Tranny Night Out free porn video

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Tranny Night Out and One Kinky Session
Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot
of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were
long term friends.
I knew something was wrong but never worked out what it was till one evening whilst dating a girl
named Becky I had met on an online dating service who seemed to accept me for who I am.
We had been dating for 3 months or so and I always loved the feel of her stocking clad legs and
seeing her in sexy lingerie, but I secretly was always thinking about how good the items would feel
against my slim torso.
I was not sure if she knew that I secretly craved to become a girl in secret and she definitely did not
know about the times I had worn stockings while playing with myself and stroking my thighs encased
in silk.
One evening as we sat cuddled up together going through our local paper she saw an advert for The
Rocky Horror Picture Show coming to our local theatre. With that she asked if we could go and I felt
suddenly in a state of shock especially as I knew all about the cross dressing bit of going to the show.
Eventually I agreed we should go and she suggested that I go in drag as a convincing girl, of course I
wanted to but I did not want her to know about my secret. My long time desire to dress like a
convincing girl and be used like a girl too.
The following morning we got up early and called the theatre to book our tickets for the show, have
some breakfast and get dressed before going down to the town centre. On our way down we passed
several lingerie shops and Becky or Beck's as I frequently called her suggested we go into one of them
and look around.
Again I felt the flash of fear rush through me as I was always uncomfortable in those stores even
when buying lingerie for others let alone for myself, but I submitted to her and followed her into the
store cautiously looking at the store clerks to see if I knew anyone.
As we walked around Beck's picked up a couple of Basques for herself holding them against her slim
body and asking me if I liked them, of course I did. I loved my girl in lingerie but always wanted to be
in her place.
We continued around the store for a while with Beck's picking up several items she liked, by now I
was relaxing a little and looking forward to not only heading down to the pub for a sly pint shortly but
seeing the gorgeous Becky in her lingerie when we got home.
Then she caught me totally off guard with a question asking me "Anything you like for our night out?"
I stammered slightly with night out, huh what and she reminded me I was to go in drag to the show
the following weekend.
I was in a place full of lingerie and I was scared to death of what may come of me not only looking at
but buying lingerie for myself but Becky carried on with you will need something to wear as mine wont
fit you.
With that comment the attendant looked up at us both, she was a slim blonde and probably a local
student. Now I was really nervous as she stood there behind the till. I knew she was the only one who
would know for now apart from my girlfriend and she was encouraging me to cross dress.
I knew what I wanted though as I had already spied a gorgeous sating black and purple Basque I
really liked so I told Becky and she agreed it was sexy. After picking my Basque she helped me to pick
my panties and found a gorgeous pair in black lace with little bits of lace in the same purple as the
Basque. Little did she know I was actually semi hard in my briefs thinking about dressing like the girl I
had always wanted to be.
With that we paid up at the till with Beck's making a comment to the young blonde that we were going
to the Rocky Horror Show and she was going to turn me into a girl for it. The blonde behind the
counter just laughed lightly and took our money before we decided to leave.
By now I was ready for my Sunday lunch time pint and a paper to check the football results but Becky
had other ideas. She carried the bags from the lingerie shop but insisted as we walked down the hill
that we should stop off at a shoe store, it was nothing special. A cheap kind of everything on display
shop so no attendants to worry about till you had to pay and they were not bothered by what was
going on in the shop as they were to busy discussing their night out and who they had shagged.
Becky dragged me down through the store to where the woman's high heels were located and she
instantly picked up a very sexy pair with ankle strap and a good 5 inch heel in patent black, I even
told her how sexy she would look in them. Then as I had guessed she told me to select a pair in my
size.
I was starting to get used to this now and it was obvious she wanted to turn me into her girl for the
night, with that I picked up a gorgeous pair of black peep toe heels with a modest 4 inch heel. She
agreed to them and told me they would look good with my Basque as they had a colored sole as well
in purple.
I had to have a minute to myself so as Becky went to pay I left the store and sat on a wall just outside
the door waiting on her to join me.
A couple of minutes past and she appeared from the store and came over to give me a kiss, as I did I
felt the throbbing of my cock again and she sensed I was turned on already at the thought of dressing
and being with her fully dressed.
By now I was not only becoming more broke by the minute but I really wanted my lunch time pint to
settle the nerves so we walked on and into our favorite pub. We sat at a table near the bar so I could
watch the football results from the early games coming in. As I sat nursing my beer a waitress by the
name of Emma we both knew came over to say hi and Becky just could not resist telling her we were
going to do the Rocky Horror evening. To my surprise she told us that she and her boyfriend were
going to and she was also going to dress him up.
For me this started to sound interesting and Becky seemed to know that I would be more chilled if we
went as a four some of sorts, and to be honest me and Emma had a bit of history as we had some
casual sex before she got with her current guy Marc.
Marc knew of our history but Becky had no idea I used to drink there and wait for Emma to finish so
we could go have sex either at mine or in one of the two swingers clubs in the town hidden away. She
also knew I was bi and had seen me engaging in oral sex with other guys in the clubs.
With a sly wink in my direction she went rushing off to deliver the next hungry punter their dinner and
then the question came from Becky.
Why did Emma wink at you as she left?
I knew I had to tell her so I told her straight that I and Emma used to have a casual arrangement
before me and Becky had met or got together at least. To my surprise Becky was totally cool about it
all although she had no reason to not be. Of course I had neglected to tell her about the guys I had
sucked off in the swingers club near my flat in town.
After an hour or so we went to leave the bar and Emma came bouncing our way asking if we could
arrange a good time to meet up on Saturday for the show. As Becky now knew mine and Emma's
history she suggested that Emma bring along Marc and the girls dress us boys at my flat as it was
only a 5 minute walk to the theatre in town.
With that we all agreed that around 6pm on Saturday would be best and then we could have a few
drinks to relax before dressing and going out.
I knew Becky would be feeling a little odd meeting a girl she already knew but not knowing I used to
have regular sex with so I put my arms round her pulled her close and kissed her telling her she was
gorgeous. With that we were back to normal and I gave Emma a peck on the cheek and left.
As we were walking back to the flat I knew there was a wig shop round the corner from my place as a
lot of the towns transvestites used to use it to get there hair pieces. My flat was after all on the edge
of the town's gay area so you always saw an interesting mix of people around. I always loved living
there and it was easy if I ever got up the courage before meeting Becky I could walk just down the
road and go to a gay bar on the pull for convincing trannies.
Becky agreed she should tag along to the wig shop and as it was mid afternoon on a Sunday they had
closed but left a mobile number on the door. I was unsure but Becky told me to call it as we needed to
get sorted and did not have time in the week due to work.
I hesitantly called the number and what sounded like a gay guy answered and told me to wait 2
minutes and he would come down to help us. I was kind of surprised that a gay guy should be running
a shop basically for trannies. The shock did not last long though as a leggy transvestite came to the
front door and unlocked welcoming us in and locking the door behind us.
In fact the Trans girl who ran the shop was actually very convincing and I found myself checking out
her bum as she showed us round the styles she felt would suit me. In the end I picked a raven black
shoulder length wig that fell over the edge of one eye. It made me feel so girl like and once again the
bulge in my briefs came back. This time I was not the only one aware of it with the trans girl who ran
the shop clocking my package and telling Beck's she was a very lucky girl to have such a nicely hung
man or girl to fuck her.
We found that the Trans girl running the shop called herself Vanessa and Becky found her not only
amusing but admitted to me later that she would love to have sex with her. This turned me on even
more as if she liked Vanessa did that mean she would like me as a girl?
As Saturday evening came round the buzzer for the front door went just after 6pm, knowing it would
be Emma & Marc I bounded downstairs with a bottle of lager in hand to meet them.
Emma looked sexy as ever and I invited them in shaking Marcs hand along the way. I guided them up
the stairs and down the corridor to our comfy lounge full of big soft leather sofas. Emma and Marc sat
across from me and Beck's for a bit enjoying a drink and each others company.
After a hour or so the girls went off to our bedroom to get ready and I slowly started conversation
with Marc, as it was the first time we had met the conversation revolved around football, beer and the
girls. He then built up the bottle to ask about me and Emma and I told him that it was a friendship
and casual sex pact we had made but it had since ended due to both of us meeting partners since.
He also mentioned that Emma had told him I was bisexual and I waved my hand at him to keep it
down as Becky did not know. He replied with that's cool I am too. Now the party was really looking up
as Becky had expressed an interest in Vanessa from the shop before so I had to wonder if she had
ever enjoyed another woman sexually as I knew Emma was bisexual and very kinky too.
What seemed like hours passed as Marc and I sat chatting about all sorts and then the girls came
walking in. Becky in a black lace Basque and panties with stocking and her new 5 inch heels, her dark
brown hair falling to her shoulders with the tips of her hair brushing the tops of her pert 38B cup
breasts. Emma looked just as stunning in a PVC corset and panties set with black hold up stockings
and 5 inch stilettos on.
I could not keep my hands of Becky and patted my lap for her to come and sit on, she took the hint
and Emma did the same for Marc. Trying to be discreet I ran my fingers across her clit finding her to
be moist already. With that she bent to kiss me and whispered into my ear that Emma had licked her
out. My thoughts previously had been right she was bi and we were going to have a lot of fun later on.
What I did not know is that Emma had told Becky I was bisexual and so was Marc but again she
whispered to me that she now knew and could not wait to see what may happen later.
With that me and Marc went to the bedroom to put on our lingerie and as Marc lowered his briefs I
could not help but look at his cock and him at mine. Before I knew what we were doing we were stood
slowly wanking each other off. He had a lovely thick 7 inches that I knew I could deep throat if he
wanted me to. I complemented him on the size of his member and he jokingly said it's not as big as
yours though and he was right as I had 8 1/2 inches of thick cock rock hard and ready for him if he
wanted it.
We left each other alone after that and started to dress but soon found the sensation of slipping into
the Basques and stockings too much. I noticed his cock straining at his panties so dropped to my
knees in my wig, heels and lingerie and started to slowly suck him deep into my mouth. He stood
there fully dressed moaning with pleasure as I flicked my experienced tongue round his bell end. He
soon pulled away from me explaining he wanted to save his cum for later and helped me to my feet
before he released my 8 1/2 inches and began to suck on me. He was obviously experienced as he
really knew how to suck cock and I felt rushes of pleasure passing through my body.
I thought for a while I was going to explode into his mouth but held back as he had explaining I
wanted to save it for later on. As he stood and we both relaxed and put our cocks back into the
restrictive panties I asked if he had ever had full sex with another guy, he replied he had but only
liked to give and not take cock in his anus but did add he may if he was relaxed enough.
As we were now both fully dressed we ventured into the lounge again to meet the girls and as we did I
saw Emma on her back on the black leather with my Becky licking her pussy deeply. They both
seemed to be enjoying each others juices already. With a start Emma told her to stop as she saw me
and Mark stood watching both with rock hard cocks waiting for them.
Becky jumped to her feet and trotted across to me and kissed me full on the lips, her mouth tasted of
a taste I knew well Emma's pussy. With that she took my hand and said lets go do your makeup.
Emma and Marc did similar but after a couple of minutes we heard a loud groan from the lounge. I
was told to stay where I was and Becky went to investigate, it turned out Emma had been sucking
Marc off and he had cum hard into Emma's willing mouth.
Soon I was fully made up and looking convincing thanks to Becky who confessed she wanted to get
fucked by me looking like a girl. I had no plans to fuck her before going out but she told me she
needed my cock in her.
With that I stood slid down the panties and sat back on the stool, Becky wasted no time in mounting
my rock hard cock and riding me while sliding her pussy soaked tongue into my mouth. I just could
not take anymore with the feeling of her dripping wet pussy wrapped round my shaft and the taste of
Emma's pussy in my mouth and I convulsed hard and shot my spunky load deep into Becky's willing
shaved pussy.
She sat for a moment taking it the fact I had just shot my hot load into her and get over the orgasm
she had as I did so. She kissed me lightly and rushed off to the bathroom to take her pills as neither
of us wanted her to get pregnant yet anyway.
The time had soon come for us to go out to the show, it was dark and cold on the October evening
and as we turned the corner we ran into Vanessa from the wig shop who complemented me and Marc
on our look. We asked where she was heading and it turned out she was going to the show with her
boyfriend, a hunky muscle bound gay boy called Phil. He was stunning but scary to look at but oh so
sweet and soft if truth be known. He was also a tease as he grabbed my bum as we walked down and
got told off by Vanessa for not looking after her.
I was so aroused not just because Phil had grabbed my bum but being dressed and out on the town
with girls, a guy and two other trannies.
As soon as we got to the show we took our seats and waited for the curtain to open and lights to dim,
as they did I felt a hand in my groin stroking my cock through my panties only to discover it was my
gorgeous Beck's, I reciprocated the gesture by slipping a finger round the hem of her panties and
stroking her clit. I felt her starting to get wet for me again and she moved my hand away and
whispered to me that I was in for a show when we got home.
As soon as the show finished I could not wait to get home and Emma & Marc joined us, not to be rude
I invited Vanessa and Phil too but Vanessa said they were going elsewhere for some fun with some
friends but agreed we could meet for a drink another time if we fancied.
We soon reached the front door and all headed fro the lounge, I and Becky had a couch and Mark &
Emma had the other across the table from each other. We all knew we were going to fuck together it
was just who would make the first move. I felt the tension building in the room and decided to trot off
to the kitchen in my heels to find a cold bottle of Champagne I had purposely put into the chiller
before we left.
Heading back to the lounge I heard light moans coming round the door I saw Marc licking out Emma
in front of Becky. To add an element of surprise I popped the cork on the Champagne and tipped a
little into Emma's pussy as Marc lapped it up.
The rest I poured into 4 glasses on the table but made sure I kept a little as I planned to give Becky
the same treatment, she was already fingering her rapidly moistening pussy as I pulled her panties
aside and slid my tongue into her waiting clit. She knew what to do as she took the bottle of
Champagne and poured a little over her wet cunt as I lapped at her making her orgasm hard from the
cold Champagne running down her clitty followed by her girly love juices and saliva.
Emma had crawled over to us and kissed Becky full on and dropped to her sopping wet pussy and
began to lick her out again, soon they were in fits of passion as they 69'd each other lapping at each
others pussys.
I suddenly knew what I had to do as it was obvious Marc was not going to initiate the fun between us
so I crawled on hands and knees across to him and knelt in front of him licking my made up lips.
He knew what I wanted and released his cock from his lacey panties for me to suck on, I wasted no
time in sucking his lovely thick cock deep into my throat, as I felt his cock start to throb I stopped and
got up from my knelt position and told him to get down on his knees and suck me off. He knew what
to do and expertly got me rock hard, lapping up the pre cum off my stiff cock.
Little did he know what I wanted and I pulled him to his feet, kissed him hard and asked if he would
fuck me. He agreed he would love to fuck my tight arse and bent me over the couch and expertly
flicked his tongue across my puckered asshole. I was rock hard as I felt his tongue driving into my
tight arse.
Soon I felt his helmet pushing against my love hole and a cold sensation which turned out to be cold
lube dribbled across my anus. Soon I was in pain as his fat helmet eased its way into my anus, slowly
sliding into me inch by inch till I felt his balls against my arse.
From across the room I heard Becky say go on fuck his arse, I want to see you fuck my gorgeous
tranny girlfriend and with that he proceeded to start banging the arse off me sliding his thick 7 inches
in and out of my arse. I loved it, I felt like a total slut getting banged in front of two girls I had fucked
before. One of which her boyfriend was now slamming his cock deep into my arse.
After what seemed like all night long he pulled out of me and I felt a bit of relief as he did, I knew he
only liked to top others so was suddenly surprised when he asked if I would fuck him now.
I secretly had fucked trannies before and knew exactly what I was doing, I warmed the lube between
my fingers while I rimmed him hard, sinking my long tongue deep into his arse. I knew I had him nice
and relaxed so I slowly lubed my 8 1/2 inches and his anus pushing the lube deep into his arse.

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Tears of pain pricked my eyes as Julia drove her huge black cock into my ass. In my wildest dreams I had never expected myself, an all-American straight white male to be in this situation, beaten, bound, and being ass-fucked by a transsexual with a huge cock.I am a normal sort of person, happily married, with two k**s, and with normal middle-class values and behaviour. I don't hate gays or blacks or anything like that but I don't want them in my neighbourhood. My only fault is that I cheat on...

3 years ago
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Tranny Attack

Tears of pain pricked my eyes as Julia drove her huge black cock into my ass. In my wildest dreams I had never expected myself, an all-American straight white male to be in this situation, beaten, bound, and being ass-fucked by a transsexual with a huge cock.I am a normal sort of person, happily married, with two k**s, and with normal middle-class values and behaviour. I don't hate gays or blacks or anything like that but I don't want them in my neighbourhood. My only fault is that I cheat on...

2 years ago
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Tranny Gas Station Attendant

This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intimate, but I consider it just sex. When I say I'm not intimate with other guys, I mean I don't kiss or cuddle or anything like that. It's always just sex, with no strings attached.......usually! There...

1 year ago
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Tranny Surprise

When I left my high school, I decided to go on a gap year and travel the world to see lots of interesting people and ways of life. My first stop was Thailand which was great and I had so much fun partying with my friends as around 5 of us went on the trip. After Thailand the next stop was in Brazil and due to the time of the year the nightlife was truly amazing. We had decided to stay in a rather swanky hotel as this was a dangerous place from what we heard from the guides and people there. The...

She Males
3 years ago
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The Knight and the Acolyte Book1 Chapter 7 The Knights Sacrifice

Book One: The Quest Chapter Seven: The Knight's Sacrifice By mypenname3000 Copyright 2016 Note: Thanks to B0b for beta reading this. Acolyte Sophia – Western Deorc Forest, The Federation of Deoraciynae The two other elf hunters appeared silently out of the woods. Like Xera, they were gorgeous, tall and lithe, their bodies painted in greens and browns to let them blend into the woods. Their keen eyes flickered at Angela and me, their ears twitching in obvious curiosity at the sight...

1 year ago
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Trannys Feminize Dandy Boy Sequel

So being feminized is a sort of intimate experience? Believe me it's more than that! In fact I don't know how I can say everything about how I feel now or then when it started happening to me. But that's how my life goes. Things tend to get done to me. However much I try to regain control of my life I find others dominate me. For those of you who haven't read my story so far it is basically this: I was an effeminate schoolboy and all my friends knew I was not cut out for macho things. Then one...

She Males
2 years ago
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The Knight and the Acolyte Book 10 Chapter 4 The Knights Resolve

Book Ten: The Flaming Woman Chapter Four: The Knight's Resolve By mypenname3000 Copyright 2017 Aurora Xandra – Unmik, Asunow Princedom, The Princedoms of Zeutch The alarm resounded through the cell, my delicate ears flinching from the piercing reverberations while the smile grew and grew on Princess Adelaide's face. The strawberry-blonde woman shuddered on Chaun, eyes casting to the ceiling of his cell. My stomach twisted with fear and anger. She triggered an alarm. She had just...

1 year ago
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Knight and Dey 3 Meet the Knights

{Because of something that happened in "Lost Indian Caves" before he was born, Alex's has a condition that changes his gender; male in the dark, female in the light. Alex's simple goal is complicated by a power struggle within the first school he's ever attended. That struggle is about to take on wider implications. - WARNING: This story has been heavily manga influenced.} Knight and Dey 3: Meet the Knights By Ron Dow75 Out in the outer office of school administration, police...

Humor
4 years ago
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Tranny Attack 2

Thanks for the great feedback. Here is part two. I encourage you to send in more ideas of what you would like to see happen. “You’ll be hearing from me again, sweety!” With those words Julia had kicked me out of her apartment. I dragged by bruised and ass-fucked body home. Thankfully, Jane was not back as yet. All through the journey back to my house images of the previous night kept playing through my head. Discovering Julia’s cock, of being tied up and buggered, of sucking her cock, and...

3 years ago
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Tranny Sex Therapy

All at once, Maria’s limp lady stick transformed itself from lifeless shell into The Incredable s/he Hulk. I had to keep opening my mouth to keep it all in. Precum started to pour down my lips and chin onto to my bra. That precum was rapidly replaced by genuine girlie man paste. I would have been laughing but it was like being water boarded with seamen. I was drowning in hir cum. Holeee SHIT! ******************************************************************************** I swear I should...

4 years ago
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Tranny Attack Ch 02

"You'll be hearing from me again, sweety!" With those words Julia had kicked me out of her apartment.I dragged by bruised and ass-fucked body home. Thankfully, Jane was not back as yet. All through the journey back to my house images of the previous night kept playing through my head. Discovering Julia's cock, of being tied up and buggered, of sucking her cock, and of having Julia piss on me. And it was all on camera! And who had she sent the videos to? If she blackmailed me, what would I do. I...

4 years ago
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Tranny Secret Story

Hi indian sex stories dot net readers This is a secret story of a transsexual. What is different about this one is that ,unlike the usual trannys who are females supposedly trapped in male bodies, this is about a male trapped in female body. Shankar is one such person, about 26 years of age. He is tall,young and handsome with a dark mustache ,contrasting his fair color. he started dating Ramya who worked in a software company.He worked in one of the automobile companies in Chennai in the HR...

2 years ago
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Tranny suck me off tv ts cd

I have a new found love for trannys I love convincing polling tv,ts and cds. The other night i met a tv from Halifax a town close to my home town. Wed arranged a meet online I d agreed to pick her up on a street corner like a cheap street walker. I pulled up at the side of the curb and a woman stepped foward from the shadows tall long sexy legs blonde hair, short skirt, fishnets , high heels and a figure to die for. Leaning in the window she asks one question are u hard for me baby. My reply...

2 years ago
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Tranny Sex Therapy

All at once, Maria's limp lady stick transformed itself from lifeless shell intoThe Incredable s/he Hulk. I had to keep opening my mouth to keep it all in.Precum started to pour down my lips and chin onto to my bra. That precum was rapidly replaced by genuine girlie man paste.I would have been laughing but it was like beingwater boarded with seamen. I was drowning in hir cum. Holeee SHIT!********************************************************************************I swear I should have...

4 years ago
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Nightout

Standing outside the club, daring myself to go in, I just wished the local t-girl I was to meet hadn't cancelled. It seemed a great plan...on solo holiday in the Algarve going to a gurl friendly club with a local who knew the place. Right I'll go in for one drink so my night wasn't totally wasted. Inside the club was fairly busy with a long bar ahead and booths lining the walls. I walked carefully over to the bar...didn't want to trip up in my stilettos. A friendly barmaid took my...

4 years ago
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The Knight and the Acolyte Book 1 the QuestChapter 7 The Knights Sacrifice

Acolyte Sophia – Western Deorc Forest, The Federation of Deoraciynae The two other elf hunters appeared silently out of the woods. Like Xera, they were gorgeous, tall and lithe, their bodies painted in greens and browns to let them blend into the woods. Their keen eyes flickered at Angela and me, their ears twitching in obvious curiosity at the sight of two humans in their woods. I was still naked. It was wonderful to not have to wear the robe. As an acolyte of the Temple of Pure, I had...

1 year ago
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Trannys Feminize Dandy Boy

"Yea I thought the singing was OK but I don't really go for that style too much" "And the girls?" Brian prompted me. "Oh come on Brian leave him alone we all know he's not really interested in girls." "Give him a chance, people can change! Perhaps Carl's developing an eye for them now eh Carl?? I mean they weren't bad looking. So, apart from their style what did you think of them?" I was together with Mike and Bryan and a number amongst many of my old school friends. The local pub had got in...

She Males
2 years ago
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Tranny in Toronto Chapter 5

When we found ourselves alone at the party and grabbing food in our friends kitchen, Helen and I began small talk. She asked if I was transgender. I told her the truth, that yes I was and asked how she knew. She said that she would never have guessed that but Luci (our mutual friend) had told her. Before I could say anything, she said, "it's fine, I love that you're talking to me and you look amazing, would love to see that body in action!" I smiled. She asked what I did for a living and...

2 years ago
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Tranny in Toronto Chapter 3

There were lots of Indian people at the intersection of Brimley and Lawrence walking by shopping at the nearby stores. I wondered how their lives were doing. It was almost Winter 2012, snow would be falling soon. I watched as a white Dodge Caravan pulled up towards the Tim Hortons. I quickly took out my phone and wrote down their plate number as they parked in the small parking lot beside the Tim Hortons. Two men came out, both brown males, around 30 years old, short black hair and brown...

2 years ago
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Tranny In Toronto

Married Couple Looking For Fun Time - mw4t - 40's (Toronto) We are a married couple, looking for a bisexual trans for some fun. We host. Message if interested with times you're free. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ To: [email protected] From: [email protected] Subject: Re: Married Couple Looking For Fun Time - mw4t - 40's (Toronto) Hi, my name's Lizzie Elliott. I'm 18 years old, a m2f trans looking for fun. I'm safe and clean....

2 years ago
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Tranny by the pool

Walking past Chancellor and heading straight for the bar, Amber fixed herself a drink. She tossed her oversized purse down and excused herself to the ladies room to freshen up a bit. Chance was waiting for her by the pool, one leg on the side, one leg in the water, casually stroking his stiffening cock when she returned. Amber emerged, freshly applied lip-gloss shining in the sun, her smooth brown skin looking like a Hershey's chocolate bar and her bathing suit bottoms were filled out to...

4 years ago
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Tranny Pickup

on Chicago's state street. At the moment his trousers and shorts were around his ankles, his dress shirt was pulled up and he was reclining in the girls couch. But something wasn't quite right. He was beginning to suspect that the she whose mouth was engulfing his cock was really a he. Paul was in the bag thought, and after all 'lips are lips.' What ever the gender Paul was getting the blow-job of his life, she was sucking his nuts, alternately with deep throating him. The...

3 years ago
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Tranny In Toronto

Introduction: Read My Intro Story First Before This. Click on my profile name and youll see it. Craigslist Ad: Married Couple Looking For Fun Time – mw4t – 40s (Toronto) We are a married couple, looking for a bisexual trans for some fun. We host. Message if interested with times youre free. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ To: [email protected] From: [email protected] Subject: Re: Married Couple Looking For Fun Time – mw4t – 40s (Toronto) Hi, my names Lizzie Elliott....

3 years ago
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Tranny Surprise Part 2

Things were off to a good start with Dani. We have been texting each other throughout the week just talking and setting up another date. We decided to go to the local fair I picked her up around 530 and she wasnt quite ready yet so she let me in hugged me and went back to finish her hair. I sat on the couch and played with her cats for a minute, she was back in no time and she looked great! ‘Wow Dani you look really pretty in that sun dress.’ I said. ‘Thank you’ she replied with a big smile....

4 years ago
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Tranny in Toronto Chapter 5

Introduction: Hello everyone, I apologize for not writing any recent / new stories. Ive been really busy with stuff. Heres a quickie. Helen is a good friend of mine. When the following occurred, Helen and I had known each other for only a couple of weeks. We met at a party a mutual friend of ours was hosting and we instantly connected. To describe her, she was smoking hot. She was a blonde in her late 30s with piercing blue eyes, huge tits, firm ass and I believed to be a closet lesbian. She...

1 year ago
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Tranny in Toronto Chapter 3

Introduction: Read Past Stories Before This One. I stood outside Tim Hortons with a small coffee in my hand, sipping away on a cool windy day. I looked at the cars driving by me, just waiting for the white van to show up. Two men from Craigslist messaged me and asked me for a Sunday afternoon fuck. I agreed to my first MMF threesome. They called it a MMT threesome and were really excited to fuck a prostitute, and not only that but they wanted a shemale really badly. They told me to come to...

2 years ago
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Tranny Surprise Part 1

After being cheated on for months here I am alone in a bar having a drink. I dont understand whats wrong with me im above average in looks, im fit, im successful for my age. Its time I move on though and so far no girls ive dated have been worth a second date. As I look around the bar I see her. I immediately start to stare. Looks like she was there with a couple of her friends. I order another beer and decide to scope it out for a little bit. I just couldnt get over how pretty she was. She...

4 years ago
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Tranny used in the woods

I just had to share this as I realised one of my ultimate fantasies at the weekend.A couple of weeks ago I met a guy online (Mark) and we met up and had some fun together. A few days later he got in touch again and said he was going dogging and he wanted me to join him. I do this from time to time, so we made arrangements to meet at his house for me to get ready and then go out on the Friday night to a known dogging location not too far away.I thought it was going to be just the two of us, but...

3 years ago
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Tranny girls craiglist fun

My name is Jack, I’m an average enough 18yo guy. Perhaps in a physiological sense, I’m more feminine, I have shoulder length blonde hair, and tranquil blue eyes. Coming from my father’s side of the family. My mother seemed to give me her own felinity. I have little to no hair body, my voice was higher than average, and I suppose I was kind camp. Ohh, I also had a cute and tight little bubble butt. However, by night I was far from average. Porn always had fascinated me. Initially the classic...

4 years ago
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Tranny Surprise Part 2

Things were off to a good start with Dani. We have been texting each other throughout the week just talking and setting up another date. We decided to go to the local fair I picked her up around 530 and she wasnt quite ready yet so she let me in hugged me and went back to finish her hair. I sat on the couch and played with her cats for a minute, she was back in no time and she looked great!"Wow Dani you look really pretty in that sun dress." I said. "Thank you" she replied with a big smile.We...

3 years ago
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Tranny Surprise Part 1

After being cheated on for months here I am alone in a bar having a drink. I dont understand whats wrong with me im above average in looks, im fit, im successful for my age. Its time I move on though and so far no girls ive dated have been worth a second date. As I look around the bar I see her. deleted

1 year ago
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Tranny orgy continued

Debbie, my red haired, large titted, big hipped, cock sucking, golden bushed girlfriend now knew I loved to suck shemale dick and having them fuck me in the ass. Sex between the two us became more intense and we were often joined by the gurls across the hallway. Life was good and shortly Tanya and Bonnie informed us they were having a party that would include Shemales, sissy me and cross dressers. It was to be an orgy! On the night of the occasion, we were the first ones there. I wore a speedo...

4 years ago
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Tranny orgy

You can live with someone and never really know them.I was running a car wash in West Palm beach and every day I would take lunch at a cafe down the Blvd. The food was good, and cheap and I had the hots for Debbie, this built to the hilt redhead chick working there. She wasn't any great beauty but she had a body to die for. 36 DD tits. big hips and thick legs. Just my type. After a couple weeks I got the nerve to invite her to TGI Fridays for some drinks.After a few, she started talking about...

4 years ago
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Tranny Dogging Experience

Not my story as i'm a proper woman lol but i just loved reading this...................I am a 24 year old male to female transsexual, I have been dressing up as a a woman since I was 14 and had nylon led sexual fun since my early teens. Often wanking myself whilst wearing a pair of sheer stockings. The result is that today I have a very large wardrobe of clothes and shoes, I am completely smooth all over apart from a landing strip and have manicured nails and shaped eyebrows and with killer...

2 years ago
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Tranny teacher

Hi Al, how is your house sitting summer going ? Pretty good Tim a little boring but the beach is nice. By the way, I didn't mean to but I saw you last night through my window... you were wearing woman's underwear. OH I hope I didn't disturb you Al. Actually I was totally turned on, especially when you pulled out your hard cock. Really, if you like I can arrange for a private show ... interested ? I don't know I have never seen a man up close before. Ah.. well if you pretend I'm a lady I can...

4 years ago
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Tranny Slave to BBC

I took a drag from my cigarette as I waited on my ride to appear. Looking around it was pitch black outside with only a waning moon and a few stars to light my way in the night. I had been waiting for about ten minutes when headlights finally appeared on the road in front of me, illuminating the sidewalk I was standing on and the stop sign beside me. I could barely contain my excitement. I had been waiting for this moment for a while. I had been fantasizing about it for around five years and I...

2 years ago
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tranny

Let me tell you a little bit about myself I'm five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the parking lot. There were several men beating up a beautiful woman, when I tried to break it up I ended up getting very banged up myself. Her name was misty, she thanked me for helping her and asked if I need a...

4 years ago
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tranny escorts are the best

Being a rather horny fellow who loves to get spun on meth and party, I occasionally had to craigslist and check out the casual encounters section to see what's out there. So after seeing The Hangover 2 and seeing sexy transgendered girls it got me a little curious to try it out i mean what could i lose they couldnt say no to my 10 inch cock. So doing a big bump my cock was leaking as if i just had a wet dream , I got home and dared to check the T4M section that was so naughty and off limits...

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