How I Ended Up A Submissive Shemale Slut...Part 1 free porn video

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I am sitting here in my studio apartment, and I am alone and depressed and looking for guidance from a very dominant woman who wants a very submissive shemale slut that is 30 years old, horny as hell, and shares the same likes and tastes that I do. Mainly forced blowjobs, and lots of different outfits, everything from leather, latex, lingerie, you name it. Let me go back 5 years ago to how it all started for me. We all have our own stories and beginnings, and this one is mine.



I am a very intelligent, personable person, eager to please but not overly so, and I get along with everyone that I meet. I stand at 5' 8" tall and I weigh 155 lbs, almost shoulder length brown hair but not feminine at first, big bright blue eyes, long eyelashes and absolutely no body hair except around my cock.



Growing up I never had any problem making friends and being sociable with both men and women. I have always been attracted to women, but around age 10, one of my friends’ older sister had sex with her boyfriend in their basement and had left a pair of her silk bikini panties behind a sofa cushion. I had gone over my friend’s house for a sleepover and found them during the middle of the night. They were black silk, string bikini panties with bright pink hearts all over them and a delicate lace trim. They were from Victoria ’s Secret. I had a very big crush on Denise (my friend’s sister) and when I found those panties, I just knew that I had stumbled onto something that would be a landmark for the rest of my life. I of course kept them hidden until I got home, and would take them out and just stare at them and imagine her wearing them. After a few days of this, I tried masturbating for the first time and was hooked. For the next few years I would find any chance that I could get to sneak into her room and go through her top drawer and sometimes take a pair of panties or a bra. I managed to get a bikini of hers as well. But that's as far as it went.



As I got older, I had a very embarrassing problem that just got worse as time went by. I got bigger and began to mature but my penis stayed small. I mean really small, when I am hard as a rock I am about 4 inches long. Unbeknownst to everybody, I was extremely self conscious about anything relating to real relationships or sex with a woman. I kept it very well hidden because I’m so outgoing and had tons of friends. I always lied when my male friends and I would talk about experiences with sex; but, never enough that is seemed suspicious like I was covering something up or hiding something. And I do love women, so I would make just as many comments with my friends about hot girls in school, and what I wanted to do to them, etc. But I was terrified of actually doing anything with any of them because of what they would say about the size of my little cock. This behavior continued into my twenties with me still being a virgin, and developing quite a fetish for lingerie and sexy female attire.



Over time I began having fantasies of shemales, probably because in my mind they weren't nearly as much as a threat as a real girl when it came to being devastatingly humiliating if my secret was discovered. No matter who was the first to see my tiny cock, I knew that there would definitely be a lot of humiliation, and so even in my fantasies I was becoming submissive. I began to think about the fact that I would only be able to satisfy anyone orally, and so my shemale fantasies slowly but surely involved to include some oral on my part, but it was strongly tied to lingerie and being forced into it. All of my sexual release was from internet stories occasionally, and phone sex lines.



I moved to Florida in my early twenties. I had moved down there with a couple of friends from home. We couldn't believe the amount of gorgeous girls that were everywhere down there. It was bikini season all year long and most girls made sure that they looked amazing in their skimpy swimwear. And the clothes of most girls in day to day life was much sexier and more revealing than up north as well. For someone with a fetish for sexy outfits like I have, it was an amazing place. And this just added to my secret problem, and made me even more self conscious. What added to that was the fact that because of all the time that girls spent staying in great shape, and maintaining perfect year round tans, for the most part they aren't the most well read or educated women to converse with. And this was the one area that I had something to offer in any hope of a relationship. My wit, sense of humor and ability to carry an intelligent conversation had no outlet with girls my own age.



I got a good job at an office and I was dealing with computers and account management for clients all over the country and was doing well for myself financially. My friends that had moved down with me ended up moving back due to lack of decent employment after about a year and a half, but I had made some friends and was moving up at work, so I stayed. Then the job market really crashed and the company that I worked for went belly up after the owner embezzled millions of dollars and fled the country. I was out of work and miserable for about five months. I was applying everywhere, and could not find a job that paid what I needed and had opportunity for advancement. I was quickly running out of money just to keep a roof over my head and food on my table, and I knew that what I had left wouldn't last much longer. Then I went for an interview that changed my life severely.



The ad was for a small company with amazing potential that was looking for one person to help with the overload of financial and computer analysis and maintenance that would free up the owner for more customer relations and sales. This was right up my alley. To say that I was surprised when I met the owner would be a drastic understatement. She was absolutely gorgeous and in her early thirties. She introduced herself as Kim and was a complete knockout. She stood at 5ft 8in tall with long wavy brown hair that fell past her shoulders and smoky grey eyes that hinted at something mischievous, but in a playful way it seemed. She was impeccably dressed in a tight, black, form fitting leather skirt that ended just past her knees as well as a obviously expensive ivory silk blouse that wasn’t inappropriate for a business woman but revealed plenty of what appeared to be a full C cup chest to get the imagination going crazy. She had on 3 in black open toed sandals and black stockings that did nothing to mask her perfect legs. Her makeup was light; but, accented her features in a sultry manner that drew your eyes to her full, light cherry colored lips covered with a gloss that gave the appearance of being wet, which is a look that has always driven me into a frenzy. I became a blubbering idiot immediately and was doing everything in my power to keep my jaw from hanging open as well as try to interview for a much needed job.



I was apparently able to maintain myself well enough so that the interview continued because she asked me if we could continue this over lunch. Of course I didn’t object, a gorgeous woman who could give me a job was asking me out to lunch. This was a new experience for me, regardless that it was because of an interview. Inside I felt thrilled and just grateful to be in her presence and very much intimidated. She had me completely under her thumb and I didn’t even realize it. The lunch went well and I really did have the skills needed that she required, and I ended up getting the job. I was on cloud nine.



The first few months were a typical working environment with some subtle exceptions. I didn’t see anything unusual and if I noticed anything, I just figured that you deal with different types of working relationships in an office with two people. Plus we were very busy, which kept my mind off the small peculiarities. Kim was definitely the boss, and her commands were to be followed when it came to business matters. I just naturally accepted the submissive role between us with no question. She had certain rules for the office that began appearing during that time. She said that she was constantly on a diet to maintain her figure and she would not tolerate anything that she couldn’t eat to be in the office, so I started eating the same diet that she did, mostly salads with small amounts of protein. Also she said that to keep up the pace that we were going with the hours that we worked we should be in the best shape possible, so she got me a membership to her gym and it just made sense for us to go together every morning. I thought this was great because I got to see her in usually a spandex leotard or shorts and sports bra every morning while we were on the treadmill together. Her toned and tantalizing body kept me in a dazed stupor constantly. Kim said that endurance was the most important thing to health, so only cardio was really necessary for our workout. She would joke about the muscle heads with the weights and how she didn’t find that look attractive at all. I agreed with her obviously, because I had lost about 15 pounds in the first few months alone due to the diet and workout regiment and had slimmed down to a thin frame. Working in a desk all day left the only little bit of excess weight in the thighs, hips and butt area. She had set me on a course to slowly feminize my body and I was clueless.



For the most part we got along great, and really did share the same likes and dislikes when it came to entertainment and style. When it came to style, it was more like I saw the impeccable taste and style that she had, and wanted to attain the same level as she did in regards to clothing, home décor, etc. She knew exactly what she was doing and occasionally she would make random concerned suggestions about something in my life. I thought it was very sincere when she said that I should let my hair grow even longer (at the time it was just touching my shoulder.) I was hesitant because I had never let it grow further so that I would not draw any more attention to my slight build and fairly feminine features; however, I knew she had an amazingly fantastic sense of style and I also had an hypnotic infatuation with this goddess. So I agreed and let it grow. Every now and then she would give me a well timed and placed compliment about my changing figure or longer hair which would make me proud but even more intimidated.



Since I was her only employee, I also took on many assistant duties, such as picking up and dropping off dry cleaning if necessary (and I loved the chance to see her sexy dresses and outfits), making appointments for her at salons, and spas. Things that I had not been familiar with previously because they are more female oriented things; but, I was becoming quite used to them and finding them less intimidating and more normal as time went on. Kim also had a look that would come out whenever she was displeased or upset about something. The look clearly meant that I or whoever else it happened to be directed at was wrong and there was no room for discussion. If I had made an error or failed her in any way, sometimes she wouldn’t say anything but just give me her look and I would feel ashamed and a little worried. I never even considered arguing, I just profusely apologized and vowed to do my best to please her with my work.



I had been doing well for the most part for quite some time until I came home to my apartment complex from work to find that there had been a fire in my building and two thirds of my apartment was completely ruined. I was told that I had to gather whatever I wanted to keep and leave that day, because the building couldn’t be occupied at all. The only things that I could salvage were half of my clothes which also happened to include my small collection of lingerie that I had with me to occasionally jerk off into. I phoned Kim to let her know what the situation was. She didn't hesitate and said to me as if i were a worthless idiot "you obviously have no place else to go, so be over here within the half hour, i'm busy and you need to hurry." This wasn't a negotiation and I didn't even consider disobeying her.


I arrived completely disheveled, feeling helpless, weak and feeling pretty low about my scenario. Kim on the other hand was the exact opposite, standing tall in her 4 in heels and a tight, light purple mini skirt with matching halter top. She said that I had already wasted her day and that if I'll be living with her then there are groundrules that need to be laid out. She showed me to her spare room that had once belonged to her rommate a few years ago. It was extremely feminine, light pink walls, a four poster canopy bed with sheer light pink canopy. There was a dresser and make up table that she kept alot of her excess makeup and clothing in. She told me that later on i could get a few boxes to put her clothes into in order to move what I had in.


I left my only remaining possessions there and continued the tour of her home. We would be sharing a bathroom, it was huge and richly decorated, but there was only a large jacuzzi tub and no shower. I asked her and she said that she only took baths, and from now on I would have to as well. Who was I to complain?


Then she showed me the kitchen, dining room and living room, and said that as part of my rent she wanted me to do the cooking and help with most of the cleaning. I still had no choice and so i just meekly agreed. Kim said "Good Boy" in a casual tone, but that struck a nerve with my submissive side, and I kept my mouth shut but started thinking about fantasies that involed Kim being dominant. The she dropped the biggest bomb on me when she said that part of the household chores would be our laundry. Not the drycleaning obviously but mainly her delicates. I pretended that I wasn't sure as I'd never done that before. She just smiled and said pretty soon I would be very familiar with lace, silk and satin. My reaction to her saying that, though not blatantly joyous, was enough to give my interest in lingerie away. She didn't say anything, she just stared me dead in the eyes until I had to look down.


She took me upstairs and said she'd help me unpack since I didn't have too much. I was still in shock and couldn't think of anything plausible why I didn't want her to go through my things. In my new room she opened a bag that didn't have any female clothes in it and started unpacking, the only other bag was the one with my entire stash of sexy lingerie. I just stood there and couldn't open it. After a minute she stood upright and told me help and unpack my bag. I didn't say anything yet again. She gave me her fierce stare and said she wasn't going to do my work and that I had better start to unpack. I just said I couldn't. She came over and slapped me across the face really hard. I made no defensive move. She said "when I tell you to do something you had better do it, or else, do you understand?"


I said very softly yes. "Are you hiding something in that bag?" she demanded to know. I couldn't meet her eyes or answer her, so she just took the bag and unzipped it. She immediately saw all the panties, bras and bikins that I had managed to acquire throughout the years. I was so ashamed. She just started laughing cruelly. I stammered that I would leave. "You're not going anywhere darling! Sit down on the bed right now."


Of course I instantly sat down. "We are going to have a long talk honey" Kim stated.


"It's not what you think"


"It's exactly what I think. I think that you like to dress up like a little slut in all these sexy, soft panties, bras. You even have a bikini. Hand that to me honey"


I handed her the bikini that was on top. It was a white string bikini with a triangle top and the bottoms tied on the side.


I said that i don't dress up in this stuff, that i just like the way it looks on girls and that feeling of the materials.


She told me to look at her and said "Well you are going to start wearing these, aren't you?"


I made no reply.


"Aren't you?"


"Yes, but I don't want to."


"What you want means nothing to me now, but I bet that you secretly do want to wear this stuff."


Kim told me to go downstairs and get a bottle of white wine and somefruit, that we were going to up here for a while. I followed her commands and went downstairs to the kitchen. i was in a panic about what just happened and how I could fix it. I came up with nothing. I was broke, with no other place to go. Plus she knew one of my humilating secrets and I was incredibly attracted to her.


I brought the things upstairs and she showed me the hall closet where my remaining male clothes were. "I am going to talk and you are going to listen, understand?"


"Yes I do" I whispered.


"These are where you only male clothes will go. This new situation has changed everything. Go back and sit down on the bed."


I did so and watched her saunter back into the room. She sat in the chair for the makeup table and faced me. She noticed that I kept looking down and said that I needed to listen to her exactly and that wasn't to ask any questions until she said so.


"I have noticed over the past few months how well you take orders at work, and never gave it a second thought. I just assumed that you weren't the alpha male type and I've enjoyed having an employee that would follow my orders. As you know I'm a dominant woman and have slowly began to manipulate you to be more feminine, especially with your longer hair and your slimmed down figure. I have always wanted to feminize a man and have really had fun with you up until now. I never thought it would go any further.


Then you called today and said that you needed a place to live and I couldn't believe that I might actually have an opportunity here. Your fate was sealed when I told you that you would wash my lingerie, and I could see the excitement no matter how you tried to hide it. But I didn't for a second believe that I would be so lucky as to discover your stash like I did. This moves my plan along way ahead of schedule. Consider your life as you know it over."


I was shaking visibly when I stammered "What do you mean?"


First off, you will continue to work for me; however, you are now my official secretary. At the office you can continue to wear male clothing for now, but that will change. When we are alone you will call me Mistress, and if anyone else is around you will refer to me as Miss Kim. Is this understood?"


"Yes"


"Yes what? Don't start off by misbehaving girl."


"Yes Mistress Kim"


"Good girl. I have a very big lingerie fetish, and clothing fetish. Plus I've wanted to feminize a man. I don't have the time to find a real man as my boyfriend and you're going to satisfy a lot of my needs. At home you will never wear male clothes. The minute you get home you will change into something appropriate. All of these drawers in the dresser are filled with sexy, slutty, frilly little underthings and some even naughtier ones with leather, vinyl and rubber. To be continued...

H

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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...

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4 years ago
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My shemale stepmom stepmother uses me and dad

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...

3 years ago
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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...

4 years ago
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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
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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...

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2 years ago
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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...

3 years ago
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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
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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
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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
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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
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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
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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...

4 years ago
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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
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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...

2 years ago
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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...

2 years ago
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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...

3 years ago
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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
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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...

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1 year ago
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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
3 years ago
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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
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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...

4 years ago
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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...

4 years ago
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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
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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
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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
2 years ago
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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
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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
3 years ago
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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...

3 years ago
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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...

3 years ago
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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...

1 year ago
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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
1 year ago
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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
4 years ago
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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...

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