One Of My Shemale Escapades From Back In The Day free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
A number of years later, after my first shemale expereince, I still had a penchant for a hot shemale or a slender sissyboy who was passable. That's when I met Gina, who fit the mold of a slender sissyboy who was much more than passable, she was gorgeous.

The first time we got together was on a rainy Sunday afternoon. My wife was out of town and I was cruising aroind on AOL in the SoCal Shemales chatroom. I came across her screenname and we started to chat. We traded writen descriptions of one another and she sounded very hot. She was white, in her late 30's and was married like me. She told me that her wife knew about her dressing and desire for all things feminine. As long as she broight home the money, paid the bills and did not say anything about all of the cock her wife was getting, Gina could do prety much what she wanted-sounded like a perfect setup! To make it even better, she lived about 10 minutes away from me.

After some more conversation and the exchange of a couple of photos between us, I told her that I wanted her to come over. While she was very shy, she said that she was very turned on by the pics I sent to her, especially the cock shot I sent. I told her that I wanted her to wrap her lips around my thick pole while I ran my hands across her nylon covereg legs. I addition, the thought of her hard little clitty rubbing aainst my legs while she sucked me had me hot and ready for her.

A little more coaxing on my end was all she needed to say that she would come over. She asked me if it would be ok for her to dress at my house as she does not go out in public fully dressed. I have to admit, this tirned me off at first becaue I imagined seeing a guy in every form-talk about an image killer! She assured me that while she would not be fully dressed, I would see the slender sissyboy that would turn me on and was she every right! When I opened the door, she had a delicate, smooth face and long black hair to her shoulders. The jeans she wore were slender and tight, and she had a nice round ass.

I offered her a drink which she gladly accepted. We were both a little nervous and filled with sexual tension. After her drink, she asked where she could change. I took her upstairs to my bedroom and showed her where the master bath was. She went in and said that she would not be long. I told her to take her time-I'll be waiting and I don't want her to rush her transformation. While I waited for her, I slipped out of my clothes and softly stroked my thick black cock while lounging on the bed.

I heard the light switch in the bathroom click off and then the door opened and the transformation was stunning! She was adorned in a sheer deep blue nightgown with a matchnig thong. She also wore sheer black thigh high nylons and a hot pair of black stiletto sandals. Her hair was perfectly placed over her shoulders and her makeup was perfect. Her full red lips slightly parted with anticipation of having them wrapped around my cock. When she looked at me, she gasped and told me that my body was making her tingle. I motioned for her to join me on the bed and when she did, she immediately curled up next to me and I could feel her shudder as she ran her fingers over my body.

While she did this, I started rubbing her plump little ass and kissing her along her neck. I heard her moan with delight and she then started to grind her hard little clit against my legs. That felt even better than I ever imagined it would. Not only could i feel the hardness of her clit against my leg throug the sheet fabric of her thong, I could feel the wetness of her precum against my leg. She continued to leak her juices out of her clit as she contunied to let her hands roam across my body. She then lowered her head and took my nipple into her mouth. Shock waves of pleasure went through me as she did this and my cock felt like it was going to explode. I gave her ass a very hard squeeze and she moaned deeply. With that she used a combination of her full red lips and tongue on my nipple while she started stroking my cock. I was now in a state of pure euphoria and I continued to squeeze, rub and smack her sweet little ass. All of this made her moan even louder and grind her clit against me harder and faster. I then felt her tense up and then she spilled her sweet cream. It flooded her thong and left a gooey smear on my leg. After the last waves of her orgasm subsided, she looked at me as if to apologize. I told her that what she just did was so very hot and with that, she wrapped her lips around my thick pole. She started sucking on it very tenderly, teasing the head and lightly stoking the shaft. The suking started to pick up intensity and then she added her tounge into it, rolling it over the head. This produced a powerful orgasm. She moaned loudly as the first jets of cum shot out of me and into her mouth. She continued to moan as I continued to flood her mouth with my juices. She could not hold it all and it started to run out of her mouth and onto her hands and my stomach. she contunied to suck me dry and licked me clean-both my cum and where she came on my leg. I knew this would be the first of many times I would be with Gina and she never failed to satisfy!

Same as One of my shemale escapades from back in the day Videos

4 years ago
  • 0
  • 14
  • 0

My Shemale Stepmother

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the summer. He had bounced back quickly...

1 year ago
  • 0
  • 14
  • 0

My Shemale Stepmother

Note : This story is completely fictional! My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the...

Incest
1 year ago
  • 0
  • 22
  • 0

PornPics Shemale

Do you get off to looking at porn picture galleries? I have heard this question come up in several discussions, and usually, there are sides. Some people think that pictures are a thing of the past, yet there’s another side that still appreciates good smut in the form of images. Personally, I prefer videos, but what are videos if not moving pictures. Besides, I’m dedicated to providing all perverts with their preferred smut.This article is for dudes that enjoy jerking off to shemale galleries....

Shemale Porn Sites
1 year ago
  • 0
  • 14
  • 0

NudeVista Shemale

Have you ever heard of NudeVista? Of course, you have! The porn discovery engine has been around for over 20-years. Originally a place to visit if you wanted to find porn pictures, the platform has evolved to offer videos, model pages, and so much more!That includes finding shemale pornography that will make you cum your goddamn brains out! Don’t believe me? Well, how about checking out NudaVista.com/Shemale. Here, you will discover all kinds of amazing shemale pornography bound to get you off....

Shemale Porn Sites
1 year ago
  • 0
  • 17
  • 0

SxyPrn Shemale

Shemales are fascinating humans, especially when they have a bigger dick than you have. I can’t say that I don’t enjoy a good tranny film, but I’m not too fond of watching women with a larger pecker than I have, and you guys know that I’m well endowed. Well, I can only imagine how it is for you with your ghost penis. But, hey, I’m not here to compare dick sizes.On the contrary, I’m here to point you in the right direction if you are looking for some hot shemale action. Sxyprn.com is a great...

Shemale Porn Sites
1 year ago
  • 0
  • 22
  • 0

Eporner Shemale

Shemale porn videos have been part of my fapping sessions for a long time now, and I know I’m not the only one. You lot love watching these whores with dicks, and perhaps for different reasons than I do. I do it because, with a t-girl, you always know what you are going to get: any day is anal day. But I bet you do it for the humiliation vibes you get from watching a girl with a big dick than yours. I’m not here to judge, though; I just want to show you where you can find the good content.Well,...

Shemale Porn Sites
4 years ago
  • 0
  • 9
  • 0

Husband Enjoyed Cuckold Sex by Shemale Bull

Hi readers. I’m Aryama. This is my story of how I became an to my wife and our shemale bull. We have been married for a year, but we have no children. The reason is my small 3-inch cock. Even though I used my cock in various ways, I could only use my fingers to make my wife moan. During the first year of our marriage, my wife cum from me only once. Let’s see about my wife. She’s a fair-skinned 5’9 Tamil Goddess. She has D-cup boobs and a huge bubbly booty. If she started walking in the middle...

3 years ago
  • 0
  • 76
  • 0

One womanrsquos depraved shemale adventures

I’m Kami, and I’m a thirty-something blonde who mostly has a preference for other women, which if anything has been heightened by my boyfriend’s recent obsession with T-girls. Secretly though, while I’m busy licking out my gorgeous young flatmate Amy, or my landlady Jess, my mind often wanders towards she-cock, something that through my boyfriend’s sessions I’ve been lucky enough to taste and experience in my pussy a few times now.The other night, I got my first taste of an actual gay and...

4 years ago
  • 0
  • 13
  • 0

Shemale Surprise

anal – shemale – transgender – transsexual – oral – pantyhose – first time – stockings – wedding – lesbian"You can stay with Robert if you wish," Mary said on the phone.I looked up from my laptop where I was pretending to be working when, in reality, I was reading, for the hundredth time, the brilliant novella 'Shemale School: a Teacher Seduced'. The story had created a new obsessive fantasy I had never even considered before: to be with a Shemale.I even contacted the authoress to tell her how...

2 years ago
  • 0
  • 12
  • 0

Shemale Surprise

A married man is seduced and taken by a friend of his wife's. "You can stay with Robert if you wish," Mary said on the phone.I looked up from my laptop where I was pretending to be working when, in reality, I was reading, for the hundredth time, the brilliant novella 'Shemale School: a Teacher Seduced'. The story had created a new obsessive fantasy I had never even considered before: to be with a Shemale.I even contacted the authoress to tell her how much I enjoyed it, and have since became one...

1 year ago
  • 0
  • 21
  • 0

One mans shemale and lesbian adventures

It was my girlfriend Kami’s birthday. She had always been more into girls than guys and so I had arranged a surprise for her - and a treat for both of us. A girl I met earlier that week was to come over to hers that night, and I couldn’t stop the thought of the awesome threesome we were going to have from going round in my head.Kami was, like me, in her early 30s, but looked younger and had no problem attracting all the girls she wanted. And wow, she did get through a lot. Only a couple of...

1 year ago
  • 0
  • 15
  • 0

PornHub Shemale

I think the allure of spending time with hotties that have that something extra swinging between the legs is the ultimate frontier in porn. Long gone are the days when this fantasy fetish was kept a tightly guarded secret. Personally, I find it quite intriguing and I don’t give a fuck about some of the conservative feelings some of you may have. Ladyboys may come across as weird or queer, but I always find the idea of beautiful faces, plump tits, and big cocks in a single package to be really...

Shemale Porn Sites
1 year ago
  • 0
  • 45
  • 0

Long sex story 8211 I Was A Reluctant Shemale

Marilee’s fists tightened in despair as she sat at her secretarial desk and listened to the muffled moans emanating from the office of her boss, JC Wyatt. JC was one of the youngest and most famous casting agents in Hollywood and was the most blatant offender of the “casting couch” which degraded women. The young actress, a stunning blonde who couldn’t have been more than sixteen years old, had looked so hopeful when she had entered that office only twenty...

2 years ago
  • 0
  • 35
  • 0

Notes to Young shemale with mature woman

NOTES for story; “Young shemale with Mature Woman” These are notes to the story entitled “Young shemale with mature woman”. Therefore, you’ll need to read said story to properly understand these enticing notes. Wife and young Ben have been enjoying each other’s company for three days now. Freely walking around naked at our cottage and pond. Ben is finally relaxing about the size of his privates as you’ll recall his penis is only 2.5 inches when erect and his ball sack is tiny. Fortunately, he...

3 years ago
  • 0
  • 30
  • 0

Shemale Make Me Prostiute

Hi Myself Jimmy here I am back after 2 years with new encounters occurred in my life, going to narrate you the same, I am living in Bangalore now, in south Bangalore, I will tell you how I became a male prostitute with the help of a Hijda/Hijra/Shemale/Ladyboy, In my layout there was a beautiful girl with very attractive eyes whose name is Manju may be 24 to 26yrs, lived with her family and would go for house hold work, my age is 28, unmarried and just go a good job and was leaving alone in the...

1 year ago
  • 0
  • 10
  • 0

Shemale Vids

What is it about Shemale Vids that makes them so goddamn enticing? Honestly, it might be a question for the stoned philosophers and horny social scientists of the world. Me? I’m just your friendly neighborhood PornDude. I may not be able to tell you why you’re so attracted to pretty girls with bigger sausages than your own, but I can certainly turn you on to some good pornos starring the well-endowed broads. Some dudes consider themselves ass men, others are fond of the titty, the thigh, or the...

Shemale Porn Sites
4 years ago
  • 0
  • 17
  • 0

St Judes Shemale Academy

My name is Amanda Johnson and I am a 38 year old post operative transsexual and owner and headmistress of a rather unique school, a school that turns troublesome and reluctant boys into shemales. This is the story of St Judes academy for shemales. My own transformation happened over 10 years ago when in my mid twenties I decided to transition from male to female. Being the son of a world famous actress, my gender change was largely kept secret and only a select few of my parents...

1 year ago
  • 0
  • 14
  • 0

Shemale Shopping Spree

She-Male Shopping Spree featuring Chelsea and Victoria, two gorgeous chicks with dicks - and an attitude! by Mistress Tawny Suede "Oh god, I feel so incredibly horny!" said Victoria. "Well, sugar, if we hurry back to the apartment, I've got just the cure," said her best friend and roommate, Chelsea. Victoria looked the stunning black girl in the eye and giggled. "Actually, I haven't been able to get that cute little salesgirl out of my mind," she said as she and Chelsea left the...

2 years ago
  • 0
  • 15
  • 0

Shemale Amazon Goddess

This story is based on a dream I had about shemale porn star Meghan Chevalier around 15 years ago.I'm sitting up in bed. There is an empty glass on the nightstand; I know that I have recently drunk whatever was in the glass. I'm wearing a light violet silk robe, and nothing else. It seems quite feminine. Then I realize that my body has become quite feminine as well. The fat I've been carrying around for years is gone and my waist has tapered down to about 27 inches. My legs are long and slim....

1 year ago
  • 0
  • 22
  • 0

XVideos Shemale

What is it about women that gets you all fucking hard and drippy? Is it their pretty faces, or do your eyes go straight to their titties? Maybe you’re a leg man, or perhaps you love ass, and I’ve known more than a few dudes who love nothing more than a woman’s foot. Then there are dudes like you, whose favorite part of a broad is her penis. Have you checked out the Shemale section over at XVideos?XVideos.com is one of the net’s biggest sources of free smut. The site gets almost 2.5 million...

Shemale Porn Sites
3 years ago
  • 0
  • 25
  • 0

My first threesome with wife and shemale

My sex life with wife was becoming monotonous and we were looking for ways to spice it up. We explored different options which involved fantasies of both of us which we had not been able to fulfill. I had a long time fantasy of having a threesome with wife and a shemale which I shared with wife and after some discussion we agreed to go ahead with it. I had always watched shemale porn with interest. Recently my interest had increased and I was watching more and more of those videos that had...

1 year ago
  • 0
  • 13
  • 0

I Was a Reluctant Shemale

Author notes: I wrote several stories back in about 1995 or so, but due to certain circumstances, I ended up purging them off of my computer. Over the years I have found those stories on the net and resaved them to my hard drive. The story you are about to read is the most recent story that I have found. It was harder to find because it has been posted to a site (Kristen's Archives) by someone else claiming it to be their writing. It is not. It is my story and I am now reclaiming it...

1 year ago
  • 0
  • 8
  • 0

My Indian shemale Mother

100% fiction! The Morning was so gray with clouds free that, when I woke up to the sound of my alarm buzzing at 8:00 AM, I barely realized it was morning. Groaning, I pulled my blankets closer to me, turned over, and tried to go back to sleep. No 19-year-old boy likes waking up for high school at seven in the morning, but it’s even worse on December 21st, two days before Christmas vacation begins. I had no desire to greet such an ugly day, so I decided to sleep until Christmas. Wearing only...

Incest
2 years ago
  • 0
  • 27
  • 0

Stolen Stockings Pt 1 SHEMALE LESBIAN PORN

WELCOME TO CHURCH OF RUBBER - STOLEN STOCKING CONFESSION .the sign read above My study doorway.My transex very leggy young secretary nurse led the new prospect in to My parlor and knocked on my door and I said "COME"the heavy gothic arch door swung open and there stood the two stunning transexual stocking sluts in ultimate sissy wear. One happened to be My private nurse and secretary, the other was a specially chosen pretty thing who had been in communication with ME for some time now. My...

2 years ago
  • 0
  • 10
  • 0

SHEMALE FAVORS

"LATE NIGHTS EARLY MORNINGS" FRIDAY NOVEMBER 27TH 2020 - SHEMALE ASKS ME FOR A FAVOR YEARS AGO .. I WROTE MY FIRST XHAMSTER LIFE EXPERIENCE STORY ON HERE. IF YOU HAVENT READ OR SEEN IT, I WOULD MAYBE SUGGEST YOU CHECK IT OUT FIRST BEFORE YOU READ THIS. HERE IS THE LINK FOR SOME BACK STORY OF MY OLD ROOMMATE AND THAI TS LADYBOY LOVER “ NINA “ https://xhamster.com/stories/what-a-week-anal-debauchery-at-its-finest-449485 But fast forward to a few days ago now, the following scripture is based on...

3 years ago
  • 0
  • 20
  • 0

Autobiography of a Shemale

Autobiography of a Shemale Dominatrix By Barbi Satin Introduction Among many in the transgender world the term shemale is offensive. Transsexual in considered a proper, politically correct term. Transsexuals are persons born into the wrong gender and have the psychology and even brain structures of the opposite gender. They go...

1 year ago
  • 0
  • 14
  • 0

xHamster Shemale

While I am pretty sure that you already heard about xHamster before, I am not here to talk about that site as much as I am here to tell you more about a certain section that I really like on xHamster. This site is filled with many hot videos featuring the hottest trannies, and you are more than welcome to check them all out.So, do you think that chicks with dicks are hot? If you do, then you have come to the right section, because that is exactly what xHamster has to offer. Now, do not get me...

Shemale Porn Sites
1 year ago
  • 0
  • 13
  • 0

My Indian Shemale Mother Part1

100% fiction! I woke up the next morning feeling warm and contented. I opened my eyes to find myself lying in my mother's bed, completely naked, covered by soft, do wny blankets. I looked at the clock. It was nearly ten AM! I was going to be late for Office! All at once, the memories of the previous night struck me. I remembered my mom and I watching a shemale porno together, masturbating together, bathing together, and finally sleeping together. If this could be called normal, that was...

Incest
1 year ago
  • 0
  • 10
  • 0

The Diary of a Shemale Whore on Tour

This one comes by popular request and is dedicated to all you naughty people who fe-mailed me and complained that whilst you enjoyed my stories you felt that I could perhaps be a little more filthy instead of being suggestive! Well, I've always said that I'll give you what you want, well, you got it and I hope you like it! Disclaimer; (seriously!) The following story does not reflect the writers personal tastes and depicts entirely fictitious characters and fantasy scenes of an...

2 years ago
  • 0
  • 22
  • 0

A tale of male seduced by shemalefrom rohitraj

Hi I am Rohit,I am young,very fair and handsome,well educated decent person age 26 years almost 6 feet tall living in Hyderabad,India.I am a great fan of Indiansexstories.net site and always read the sexual stories.....and compliment the people who write so long stories......i always wanted to share my encounters......but alas i dint met a single encounter.....but recently.....met an exciting one....which i am going to reveal to you people......This is my first story and i request you people...

1 year ago
  • 0
  • 28
  • 0

How I became a Slave to a Shemale

Hey readers, This is Karan, back with another . I am sure that you guys will love it. I lost my asshole virginity to a shemale I met at a massage parlour. She took me to her place and fucked the wits out of me. So let me give you my brief intro again. I am 5 foot 10 inches tall, have a fluffy personality, and have a dark complexion, but attractive. I have a tool of 6 inches, and I am a pansexual from Hyderabad. I am shemale lover and would have sex with shemales only. I am flexible with both...

3 years ago
  • 0
  • 9
  • 0

A Shemale Fantasy and my Wife Part 1

Our relationship has always been good. We love each other, and the life we have built. But lately our sex life and our life in general has become some what stagnant. We get up go to work, come home have dinner, then go to bed. It's the same thing you've heard from couples who have been married for ten years. The excitement level no longer exceeds sexual intercourse more then once a week. It becomes frustrating at times because I've always been the type who wants to try new...

2 years ago
  • 0
  • 9
  • 0

A Shemale Fantasy and my Wife Part 1

Introduction: I didnt know what I was in for. But what a ride. I was always a sexually open individual. But in my world sexual expression wasnt really part of my routine. Im a 35 year old married man. My wife and I met back in high school and have been together ever since. Our relationship has always been good. We love each other, and the life we have built. But lately our sex life and our life in general has become some what stagnant. We get up go to work, come home have dinner, then go to...

2 years ago
  • 0
  • 17
  • 0

MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few...

4 years ago
  • 0
  • 20
  • 0

Mile high shemale

“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual.For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator).The community I live in has lots of shemale beauts; maybe that started my interest. One such ravishing creature has a gallery close to my office, and I fantasize every time I see her in the coffee shop. She also has an eye popping diamond on her ring finger.Once in a while I’d visit...

2 years ago
  • 0
  • 17
  • 0

MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few...

4 years ago
  • 0
  • 17
  • 0

Young shemale with mature woman

High speed internet has arrived at our cottage, fibre-optics! We own almost 500 acres with a very large pond, nice home with a pool in its backyard. Pond has a lovely beach but is a serious walk from our house/cottage, roughly 20 minutes via a trail through the woods. Seclusion is paramount, peace and quiet, love it!! We've decided to try living at our cottage and have a grown daughter with her husband and k**s live at our house. I went on an extended trip to Europe for business. Wife loved...

3 years ago
  • 0
  • 12
  • 0

Shemale Ne Mummy Ko Choda

Hi friends yeh story meri, meri mummy aur shemale ke beech hai. Is story mein btaunga kaise shemale ko maine choda aur phir kaise shemale ne meri mummy ki chudai ki. Meri mummy jinka figure 34-30-36, bank mein job karti hai. Unka divorce hue 6 saal ho gaye hai. Mummy job ke karan kafi fit hai. Yeh incident 3 mahine pahle ka hai. Main aise hi net surffing kar raha tha.Tabhi ek din maine shemale wali video dekhi.Woh mujhe kafi achi lagi. Us mein shemale gand marwata hai aur marta bhi hai. Mujhe...

3 years ago
  • 0
  • 28
  • 0

Mommys Christmas Shemale for David

She had to make it good. It couldn't be just another gift wrapped cologne set, or a gift card to Ulta. She wanted this Christmas to celebrate her newfound lust with her k**s. She wanted David and Dana's presents to be fun, kinky and perverted. That's why, after a few weeks of thinking about it and a little searching, she had finally found David's gift.David had very open tastes. He was very in touch with his sexuality; he knew what he liked, and he was willing to explore new things to keep...

1 year ago
  • 0
  • 12
  • 0

London Mein Indian Shemale Se Fuck Hua

Hi dosto, mera naam Azim hai. Meri age 23 hai aur main ek bisexual mard hun. Mujhe sex ka bohut craze hai chahe aurat ke sath ya aadmi ke sath. . Aur yeh meri pehli story ek shemale ke sath hai jo kuch saalon pehle ki hai. Agar aap logon ko meri gay stories aur maid ke sath stories pasand hai toh zaroor yeh story bhi aap logon ko bohut pasand aaye gi. Yeh kahani 2 saal pehle ki hai jab main London mein padhai kar raha tha. Meri age uss waqt 21 thi aur yeh meri birthday ke kuch dinon baad ki...

1 year ago
  • 0
  • 20
  • 0

Sherry got fucked by the Shemale hairdresser Shemale Sex Stories

Living in the poshest parts of New York, Sherry was perfectly happy with every aspect of her life. She was ambitious and had a great job. She earned enough to lead a luxurious life in this part of the city. The only trouble was her hectic lifestyle and how it left her with no time to date. Her last breakup was rather messy. It has been three months since she broke up with her boyfriend. The only thing she misses now is the sex. She was not much into flings and one-night-stands so finding a...

Shemale
2 years ago
  • 0
  • 16
  • 0

Would love a shemale like this

****d (sort of) by a Shemale!I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable...

3 years ago
  • 0
  • 25
  • 0

My Sister8217s A Shemale

We are a family of four. Me, my parents and my sister. I am 23 years and my sister is 18 years old. She is very beautiful, fair and very sweet looking with small perky boobs and a very petite slender body. I, on the other, am a regular gym goer and have a very good physique, but the thing with me was that I was gay and loved gay and shemale sex. I have done gay sex a couple of times but have never been with a shemale. I always knew there was something different about my sister as I often...

Gay Male
1 year ago
  • 0
  • 14
  • 0

Making a porn flick and then sex with a shemale

I had met Josie at a bar and she had no qualms in letting me know that she was a shemale. We both were drunk and horny, so she let me feel her up. I had had gay encounters and considered myself bisexual, so I wasn’t afraid of touching another penis. It made me hard. I was too drunk for sex so I shared my contact information with her and when we met, there was a porn flick made on my camera while having sex with a shemale. Josie had arrived at my apartment on Saturday and we were having a few...

Shemale
3 years ago
  • 0
  • 6
  • 0

A Shemale Fantasy and my Wife Part 2

About an hour later my phone vibrated once again. It was from Carol. This time she had send me a picture of a shemale. The text read "do you think she's hot?" I responded with a YES! And I meant it. This shemale had beautiful big tits and a pretty big dick. In fact it may have been a bit bigger then mine. This was really starting to get interesting, just like Carol had promised. She was texting me dirty pictures and being really naughty. I loved it. I wanted to be naughty just...

4 years ago
  • 0
  • 7
  • 0

A Shemale Fantasy and my Wife Part 2

Introduction: I didnt know what I was in for. But what a ride I arrived at work, walked into my office and settled in for the day. Just as I was checking emails on my computer my phone vibrated. I took a look. It was a text from Carol. In closed was a picture of her laying in bed totally nude with her legs spread. The text read, my tight wet pussy is waiting for you. I instantly got horny. I would never dreamed Carol would send me a picture like that. I texted back I cant wait to stick my dick...

3 years ago
  • 0
  • 10
  • 0

A Shemale Fantasy and my wife Part 4

A few hours later I was woken up by Carol. "Wake up baby this day is just getting started" she said. My eyes opened and I was like a kid on Christmas morning. I couldn't wait to see and "feel" what she had in store for me next. Carol instructed me to shower get dressed and leave the house for a few hours. My next surprise needed some set up. I did ask she told me. Before I left Carol came up to me grabbed my dick, kissed me and said "get ready for some fun". Having no...

3 years ago
  • 0
  • 9
  • 0

A Shemale Fantasy and my wife Part 4

Introduction: The Conclusion Basking in the glow of what just happened, I put my head back and just passed out from total bliss. I didnt know what else Carol had in store, but I knew I wanted to be well rested. A few hours later I was woken up by Carol. Wake up baby this day is just getting started she said. My eyes opened and I was like a kid on Christmas morning. I couldnt wait to see and feel what she had in store for me next. Carol instructed me to shower get dressed and leave the house...

2 years ago
  • 0
  • 14
  • 0

Shemale Stewardess Seduction

Please note that this story is not written by me! It was stored in my computer for a long time now and decided to share it with you. The author's name as well as the site I found the story are not known... My introduction into the sultry, steamy world of shemales came (and I mean came!) at 35,000 feet, on a plane flight to the Northwest. I had been working myself to the bone, staying until ten or eleven at night, coming back in at six o'clock in the morning, and I guess the stress...

2 years ago
  • 0
  • 8
  • 0

Beautiful Shemale Sex Fantasy 8211 Part 1

Hello people, Leviathan here with my first story. To describe me, I am an average looking guy with a pint of femme body and many have said I have a great ass. Jumping into the story, this is purely a work of fiction. I request you all forgive me for grammatical and spelling errors. I made up a story by mixing a few of my fantasies and pint of my imagination, and a lot of horniness! It was around 8 pm. I set off for a 16-hour long journey to native, my train just arrived. After a fuss, I managed...

Gay Male
1 year ago
  • 0
  • 13
  • 0

Sweet Julie Birth of a Shemale

Sweet Julie Birth of a Shemale by Mistress Tawny Suede Chapter One Is It Just a Role? The dress rehearsal for the drama club's latest production was over. The curtain fell, the audience of excited parents applauded enthusiastically. The curtain rose and the performers stepped forward to take their bows. The curtain fell again and still the crowd applauded. The two stars, Troy and Julie, took their positions centre stage, holding hands as the curtain rose one more time. They...

1 year ago
  • 0
  • 7
  • 0

My Vivid Memory of Sex with a Shemale Free Sex Stories and Adult Erotica Stories

I am a lonely man in his forties. I love to travel, dine and explore new places by myself. But I often wish for a partner. I got divorced early, so the little chance of being with someone was also ruined in my memory. So, each morning I would go to work, do my mundane bank job and visit my nearest LGBT bar. I am sharing my memory of sex with a Shemale and how I found pleasure in it. I am not gay or have any element of pride in me but what really fascinates me is Shemales. I believe they have...

Shemale
1 year ago
  • 0
  • 6
  • 0

Fucking the Shemale Librarian on the table Shemale Sex Stories

I was a student by day and a firefighter by night. I had joined the team two years ago and was trying to get a college degree by attending classes at night. I often used to silently masturbate when I would go to the library, as I was alone in the evenings, at the almost closing time and it would take the edge off a bit. During one of these times, I saw the local librarian and oh she was hot. Perky tits, tight ass and a low cut blouse. Wow. She would probably feature in my fantasies for a while....

Shemale
2 years ago
  • 0
  • 14
  • 0

First time fucked by a shemale

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.Her hair was dirty blond...

2 years ago
  • 0
  • 12
  • 0

shemale fantasy ive read before and dream

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.Her hair was dirty blond...

2 years ago
  • 0
  • 11
  • 0

A Shemale Vacation

A Shemale Vacation - Part One by Richard-to-Rachel I was eighteen, na?ve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for me, wild sex was something I wasn't exactly familiar with. I was still a virgin and I was pretty determined that that...

3 years ago
  • 0
  • 5
  • 0

A Shemale Fantasy and my wife Part 3

Their was so many areas I wanted to explore with her. I felt like a teenager again. I couldn't stop thinking about how naughty Carol was being. It was Sunday, and my only day off so I decided I would do something nice and bring Carol breakfast in bed. I went to our kitchen and made our favorite breakfast, bacon and eggs. As I began to walk up the stairs I could hear moans coming from our bedroom. They weren't Carols. I walked into the room to see Carol totally nude, with her...

3 years ago
  • 0
  • 4
  • 0

A Shemale Fantasy and my wife Part 3

Introduction: I didnt know what I was in for. But what a ride After our night of raw sexuality, I started to look at Carol in a all new way. She wasnt just my wife, now she was so much more. Their was so many areas I wanted to explore with her. I felt like a teenager again. I couldnt stop thinking about how naughty Carol was being. It was Sunday, and my only day off so I decided I would do something nice and bring Carol breakfast in bed. I went to our kitchen and made our favorite...

Porn Trends