Shemales Porn Stories
Page 73

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 1 year 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 1 year 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 1 year ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 1132  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 1061  |  
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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 1 year 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 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1057  |  
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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 1 year 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 1 year 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 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 855  |  
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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 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 893  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 350  |  
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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 1 year ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 469  |  
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The Making of a Sissy - Part Eight

The girls sat cross legged sipping orange juice as the day warmed up around them. Roberts’ house had extensive lush lawns beyond the pool which shimmered in the hot sun; the pool looked very inviting to Bella and Roberts looked at the pretty sissy, his mouth watering as his cock pulsed.

“Just go in whenever you want; it’s nice to see you free from your usual routine, I know how strict your Aunt Jane is with you; swim naked if you wish, no need for a bikini here. Sandy and the others never bother with swimsuits when they’re here.” Bella was a little shy at first, but Roberts had seen her v... Continue»
Posted by midsummerman 1 year ago  |  Categories: Fetish, Mature, Shemales  |  Views: 402  |  
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blew him away

recently i met a frustrated 32 year old married man who was not getting sex from his older wife,he told me he was straight. I met him in holiday inn in town,i arrived in reception and met him.My hair was very long,i had lots of make up on,was wearing 8 inch black heels,black stockings,suspenders,g string,black bra,body jewellry,belly button stud,on top i was wearing a red tight dress,my nails were painted,had thick red lipstick.

He gave me a kiss and said i looked beautiful and i followed him too his room, i look embarassed as everyone looked at me,i felt like a prostitute becasue of the wa... Continue»
Posted by ladyboyslut 1 year ago  |  Categories: Anal, Shemales  |  Views: 1957  |  
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Date Coach from sissifyourself


Chapter 1


“So what brings you here today?”
Daniel looked at the date coach. He wasn’t sure of his height, taller than himself for sure, who stood at a paltry 5’ 4”, even though he was already 23 years old. He’d been made fun of his whole life for his height, but he still had a good bit of muscle, and some fat on him, as he weighed about 150 pounds, with nary a hair on his body. The doctor on the other hand, still looked athletic and muscular through his button down shirt, and didn’t look a day over 35. With his short clean cut hair and clean shaven face he could tell this guy was real ... Continue»
Posted by slim_krak 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1187  |  
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BLIND DATE NIGHT part 2

He grasped my hand and we walked briskly from his car to the door of his condo with my 5 inch black heels clicking madly against the concrete. We moved in such haste that I was afraid I'd come tumbling down from the height of my heels. Once inside the condo he roughly grabbed me and pulled me tightly against his taut gorgeous hunk body. He leaned down and locked his lips to mine. He used his tongue to easily part my lips and f***ed his tongue down my throat. Our tongues quickly met and began a dance of passion. I was in heaven and ready to give myself to him totally, wantonly, eagerly and sure... Continue»
Posted by chrissieCD 1 year ago  |  Categories: Anal, Shemales  |  Views: 695  |  
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The Blind Date Night Part 1

The date was arranged by a good friend of mine, she said she'd shown my picture to Warren and he kept pestering her to arrange a meeting. I finally agreed to meet him with no strings attached or promises. I had no idea what to expect or how far things might go but I always like to be prepared. I showered, shaved my legs and any other area that needed attention, shampooed my hair and perfumed and powdered my body. I decided to wear black thigh hi stockings, a black push-up bra and the cutest tiniest string bikini panty. The panty was black with a touch of lime green lacy trim. The lime green st... Continue»
Posted by chrissieCD 1 year ago  |  Categories: Anal, Shemales  |  Views: 702  |  
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The Making of a Sissy - Part Seven

As Sandy pulled into the drive of Aunt Jane’ s house, Tara turned from the front passenger seat and eyed the forlorn looking sissy seated centrally between her two s****rs with some satisfaction.

“It’s a good thing your friend can stay with you tonight to console you; of course I’d have done the same if she were not staying.” She and the s****rs who sandwiched Bella, all sniggered sarcastically at the sheer comedy of the thought. Bella maintained a look of hopeless nonchalance as she gazed aimlessly through the window as Sandy applied the handbrake. The s****rs alighted from the vehicle ... Continue»
Posted by midsummerman 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 511  |  
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unexpected

Well my mom knowing I was a crossdresser and hell all about me and more.I have only talked to her on the phone since her s****r Mary came for visit two weeks ago.Well aunt Mary didn't know that i was dressing as woman and living as one plus she didn't know at all about me and my mom being together.
I just got home from getting my nails filled and some shopping for sexy shoes and dress I wanted when the phone rang.I looked at the caller id and seen it was my mom.I answered it and said hello. To my surprise it was my aunt.
She said how are you? Good and you? She said well I been here to wee... Continue»
Posted by cdpaula 1 year ago  |  Categories: Mature, Shemales, Taboo  |  Views: 1726  |  
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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 1 year ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1421  |  
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