Cucked: The Blowjob Arrangement

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.

"Oh, Ethan went out, we have the place to ourselves tonight. You know what that means!" Jess couldn't help biting her lip and giving me a wink.

We fucked on the couch out in the open, our first sexual intimacy as official boyfriend and girlfriend, and our first since we'd had that fateful conversation. It still felt great, but my mind couldn't help but wander.

Sex had lost some of its sheen; it was hard to fully enjoy knowing she might have even had Ethan's cock in her mouth this morning. I wasn't completely devastated, but I was definitely feeling a nervous jealousy.

Even though I don't like admitting it, I was feeling protective over Jess in an old-fashioned caveman-brain type of way. She was mine, and I didn't like that this 'Ethan' got to have her lips on his shaft when he felt like it.

I tried to keep those thoughts out of my head as much as possible though, I had agreed to this arrangement, and I wanted to come off like a cool open-minded boyfriend to Jess.

We spent the night cuddled in each other's arms in bed, and I only awoke for a moment in the middle of the night when I heard what must have been Ethan coming back to the apartment. I squeezed Jess tighter as I fell back asleep.

The next time I woke up was to the sound of a knock on Jess' bedroom door.

After a couple of seconds, I heard Ethan's voice for the first time playfully shouting, "Heeeey Jess, I'll be waiting in my room, hurry up." In my grogginess it took me a moment to piece together what he clearly meant.

Jess turned to me and, unembarrassed, said, "Sorry, I'll be back in a bit!"

She was only wearing a pair of purple panties that showed off a little bit of cheek, and went to her clothes pile to throw something on. After stopping at a sweatshirt, I thought she'd look for a pair of pants, but instead she hopped out of the room, closing the door behind her and not looking back.

I didn't realize she did her 'work' without being fully clothed ever. It made me uncomfortable all over again that she was just going to not just be around Ethan without pants on, her underwear and part of her ass on display, but on top of that was doing it in an explicitly sexual scenario.

I had mentally prepared myself to accept that she'd be sucking cock from time to time, but her hopping out to do it in panties made my jealousy fire up again, and I really didn't think she'd just do it while I was staying over.

In her eyes, I had agreed to this and she probably didn't think that I had an issue with where or when it happened (to be fair, I avoided talking about their deal, and didn't tell her how envious it made me).

I wanted to tell her to not go, to wait until I had left the apartment, and that I wanted her wearing clothes when she did it. The sight of her ass should be for me and me alone, even if her mouth wasn't just mine. However, in that moment, I had froze.

I tried to justify it as much as I could to myself, if I was ok with her sucking Ethan's dick, which is a much larger step than her taking off her pants around another guy, so I shouldn't be that much more upset about it.

Still, I laid in her bed feeling like I was losing control: control of Jess and our relationship, control in my life. I stewed there, imagining her crouched over with her ass hanging out, licking and rubbing this guy's cock on her face with the same passion she carried for mine.

Then I started hearing the sounds through the apartment wall. There was the odd moan from Ethan, but unexpectedly, most of the sounds were coming from Jess. She was making excited squeals that got louder each time. Unfortunately, the blowjob seemed to go on forever. Ethan could last a lot longer than I could.

I hoped I could chalk this up to Jess not putting as much effort into blowing him as she did for me, but that thought seemed to contradict the sounds I could hear coming from the other room.

After close to twenty minutes, I heard Jess leaving Ethan's room as she came back to hers. She walked through the door with a huge smile on her face (to see me?), wiggling her hips as she pranced back into bed with me, and gave me a peck on the lips.

I didn't say anything so as to not rock the boat, and tried to push the thought out of my mind that those lips that had just pressed against mine were around her roommate's shaft not two minutes ago.

I blurted out without a thought, "Did you have fun?" to fill the awkward silence, using humour as a coping mechanism without actually wanting an answer.

Unfortunately, she gave a quick, "Uh, YEAH!"

We spent a couple of hours in Jess' bedroom hanging out -- not doing anything sexual, I just couldn't get myself in the mood after hearing what I heard. I had to leave before noon to meet up with a friend, and hoped I could quietly slip out without having to make eye contact with Ethan.

I didn't hear him around when I started to make a break for it, but he was quietly standing in the kitchen as I passed through it.

"Hey, I'm Ethan," he said, sticking his hand out for a handshake. He was bigger than I had pictured, and more fit than me. I got more than just some eye contact too, he was wearing a loose pair of shorts that gave me a glimpse of his bulge, which was also bigger than I had pictured.

My stomach sunk, and even after shaking his hand and leaving without saying anything, I was in an anxious funk for the rest of the day.

It wasn't long before I saw more of that bulge. That night, I was scrolling through social media, and saw a post from Jess. There was a recent trend where women would post selfies with their boyfriends' clothed dicks to show them off in a way that was just barely clean enough to not get taken down.

I'd seen a few racier influencers doing it, bragging about their man's impressive packages and winking or patting them in the photos. I'd also known Jess had a somewhat saucy account, and didn't shy away from posting photos of herself in bikinis that were sometimes pretty skimpy.

Still, I was surprised to see her taking part in this trend and posting a photo next to a huge semi-hard cock in a tight pair of briefs, trying to pull it to her face with one hand (a hand much smaller than the actual cock), and giving it a lick. It made me sick almost instantly, because I knew whose package it had to be. Friends commented that she was really lucky to have her boyfriend, and she didn't correct them at least.

I didn't know if I had any right to be upset about this; it was much less serious than actually blowing a guy, so if I was okay with the cocksucking, I had to be okay with this. She also wasn't revealing to the world that she had chosen some other guy's cock to show off, and let her friends think it was me.

Not that I'd even want to take part in this trend with her, I'd feel embarrassed doing it at my size. Worst of all though, this was the first visual evidence I'd had of the openness of our relationship: a real concrete reminder that my girlfriend was taking this cock and swallowing his cum more often than she did mine.

I decided to not say anything to Jess, because leaving things as is was only barely less humiliating than having to admit to her that I was jealous of this huge fucking cock, and having to have her take it down and explain why to everyone who asked.

I stayed with Jess later that week after a night out. We'd had a lot of fun, and each day since seeing that photo of her licking Ethan's dick through his underwear it had weighed on me a bit less.

Jess was in one of her super horny moods, and said she wanted to suck my cock really badly, but wanted to try something new; she wanted me to climb on top of her, her arms pinned down between my legs, and to play around with my cock, slapping it on her cheeks, and then facefuck her.

I tried doing this, but wasn't fully comfortable with it, and it must've felt awkward for her, so she told me to get off and happily went to town on my cock herself.

She still sucked dick with zeal, but I couldn't help getting in my own head about this. Where had she gotten the idea to try something like that? Had Ethan and her done that this morning? Was she so excited to do it because he had fucked her face well?

Now I had visions of him rubbing a massive erection on her face like twelve hours before I had been kissing it. She was excitedly sucking my cock now, but it felt like a consolation prize.

Thankfully, the next morning, Ethan had somewhere to be and couldn't spend his usual lengthy amount of time cumming in my girlfriend's mouth. Jess went out to start breakfast in the kitchen as he was finishing up in there, but knowing there wouldn't be a blowjob today, I didn't rush to join them.

After taking my time getting dressed, I stepped out of Jess' room, but didn't make any noise on purpose. Still in a petty jealous state, I peaked around the corner to the kitchen and thought I'd listen in on them out of morbid curiosity, even though the best case scenario was a boring conversation and the worst case scenario was something that would only humiliate me more.

"Yeah I'll miss it, but I'll just get it tomorrow" Jess said in what I knew was her playful flirty voice. "The least you can do is give it a kiss" Ethan retorted, and without skipping a beat, pulled his pants and boxers down far enough for his partly flaccid cock to flop out, which turned out to still be pretty far down.

It was the first time I'd actually seen it fully unclothed. Even just semi-hard it was still massive, easily longer than mine and twice as thick. My stomach sunk once again as I watched the scene unfold in slow motion. Jess started bending over without hesitation, her face getting closer to Ethan's thick dick.

I acted on instinct and started to walk out, thinking that I could bust Jess in the act and stop her from going through with a joking kiss. I rounded the corner just as her lips made contact with the head of the cock, and the image is still burned into my memory: her eyes closed, her mouth still pursed in a smile, but her lips firmly planted on another man's penis.

It happened faster in reality, and she pulled up immediately and her and Ethan said hi to me as he pulled his pants back up, as if nothing had happened.

I had to remind myself that what I saw as my interruption of a scandalous act was really just them doing something innocent that I had already agreed to being okay with. They acted like nothing was wrong because nothing actually was.

Even so, I my growing sense of humiliation flared up again. I didn't like seeing Jess' mouth actually touch this guy's cock, even though I already knew much worse was happening behind closed doors. Actually seeing it definitely made the reality of the situation sank in, and the jealousy I was experiencing burned inside.

It was all I thought of over the next couple of days until the next development. It seemed like the longer Jess and I dated, the more details and evidence of her cocksucking deal working their way into my life, and the closer to complete humiliation I got.

Every time I thought I was starting to be ok with a new development, an even more explicit embarrassing one would surface to smack me in the face. There had to be some endpoint to this, right? How bad could things possibly get before it plateaued?

Well, the most recent update happened through texting. Jess had mentioned that Ethan had a woman spending the night, a friend of hers. It made me smug knowing he wouldn't be getting anywhere near Jess the next morning, and that since we were meeting up later in the day, she'd be 100% mine.

The arrogance carried forward overnight, and the next morning I had the audacity to text her, "Too bad you missed out on a blowjob this morning eh?"

It was only a moment before I got her fast reply, "Actually I still blew him."

My heart sunk, not just because she had given him another blowjob but also that I'd had the gall to point it out, only to be issued this explicit correction.

"I thought he had a woman stay the night?" I typed, glad this embarrassing conversation was happening via text and not in person so Jess would be spared my panicked face.

"We both sucked his dick at the same time, it was fun!"

I was quick with my follow-up, "You had a threesome with Ethan?" Great, a new strain of jealousy I had to now live with, knowing my girlfriend was having threesomes with another guy instead of me.

"I mean I guess technically, if you go by the dictionary definition." I sat in silence with my phone in my hands, not knowing how to respond, until Jess must have sensed I was maybe upset, and she replied again.

"How about we both suck your big manly cock some time ;)"

It was a little patronizing, knowing how my cock actually compared to Ethan's, but I also wanted to 'get even' with him by having the same experience, I deserved it. We said we'd discuss it more that evening.

At Jess' place, we'd started making out in her bed, and that lead to the best sex we'd had in weeks. I had a renewed swagger knowing I was going to get to have a threesome, and have two women going at me at once.

I started to get back some of the overconfident attitude I had had before our relationship had entered this stretch. Jess went to shower afterward, and even though I was having a relatively good day, my new baseline level of jealousy still got the best of me, and I grabbed Jess' phone to look through. She didn't usually leave it laying around, and I was petty enough that I jumped at the opportunity.

I immediately went to the text conversations to see what she'd been texting to Ethan, but noticed a more recent conversation from earlier this afternoon with Anna, the friend that Ethan had spent the night with the day before -- the one that I'd have sucking my cock soon.

I casually opened the conversation, not expecting to find anything that would wreck me. I saw that Jess had mentioned wanting to do another cock double-teaming with Anna, maybe even with sex after (!), but this time with me.