Shemales Porn Stories
Page 85

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  |  
95%
  |  12

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: 484  |  
100%
  |  4

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  |  
98%
  |  6

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: 894  |  
95%
  |  2

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: 349  |  
100%
  |  3

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: 467  |  
100%
  |  3

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 2 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 400  |  
97%
  |  3

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 2 years ago  |  Categories: Anal, Shemales  |  Views: 1957  |  
91%
  |  1

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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1232  |  
100%
  |  10

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 2 years ago  |  Categories: Anal, Shemales  |  Views: 695  |  
92%
  |  3

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 2 years ago  |  Categories: Anal, Shemales  |  Views: 702  |  
92%
  |  3

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 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 511  |  
95%
  |  3

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 2 years ago  |  Categories: Mature, Shemales, Taboo  |  Views: 1726  |  
86%
  |  3

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 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1424  |  
91%
  |  10

The Making of a Sissy - Part Six

Roberts took full advantage of his few minutes alone with Bella, as Aunt Jane attended to the caller at the door; he wiped her soft lips clean of his sticky semen and sat her tenderly on his lap, careful to let her sore little cheeks hang over; he caressed the soft white flesh and softly kissed her forehead.

“I’m sorry I had to punish you; I’d love to make it up to you, how would you like to come and stay at my place for a few days? I promise I won’t do any more than take a few pictures of you; there are other girls like you there, and we have a nice swimming pool and plenty of booze, I’ve... Continue»
Posted by midsummerman 2 years ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 614  |  
96%
  |  2

The fun part of stephons run in with sora

Ok, its going to be ok stephon. I think to myself as I reveal her cock. It turns out shemale cock isn't that different from regular cock. Or at least mine, I have never sucked off a guy so......

Anyway

Mouth, neck, upper chest, natural breast, chest, belly button, below belly button, shorts, panties. I stop, im still second guessing myself and then just nut up, expose her cock and lick it.

Umm.... This feeling is different than I expected. I think that I'm actually enjoying it. Like three minutes go by and im sucking on the head. sora is moaning so I guess I'm doing good. I was fuc... Continue»
Posted by cooler34 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 419  |  
97%
  |  1

Wanted

Not really a story, more about what I want.

I am a Bi curious guy. I love pussy, but I really like cock. What I am looking for is a smooth feminine guy or tranny that would let me use him/her for an experiment... an experiment to see how far I'll go.

First, I would like to meet in a neutral place, somewhere private of course. I need to be discreet about it all.

I would like him to drop his pants and let me play with his cock. I'd kiss it, suck on it, rub it against my cock. Once he is totally hard I want him/her to lay back and let me worship at their alter. I'll lick it from ba... Continue»
Posted by siezetheday 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 716  |  
89%
  |  2

turned into a slut by my dad

I opened my eyes, blinked, yawned, closed them again.

I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asl**p. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless.

I tired to move my body and I found it difficult. I could move though, I rolled over onto my stomach and opened my eyes, I was on the guest bed in the basement. Blinking didn't clear the fuzz from the world, so I went ahead and tried to get out of bed. As I stood I felt an i... Continue»
Posted by crossD93 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3549  |  
93%
  |  6

Stephons first run in with Sora

I'm a young, attractive, slender, african american young man. I'm on my grind everyday. I like to drink, sl**p, and fuck. I find that I can make any woman laugh until it is about that time to fuck. This is just one incident that proves this stament.

Alright so I'm in one of my classes doing my regular, being a class clown, and funny as hell. all of a sudden the most amazing looking female walks through the doors of our lecture hall and im like... Fuck, its time to calm down because if i want to sl**p with this female anytime this century I'm going to have to show that I'm a catch, and not ... Continue»
Posted by cooler34 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 774  |  
98%
  |  4

The Making of A Sissy-Part Five

Bella washed away her tears and the various aromas of the night in her en-suite shower cubicle, shampooing her soft brown hair free of the semen deposited by the males and the womanly essence of Tara. After drying her soft downy body she retreated to her silky bed, shuddered and cried a little more as she remembered what she had been subjected too. Tara was mean, but was also right; what would Adam think of her? She toyed with the phone and the instructions given by Sandy, luckily, the other girls were always losing their phone charge leads so Jane had bought several ‘universal’ adaptors wi... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 619  |  
99%
  |  4