My Boyfriend Asked Me To Fulfill A Very Controversial Fantasy (Here’s What Happened When I Did)

It should be known that my boyfriend is not a “controversial sex fantasy” kind of guy. He’s a “good guy” — (and maybe all “good guys” are also “controversial sex fantasy” kind of guys, I don’t know) — he’s the one you bring home to your parents and you don’t even pump up in the car ride there because you know, without fail, he’s going to make a good impression. Jake is affable, responsible and loyal. I always felt safe with him, which was why I was pressing him to hear about his deep, dark, sexual desires.

I knew, whatever they were, I’d feel comfortable enough with him that we could try it.

I remember the first time I met Richard, Jake’s boss, at last year’s Christmas party. He was younger than I thought he would be. In his early 40s with a great body, perfectly styled hair with just a hint of grey. We hit it off immediately. He was intimidating, but easy to like. I could see why Jake looked up to him. Jake was always telling me stories about Richard.

They met in grad school when Richard consulted on Jake’s thesis. They hit it off and he’s been sort of a mentor to Jake ever since, that’s actually what made him come to New York, to work with Richard. We had long since started our life together, and Richard was a welcome part of it. He and his wife had come over for a lot of intimate dinner parties that turned into very late nights over opened bottles of Chianti.

One night while I was clearing the dishes in the sink and Richard was still sitting in the living room Jake came up from behind me and nuzzled my neck, wrapping his arms around me like he always does, pressing his hips into me in a way that made me glad it was almost time for us to be alone. “Tonight’s going really well, don’t you think?” He asked me. “Yeah, babe. Of course.” Kathryn, Richard’s wife, was MIA for the evening. Down with a flu or cold of some sort. Richard seemed glad to be away for the night.

“Do you ever think about Richard? … Do you find him attractive?” Jake had pulled away from behind me and we were now facing each other. I sort of laughed and said, “Well….yeah. Sure. He’s a very attractive man.” That’s the thing about Jake. I always knew I could be totally honest with him.

And honestly, I had thought about Richard. What young woman doesn’t fantasize about the powerful, confident, worldly man in her life? He was like a younger, fitter Javier Bardem. A girl could do worse.

“Yeah, I think he’s sexy, honestly” I told Jake. “Distinguished, like you’ll be one day.”

“Interesting,” Jake said with a smirk on his face. “That’s really interesting.”

“Why do you ask? You jealous?” I teased.

“Not at all actually. I think it’s kind of hot.”

“It’s hot that I have a crush on your boss?”

He leaned into me, his 5 o’clock shadow scratching me as he breathed into my neck, “Remember when you asked me if I had any special fantasies?”

And then I knew where he was going with this, and I thought my immediate reaction would be hurt — that he was okay with me having sex with another guy — but it wasn’t. It was an overwhelming feeling of being turned on, of immediate wanting. Jake was saying that not only was my little crush okay, that it turned him on to think about his boss and I being together.

“I want Richard to fuck you. And I want to watch.”

He knew it turned me on when he talked like this, when he took charge. I always felt like that made me his. And, honestly, it was kinda sweet that he wanted to get his boss laid.

I looked at him and smiled. “Okay,” I said. “I’m down.”

As I turned around and headed towards the living room Jake slapped me on my ass. “Good girl.”

Richard was sitting on the couch finishing a glass of wine when we came back in the room. He had put on some light music.

I rolled my eyes a bit, he must have known this was going to happen. They’d cooked up this scheme over after-work drinks, to be sure. The idea excited me, that they’d spent a few hours over scotches talking about me, trying to figure out how to get Richard in my pants.

It made me feel a bit braver about the whole thing, I wasn’t going to make an idiot out of myself. I sat next to Richard and immediately propped my legs up in his lap and cozied into him. I went to the old standby, the thing men love talking about (how much of a martyr they are). “Jakes been telling me how hard you’ve been working, poor thing.”

It worked, he launched into a story about ball-buster clients and late nights at the office. I rubbed the scruff on the back of his head while he talked, goading him into telling me more, into opening up to me, but never going too far, letting him think he was the one seducing me.

As he talked about work he rested his arm on my leg, rubbing it nonchalantly while talking, as if the whole thing was totally normal. I looked over, interested in Jake’s reaction. He made eye contact with me and winked. This was exactly what he wanted but I knew he wouldn’t be satisfied until one of us made a real move.

I shifted my legs in his lap, making sure one of them ran over his cock (I could feel it now) and that the movement shifted my dress up, so my pink lace panties were now visible to him. His eyes moved from my legs to my panties to my lips, and I smiled.

In a movement so quick I didn’t immediately register what was happening, he had pulled me on top of him, slid his hands into my panties, and wrapped his lips around my neck, kissing me greedily. I gasped into his ear as I felt his hands, sadly more expertly than Jakes, stimulate all the right places inside of me.

I lifted my head and kissed Richard full on on the mouth. He tasted like wine and like peppermint, as if he’d popped one when we were in the other room, in preparation. I thought of all the times I’d seen him and thought about what a sexy older man he was and now this was finally happening, and with Jake’s blessing!

Richard pulled my panties down and slid his cock deep inside me. He was larger than I anticipated and much larger than Jake so I let out a surprised moan.

“Jake is a very good employee,” Richard said, his voice lower and hoarser than usual. “I’ll make sure he gets an extra bonus this year for letting me fuck his girl’s tight little body.”

I looked over at Jake, he looked barely able to control himself. Richard was laying over me, fucking me, staring at me as if he couldn’t believe his luck. I felt like a goddess. While he fucked me he pulled the hand that had been inside me up over my face. Obligingly I opened my mouth and tasted myself on him, swirling my tongue over each of his fingers.

His speed increased, he was losing it. “I’m going to cum inside your girlfriend,” he announced to Jake. I felt myself tightening around Richard, so full of pleasure — not only from his cock and the skill with which he laid into me but from the forbidden feeling of fucking my boyfriend’s boss in front of him, of doing something so deliciously bad.

When he came, I felt it deep inside me. I loved it. I was desired not only by my hot, good boyfriend but by his incredibly sexy boss as well.

After Richard left Jake and I retreated to our bedroom, laying naked on the sheets in silence for a moment. Oh fuck, I thought. What would happen now? Would our relationship be able to handle what just happened? Would Jake regret this night?

“Babe, come here,” Jake pulled me closer to him. “You’re fucking incredible. Do you realize that?”

“So…everything’s okay?” I asked. “This was exactly what you wanted? You’re not going to regret this tomorrow? It’s not going to jeopardize anything at work will it?” I knew Jake had enjoyed himself in the moment but I needed to know everything would be okay, that we would be okay.

He kissed me on my forehead and laughed. “No. If anything this just made work a whole lot better.” Thought Catalog Logo Mark