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****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 femininity.

Her hair was dirty blond and loosely curled, and her face was quite beautiful. She was wearing makeup, but it was understated and complimented her face rather than drawing attention to the makeup itself. She was wearing a white sort of half-T-shirt that came halfway down to her belly button, exposing a flat, toned belly, but covering her boobs which stuck out way past her belly and threatened to bust out of her tight t-shirt. The only other item of clothing she was wearing were faded blue jeans which were cut off and made into shorts. They were covering an enormous, but perfectly-shaped ass and the tops of her large, powerful-looking legs. I also noticed that she had broad shoulders and slightly larger, well-muscled arms for a woman, but not so large or muscular that they looked unattractive.
When she greeted me, she gave me a quick look up and down, then smiled and told me to come in.

"Would you like something to drink?" she asked. I said "sure, what do you have?" She offered me beer or a frozen margarita. "Well, I'd like to keep my head clear for the work. Maybe later." "Well then, how about some Orange Juice?" she asked, and I agreed.

I said I'd like to get started and asked her where the PC was. She told me it was the second door on the right down the hall, I went in there and it turned out to be the bedroom. I couldn't help but notice a huge jar of Vaseline on her bedside table, along with tubes of K-Y jelly and Astroglide. The bedsheets were red satin, and there were no blankets or bedspread. By then I started to wonder if Shandra had more on her mind than getting her PC fixed.

I got started on the computer and a little while later she came in with the OJ. "Can you tell why it won't start up?" she asked as she handed me the juice. "I think so, and it shouldn't take too long to fix," I said. "Well, that's the best news I've had all day!" Shandra said, and gave me an odd smile that was almost a leer.

A short while later I had fixed the PC, much to her delight. When it booted, the desktop wallpaper was a photo of Shandra--naked. Her breasts were all I'd imagined... then I noticed she had a cock and balls!! Her cock was erect in the photo and looked about six or seven inches and about average thickness. My mouth dropped open as I stared at the photo. Shandra saw me looking at it, walked over to me, put her hand on my shoulder and said "Well, how do you like it?" I said "You look gorgeous. You have a great ass and huge, natural-looking tits!" She said, "And what do you think of my dick?" I was so excited I was actually shaking. I like to look at shemale porn, but had never seen a real, live shemale! "You have a nice big dick, it looks good," I said. Shandra grinned, and looked at me like a hungry tiger looks at fresh meat. She said, "Well you've seen me naked, now it's only fair that I see you naked too."

I was really trembling by that point, and wanted to leave, so I could get this all sorted out. It was all happening too fast for me. I said "Uh, I guess I should be going now." Shandra looked into my eyes and said "Oh, you can't go yet. I'm not done with you!"

That both thrilled me and scared me a little, and I didn't know what to say. I had fantasized about being with a shemale many times, but never thought about actually doing it. All my past sexual experiences had been with women. I wasn't prepared for this, and part of me wanted to leave, but another part was very curious about what might happen.

She moved closer to me, took my hands and put them on her breasts. I started fondling them and could feel the nipples start to harden beneath the t-shirt and bra. She started pulling my shirt off. "Wait," I said, "I'm not sure I want to do this." Shandra replied "You can't expect to leave after seeing me naked and feeling me up. You've got me horny now and you have to do something about it. I can tell you've never been with a shemale before. I'm glad to have the privilege of taking your virginity. Don't worry, I'll be gentle!" She laughed evilly. I tried to back away but she had a hold of my shirt and pulled it off, then she wrapped her strong arms around me and started kissing me, forcing her tongue past my lips. I was getting hornier but still a little scared, and I was trembling and my arm and leg muscles felt funny and weak. I couldn't fight her off, and wasn't sure I wanted to at that point.

Her hands moved down and started squeezing my ass cheeks. "I can't wait to get in there!" she said. At the time, I had no idea what she meant!


She quickly took off her shirt and bra and then took my head into her hands and slowly but forcefully pushed my face into her chest, and swung her torso back and forth, gently battering my face with her tits. By this time, I was hard as a rock! She then released my head and started unzipping my pants. I half-heartedly tried to push her hands away, but she batted mine away and said "Stop resisting. You have to let me see you naked, you're not getting out of here until you do. Just relax, all I want to do is see that luscious ass of yours and then I'll let you go." Well, that was quite a relief, and I was very flattered, never having my ass referred to as "luscious" before.


I said, "Well, I guess that's fair." I let her take off my pants and underwear. As I stood there naked, facing her, with her huge breasts sticking out from her chest; I looked down and noticed a very large bulge in her shorts. I felt flattered that Shandra was so turned on by me, but worried about the thing that was trying to bust out of her shorts! She looked me up and down and said, "Nice cock. Now turn around!" I did as I was told. Shandra said, "God, what a great ass you have," then she grabbed my butt cheeks and started gently squeezing them, then squeezed harder and harder until it actually started to hurt just a little. I was about to say something, but she spoke first. "Lay down on the bed," she said. At that point I was incredibly horny and all the doubts about what I was doing were gone. I was really hoping for a blowjob! So I lay down on the bed on my back, and she said "No, turn over." I wondered what she wanted me to turn over for, and she saw the concern in my face and said "Don't worry babe, I just want to fondle and massage that ass of yours some more."


I said OK and turned over. She got up on the bed, standing over me for a minute, and then straddled my legs so she was facing my butt. She started rubbing and massaging my ass again, and I was getting so horny I was about to explode! She stopped what she was doing, said "you just stay there a minute, and don't look back--I have a surprise for you" and stood up. I again did as I was told, and she was walking around on the bed for a minute. Just as I started to wonder what she was doing, she sat back down just like before and immediately started massaging and gently slapping my ass. It was nice, but something seemed different. She then leaned over me to the bedside table, reached into the Vaseline jar and pulled out a good-sized glob of it. I figured she was going to give me a Vaseline massage, and I could hear her working the lube into her hands, or so I thought. Suddenly, I felt something large, warm and slippery rubbing my ass! I looked back to see what was happening, and gasped as I saw that she had taken off her shorts, lubed up her crank and was rubbing my ass with it!! Damn, it looked a lot bigger from that angle than it had in the photo! "Just relax, honey buns, I can tell this is your first time at this and I promise I'll be gentle." she said. My boner wilted quickly as I realized what she was planning to do, and I nearly panicked! I said "Wait, I don't want this! Get off me! You can't do this!!"
She replied angrily, "I'm not letting you get away with that prick-teasing shit! You march your cute ass in here, parade it around in front of me, let me get my hands on it and then after you've gotten me all horny, you think you can say no?" Then she continued in a much gentler tone, "Just relax, sweetheart. I'm going to take care of you. I know how to please a man... you just have to let me fuck you first and then I'll get you off afterwards." My world reeled--how is this possible? An hour ago I was on my way to a computer repair job, now a shemale is trying to **** me?

I started to try to get up but she leaned over me and held me down. In that position, I couldn't do anything, and I could feel her throbbing log resting on my butt crack. She said "Don't fight it babe, if you fight it, it'll hurt." I couldn't believe my ears... I was about to get ****d by a she-male, and she was worried that she might hurt me??

The next thing I knew, she had positioned her dick so the tip of it was pressing gently on my butt hole. I felt my sphincter tighten up involuntarily and was afraid she'd thrust in then... my whole body was shaking with fear. But she just held it there, until my asshole relaxed, then she pushed against it just a tiny bit, at which point it went taught again, and again she stopped and held it there. My bunghole relaxed again, and she pushed it into my ass just a little. My butt clenched again and this time it hurt a little, because it couldn't close all the way as the tip of her erect penis was in there! She held it rock-steady, though, and this time my anus let loose even sooner than before. Slowly, slowly, she began to slide the rest of her log into me. I didn't clench again, but it was horribly uncomfortable--it felt like it just kept going in and in forever, filling me up beyond all possibility.

"Ahhhh," she said, "That's nice. That feels so good..." She was still sitting on my legs, and then she straightened out her legs behind her and lay down on me, which cause her penis to slide in even further! She just lay on me for a while, not moving, and said, "GOD it feels SO GOOD to be inside you! You're going to be the best fuck ever, your pussy is so hot and tight!!" When I heard that I felt a strange rush of exhilaration. I could feel her boobs pressing into my back and feel her breath on the back of my neck. I felt myself starting to get hard again! I couldn't believe it, I was getting ass-****d and this was making my dick hard?

Still laying on me, she arched her back to pull her cock out slightly, then thrust it back in slowly. She kept doing this, and it was starting to feel good to me! I was getting butt-fucked by a shemale, and I was liking it! Hell, I was starting to love it! She started to moan, and began to pump my butt a little faster. She kept this up for a while, telling me how good it felt. My cock was so hard it was actually starting to ache a bit! I couldn't help but let out a moan or two… then she pushed herself partially off me, straightening her arms, and started fucking me like some crazed a****l! Her thrusting into my ass was moving my whole body on the bed, and my cock was sliding around on the satin sheet. It felt so good... then I realized I was going to have an orgasm!

I tried to hold back, but I couldn't. I started to come, and it was the most intense, mind-shattering orgasm of my life! With each orgasmic contraction, I could feel my butthole tighten convulsively on her log, and as soon as my orgasm started, she began moaning and grunting louder, then with one powerful thrust, shoved her fuck stick deep into me and held it there. As I was coming and feeling my asshole tighten and release, tighten and release on her cock with each wave of orgasm, I could also feel her cock pulsating inside me as she came too! I swear I felt her jizz squirting deep into me, and with each of her orgasmic pulses her whole body contracted powerfully as she cried out, which made my orgasm suddenly double in intensity! It seemed to go on forever--I think I came at least twice in rapid succession, and it felt like my head and my heart were going to explode!

As we finished coming, she collapsed on top of me, with her cock still inside. After that incredibly powerful orgasm, I was more relaxed than I've ever been before or since.

We lay there like that, breathing hard, and I felt her penis slowly soften and shrink, but it stayed in my butt. We stayed like that for a while, and I think one or both of us may have dozed a bit. I'd just been fucked, practically ****d, had my ass used by a gorgeous "woman" for her selfish pleasure. It was the most beautiful feeling I had ever felt!! I could have lay there forever with her on top of me and her cock in my ass and her boobs mashed onto my back. I wanted to do it again, and often. I wanted to be Shandra's sex doll.

Suddenly she suddenly said, "Oh shit, what time is it? I have to get to my yoga class!" She pulled out of me and went into the bathroom. When she came out she was dressed again, and said to me, "Bathroom's in there, sweetie. Get cleaned up and dressed quickly, ok? I don't want to be late. How much do I owe you?"

I was puzzled. She said, "For the computer repair, silly!" I had completely forgotten about that! I was still reeling with bliss from the experience, and all I could say was "Uh..." She smiled and said "Don't worry about it now; you can give me the bill when you come next week." I said, "Huh? Next week?"

Shandra replied, "You fixed the PC, but I'm sure I'll need you to come back every weekend for tune-ups and stuff, so it doesn't crash again." She gave me an evil grin, and added "And don't forget, you're my bitch now. You're my fuck-toy and I'm going to take good care of you. Now get dressed and get the hell out of here so I can go to the yoga class!"

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“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...

3 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...

1 year 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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First love with a shemale

This happened around 10 years back. I never had a chance to share my experience. After getting some free time at my work recently, i thought of sharing my erotic stories.I will cut the chase and jump into action. I had been browsing horny shemale videos for a long time but never had the opportunity to spend time with. The place where i stay does not have good transgenders and 80% of them are just fake and try to loot money. I searched the craigslist and from one of the websites luckily found an...

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...

Gay Male
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...

3 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
1 year 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...

2 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
3 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...

4 years ago
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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...

2 years ago
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Fucked by shemale

I've always thought myself as a straight guy. However, I always fantasised about serving a big cock. The problem was that I didn't fancy guys. That is when I came across shemale porn, OMG, what could be better?! A hot ass girl with a huge cock. Unfortunately, convincing shemales that aren't escorts are hard to come by, if not impossible. I started scouring escort sites and found a local shemale offering her services. She was Latino, 5"10, big tits, and best of all, and 8inch cock. I was really...

3 years ago
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Fucked by shemale

I've always thought myself as a straight guy. However, I always fantasised about serving a big cock. The problem was that I didn't fancy guys. That is when I came across shemale porn, OMG, what could be better?! A hot ass girl with a huge cock. Unfortunately, convincing shemales that aren't escorts are hard to come by, if not impossible. I started scouring escort sites and found a local shemale offering her services. She was Latino, 5"10, big tits, and best of all, and 8inch cock. I was really...

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