Shemales Porn Stories
Page 69

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: 1056  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 1056  |  
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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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Shemale Public Bondage Fantasy

It was a chilly evening, I had arranged to meet him in the city centre. I was wearing a rather skimpy black dress, black lingerie and red high heels. It was my first time dressed in public like this. He was an average looking man, he shook my hand and kissed my cheek, and asked if I was ready. I affirmed, and then he led me to the park in the city. I noticed he had a small bag with him. He opened it and took out several pieces of rope. 'You know what we agreed', he said. 'Yes, I understand,' I nervously replied. I had signed up for an evening of public humiliation at his hands. He led me to a ... Continue»
Posted by barefoottransnude 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1055  |  
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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 7 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1056  |  
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Glory...

I walked into the bookstore paid my way and went into the peeps; I
usually avoid the theatres since there is not any privacy for
playing. I guided my way in the dark letting my eyes adjust in the
dark. I walked to the back where the stalls with the gloryholes are
and found an open booth.

I sat down and pushed to find one of three channels I liked and there
it was the shemale channel, with a sexy shoulder length blonde and
redhead with deep dark red lying on her shoulders. They were kissing
and touching and boy was I getting aroused, so much, so that I did
not notice the booth next t... Continue»
Posted by NaughtyNshy 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1053  |  
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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: 1054  |  
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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: 1052  |  
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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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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: 1051  |  
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Friends cumNgo

I always stayed on the same block, same broken down corner house, same stay to my self attitude, never needed anyone for anything, except my girlfriend who lived with me... we would argue but at the end of the day she would crawl in bed and cuddle til we fell asl**p together. Yes it was perfect for me. I worked early, she worked late, so she'd get home always around the same time while my days fluttered. Yes I made the big bucks so she didn't work as often, but while she was at work i would get my fun out. I have a fetish for femme boys getting sexified in skirts and heels. I've always been on... Continue»
Posted by reefermcrevolver 2 years ago  |  Categories: First Time, Shemales, Voyeur  |  Views: 1050  |  
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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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1048  |  
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Chrissie Learns A Harsh Lesson The Conclusion

Chrissie Learns A Harsh Lesson (The Conclusion)

My arms were stretched straight up over my head, metal handcuffs circled my wrists and were tied to a metal ring that
had been embedded in the ceiling. The rope which was hoisting me up left me suspended from the ceiling in such a manner
that only the toes of my black 4 inch heels touched the floor. The hard metal of the handcuffs cut into the skin of my wrists and
a burning ache traveled through the muscles in my arms and shoulders. I felt totally helpless, totally vulnerable and yet
strangely aroused.
Standing ten feet... Continue»
Posted by chrissieCD 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1046  |  
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CD dream too cum true?making plans True storie

This has always been a dream of mine to do bare back with a few guys same night. Plans are in progress for this fall to make it happen. Have list of contacts from craigs list that i've been posting to contact when I come up with a date and place at a motel close to my home town. September is usualy when I start shaving my body hair again thru spring being all my summer activities are over.

MY PLANS IN PROGRESS-will post movie and story after event.
I have around 30 guys on list and still adding letting them know ALMOST exactly what I'm looking for if we meet, I know only a few guys w... Continue»
Posted by sarahcd_legs 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1045  |  
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Late Night In The Office


It was early spring in London, England. The sky was clear and sunny but there was a cool breeze coming off of the river Thames that caressed Mica’s bare long, slender legs as she stepped out of her sports sedan.
“Oh bugger, why in the world did I wear such a short dress today!” she said, cursing the unseasonable cold day while at the same time trying to hold the hem of her skirt from rising up her legs further then it already had.
Mica Doren started working for Thames Incorporated as a professional administration specialist right after she graduated from a local university, but back then... Continue»
Posted by heatround01 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1046  |  
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new boyfriend and first sex with him

Turns out the guy I sucked in the faculty (college) toilet actually suspected I was a trans and that turns him on. And not only he's into trans he also told me he loves BDSM. I don't have to tell you how great this is, but let's start at the beginning.

The other day after the "toilet incident" I met the guy again. I had white leg warmers, a schoolgirl skirt (I wear these as much as I can), a black tank-top, and a gray hoodie. I heard a voice behind me telling me how beautiful I am today. As I turned around he kissed me. Deep. And with his tongue. My heart raced and I instantly felt an erect... Continue»
Posted by p1llow 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1043  |  
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MEETING THE NEW GURL

Well this happened to me about 10 years ago i was still dressing when ever i could you know shaved body no hair anywhere i'd put on a waist cincher (tie-up corset) gave more hips and smaller waist also added to my tits with inserts and pushup bra with nude stockings, tong, micro mini skirt, with a loose silk blouse and 4 inch heels i was almost passable add make-up and you couldn't tell me from a tall girl anyway i went off to one of our many locations for gays, t/v, t/s, c/d and lesbian bars you know northpark and hillcrest of san diego. it was a saturday night and the place was al... Continue»
Posted by jackguns 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1042  |  
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The Bondage Whore, Chapter 2

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 2 - The Fitting

The next day Rachel arrived at the office. It was mid-afternoon, around 3pm. Today Rachel was wearing her shortest denim miniskirt, too short to completely cover her ass, strap-on heels, and one of her favorite tops which displayed several inches of midriff. Monica greeted her, and introduced her to Phil, who would do the "fitting".

"Come on into my office Rachel." said Phil as he directed her through another door. Monica followed.

Phil was very business-like and proceeded to measure Rachel's ne... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1042  |  
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Sissy Captions Transcribed

Pet had a new assignment last night. Certainly video reinf***ement of her slutty sissy desires was on the agenda. But this time, she used multiple neural pathways for her reinf***ement.

http://xhamster.com/movies/2078893/sissy_boi_gif_training_3_sexy_time_by_dressmeuptoplay.html

A very nice hypnotic trainer, with lots of flashers and captions. But... i wonder? What do ALL those captions really say?

Thanks to pet... we now know.

===========================================

DressMeUpToPlay
Presents
“Sissy gif Training 3, Sexy Time”

Put on a nice outfit and find the nearest coc... Continue»
Posted by dwadd73 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1047  |  
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CHASTE SISSY SELECTIONS

CHASTE SISSY SELECTIONS


"What's the matter, lover boy?" Tanya asked with an amused expression on
her pretty face. "You're the one who wanted to be locked up in that
tight little chastity tube, Billy. I mean, sure, you thought it would
just be for an hour or so, and that I would let you out so we could have
wild sex. But I did warn you that I can be very mean, didn't I? When
we started two weeks ago?" She laughed breathily, a soft and sinister
sound. "So now you're stuck. I've got the key and you're not getting
out any time soon. I like you this way. I also like thos... Continue»
Posted by klammer 6 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1043  |  
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