Fulfilled Fantasies

I don't remember how I found out, but a couple of years ago I came across a European website where American women would advertise as escorts. Every so often, I'd take a look and see the various women posting ads.

Years ago, I had an escort act out a particular fantasy. I had her tie me to a chair, straddle me naked, and tell me that if I told her a good sex story, she would untie my hands and I could play with her ample boobs. The real game was that no matter what story I told, she would say that the story was shitty, slap me, and not untie me. Basically, tease me for two hours where I could look at her naked body, but not touch her.

I was looking to reenact that fantasy with another escort. One day, I came across a woman that seemed perfect for the role. She was an older woman, in her 40s with large breasts. Her profile said that she was comfortable with domination. I watched her advertise every day for two weeks before I decided to call her for an appointment.

I described my fantasy to her. She asked me if I had a chair that would be comfortable for me to be tied to. She explained that she didn't have a comfortable chair in her apartment.

I wasn't comfortable with a stranger coming over and tying me up. It would be too easy for her to leave me tied up. I thought about meeting her at a motel, but I decided to give her a chance. I wanted to experience that tease again and she made it convenient by coming to me. We made arrangements for her to come over and tease me Wednesday evening.

She arrived right on time. We sat down on my sofa and went over the fantasy again. I could provide more details to her on the sofa than I could over the phone. While we were talking, she told me her name was Jennifer.

I stood up, undressed, and sat in the chair. Jennifer tied my wrists to the back of the chair. Then she stood in front of me and did a striptease. She straddled me naked. I don't remember all the stories I told, but her response was the same. She'd tell me my story was shitty, slap me, and demand I tell her a better story. She taunted me by holding up her breasts right in front of my face and asking, "Don't you want to play with these? I want you to play with them. All you have to do is tell me a good story."

The two hours flew by. When it was time for Jennifer to leave, she stood up, got dressed, untied me (whew), picked up the envelope with the money, and left. I noticed how wet my leg was. She must have enjoyed my stories.

After I put everything away, I went to my bedroom and masturbated, thinking about the experience. Jennifer played her role well and I enjoyed the way she teased me. I got dressed after resting for a while.

I'd call Jennifer once every two to three months. She would come over, tie me to the chair, and tease me by straddling me naked. I was running out of sex stories, so I started talking about my tease and denial fantasy. She could tell I wasn't just telling stories and asked me lots of questions about my fantasy.

At first, I thought Jennifer was just making conversation, but she kept coming back to the part of my fantasy where my wife's boyfriend comes to visit her and my wife is having sex with Mark, one of our neighbors. Mark and his wife Leslie are swingers, so he wasn't cheating. In other words, she was interested in the cuckolding part of my fantasy.

From then on, when I'd invite Jennifer over to tease me, I told her cuckolding stories. She seemed to really enjoy my stories, even though she was playing her role and telling me how shitty my stories were.

One day when Jennifer was over, teasing me, she asked me, "Why do some men like cuckolding? All the other men I've known would be furious if their wife or girlfriend cheated on him, never mind enjoying her cheating.

I didn't want to break the fantasy, but I could tell she was serious. I explained that cuckolding wasn't cheating. Cheating is when you go behind your partner's back to have an affair. It's a trust issue. Cuckolding could happen as a result of cheating if the husband or boyfriend doesn't want to lose her. More likely, cuckolding is something the couple discusses beforehand.

Jennifer kept me tied up for twenty minutes over the two hours to make up for the impromptu discussion, which I appreciated.

The next time I saw Jennifer, I told her about an idea I once had. I told her about an escort that would tie me up in the corner of her bedroom and see clients while I was forced to watch. She seemed to like the idea, so she asked me lots of questions about how the scenario would play out.

After Jennifer left, I didn't think too much about my idea. It would be a pain for an escort to set up. The clients that she saw with me in the room would have to agree in advance that I'd be in the room. But, she seemed to enjoy my idea.

One day I received a call from Jennifer. While her number was in my phone from me making appointments, she'd never called me before, She told me to meet her at a local motel the following Friday night, at 7 pm.

I didn't think too much about the call. Maybe it was a gift for all the teasing sessions I'd purchased? She didn't mention a payment. I wondered if I should bring the usual amount I paid her.

I arrived at the motel a little early Friday night. I texted Jennifer, and she replied with the room number. When I knocked on the door, she let me in. She was alone.

"Undress," Jennifer commanded.

I undressed and she tied me to the motel room chair. After I was restrained, she grinned at me and said, "I'm seeing three customers tonight, and you get to watch us have fun."

I smiled. Then Jennifer surprised me again. She went to her travel bag and pulled out a chastity cage. Because I was restrained, it was relatively easy for her to slide the ring over my balls and lock the cage to the ring. After she finished, she smiled and said, "Now you won't show my customers how much you enjoy watching me have sex."

Jennifer sat on the bed, flipped on the motel TV, and started watching some drama. I could see her sitting on the bed, but the TV wasn't facing me.

Finally, I heard a knock on the room door. Jennifer turned the TV off and answered the door. When they came back into the room, they were still kissing.

They made their way to the bed. Jennifer helped him undress and after he was comfortably lying on the bed, she did a striptease. I felt my cock getting hard in the cage watching them.

Jennifer got on the bed and in a cowgirl position on top of his cock. I could see her back and a little of her side from where I was sitting. After he came, she got off and lay down next to him, snuggling with him.

I was surprised when he asked Jennifer, "What's with the guy tied to the chair?"

Jennifer replied, "That's my boyfriend. We've been going out for over a year, and in all that time he's never touched my boobs or pussy. I told him that if he watched me work, I'd let him squeeze my boobs."

Immediately, his hands grabbed her breasts. "You mean like this?" He was kneading them like bread dough.

"Well, a little more gently," Jennifer replied. He manhandled her breasts for at least ten more minutes before he stopped. Like he was rubbing it in that he had access to her breasts and I didn't.

When his time was up, Jennifer helped him get dressed. She saw him to the door naked.

After he left, Jennifer went into the bathroom and took a shower. When she came out into the room, she got dressed and put the TV back on.

Two more men came to see Jennifer. The scene was basically the same. He and Jennifer would have sex. One man fucked her doggy style and I got to see her hanging breasts swaying. While they were cuddling, the man would ask her about me. She told each man the same story and both men reacted the same way by vigorously manhandling her breasts for a while.

After the third man left and Jennifer was dressed from her shower, she untied me and asked me, "Did you enjoy the show?"

I was a little miffed from her ignoring me for five hours, but I could tell that she went to a lot of effort to make my fantasy happen. "Yes, I enjoyed it very much."

Jennifer smiled. "I had a lot more fun than I expected. You told me the men would grab my tits, but I was surprised at how forceful they were." She rubbed her breasts through her top and continued. "Not that I'm complaining too much. My poor nipples are going to need some time off."

Jennifer sat on the bed and told me to get dressed. I reminded her that she'd locked a chastity cage on my cock.

She teased me by saying, "I thought you wanted a tease and denial relationship."

I replied, "Do we have a relationship?"

Jennifer went to her bag and came back with the chastity cage key. After she unlocked the cage and removed the ring, she watched me get dressed, and I left. On the drive home, I thought, sometimes fantasies do come true.