Moms Teaches Son To Become A Sissy Sperma Slut free porn video

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I never knew my dad.

That's not an excuse for what I've become – and that's not to say I need an excuse – it's just a simple fact that some people find relevant when trying to examine what I've become.

Anyway, he was killed in a plane crash before I was born. Technically, he was killed in a plane crash while I was being born, but he died without knowing that. He'd been overseas at a business conference when my mom called to tell him she was going into labor, and had boarded the first plane he could back to North America. Ironically, it wasn't that long, turbulent, twenty hour flight that killed him, but the short little jaunt between New York and home on a twin-engine commuter plane.

I've seen photos of him, of course, and I've even see a poor copy of a commercial his company did where he walks on camera, shakes a football player's hand – an enormous black hand, not that has anything to do with what I've become either – and says, "Hello."

Hello.

That's the only word I've ever heard him speak, and it turns out that was actually dubbed over by one of the other guys in the firm, after my dad's death. So, really, I have a few photos, a bad video, and someone else's voice to account for my memories.

I regret never knowing him, but I don't regret what I've become.

As for my mom, she was a struggling medical student before I was born. She wasn't studying to be a nurse, but an actual doctor. It was almost unheard of at the time, but she has always been a strong, confident, independent woman who knows what she wants – and is not afraid to go out and get it. She wanted to be a doctor, and that's what she was going to become. The pregnancy put a temporary halt to her studies, but she had been determined to return to school the semester immediately following my birth.

Unfortunately, my dad's death put an end to those plans, but it also meant she never really had to worry about it. Even as a junior executive, my father was heavily insured. The company insured all of its employees, with additional policies on those who were required to travel for work. I don't know what the actual dollar value was, at the time, but I know my mom was smart enough about investing the two payoffs to never have to work again.

You don't care about any of this, of course, but it's important that I establish the proper expectations. When I tell people who I am and what I do, they automatically assume I came from a broken home and an unhappy home life. They assume I must have grown up in abject poverty, watching my mom do whatever it took to put a little stale bread reheated Kraft Dinner on the table. The imagine all number of daily abuses, and assume that I must have suffered tragically to explain what I've become.

I want you to know that is so not the case!

Even without a dad, I wouldn't call our home broken. My mom and I were very close, as much best friends as were family. There was nothing sexual or inappropriate about our relationship, so get your mind out of that gutter, but we have always been very honest and open with each other about sexuality. That, I will admit, likely has something to do with what I've become, but only in that it has allowed me to embrace my place in life without fear or shame or doubt.

As for poverty . . . well, like I said, my dad's insurance policies left us very well off. In the time it took for a single stupid goose to fly into the plane's right engine, our house, our car, and even my dad's boat were all paid off. That meant my mom only had to worry about utilities and food, and the interest from the insurance settlement alone covered that and more. I wouldn't say we were rich, but we were very comfortable.

I distinctly remember the first time I saw my mom come home with a man. I was twelve at the time, and finally old enough to stay home by myself. Of course, I had to keep the doors locked, the window shades down, and the television on in the living room. My mom even had the gardener – a mean looking black man who, in hindsight I still suspect was doing more than just trimming the bushes – come over around ten o'clock to move the cars around in the driveway, and then exit through the back yard. I'm not sure any crook is really stupid enough to fall for that ploy, but it seemed genius to me at the time.

Anyway, I should have been in bed, but I decided to stay up late to watch the late-night talk shows I heard other k**s raving about at school. To be honest, I really didn't see what they thought was so great, and was actually on my way to bed when they came in.

My mom was dressed in a gorgeous red cocktail dress, with shiny red heels and a matching purse. I'd watched her get dressed and do her makeup before she left, and helped her to pick out the shoes and purse. Before you start smiling and figuring you suddenly have me figured out, I wasn't queer or anything like that. I just enjoyed watching the act of transformation my mom went through once in a while. She was an attractive woman around the house, but she was an absolute stunner when she went out. Even as her son, I could appreciate that.

She'd always been a pale woman, blessed (or cursed, depending on when you asked her) with freckles all over her body. Seeing her come through the door, though, with that black man towering over her, she looked like such a tiny little ghost. I'd never really thought of her as short, just normal, but either she was really short or he was really tall, because she looked like a c***d as she turned around and stepped into his arms.

Over the next few years, my mom would bring home a lot of different men. Some were tall, some were short. Some were skinny and wiry, others were muscled and bulky. Some dressed like the teachers at school or the men at the bank, and others dressed like the k**s at school or the punks looking for a purse to snatch outside the bank.

What they all had in common – that I could see, of course – was that they were black. The fact that there were all extremely well-hung and full of cum was something I wouldn't discover for a few years yet.

It was the summer of my fifteenth birthday when I finally, fully understood my mom's relationship with these men. We were out laying by the pool – me out in the sun, her beneath the biggest patio umbrella you'd ever seen – when I caught a glimpse of something on her back. Curious, I waited until she rolled over to pick up her soda, and then leaned in for a look.

It was a tattoo. The very idea of such a thing on my mom's backside thrilled me. Tattoos were dangerous things, the kind of things you saw on dangerous people. I'd never known anyone with a tattoo until then. Her tattoo was a red heart, about four inches wide at the top, set in the very small of her back. It would have been hidden by anything other than a bikini bottom, so I couldn't even guess how long she'd had it. I understood the heart, of course, but I couldn't make sense of the lettering inside.

' W4BBC' was written inside that heart, in carefully drawn, very feminine, stylized lettering.

We'd never had any secrets between us, and she'd always welcomed any questions I might have, so I asked her what it meant. For the first time in our lives she paused, as if she might not answer. I was devastated. What could be so horrible that she couldn't even speak of it to me, her son? I mean, I knew tattoos for dangerous people, but had she done something wrong? Was she ashamed of the beautiful artwork that adorned her flesh?

I remember how she looked at me, as if she wanted to tell me, but was afraid. She looked so excited, but she also looked scared. I smiled, and started to tell her it was okay if she didn't want to talk about it, but she shook her head, laughed at herself, and then invited me to sit on the end of her chair so we could talk.

That was the afternoon that she told me, proudly and openly, that she was a Whore 4 Big Black Cock. That's precisely how she said it. Whenever my mom used those words, you heard the capital letters at the start of each one.

Whore 4 Big Black Cock – that's what the W4BBC stood for, and the heart around it represented the fact that she loved everything about being a Whore 4 Big Black Cock. It had all started quite accidentally, with that first date I witnessed a few years ago (as it turned out, even she had been afraid of the gardener). She'd never intended for it to happen, and hadn't gone looking for it, but that first Black Cock had been so Big, she knew she could never give it up.

She told me to think of my own cock at its hardest – she'd seen it very well the night we had 'the talk' and probably a few times after, through my open bedroom door at night – to imagine it twice as long, and to imagine it as three times as thick. That, she told me, was only the beginning. She told me to think of my messiest orgasm – she emptied the garbage and cleaned my sheets, so she knew what I was capable of – and then imagine each one making twice the mess, and then imagine having five of them at once.

That, she assured me, only began to explain her addiction to Big Black Cock. She loved it, it made her happy, and she was not at all ashamed to admit that to me.

With what little I knew about sex at the time, that made perfect sense to me.

It didn't suddenly fill me with a sense of inferiority, or suddenly crush my masculinity. I didn't feel the least bit insulted by the comparison to my own cock, and honestly didn't feel as if there were anything wrong me with. Instead of making me feel small and weak, the conversation simply informed me that black men were bigger and better. There was an 'average' or 'normal' size somewhere between us, and I knew that I fell pretty close to that mark - they just exceeded it.

There was no sharing of intimate details, no reminiscing about past lovers, just a very frank discussion about what she loved and why. To a neighbor peeking over the fence, we could have been talking about the weather, the shape of the clouds, or what we were going to have for dinner that night. When you lived such an open and honest relationship as we did, conversations like that really weren't a big deal. It explained the tattoo, helped me to better appreciate the men she brought home and, most importantly, confirmed that my mom was a happy woman.

When you're fifteen, living at home, and politely aware that you have it better than most of your friends, your mom's happiness really is important.

*******

That's part of where my story starts, but to understand how quickly and how drastically my life would later change, you also have to understand other half of my story.

From the moment puberty hit, about a year before the W4BBC tattoo revelation, I'd been a very happy little sissy cross-dresser.

Now, this might be something you can blame on being raised by a single mom, but I don't know that our situation had much of an impact on things. Really, I think I would have developed my fetish for femininity regardless, even if I'd been raised with a strong father figure and a few older brothers. It was nothing that my mom forced on me, but it also was nothing that she discouraged.

The more opportunities I have to meet with other sissies, the more I love her for that attitude.

By the time we had that conversation by the pool, I already had a closet full of feminine attire that was almost as well-stocked as my closet of masculine attire. It was a closet I only explored around the house, but I was okay with that. I could spend all day trying on outfits, feeling the caress of silk and satin across my skin, and enjoying the delicious thrill of high-heels on my feet. I hadn't yet begun experimenting with makeup, but I'd watched my mom transform herself enough times that I felt pretty confident I could do it – and do it well – whenever I felt like it.

Whereas my mom was a bold woman, commanding and strong in reds and blacks, I was a soft little sissy, submissive and meek in my pinks and yellows. There was nothing in my closet that couldn't be considered soft, sweet, cute, or adorable. Dressing started out an entirely sexual experience, I freely admit, but it soon became something that I did to relax, de-stress, or just feel comfortable.

It just felt right . . . it just felt like the real me. It was nothing I really discussed in detail with my mom – it was enough that she accepted it – and I certainly never brought it up in front of my friends at school. In fact, I laughed along with them whenever a lisping, prancing, gay sissy showed up in a movie, even as I secretly studied his every word and his every word to see what fell into my definition of myself.

I laughed, but I also learned . . . with none of my friends the wiser.

By the time my life changed forever, I was spending my every moment inside the house dressed as a girl, and had even ventured out to the mall a few times with mom to go shopping.

*******

Thanks for sticking with me through all of the boring stuff, but I think it's really important to understand that even the most seemingly normal, well-adjusted, happy boy can become what I am today.

In fact, if you're reading this, it might very well be that you're on your way to joining me. If so, then please accept my sassiest, silliest, sissiest squeals of congratulatory glee. There really is nothing better, although I'm glad most boys don't see it that way.

That just means more for me (or us, if you really are on your way to joining me)!

It was the night of my eighteenth birthday party that circumstances conspired to change my life forever. At the time, I was absolutely devastated that my friends had all backed out of my weekend birthday celebration – all for good, entirely valid reasons – but I had tried to soldier on anyways. Unfortunately, a weekend in a private, well-stocked party pad wasn't nearly as exciting as it seemed without company there to help me enjoy it.

So, when it became clear on the second night that no latecomers would be joining me, I headed home to raid my closet. If was going to be alone and drunk, with access to a well-stocked bar and pay-per-view television, I was going to get dressed up and enjoy it.

The first thing I noticed when I got home was the number of cars parked around our house. Our driveway was full, the front lawn was covered, and both sides of the street were occupied from the stop-sign on Park, to the yield sign on Strauss. My mom was clearly having a party of her own, and the last thing I wanted to do was intrude. I almost headed straight back to the party pad, but by that point I'd played through the weekend so many times in my head that I needed to grab some things from my feminine closet first.

It gives me chills to think how my life might have been different if I really had turned around.

Strangely, the main floor of the house was dark. Other than the kitchen, the lights were out, and there wasn't a soul to be seen. I figured they were partying out back, so I hurried up the stairs to my bedroom. When I got to the top of the stairs, I saw the sliver of light from beneath my mom's door, and heard the noises coming from the other side. It wasn't that they were loud or rowdy or anything like that. In fact, as she told me later, the men themselves were being rather quiet, never talking to one another, and only whispering to her. As for my mom, she was a little too occupied to be speaking . . . if you know what I mean.

If you don't, then I really don't know what to say, other than to hope the surprise is a pleasant one. I know it was for me!

Of course, I knew none of that at the time, but knew well enough not to disturb her. As open and honest as our relationship was, our one rule was that closed doors meant privacy. If doors were open, we were both free to come and go as we pleased. Bedroom, bathroom, laundry room, den, it didn't matter. Day, night, morning, afternoon, or evening, it was all the same. Naked or clothed, alone or with company, an open door was an invitation.

A closed door, however, was a polite sign that we wanted a little privacy – and we both respected that.

I went down the hall to my room and made sure the door was closed behind me. If she had a guest in the house, I didn't want him wandering into my room by mistake, especially while I was getting my clothes ready. I spent the next half hour in the closet, pulling clothes out, holding them against one another, keeping some, and putting the rest back. I had it in my mind that I wanted two sets of outfits, with a little room to improvise, depending on my mood.

First, I wanted a cute, sexy, college girl outfit in case I got drunk enough to leave the party pad. I knew that was a possibility, and it excited me. For that, I had a few very short skirts, some tight blouses, knee-high socks, and my eighty-dollar Victoria's Secret pink panties.

Second, I wanted something slutty and sexy for being alone in the party pad. For that, I grabbed my second favorite corset (I needed somebody to lace me into my favorite), two pairs of fishnets, a garter belt, and my frilliest, laciest, sissiest panties. After, for relaxing, I grabbed an adorable pink peignoir set that my mom had just bought me, but I hadn't yet had a chance to wear.

I had everything packed, then decided I really did have to be prepared if I was going to go on a drunken stroll around town. So, I left the overnight bag on my bed, and then made my way down to the bathroom to borrow some of mom's makeup. Halfway down the hall, though, her bedroom door opened and two of the tallest black men I had ever seen in my life walked out.

I'm not sure why I panicked, except that I didn't want to intrude on my mom's fun. I quickly ducked into the hall closet and watched through the crack to see if they had noticed me. As they passed, I got my first close-up look at big black cock . . . and what a look it was. Obviously, I couldn't measure them, but I'd put them both at about 9 inches long, and so thick it would take both hands to masturbate them. More than that, their balls were absolutely enormous. I swear you could have taken my cock and balls, balled them up, and stuffed them into either man's sac, and still have room left over.

I didn't find them particularly attractive or anything, and certainly didn't feel a sudden urge to jump out and devour them, if that's where you think I'm going with this. Instead, I simply admired them, appreciated them for their beauty, much like I'd appreciate a priceless sculpture at the museum. Yes, they were big and they were beautiful, and I could certainly understand why mom was a proud whore for big black cock, but seeing them didn't suddenly turn me gay.

The moment they disappeared down the stairs, I rushed to the bathroom, grabbed the makeup I needed, and then headed back to my room to finish packing. While I was there, I suddenly heard a group of deep, male voices coming down the hall, accompanied by mom's giggles of amusement. I couldn't overhear everything they were saying, but apparently they had dared her to do something with a drive thru, and she was determined to collect on the dare. I peeked outside my room and counted at least a dozen black men, not including the two who had already gone downstairs.

I gave it ten minutes to be sure they were gone, and then emerged with my overnight bag, ready to head back to the party pad.

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Hey sirA few months ago I went to Fort Armstead outside of Baltimore.  I heard it was a cruise spot.  I went to check it out but to add excitement I wore lingerie under a hoodie and sweat pants.  I got there about dusk and walked around the ruins.  There were several guys walking around but didn't see any action.  I walked into and out of the bunkers. I walked into one and saw a old couch in the corner. Then I heard some noise and turned to see a guy hanging against the wall in a darken corner...

2 years ago
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Sissy Stepson 9 Forced to Suck

Part 9 - Forced to Suck "Get over her you bitch NOW!" screamed and angry Maryann. Caroline's aunt grabbed his limp red puny dick and put the knee high. "What's a matter limp dick sissy, can't get it up for a woman, maybe you need some perversion or more man cock" crowed Aunt Maryann. "Look sister, he's getting a little stiff, he must love to be degraded" said his stepmother wickedly. "Lay down in front of my feet and Phil put a knee high on your cock and start jacking off in front of...

3 years ago
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The Reawakening of Sissy Jackson

The Reawakening of Sissy Jackson By Cassandra Morgan The memories came at night, when his consciousness was not on guard to stop them. A little boy, rushing across the playground to his mother. She laughs and picked him up, kisses him on his lips. He is a small boy, frail, too weak to play ball sports with the other kids. He plays on the swings...but not too high. He plays hopscotch. He plays jump rope. The mommy does not care. She likes having her little boy close to him, and if...

2 years ago
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Lick ass n sucking n fucking sissy slut

I have a story for my xhamsters Ppl I was married for 19 years me and wifey we was open about marriage we use to do everything together we us to talk about everything we use to have sex party so one time we had a party so my wife set this up herself she ask me this party is special it is a month away i said OK but than she hit me with a twist we can't have sex until the party i was like what she said yes no sex no jackoff no nothing all i want u to do is watch porn and I going to pick the one u...

2 years ago
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The Big Bad Bullies and the Submissive Sissy Slut

The Big Bad Bullies and the Submissive Sissy Slut I was always a target for older and stronger boys. I guess in playground hierarchy a boy that liked to daydream about silly things would have to assume there would be some teasing. After all I wasn't as rough and tumble with other boys my age. I was something of a sissy you might say and a weakling as well. I often suffered terribly at the hands of bullies. I liked to play alone mostly, with my sister's dolls. I also coveted her pretty...

1 year ago
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First time turning into dirty sissy slut

If you are reading this now and finding it disgusting, i suggest you don't comment. Am just an african teenage of 21 of age, living in my own apartment, i am single as far as i remember and being a sissy is my fantasy which i realy wish to turn true. dont get me wrong guys, i realy do want a girlfriend, but trying another man cock in all position makes me hard many times. well luckily this is a story of how it became a reality. it happened few weeks ago from now. it all began when i...

3 years ago
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Andersonville 21 Sins of the father Sins of the son

"Good morning, Miss Anderson," Crius said in a formal tone. "Please, call me, Linda," I replied. "Only if you call me, Crius," he answered. The Titan God smiled, but I detected no warmth to it. "Okay, Crius." I returned his smile with some reservation. I couldn't put my finger on it, but I didn't feel at ease with him. When he had asked me out to breakfast, I had been tempted to say 'no', but my curiosity had gotten the better of me. "So, what can I do for you?" "Nothing,...

3 years ago
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Hypno sissy slut

It took a while to get a sense of reality. First my sight: blurry and hazy like my mind, light streamed through the window, bouncing off the soft white covers I was lain on. I blinked, shaking the hair that was covering my eyes, trying to see my surroundings. A largre screen TV was in front of me. I twisted my head left, and right, trying to take in the room. The room was made up of mirrors, and a blonde girl was in the centre, pillows underneath her stomach, arms and feet padlocked to the bed....

3 years ago
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The Making of a White Sissy Slut

The Making of a White Sissy Slut When he replied to my ad online, Steven said he was an attractive, 30- something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by saying, "Well, no one's ever told me that I was unattractive." When I suggested that was because...

1 year ago
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The Making of a White Sissy Slut

The Making of a White Sissy SlutWhen he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side.  When we met in person, I was more than a little bit disappointed.  Attractive was a stretch of the imagination and I told him so right off the bat.  He acted as if I’d said something to offend him and responded by saying, ?Well, no one’s ever told me that I was unattractive.?  When I suggested that was because no one had...

3 years ago
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The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

4 years ago
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Sissy Stepson Part 5 Pantied and Punished

Part 5 - Pantied and Punished Carl begged his stepmother not to spank him and he pleaded, "I'll be good, I will never try your things on again, please!" "To late, you can't be trusted and must be properly punished, but first I want the truth about why you did this. If you don't tell me the truth I will make sure your father knows, his family, your friends and everyone at school!" Carl shook with fear and started to cry. "Please I couldn't help it, I am attracted to your sexy...

3 years ago
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Caught and made into a sissy slut

It was for real this time. No fantasy. Reality. I was dressed up in red: fishnet stockings, g-string, and a babydoll. I was wearing a metal chastity cage that was pulling my clit down, and it was a clit, it only half filled the cage. I had a new cock too - a black face dildo which was double-ended. In my new role, I had to jerk it as I was fucked in my pussy and I was being fucked. She had fucked me so hard that I was completely submissive to her, sucking on my gag with wild abandon, a true...

2 years ago
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Moms Stockings My Sons Cum Bucket

Introduction: A slut going wild Moms Stockings: My Sons Cum Bucket I have wanted to fuck my son for a while, ever since he graduated high school this year and really buffed up over the summer working construction. It was then, one random day, while he was in swimming trunks to go for a dip in the pool that I noticed that my son had turned into a man. In fact, my son had grown into a very handsome man, a virtual replica of his deceased father (who died serving his country two years ago). I...

4 years ago
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Sissy Slut

Sissy Slut by [email protected] ? I was naked and kneeling in the corner of the room furthest from the door. My head was bowed and my forehead touched the floor. I was shivering in anticipation because I had been that way for what I guessed to be more than half an hour, although it is hard to tell in such circumstances. Finally I heard the door open and the sound of stiletto heels on the painted concrete floor. They came towards me but I did not dare to look up. I knew that to do so would be...

2 years ago
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The Making of a White Sissy Slut

Truth be told, Steven wasn’t gruesome; he was merely average. Average for a white boy unfortunately is just shy of ugly. Thin lips, pasty skin, thinning hair, non-descript features, he was nothing to write home about. I had plans to change that. The ad to which he replied was a proposition to completely transform a white boy into a sexy, desirable, cross-dressing, sissy, and insatiable, cum-crazed whore for black cock. I didn’t pull any punches and he knew what he was in for so there was...

3 years ago
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Mistress sissy slut

Waking up, sometimes, can be rather difficult to do, especially when you know that you were d**gged the night before. Or, at least you HOPE it was only the night before. And this time, it was far worse than the first times. So many things have changed about me from the first time I was d**gged, unwittingly and unwillingly, though as I look back, I can’t really say that I am upset about the outcome of each of these times. Well, I have to admit that I was, kind of, pissed off the first time, as I...

3 years ago
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Sissy Stepson Part 2 Sissy Heaven

Sissy Stepson Part 2 ? Sissy Heaven Carl knew she was going shopping, so he feigned being sick to stay home. He saw that his stepmother wasn't wearing her stilettos and this excited him. They would be his to explore and touch. She bitched at him, "You're not sick!" "Yes, I am, I feel sick to my stomach." plead Carl. "Well, I am still going shopping, I am not waiting on you today, you're on your own!" bellowed Mrs. Monet. "No problem, I just...

1 year ago
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Turning my Roommate into a Sissy Slut

The work is pretty tough, although I like it here better than my last school. My name is Aaron Walker. I'm a junior in university now, but it's my first year here. For my freshman and sophomore years, I attended a local community college near my town just to get in some of the simple course requirements for my major. I found that it was a lot cheaper than if I took those classes here. But the easy stuff is over, and I'm a 'real' college student, now. But what doesn't help is the fact...

4 years ago
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Sissy Stepson Part 4 Stepmothers Test

Part 4 - Stepmother's Test She crossed her legs and began dangling her high heel again and Carl became excited. His sissy stick started to stick up as he watch the dangling show and fashion models prancing on the run way. He had no where to escape and his stepmother noticed her panties bulging with his sissy cock. She nonchalantly let the shoe fall on the carpet and said, "Well, missy are you going to pick my shoe up and place back on my toes or can't you get up!" "Yes, ma'am, I...

2 years ago
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Cuckolded sissy slut

My partner was a really kinky bitch. I remember going to her house and having wild sex all weekend; sucking on her tits and pussy, and fucking her all weekend long. On the Saturday night she stuck a finger in my arse and I was suddenly changed. It all escalated from then on in.That first finger had hit the spot, causing me to crumble. My legs were spread as she fingered my hole. 'Get up,' She said, and I did. She guided me so I was facing away from her. I was watching her in the mirror, as she ...

3 years ago
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Sissy Stepson Part 3 Caught in the Trap

Sissy Stepson Part 3 ? Caught in the Trap He was worried about the stain until he started watching a game show with the sexy female host. She had a stiletto's like he was wearing and was dangling them. Once again Carl's sissy stick became hard and began oozing translucent sissy cream all over the nylon and panties. He sat there for ten minutes watching the dangling, mesmerized and in a sissy dream like state with glazed eyes and an oozing cream stick confined...

2 years ago
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Andersonville 12 The Day Linda Anderson Came To Town

I slid the report into the proper file just as he walked into the room. Dennis Butz stood there wearing his three-piece suit, looking as handsome and charming as any man could. But I was not to be tamed by his charm. "Hello, Linda," he said with a friendly grin. "Judge Herns isn't in today," I replied back in a frosty tone. "I'm not here to see her." "My plane leaves in less then an hour Dennis, what do you want?" I slammed the file drawer shut and walked past him to my desk...

3 years ago
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Sissy Dogging Slut

I sit nervously twitching as I speed through the night my locked up clit twitching with excitement. Why? Because I am heading towards the local dogging spot and I know when I get there I will be a big attraction because of what I am wearing. That is, pink PVC thigh high boots, pink fishnet stockings held up by a pink leather suspender belt. As you have guessed bit of a theme going on here! A pink PVC mini skirt which is in fact was more of a micro skirt since it only covered a quarter of...

1 year ago
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  • 8
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Sister Made Me a Sissy Slut

There I was lying on my back. Cum leaking out of my asspussy (anus), dried cum all over my face and, body. I’m wearing nothing but torned pink lacey satin panties soaked in cum and, sweat and, there was a small smile of satisfaction on my face. My name is Tanuj or Tanisha as they now call me. I’m a 16 year old boy 5’6 thin but not skinny, pretty much hairless (totally now). It all started about a couple of weeks ago. I always had a cross-dressing fetish but, I was not sure if I was gay. My...

Incest
1 year ago
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A Mom And Her Sissy Son Banged Together

Sorry for the delay in between guys, got busy with some work. People who have not , please do so to follow this part. After a few weeks of the previous incident, nothing much happened. Dad moved to a new city for his work and it was only me and my mother at home. One such Sunday, she left for the gym at 10 am and I sat down to watch porn on our TV. I connected my phone to my TV and started watching some hot shemale porn. After some time, I heard the doorbell ringing. I was sure that mom would...

Gay Male
3 years ago
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  • 16
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Pretty Pinky Life Of A Sissy In Prison

Two inmates walk from the cellblock to where a correctional officer sits at a desk. The C.O. is a middle aged black guy. One of the inmates is a buff black guy; the other is a small slightly built young, Caucasian. The black inmate is dressed in standard prison garb. He has the Caucasian by the upper arm - the way a man walks a woman - and is walking him to where the C.O. sits. The Caucasian has on brown work boots with dark socks rolled just above the tops. He has a towel tied around him,...

2 years ago
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Becomming a Sissy Slut

Sandy's LifeMy name is Sandy Johnson. I chose that name 35 years ago because I like Sandy and I knew a hot female with the last name Johnson. I first remember finding my mothers underclothes in the bathroom closet. We she and my Dad would go out I could go in the bathroom and put her slip on and find a pair of dirty panties in the dirty clothes hamper. I still love the feeling of an old fashion girdle!I dated in HS and went to college, married, went to war, had c***dren, divorced, married again...

2 years ago
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Chrissie Becomes a Sissy Chapter 2

Chapter 2 Chrissie becomes a sissy It was Friday morning and I was sitting in the doctor's surgery waiting to be administered my weekly dose of oestrogen and my three month shot of Depo-Provera, which is the drug which chemically castrates me. I have been on Depo-Provera for the last three years and I could tell the last dose was wearing off as my mind was increasingly focused on submissive sexual fantasies. Nevertheless, Friday is my favourite day because I have begun to view the...

1 year ago
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  • 21
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Transforme me to a little devot Sissy Slut

I dream of being trained by a dominate man or a bi couple to a sissy house and sex slave. im a bi boy and i want to be a devot good gurl. l want my little cock locked up permanent, servicing my alpha in all ways he likes it, i want lern take his big cock completey deepthroat whitout a gag and i want lern to cum like a gurl over the only way that is allowed anal ! I will not look at women any more unless I am ordered and i will never inside a pussy ! if I am trained by a bi couple then I would...

3 years ago
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Pussy Whipped Sissy Slut

                       Pussy Whipped Sissy Slut - Chapter 1 (revised)        Uncle Bill and his pals had used me pretty hard last night and most of this morning. I guess I made a pun, since there were plenty of hard cocks working away to loosen up my tight asshole and make face fucking me a much easier task. I have to admit that I just love to be the center of attraction, and I was still glowing from all the attention I'd gotten. They kept me securely restrained, although they didn't need to...

1 year ago
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Pretty Pinky Life of a Prison Sissy

The black inmate walks the sissy up to the C.O. The inmate and the C.O. talk and the C.O. gets up and walks over to a cleaning supply closet just around the corner from his desk, and unlocks the door. Then he walks back to his desk & sits down to read a newspaper. The pimp walks his sissy to the cleaning closet and turns on the light. The sissy is carrying a tub of Vaseline. He sets the Vaseline on a shelf and moves a couple of mop buckets toward the rear of the closet. Then he unwraps the...

4 years ago
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From Straight Top to Sissy Slut

Hi! I am Shreyas, a 20-year-old college student from Chennai. Or at least, I was three months ago. Now I’m Shriya, a cross-dressing sissy slut whose sole purpose in life is to please alpha men. Let me tell you a bit about myself before I get into the story. I used to be a handsome, fair-skinned guy with a fit body and decent muscles. I was never into men. I never fantasized or checked out guys ever before, at all. I was in a relationship with my girlfriend of 2 years when this incident...

Gay Male
2 years ago
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Mommies little sissy slut

I have been crossdressing for years now not known to my mother (or so I thought). she is the only person I live with at the moment. when she was going to be out for a few hours I went to her underwear drawer and inside was the most sexy, silky, feminine underwear set I had ever seen complete with calf length stockings and a garter belt. I wasted no time stripping off and sliding on the sexy underwear, next I found her makeup bag and applied some red lipstick and black mascara. that was when I...

4 years ago
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Turned into a Sissy Slut

Turned into a Sissy SlutMy name is Mark. I’m 19, and am around 140 lbs, thin, with a kind of girly ass. I began to fully embrace my love of dicks by watching hours of gay porn and at the same time embraced my feminine side by buying and hiding a lot of women’s clothes. Still, by the time I was 18 and going off to college, I had not done anything with a man. It’s not that I didn’t want to or that I was scared, I just didn’t know any gay or bi people around my neighborhood.Luckily I was able to...

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