Shemales Porn Stories
Page 66

My first time with a shemale

This is a true story, probably the wildest thing that ever happened to me. It happened when I was about 19 years old and lived in Hamburg, Germany. At the time I was one of those willowy, thin guys, little body hair and a healthy appetite for sex but not much experience yet. At a young age I discovered how exciting it is when I fondled and fingered my ass while masturbating and I developed a real fascination with anal sex.

At the time I used to visit a club ("disco" in those days) somewhere off the Reeperbahn, the famous red light district in Hamburg. One such Saturday I left the club in ... Continue»
Posted by HOLY-SMOKE 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 5489  |  
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Summer Woods CD

School was just out. My mother and father worked and my s****r was older than me and slept most of the summer it seemed. She would get up late and i spent many summer days dressing in her panties and bras, experimenting with her makeup and acting the slut. I was settling into the summertime vacation routine.

This summer though i started riding my bike to the state park that was a few miles away. I stashed a box in a secret place deep in the woods by the river bank. Well away from all the trails that people sometimes wandered. Initially when i discovered these woods, i would simply wander na... Continue»
Posted by cherylfabrizio 2 years ago  |  Categories: Shemales, Taboo  |  Views: 2286  |  
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Angel and I share Laura

Laura and Angel had been friends since Laura moved to the area a few months earlier. They had met through work and became fast friends. Both Angel and I had been attracted to her since we had met her. She was 25, short only about 5 feet tall, skinny, but with lovely big tits. She had big brown eyes and mouse brown hair and a beautiful smile. Not only that but a lovely girl smart and funny. Angel had asked her to join us in a threesome but she didn’t want to as she was only interested in Angel not me. She asked if she would be interested in just letting me watch, but she still wouldn’t go for i... Continue»
Posted by onebaddaddy 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 2076  |  
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Noelle's first time


I was 22 the first time I ventured out as Noelle. I had put the wig and some items of clothing on before in the bedroom or bathroom, but nobody had ever seen me before. I had been chatting online with a beautiful blonde 23 year old named Jenny. She lived about an hour away and invited me over to help with a full make over.

At the time, my wardrobe was skimpy and makeup non-existent, but I packed everything I had into a large tupperware bin and made the trip. I was so nervous I sat in my new VW in the parking lot of her apartment building for twenty minutes trying to decide whether or ... Continue»
Posted by noellejordan 4 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1627  |  
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Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift sto... Continue»
Posted by MichelleSEmass 3 years ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 2443  |  
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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: 634  |  
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My wife dressed me and used me like a slut

I think you are about ready my wife “Jen” exclaimed and she rotated me towards the mirror. My cock was already rock hard and sticky soaking the silky panties as I looked at my reflection. I gazed at my blonde shoulder length wig bounded into two braided pig tails, my face heavily coated in foundation, my eyebrows and lashes painted dark, around my eyes multi shades of blue and my lips a glossy pink. I could feel the silky tiny cup bra as it rub across my nipples, I could feel the top of the multi colored leggings clasping my thighs with the feeling of the tiny skirt that just covered my pantie... Continue»
Posted by Zeffer1 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1902  |  
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My First Tranny

I met Charkara (her real name) through an adult dating site. You can find her pictures on my xhamster page titled,

"My First Tranny". We corresponded through the dating site quite regularly before we decided to take it to next

level and exchange phone numbers and email addresses. We talked on the phone getting to know each other, what we

liked to do sexually, etc. She came off as a total freak willing to do most anything which was an extreme turn-on

for me. We then begun having phone sex with her telling me how she wanted to suck my dick and drink my cum and how

she wa... Continue»
Posted by ghostdawgg62 3 years ago  |  Categories: First Time, Shemales  |  Views: 1103  |  
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THE DARK BACKWARDS CONTINUES !

I jerked off several times while watching the SULKA video. At this point I wanted more. I returned the videocassette to the video store and made my way towards the darkness that was the ADULT section. I opened the door and there were several people in the room. My excitement turned to fear. Fear of being in a room of strangers looking for porn. My hands shook a little as I tried to hide my shame. I nervously looked around the room to find a spot where I could sheild my face.

I wanted the room to myself. I waited and pretended to be interested in the straight porn. I must have been in th... Continue»
Posted by bryanferryfan 2 years ago  |  Categories: Shemales  |  Views: 886  |  
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My sissy son,by his dad and lover. Part 2

Hi,thought it was about time i let you know about my son and me.

This is Part 2.

So...there i was,on my knees staring at my son's beautifull cock. Not big,only 4" long..but sweet with a nice head and completely shaved..(or waxed). "Oh Jack...suck me please...pleeease...been ages since a handsome older gentleman touched me there." Pre-cum was leaking from it...and i licked the end...and gently took him into my mouth! He moaned and slowly made his hips go forward and back...gentle movements like he was fucking my mouth.I was sooo horny at this point i would have done anything...so i did...... Continue»
Posted by chocandres 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1680  |  
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Job Interview

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Keliana Kotey, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company’s receptionist, Paula, put her head around the office door to tell me that Miss Kotey was waiting and asked if she should show her in. I agreed and sat back to watch the view of Paula’s nice arse as she walked away from me. A twenty two year old gorgeous blonde, Paula was the kind of person who brighten... Continue»
Posted by keliana 4 years ago  |  Categories: Shemales  |  Views: 4380  |  
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Why I miss my ex

Why I Miss My Ex
I feel obligated to say that I am not a passable crossdresser, not even close. Even without my beard, I’m very masculine, large framed, and I have a very deep voice. All of these things aside, I love to dress up in sexy lingerie, panties, dresses, bras etc. While I’m dressed, I love to be verbally humiliated, although, I don’t think being called names like “sissy” or “fag” or “cuckold” is actually humiliating. For me, it’s a huge turn on, and I love to think about sucking cock while I’m being humiliated.
It’s quite a long story about how I got my ex-wife to play with ... Continue»
Posted by pbg732 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 897  |  
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A Trannie takes her first big black cock

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big heavy set African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him little smile. When I could see him coming down the hall the next time I got up and slowly walked around the corner into the next hallway so he could... Continue»
Posted by toniparr 4 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 3200  |  
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A busy Friday night. [CD/Gloryhole/neighbor]



I had been looking forward to this weekend for a month. My wife was going to visit some friends in NYC, and I was staying home, by myself. Yup, just me and all of my favorite things, like stockings and panties, and sexy little outfits. The torture was finally over, and the Friday she was to leave, arrived. I was still at work when she called me to tell me she was on her way up rt. 95. I wished her safe travels, and told her I would talk to her tomorrow.

I immediately left work, and headed for my car. I was so excited that I practically ran out of the office. I was going to indulg... Continue»
Posted by pbg732 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3653  |  
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Used Like A BBC Whore

About a year ago while living in a hotel and living there as a Transexual I was used by a young black man as his whore for the night.

He moved in about two weeks ago with a couple friends. They where maybe 5 rooms away from me on 1st floor. As the week wore on I would be coimg and going and would notice them watching me. When I would walk by they never said anything but one of the guys always smiled at me.

While one night I got a phone call and he said his name was Rick and he lived down the hall from me. He told me what he looked like and then I realized it was the young black guy that... Continue»
Posted by sissy_gurl 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 2937  |  
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How I Became Vanessa Chapter 3

Hello dear readers,

I strongly encourage you to read the previous two chapters of this story to fully grasp the sudden changes which affected my life.

*

At home, Elena was waiting for me but she wasn't alone, her boyfriend was there too. He was a tall black guy named Jeff. I told them all the things that happened at July's, blushing as Jeff was watching me with desire.

Elena hadn't changed her sexy outfit and her beautiful face leaned towards Jeff's crotch uncovering his 10 inch cock which was even thicker than John's. She started to suck it hungrily, encouraging me to join her whi... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Shemales  |  Views: 909  |  
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His teacher, The transsexual

A really nice story from another web page! Enjoy

Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't accept excuses.

Greg had only started his last year of high school here after his eighteenth birthday a few months ago. He was worried about the impressions he was making. He got to the door of his health class and checked his watch apprehensive... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  Views: 1564  |  
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Delilah and the Deep Blue Sea. (Part Two)



When I awoke the next morning I was alone. I rose up from my bed amidst the ruins of the villa and peered around cautiously. There was no sign of her. Carefully I tip-toed out from the ruins and conducted a quick scan of the surroundings. The little olive grove was quite deserted other than the small creatures with which I shared the island. These seemed busy at this early hour. There was a little dark grey bird singing from the scrub at the edge of the olive grove. It had a musical voice I found quite soothing. I was to become familiar with that little bird and the mate he found to build ... Continue»
Posted by Mikebasil 3 years ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 995  |  
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The Making of A Sissy-Part One

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father. Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind. Jane’s girls took special delight in dressing their sissy b*****r and loved to take him out to the mall and such places, dressed in pink frilly skirts, where he learned to be humiliated. He was shown to the packs of small... Continue»
Posted by midsummerman 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1750  |  
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A Halloween Hoodie story

*crossdress story*
This is the story of my first time going out dressed; it was halloween last year (2009). I figured i'd have less to worry about walking around dressed in a gothic tartan corset, spider-web mini-skirt, fencenet tights and about 10 armbands and bangles. It wasn't exactly brilliant but it was the excitement that spurred me on.

Of course i was scared of seeing someone i knew, like a neighbour or a friend, but it was about 22:00ish, so i figured it was dark enough and late enough to avoid those kinds of people.

It was a lovely feeling as i stepped outside, the wind rushing... Continue»
Posted by KitsuneTV 4 years ago  |  Categories: Shemales  |  Views: 585  |  
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