Cuckold Sissy Pimped Out free porn video

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My wife and I have been exploring he cuckold lifestyle for a little over 2 years now. I love watching her getting fucked and having her pussy stretched by a well endowed man. When we first started doing this, I would just watch until the other guy left and then I would get my chance to reclaim her. After we had a few experiences, she started to include me a little more. At first she would just stare at me while the other guy was fucking her. That is still one of the hottest things I have experienced. Then she started talking to me. Things like, do you like this or he feels soooo good inside me.

As we both became more comfortable in our own roles, we started to expand into other aspects of cuckoldry. We bought a male chastity device and she threw out all of my male underwear. I'm now kept in chastity and wear panties every day. The longer she keeps me in chastity, the hornier I get. After just a week in chastity I started sharing all kinds of kinky fantasies with Mandy. I loved seeing her play with other men's cocks and I shared with her that I had given other guys oral in the past. The only time I had done that was in a glory hole at an adult bookstore I used to go to. She liked the idea of watching me suck a guys cock but we had a difficult time finding suitable men that we could both share.

After being locked up for about 45 days, I asked her to help me realize one of my fantasies. I didn't think she would actually agree to it but she said that since I have been such a good cucky she would help me live out one of my fantasies.

We placed an ad on CL to find 3-5 guys to use me as their sissy sex toy. We decide to invite at least 4 different guys to come to our hotel room and have sex with me while she took pictures. We decide to invite them to our hotel room, only 1 at a time. Each one gets 30 minutes. The first one to arrive at 8 and the last one to leave at 10.

We both reviewed the responses and started to reply to the men. Many of the men want to have sex with Mandy as well but she told each of them that she would be fully clothed and only watching. After narrowing the candidates down to 7, she tells me that you think a couple of them are cute.

I asked her "Do you want me to just fluff them for you so you can have sex with them?"
She responded with an innocent smile "Maybe :)"
"We can invite the two guys that you like over first and if you want me to hand one of them over to you, you should give me some type of signal."
She just smiled again and said "OK :)"
"Once I get the guy hard you can turn on your vibrator and start playing with yourself. If I hear the vibrator, I'll tell him that you want to feel his cock inside you. Then I'll hand him a condom."
"Mmmmmm Yesssssss"
"If the first guy has sex with you, we should just let him stay and you two can play with each other while I let the next guy in"
I could tell she was thinking of the possibilities when she responded with "What if I want the second guy too?"
"Same thing, just turn on your vibrator and I'll tell him to move over to your bed. Should we invite 4 or 5"
"Definitely 5"
"Ok :) I'll invite them and set the times."
"Make sure you invite that guy with the big cock first. I liked him "
"Ok, but I sure hope you decide to play with him. I don't think I can take him inside me."
"Oh you will take him"
"Yes Ma'am"

I email 7 of the guys we agreed upon. I invite 5 of them to our room at a designated time and explain that they will have 30 min to get their rocks off. I tell the other 2 guys that we will contact them if we have a cancellation. I tell the first 2 guys not to expect Mandy to play but if she wants to play with you she will let me know. The rest of the guys are told that Mandy may have her own play partner when they get there but she will not be playing with them.

Friday arrives and we check into our room. We shower get dressed and open a bottle of wine. Mandy takes a couple of pictures of me and send them to the guys that have been invited to the hotel. With the message: My Sissy is ready for you.

The first guy arrives at 8pm. Mandy opens the door and lets him in. She leads him to the bed where I am on my knees waiting. Mandy then sits on the other bed and says: "Here he is. All ready for you. You have 30 minutes to do whatever you want with him. I'm just gonna sit on this bed and watch and take pictures."
Guy 1: Are you sure you don't want to join in.
M: No, I'm just gonna watch.
Guy 1: Ok, well I should get started
He kicks his shoes off and unbuckles his pants and lets them drop to the floor. He slides his underwear down and lets them drop to the floor then steps out of them. He holds this massive cock in front of my face. It's gotta be an inch longer than Mandy's favorite toy and even fatter. I look over at Mandy and she has a big grin on her face. It's obvious she is staring at his cock.
Is this what you want sissy?"
me: "mmmmm.. yes"
I lean forward and take him into my mouth while he's still standing by the bed. I can hear the pictures being taken right away. He is just standing and watching my head bob up and down on his cock. Then he takes his shirt off and pushes me back so he can lie on the bed. Once on the bed, I start sucking him again. This time he grabs the back of my head to control the rhythm and slowly moves his cock in and out of my mouth. Then he looks over at Mandy and says:
"This sissy bitch knows how to suck cock, he's pretty good"
Mandy replies: "I like to use his mouth too :)."
"I see his cock is a lot smaller than mine. Are you sure you dont want to feel this "
Mandy just smiles at him and picked up my phone and started snapping pictures. He turned his attention back to me and started moving my head up and down on his cock a little faster and a little deeper. Only a few seconds later I here the vibrator turn on and lift my head off of his cock to see Mandy guiding the vibrator down to your bare pussy. I look up at him and tell him "I think Mandy wants your cock"
He just grabs the back of my head and shoves his cock back in my mouth. He looks over at Mandy playing with her vibrator and says:
"Do you want this cock?"
She just smiled at him and nodded yes.
"Do you think you can handle it. I'm a lot bigger than your little sissy bitch here.
"Yesssss.." she says with a big grin on her face.
He gets up to join Mandy on her bed. I get off the bed and follow him to her bed and grab a condom off the nightstand. I hand him the condom and he rolls it on. Then I guide his big rock hard cock into her pussy. He slowly starts to enter her pussy and starts moving in and out. Pushing in a little deeper each time. It took a few minutes for him to get his whole cock inside her. I kissed her while he started slowly pumping her.
"Do you like his cock baby?"
"Mmmmmm.... hmmmm"
"Does he stretch you more than me?"
"Ohhhhh yessssss"
"Does it hurt"
"No... ahhh.. it feels soooo goooooood. mmmmmmm"
He chimes in with "Do you like my cock, Mandy?"
"oooooohhhh.. yess"
"Do you want me to fuck you with it?"
"Yesss"
"Tell me what you want"
"I want your dick"
"Are you ready for me to fuck you hard?"
"mmmmmm yes"
"Tell me.. tell me to fuck you"
"oh yes.. fuck me"
"Again!"
"FUCK ME! OH YES! THAT'S IT FUCK ME!"
"Does that sissy of yours fuck you like this?"
"Oh god. FUCK ME"
"Does he fuck you this good?"
"NO. ahhhhh"
"That little sissy dick can't fuck you like this can he."
"No he's too small to fuck me like this. mmmm... I love your cock. FUCK ME. PLEASE FUCK ME"
Then he pounds her really hard for a couple of minutes but she decides she wants to be on top. She rolls him over and I hold his cock while she lowers herself on him. She let out a gasp when she slid down on his cock.
She started rocking back and forth on his big dick and I know she was about to cum. I kneel behind her and start licking his balls and her asshole. In a matter of seconds she came and collapsed on his chest.

As she is laying on top of him the phone rings. He looked at the clock and said "You gotta give me a couple of minutes. I haven't cum yet."
Mandy quickly replied: "It's ok. You can stay and watch with me"
I answer the door in my panties and stockings and let in Guy 2. He walks in and sees the two of you spooning on the bed.
Guy 2: "Looks like we have an audience"
Me: Yes. Mandy has been enjoying herself and "Guy 1" is gonna stay and watch.
Guy 2: "Your a lucky guy," he says to Guy 1
Guy 1: Thank you, yes I am
Guy 2: So, what do you guys want to do
Mandy: It's my turn to watch. I wanna see Tom make you cum.
Guy 2: Ok, we'll give you a show.
I crawl on the bed and Guy 2 takes his clothes off and lies down in the middle of the bed.
Guy2: Let's get this party started.

I get between his legs and start sucking him. He's a little smaller than Guy 1 but not much. He was already semi hard when I started and it only took him a few seconds to get completely hard. I look up at him and he is staring at Mandy and Guy 1 on the other bed. Guy 1 is spooning with you and the two of you are face us and watching me suck his cock.
This image must have been too much for Guy 2 because he grabs my head and starts fucking my face really hard. He shoves his cock down my throat and I gag on it but that didnt slow him down he kept fucking my face until his cum slid down my throat.
M: Wow! Did you swallow that honey?
T: Yes
Guy 1: I told you he was a good cocksucker
Guy 2: Sorry about that I was hoping to make that last a little longer.
Me: That's ok. I'll be able to take a little break before the next guy gets here.
Guy2 gets dressed and thanks both of us and says he would like to do this again. I tell him thank you and we'll be in touch and then walk him to the door.
Mandy: That was quick
Me: That's ok with me. I'm gonna get a cigarette. Be right back.
I step outside forgetting that I'm just wearing lingerie and I still have some cum on my face. I quickly finish off a cigarette and return. Once I walk in I see the two of them kissing on the bed. I settled into my bed hoping to get another show. When I sat down, Mandy broke her kiss with him.
Mandy: Since that last guy didn't last very long Guy 1 here has agreed to give me a show. :)
Guy 1 stands beside my bed and says "Suck it sissy"
As I'm sucking him I can see Mandy behind him with a big smile on her face and her fingers playing with your pussy.
Guy 1: Alright sissy. Mandy wants to see me take your ass. Where's the lube.
She quickly jumped off the bed and handed him a bottle of lube that was sitting on the night stand. I looked at her with fear in my eyes.
Me: I think he's too big
Mandy: You'll be fine baby. You can take it
Guy 1 positions me so I'm facing Mandy and he gets behind me. I'm looking at her while he lubes my ass and starts pushing the head of his cock in my ass. I wince as he gets the first two inches in. Mandy is just staring at me with a smile on her face. He finally has the whole thing in me and he starts slowly pumping in and out. I'm moaning because of the pain. He's really stretching me. After a few minutes of this the pain subsides and it starts feeling good.
Me: Oh yeah. Fuck me now.
Guy 1: Are you ready?
Me: Yes. Fuck me!
Then he grabs my hips and starts pounding me. He pushes my head down onto the bed and pounds me. You can hear the sound of skin slapping. He slaps my ass.
Guy 1: You like that bitch?
Me: yes, fuck me yes
Guy 1: Your my bitch now. You're gonna beg for my cock
Me: Oh yes sir, please fuck my ass
The phone rings and I look up to see that Mandy is taking video of me getting fucked. I hear her tell someone our room number and then she put on a robe and ushered in Guy3.
Mandy: C'mon on in. You're just in time to join the fun
Guy 3: Oh I see that
Mandy: Go ahead he doesn't have anything in his mouth.
Guy 3: I'm in
Guy 3 dispenses of his clothes quickly and slides into bed positioning his cock inches from my face. I start sucking him and he immediately grabs my head and starts fucking my face. I thought this guy would last about as long as the last guy.
Guy 3: You've got a real slut here. He really likes cock doesn't he.
Mandy: giggles :)
Guy 1: Suck that cock sissy! Take the whole thing down your throat.
Guy 1 pushed my head all the way down on Guy 3's cock until I started to gag on it.
Guy 3: Wow this little sissy faggot really likes cock.
Guy 3 pulls his cock out of my mouth and starts slapping my face with it.
Guy 3: Tell me what you want, bitch
Me: I want your cum
Guy 3: You want me to cum in your sissy mouth?
Me: yes
Guy 3: Alright slut, get to sucking
Guy 1: Mandy, get your camera. You're gonna want a video of this little sissy faggot getting cum from both ends.
Mandy: It's already recording
In just a few seconds they both explode at both ends. and we all collapse on the bed. Just then the phone rings again.
Me: Honey if that's the next guy, I don't think I can take any more.
Mandy: Oh no, you have two more to go. Your gonna take both of them you sissy cocksucker
Guy 1: You know you love cock you little sissy faggot. Get up and get ready for some more cum.

to be continued.

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Wife cuckolds husband.I'm an always horney man, constantly thinking of sex in some form. I wonder about the type of sex every woman, I see, enjoys. That prudish old bitch everyone knows, whose ass is so tight you could stick a lump of coal in it and get a diamond out. I even imagine her with a penis in her mouth or a tongue in her pussy. That hot little thing everyone is slobbering over. Is she a hot piece of ass? Or, is she a bland fuck that leaves you wanting and needing more?Sex is always on...

Cuckold Eunuch 2

Cuckold Eunuch part 2This a story around the emancipation and emasculation of a cuckold. The journey from soft cuckolding to harsh femdom cuckolding and the further alignment of desires for both partiesPlease read the first story for context.Following my circumcision and castration Sam allowed me a period of freedom with my cock. The chastity cage that she had purchased wouldn’t fit as it needed a ball sack to grip onto - the new one just slid off.She agreed that I could go without it while...

Cuckold Stories

r/CuckoldStories, aka Reddit Cuckold Stories! Alright, let’s to a raise of hands for who knows what a cuckold is. I think we all know it, and some of us have probably even used it as a slur at some point in time. I know I’ve called more liberals cucks than I’m comfortable with admitting, but hey they had it coming. Anyway, /r/CuckoldStories is an amazing place on Reddit.com where you can read all kinds of cuckold stories. These are real stories from real people and some of them can be pretty...

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Cuckold couple Discover 102

Chapter 1 Part 2First Steps ... Sandy s side.Even if Sandy wasn’t the most sexually open girl, like everyone she still had a few kinks in her. For 4 years she had been into a long relationship with another Chinese men. They were high school lovers so it was a pretty soft loving and sexual life.After a really bad break up she was really to get over him, and it took her almost a year before she started looking at other guys.When she started collage at 20 yr old, few guys were trying to get closer...

Cuckold Striptease Game

I'd forgotten my damn key again. And my wife was taking forever to answer the door. What was she doing in there? I was mildly irritated by the time she finally opened up, but before my lips could even form the words to some smart-assed remark about how long I'd been standing there, my senses were overloaded with the sight before me. I gave her a once over -- I swear, my wife could make a pimple look sexy. If she farted while we were having dinner with the president, my first reaction would...

Cuckold Sissy

When my Filipina wife Daniella got to the U.S. I tried to hide the tattoos on my buttocks, but when she saw them, she looked at me like she wanted to vomit. When I was much younger, just after puberty, an older guy had pressured me into having them put on me. I mean, at the time I had mixed emotions: on one hand I knew that they would be permanent, and mark me as a faggot for life; but on the other I was very much sprung on this man - Jay! He was my first lover, and in fact had been the man who...

Cuckold Sessions

CuckoldSessions! All these COVID-19 lockdowns have been a real drag, huh? Some of you are bummed you can’t take your wife out to dinner, which means you ain’t getting laid. Others are pissed because the local fat girls on Tinder ain’t even an option at this point. Still, others are disappointed that strange black studs are no longer coming over on weekends to service the wife with much bigger, much blacker cocks. Well, in that case, Cuckold Sessions might be right up your alley.I’m sure you...

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Cuckold couple Discovers

Hi just wanna let you know that this is my first ever story I write and upload and english isn t my native language so please bear with me. :)Cuckold couple DiscoverChapter 1 First Steps, Marc’s SideMarc was an attractive men,5’10’ mix blood, black and white. He wasn’t so popular with girls while he was in high school thought, probably because of the social environment he was living in, and like most teenagers, he was an heavy user of porn. Nothing to freaky, but let s say he was pretty happy...

Cuckold Club Rules

“So tell me, why do you want your wife to fuck other men?”Julie and Juan looked at me expectantly. My wife Sheila were sitting in their living room, all four of us relaxing with drinks in hand, while their k**s slumbered upstairs. It was a suburban evening like any other, apart from the topic of conversation. I swallowed hard and said,“I have a small cock. I love my wife, and I realized that I can’t satisfy her by fucking her. I also realized that watching her have incredibly hot sex with...

Cuckold 3

Three years later ...John was well within his rights to ask, as it goes in the song, "Well, how did I get here?" Here was, in this sense, handcuffed stark naked to a chair in their spare room whilst his gorgeous wife was being fucked hard by her young black lover in the bedroom - their marital bedroom - next door. He looked down sadly at his fully erect willy and sighed. He simply could not control it anymore. Each creak from the bed, each groan from her lover and each lusty scream or pant from...

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Cuckold Success Strategy A Story

"So," my ther****t asked, looking up and giving me that same friendly and observant smile I'd come to associate with my complete trust in her as my cuckold ther****t, "how have you been since we last chatted?" I paused for a second to gather my thoughts and replied: "Good. I think your advice the last time I was here has really helped." (The advice she had given me had been to spend even more time than I had ready been doing watching interracial cuckold porn, and masturbating to it as I felt...

Cuckold Savours The Smelly Cumload

This is a story about a man that who feels the need to be cuckolded and convinces his wife to fulfill this need. She agrees happily with her husband’s proposal, but asks him a special favour. The husband agrees and discovers the pleasure of eating another man’s sperm. It happened while I was working away from home. I was in a hotel room masturbating and watching a porno movie when I started fantasizing about my wife. I suddenly felt the need to be cuckolded. It’s difficult to...

Cuckold Story Humilicucktrix Eating The Slops

Cuckold Story: Humilicucktrix - Eating The SlopsStory No.5WARNING: This story incorporates strong cuckold themes, including licking another man's semen from my ex-girlfriend's pussy. Please don't read if squeamish.In the past, I used to crave a bit of humiliation and would do some quite degrading things for kicks. I thought I'd compile a list of the 10 most depraved/pervy things I've done and write a short story about them each and post them on xhamster.The list:10. Drank a girl-racer's...

2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

Cuckold couple Discovers

Hello First of all I would like to say that english isn t my first language so please bear with my grammar :)And this is my first time ever to publish a story. Hope you enjoyChapter 1 First Steps, Marc’s SideMarc was an attractive men,5’10’ mix blood, black and white. He wasn’t so popular with girls while he was in high school thought, probably because of the social environment he was living in, and like most teenagers, he was an heavy user of porn. Nothing to freaky, but let s say he was...

Cuckold II

Cuckold II By PJD Judy looked at the sissy going about his housework with a sense of satisfaction; he was now a complete sissy maid. The long grey maid's dress, the white maid's cap, the white pinafore tied at the waist with the large bow, the pink bra clearly visible through his dress as it strained to contain his huge tits. Her amusement increased, at the thought that under his plain grey maid's dress, he was wearing pink nylon panties, pink suspender belt, a pink nylon...

Cuckold

Reddit Cuckold, aka r/Cuckold! Other than being the second most popular insult on online image boards, cuck is also the official word for a member of one of the weirdest fetishes I’ve ever seen in my entire life. Now, I review porn for a living, so I see a lot of wacky stuff. And since the third world porn industry is constantly trying to produce weirder, filthier smut, I’ve got my work cut out for me. But I don’t think any genre of porn is going to outdo my surprise when I first discovered the...

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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

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Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

CUCKOLD BIRTHDAY

CUCKOLD BIRTHDAYBy stitcherblue & cuckhold4pantyhoseWell if I'm going to dress you up I should do it real good. We'll start with a pair of white thigh highs with black lace appliques up the leg and a blue silk bra panty and garter set, topped with a pastel lavender silk blouse and a royal navy blue silk skirt. Well see you put the garter on then the thigh highs and then the panties over the garter that way you can take the panties off and keep the thigh highs and garters on. Silk feels...

A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

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