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Cuckold Sissy Pimped Out

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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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