With a gentle tug, I too was guided forward, crawling a bit forward until I felt the dildo slip from my ass, leaving me feeling that familiar empty sensation. In addition to having been allowed orgasm, my victory in this challenge seemed to put me above Jess in a sissy hierarchy. I was told to lie down on my back.

“Jess,” Martin commanded, “use your mouth and tongue to clean up Crissy as best you can, then slurp up the little mess she’s made on the floor.”

From my position, I couldn’t see very much of her, especially as I was blocked by the face breasts heavy on my chest as she moved down between my legs. I did moan, however, when I felt her mouth on me. Her tongue was warm and rough as she dragged it over my tight balls. She did her best, working around the cage and, in the end, took the whole of my trapped self into her mouth, slurping and sucking. The cage kept me from feeling too much direct sensation, but I did feel the wetness and warmth. 

“Plug her again, Jess, and then yourself,” Liam instructed. 

Jess was provided with lubricant and fresh plugs. I didn’t see the one chosen for me beforehand, but I felt it as she pushed and twisted it inside me, and I was sure it was a step larger than the one that had been removed. I was able to see Jess’s expression as she guided the matching toy inside herself and her face displayed a mirror of what I had felt. Before she moved on, she helped me back into my panties and then reached out a hand to help me back upright. 

The men were taking their seats again, ready to resume their game now that the floor show was ending for now. I watched and listened as Martin instructed Jess on her next task and service and I felt the spark of recognition as he described what I had done under the table at the last gathering. Her mouth was to become a second Dealer’s chip. 

I took over as waitress and bartender, watching what I could see of her under the table, making her rounds, filling her mouth with their offered cocks. Even with the constant conversation between the men, I was able to hear the occasional sound of her sucking from below. I found myself wondering if she was putting more into it than I had and if they were going to end up preferring her mouth to mine, and then it sank in what a strange thought that was to have. I wanted these men to enjoy the sensation of me sucking their cocks, and more than they enjoyed others, even though I wasn’t completely sure I even knew all of their names. I blushed to myself with the truth of it.

As the night went on and as I kept supplying drinks, the men got more loud and boisterous. They became more handsy, slapping at my ass and squeezing my fake tits, amusing themselves and laughing. 

One of them stood and walked over to the wedding photograph. He looked over his shoulder and addressed Liam. 

“I can’t believe that your Crissy is the same person as in this photo, or that such a submissive little cocksucker ever managed to land a hot piece of ass like this. What is the world coming to?” he said.

“Well, my Crissy isn’t the same person as that man – not anymore. In fact, I think it is safe to say that man doesn’t exist anymore. And, as for him getting to be with the lovely Cheryl, that issue has also been corrected. Crissy doesn’t get anywhere near her without my permission and I think it is safe to say that he will never fuck her again,” Liam replied without getting up from his seat.

“Never again? The poor girl,” he laughed. 

“Oh, don’t worry about her. Lydia’s got her out tonight and I have no doubt she’ll have her needs well taken care of.”

“She looks like a good fuck,” the standing man continued. 

Liam finally stood and walked over to the photo as well. He called me over with a hand signal.

“Crissy, why don’t you tell our friend Eric here if your wife is a good lay,” Liam said.

I blushed, feeling suddenly out of sorts having to describe her in that way.

“Yes, Master. Cheryl is very good in bed, Master,” I replied. 

“But you don’t get to fuck her anymore, do you, Crissy?” Liam asked.

“No, Master. Crissy does not fuck his wife anymore, Master,” I confessed. 

“In fact, even before you met me, you would spend time looking at kinky sissy porn rather than fucking her, wouldn’t you?”

“Yes, Master. Crissy used to look at kinky sissy porn rather than fuck his wife, Master.” It was mortifying to have to share this with them. 

“Aren’t you happy then, that I came along and gave you the opportunity to have your real dreams come true, and to free you from the chore of having to try to satisfy this beautiful woman?” Liam continued while Eric started smiling wider. 

“Yes, Master. Thank you, Master, for making Crissy’s dreams come true, Master.”

“And?...” Liam prompted me.

“And thank you, Master, for freeing Crissy from having to try to satisfy Cheryl in bed, Master,” I finished.

“You are welcome, Crissy,” Liam said. “Now, I would like you to do something for me. As I’m sure you noticed, Martin didn’t bring any panties for his pretty girl Jess. I want you to go upstairs, to Cheryl’s bedroom and choose a pair of her sexiest panties. Maybe they were a pair you bought her on some past Valentine’s Day. Once you’ve chosen just the right pair, bring them back down here, and you can dress Jess in them.”

It seemed that my betrayal would never be allowed to end.

“Yes, Master,” I said meekly.

“Good girl. Go now, and don’t keep us waiting too long.”

I got moving as quickly as I could in my high heels, feeling the size of the plug in my ass with every step. My fake breasts jiggled as I rushed, distracting me and making me feel off balance. Downstairs, in that newly furnished room with all those men, it had seemed like I was in another place altogether but, now that I was upstairs, the reality that all of this was happening in my own home hit me with fresh strength. 

One more flight of stairs and I was up and into our bedroom, fishing through Cheryl’s dresser. There was one pair that I had been thinking of from the moment Liam mentioned Valentine’s Day but I wasn’t able to find them. She had laughed at me and shaken her head when she had opened the gift box, but she had still worn the whole set and I had loved the way she looked and even acted while wearing them. It had ended up being a very fun night, which only made it more confusing that I couldn’t locate the panties. Finally it dawned on me that she might be wearing them for her date night with Lydia. 

Rather than focus on all that meant, I found the next best pair and rushed back down the gathering. Going downstairs was even more tricky to do quickly in heels. The game was in full swing when I returned to re-enter the cloud of cigar smoke. 

“Finally,” said Liam when I approached him. “Was it too hard to pick just the right pair?”

I could tell he was gleefully teasing me, not really looking for an answer. He called out for Jess, who was still under the table, making her rounds from cock to cock. Her eyes seemed dazed when she emerged and I could see that there were strings of precum oozing from her chastity cage. 

“Face the table, Jess, and bend over. The gentlemen won’t mind taking a quick break,” Liam instructed her. 

She faced the poker table, her body right up against the padded edge, and she leaned forward, keeping her back straight. As she leaned forward, the back of her tiny skirt lifted, exposing her ass and the base of the plug nestled between her cheeks. 

“Help her into your wife’s pretty panties, Crissy,” Liam said.

I approached her and knelt down, helping her step into them. The bright red of the panties I’d chosen stood out brightly against her white stockings as I pulled them up her legs. I stood and pulled them all the way up over her tight ass. I found myself impressed by the tone and shape of her body, wondering if I looked as good from behind as she did. 

“Do you like how she looks, Crissy?” Martin asked, perhaps noticing how my eyes had lingered. 

“Jess is very pretty, yes, Sir,” I answered, blushing. 

“I think you should fuck her,” Martin said firmly.

My head jerked around, first to Martin and then to Liam. 

“That sounds like a wonderful idea,” Liam said, “and I have just the thing.”

I stood there in shock, but Liam stood and got into motion. He pulled out a rather imposingly-sized dildo, and then a leather strap-on harness. He came to me, not even bothering to remove my skirt, and started to fit the harness onto me. The dildo, when it was slotted into place, rested just above my own, trapped and useless cock. 

Martin walked up to Jess, still bent over the edge of the poker table waiting, pulled down the panties to just below her ass cheeks, and tugged out her plug. I was given a tube of lubricant, and I squeezed a generous amount over the obscene toy jutting out from my body. I spread the cool goo over the rubber phallus, feeling the texture of its moulded bumps and veins. 

“More of your prize for winning, Crissy,” Liam smiled. “Fuck her until she cums for you.”

It felt so foreign, holding the dildo and guiding the tip to her waiting ass and then watching her stretch to accept it as I moved forward. The sensation for me was strange. I felt the pressure of the base of the dildo pressed up against my body, above my useless cock, but it was devoid of what I would have called pleasure. I fucked her out of obedience and to put on the display for the watching men. I fucked her to please her, since I knew she wanted it, but as I felt my cock flop and jiggle below the dildo, all I felt at first was humiliation and emasculation. 

I was fed, however, by Jess’s increasing moans and reactions. I could feel it when her body was tight around the dildo, and it gave me a kind of perverse satisfaction to be pushing into her still during those moments. I saw her grip at the table and squirm and we all heard her moans and gasps. The dildo was so thick and long, and yet she took it all, over and over and over again. I made her rock with my thrusts as they built up speed, and more than one stack of poker chips was knocked over. 

She came with a loud moan, almost a scream of pleasure. She shuddered and trembled giving me the unique sensation of feeling her reactions transferred to me via the dildo pressing against me.  When her orgasm finally subsided, Liam tapped me on the shoulder and had me slide back, emptying her ass. The dildo flopped down and I was handed a fresh plug to fill her back up with again. As was the way, it was a step larger yet again than the one that had been removed. Once I had managed to twist it inside her, I pulled up the back of Cheryl’s panties to cover up her ass. 

“Look at that, Crissy. You got to fuck a girl after all” Liam laughed, and the rest of the group joined in. “Now, get down on the floor and clean up after her.”

Just like Jess had done for me, I lowered myself down and found the puddles of her milky white cum on the floor and licked them up, moving about to make sure that I found every drop before kneeling upright once more. My mouth was full of the taste of her. Jess looked down at me with an expression of wordless thanks and understanding. Martin had her standing upright now, lifting her skirt to show off the way Cheryl’s panties hugged her caged clit. It seemed like those would be leaving the house with Jess. 

Liam had me rise to my feet again and he removed the dildo and harness from around my hips, then smoothed out my skirt. 

“It is shot time again, Crissy. Please pour twelve shots of tequila,” he instructed. 

I was nervous pouring them, remembering as much as I could of what had happened to me the last time, but it was quickly made clear to me that Jess, as the “new girl,” was still to remain the focus of the men.

We were placed beside each other on our knees in front of the bar and, as before, the men started to gather. The first of them approached Jess first, picked up one of the shots and poured it into her mouth, then got his cock out and got busy using her mouth. She helped him along, using her hands along with the ministrations of her mouth. I just knelt there, so close, watching him take her mouth completely, and seeing her seem to thoroughly enjoy it. 

He seemed eager or perhaps he had been waiting for this part of the evening, as Jess sucked him to completion in what seemed like a short amount of time. He moaned and grunted and came into her mouth. When he drew back, he took the second shot and poured it into her mouth as well, but then he immediately commanded Jess to share both the tequila and cum with me. She leaned towards me and we tilted our heads together to kiss. 

I tasted the strong taste of the alcohol and the texture and taste of his warm load, feeling it slip back and forth between our tongues as we kissed enthusiastically. The men cheered us on, but soon enough the second man wanted his turn. Those waiting would watch and tease and comment and those that had finished moved on for a drink of their own, and like that they all took their turn with us both, even Liam and Martin. I was feeling jealous of Jess by the end, watching her take cock after cock, while I had to watch and settle for the seconds of aftertaste that she shared with me with each kiss. 

The evening was wrapping up. The chips were counted and the winner of the night was handed Jess’s leash. Not long after that he and Martin left, with Jess in tow as the prize. I had a bit of a buzz, but I had not been given near the same access to tequila that Jess had, so I was still in good control of my faculties — enough to feel so exposed and started to wonder if Cheryl would be coming home and when, and what state I might be in when she did. 

The remaining guests finished up their conversations and drinks and cigars in their own time, and filtered out, thanking Liam for the night. It was late by the time it was just Liam and I alone. He had me pour him a scotch and he sat enjoying a cigar of his own while I was set to cleaning up the worst of the mess. Still caged and plugged and dressed as I was, including the heels, I picked up and swept and cleaned, including a few trips up and down the stairs to bring glasses up the dishwasher in the kitchen and to carry bags of garbage out to the garage. 

I approached Liam once I was finished and he finished his drink and smiled up at me. 

“You made me proud tonight, Crissy. You were obedient and arousing,” he said.

“Thank you, Master,” I said, feeling a feeling of warmth rise up in me at having pleased him.

“And you look far too fucking slutty and sexy to have the night end. Come here.”

I walked closer, suddenly nervous. He rose and moved to open up the room, from where he gathered up a few items. When he came back to me, he tugged a long blonde wig onto my head and had me purse my lips so he could refresh my lipstick. He locked a thin leather collar around my neck and hooked his finger through the steel ring at the front of it to pull me close. 

“You look far too fuckable not to show off some more. Come on, let’s go.”

He led me upstairs and right out the front door. I was terrified of being seen but it was too late for anyone on the street to be up, it seemed. He walked me over to his driveway where he opened the passenger door of his truck and helped me into it. 

I felt a wide-eyed disbelief as he walked around to his door, got in, started the engine and pulled out of the driveway. I didn’t have the cover of even a coat to hide how I looked which, from Liam’s smile, was exactly how he wanted me.