My Sissy Roommate free porn video

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I swear he’s always like this. So worried about everything. I don’t know how the kid has survived this long. Probably because I’m always here to calm him down.

It’s kind of funny, not many people can see Andrew and me as being friends. Him being a meek, petite, nerd who’s often confused as a girl and me a muscle-bound, jock who gets all the girls. We’re complete opposites from each other.

And yet, Andrew and I have always been best friends. We grew up next door to each other, I’m always the one getting him into trouble, and he’s the one who tries to think a way out of it. Of course, he used to get picked on a lot in high school, but not when I’m around.

He and I are like peanut butter and jelly. Oil and vinegar. Wine and cheese. Milk and cookies. What I’m saying is, we just work well together.

I couldn’t imagine going to college without him.

We arrive at a party at a classmate’s sorority, she begged me to come after class. The place is packed with girls everywhere. Definitely a lot more girls than guys.

Sarah’s eyes light up as she sees me. Her blonde hair neatly coming down to her shoulders. “You came!”

“I told you I would,” I laugh. “This is my roommate and best friend, Andrew. Andrew, this is Sarah, the girl in my math class.”

“It’s nice to meet you,” she says. “Do you guys want something to drink?”

“Yeah, sure,” I shrug.

We follow her through the house, into the kitchen, where a giant jug cooler is. She grabs two cups and hand them to us. “Normally we charge $5 per cup for guests, but you two can drink on me.”

“Aww, thanks. Such nice hospitality.” I give her my heart-stopping smile which turns her cheeks pink. I can admit she has really beautiful eyes. So green and verdant.

We fill our cups with jungle juice and follow Sarah out to the back porch.

“So, how long have you two been friends?” she asks.

“Since kindergarten,” I laugh.

“Wow, that’s so cool,” she says.

“Yeah, we grew up next door to each other,” he adds.

“It’s so rare to have remain best friends in college, more power to you,” she says.

“What about you? You still with your best friend?” I ask.

“Well, not really. We sort of broke up in high school,” she says.

“Ouch, what happened?” I ask.

“She fucked my now ex-boyfriend behind my back,” she says.

“Ouch, what a bitch,” I say.

“Truly backstabbing,” she says.

“Definitely not a true friend,” I add.

“Yeah, not like the two of you, I’m so jealous,” she says. “But, I do have some pretty cool friends in the sorority.”

“Nice, we’ve made some friends as well. So what made you join a sorority?” I ask.

“My roommate convinced me, speaking of her, here she is!” A girl with dark brown hair and matching eyes walks up. “Becca, this is the boy from my math class I was talking about! Arthur, meet my roommate, Becca.”

I hold out my hand and she shakes it as she stares into my eyes. “It’s nice to meet you, Becca.”

“You too! Sarah has been talking nonstop about you,” she says.

“Has she?” I ask, raising an eyebrow. “And what mean things has she said about me?”

“Oh trust me, it’s all good. And you definitely add up to her stories,” she says. “With all the good things she’s said about you, I was beginning to think you weren’t real.”

“Well, I hope not to disappoint,” I say, giving her my lady killer smile. “By the way, you should meet my roommate.”

“You mean there are two of you?” she asks.

“No, Andrew is far smarter than I am,” I laugh as I put my arm around him. He tenses up as her eyes fall upon him. Her expression changes from giddy anticipation to a look a girl would give to a puppy. Not exactly what I was hoping for.

“Aww, he’s adorable,” she says. “You know, you’d be so perfect for my social experiment.”

“Oh, Bec, don’t!” Sarah says.

“Aww, come on Sarah. You know he’d look so good.”

I raise an eyebrow as Becca grabs Andrew’s hand and pulls him behind her. “Come, you need to meet my partner, Kenzie.”

Sarah grabs my hand. “We should probably follow them.”

“What’s her social experiment?” I ask.

“Ehh, you’ll see,” she says.

I follow her into the house and I see Becca talking to another girl with red hair. They both look at Andrew with excitement before dragging him upstairs. Sarah and I follow after them.

We go into one of their rooms where Becca and the red-headed girl who must be Kenzie are holding girl clothing against Andrew’s frame. The look on his face says it all. Shock, embarrassment, humiliation and if I wasn’t mistaken, a little bit of excitement.

“Come on, you should definitely try these on for us,” Becca says.

“I was afraid this would happen,” Sarah says as she drags me into the room and shuts the door. “Come on guys, don’t do this.”

“Aww, come on Sarah. Don’t be a buzz kill. You know he’d look cute all femmed out.”

“Wait, you want to dress him up as a girl?” I ask.

Andrew looks equally mortified and giddy.

“Don’t you think he’ll look so cute with this skirt on?” Kenzie asks holding up the skirt against his waist. Her eyes go wide as she brushes against his crotch. “Oh my god, do you have a boner?”

“No!” he stammers.

“Yes you do!” she says. “You’re enjoying this as much as we are!”

“I… I…” Andrew studders.

“Don’t be ashamed,” Becca says. “I think it’s so hot. You have to do it now. Just try on a few outfits. Please.”

Andrew’s eyes meet mine. He looks frozen. I’m not sure if he wants me to get him out of this situation or give him permission.

“Come on girls, just leave him alone. Look, Andrew. You don’t have to do this,” Sarah says.

“Oh come on, Sarah. Don’t act like you’re not into this. You were so into it when we were discussing it earlier,” Becca says.

“Yeah, it’s fun to talk about it, but to actually force someone to do it is another thing entirely,” she says.

“We’re not forcing him, we’re just persuading him,” Kenzie says.

“What do you think? You’re his best friend?” Becca says.

“It’s not up to me, it’s up to him,” I say.

Kenzie leans in a whispers something in his ears and his eyes light up.

“So, will you do it?” she asks.

“Okay, okay, okay!” he says.

“Wow, what did you say to him?” I ask.

She smiles. “Just offered him a blow job.”

“Kenzie!” Sarah stammers.

“Relax, it’s just a blow job,” she says.

“Not really,” I laugh. Andrew glares at me.

“What do you mean?” she asks.

“Andrew’s never been with a girl before. Not even for oral,” I laugh.

“Aww, he’s a virgin?” Becca asks.

Andrew looks as if he was just punched in the stomach.

“Sorry bud, it slipped,” I say, taking a sip.

“Now, let’s get those clothes off of you,” Kenzie says.

“You… You promise you guys won’t tell anyone?” Andrew asks.

“This won’t leave this room. We all promise we will tell no one,” Becca says, crossing her heart. “Now, let’s get these clothes off you.”

Both Becca and Kenzie attack Andrew and start stripping his clothes off. Once they get him naked, which by the way, he desperately tries to cover himself up with his hands, they start scouring through clothes.

Andrew is as red as a tomato. The weird thing is that I can’t stop staring. His ass is better than most women I’ve been with. So plush.

Andrew’s hazel eyes meet mine before he quickly looks away.

“Here, put these on,” Becca says as she hands him a pair of cute pink panties.

Andrew’s eyes go wide.

He looks at Becca and then back at the panties. Reluctantly, he takes them from her and slowly puts them on. They barely cover his bubble butt.

Fuck me. From the waist down, I would never be able to tell that he was a boy. At least from behind. His legs are as hairless as any girl’s I’ve come across. Am I seriously getting turned on by this?

Kenzie hands him a skirt. Again, he hesitates but eventually complies and puts it on.

Then, Becca, has him put on a pink sports bra and a white blouse.

Afterward, Kenzie brings him to the bed and puts a white pair of thigh high stockings on him.

“Okay, all that’s left is makeup and we’ve got to do something about your hair,” Becca says.

Becca grabs her makeup bag while Kenzie gets a pair of scissors, one of those hair bands. Andrew looks up at her with fear in his eyes. “Relax, I’m just going to trim it up a bit. It won’t look that much different.”

He closes eyes. “Whatever…”

She grabs a spray bottle and doses his hair and then goes to work trimming it. By the time she’s done, it looks vastly different. Adorable to say the least. His black bangs drift off to the one side and it’s slick and cute.

“Don’t open your eyes just yet,” Becca says as she starts layering on the makeup. It doesn’t take her long. “Okay, you’re good.”

Both Kenzie and Becca take a step back to admire their handy work.

I got to say, if I didn’t know any better I would’ve totally believed Andrew to be a girl. A cute one at that. I actually want to fuck him. Badly.

“Wow,’ Sarah says. I almost forgot she was in the room. “You two have outdone yourself. She looks amazing!”

“And you tried to talk us out of it,” Becca says.

“I was wrong. You’ve done a great job,” Sarah says.

“He’s so cute,” Kenzie says. “Now let’s see how well he does down at the party. I bet everyone will be convinced he’s a girl.”

“Wait a sec, you never mentioned anything about going out like this!” Andrew says.

“Relax. No one will be able to tell you’re a boy and no one will know who you are,” Becca says.

“Besides, every girl in this sorority will make sure you’re safe,” Sarah says. “As president of the fraternity. I will make sure no one hurts you or makes fun of you.”

“I didn’t know you were president,” I say.

She smiles at me.

“I don’t know…” he says, as his gaze falls to his feet.

“I say, why not? You’ve already gone this far. Besides, you look sexy as hell,” I add.

He looks up at me wide-eyed. “You think so?”

“Yeah, definitely.” I nod my head.

“Okay, okay. I’ll do it,” he says.

“Yes!” the three girls say in unison.

The girls grab Andrew and drag him downstairs before he even has a chance to breathe. I follow them downstairs. I’m still amazed at how they transformed him. Although, they did have a good base to build off. I can’t get his ass out of my head. Such a perfect bubble butt.

Becca and Kenzie flaunt the poor kid around the house, introducing him to just about everyone. He looks so flustered. His face is as red as a stop sign.

“So, what do you think?” Sarah asks.

“I just can’t believe it’s really him. He looks so different,” I say.

“Kenzie and Becca could make just about anyone look like a Victoria Secrets model. Although, they’ve really outdone themselves with your roommate,” she says.

“I can’t believe how natural he is. Sure, he’s a bit flustered, but I think deep down he really enjoys it. Like, the clothing just brought out the inner girl that was there all along,” I say.

“Yeah, that and the fact that he’s definitely gay,” she says.

I look at her with a raised eyebrow. “How do you figure?”

“The way he looks at you and acts around you, it should be obvious. He has serious deep feelings for you,” Sarah says.

“I don’t know. We’ve been friends since Kindergarten. Don’t you think I would’ve known?” I ask.

“Hmmm, maybe. But look at him. Look how that guy is flirting with him. He’s so flustered,” she says.

I glance over to see real douchey looking guy hitting on Andrew. He looks like he’s the type of guy to have two different girlfriends. A total tool.

And yet, Andrew is eating it all up. He looks like a natural girl. He can’t possibly be into this guy, can he?

Holy shit! The guy just swooped in and started kissing him! I can’t let this continue.

“I’ll catch you later, Sarah.” I head over as they break apart. I grabbed Andrew’s arm. “You ready to go?” I ask.

“Aww, you really want to go right now?” he asks.

“Yeah, let’s get out of here,” I say.

“Huh… How about I just meet up with you later,” he says.

“Are you serious? You’re going to risk everything for that guy?” I ask.

His eyes go wide. “You saw me?”

“Of course. Now let’s go before he realizes you’re not who you say you are.” I grab her hand and she reluctantly follows me.

The entire way back to the dorms we walk in silence.

Finally, in the elevator, he speaks up.

“You’re not mad at me, are you?”

“Why would I be mad?” I ask.

“I don’t know, you just seemed like you were,” he says.

“No, I’m not mad at all.”

“Okay… Cool. You’re not going to tell anyone back home about this, are you?” he asks.

“Of course not. You’re my best friend,” I say.

“I think I’m gay,” he says.

“Yeah, I kind of figured that,” I say.

“Really?” he asks.

“You did just kiss a guy,” I say.

“Do you really think he would’ve hurt me if he found out?”

I nod. She looks down away. I mean he… It’s so confusing.

The elevator stops at our floor and we make our way back to our room.

I unlock the door and as soon as he shuts the door, something takes over me. Something so primal. I pin her up against the door. Her eyes go wide as I press my lips against hers.

At first, she just stands there. Then she starts to kiss me back. I brush the hair from her face as our lips part.

As her eyes meet mine, I can see she’s wanted this for a long time.

“Don’t stop,” she breathes. Once again, I’m kissing her as my hand slides down from her face. I slide my fingers across her flat chest and slowly make my way down south. I reach to find my way down to her skirt. Slowly, my fingers work their way up under the fabric, touching the silky white thigh highs before I meet her bare skin.

I don’t stop there. I slide up until I find the panties covering her ass.

She shimmers at my touch. I can’t hold myself any longer. I hike her legs up around my waist as she wraps her arms around my shoulders. I carry her to my bed.

I climb onto the bed with her in my arms. We kiss as my fingers dig underneath the fabric of her shirt, slowly sliding it up. Our lips part as I tear off her shirt.

She looks up at me with those hazel eyes. I place my hand against the soft skin of her face and lean down touching my lips against hers. She slides her hands against the skin of my back, pulling me closer. My tongue pushes past her lips as my other hand runs across her chest, sliding under her sports bra and groping her nipple. I slide off of her and roll her onto her stomach.

I tear my clothes off before straddling her thighs. I lift up her skirt to reveal that panty-clad ass. So perfect. I grab each cheek. Her ass is so pillowy. Squeezing it, I kneed it and spread her cheeks apart. I grab ahold of the hem and slowly pull her panties down to reveal such a plush ass.

Scooting down, I spread open her cheeks and slide my tongue up and down, making her shutter. I meet her butthole with the tip of my tongue and dive in. She squirms and wiggles her butt. I give it a playful slap causing her to gasp out.

I give her little starfish a good tongue bath. Fuck she taste so good. And her ass feels so good in my hands. I love squeezing it.

I can’t take it anymore. I want her so bad, I have to fuck her. She’s mine after tonight.

I spit on her as and on my cock, getting both nice and wet.

I scoot up and smack my ass between her cheeks. She looks back at me, so nervous. I lean down and kiss those lips of hers.

“Arthur? I… I’m a little…”

“Don’t worry, I’ll take it nice and slow at first. But Andrew?”

“Yes?”

“After tonight, you’re mine,’ I start to press my cock between her cheeks. She grits her teeth and grips the bed. Fuck her ass is so tight.

I slowly push and wiggle my cock until it finally pops inside her. “Urgh…” She groans out. “It hurts!”

“Shhh…” I bring my hand over and brush the hair away from her face as tears roll down her cheeks.

I kiss them away. “Don’t worry, I’m going to take it nice and slow.

Little by little, I inch my cock farther into her tight little bum. Every time she groans and squirms, I let up and allow her ass to adjust. She brings her hands back and spreads apart those asscheeks.

My cock sinks a little further inside her. She bites into the pillow. I pull a little bit of my dick out and watch as it dugs on her ass. Slowly I push my cock deeper than before. She gasps for air. Fuck, it’s just so tight. It’s like sticking my cock into an ant hole.

Ever so slowly, I start working my cock in and out. Fuck, it’s so hot watching my dick dug on that butt. Practically brings her hips with me. She whimpers with each thrust.

The more I push into her, the more of my dick she can take. Finally, I plunge all 8 inches inside her as my hips touch her ass cheeks. I can feel my balls rest on top of hers.

I lay down on top over her and wrap my arms around her. I move my hips back and forth slowly at first.

Hearing her start to moan is music to my ears. I start thrusting a little harder. She cries out and grits her teeth.

Fuck it feels so good to be inside her. I’m lost in the moment. It’s hard to even think let alone remember that it’s Andrew underneath me, taking my cock. Does this make me gay, to be fucking another man? No! Andrew isn’t man, not anymore. Not dressed like that. Not with an ass like that. Andrew’s my girl from now on.

I’m not going to let her go.

“You’re my girl from now on,” I whisper in her ear as I slam into her. Hearing her moan only makes me want to fuck her harder. And I do, thrusting harder and harder into her. She cries out, moans and groans with each thrust. I wrap my arms around her neck and she grabs onto them as I let loose on her ass, pounding my dick deep inside her.

Her moans are such a sweet melody. Her ass grips my dick so tightly.

She clamps down hard around my cock. “Urgh, I’m cumming!” she shouts out.

I don’t let up and I pound the cum out of her. But I can’t last much longer.

I hilt my dick all the way inside her as the tension in my balls becomes too much.

“Urgh, fuck!” I scream out as I erupt inside her tight little ass. She moans as I fill her but up with a thick load of cum.

Slowly, I continuing thrusting inside her as my dick squirts load after load inside her.

I collapse on top of her as my cock goes flaccid in her tight bum.

We’re both desperately trying to catch our breath.

I kiss the back of her neck before I pull out of her ass. A rope of thick cum keeps us connected before it breaks off and lands on her ass. A glob of my thick seed squirts out of her gaping butthole.

I give it a soft slap before rolling onto my back.

She takes a couple of minutes to recoup before looking up to me with a glazed over look.

“Did you really mean what you said?” she asks.

“What part?”

“That I’m yours?”

I reach over and pull her into my arms. “Andrew, seeing you all dolled made me realize how much I really like you. I mean, It’s confusing. I’m not gay or anything. But to me, just now, you weren’t a boy, you were the most beautiful girl I’ve ever seen.”

“So you didn’t really mean any of it?” he asks.

“I don’t know, this is all confusing. Aren’t you just as confused as I am?” I ask.

“Yeah. At least when it comes to dressing up as a girl. I always believed I was a man, but now… I’m not sure. I liked being dressed in girls' clothing. I enjoyed getting hit on by guys. I kind of knew I was gay. I never told anyone because I remember how people treated the few kids who came out at our school. And if I”m being honest, I’ve always had a crush on you.”

“Wow… Really?”

“Yeah, I think you’re the hottest guy ever. And you’ve always been so nice to me. I felt like we had this connection,” he says.

“We do. I just didn’t think it was this kind of connection.”

“So now what?” he asks.

“Like I know…”

“Do you still want me?” he asks, his eyes look so sad as if he’s expecting me to say no.

“I mean, I’m not gay or anything, but if I’m being honest, I do. But I want you as a girl,” I admit.

Hope you enjoyed the story, feel free to leave any feedback in the comment section below. Give it honest rating.

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(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

2 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

1 year ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

3 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

3 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

4 years ago
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iPad Roommate

“Pffff, another sweater.” Aaron says as he holds up the red, green, and white Christmas garment is aunt sent him. “At least this one as an actual cool design on it.” Ian says as he smiles at his roommate. In a small house in a secluded neighborhood covered in snow, two men in their mid-20’s enjoy a simple holiday together. With the pandemic still at large, both guys have spent their family time on their laptops’ cams. Wishing their loved ones Happy Holidays and having shipped their gifts to one...

1 year ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

4 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA. Uncle Penny: My transvestite uncle. (Aunty...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

2 years ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

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