My Life As A Shemale Part2 free porn video

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Many things happened over the next few months, for one, I healed maybe better than I ever was, I discovered that there was another side to me and most important I met Tim. He was the one that found me and maybe even saved me. A middle aged man who once had a daughter, I know that because I am now living in her bedroom, sleeping in her bed and wearing her clothes.

But lets rewind for a moment, the first thing I remember waking up is seeing Tim. He asked me my name, "Danny" I said, he introduced himself as a doctor that didn't practice anymore and now lived by himself. He told me that I was safe and didn't need to worry about anything for the moment, other than getting better. He also apologized that I was wearing his daughters nightgown and he would get me something a boy would wear. I had thanked him and fell asleep, I did feel safe. Over the next few weeks we talked about where I was from and what he did and his life. He became a father figure I never had, he was kind and caring, he never approached me in any fashion that was considered lude and gave me my privacy, a favor I returned as well. The first couple of weeks he did examine me regularly, as a doctor would, the most painful part was when he checked my anus to make sure that I was healing well; and under his care I was.

One evening we sat in the living room after dinner and it was the first time I started to talk about what had happened the night before we met. I didn't realize it then but he had waited for me to start talking to him first, he listened as I explained. In the end, I paused and he asked me, "I think there is a little more you want to say". So I told him, "There was something about this that happened to me and I don't know how to describe it, something good". He nodded and waved his hand to go on. "If it hadn't been for the constant fear that I was going to die, I might have enjoyed some of it, I think, I dunno, I 'liked' to be handled. He was rough and disgusting and yet...". Tim smiled for the first time, like he understood but not making fun of me, he explained "I am not the kind of doctor that can help you figure things out but I have life experience that I can share, maybe the loss of your parents, maybe the foster homes or maybe you are wired different than the average person. I think in the end you should do what pleases you as long as you don't hurt other people."

We sat in silence for awhile and I started to think, I thought I was ashamed but felt better now, Tim gave me confidence to say what I had been thinking, "I know you bought me boys clothes but I really liked your daughters clothes, do you think, I mean, would it be ok if I...". I trailed of and Tim smiled again, "Wear them?". I nodded. He said, "Yes you may but you need to do something for me then". I thought, here it comes, Tim frowned at my expression, "No not that, I would like you to meet someone, she comes by sometimes and helps me with certain needs, things I need to get done, well, I would like you to spend some time with her." I immediately said yes, I had no idea at the time who she was but a friend of Tim's had to be a good person.

After our 'talk' I went to my bedroom, it was beautiful, the four poster bed had a canopy with silk hanging down, tied with pink ribbons. The sheets were soft flannel that gave an immediate feeling of comfort. The dresser was full of clothing that were his daughters, she may have been around the same age as me but certainly close to my size. My first need was to get the clothes off Tim had bought and I tossed them in a corner, the next was the top left drawer of the dresser filled with underwear. I wanted the feel of the panties, no, I needed it. One by one I tried every single one and at the bottom was a pair of soft silky panties, those became my favorite. But the bulk of my penis kept slipping out to the side, moving it this way and that, I could not fit into it the way it was meant to be worn. Next came skirts, sweaters, stockings until I looked on top of the dresser, the was a mirror and below it a box of ribbons. Since my hair had grown out even more, I could try wearing them. I spend some time styling my hair in the mirror and in the end I thought I looked like a cute girl.

Tim said nothing the next morning when I arrived at the breakfast table dressed in his daughters clothes, I wore a plaid skirt and satin button up top, knee high socks and buckled shoes. I did top it off with a bow that was hanging a little of to the side. He came over to me and looked, I thought he was going to tell me to take it off, "Danny, your bow is a little off, can I fix it for you?" I smiled and nodded, and so he did. "Better". We went about our days as if nothing unusual had happened, when one morning Tim said over his coffee mug, "Danny, remember that friend of mine I told you about? Well she will be coming by this afternoon, I would still like for you to meet her, maybe talk to her." I agreed and looked forward to this, it would be a change of pace since I had no friends other than Tim.

The afternoon came and sure enough the doorbell rang, Tim went to answer the door since we agreed that I should never answer it. I was in my room and could hear them talking but not about what. After what seemed like a long time there was a knock on my door and Samantha came in, she was drop dead gorgeous. I just sat on my bed a gawked at her, which seemed to make her laugh, "Hi Danny, I am Samantha but you can call me Sam, can I come in?". Her short leather skirt and top showed her petite and amazing figure but most of all I loved her boots, also black leather with high heals. I nodded and she just flung herself on my bed next to me, she was amazing, instantly likable and didn't seem to have a care in the world, "I love your room Danny, just like my old room at my parents house." She just started chatting away and after awhile I asked her about her clothing and we started to go through the closet in which she found things I didn't realize were there yet. She suggested some matching things and laid them out on the bed, she had taken her boots off and thought we try on some things, I immediately said yes and we were chatting away like old friends. She started to strip until she was in her bra and panties, standing in front of the mirror holding a top up, "Danny why don't you try this one on, I think it will fit you better than me." I slowly moved over to her and felt a little ashamed, "I need to tell you something Sam, I am not...I am not really", she flashed that smile again, "A girl?, I know, but it doesn't matter to me unless it bothers you?".

She stood there, not pushing or saying anything just waiting. I slowly started to take off my clothes, my skirt was the last to come down, my penis of course sticking out sideways from underneath my panties. Her eyes grew considerably bigger, "Wow Danny, you could give a grown man a run for his money, awesome. I can help you to tuck it away a little better if you like." I told her "please."

She kneeled down and started working on me, handling me a little more than I think she needed to but it felt good in a way. She asked me to spread my legs a little pushing my balls upward and almost into me, sliding my penis between my own legs and toward the back. Then she pulled my panties back up tight, "Well I think that is about as good as its going to get without some special fitting wire, you are simply too big sweetie!" We laughed and she started to take off her panties and bra, "and its only fair that you get to see me naked too!". I had to admit that I was curious, after all, I was a boy starting to come into manhood. I shyly looked at her perfect breasts and then down over her flat belly, I saw she had a piercing in her belly button which I thought was very becoming to her then my eyes moved on to her shaved slit. "Its ok to look Danny, you can even touch me if you like". I came closer, it was difficult to move with my penis between my legs. She saw that, "Why don't you take your panties off so you can be more comfortable?". I did as she asked and did feel immediately better. She touched my penis and let her hand slide back and forth over it, I reacted as any boy would and started to grow.

After a minute, it may have been more, I looked at her slit, I tried like hell to relax but noticed that she was getting wet. So I asked her and she moved me toward the bed, explaining the basics of women's sexual anatomy and needs. "I see" is all I said, we were sitting on the bed and she continued stroking me, pointing out the drop coming from the tip of my, now very big penis, she explained the why's and how's of men and their needs. Then at the end she said, "Listen Danny, you don't have to but I would like to suck on your penis because I am really horny now and you are beautiful and I would like to do this as a present to you so you can remember me always as your first, would that be ok?" I nodded, felt like an idiot too. She moved in front of me and her tongue touched the tip,touching the drop and placing it in her mouth, she seemed to like it. Then she slipped her lips over the tip again, taking it in her mouth and the warmth was perfect and silky and wet. I cannot describe the feelings that went through me and I came fast, I mean super fast. My body started to shiver and I had no control, this was new to me and she continued, her eyes looking at my face seeing what was happening, she backed off a little, just enough for my penis to come out but leaving her mouth open, stroking me with her hand, my pristine white sperm shooting into her mouth, even missing some of it and sticking to her lips and cheek. She closed her mouth and swallowed.

She gave me time to compose myself, I reached out and touched her face, sliding my finger through my sperm bringing it on my fingertips and carefully to my own lips. Not knowing what it would be like and still not sure if I was disgusted or excited to try, I stuck my tongue out and tasted for the first time my own cum. I decided it was nothing to write home about but it wasn't horrible either. She could tell by the look on my face, "Its ok sweety, at first it wasn't my cup of tea either, but tell me how you feel?". I saw the big Sam smile and said, "It was incredible, I still feel like that if I got up I wouldn't be able to walk right". We laughed at this and I continued, "I love the way you look and the way you feel, your skin is so soft and perfect, I wished I could look like you, make others feel the way you made me feel just now, this is the most incredible thing Sam." She moved back for a moment as if she didn't expect me to say that, "Danny, you can make others feel like this, you could make ME feel like this, that is what your penis is for and I can show you how to use it too if you like." I sat on the edge of the bed, my penis now flaccid. Looking at her, I thought I wanted to explain better that I wanted to be the one looking and doing what she did, little did I know, she already understood me perfectly. I wanted to tell her about how I felt about Tim and that I thought that I was falling in love with him, wanted to take care of him. Maybe another time.

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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...

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