I learned about KeylimePi in one of the cuckold forums around. No, I’m not going to tell you which one, but I started emailing him after I saw he was looking for the truth about why cuckolds stay in their marriages. Every cuckold relationship has its reasons. I can only talk about mine. 

Most people think they are average, normal people, and I’d pictured myself as an average guy, but about ten years ago, I learned I wasn’t. Sexual role play can be a way to create some excitement in marriage, and it did with me and Jean. We started with the nurse-patient and French maid-and-lord scenarios. That drifted to picking up a stranger to fucking scenes.

“Jean, we both want some more excitement. Have you ever done role-play? Pretend we’re different people? I’m not into pretending you’re a little schoolgirl, but, uh, maybe a maid at someone’s house.” We didn’t do it often, but eventually, we had some special costumes we wore. She was a maid, and I was a French lord, seducing her, and that slowly drifted into other dominant/submissive roles.

We’d been doing role play off and on for about a year when Jean suggested trying something different, “I want to do something edgier, something different. I think you’ll enjoy it. Um, let me go into Monaco’s before you, and I’ll try to pick up a guy, and then you can come in and chase him off.”

I hesitated, and she said. “I’ve always wanted to see if I could pick up guys at bars, and I’ve never done it.”

This is making me uncomfortable, but I’ll try it, once. 

I felt a shiver go down my spine, but I agreed. I knew the reputation Monaco’s has as a pick-up bar, and that made it more believable. This was the first time I picked out Jean’s outfit and trimmed her pussy hair for her pretend new lover. The thing I remember the most is my hard-on. It felt so erotic, getting Jean ready for someone else, even a pretend someone else.

When I followed Jean into Monaco’s, I sat at the bar and looked around, trying to figure out who might try to pick her up. A big blonde guy was sitting at the other end of the bar, checking the merchandise available. I hoped he wasn’t the one to try with Jean; he intimidated me. Could I try to intimidate him enough to leave her to me? I didn’t think so.

When he got up, he walked toward Jean, but walked past her and spoke to a black woman sitting behind Jean. When he sat down at her table and engaged her in conversation, I took a breath; I hadn’t realized I’d quit breathing when he stood. If he’d approached Jean, I wasn’t sure I could have chased him off. That left me unsure of myself, thankful he hadn't, and regretful he hadn’t. I was wondering what Jean would do if he decided to approach her. When another guy approached her, he was more my size and just a touch diffident. When I went to chase him off, he left with no real argument. I led her out of the bar, and I had her naked before we got home. The sex at home was terrific.

I loved what we were doing, but some of my reactions were surprising. I enjoyed getting Jean ready for the trips to the bar and trolling for guys too much. 

I don’t know, are we enjoying this too much? We’re going out almost every weekend to Monaco’s or the Hi-lighter. Is this going to lead somewhere I don’t want it to? My cock seems to be enjoying it, at least. Um, and Jean, too.

After one especially arousing excursion, where I had to intimidate the other guy; Jean turned in bed and kissed me. “That was fun, Miles, but I have an idea that will make it even stronger and more intense for you. Um, and me too. We’re both enjoying the tension. … like last night, um, of me flirting with guys in the bars. 

Jean kissed me again and continued, “I think I want to go to Monaco’s this Friday … alone, leaving you here to imagine what I’m doing. Imagine who is hitting on me, am I kissing them? What is happening? Um, when I come home, I want you ready to fuck me so …”

Jean wants to go out alone? Let other men approach her? Um, no, just no, or is it maybe no? My cock is interested, but it’s just a bad idea. The pit of my stomach is turning over, but I also felt my cock harden. This could go further. Was this the end? As far as we would take it. Or would Jean take it to its obvious conclusion? Has Jean been leading me to this? All along. And I hadn’t seen it until now? Shit, if we started this, there was only one more step. Did I want to risk that? Did I want that? Could I live with it if she took that step?

I interrupted Jean, “I’d need to think about that. That’s a big step, don’t you think?”

“Yeah, it is, but I think you’d like it. Just think, we could buy special clothes for me, and you could get me ready to go out. You always enjoy doing that. And when I come back, wowser, it will drive you crazy. There is one thing, though: I bought you a cock cage, so you can’t masturbate while I’m gone. I’m going to want it when I get back. So no jacking off.”

When she pulled the cock cage from her bedside table, I felt my cock leaking cum onto the sheets. I realized I might actually do this. “Like I said, I need to think about this.” 

My god, is it possible I’ll do this? It’s clear where this is headed; did Jean do this intentionally? 

I thought about it; tracing the history step by step. I couldn’t believe that she planned that far ahead. Is she planning the next two steps? God, yes. I can just stop it here. Go back to before the role-play even. 

I felt Jean caress my cock, but she only kissed me. I knew she must have felt my cum. What the hell?

I spent the next week trying to decide about Jean’s suggestion, with no success. It was Tuesday, the next week, that I started looking for clothes for Jean’s adventure. 

I kept thinking of her trip alone as her adventure. That allowed me to think about it without consciously realizing what it meant. 

I took a couple of hours off from work to look for stores that had what I was visualizing her wearing. Driving around, I ended up with two names; Roberta’s Boutique and the Audacious Closet. Roberta’s was more elegant and Audacious more daring and loud.

That night, after I made love to Jean, I was holding her next to me. “Jean, you remember what you said a while ago? I haven’t decided, but … maybe. If I … we decide we want to, um, if.” I had to stop for a minute but continued, “Um, if you go on your adventure, if we decide for you to go, maybe we should be ready. Ah, can you get some time off from work tomorrow, maybe? Um, to go shopping? You and me?”

She slid back against me and held my hands against her breasts. “Yes, Miles, I’d like that a long lunch? Tomorrow?”

I was pretending I hadn’t decided, but I had. It might or might not happen this Friday, but I knew I was giving her permission to have sex. Jean had permission to cuckold me. I wanted her to. Everything we’d been doing for months was leading us to this. 

We met at Roberta’s, looked through their outfits, and then went to Audacious. There, she was attracted to one that was blue with large golden figures. It was sexy for sure, but yelling, look at me. Eventually, we got two outfits at Audacious and one at Roberta’s.

We got some lunch, but I couldn’t commit myself to saying okay for her adventures to happen this coming Friday. I wanted to, but couldn’t force the words out.

Thursday night, after finishing making love, she was on top of me, coming down after an almost simultaneous climax; when I could say, “Um, tomorrow, do you want to go on your adventure tomorrow? For real?

I’ve gotten it out; I hope I don’t regret it. I’ve started down the road—well, maybe not started. I’m in the last turn. Is this what I wanted or what Jean wanted? Who was leading whom? 

She rolled off me. “Tomorrow? You’re sure?” Then she snuggled closer, kissing me. 

No, I’m not. But it’s yes, anyway. I hope I don’t regret it.

Friday evening, I helped her bathe and shaved the last remnants of her hair on her pussy I put aloe lotion all over her, paying close attention to her pussy. 

When we were shopping at Audacious, Jean had let slip what the occasion was. Or maybe she did it deliberately. Anyway, the saleswoman insisted we buy a matching bra and panty set in the same blue. I got those for her and helped her dress. Just before she left, she turned around and went back into our bedroom to get the cock cage and help me put it on. She had to use ice to get it to fit the cage. She left with me, wearing only the cage. 

I was in the living room waiting, not watching the TV. My cock wanted to escape the cage, but couldn’t. My mind was picturing Jean at Monaco’s sitting there next to a well-dressed guy. He was holding her hand and kissing her, intent on her. What is she doing, feeling? I was both aroused by my thoughts and horrified by them.

I wanted her to enjoy what was happening, but the thought of her enjoying it was painful.

Finally, after an hour and a half, I broke, and I texted her. Jean, how is it going?

It was thirty minutes later that she texted me back. It’s going great; I’ve had two guys sit here and talk to me, and I’m enjoying myself. I‘m going to leave in a few, and I‘m hoping you’ll be ready for me. Ciao.

I’m still wondering what happened; did they kiss her? Did she kiss them back? If they danced, how close? This is agony, wondering. 

When she finally arrived home; she unlocked me after undressing. I wanted to … well, everything. We didn’t make it to the bedroom before fucking. This was the most intense sex we’d ever had. When we made it to the bed, we lay there, luxuriating in the afterglow.

“Tell me what happened, Jean. You said there were two guys?”

“Lee was the first one; I’d just gotten there when he approached me. I was sitting in the same corner you and I used our first time there. Um, it’s kind of private, right? Well, he asked if I was with someone, and I said no, and so he sat down. We talked for a while, and he’s in the toy industry from Cincinnati, he said. After a while, he moved next to me … ah, that was after we danced for a bit.”

She paused, before saying, “Umm, he kissed me, um, very passionate kisses. His arm was around me, and I felt the zipper on my dress. His hand was on my breasts, Miles. On my breasts. I could feel it everywhere. It felt so … erotic. God.”

She looked at me and smiled. ”I was a good girl, though. I sent him away.”

She sent him away? Immediately? Or did she wait and enjoy what he was doing?

“Anyway, after a bit, Julian came by. We danced a few times and talked. He’s from Atlanta, though I never found out what he does. That’s when I got your text. So, I closed it off and came home.

Okay, and what were you and Julian doing in the thirty minutes it took to respond? Was he holding your breast, or what? She was horny as hell when she got home, though. 

We did the same thing two weeks later. Her report back didn’t seem as complete, and I wondered if she was leaving stuff out. The stress was even higher, wondering what was happening. 

The third time, there was only one guy she talked about. 

When I asked her if she wanted to do it again, she agreed after some thought. 

Am I just suspicious that maybe she went further than she wanted to last time? Am I paranoid? Do I want to know? That is an important question.

As we prepared Jean to go out, I was more particular about everything. I made an appointment to have her hair done. Shaving her after her bath took longer. Somehow, this time seemed more critical, and instead of driving, she took a Lyft. 

When she left to go, she hugged me with her hand on my cock cage. She smiled and walked out.

I went into the living room and didn’t watch TV. I just sat there, feeling my cock in its cage for over an hour. Finally, I pulled my phone out and looked at it, thinking. I slowly entered. Jean, I need this to be over tonight. I want you to do it; pick someone and fuck them. When you come back; I want to know you’ve been with someone. I couldn’t say it to you, but it’s what I want. I want to see his cum on you, in you.

I sat looking at the text on my phone. I sat there for several minutes, and I hesitantly pushed send. It was done; I’d told Jean. 

When I started crying, I wasn’t sure if it was from the relief that I’d told Jean or the realization of what I’d told her to do. Both?

Is she going to answer me? What will she say if she does? The pain is overwhelming me. 

My phone finally pinged. New text. When I read the text, it was from Jean. Honey, yes, I got your text. I’m with Julian again; he was here and approached me again. Just a FYI, he’s black, and I’m bringing him home so you can watch. 

There are a couple of things. 1) I want you to undress me for him. 2) I want you to be the one who puts his cock in me the first time. Will you do that for me? I love you and thank you. Jean.

Oh, you don’t need to get dressed for us. 

She wants me to give her to Julian. God; can I do that? I’m going to see it happen. This is more than I wanted. But I’ll have evidence, for sure. God, he’s going to see my cage, too. 

I hesitated, then stripped the bed, replaced the sheets, and went back into the living room to pace, waiting. It seemed like hours, when a strange car drove onto the driveway. And a guy got out, opened the passenger, and let Jean out. 

I was practically having a nervous breakdown as Jean opened the door. Yes, he was black. When he stepped in, he seemed confident and didn’t smirk the way I expected him to. More realistically, I was afraid he might. Jean walked to me and hugged me, and I tried to hug her back.

“Miles, Julian, and I want to get right to why he’s here. Undress me here and lead us to our bedroom. 

I hesitantly walked to her, turned her around, and slowly pulled the zipper down. I knew the dress had to go over her head, so I pulled it up and over and placed it on a chair. 

God, she was beautiful. I could see her nipples jutting out and a slight blush on her neck and shoulders. I removed her shoes and stockings carefully. I’m envious of Julian; she’s his now. He gets to touch her, and I don’t.

I unfastened her bra, and her breasts were open for him to admire. Julian stepped up and touched her breasts with his fingertips, pinching her nipples. I watched her react; it was beautiful. She was pushing her breasts, her tits toward him, then she looked at me as if to say, “Get on with it.” 

I had to get behind her and pull her panties down and off. She was naked in front of him, with his hands on her tits. What they say about the contrast between a white woman and a black man when the woman is naked, like Jean, it's understated. Seeing Jean with Julian hands holding her tits was so erotic.

All I can think is that I’m giving her to him. I’m giving her to him to fuck. That’s what I wanted, right? I didn’t know it was going to be so hard. I’m going to put his cock in her.

I led Justin to our bedroom; where he undressed. He carefully placed Jean on the bed, right at the edge where his hands were on her tits, but his tongue was on her clit. “Yes, yes, Justin, yes, more, right there.” She tensed, screamed, and pulled his head to her pussy.”Oh, God, oh, God, Julian. Please.” Then she collapsed.

It’s so different watching and seeing Julian's black skin against Jean's fair skin. Plus, you can focus on what they are doing and what they are feeling. My cock is leaking cum. It hurts, but seeing Jean like this is what I wanted to see. There’s a whirlwind of emotions I’m feeling. I can’t stand it, but I have to. I have one more job to do. My final submission to the cuckold that’s in me. I still have to put Justin's cock in her. Hell.

He lifted her completely onto the bed, and he started kissing her all over.

“Miles, now, put his cock in me, now,” Jean said. "Please do it. I want to feel his cock while he's pushing inside of me. I want you to do it for me." Julian slowed the kisses and prepared to impale her, but hesitated.

I stepped up, took his cock, and guided it into her. When he took over, fucking her, I almost passed out. I stepped away as I saw his cock slip completely inside her. I heard her gasp and say, “Julian, it feels … your cock. I want you to cum in me. Don’t stop until you do.”

That’s how I became a helpful cuckold. The first time. I think. Maybe.