Long Island Cuckold Ch. 10



Contains the following perversions: Cuckolding, bisexuality, homosexuality, toilet play, humiliation, degradation, chastity…and more.

My advice is not to read on if you do not care for these things.

Thanks for reading!

Civil feedback is always welcome — negative or positive.


The night we came home from Las Vegas, Donna and I made love on and off throughout the night. I spent much of the time with my face between Donna’s legs, either eating her pussy or her ass. At one point before midnight I was licking her pussy. I wasn’t giving her head to make her orgasm.

She had orgasmed not too long before.

I, of course, was not going to orgasm since I was still locked in the CB-3000. I was just licking her gently. Kind of soothing her.

She leaned over and grabbed her cell phone from the table, then motioned for me to sit in the bed with her.

I sat upright and Donna leaned against me and started to play a video of me and the transvestite from the other night in Las Vegas. The video started with me on my knees in front of her, struggling to suck her cock.

Donna said, “You jumped to suck on her cock. She certainly isn’t a feminine transvestite. We bumped into her as we were passing a parking lot and we struck up a conversation and she was into having sex with you. You seem extremely focused on sucking her cock. Look at how much you are trying to take in your throat.”

Donna’s breather was getting a bit heavier as she watched. I saw her free hand was between her legs and I could hear the noise of her wet pussy being manipulated by her hand.

Donna asked me, “Mike, are you gay? Rob thinks you are. I think this is so hot, but seeing you focus on pleasing this unknown person makes me think that is a possibility.”

I was looking at the screen.

It was humiliating and degrading.

I was sucking cock, licking balls, and eating ass. I’ll admit I was doing it all with great energy and enthusiasm. My eyes were closed throughout everything, which makes sense since I was in my private world. The biggest thing that struck me was how much I hate seeing pictures and videos of myself. I thought that was odd. Here I was doing something I absolutely shouldn’t be doing, that I felt humiliated doing, and the main thought I had was, “I look horrible on video.” Odd for sure.

I said, “I don’t know Donna.

I don’t. It confuses me. I’m more focused on the humiliation of it all. Of being used. I try hard to please and I’m just thinking that it is my purpose to be used and humiliated.”

Donna watched for a while more and watched me getting fucked. She said, “Wow, she wasn’t being kind to you there. She is big and she just kept pushing you down. Were you in pain?”

I replied, “A lot. I had to focus on being a good submissive.

I kind of put my mind somewhere else.

It was hell. I kept imagining that this must be what it is like to get raped in prison.”

Donna took her hand away from her pussy. She pushed two fingers, wet with her juices, into my ass. I moaned as she did it. Mostly in discomfort.

As she probed, she commented, “She did some damage back there. I’ll leave your butt alone for a while. I’m sorry I didn’t know it was that bad.”

Then she took her fingers out of my ass. She was looking at me sensually. She took those fingers and traced them around my lips, then had me suck them clean, then she kissed me. We kissed for a while.

We ended up with my head on the pillow looking up at her. She leaned on one elbow, tracing my face, eyebrows, and nose with her fingers, and intermittently kissing me.

She then smiled and said, “You’re not gay, Mike. One of the things that Jinxypie and I spoke about is what drives different cuckolds.

Some are bisexual or gay. Labels don’t matter, I’m sure you’re bisexual to a degree. I think everyone is. I’m not sure you’re any more bisexual than I am. What you are is a submissive. You are a masochist in a way. A mental masochist. You crave humiliation. The good news for you is, pervert, that your perverted wife loves, loves to see you like that.”

She mounted her pussy on my thigh so I could see how wet she still was. As she glided on my thigh with her pussy, making it wet, she said, “See?”

I just nodded my head up and down.

She went on, “One of the goofy things you’ve always done is look at other girls. Another woman walks by and as long as she is somewhat attracted, there goes your head following her. Not once have you done that with a guy. I pay attention to that. Guys aren’t as observant.”

She also went on, “You’re eyes are closed in the video because you want the humiliation, but being with another man is distasteful to you. Rob thinks you’re gay. I know you’re my little sick and demented husband.”

I was holding the phone now and the video was playing me kneeling in the tub in the bathroom drinking the transsexual’s urine. She said, “Darn, Mike, you’re like an addict. The more you’re pushed the deeper you go.”

My dick was struggling in the cage as the İstanbul Escort video ended. Donna acknowledged that by holding and caressing it. That just prolonged my discomfort.

Donna then said, “I’m afraid I’m turning into an addict as well and we’re both going to be out of control.” Holding the phone again she said, “New rule: Nobody, not anyone else, not us, can take pictures or videos of what we do.

That will get us into trouble. It is too tempting. We have to be firm on this.”

I completely agreed and told her that. I didn’t remind her that she was the one that took the video.

I did tell her that I think she summed us both up pretty well. I was turned on by the humiliation. The abuse, use, and degradation were what did it for me.

As we were laying there, but not quite drifting off to sleep, I felt I had her in a moment where we were husband and wife again. I asked her if she was serious when she said Rob and Max were better in bed than me.

Oddly, putting all of the humiliation stuff aside, I was curious if she was just teasing me with it.

Her answer was honest and direct, “Yes.” She told me that I was a sweet, tender, caring, and giving lover. She said she loved me for that and would never want to live without it. However, there was no contest, they were better lovers. She reminded me we discussed this before and that they were not submissive at all that they used her for their pleasure and that she needed that. Not all women are alike, just like not all men are alike, but she needed to be used by a man. When she didn’t get that she felt frustrated and missed something.

She saw the look of concern on my face. She told me not to worry. She needs what I give her. I give her love and she loved me. She also needs a sexually dominant man.

I was just about to settle down to doze off when I asked her if she had seen other men other than Rob or Max while we were married.

Donna asked me, “Who controls our sex lives?”

I replied, “You do.”

Then I added, “Ma’am.”

She said, “Right.

What you’re feeling are angst and jealousy. That is hot.

I’ll let you know anything that I care to.”

Well, that didn’t answer my question. However, Donna rolled over to go to sleep.

She quickly rolled back over facing me and asked, “Did I go too far in Las Vegas? The way I treated you with Rob or with the transsexual.”

I said, “No Ma’am. So long as it is what you want, honestly, it turns me on to do it.”

Donna said, “We have already broken each other, haven’t we? You need to tell me in times like this if I’m pushing you too far. If I push you too far when we’re doing something, you can’t be scared to call it all off. I don’t want to lose you and I don’t want you to lose you.”

I said, “Yes Donna” and kissed her.

She rolled over and we both went to sleep. We were pretty tired from the trip and used the last of our adrenaline in bed. The CB-3000 didn’t even wake me up.

I remember when I woke up, I jumped into a sitting position. It was 8 am and it was a workday. Then I quickly relaxed because I was smart enough to tell people I wasn’t going to work. I’d probably log in later from home, but I told everyone I wouldn’t be working to allow me to catch up.

Donna laughed as she saw me jump. She reached out and caressed my chest and stomach and said, “You’re off today, honey.


I laughed a bit and let her know I was so sound asleep I wasn’t sure what county I was in when I woke up.

Her hand moved down to my balls and the CB-3000. She caressed and played with it. I groaned a bit and told her she wasn’t doing me any favors. My dick was pressing into the spikes pretty hard.

She didn’t acknowledge that she hear me and moved the sheet back and lowered herself. She licked my balls and ran her tongue over the CB-3000 letting her tongue touch my dick where it could. It was wonderful agony.

She did that for a while, then raised herself and started to move her head back and forth so that her hair would go over my dick, balls, and thighs. It felt so good. It was torture. As I was getting lost in the feeling she raised herself and her face was hovering over my head. I could tell she wanted to drool and spit into my mouth. I opened my mouth and with her hair draping over my face, putting us into a little cone of sexy Donna-ness, she drooled a few times into my mouth.

Then she said, “I have to pee.” And she crawled away from me.

She was leaving me extremely horny and I saw her naked body and couldn’t resist. I asked, “Donna, could I help you with that?”

She asked, “Help me with what? Peeing?

I’ve been doing it for years. I’m good at it.”

I said, “I mean, do you want to use me to drink your pee?”

To that, Donna said, “You mean you want to drink your wife’s urine?”

Pleadingly, I said, “Yes Ma’am.”

Donna said, “What a disgusting boy you are. You want to drink your wife’s urine. Well, ok, but I promise I will think less of you and if you spill any you’re licking Kadıköy Escort it up.”

Then I was lying face-up on the bathroom tile. My wife squatted above me. Spit once into my mouth, then slowly pissed into my mouth as I gulped down her urine.

She did tell or even ask me to do this.

I begged for it.

When she was done she had me lightly lick her clean, then she got up, washed up and, brushed her teeth while I got up and used the toilet.

When I was washing up and brushing my teeth she threw on a t-shirt and went to the kitchen. When I was done, I was naked, except for my CB-3000, and thought I should probably stay that way.

When I got to the kitchen the coffee was being made. That is such a terrific smell. Donna was making bacon and eggs. It is a rare treat for us. While she was at the stove she looked beautiful and I came up behind her and hugged her and kissed her neck while she cooked and made cooing sounds.

I made the right decision not to wear clothes. We were back in Donna/Mike marriage mode, but I was still her cuckold. By Donna not commenting on it and by her occasionally touching my balls or CB-3000 it told me that is what she expected.

When we finished with our bacon and eggs and were drinking our coffee at the table, I asked Donna about Rob. I wasn’t sure if it was time, but I was curious about what had happened.

Donna didn’t look me in the eye. She looked sad. She said that Rob asked her to move to Canada. She said she couldn’t but could visit. Rob said he wanted to be alone with her and she said she could visit him without me.

I was a bit jealous about this. My stomach tightened, but I was accepting of it.

She then went on and explained that she offered to have Rob move in with us. Since his business wasn’t stable, he could move in with us, we would support him while he worked out the visa and work situation. Donna said that Rob first was objecting to thinking that I was gay and that he wasn’t into that. Then he kept saying that he just wanted to be with Donna.

Donna had tried to come up with an arrangement. She expressed her love for him to me. She said that she offered to keep me apart from him, that she wouldn’t have any contact with me while he was around. She also tried to let him know that it may be fun to have a slave, someone to do all the running around for him and that money wouldn’t be an issue.

Part of me was thinking, “What the holy hell? Are you kidding me??”

She was serious and I saw the sad look on her face and I melted. I knew that I would have submitted to it and I am thankful that it didn’t happen.

She told me that they didn’t’ fight, but they agreed that they wanted different things.

Almost as an afterthought, she told me, “You’re not negotiable, Mike. You know that, right? You’re my guy.”

I said, “Yes Ma’am.”

Then I had to add, “I’m not exactly sure what it means to be your guy sometimes.”

She smiled again, which changed my mood completely, and said, “Sometimes it is everything, it is the center of the universe. Sometimes it is going to be less than a pet.” She put her foot in my crotch, mildly kicking my CB-3000, and said, “…and sometimes, like now, it is like you’re almost fully my husband, almost fully a man, but…not quite”

I smiled and said, “Yes Ma’am. Thank you.

I understand that completely.”


Donna certainly gave me enough to think about. As the week progressed and I went back to focusing on clients and back to my dojo routing and completion, we didn’t have too much time to engage in “cuckold play” or whatever we want to call what this that we got into.

Donna was also planning to retire early. She had plans to shift her focus to work at a local food pantry. She was already speaking to them about ideas, fundraisers, and helping with logistics. This would become her new passion and I was proud of her. Not only for her capabilities but for wanting to increase the good that the food pantry could do for those who needed it.

The more I thought about the situation with Rob, I think there was a real attraction between Donna and Rob. I don’t think it was love and I’m not trivializing it. I haven’t expressed this to Donna (she may read this though), but I think had they worked out an arrangement, they wouldn’t have parted as friends. Rob was looking for a wife. My wife.

Donna was looking for someone to be part of her life, but she already had a husband. I was less confident about it then, but as time progressed, I’m extremely confident of that. Rob is a good guy and I mean that. I like him.

I think we all avoided some long-term pain.

I think Donna’s assessment of what motivates me is spot on. I was beginning to question if I was bisexual. Intellectually only. I don’t care about the label on me or others. There is a stigma for a “straight” guy and that is the humiliation component. The way Donna explained that I’m a masochist made sense to me.

I also completely understood her perspective. She wanted more than I could Ataşehir Escort give her. When we connected, we connected. I get that even with that, she was looking to be dominated herself and that isn’t me.

It isn’t that I don’t want to give her what she wants. I can’t.

Call me what you want, but I can worship her ass after she has been fucked by another guy, but I can’t bend her over and just take her ass forcefully.

Two other thoughts — She said she was as bisexual as me. That makes me smile. Also, she wouldn’t answer if she had been with any other guys since we have been married.

I think she wasn’t answering to tease me and play a “head game”, but I don’t know.

Over the next couple of weeks, we fell back into our once or twice a week lovemaking. Since I was still in Chastity and not knowing when I’d be out, it was mainly me worshiping every part of her body, especially her pussy and ass, and giving her oral to orgasm.

It was about this time that we switched from the plastic lock tags on the CB-3000 to a small metal lock. We were finding about every week or few days the CB-3000 needed to be readjusted.

Taking off the CB-3000 involved making my erection go away to get it back on. Ejaculation didn’t seem to be an answer that Donna thought was a good one, so it always involved my balls being hit or squeezed. You might think taking off the CB-3000 to have it reset on me would be something I looked forward to, but for that reason, I didn’t.

Since we were going through the tags, Donna thought we should use the lock that came with the CB-3000 and after seeing a picture of a woman wearing the key she began to wear the two keys for the lock. She would wear it if she was wearing a necklace, on a bracelet, and yes, on an ankle bracelet, too. It depended upon what she was wearing. They were mostly visible. I know that it is a common porn picture, so to this day when she wears the keys I wonder if people know what is going on. Men mostly, I would assume.

Donna started to complain about needing real sex. After hearing this for a few weeks, I offered the obvious suggestion that would solve both of our problems. She could unlock me and I’d give her a good fucking. That smart-ass response was met by a pretty decent roundhouse kick to my balls.

I stopped making that suggestion, but she did not stop her mild but somewhat growing complaint.

Back then we didn’t know much about the scene. We had an experience with Rob and Max, but they just wanted to fuck Donna. We had both spoken to Jinxypie and she was awesome, but that ran its course.

I didn’t know much about community sites back then, but I did know about Craigslist. This was before Craigslist was shut down. Both Craigslist and Backpage were shut down due to the “Stop Enabling Sex Traffickers Act” of 2017. The real difference is that Craigslist shut down on its own before the Feds put the block on their site. The Bedpage CEO was arrested and the Feds shut down their site.

Interestingly, other sites are up that just have the prostitution ads. That was the problem with Craigslist and Backpage.

The “new” sites don’t have personal ads, which was not the legal issue and that was the part of Craigslist we took a look at. How these other sites are getting around the law, I haven’t looked into it because I don’t use them.

We both looked at Craiglist together. There were two sections that Donna was interested in. One was Couples for Couple and the other was Men for Women.

It did start to open the world up for us in this scene. Specifically on Long Island.

We created a bogus email address with Hotmail (Feel free to call us “Boomers”) and began replying to a few of the ads that Donna felt were interesting. The responses ran the range from being dopey to amusing, to being something that we thought was genuine. Most of the guy ads were replied with asking for nudes from Donna and sending dick pictures.

We were a bit naïve and found out that most of the “Couple” ads were posted by men. I’m not sure exactly what they were looking to gain.

Perhaps they were looking for nude photos.

While we were ok receiving photos and we would not share them with anyone else, Donna’s rule was that we do not share pictures. We spent a few weeks weeding out the phonies and also probably getting rejected by some sincere people because we wouldn’t share pictures. We were intent on being as careful as possible.

There were a couple of younger guys that Donna was marking for the shortlist and a couple of couples as well. Just because of timing and schedules, there was one couple around our age that lived on the South Shore in Merrick, Mark, and Beth that we were making progress towards meeting.

We had spoken with Mark and Beth about what we were looking for. Donna was pretty descriptive about what we have done and was interested in.

They were mainly a swinging couple.

They had an interest mostly in Beth being with two men. Since Donna said, me having intercourse is not physically possible and she doesn’t want to see me with other women, you would think it was a deal-breaker. When the four of us spoke on the phone we hit off. We decided to set a date a couple of weeks out to get dinner in a place near them, then if we all agreed we would go back to their place for some fun.