I can’t remember now when I admitted to my then-girlfriend that I was interested in her cuckolding me. The desire preceded the relationship, and it has stayed with me in the years since that relationship ended.
She knew, though, before she left for a college reunion the last fall we were together. As I remember it now, I feel like she must have noticed a spark when she mentioned looking forward to seeing all of her old friends. The college was a plane trip away from where we lived, and this reunion was her five-year, so most of her friends were still unattached and living interesting lives in the big city she had left. She missed them; she would find a way to go up for the weekend and see everyone she could, staying in her friend’s empty apartment.
One of those friends, Luke (for our story, but his real name will never leave my mind), had not attended the school, but came to know that my girlfriend would be traveling to the city for the weekend. I’m sure I had heard about Luke beforehand, but always in the context of some other guy friends of hers. Maybe they were buddies from her post-college job or the bar they all went to.
One night, a couple of weeks before the trip, my girlfriend called over from the other room and told me to “make an angry face” while she pointed her phone in my direction. The picture was for Luke, she said, who had teasingly suggested she bring along some lingerie for the reunion weekend. As I recall, I didn’t have the faintest idea that their text conversation might have taken that turn, and I’m sure the blood ran from my face and just as sure where it went.
My girlfriend thought it was funny, and I convinced myself that it was just an improbable joke, almost certainly not having to do with my fantasy. But I didn’t want to let the opportunity pass to explore it either.
That night I asked her in bed whether she might break away from the college group and get to see Luke and her buddies. She touched me while she asked if that was something I wanted. I touched her as I asked her to describe Luke to me. He is extremely well-built, funny, just never single at the right time, one of the ones who got away.
Before I came, I was desperate to outline the breadth of my fantasy again, reminding her that she had every right to see whomever—and do whatever—she liked, at home or while on a trip, far away from everyone we knew.
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She left for the reunion. Luke had been called away on business for the weekend she was going, so our bedroom talk had softened. The realization, though, that she would consider an affair, engaging me in the fantasy with a particular name—a particular person—had electrified our relationship and dominated my thoughts.
She went to the cocktail parties and the football game, sending back social media pictures of her group of friends in their team’s colors at each of the different events. Sunday morning, she went out with her girlfriends to brunch. Between pitchers of mimosas, she called me and put me on the phone with her old friends, who interviewed me. Even after a couple of years of dating, I had never met them, so I got questions about my intentions with my girlfriend and plans for when we might fly to see this friend or that friend.
Eventually my girlfriend took the phone back and walked away from their table. She asked me almost immediately, “Were you serious about the hall pass? Luke is coming back a day early.”
I was stunned. I managed to say yes and offer her encouragement without, I think, making myself sound desperate that she go through with it. I also don’t remember ever using the phrase “hall pass.” She had spent time with the thought, rationalizing it.
She called later that afternoon to say that she had made plans to see Luke and her other buddies, and that she had made Luke aware of the fact that she was staying at her friend’s empty apartment, all alone.
The next time I heard from her was the following morning. She texted to let me know she made it to the airport, that she had had fun the night before and that she had a story for me when she got home.
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I still don’t know if Luke was aware of my fantasy or not. My girlfriend always found ways of skirting the point, keeping private some element of her interactions with him.
I do know that by the time he arrived at the apartment, after he had been out with her and their buddies to the bar, meeting her at the door where she greeted him in a sweatshirt and sheer panties, he had explained that he had a girlfriend. As they kissed and she began to remove his clothes, pulling him to the couch, he explained that he would have to draw a line—somewhere—short of sex.
When my girlfriend told me my story, that Monday night, I am convinced that she told it in episodes. Each one slightly more damning than the previous, in case I lost my permissive resolve. I held up, so the details continued to grow more vivid.
She always denied having sex with him, but what began as making out on the couch eventually moved to the bedroom. First with clothes, and then without them. She touched me as she asked, “Are you happy that I touched him like this? He was very happy.” My girlfriend described Luke’s toned body, naked beside her, and the sweetness of his kisses.
They played with each other all night, not falling asleep until five in the morning. Before he went to work, they shared a lingering kiss at the door. He left his wallet and had to come back a half hour later. She told me, “the last kiss was my favorite part of the whole trip.”
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She seemed to feel different to my touch that night, although I’m sure in my mind I wanted her to. I am guilty of looking at her email once to search for Luke’s name, finding a conversation they had about a “shower party” (her quotes) a few days after she came home. She did love to make love in the shower.
My girlfriend would ask me occasionally what I wanted to do about the experience. I imagined with her, for her, a weekend where my apartment would be empty so that Luke might come to our town, perhaps on business. I could be gone whenever she liked, I said.
She wondered if I might want to participate, suspecting that I would want to enjoy Luke alongside her. She never articulated that specifically, but I could tell she always wondered what else could possibly motivate such a fantasy.
Really, though, her night with Luke helped me to see it more clearly than ever. I wanted only for her to feel in control, untethered from me and not especially concerned either. I wanted her to have sex or not have it, with a man or with a woman, to tell her friends or Luke or not to tell them. It didn’t matter to me what came of her decisions, only that she was making them.
I was happy to wait at home to find out my fate; to learn from the person in control just what had happened to her and to us and to me. I begged to know.
restlesslibido: Tonight’s the auction. Everyone going up on the block is supposed to wear pink, in line with the charity’s branding. This is all the pink she has. The t-shirt is from a friend’s bachelorette party. It’s soft and baggy, with the word squad written across the front in silver letters. The miniskirt is something she bought herself on impulse not long after we first started dating. She wore it under a long overcoat and made sure to arrive after me, so she could watch me watch her take her jacket off. The last time she wore it was out to drinks with some people from my work, spending the entire evening chatting with my co-workers and remaining torturously out of reach. That is, until, half-mad with lust, I followed her into the candle-lit bathroom and took her against the sink. That was a year ago. Since then, it has hung, forlorn and forgotten, in the back of her closet. So what do you think? she says and she does a turn. The twinkle in her eye tells me she knows exactly what I think. It’s such a shame you won’t be able to make it, she adds, giving me a pout. Unavoidable work obligation. I grit my teeth. It is, I say, but I’m sure you’ll have a wonderful time anyway. And raise lots of money, she says. Undoubtedly, I say. She gives me a chaste peck on the cheek, then turns to go. Don’t wait up, she says.
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She knows. She can tell. She knows that you love the idea that she might have cheated on you. She’s known for years. Now, though, she might have done it. She might have fucked someone else. She might have let him cum in her pussy. You want to find out, don’t you?
You crawl into the bed. She spread her legs. You crawl closer. You run your fingers over the delicate lace of her panties. They’re wet and warm. It could just be her juices, though. She could just be soaked with desire.
“Pull them aside,” she says. “See if I let another man cum in my married pussy.”
You pull aside her panties. Her pussy is a mess. It’s a sticky, wet mess. It’s not thick and creamy like cum, though. You’re not sure if she cheated, if she fucked someone else. You look up and see a smile on her face.
“Taste it,” she says. “Use your tongue to see if I fucked someone else, if I cuckolded you.”
You move just a little closer. The smell of sex fills your nose. She fucked someone else. She must have. There’s only one way to know for sure, though. You have to taste her.
“Go ahead,” she says. “See if I made your fantasy come true.”
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You extend your tongue. You run it over her pussy lips. You take the fluid onto your tongue. It’s salty. It’s bitter. It’s gross. It’s cum. It’s another man’s cum. It’s absolutely another man’s cum.
“It’s good, isn’t it?” she asks.
You look up at her and nod.
“I’ve tasted it before too,” she says. “In fact, I swallowed his cum just a few days ago. I went to his house while you were at work. I got on my knees for him. I sucked his cock. I swallowed his thick load. I did it all while you were working hard to pay our bills.”
You’re hard as a rock.
“Can I fuck you?” you ask.
She smiles and runs her fingers through your hair. “Of course you can. You work so hard for me, you deserve to fuck me. I need you to clean my pussy first, though. Clean up every drop.”
You can’t imagine anything hotter. You push your tongue deep into her pussy. Your cock throbs as you close your eyes and let the pleasure of being a cuckold wash over you.
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