Cuckold Coworker

This is a true story so it may not be as exciting as a made up one but it happened and it will be written in two parts. Part 1, written here, is how it started so there is a lot of build up. There is humiliation to the husband so if you will be offended please do not read. I will eventually write part 2 about how the cuckold coworker was allowed to watch me fuck his wife. It is also proof that you can have a normal sized dick and still dominate a couple.

Tom and I worked the overnight shift together for 15 years. For those of you who have not worked overnights, there is a camaraderie that develops among employees. There is a lot of downtime on night shifts. When you're living a normal life and you have personal problems there are distractions all day long. However, at a night job, there is only your job and it can be lonely, so you talk to your coworkers more. Tom and I were no different. I knew about his first marriage troubles and how, after they separated, he lived in their basement and had to listen to his wife get fucked by other men. I knew he was into porn where women were humiliated and that his parents raised him all screwed up.

I liked his second wife. She was nice to me and good looking in a girl next door way. She always wore baggy clothes so I thought she was hiding either big tits or a fat stomach. I didn't have as many personal issues as Tom so he knew less about me but he did know I was a huge pervert.

After 15 years of night shifts and the end of my marriage, I decided to go back to the normal daytime world but, because of those strong bonds, I kept in touch with about five former coworkers.

About five years after I left the company, my phone started ringing off the hook from multiple former coworkers. I answered one of the calls. Did you hear about Tom? He was drunk at happy hour and told Joe he didn't want to go home. When Joe asked why, Tom started to cry. He said his wife fucks other men and he wants her to stop but she won't and when he gets home tonight, she has a date to go to.

I felt bad for Tom but it all started to make sense. I realized he had been lying to me. He wasn't watching female submissive porn. He was the submissive. I was now convinced he got off on his ex fucking guys why he listened in the basement. It just kind of all made sense and I got pissed. I spent a lot of nights over many years talking through his issues and feeling bad for him but he was hiding the real truths.

I had already moved south to a great beach community so there wasn't much I could do about it since I was a plane ride away now. I did stalk his wife's Facebook though. I just couldn't wrap my mind around looking at them in family photos knowing she was fucking around and he originally condoned it but now wanted it to stop and she wouldn't. While looking at those photos I decided I was going to fuck her too because Tom lied to me for so long.

Since I knew Tom often worked weekends I text someone from the company asking if he was working. He was, so I went back to Facebook and sent his wife Jen a DM asking if I could talk to her. She immediately answered yes. I called her and did the usual pleasantries. I don't know why I thought this was a good idea but I just said it.

"Jen, something happened a few weeks ago and I want to tell you. I am not judging you at all. Apparently, Tom told someone at work that you see other men and I have always found you attractive so if it is true, I want to be one of them. I have also known Tom a long time and know what makes him tick. If he knew it was me with you he would go crazy but in the way he needs it." I stopped talking and waited.

"Are you fucking kidding me? His coworkers know?"

"Yes, are you surprised? The whole thing was probably his idea and now he's blaming you."

"Do you know how many times he asked me to do this before I agreed. Years."

"Listen, I know how fucked up Tom is. I also know there's something deep inside him from his childhood that wants to be humiliated and I have a plan to satisfy his needs, your needs and definitely mine. Want to hear it?"

"I don't know. My head is spinning. Let me think about it, ok?"

"Of course. Please keep it a secret for now that I called you."

We hung up and I wasn't sure what would happen but Jen called two hours later.

"Hi, I just finished a bottle of wine and now I'm drunk, angry, annoyed and I want to teach that little fuck a lesson. Let's hear the plan."

I told her the plan and some of my ideas for rules. She loved the idea of Tom paying her airfare to spend the weekend fucking another guy. I wanted to make sure she understood what was going to happen so I told her several times I would sexually abuse her the entire weekend and we would tell him everything as it happened. No secrets. That is the torture a cuckold wants. My favorite line of the conversation was when I said, "I'm not a pussy like your husband. I'm going to be in charge and you are going to do whatever I want and we will all love it."

"Since I'm drunk, I'll just admit that is the sexiest thing any man has ever said to me."

We decided she would fly to me on a Thursday and leave Sunday. The next day she bought the ticket and told Tom she had a weekend date with someone. It led to a big fight at first but Tom is a cuckold and he eventually agreed to it. She never told him it was me.

I had some ideas on how to torture Tom just before the trip. I had Jen lay out all her lingerie and bikinis on a bed. I previously sent her three very revealing lingerie pieces and two skimpy bikinis. We both knew Tom wouldn't pick them but it was part of my plan. Jen made Tom come in the room and told him to pick out three of each that she would wear for the weekend. Tom picked out her most conservative bikinis and he told her no lingerie. Jen warned him to choose. He refused and told her she should only wear lingerie for him. Jen picked up the three skimpy lingerie pieces I sent her and told him, "I gave you a chance. I'll take these three with me and since you didn't do what I asked I will take these two bikinis instead. Now, because of you, my tits and ass will be out for everyone to see all weekend. Thanks, Tom."

As we got closer to the weekend, she told me Tom was a manic mess. Arguing about nonsense with her then begging to fuck her. She thought it was funny he didn't know if he was horny or angry. It didn't help that I prohibited them from having sex for the seven days prior and she made it worse by telling him it was to keep her fresh for her date.

Next, it was time to reveal she was coming to see me and some other rules for the weekend. I had her wait until she was through TSA screening so Tom couldn't make a scene. Jen facetimed Tom and then added me to the call. All color drained from his face when I said, "Hey, little buddy." (Tom is tiny at about 5'6" tall. He hates being called tiny or little) so I called him little buddy to maximize his humiliation.

He ignored me and said, "Jen, no."

She laughed at him. "Tom, yes. Once again, you wanted this and now that I enjoy it you keep trying to take it away."

Tom started begging her to not get on the plane but I interrupted. "Tom, not only is she flying here but I am going to fuck her silly this weekend. You introduced her to this lifestyle and now you're stuck with it. There will be rules for this weekend. If you break the rules we will change the ticket home to next weekend and I will keep fucking her. Do you understand?"

"Thats not right. You are my friend."

"So a stranger can fuck her but not your friend? That's some fucked up logic. Now, I asked you a question. Do you understand if you break the rules she will stay with me longer? The proper answer is yes sir or no sir.

There was a really long pause before he said yes.

"Jen, go in the app and change your flight home to Monday. If he's not going to follow the rules you will stay here."

"Ok, Ok. "I understand, sir."

"See Tom, that wasn't so hard. We will only call you cuckold from now on. Jen, you will answer to Jen or slut." Both of you will call me sir. Any time you are asked a question by me the answer must include sir. Tom you may not talk directly to slut from this point forward. Slut start a group text with the three of us. The only communicating will be in there. Tom, if I catch you texting her outside the group chat, she will stay extra days. Jen, if I catch you, there will be punishments. Do you both understand?"

I heard two yes, sirs. I knew Tom wasn't capable of dominating his wife but I was sure he wanted to. Every man does and I wanted him to know just how easy I was able to take his wife from him. I had a few more ideas.

"Slut, are you in the skirt I picked out for your flight?

"Yes, sir."

"I told you the other day you are only allowed to wear a thong or nothing all weekend, what did you choose under your skirt?"

"Thong, sir."

"Good, go into the bathroom and remove the thong. Leave FaceTime on and show us. Put it in your purse."

There was a long pause before she said yes sir. Tom was silent. Slut did as she was told in the bathroom and returned to her seat.

"Slut, when you land and walk into the airport you will go to the bathroom and remove your bra before I see you.

"Yes, sir."

Tom said, "Can I say something? This is my wife and I should have a say in what happens."

I told him no one wants to hear from a stupid fuck who lets his wife fuck other men. I saw Jen laugh but I was annoyed. "Did it ever occur to you that one of these men was going to treat her like a whore and fuck her so much that she might leave you. She's coming to get her brains fucked out by me in a beautiful beach town. She might not come back and if she does she will not be the same. Tom, you fucked up telling everyone at work you are a cuckold. So, neither of us want to hear any of your bullshit. I'm going to include you in this weekend when I want and you will accept whatever part I include you and the only say you have is thank you."

"Sir, my flight is boarding may I hang up?"

"Of course."

Two hours later Jen text in the group that she landed. Jen was stunning when I saw her. Short skirt (I knew there was nothing underneath), her big saggy tits (2 kids does that) bouncing as she walked without a bra. Beautiful face. Wow, was I lucky. She was so worried about the lingerie in her suitcase being pulled out at TSA that she checked her bag. After we got the bag we walked to my SUV with tinted windows. I leaned my seat back and pulled my hard cock out. "Let's start the weekend off right, take care of this and my woman swallows every time." She leaned over and gave me a decent blowjob. I took a short video of her bobbing up and down and sent it in the group chat. "Airport parking lot blowjob." After I came I added, "Swallowed every drop."

Tom never answered so I sent another text. "Tom, you will acknowledge all texts with a thumbs up unless you are asked a question that you will answer." He then gave a thumbs up to both the video and the swallowing comment.

Jen said she has never swallowed for Tom and she nervously laughed.

We drove home. it wasn't awkward at all. Almost felt like we were actually dating. She showered and put on the first lingerie outfit. I took pictures and put it in the group chat. She looked fucking amazing. I wasn't aggressive with her the first time. There was plenty of time for that. I gave her a great orgasm going down on her then fucked her. As I did, I told her I'm going to be gentle the first time and she responded, "If you want, but I didn't come here for shitty sex. I get that from Tom."

We both laughed and I grabbed her by the throat and choked fucked her. She wasn't kidding, I could feel her pussy soaking itself. I twisted her long hard nipples and slapped her saggy tits. I came hard inside her and we laid next to each other for a while.

I got my phone. "Tom, she's been here 45 minutes and I've fucked her and got a blowjob. Now we are going to the beach where everyone can see this amazing body." I sent a photo of her wearing the tiny bikini. She was reluctant to go outside in the bikini but I reminded her she didn't know anyone here.

When we got to the beach, I made Jen walk to the water and back. Every guys head turned. Even some women. She looked incredible. We had a few drinks and she got very talkative. She told me why Tom was the way he was. She said Tom has a two inch hard dick (I didn't know that) and he unfortunately had girlfriends who were not compassionate. His first girlfriend made the same joke every time they had sex for the three months they dated, "is it in yet?" When he would orgasm she would say I didn't even know you started. He had several other girlfriends who didn't help the situation either but his first wife sealed Tom's fate. The first time she saw him naked she laughed so hard they didn't even have sex. She then humiliated and called him Tiny Tom. Now, it made sense why Tom hated being called tiny or little. She called him Tiny Tom for their entire marriage. I heard her call him that numerous times but I always thought it was a height joke. She cheated on him relentlessly (another thing he never told me). Each time he confronted her she would say you're the one with the worthless dick. Why should I suffer. Eventually he had a breakdown (that I dealt with at work) and they divorced.

Jen believed Tom introducing her to this lifestyle was his way of controlling the situation. If it was his idea then she wasn't cheating but now I had stripped him of that because I was never his idea. I actually felt bad for him but his wife was wearing the tiniest bikini with a great body so I didn't let it bother me for long.

I could tell Jen was embarrassed wearing the bikini so I took her to the ocean and we went in. When she stood up she did that thing all women do where they cross their arms over their chest to block their hard nipples. Except I told her to remove her arms and put her hair behind her shoulders so everyone could see. I gave her a kiss on the lips, took her hand and walked her through the crowd to our towels. When we sat down I said, "Be honest with me, was that a turn on strutting through the crowd with that amazing fucking body?"

She giggled and said, "Yes, I can't believe it was."

I sent Cuckold a photo of her lying on a towel soaking wet with hard nipples. There is no way Tom would have ever got her to do this on the beach. As we talked, I would nonchalantly ask sexual questions of her until I hit the jackpot. "Ever have anal sex with Tom?"

"No."

"Anyone?"

"No."

"Fingers, toys back there?"

"A few times but never with Tom."

"I just can't believe this weekend keeps getting better."

"Why?"

"Look, you are fucking gorgeous. Beautiful face. Big tits, big nipples. Two kids and you're stomach still looks good. Tiny virgin ass. I'm going to take care of that this weekend."

"I don't know."

"Jen, it's the ultimate cuckold humiliation. Plus Tom probably tried to stick it in without warning a few times because he's a moron. We'll get you drunk. I'll massage you, set a geeat mood and instead of regular sex we'll do the other. Then we'll humiliate Tom about it."

We finished at the beach. On the drive home I made her take off the bikini top. I have tinted windows but she was petrified people could see through them. I took a photo and sent it to Tom with "Ever make her ride shotgun topless?"

I was so turned on that as soon as I opened the front door I bent her over the sofa and fucked her hard. The sand was a little uncomfortable for both of us but I came inside her after a few minutes of fucking.

We showered separately and headed out to dinner. I had her text Tom and ask if there was anything he wanted sir to do to her at dinner or later. Tom wrote back no and she responded that she knew that wasn't true. It took Tom a few minutes to respond but he wrote back that he would like to see her rub herself in the car on the way to dinner. There was no way I was going to let Tom dictate even one thing this weekend. So I rubbed her clit instead.

I had Jen video me doing so and she sent the video. When we arrived at the restaurant I told her to lean back in the seat and text Tom: Thank you Cuckold, I am so horny now I begged sir to make me cum in the parking lot before dinner. He said only if I agree to anything he wants later. I don't know what it is but you got me so horny Cuckold I agreed to do whatever he wants tonight. She then sent him a photo of me between her legs with her short skirt pulled up. Slut came easily in the parking lot.

After dinner we went drinking. Both of us knew what I was doing and she never objected as I fed her shots of Tequila on top of the Margaritas. When she was ready, I took her home. She put on another lingerie outfit and we FaceTimed Tom. I had her licking my hard cock when he answered so he saw that. I then sat up against the headboard and she slid between my legs so we were both seated and talking on the phone holding it in front of us. We both wanted to see his face.

"Cuckold, did you really send your wife to fuck other men knowing she had a virgin ass?"

Silence. (I was sure he knew where this was going).

"Cuckold, you had to know one of us was going to find out."

Silence. (I am sure he was sick to his stomach).

"Cuckold, you have a choice. You can either be on FaceTime when your wife gets her ass fucked for the first time or I can send you photos when I'm balls deep. What do you choose?"

"Jen, don't. I begged you to be the first and you always said no."

"Cuckold, let's be honest I should have let you be first since you are my husband but I wouldn't have felt it anyway. I'm not sure it would have even been considered anal sex if you can't get it in more than an inch but I do feel bad for not letting you try."

(Wow, I had been telling Jen a lot of things to say to him to humiliate him but this was all her doing. I was right, she was not going back to him the same woman).

"Slut, go in that closet and grab the container of coconut oil. Cuckold, make a decision FaceTime live or photos."

Tom disconnected the call. Jen came back in the room and asked what he decided. I lied and said photos.

I massaged her as promised and introduced the coconut oil around her ass. During the massage I slid my hand between her thighs. She was dripping wet and willingly spread her legs. I rubbed her lips, thighs and clit. I inserted a finger to use her own juices and dragged it across her rosebud. I then added coconut oil to my finger and slid it slowly into her ass as I massaged her neck with my other hand.

I stopped and took a photo of her virgin asshole. I sent it to Tom with "before."

I oiled my raging hard on and put it to her ass. I whispered in her ear, "Are you ready?"

"Yes, sir."

For her first time she had a cock slide into her ass. She tensed like most women do the first time but I talked her through the initial discomfort and before we knew it I was fully inside her ass. I didn't move much so she could steady herself. "Are you ready gorgeous?"

"Yes, sir. Are you all the way inside?"

"I am."

"Take a picture and send it to him."

I sent the photo with "during."

I wanted to fuck her ass so hard but I knew I shouldn't. I decided to go easy but talk to her like a slut and get her to promise me one thing.

I was easy on her ass. Slid slowly in and out. Told her how hot she was. How tight her ass was. She relaxed after a few minutes and said this isn't so bad.

"When you take a woman's ass she's yours. She's your slut. Say it."

"I'm definitely your slut, sir."

"Promise me one thing. Tiny dick is going to beg for your ass but I own it now. He had 13 years and never tried. I'm the only one who gets it. If you want anal sex you get it from me only."

"I promise."

"Say it again."