Last weekend I confessed to my 25 year old girlfriend of 5 years, Emily, that I couldn't get the fantasy of her with another guy out of my head. I had told her once before, but it had been a few years ago- and back then it never really went anywhere. I could tell it was too much at the time. This time I was met with the same brand of reluctantance mixed with supportive that I had anticipated, but was pleasantly shocked to find her more receptive this time.

After a long talk with me trying to describe to her everything and us rehashing different aspects of our relationship, she reluctantantly and tentatively agreed to start exploring the fantasy with me. It was honestly quite surreal. In my head I had played out this very conversation hundreds of times, but in person it felt different, more intense. For one, she was more receptive than I anticipated- which isn't to say she was jumping at the idea to sleep with another guy right away- but just that she seemed to genuinely consider the possibility in a way I hadn't seriously expected.

The way Emily described it to me was that it wasn't like she was repulsed or shocked by the fantasy, but instead it just went against her idea of what a relationship was. At the same time though, she was willing to admit that she was a young woman who obviously found other men attractive (and who I might add it quite attractive herself), so that in principal it wasn't something crazy I was asking her to do.

We discussed next steps and boundaries, ways of safely exploring the idea, and agreed that communication and moving slowly were of the upmost importantance. It was beautiful to be so honest with her, but also terrifying. We talked about her maybe trying to flirt with other guys, maybe out at a bar or online. We talked about how she could maybe tell me about guys she found attractive, and also talked extensively about boundaries and how we were both feeling.

She then asked if there was anything I wanted to try then, in that moment, and I froze. Eventually I suggested she could tell me about her past. She had well, before we met, an adventurous time on the dating apps as a young hot freshman and sophomore in college away from home for the first time. She reluctantly agreed.

This is a brief story about what she told me (sorry in advance that it veers more toward a realistic portrayal than sexy embellishment):

"I mean one thing we could do is, or well, you could tell me about some of the guys before me," I told Emily, my voice nervous.

Emily shuffled on the couch, looking back towards me. "I mean, yeah. If that's what you want."

I could tell she was reluctant. She had told me before she wasn't really proud of her slutty college phase and that it is a mix of emotions for her, but I couldn't help it, I've always been so curious.

I moved over to caress her, a sudden nervousness and excitement taking over.

"Err- What do you want to know?" Emily asked awkwardly.

"I don't know," I admitted, before realizing that I would need to guide her a bit, that although I'm nervous and unsure, she must have been even more so. "How about I ask you things, and you just answer as best you can?"

Emily nodded, "Okay, yeah."

I moved closer to her, continuing to caress her while I think. "Ok, Ok. How about like, was there anyone who stands out, like someone you had really good sex with?" I asked, my heart pounding.

Emily seemed to squirm a bit, "I mean I don't know, not really? One guy was really good at going down on me..."

"But no like amazing sex?" I asked, slightly disappointed.

She shook her head, "I mean I think I just need like the emotional connection..." She paused looking at me.

"There was this one guy, err who I dated briefly before you who uh, it wasn't very good. I remember specifically that he had a really small dick," she explained.

"Oh?" I asked confused.

"Yeah, I think he's gay now," she continued before catching herself, "Okay sorry, that was kind of the opposite of what you asked."

"It was," I agreed, laughing. "Let me think... Okay, what about something else... Let's see, is there anything you did with another guy that we haven't done?"

"Let me think..." Emily starts, shifting closer into my arms. "I guess like public sex? We haven't really done that."

I felt myself stirring and pulled her closer, "Oh yeah? Like what?" I asked, rubbing against her.

"Err- in a car, or uhh a study room in the library..."

"A study room?" I asked between kisses against her neck, "Tell me about that"

"Mhm, okay," she purred, responding to either my touch or my clear excitement. "Well there was this guy from tinder who I had gone out with once, and he asked me to study. So I go to the library and we get a room..."

"Yeah?"

"And then it just kind of happened," she told me, as I continued to grab and embrace her.

"And was it good?" I growled.

"Yeah, it was pretty good."

I started to lose myself in the moment a bit, grabbing and clawing at her, as she continued to relay very minor and not particularly sexy details.

"Ok, anything else? Maybe a position we haven't done?" I asked, as that previous thread seemed to have died.

"Oh I don't know, a position? Well yeah I guess," Emily moaned softly. "There were some standing ones I don't think we've done. And spooning," She added. I got behind her in a spooning position as she said this.

"And you liked this one?"

"Mhm, yeah."

"I would you know... I just, I can't really reach," I admited, my mind a blur as I imagined her with another guy in that position.

"I think it's just like a height or angle thing..." Emily told me, skirting either intentionally or unintentionally around the other possible explanation... and that was it. I finished through my clothes and into my shorts, and collapsed next to her.

"Wow," Emily smiled at me.

"Sorry, I really wanted to have sex, I just..."

"No, it's okay, really, I'm glad you liked it... I'm sorry I was so bad at it, and we can always just have sex later."

"No you were great... And yeah, just give me a little bit," I told her, as my heart still thrummed.

We spent the next little bit decompressing, taking our mind off it. It wasn't long though before the thoughts swirling around in my head and recollections of what we had just done had me ready again.

That next time we made it to bed, in silence, an eagerness overtaking me as I kissed every inch of her body. Something possessed me as I undressed her, my mouth finding it's way to her...

"You said there was one guy who was good at going down on you?" I asked, as I went down on her.

"Mhm, yeah, there was," she told me, as she moaned softly, "there was one guy who would play with my nipples a lot..."

"Yeah?" I asked, lifting my head slightly before returning.

"Yeah. I didn't really like it though... He would leave them like bruised and stuff. Oh- Oh, right there baby, just like that..." Emily's words turned into moans as she finished.

I pulled myself up to meet her eyes, almost shaking as I got ready to enter her.

"We don't usually have sex multiple times a night, err- that's another thing," she said.

"No, not usually..." I admitted, lining myself up, gasping as I slide inside. "But with other guys? Whats the most, err in a night?"

"I don't know, 2 or 3 times?" She answered, unsure.

"Yeah? Tell me about that," I urged, quickly losing myself in the fantasy again.

"I don't know, there was just this one guy who was just a lot... Like grabbing me in the middle of the night, I don't even know if I liked it honestly."

"Oh," I gasped, a bit disappointed, but also still deeply taken by the idea.

"He had a big dick though," Emily announced matter of factly. Testing the waters maybe.

At her casual announcement, I found my blood racing, "Yeah?" I stammered, trying desperately to stay in control.

Emily nodded, "Yeah, almost too big, like it would kind of hurt," she admitted.

I had to pull myself from her to stop from finishing. I switched to kissing her body and then to my fingers.

"How many times with him?" I asked.

"I don't know, like sex? 10? 15 maybe," she told me.

"It was good though?"

"I guess it was, yes... I mean he was kind of an asshole," she explained.

I couldn't help it, I entered her again. "Was he attractive?" I asked, desperately.

"Yeah... He was handsome."

And that was it for me, as the thought of my Emily, my sweet gorgeous girlfriend, with the big dicked asshole fucking her 3 times in a night, swirled across every inch of my mind.

Afterwards was a bit intense, but mostly positive I think. We talked a bit more about it, and how we both felt. She seemed both a bit torn, but also a part of her was definitely excited. She on her own suggested that she could try writing some sexy stories for me.

Anyways, that's where we are at now, cautious, but optimistic about the future.