gwendolyn's spunk seep from my ruptured bung hole... Continue»
Posted by d4david 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1059  |  
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Once a Slut Always a Slut

I held my breath – and then I knew I had crossed a line – I had become by my submission, in that instant of time, another individual.

I had known Paul Phillips since I had arrived at the local school in the village some 6 years before. We had moved on together to the grammar school in a nearby town a couple of years later. We had been sort of friends from the start but as we grew older he became one of the ‘in-crowd’ and it seemed everyone sought his company and approval – for why I am not entirely sure but perhaps it was that he was a keen sportsman; good-looking bloke with an acerbic wit... Continue»
Posted by charlottekerscot 3 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 1059  |  
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You Just Never Know... ya know?

I was out on the road, On my way to Montreal at the end of my stint behind the wheel. I pulled into a roadside rest area, or lay-by... or in this case a 'pickle park', a cruising area for local and tranient gay and bi-men looking for a quick NSA hook-up. Hell, so was I.

I was all nice and clean from the shower I'd had an hour ago at a fuel stop, and I was ready for almost anything now. I waited for a bit and sure enough, a girl walked up beside my truck from out of the shadows, and asked me for a light for her cig. Her voice gave him/her away, and we chatted for a little while.

Short... Continue»
Posted by crochetteDave 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1057  |  
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My Boi Trish

This is a true story about a young lover whom I will call "Trish".

I attended a Halloween party several years ago. There I saw a cute boy who worked in the same retail store I did. He was all hussied up like a gypsy (still think of him whenever I hear that song by Fleetwood Mac). He had a very smooth, lean body and I think his ethnicity was middle-eastern. Nice almond skin and jet black, shaggy hair, very thick. Anyway, he kept giving me the eye all through the night until I finally walked over and said hello. We chatted about work and other things, etc. until he finally pretended to drop o... Continue»
Posted by RazedGlory68 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1057  |  
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He makes me feel so GIRLY

My friend that you all see fucking me and me sucking his big cock in my pics and videos. We will just call him Mister. Well he came over this morning for some Sunday fun. He is so good to me he really knows how to make me feel like his girlfriend. Today was so yummy I am still sexually excited just thinking about it.
I was dressed and ready for him when he arrived. I was wearing my sexy white lace halter top and black thigh high stockings, with the cutest little white G String with a sexy little flower in the back. Topped off with my silver jewelry and 6 inch black heels. I was so excited to... Continue»
Posted by Naughtynina 3 years ago  |  Categories: Shemales  |  Views: 1055  |  
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My dream encounter with a tranny

There is nothing more hot than to have a slim, pretty body on my hands to fondle. To feel their erections starting to grow and to taste their cocks in my mouth. I lose control when I'm around a shemale.

I have fantasized a lot about getting fucked for long periods of time and in a lot of different positions. Unfortunately, all my shemale hookups have been with e****ts that do the deeds rather quickly and then leave. I still have to find a shemale friend to spend long long hours either fucking, fondling or sucking.

I dream about a hot, slim, tender shemale arriving at my doorstep. She beg... Continue»
Posted by feinor11 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1055  |  
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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: 1054  |  
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How to fuck a femmecock in pantyhose

I was so nervous, it was actually happening. I was finally going to meet Daddy Blkice! I had rented a cheap motel room for our first date. I was dressed in sheer to the waist black pantyhose with sheer black thigh highs with lace tops over them and a garter belt like daddy asked. I painted my sexy toes red because I know how much daddy loves my toes painted red. My tight little black dress matched my stockings perfectly. I knew daddy would find me irresistible in it. I had just finished putting on my makeup and blonde wig when I heard a knock at the door. It was daddy! I started to tremble wit... Continue»
Posted by whawha1976 10 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1054  |  
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the real me part five

Well mom and Becky left the room.I sucked Mike and let him fuck me in every postion could think till we fell asl**p.I didn't sl**p to long and got up to go get a drink down stairs.As I walked down stairs my well fucked hole felt loose and very wet and i loved it.
I went into the kitchen figued I'd make pot of coffee since I couldn't sl**p and was on cloud 9.Well I my mom came in the only thing she had on was a black gartor belt and black fishnet stockings an heels.She laughed a bit and said,dam hun you smell like just like sex.We talked while coffee was being made.she was sitting on the tabl... Continue»
Posted by cdpaula 2 years ago  |  Categories: Shemales, Taboo  |  Views: 1053  |  
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Crossdressed and 2 salesmen come by

Imagine your expecting a salesman to drop by at noon to show you some samples of wallpaper-You start your shower at 8 AM-you finsh up by shaving your legs real smooth-you go and put on a pair of full cut thin strechy full cut skimp skamp white panties-next you pick out a lovely open girdle and pull it on and attach your suntan colored stockings-the ones with the shiney look-you pull them up real tight-then your thin see thru bra and your size dd silicon titties the ones with the big nipples that stick strat out-then a thin strechy spandex-lycra slip dress-a long brown wig and a pair of your 4... Continue»
Posted by tvdomm 2 years ago  |  Categories: Mature, Shemales, Voyeur  |  Views: 1052  |  
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