One Sissy's Night Ch. 02

Story Info
Continuation of a sissy boy's night out.
2.3k words
4.36
48.2k
19

Part 2 of the 2 part series

Updated 10/19/2022
Created 10/10/2014
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While my date sat back and relaxed with a drink while the limo continued down the freeway, I smiled that I was able to please him. It made me feel so good that I was able to make him cum so much. Here I am, this man's man by day, a man that runs a company that employs over a thousand people, dressed as a slutty MILF in a limo with a stomach full of a black man's cum! I was loving every minute of it, I felt as if I was right where I should be! I sat in the limo sipping champagne gaining confidence with each passing mile. I believed he forgot I was a man. I felt so great as we pulled up to the restaurant. It was a new place that was designed for the new rich, swanky, dark, sexy, with strong drinks and light food. Perfect for a sexy lady and her handsome date. I was treated as a woman should be treated, men helped me out of the car, they opened doors for me, they pulled out my chair, I was feeling on cloud nine when we sat down.

While we were being seated, I look around at the table next to us is you! You are seated with my wife and several of my Sr. staff/friends. OMG, My stomach sank, how could you do this? The night of my life and you are here to humiliate me! I can't run out and to make matters worse you are paying for their expensive dinner with my credit card! As I notice this my date moves next to me and whispers in my ear; he asks me if I like his choice of restaurants, he loves the clientele here! He then tells me what a sexy sissy I am and he has several surprises for me tonight as he stares at the table next to us. I am humiliated... As I feel my face turning red I can't help but notice my cock is rock hard in my panties. I can feel my precum soaking the lace... Oh god I'm so flustered when only a few seconds ago I was so confident! Do they notice it's me? What will my wife say?

While these thoughts are running through my mind, he moves his hand up my thigh highs... Slowly... Finally his strong hand reaches the lace covered, dripping clit between my legs. He feels how hard I am. He feels how soaked the front of my panties are. He tells me I deserve the humiliation I am getting and my wife deserves to have fun with the real men I employ. I'm speechless but ungodly horny.

He grabs my hand and He places it on his cock. He then uses his fingers and turns my chin so we are staring eye to eye, leaning in, he kisses me. It is a strong but gentle kiss on the lips and I melt. I melt into his arms and am a blur in the sexiness of the moment. This is truly a man! I am his sissy. I gently rub my hands on the front of his pants, I can feel his cock stiffening and I lose myself... I don't care who is in the table next to me... I want him! I want nothing more than to be this man's lover, as I go to unzip his pants and let him out again, but he stops me. Not now, he says, we have people joining us.

Turns out my date knows several of my employees, as you take my wife into the club for drinks and dancing my date invited my table of employees to join us. I'm so scared I can't talk! I can only look at the table and nod when they all talk to me. Amazingly they don't seem to notice who I am. The drinks and shots start flowing and as I feel more comfortable that they do not realize it's me, I come out of my shell. I chat with them and I'm amazed, they are all over me. Someone is groping me at all times, at first I tried to push them off, but I though who was I kidding I wanted this! I was so hard and dripping my body was telling me what it wanted!

They have no clue it's me, I kept thinking. This roller coaster of emotions had me on a high again as I excused myself to use the rest room. Walking past the club, I can see you and the wife doing shots and talking to guys at the bar. I can't believe my wife, she is having the time of her life! She is laughing flirting and letting these men have their hands all over her! She is falling out of her dress, she looks incredible , who am I kidding id be all over her too! I just can't let her see me!

Later, after the 5th round of drinks they all invite me to dance, one by one I dance with them. All of the men, they all take turns dancing with me, they all are kissing me, grabbing my ass, they make me feel like such a sexy woman... While on the floor I can see my wife with several men. She is all over them! I can't believe she is doing this, I would be so humiliated if I saw this as a man, right now I'm a woman and doing the exact same thing. I can only hope she's having fun and being safe! At this point I don't care what she does anymore, frankly, I'd like to be doing several of the men she's flirting with. I can't blame her! Im a drunk, very horny mess and ecstatic when my date tells me it's time to go.

When we leave I find myself being escorted by my date as well as all my employees. It looks like we are now a group and they all join my date and I in the limo, headed back to the suite. When I get in the car, after all this attention and drinks I feel as if I am ready for anything. Im the last one to get in and as I settle into my seat I can see they all have their cocks out ready for me. I'm in heaven!

With a big smile on my face I go One at a time around the limo. I take each of them, Licking and sucking one man as I'm using my hands on another. While I'm doing that, they have their hands all over me, up my dress. On my drenched panties. Grabbing my clit! One man's hands are forcing my head up and down my employees cock while I'm stoking the others... In the middle of all of this I hear someone say "what an amazing boss"... They know it's me! Omg!

I stop. I look at them all and in their eyes I can tell they all know! I'm panicked, here I am in a dress I just had each of their cocks in my mouth what can I do??? I give in. There is. Itching to do! I realize I just want their cum.

Breaking the ice, My date orders me to swallow all of them. He also tells me not to forget I need to make a good impression in the lobby so I need no messes on me or them. I don't care I am drunk, dressed like a slut, with four hot men in a limo. I do what feels right I dive my mouth on one man's cock!

My date is chiding me, telling me how sexy I look... Tells me how a good girl loves cum. Once he said cum the first guy, my IT guy, loses it in my mouth. Oh god I wasn't expecting this much from him. He Is such a geek, but my god he has a long skinny cock with a lot of cum. I take it all, but barely... I don't have time to think about it as Jon in accounting forces his cock in my mouth. While I'm sucking him he tells me he always knew I liked cock and he's going to give it to me. I looked up in his eyes as I sucked him. I took him out of my mouth and told him I'm a good sissy that wants his cum and please let me eat his seed. Two more long sucks and I got my wish! I'm out of control at this point. I can feel my excitement rising, I want to cum too. My date must sense this as I'm sucking on Jacob in the sales group. He grabs my cock and squeezes hard. Slapping my balls he tells me I will not be cumming tonight. Only pleasing. The extreme pin brings tears to my eyes as Jacob gives me his load.

A few miles later we pull to the front of the Ritz, the men give me a minute to fix my makeup, touch up my hair and get out. My date escorts me in, telling me how humiliating that must have been but he was proud of me. Just to hear those words made me erect. I will do whatever he asks to make him proud! He tells me I look beautiful and every man there wanted me. All the other women were jealous.

When we get to the suite there is a party already in progress are four other of my senior staff there! It's obvious they know what is going on and they all whistle as I walk in. There is. Itching I can do at this point then to just go with it! With the four men I've already sucked I feel very slutty. I can't wait to take the other four, however they have other plans for me. My date takes me to the bed room, rip off my dress, laughing at me they calls a sissy and tell me how they are going to use me all night. I am a combination of horny, excited and scared. As my date kisses me on the lips and rubs his strong black hand against my cock he tells me to be a good slut and he will reward me. Later.

With that he leaves and three new men enter the room. To say they were aggressive was an understatement. One boy strangled my neck forcing his cock in my mouth while the others took turns taking me anally. It felt so good to be a tool to these boys pleasure. I felt like nothing but a toy to them. I started to love it. My fear turned to wild excitement, I found myself begging for their cocks. I wanted them cumming in my mouth, my ass. My hair! I couldn't get enough! As one came another on entered the room. I was in heaven! They put a dog collar on me and a chain from the collar to the bed so I couldn't run. They didn't need to restrain me, I wanted this.

While I was every taking each of them, I could hear moaning in the other rooms, it sounded like there were other women out there. It was awesome hearing other ladies having as much sexual joy as I was having. The night started to blur... Man after man was using me. I had cum in my mouth my ass my hair. I was a sweaty sticky mess. I would not stop though. I wanted to please every man there.

I never came once that evening, I leaked precum all night but was refused the right to orgasm. As the sun was coming through the blinds and the last man came in my mouth, I saw my date. Funny, he never came in to use me. He walked over to me, unchained me and took my collar off. I was exhausted, he looked at me and told me I made him very happy. He kissed me deeply and looked me in the eyes. I almost felt in love with this strong black handsome man. He told he he had one more surprise for me and they I will get cleaned up and could rest.

I looked over his shoulder and saw you, escorting my wife into the bedroom. She looked like me. Used! You spoke up telling me she took all of those men as well. It was her, and you I heard cumming! She was a great toy for my employees and date. You were happy to tell me she took him several times. She took him bareback! She was insatiable in the amount of cock she wanted. We were almost the same woman.

My date told me to lie down as I lay on my back he tells me my final surprise is to clean her pussy. Then you will shower her and take her home. As I layed back on the bed she walked toward me, she looked gorgeous covered in cum. She was a hot mess but gorgeous. She leaned over to my ear, told me she loved me but she stopped taking the pill months ago and from now on only my date can use her pussy. With that she straddled my face making me eat my dates cum out of her pussy. The sensation was incredible! I couldn't control myself anymore! I came in a strong orgasm all over my belly. No one touched me.

When she left I could see you two kissing and you helping her shower. My date sat back and laughed at me. I started to cry, tears of humiliation and of joy. This was the greatest night of my life.

The end.

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10 Comments
cdCindy1cdCindy1over 4 years ago
second comment

Love this story so so so much. My other comment said in more detail my current situation and how much I love this story. I truly want my wife to get fucked in front of me and I truly want to have her watch while I suck cock and get fucked. I also want her to know that I'm a sissy cross-dressing faggot -- she needs to know the truth. Please wish me luck in coming out to my wife. In the meantime, please tell us more stories. This is one of the best of all of Literotica.

garter2000garter2000over 5 years ago
Love sissy’s in chasitity

Incredible... please post more

cdCindy1cdCindy1almost 7 years ago
please continue

Please tell us more. Please continue this sexual adventure of a sissy husband who has a slutty wife. I too am a sissy husband and I truly wish my wife knew about my CD adventures. It would be so hot to go out to dinner with my male lover and have my wife, our friends and our co-workers at the next table. I know they would all call me a "sissy", a "faggot" and a "cum-swallowing cock-sucker". Yes, I am all that -- and more. I would love to have my co-workers see me dressed up and use me like you got used by your employees. Maybe I'll circulate this story throughout the company and see what happens. Wish me luck !!!

AnonymousAnonymousover 9 years ago
What if this unnamed

It would be hot in that chapter to see the man's man (The name is not known to me) be with the cuckhold (Since I do not know his name) and his wife. He can turn the cuckhold into his girl as well as be with his wife to show both of them off. Breast Implants for both of them and hormones and blonde hair for the cuckold.

CSKCSKover 9 years ago
Offer to be an Editor

Hey, I, just like you, started out a bit rough with writing and one of the things I have found that helps is the use of an editor. Someone to help you look out for spelling and language issues, questions the reader might have and structure. If you would like some help, I would be more than willing to do that. A lot of people on here take the low road and just anonymously bash and that can definitely deter someone from trying to improve. If you are interested, my contact info is in my profile.

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