Shemales Porn Stories
Page 78

Crissie Fucks the Neighbor

It was a Saturday afternoon and I was all alone in the apartment as my roommate Kelly had gone home to visit her
mother for the weekend. I hadn't had a date or been more importantly been laid in several weeks. Needless to say I was very horny.
I quickly flipped through the TV channels and as usual there was nothing worthwhile to watch so I clicked the off button.
I'd already read the days newspaper and even completed the crossword puzzle.
The weather was fairly warm so I was dressed in tight cut off jean shorts and a snug fitting ladies t shirt. Underneath i was wearing
a skimpy leopard ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Mature, Shemales  |  Views: 2662  |  
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MY FIRST BLOWJOB

I met a shemale online called melisa and we had been talking over msn for afew days, mainly having saucy chats about sex and getting off. She asked me to meet her on the coming weekend which excited me as i was a virgin to cock.

We arranged to meet in a bar that was a stone's throw away from my flat, As i entered the bar it was pretty dark and i waited for my eyes to ajust to the dim lighting, then i noticed her sat at the bar wearing a skin tight, dark red dress that was knee high, she looked amazing. I walked over to her and straight away i was struck by a beautiful smile as she turned t... Continue»
Posted by handyman1991 2 years ago  |  Categories: First Time, Shemales  |  Views: 1516  |  
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Chrissie's New Client

I run a small investment consulting firm. Very small, actually it's just me. It's really just a cover business for what I really do which is to service my male clients clandestinely.
There are an average 20-25 active clients. They are all successful proper business man, many of them you would classify as professionals.
They are all referrals and have been carefully screened. Most of the men are straight but just like a girl with "something extra"occasionally. There are also some who I suspect are Bi-sexual. I don't really cater to the overtly gay community.
That's for no particular reason ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1078  |  
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Meeting A Guy on line part #2

We arrived at his hotel going in his room and just as we got in the door he turned taking me in his arms holding me tight around my waist, mine went around his neck and we stared in each others eyes smiling then I felt his hand sliding down from my waist putting both of them on my cheeks under the back of my skirt.
I didn't say a word at first just stood there letting him fondling them squeezing each lobe tight "dam you have a round soft ass" he said I just smiled more putting my lips to his and we embraced in a long wet kiss using lots of tongue.
I could feel his cock starting to get ha... Continue»
Posted by MonicaBond 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1037  |  
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Meeting a guy from online part #1

I had been talking to a guy Jim online for a few months he was white 47 and we got into some very erotic conversations on line and even had phone sex together a few time then we decided to meet,I was all too excited thinking about seeing him in anticipating what both of us knew what was going to happen.
I got into town showered getting cleaned up putting on a short brown skirt with a white top over my very little panties and padded bra finishing my outfit with a pair of three inch black pumps, looking at myself in the mirror I thought I looked cute thinking he was going to like what he sees... Continue»
Posted by MonicaBond 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 836  |  
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HERMAPHRODITE BLACKMAIL

I remember it as though it were yesterday.
19 years old, jut dropped out of college over a sex scandal
with my History professor.
I managed to find a good job in a high end boutique
because I was beautiful, sexy and could pass myself off
as classy, even though I was a cheap whore.
My boss was a perverted dominatrix and immediately
made me her plaything as a condition for my employment.
As long as I obeyed her and serviced her clients.
I was making very good money as a prostitute for rich perverts.
I found a fairly nice apartment, no penthouse for sure
but far from a dump.
I del
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1508  |  
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It started w/the neighbors wife then her husband.

About 5 yrs. ago on new years I was invited over by the neighbors to party, they had some friends over; we were getting plastered and eating food celebrating the New Year. When out of the blue in front of her husband and friends the wife starts kissing me, I gently pushed her away not knowing how the hubby would react, much to my surprise, his reaction was almost as if he didn't mind to the point where it looked like he was turned on by it.
That night after everyone had gone, the husband had been long passed out, we went to my house next door, & I ended up fucking her. I remember her saying h... Continue»
Posted by MyaTranny 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 6414  |  
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double date fun

It was just normal saturday when the phone rang.I answered it an my mom was on other end.She said can I ask you to do favor for me? I depends on what it is.Well she said, you know Cathy (moms lez lover) she called me and ask me to go out on date tonite.I yea so go, she said want to but her son just moved back in with her.I said yea don't he know about you two?Yes he does but we were wondering if you go out with him with us.I said well let me think,she said he very tall handsome an 46 yrs old.I said but does he know I am fulltime crossdresser? Mom paused a minute and said yes he does.I said ok... Continue»
Posted by cdpaula 2 years ago  |  Categories: Mature, Shemales, Taboo  |  Views: 2004  |  
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The Making of a Sissy - Part Twelve

Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as she pulled her indoors.

“Well, you’ve certainly impressed Mr Roberts, and it’s nice to see you with your clothes on again. We are quite the little harlot now aren’t we? We’ll soon have you back down to earth; I’ve lots of chores for you!” Now it was sandy who was downhearted as she drove away fro... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 770  |  
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Encounter In The Park

It was near the end of my junior year in high school and my parents ere in the midst of their big divorce drama so I was spending most of my time at my best friend Kelly's. It was just Kelly and her Mother because her dad left the picture several years earlier. Kelly’s mom was a great surrogate mother because she knew what I was all about and accepted me with no reservations. Kelly was well on her way to becoming a hardcore lesbian so her mom really enjoyed doing girlie things with me. We used shop for clothes together and she taught me the proper way to apply my make-up and style my hair. ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2791  |  
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The Fanncy **Dress** Party

I went to a Priests and Prostitutes party a short while ago in South Africa and loved getting dressed up as a prostitute, it was so much fun and It made me really horny.

I had to get a cab dressed up like this and we all met in a bar before hand. I was the first one to arrive at the bar which was already packed as it was a Friday night and the early (going home from work) crowd had not left. I sat quietly at a table and ordered a double Vodka and Tonic and was watching the door hoping that someone else from the party would come to assist me. I must have been sitting there for 10 minutes an... Continue»
Posted by africangraham 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 1133  |  
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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: 1063  |  
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The Making of a Sissy - Part Eleven

Whilst Bella showered, Ellen and Sandy went down to the poolside to ready some ice and bottles for drinks later; there was Bella’s phone, Ellen tapped in the number to her own phone, and also took down someone else’s number. Ellen smiled wickedly.

“I have a very sweet idea, but I’ll need a week to arrange it; I have to put a proposal to that aunt of hers first. I’ll need your assistance at some point.” Sandy was willing to help out in any way, and the two chatted and giggled as they too went back upstairs to shower and prepare for the evening. Roberts worked swiftly to get the videos and ... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 456  |  
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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: 1062  |  
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relic fort

so as usual i am horny and i figured i would try something new. so i go to a place i have heard about. it is an old bunker fort near me it has lots of dark bunkers and lots of gates oh and lots of poison ivy.

so i pull up it is raining and i had packed my nice latex skirt and top so i decided to check things out. out of the car i go heading to the woods which i was told i would find the over grown play fort. sure enough there it was, i hiked around for a few minutes all the while noticing more and more guys walking around looking at me. finally one guy gets brave enough and ask what a prett... Continue»
Posted by deveon4u 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 888  |  
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The Making of a Sissy - Part Ten

Bella quickly gulped down her vodka and cherry, her bottom tingling with anticipation as her new mature friend gave her a commanding look; she had so enjoyed being submissive for her at the end of a leash, and now she knew she would be bound tightly on a soft inviting bed, and made completely helpless. Her cock stiffened sweetly at the thought; perhaps she would taste the cane again, she would love that. Ellen took Bella’s little hand and squeezed it tightly; though she had only just met this supreme example of a shemale, she knew instinctively she could trust her completely. The redhead smil... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 482  |  
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olderman and mature crossdresser part 2

We left the park and drove to his house which was very nice.I knew he was wealth when he picked up due to his car was new jag. He fixed me drink and we sat on his couch and kissed and made out an heavy petting.He kissed my neck driveing me nuts as he did I rubbed his cock thru his pants which was hard.He asked me if he had gone to far I said to him if you did I would have stopped him.
I asked him how far did he want to go and he said it was up to me.I looked at him an gave him kiss an asked him were his bathroom was he told me so I stood up leaned down and whisper in his ear that I hoped h... Continue»
Posted by cdpaula 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 857  |  
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olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all.
As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me and said that he was sorry for following me around that he was not some kind of crazy killer but ... Continue»
Posted by cdpaula 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 892  |  
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Out of town, I broke free

So I was out of town on business, and I hadn't worn any female cloths out ever in my life, but this time I took some sexy cloths from my roommates girlfriend..and I had been chatting with this transgender girl in the city I was heading to for a few weeks, we would skype and get off together, and she would make me do things to please her..I'm a switch but for this girl I'm her sub slave. When I got to the hotel I took a shower and shaved myself..complete, then I call my Trans friend, for the sake of this story I'll call her Dana, so I called Dana, she told me to get dressed and meet her at this... Continue»
Posted by smonkeys32 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 348  |  
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The Making of a Sissy - Part Nine

As they sat sipping drinks and discussing what shots would be done indoors or out; Bella’s little cock bulged in her sari as the mature redhead licked her lips as she discussed the ways in which Bella should be trussed, collared and leashed, amongst other things. Sandy stood up suddenly and ran across the patio when she saw a tall figure emerge from the house into the sunlight; this was her Carl. Bella looked on enviously as the two squeezed and kissed at length. She could only dream of being that way with Adam, and so yearned for such a moment with him. Sandy tugged Carl over to the others;... Continue»
Posted by midsummerman 2 years ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 466  |  
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