A Cuckold Role Play

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Comment from the author: All people are of legal age. This is based on an actual event that almost took place. It contains elements that some people might not like, like paying for sex, light male humiliation and some male on male interaction, be forewarned.

The airline changed flights and this meant that I had an unexpected evening in the city. As always when I am in the city, I wanted to do something naughty. Like visiting a strip club, getting a massage with a happy ending or even visiting a sex worker.

Or perhaps something else? I was in the mood for something different. I just didn’t know what yet. While scanning a local escort forum I noticed a post.

“Anyone want to help me with a cuckold fantasy?”

The forum was for sex workers and clients, a place where people can interact with each other. So, the implication of the post was clear, pay a lady and do some cuckold role playing. It can be fun; it definitely was something different.

I contacted the person and we quickly started to chat on the phone. He called himself Brian and was in his mid-twenties. He watched a lot of cuckold porn and was interested in playing it out in real life. Since he wanted to get a sex worker, I assume he either didn’t have a partner, or didn’t want the partner involved. I had an open relationship with my wife before she passed away, so I understood some of the elements involved. He was very vague what he actually wanted, so I mentioned a few things, some ideas and he eagerly agreed.

Now the problem was getting someone to play with. It sounds strange; sex workers do fantasy all the time, right? Actually, no. Most girls don’t want to do things out of the norm. They want a guy to show up, hand over the money, shower, rub his back, wake his penis up, ride him for a bit and let him finish quickly, condom off, shower, kiss on the cheek, tell him what a good lay he was and bye-bye. There are a few ladies who really go out of their way to deliver an outstanding service and would consider something like this, but most of them don’t like last minute appointments, they are professionals.

I know one lady though. Mel is in her mid-twenties, blonde, has a stunning body, the best boobs I have seen. She is a student, lives from a small trust fund, but likes sex, so she makes some money with it. She mostly sees clients after hours and is very selective. She is expensive, not unreasonably though, worth every penny. I saw her a few times when I pass through the city, then I assisted her with a project for her studies and we became friends. We chat regularly, she would every so often complain about her family, her clients, her boyfriend or girlfriend and I would listen; try to say the right thing and be there for her, as a guy who is almost old enough to be her father will do. We still have sex every now and then, but it is more casual, sometimes we would get naked and busy, then we start to talk and pretty soon it is time for a shower. And while I always pay whenever I visit her, she usually protests, but I know it helps her a bit, the trust fund is not that big.

I quickly gave her a call.

“Hey, I thought you are on your way home? Want to come and see me?”

I explained my change in plans, then quickly what I had in mind. She laughed and we discussed details, made plans and agreed to a time.

I contacted Brian and told him I found someone who can help us. I told him to look her up on the forum, the girls post advertisements with a few photos of them and a brief description. He was happy with my choice. We arranged to meet at a shopping centre close to her. I told him not to worry about the money. The whole thing was a fantasy of mine too, I just didn’t think about doing it this way.

I had a quick shower, cleaned all the important bits, shaved and then got dressed. I made a stop at a local sex shop and then drove to the shopping centre.

I arranged to meet him near the food court, there was a fountain, he was supposed to phone me when he gets there. As always, I was early. I spotted him quickly; there were not many people and only one nervous looking guy. He was smaller than me, looked young, about Mel’s age. I walked up to him before he made the call.

“Hey Brain?”

He looked at me, I told him who I was and we shook hands.

“Nervous?” I asked, because I can see he was nervous.

“Yes, I didn’t think it will be real. This morning it was just a fantasy, now we are doing it.”

“Don’t worry. Take a deep breath. This is your fantasy. Just go with it. Don’t think about it. Mel is very good. If you feel uncomfortable şişli escort at any stage, use the ol’ traffic light code. Yellow means go slower, red means stop. “

He swallowed and smiled.

Since he was nervous, I suggest he take something to help him. I bought a jelly from the sex shop, it is supposed to make your dick hard and make you last longer. It works; I use it every now and then. I suppose using it too often might be a problem, but once in a while is not an issue. I told him it would help with his nervousness, in reality I wanted to ensure his cock would be as hard as it can get. I also took some. I handed him a bottle of cold water to wash it down. Then asked him to go get some flowers while I am going to get something from another store.

I walked into a lingerie store and made my way to the panties. I picked pink panties, smooth material and lace on the edges, with a little pink bow in front. Female panties are not made to support two balls and a cock, so it can be a bit uncomfortable. Especially since I selected a pair that will be slightly too small for him. I also grabbed a pair of black pantyhose. I met him at the flower stand, explaining that it always helps to bring flowers and a small gift when you visit a lady. We got some chocolates as well. There was not a large variety that time of day, but the lady made up a pretty flower arrangement that will at least last until the end of the night.

We drove to Mel’s place. It was a guest house, owned by a guy who rents the rooms to girls in the business. It creates a safe place for them, as far as I know it is purely a business transaction.

I called her at the gate and the gate opened, I drove inside and parked to the side. I gave Brian the flowers and chocolates and told him how to reach her room. She has a bigger room at the end of the hallway. I told him to relax; he took a deep breath and then climbed out the car.

I relaxed, imagining the scene inside. Mel has a way to make everyone feel at easy pretty quickly, she has a gift to guess what will work on a person. We agreed she would wear a robe, talk to Brian a bit, tease him a bit, before showing him anything. I also send the money for the appointment, double because it is two guys. It helps her a little bit.

I gave them thirty minutes to relax and get to know each other. I made the way down the hall, it is always exciting, sometimes you can hear moaning through the closed doors. I opened the door and found Mel and Brian sitting on the coach facing the bed. Mel’s robe was next to her, she was wearing a black corset, skimpy see-through thong and stockings. Brian’s shirt was open, Mel’s hand was inside. Brian looked flushed, excited.

Mel stood up, gave Brian a peck on the cheek and said “Looks my real lover is final here tonight.” She walked over to me and gave me a kiss that quickly turned into a hot, open mouth, tongue knotting kiss while pressing her soft body against me. She turned us slightly so Brian could watch. She placed my hand on her ass, I squeezed it.

Finally, we broke it off. I handed her the shopping bag with the panties. She quickly looked inside, smiled and went to sit on Brian’s lap, pressing her breasts against him, whispering into his ear. I knew she was telling him to get naked. Brian stood up and removed his clothes. He seemed a bit shy. I went to sit on the bed next to Mel.

It soon became apparent that Brian’s cock was rock hard. When he removed his briefs, his cock stood erect, pointing up to the roof. Mel stood in front of him, cupping his balls, slightly massaging them. She showed him the panties and told him to put it on. He hesitated slightly, then shrugged and pulled the panties on. It looked funny, the panties made a bulge and the tip of his cock was peeking out.

Mel guided him to the end of the bed, told him to sit and face us. She whispered into his ear and ran her tongue down his jaw before kissing him. She used the pantyhose to tie his hands, crossing the legs behind his back and placed the crotch part into his mouth. It is simply restraint, more for show than anything else. I removed my clothes, leaving only my boxers on.

Normally Mel would insist in a shower before the time, she would offer to join, wearing a swimsuit that will quickly become transparent when it is wet. But we agreed this time a shower would break the flow of events.

Mel likes kissing, so we spent some time making out, rolling around, our hands exploring each other. The corset had a zip, making it easy to remove. Mel took it, climbed over me to Brian, placed taksim escort her knee against his crotch and showed him her boobs. Like I said, it was perfect, with light pink nipples. She asked if he liked her boobs, he nodded. She rubbed the corset against his face, telling him to smell the cups. Finally she rubbed her boobs against his face, pressing harder with her knee against his crotch.

She returned and stood over me. I kissed my way up her leg and removed the thong with my teeth, dragging it down. She turned to Brian, standing in front of him, her pussy level with his face. “Do you like what you see?” she asked. He nodded and smiled. “Would you like to touch me?” she asked again. He eagerly nodded again. “Well you can’t.” She ran her hand over her pussy. “This is not for you.” She fit the thong over his head, arranging it so the crotch was covering his nose. “Smell me baby, that is as close as you will ever come.”

She turned to me; I was at an angle on the bed. She kneeled over me, standing on her hands and knees, her ass pointing in Brian’s direction, making sure he can see her breasts resting against my chest. We kissed, touched, squeezed; I ran my hand between her legs, pressing against her pussy with my arm while grabbing her ass.

She removed my boxers, dropping them next to the bed. My cock was rock hard, pointing up. She smiled at me and whispered, “You like this, don’t you, you dirty old man?”

Turning her body around, placing her pussy over my face, she looked at Brian. “This cock can have me. Look how hard it is. Don’t you wish it was your cock in my hand, or maybe in my mouth?” I felt the warm wetness of her mouth as she took me in as far as could, which is pretty far, she has amazing deep throat skills.

Meanwhile I used my tongue and traced her pink bits, exploring the soft folds. She kept saying stuff to Brian, telling him how nice my cock was, how nice my tongue was in her and so on; sometimes her words were muffled by my cock in her mouth. We kept going like that for a bit, until she nudged me and we turned around. Now Brian could watch my tongue lapping at her. She was enjoying this whole thing as well, that much was clear. It was like a sticking my tongue in warm jelly. I had a breast in one hand. I reached out with my thumb and gently brushed it over her butthole. She squeezed my cock in a vice-like grip and when I did it the second time, she exploded, flooding my mouth and face, moaning and gasping and squeezing my dick hard with her hand. I did it a third time, got the same reaction. When she calmed down, she climbed off me.

She faced Brian again, holding on to his shoulders. “Do you think I am ready to fuck, Brian?” she asked, lifting her hips in his face’s direction. I was sure he could smell her, see the wet mess between her legs. Meanwhile I rolled a condom over my dick, safety first.

Mel knelt in front of Brian, her face close to him, her ass to me. I positioned myself and pointed the tip of my cock to her opening. She explained to Brian what is happening behind her, then pushed back and with one go my cock slipped into her almost all the way. Taking over, I started to thrust, holding her by the hips. She continued to tell Brian in a breathless voice what is happening, how my hard cock was slamming into her, how he will never feel how it feels. Moaning close to his face, her breasts swinging, almost touching his chest.

We changed position. She mounted me in reverse cowgirl, telling Brian to watch another man’s cock inside her, while finding her rhythm. Brian could clearly see my cock splitting her open, moving in and out.

The final position was missionary, with her head on Brian’s lap, his cock brushing against her cheek. I could see the pre-cum dripping from the tip of his cock. Mel reached out and locked her hands behind Brian’s neck while I thrusting in her. Her breasts were pushed up by her position, they kept wobbling. When she felt me getting closer, she lifted her hips and told me to fuck her harder. I kept pumping, the end was near, there was no stopping now. I exploded inside the condom. She moved her hips as I slow my pace down, making me spill more cum into the condom. Finally I was done. I leaned over her. We kissed, soft, sensational, both out of breath.

I climbed off her. She stood up, showing her freshly fucked pussy to Brian. “Don’t you wish it was you that fucked me so good?” she asked.

She helped me remove the condom, I reached out for the wet wipes, but she stopped me. She climbed on Brian’s lap, naked, sweaty and smelling like sex. beşiktaş escort She ran her hand over his chest, playing with his nipples. “Did you like that, baby?” She asked in a husky voice. “Did you like watching me getting the fucking of the week while you cannot touch me?” Brian nodded. She reached out and squeezed his cock, making him groan. “Would you like to come, baby?” Brian nodded more. “Then you have to do something for me.”

She waved her hand, calling me over. I stood next to bed. She placed one hand on my butt, taking my cock with the other and pointed it at Brian. “I want you to thank him for the fucking he gave me that you couldn’t.” She moved on his lap, probably pressing against his hard cock. “And I want you to kiss the cock that gave me such pleasure.”

Wait, what!? That was not part of the deal. We were going off script now. She squeezed my butt and cock. “Will you do it for me baby? Then I’ll let you come. You want to come, don’t you?” Brian hesitated and then nodded slowly and shyly.

Mel removed the pantyhose from his mouth and pulled my cock closer to his face. Brian looked up at me, “Thank you for pleasuring her with your cock, sir.” His hard lips touched the tip of my cock, then he relaxed and his soft lips closed around the tip of my cock. I was almost horrified, there was still come on my cock and Brian was kissing it. “That’s it baby, that is how we thank the cock that did what you couldn’t.” Mel leaned in and gave Brian a proper kiss, pressing her body against his.

She instructed Brian to move to the couch, placing his legs over the back. She helped him getting into position; he was on his back, hips in the air, cock pointing down to his chest and face, head resting on the edge of the couch. Then she called me over, pressing her body against mine, and said, “I want to you to wank him off.” I stared at her; this was definitely not what we discussed. She asked again, purring in my ear, pressing her soft body against me. How can I say no to this sexy young woman I just fucked?

Mel positioned herself over Brian’s face. “Baby, the only way you are going to come is with me sitting on your face.” She didn’t wait for an answer but lowered her pussy over his face. His tongue started to explore her. I reached into the panties and gripped his cock. It felt familiar, yet strange. I started to move my hand up and down, like I would do with my own cock. Mel was riding his face, moaning again, one arm wrapped around me, her hip against mine.

It didn’t last long, when Mel started to gasp, Brian exploded with a loud moan. A thick stream of man cream flew from his cock, landing on his chest. I kept jerking and another stream flew out. And another. Mel was going crazy on his face, for a moment I thought she was going to smother poor Brian with her pussy. Finally she stood up and with shaking legs sat down next to Brian, taking his cock from me and squeezing the last few drops out.

She told me to hand her my condom. She squeezed my cum out over Brian’s chest, creating a love juice mix. She told Brian to rub it over himself, use it as a lotion. Brian did something unexpected. He scooped up the cum mix on his chest and sucked it off his finger. Both Mel and I looked on in horror, while we were pushing the limits of safe sex with the juices and interaction; he just placed an unknown man’s cum in his mouth, and swallowed it. He rubbed the rest over his chest.

That concluded our playtime. Mel handed Brian some towels and pointed him to the shower. She gave me a hug and told me it was incredible, before she joined Brian in the shower. Both emerged a bit later, smiling and relaxed. I took went to shower quickly, spent, felling warm and fuzz inside. The evening was different. Overall, I felt good about it.

Mel didn’t join me; she spent the time chatting to Brian. They discussed the evening, the expectations and whether it was met. Brian couldn’t stop grinning.

Eventually we left. Mel hugged us both, made Brian promise to come and visit her, told me it was always nice to see me and we should try new things like this more often. Before we closed the door, she stuffed the pink panties in Brian’s pocket.

Brian was quiet on the way back, but claimed he thoroughly enjoyed the evening. He thanked me, shyly, after all he kissed my cum covered cock and I jerked him off. And he swallowed a mix of our cum. It makes one a bit awkward. I jerked off a stranger and had him kiss the tip of my dick. It certainly was a new experience for both of us.

Final comment from the author: The beginning of the story is based on a true event, but ultimately the guy got cold feet. I visited the lady anyway and we discussed how it would have been, I used some ideas here and added a few of my own.

This is my first submitted story, any feedback is appreciated.

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