I started dating Jess the year after graduating from college. She had approached me at a bar and was the one who initiated the flirting. That was part of what first attracted me to her; she was forward and open about what she wanted, and Jess made it clear from our first conversation that that included wanting me.
That first night we went back to my place and had the most frenzied passionate sex I'd ever had up to that point in my life. She was really clearly horny before we had even made it back to my apartment, whispering things into my ear the whole night, like, "I fucking NEED your cock in my mouth," until we eventually gave up on pretense and hurriedly grabbed the first cab we could see outside.
Rushing back to my bedroom while stripping layers, we flopped down onto my bed while making out in an intense primal way, Jess in a classy black thong and I in a pair of tight boxer shorts that didn't leave TOO much to the imagination.
She quickly pulled herself south, burying her face in my bulge before yelping, "Off!" We were on the same page, and both pulled off my underwear so Jess could finally get what she wanted.
She played around with my cock, rubbing it on her face and lovingly kissing it for as long as her restraint let her before diving onto it mouth-first, but I wasn't complaining.
My dick wasn't a bad one by any means, but at slightly below average length and thickness, it wasn't too often that I was with a woman who was such a rabid fan of it. I could only handle 10 seconds of Jess' cocksucking before I had to push her off of me because I didn't want to blow my load before we started fucking, although I didn't last much longer after getting in her anyways.
We slept very well that night, just a deep satisfied slumber despite the butterflies in my stomach she was giving me. Jess left that morning because she said she had things to take care of at her apartment, but we agreed to meet up again soon for a proper date.
Over the next few weeks, we saw each other every day or two, with her spending the night at my place at least a few times each week. I couldn't get enough of Jess, just being around her felt liberating. She was a true free spirit, and spending time together gave me an energy.
Everything was smooth with our burgeoning relationship until one night spent at my apartment. Jess was blowing me with her usual zest and very quickly, despite holding back with all my willpower, I blasted cum down her throat.
I sometimes go on auto-pilot and will say things without fully thinking them through, and in my post-blast bliss, I mentioned that I didn't know how I was enough to satiate her.
The mood came to a bit of a grinding halt and an awkward tension filled the bed. Thus began an uncomfortable conversation about 'what we were' and exclusivity. These talks are usually only ever NOT uncomfortable when both parties were on the same page and had already assumed things were closed between them.
And it's not that Jess and I weren't totally on the same page; I admitted that even though I hadn't been with anyone else in the last couple weeks, I was still on the apps.
It was more Jess' response that made things uncomfortable.
"I definitely want to move to things being romantically exclusive. I really like you and only want to date you," -- so far so good.
"...but I guess I don't think I can be in a completely closed relationship sexually..."
"Have you been sleeping with anyone else?" I asked, wanting to know the answer but not wanting to at the same time.
"Well, no, at least not having sex with anyone since I met you. It might sound silly but I made an agreement with my roommate a while ago that I'd suck his cock every morning."
I was flipping back and forth between the disheartening feeling in the pit of my stomach, and thinking about how I'd never actually stayed at her apartment before this. I swallowed and asked what was on my mind.
"Have you been... doing it the last few weeks?" She didn't hesitate to give a straight answer.
"Well not every single day, but most days. Sometimes our schedules don't match up. Or sometimes he doesn't feel like it." But she always does? I think Jess sensed my racing mind and came out to find a compromise.
"What if we keep the deal going, but that's it? I won't have sex or do anything with anyone else, just you and me."
I tried to make myself go through the pros and cons of the decision, forecasting ahead to imagine what I'd feel like being in this relationship months from now, a year from now, multiple years from now.
Instead, I again auto-piloted to, "Okay." Without truly thinking it through, I'd just locked into this situation I didn't want to be in, and it just took me two syllables. To be fair, what else was I going to do?
Being with Jess was the happiest I'd ever been while dating someone; spending time together was amazing, the sex was amazing -- why would I want that to end?
And it wasn't a full-on 'open' relationship. It was just one guy, and they weren't even fucking. And who even knows how much longer they'd be living together with this deal in place. I could put up with that.
I didn't see Jess in person for the next few days. I was too nervous to directly address the elephant in the text conversation, but I danced around it in my morbid curiosity.
Texting, "Hey, whatcha doin?" in the morning, and then dreading potential responses.
Later I was met with, "Taking care of business, you know how it is," which could mean anything.
Finally, Jess asked me to come over to watch a movie and spend the night at her apartment. I had guessed that she hadn't invited me over before discussing our relationship status to avoid her 'deal' coming up in conversation. I was nervous to go, building up horrible 'what if' scenarios in my head until I got there.
"Where's your roommate?" I asked, using every ounce of social grace available to me to play it as cool as humanly possible.
