The Boss (Part 2)

Read Part 1 before Part 2 :).

Part 2

Trust: Initially it may be hard to believe but trust grows and flourishes in this kind of dynamic but cuckolding actually makes the trust stronger between both of your especially over time.


Before I left the office my boss gave me a few additional instructions. He wanted me to cook dinner, not my wife. He told me he wanted steak and potatoes for dinner and it should be ready by 7pm. He would arrive at 6pm. His last demand was that I made sure my wife was dressed in a sexy dress for our night. 

It was 2pm when I left. I texted my wife the news. That I was given a new job opportunity at the company and my boss was coming over to dinner tonight at 6pm to discuss it with both of us. She didn’t hold back her irritation telling me she wasn’t given enough notice and it was unfair that she would need to get the house ready and make dinner tonight for my boss. I reassured her telling her my boss didn’t want her to clean or make dinner, he wanted me to do it. I told her I had to run a quick errand and would fill her in more on the details when I got home. 

I headed to the mall and purchased my wife a new red dress for our evening with my boss. It was low cut in the front to display her perfect round double D breast. The dress was rushed and short, it would hug her perfect round ass showing off her beautiful curves. My wife’s blond hair and blue eyes always looked hot in red. I have forever enjoyed shopping for my wife and there was an extra thrill today knowing I was dressing her to impress my boss. I decided to also head to Victoria Secrets to purchase her a red thong and matching bra. Sales women always smile when I shop for my wife, I guess not many guys know their wives exact sizes. It is funny though I have always been more of the girl in our relationship when it comes to shopping, loving getting her all the newest styles. I knew this outfit would fit perfectly with a pair of black heels that I purchased her for her last birthday. 

When I arrived home I was nervous but for some reason excited. I was conflicted and felt guilty for what I had done this afternoon with my boss. How was she going to react that I gave him the green light to seduce her at our home? What else was he going to make me do? How about the fact that I sucked his cock?

“What is all of this!” my wife asked. 

“Well Andrew, my boss had some requests for dinner tonight.”  

“Okay, but what is all of this, looks like you went on a shopping spree!” 

“Andrew asked me to have you dress sexy tonight. So I purchased you a new dress…. And while I was at it I decided to get you new lingerie. He also asked that I make steak and potatoes for dinner so I picked that up too.” 

“What the fuck! Your boss asked you to purchase me lingerie!!” 

“No, no baby, he didn’t ask me to purchase you anything he just asked if you could wear a sexy dress like you did to the last company party. It was my idea to buy you a new outfit, I know how much you like new dresses.” 

She held up the dress, I could tell she loved it, it is just her style. She smiled at me confused but willing to play along. 

“Okay, you want him to see me in this at our home? What kind of message do you think that will be sending? You already know he is attracted to me. Fuck he flirts unabashed with me at every company party in front of you and your coworkers. Last company party in that dress I had on he couldn’t keep his hand off me!”

“I know, but you kind of like the attention from him don’t you? I just want to do what he told me to do tonight, can you help me and play along just for tonight? He is my boss.” 

With a smile she looked at me in the eyes. “This all just seems strange. You text me this afternoon to tell me your boss is coming over to discuss your new role at the company then you come home with all of this. What the fuck happened today?!” 

I’m back, shy, eyes down, ashamed of what is happening but I can’t help my desires to see it through, to do as he says. “Honey it was kind of a fucked up day, there is going to be big changes in my life at work and possibly at home because of it. I promise you will learn all the details, but I also promised Andrew I would let him tell you. If you don’t want to wear the dress you can wear whatever you want, you look beautiful in anything you wear. I just wanted to please him tonight with this request and thought you wouldn’t mind getting a new dress either.” 

“Okay, I will wear the dress and even the lingerie but I feel I am wearing it more for him than you so don’t get mad when your boss reacts like a man to a woman wearing a dress like this for him! You better know what your getting yourself into! I am going to go shower and get ready, I guess you will be down here getting the house ready and making dinner. You said he will be here at 6?”

“Yes….. and thank you for doing this for me.” 

It was 6pm when my boss knocked on the door, right on time. I had the house straightened up and started dinner so it would be ready at 7 as requested. My wife was not ready so I got us both a beer and we sat in the living room. We made awkward small talk and he told me not to worry about a thing, that he would take the lead tonight and I was there just to serve the two of them. He made it feel like no big deal. I couldn’t believe I was okay with this, he had me in the palm of his hand, the crotch of his pants. 

When she made her entrance she was stunning!!! She went all out and had the captured attention of both of us. Her hair was styled, curled down her shoulder with blond locks. She had done her makeup in deep shades, with smoky eyes and red lipstick to match.  The red dress hugged her every curve like I had imagined it would. The front of the dress plunged down displaying the perfect shapes of her breasts. The ruching of the dress gathered just below her ass showing off her lean fit legs. She looked like a model, a goddess. She looked like she was going out on the town to get every males attention, yet she was staying at home with her husband and his boss. 

Andrew stood and stared at her up and down. She met his eyes and quickly gazed down in guilt of allowing another man to look at her that sexually. He approached her, giving her a hug and a kiss on the cheeks. 

“You look more beautiful than ever Elizabeth! Did Josie purchase you this dress?” 

The name seemed to go over her head, she just giggled and said “yes he did, he said you wanted me to dress sexy tonight and this is what he got me.” 

“Wonderful! I couldn’t have picked out a better dress for you.” Andrew said looking at me. “Come sit next to me. We have a long night ahead of us if that is okay with you Elizabeth.” 

My wife like me seemed in the palm of his hand. They sat on the couch with me on the other side of them. Andrew placed his right hand on my wife’s leg and started to caress it. She looked at me waiting for me to stop him. All I could do is give her an approving smile. 

“So Elizabeth, I am not going to waste any time as we have dinner that your husband will have ready in an hour. I have a lot to tell you about your husbands and my day at work but we will get to that in a little bit. Do you remember when we were at the company party and I told you how much I loved your dress you had on that night?”. 

She smiled and looked at me then him “yes I remember you were quite excited with me in it.” 

“And you remember how I just couldn’t keep my hands off of you? You looked so hot in that dress and you told me your husband got it for you. Just like the dress you are wearing tonight.” 

“Yes I remember it all too well.” My wife said. 

“It seemed you liked when I flirted with you and you enjoyed how I touched you. Like I am doing right now feeling your legs. I recall seeing your husband watching us and not doing anything about it. You didn’t stop me from touching you that night. You didn’t stop me from openly flirting with you in font of your husband’s co-workers. In fact you encouraged it by flirting back with me, pushing your body and your breast against me.”

My wife was breathing hard as Andrew moved his hands up her body lightly touching her breast. She looked at me wondering if I was going to stop it. 

“Do you remember when I danced with you, how I pulled your hips into mine, how I rubbed my hands on your ass as you pushed into my hard body.” 

“Yes, I remember Andrew.” 

“When you and I walked out back away from the crowd.” His right hand was now lightly on her face. “Did you ever tell your husband I kissed you Elizabeth?” 

She took a deep breath “No.” 

“Did you like when I kissed you Elizabeth?.”

Looking at me I could see she was turned on by my boss I could see the desire. She was feeling sexually empowered by this man.  

“Did you like when I kissed you Elizabeth?.”

“Yes! I did.” 

It was then he kissed her gently and soft. Lips to lips they shared a kiss in front of me. 

He looked at me. “This is not the first time you have seen me kiss your wife is it? You see Elizabeth I saw Josie watching us as we kissed at the party. He didn’t do anything like he is doing nothing now. You felt guilt when you broke off our kiss and ran away. Your husband though was turned on, like he is right now. I bet you two had sex after the party, I bet you both thought about us kissing as you two fucked with more passion.” 

“Is that true! Did you watch me kiss your boss at the company party and say nothing! What the fuck why would you do that? What is wrong with you?” She was still leaning close to him, his hands on her body as she confronted me. 

Andrew grabbed her again and fueled with passion they kissed again. Their mouths opened allowing their tongues to meet each other as the two sensually kissed in front of me. It was so taboo the sight of my wife wrapped in an embrace with another man, the two of them right across from me. I briefly felt a sharp pang of jealousy, but it was quickly overcame with the erotic thrill and sexual turn on of seeing what was unfolding in front of me – my wife with my boss. His hands were all over her now, groping her breasts.

When the kiss broke I could see the passion in her eyes, she wanted this man, she wants to fuck him. 

“You see Elizabeth I know something about your husband that you are about to learn he is a sissy girl. A submissive, now my submissive. He will do anything I want him to. I assure you that he loves you and after tonight will be a better husband than he has ever been. Like tonight buying you clothes to wear for real men and cooking and taking care of the house while you get pleasure you haven’t felt for years. Isn’t that right Josie?”

My head was spinning. My automatic response was “Yes sir.”

“You see, your husband has sexual needs. He is a cuckold, a submissive. He needs to feel like he is feeling right now. He wants you to be happy and for you both to have sexual excitement. He also knows you have needs, you need a man sexually like me Elizebeth.”

“Elizabeth if you want more, I want you to take me to your master bedroom. Do you want more Elizabeth?”

“Yes Andrew I want more! I don’t fully understand this but clearly this is what all three of us want.”

“It is Elizabeth but first let me show you your husband’s new role with me. Josie come over here and get on your hands and knees like you did at the office today. Take out my cock and show your wife what she will be fucking tonight.” 

My wife stared through me, eyes locked. Was this turning her on or was she disgusted over me?. I did as boss asked and kneeled in front of them. I placed my hands on his knees and unzipped his pants. His cock was already hard as I pulled it out. It was almost double the size of mine and twice as thick too. She couldn’t keep her eyes off of it. 

“Does your husband have a cock like this?” 

Gasping she answered “not even close” 

She now had her hands on it, stroking it, drawn to it. “Do you want to see your husband get it ready for your pussy Elizebeth?” 

“Fuck! Will he? Yes.” 

“Suck me ready for your wife Josie.” 

I placed my hand with hers on his cock. In my hand, it is so impressive so much larger than mine. It felt so wrong rubbing his cock in front of my wife but so right. I wanted to please him to take as much of his cock in my mouth as I could. I started to bob my head up and down getting more and more in as he talked to my wife “see Josie is a little cocksucker Elizabeth. He sucked my cock at the office today, he agreed to give you to me sexually. Are you okay with that?

He was now fingering her as I sucked his cock “fuck yes, If that is what he wants!” 

“Is Josie really a he though?” Andrew said with a laugh. 

“Well is what she wants” Elizabeth giggled.

“Now pull it out slowly.” “Oh yeah, you are the perfect little slut, you can take it all”. “You were born to suck cock like this to worship the cocks that will fuck your wife.” His dirty talk had my little clit penis dripping.

“Elizabeth, Josie is going to serve both of us here at your home and at the office. Today Josie got demoted although I think we can all look at it more as a promotion. Josie here will show up at work tomorrow, after I have fucked you all night. He will have a new position. He is going to be my secretary. He will have a desk right outside my office and do anything I tell her to do, isn’t that right Josie?”

“Yes sir!” 

Andrew was now done with me, he pulled me off his cock and pulled my wife up off the couch into his arms. Grasping her ass with both his hands he kissed her passionately. Pulling off her panties off, he handed them to me. 

“Josie, put these on and go finish making dinner. I’m taking your wife to the bedroom to show her her new position in this home.” 

As I made dinner, her thong pushed up splitting my ass crack, covering my little penis fully. Most men would spill out of panties like these, but not me her panties fit. It would take some time but I would become proud to have such a small penis to experience nights like this. 

Off in the distance sounds echoes filled the house. My wife being fucked by my boss. I knew this was not going to be the only night she would be fucking this man. I imagined them fucking in his office while I did secretary duties just outside. I imagined watching him fuck her in our bedroom.

My wife was learning quickly she loves big cock and Andrew was teaching her this. She had a dreamy look in her face as she floated to the bedroom with him. I heard her scream many times before dinner “Oh fuck! You feel so good!” She orgasmed over and over “Fuck, yes, I need it in my pussy, I need to feel you fuck me, I’ve wanted you to fuck me sense I first laid eyes on you.” She didn’t hold back with this man, she knew what she wanted and she was going to get it. Why would she hold back? After all her own husband sucked this man’s cock. I heard him slap her ass and then “AAAAAAAHHHHHH WOW! They sounded like animals as they passionately fucked. I could hear him piston in and out of her pussy. I could visualize what it looked like, his cock thrusting in and out of her stretching her pussy fucking her so much deeper in places I could never reach.

Andrew grunted and told her “take my big thick cock”, “you are one sexy slut”, “you love my big thick cock?”

She was not thinking about me, she was being fucked and loving every second of it as she yelled back at him  “I love your big cock”, “you are fucking amazing” “I can’t get enough of you, I love everything about you”. 

With her encouragement Andrew returned “you’re going to fuck my cock all the time after tonight”, “you can’t get enough of my cock, you’re a good little slut and are going to have more of it”, “Are you going to be a good slut and fuck my cock all the time.”

With a deep scream  “I’ll fuck you whenever you want”, “your cock owns me now”, “I can never get enough of your cock”, “I fucking love your cock!” “your cock owns me!” Her words rang to the back of my head. 

As much as it hurt to hear her tell another male that he owned her pussy, I also love it and it turns me on thinking about her fucking him whenever he wants to, as many times as he wants. Him showing up at our door to ravish her. He is an alpha male, his cock is huge, she loves it, and this day was surreal and perfect. With this thought I felt immense pleasure hearing my wife being fucked by him. Hearing so much pleasure from her. Thinking about my new position in life. 

“Ohhhhh, fuck, you are hot Elizabeth!!! I am going to fuck you all the time!” Was the last thing I heard as he filled her stream after stream filling my well fucked wife with his cum. 

They came down shortly after giggling and laughing, hugging and kissing each other. Ready to eat the meal I prepared. They sat next to each other and couldn’t keep their hands off each other. Andrew looked at me, with a laugh he told me he was taking care of making a creampie dessert after dinner for me. 

We talked and Elizebeth said “so my submissive husband or should I call you my wife this is everything you want?” She was giddy. I smiled and told her “yes”.  “And you are going to lick my pussy when he is done fucking me, lick my pussy whenever I tell you to? “yes”. I answered.

She screamed in excitement “This is so fucking unbelievable, I love it!”

My wife now has a boyfriend and I have a master. It turns out it was a turn-on her watching me suck my bosses cock and she thought it was extra hot when he had me put her panties on. She told me they were a perfect fit for her cocksucker.

After that day my feminization was accelerated. I was Josie at the office and at home. It was no secret Andrew was fucking my wife and everyone at the office knew it. He held true to his word and had me suck his cock during the day often. He told me he would fuck me when he felt I truly deserved it but in the meantime it was my wife’s duty to train me and help feminize me. It was extra embarrassing and arousing when she would call the office to talk with him having me pick up the call as his secretary. The most humiliating night was when he took her as his date to the company party and had me serve drinks.

My wife has fucked some of the other company heads with Andrew. It is always a pleasure when I am allowed to watch her cuckold me and serve the men and her during the experience, as well as cleaning her pussy at the end.

I am often ask if my wife and I still have sex? We are more in love than ever, we are best friends and lovers. We often have sex like two girls. Lots of kissing, rubbing our bodies and clits together and using toys. We can both orgasm very intensely just from this type of play without me penetrating her. She cums harder from bigger cock and I cum harder like a girl. We don’t need my cock for sexual satisfaction but she still takes me inside of her, and I feel very loved every-time she does.

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