The Girl Is Trouble

Darren:

Life with Jess in it was nothing if not interesting. Our sex life was amazing. And hearing about her other exploits were fuel for the fire. Of course there was Jacen, but there were others. Jess was insatiable and that led her to be open to whatever came up. Sometimes, that included times went she was out with me. For example, there was one time we were out together eating out at the local Asian fusion restaurant and she went to the bathroom. She was gone for some time and the next thing I know I get a text from Jess.

Jess: Sorry I disappeared. Pay our bill then come pick me up in the back alley.

I did as she asked. I knew better than to question. I couldn't find our waiter, but the manager was happy to get me our check.

When I found Jess I understood what had happened. She obviously had sex with someone. She was quite disheveled. She had me meet her out back to save me the embarrassment.

"I figured this would be better. I assumed you didn't want to be humiliated in public. But now that I say it out loud, maybe I was wrong," she said.

She completely saw right through me.

"So do you want to tell me about it?" I asked as I helped her into the car.

"I fucked our waiter. He'd been making eyes at me all evening," she smiled.

I had noticed the glances between the two of them, so I wasn't too surprised. Still I didn't think he was her type. He was short, lean. Asian, looked to be of a Japanese descent, but I wasn't an expert on such things. I did notice a tattoo sleeve on his right arm peek out from under his dress shirt.

"I see. How was it?" I asked, both curious and a bit annoyed. Then I felt shame as I realized my annoyance wasn't from her doing it but that I missed an opportunity to watch it.

"He scratched an itch, but to be honest it just got me more itchy."

"So not a repeat candidate?"

"Oh, I didn't say that. He was quite good. That uniform hid a tight little package that was very well-trained."

"So was he well-hung?"

"Oh, I wouldn't say that. His body was really nice, but his dick wasn't all that. Actually, it probably wasn't bigger than yours."

I guess most of my fantasies surrounded her with a guy better hung than me. The idea that she'd have sex with someone the same size or smaller, and be willing to go again, never entered my mind before now.

"What would disqualify someone from a repeat performance with you?"

"Oh quite a few things. For instance, if they failed to get me off. If they were an asshole. If they got out of line at all. If they knew about you and were a jerk to you. I mean there's a line between playful humiliation that we were part of and denigrating you."

"Wow, ok."

"You didn't think that I would let you be put down, did you?"

"I guess I hadn't thought about it much. I mean, it's nice to hear but that seems like such an odd situation to consider."

"I know this may be weird for me to say after I just left you to fuck another man, but I've really fallen in love with you. The idea that you have completely taken in stride this situation and your focus this entire time has been on my pleasure- it's really amazing to have someone like you in my life."

"It IS weird, Jess, but I really love you too. It's exciting what you do and to be part of it is pretty cool. Plus, I get to be with an amazing lover while we build something more than just about sex."

"I have to ask, is there something more I can do for you? Is there something you might be into exploring so that you get more out of it?"

"Well, I mentioned before that I think I'd like to watch at some point. I know that's weird, right?"

"Not really. Apparently it's a pretty common kink. But regarding that, there's something I need to share with you that I was unsure of. Jacen is asking about you. He says he wants to meet you."

"Oh?"

"Yeah. I'm not sure what he's hoping to get out of it, maybe just sizing you up. I don't think it's going to be a problem. It's not like I expect him to harm you or anything. As I said before, I think he might actually be getting a little jealous of you which would be very weird for what he and I have. If you are open to it, I can set something up."

"Wow, ok. Sure."

"Is there anything else?"

I thought long and hard about what I would say to her. I was deeply in love with Jess and her honesty and willingness to explore my hidden kinks gave me a level of trust I didn't think I could have with a woman. So I opened up. I took a risk and shared my most shameful desires.

"Well, and I know this might seem weird too, but you've told me Jacen and some of your other lovers are....bigger than me. I wouldn't...hate... you pointing that out more. Comparing me unfavorably, if you know what I'm saying."

"Oh. You like that, huh? For the record, I don't think of you as all that small Darren. And I've certainly had sex with guys who have great big cocks that had no idea or interest in putting it to good use. But yeah you're much smaller than a guy like Jacen. Is it hotter for me to fuck a guy with a great big cock that puts yours to shame or someone like our waiter who might even have been smaller than you? I mean big cocks make sense for me to want to fuck in comparison to you, but why would I bother with someone equal in size or even smaller, right?"

"It suggests I'm not a good lover if you're having sex or considering having sex more than once with someone the same or smaller. Or at least good enough to fully satisfy you. Ok, yeah, that's hot too."

"So you want a little light humiliation in comparing you, size or performance-wise, to my other lovers. Is that just between us, or would you want it in front of them?"

She knows. Does this turn her on too? "Oh, god."

She notices how hard I've gotten.

"So that would turn you on. OK. But if I do it in front of them, you know that they may riff on it too."

There was something I don't know that I knew was there inside me that was going off like fireworks in my gut when I thought of this. My girlfriend screwing another guy and both of them humiliating me with their words. "That... that'd be ok."

She looked me in the eyes and it felt like she was staring into my soul. "Ok, noted. It was hot for me when you ate me out after I'd been with Jacen. Is that something you'd want to do more of?"

The was a long pause as I tried to form my thoughts on this. "Yes. Anytime, you want it."

"What if I made you do it in front of another guy? A FRESH creampie?"

I felt completely flush. "Oh yeah. Do that."

"You've not been a submissive lover with me. Is that part of this for you? Do you want to be treated that way with me and my lovers?"

"I think I'd like to explore that."

"Oh baby, we're going to have so much fun. But listen, if things get too intense or too hurtful, you've got to tell me, ok?"

"Sure. But probably not in the moment. If I feel I have an out, it probably wouldn't feel the same."

"Good point."