I met Terri and we started dating . I'm 21 and she's 20 , we met at work . I'm a sophomore in college, and I got an apartment off campus . She hangs out there all the time . One night she asked if we could do a Halloween costume party, I agreed .
She told me she wanted us to dress as a prostitute and pimp . I said ok , thinking I was going to be the pimp . She said no you're going to be the prostitute and I'm gonna be the pimp. I agreed thinking I was going to be a male prostitute.
We go out to the mall shopping , she hands me a pair of 4in pumps and said try them on . What for ? Your the prostitute and need to dress like one I replied a Mail prostitute, right
No, she answers you're gonna dress up as a female prostitute. She looked around and rubbed my cock and said please for me . I said , ok
I tried them on , they fit well but almost broke my ankle . She laughed at me . We then stop at a sex shop , she buys garter and thigh high hose . We had back to my place and head in , she said put this on and your heels . I did , and my cock got rock hard . She laughed and said see you like it , I walked around the apartment in my heels and hose .
Terri says you need to get use to them and wear them around the apartment when I'm home . She grabs my hand and we a great fuck session.
Terri leaves and I put my hose and heels on and walked around in them to get use to them . I started doing it everyday , and was more confident in walking in them .
Terri comes over later in the week , with a bag . She gets a black lacy g string and short skirt out . And says try this on . I took them and tried them . She looks and says we're about the same size . I would be considered a twink . I'm 5'7" about 120 lbs , terri is a little taller than me . I come out in dress and panties on . She looks me over and says it fits well expect I was rock hard again .
We need to do something about that , she laughed . Terri grabs her phone , and googled something. Lets go , we goto sex shop and she buys a cock cage . We get home and we put on my cock cage and put my prostitute cloths on and this time no hard on .
Our party is next weekend , people we work with , people we goto school with , and a few neighbors.
Terri come by Thursday, we go shopping for food and alcohol. We put everything away and runs a bath . Get in she tells me I did , I though it was going to be a hot sex session again . It wasn't she handed me a razor and tells me to shave my legs and body . I did as I was told . She comes back in and said you need to shave your butt and cock also . She grabbed the razor and helped me . . Look at you , she laughed your all smooth . I smiled . We go into bed and she sucks my smooth cock . It was kinda different this time , she was blowing me and I felt her put a finger in my ass . I got excited and blow my load quickly.
She gets dressed and said I will be here Saturday afternoon before the party . Saturday comes and we go out for last minute things , she pulls into a nail salon . Terri said let's go , we go in and she gets us manicure and pedicure . She picks out this bright red nail polish for my toes.. and buys a bottle to take home . .
We get home and she said go shave yourself again . I did as I was told . I get done and walk out and she's at the table , she put fake nails and paints my finger nails the matching color of my toes .
She grabs my cage and puts it on me . And she puts make up on me and bright red lipstick. When she was done she said go get dressed. Terri hands me a shirt that shelve-less and a piece to cover my neck .
I come out in room , totally dressed heels hose and all . She pulls a wig out and puts it on me .
Damn you look hot , I looked in the mirror and couldn't believe how I looked . She goes in and push her Hollywood Madame outfit on comes back out looks at me and says everybody should be getting here within the next hour or so
About an hour later, the first knock at the door, it was John the next-door neighbor. He was dressed up as a cop. I opened the door his jaw hit floor and asked Terry and I were. I laughed. I said it's me. He said holy shit . This process went on for over the next hour. People couldn't believe my outfit..
As a party went on and people began drinking. I kept getting looks from some of the guys and even had one asked me how much and laughed. I said you need to talk to my madam, and laughed back..
I look over Terri and she's talking to John and looking over at me and he walks to the back of the apartment by this time, I was a little tipsy I've been drinking for a few hours and she said I have your first customer I said what are you talking about? John just gave me 50 bucks for you.
For what I ask, you're gonna blow him remember you're a prostitute. I'm not doing that. She smacks me if you are you sissy you're gonna do what I tell you to do or I'm gonna smack you again now get your ass back there now.
I walk back John sitting on the edge of the bed pants down to the floor cock out, rock hard and looks at me. What do you think? He says? I hesitated and said looks good.
He said we'll get over here get on your knees and take my cock in your mouth. I pay good money for that mouth. He stands up. I get down on my knees smacks the side of my face with this cock that you need to open your mouth I did as I was told, and I slid his cock in my mouth. Mmmmmmm that's a good little slut now suck my cock. I've had my cock suck before so I know how I liked it so I started performing what I like on him.
As I did, I heard the door open it was terri coming in to check on me. She laughed and said I knew you were gonna be a cock slut you little sissy.. John started speeding up and fucking my mouth. He started to tense up and I knew he was getting ready to blow his load he came in my mouth. I turned to spit it out and Terri said no you swallow that and smack me again. I did as I was told, and I cleaned John's cock off with the rest of his cum on it..
He zipped up, walked out of the room and said that was a good little slut that you have.
Terri looks at me so come on let's redo your make up. We need to drum up some more work for you now. We went into the bathroom she redid my make up. We go back out in the living room where the party is going on. I see John talking to a couple guys they all looked at me and smiled.
Next thing I know Joe and Mark are talking to Terri , she signals over to me to go back to the bedroom. I'm sitting on the edge of the bed and Joe and Mark walk-in.. Terri right behind them and said OK. I have some work for you to do..
The time it's gonna be a little different, you're service there, cocks . And you're gonna get fucked.. no I said she smacks across her face again I told you you little sissy you will do as I tell you or else
So Joe and Mark stand beside me, it tells me to get on my knees. They both whipped their cocks out. They were eight or 9 inches each at least.. I start working on Mark's cock and stroke in Joe's. Terri laughs and said I'll be back in a minute as I was sitting there, sucking their cocks. She comes back in and says get up I did as I was told. She unzipped my skirt pulls down my G string tells me to bend over I felt the coldness of the lube. She was rubbing across my ass this excited me..
She changed to Joe and Mark and says my sissy slut ass is ready for you . Mark didn't have to be told twice he jumped and bent me over to bed it was hot. I still have my heels on, and this guy is getting ready to fuck my ass.
Mark work this cock into my ass ass slowly , Joe gets on the bed in front of me. Terri , leaves the room and says my sissy slut has his under control. Mark slowly pushes his cock in and out of my ass. It hurts, but it felt good.. I grabbed Joe's cock and was sucking on it while Mark was fucking my ass. Mark started getting faster and faster. I felt his balls slapping up against my ass. I was deep throat and Joe licking up and down the shaft, licking his head and push him back as Mark pushed his cock into me. It was so fucking hot.
Mark grab my hips. It was pounded me. He announced that he was fucking cuming . I felt his cum shoot into my ass. He was breathing heavy, climbed on the bed and Joe took over for Mark and fucking my ass . After about 10 to 15 minutes, Joe dropped his load into my ass.. they got up got dressed and they threw $150 on the bed and said that was great. And walk out the room.
Terri , comes back in collect the money off the bed tells me to go in and clean myself up. I'm a mess we go back in the bathroom. She touches up my makeup. She helped me put my skirt back on .
So we go back out in the living room people are looking me and giggling. She handed me a glass of wine and said sluts like you drink wine. So I drink my wine lipstick on the glass people looking at me. I was talking to friends and some of the women in there. Next thing I know I felt a hand rub it on my ass. I turn around it was Bill.
Bill is my coworker and I was a little afraid that he was gonna tell everybody at work what I was doing. He walks over to Terri , and Terri walks over to me and says Bill's gonna tell your Work if you don't suck his cock. I figured as much.. with that I started headed back to the bedroom . Not in the bedroom he wants it here he wants you to suck his cock with everybody watching..
I took a sip of my wine, put my head down and said OK. With that I walk over to him I squat down didn't get on my knees. I was squatting in front of them. I unzipped his pants. He had a 6 inch cock. I pulled it out and I start working on it.. I hear some of the guys and girls going. Oh my God I can't believe this. Terri said yes this is my sissy slut . She does guys and girls if anybody's interested.. I work Bill's cock until he exploded in my mouth, sucking every drop making sure I didn't disappoint my madam. He zipped up and said that was great thank you.
More to cum
14 comments
Fucking AWESOME!!!

Oh, yes, can't wait to hear more!!!!!!!!!!!!
Wow, that's wild, his gf turned him out
Wow she really did pimp you out
Really a great story about how you were trained to be a sissy to a dominant woman. That’s about the way my mistress trained me. Samantha a very passable Gurl
Very hot sounds like you liked sucking and swallowing, yjen to get fucked like that, you became a real slut and now you like getting fucked and sucking cock, you sucked at least four loads, did they all taste good, and did you continue after the party you need to tell us more.
I would love to be a slut like that for a party, so hot
Me, too!!!!!!!!!
Sounds like you could use some help, i`m available
Interesting arrangement for Halloween and sound like your ready for plenty more cum.
Nice story . I love that feeling of a cock throbbing as it swells and pulses deep in your asspussy when he cums !
Sounds and looks like you got a big cock for your pimp was good and did you want more of those cocks.
This was a fantasy come true for the one guy who got to be a sissy for several men that night. From the first chance he got to be a sissy slut he went for it. So exciting. I wonder how many men would go for it if the next day no one remembered it was them. More than you think is my guess
Interesting
Was a different story than I usually read but read it anyway
would like to hear more great story