The night of drinking and dares with Jess, Ethan, and his friend marked another big transition for the apartment along a few different dimensions.
First, the intense humiliation of running through the building in a pair of Jess' panties, followed by standing around in them while she sucked two thick cocks right in front of me, broke some kind of shame barrier in my head.
Now I still would get a rush of humiliation from doing something like that again, but I wasn't as averse to it. I'd even started getting turned on a little from the idea of being embarrassed in that way.
Jess would go further in pushing me out of my comfort zone for her own pleasure, and I started giving in more often.
I was now wearing her panties almost every day, at her request. She'd also ask me to do things for her that would get me around the apartment wearing nothing but her underwear.
A request like "Can you grab me some water from the kitchen?" while we were hanging out in bed without clothes on would see me walking through our apartment in a pair of red lacy boyshorts, regardless of if Ethan was around.
If anything, I liked having these excuses to be nearly nude around him. Ethan never failed to swat my bottom if he saw my round little buns in a pair of Jess' panties, and honestly, I enjoyed the positive attention. The sharp smack from his big hands didn't hurt things, either.
I wasn't sure if it came from a place of him liking me in panties, the image reminded him of Jess and turned him on, or if it was just fun between bros in his mind.
Secondly, that night seemed to bring Jess and Ethan closer together as well. The everyday sexual tension in our apartment had ramped up since then, and there was almost always a horny energy between us all, but this was especially true between the other two.
I'd routinely come home to see Jess sucking the hell out of Ethan's huge cock in common areas. He'd occasionally interrupt our conversations or date nights at home to start frenetically making out with Jess in front of me.
One time, Ethan even came into our room while we were having sex after he must have heard the sounds Jess and I were making. She was riding me, but he came over, shirtless, already hard cock sticking out of his pants, pulled her off of me, and holding her up with one arm, used his other hand to insert his erection into Jess' pussy.
Don't get me wrong, I still would rather have been fucking Jess, but that experience turned me on in surprising ways. Having this real man literally take my girlfriend from me by pulling her off of me with his strength and fucking her in her arms with my little dick now exposed was exhilarating.
I still felt pangs of jealousy during acts like these, but I'd be lying if I said that masturbating to this happening a couple feet away from me didn't make me cum harder than I usually would.
Following the dare I vetoed from that drunken night, Jess hadn't let up in trying to initiate sexual contact between Ethan and I. If anything, she'd been trying even harder, maybe sensing my resignation that I knew she'd eventually get what she wanted.
It was hard to say no to her when this was something that was very visibly making her so happy, and if I'm being honest, also made our sex life together better as well.
One morning, Ethan had come into our bedroom while Jess and I were still lazing around in bed to claim his daily blowjob. This was mostly a formality now; Jess would often suck him off more than once per day, or blow him earlier in the day and fuck him later.
This morning I was naked in our bed, but didn't really mind Ethan seeing me completelyl nude any more, just as he didn't mind me seeing him in the buff (I know, I know, that's different).
Ethan stepped up to the bed already sporting a half-boner and pointed to it without speaking a word. Jess pulled out of her position cuddling me and dove on the hard cock with glee.
After a solid thirty seconds of sucking and licking, Jess slyly told me to "Come over here!" Ethan's cock was how fully hard, a really impressive piece she held up in one hand with some effort.
"I don't want to suck it," I said, hesitantly climbing closer to Jess and the cock.
"I know, I just want to try something," Jess giggled, clearly having some impish little trick planned. I brought my head closer to hers but still out of range of Ethan's massive member.
Jess then quickly swung Ethan's cock from the base, slapping it into my face, and burst out laughing, and Ethan even chuckled a bit. I thought I was far enough away from the penis, but it was longer than I thought, especially up close.
My mouth dropped open out of shock and I jumped back, yelping "Ow!" It was an instinctive reaction, but even though I wasn't really in pain, I was surprised by the hit.
His cock was WAY heavier than I expected; the thump to the side of my face actually shook me. Even after the events of the past few months, it was also weirdly one of the more emasculating things that had happened to me - this was the most literal version of Ethan proving he was more of a man than I was, and it even hurt a little.
I'd come into contact with this cock before, but hadn't had it shoved in my face before, and definitely not in a context this humiliating. Jess was clearly enjoying her little prank.
"Oh my god, it actually left a mark on your face!" she laughed. "Why don't you cock slap Ethan back for revenge?" This made her grin even more.
Unfortunately for Jess, I knew Ethan wouldn't be down for this, but he didn't have to say anything because I sheepishly backed off anyway. There was no way I was going to emasculate myself so directly by attempting to hurt someone back with this little dick.
Still, Jess took her first step toward getting me into contact with her favourite cock. I was really embarrassed in the moment, but seeing my face in the mirror later and still having the print from his dick visible on my cheek turned me on in retrospect.
A small part of me wanted Ethan to make me his totally the way he did with Jess. The kind of attention that comes with being taken like that was very desirable to me.
The cock slap also kickstarted acts where Ethan would dominate me directly, instead of just indirectly through Jess or with her around. For instance, one time I was walking through the apartment to grab a snack for Jess, who was waiting back in our bedroom.
I was in the kitchen in nothing but a dark purple g-string of Jess'. I heard Ethan moving around behind me and wondered if he had seen me. Suddenly, I got pushed down, now bent over the counter.
With my ass pointing out, Ethan gave it a harder spank than he had before, and my dick almost instantly shot up behind the purple fabric.