Conference Cuckold Pt. 02

(While not absolutely necessary, it may help to read the first part of this story, "Conference Cuckold," by the same author. This chapter starts with a quick synopsis of the previous chapter.)

Previously on Conference Cuckold: Simone, an Assigned Male at Birth sissy, travels to a conference and meets Ma'am, a pregnant former pro domme, and boy, her cuckold husband. Simone, now simply called girl, is tasked to get some drinks and a phone number from a stranger while possibly posing as a sex worker. She succeeds, then gives boy and Ma'am some pleasure before being collared, leashed, gagged, and secured in an oversized dog crate for the night with her arms secured high behind her back, her collar secured to the floor of the cage, and the rubber cock in her mouth tickling her gag reflex. This is where we find her now....

I wake up, again, for I have drifted off to sleep on and off all night. I have no sense of when I was caged or what time it is now, though I hear movement around the room. My whole body is stiff, my arms in their strappado position, my collar secured to the bottom of the cage, my legs sore from being curled beneath me for hours and hours. Perhaps hearing me stirring, someone... that's right, Ma'am... whips the opaque cover off the cage and I would be blinded were my eyes not staring at the floor of the cage.

"Rise and shine, girl!" says Ma'am enthusiastically. She continues, "Well, shine, at least, as rising may be a challenge for the moment." She unfastens my wrists from the top of the cage, unlocks and opens the door, frees my collar, then tugs me out none-too-gently of of the cage, where I do my best to stretch my legs. She unconnects my hands from behind my back but leaves on the bondage mittens but I can stretch finally out my arms. I roll over on my back and look up at Ma'am, her pregnant belly dominating my view. She is in panties and a bra and pulling a loose dress over her head with the help of her boy who is himself dressed in street clothes. "When I woke up, I untied my boy and caged his cocklet again," said Ma'am. "We have a busy day at the conference today. I don't believe that I shared that I am a presenter and I have several meetings today plus a lunch. You will be mostly on your own, though I think we should reach out to Mr. Businessman before I leave."

I nod, quietly, turning back over onto all fours, spying the two bowls a few feet away. One appears to contain a mix of corned beef hash, scrambled eggs, and home fries while the other contains some water. I look up and Ma'am and she nods, pulling me be the collar to the bowls. She removes the gag, I lower my face to the food, and devour it hungrily, pausing sometimes to drink some water, until I finish the bowl and lick it clean, saying, "Thank you Ma'am, that was tasty." I stay on tall fours awaiting further instruction.

"Boy, clean up girl's face!" Ma'am commands. Boy quickly drops to his knees, crawls to me, then proceeds to lick off every bit of food stuck to my face until I am clean if still a bit sticky. When he is done, she says, "Good job, boy. Girl, you can go to the bathroom and finish cleaning yourself, use the bathroom, and come back." She removes the collar, leash, and bondage mittens though I still crawl to the bathroom. I thoroughly wash my face and use the bathroom then return to Ma'am again, this time walking. I sit, still nude but for my wee clitty cage, on one of the ottomans.

Ma'am hands me my phone and Mr. Businessman's card. I decide to send him a text:

[Yes, Maria, there are some things we should go over before I leave later this afternoon. Let's meet at lunchtime.]

I am confused for a moment though I roll with it.

[Of course it works for you, Maria, you *do* work for me. I will be there at 11:30 am sharp.]

Ma'am has been looking over my shoulder and she says, "Ah, some role-play, perhaps you are his assistant or secretary. Hop in the shower quickly and we'll get you made up." I comply, returning with my short hair slicked back to dry into its sapphire blue bob cut. "Let's see," she says, "some light blue eye shadow, liner, and mascara and some pink lipstick will do. Take the lipstick with you and you can reapply, girl."

I nod, saying, "Thank you, Ma'am, you are so kind to me. I look forward to sharing my experience with you later." I pull my dress over my head without bothering with the bra and panties, then take my clutch to head back to my room. I say, "It's time for my "Stride of Pride!"

"Stride of Pride, I like that. So much better than Walk of Shame," says Ma'am. "Reach out to me after 1:30 and let me know how it went."

"Will do, Ma'am. Good day, boy," I answer, practically bouncing out the door and to my room, my underthings balled in my hand. I reach my room, change into clean panties and a bra, skirted leggings, a low-cut loose sleeveless top, and low Maryjane heels. I make my way to the registration desk and get my badge and other conference items. Looking over to the cafe, I see what looks like Mr. Businessman with his back to me talking to someone who could be my twin cousin. A blue bob, a little longer than mine, likely about my height, wearing a neat business jacket or dress. She--I am guessing this is Maria--is fuller in the chest than me and I am guessing fuller in the bottom. I make note of some of her mannerisms then go on my way to enjoy the first two morning sessions.

The sessions were interesting though I admit that I was rather distracted. I did pass Ma'am and boy once in the hall though we did not acknowledge one another. I did not see Mr. Businessman and Maria again as they were not part of the conference. I found my way back to my room at 11:00 am and began to prepare myself. I touched up shaving my legs and pubic hair then looked into my closet to assess my wardrobe. First, some garters and stockings to match my bra and panties, panties over garters, of course. Now for what else to wear. Ah, yes, the wrap dress would work well. I slipped on the dark blue dress, not unlike a robe, crossed the halves one over the other leaving some cleavage showing, and secured the tie in a bow behind my back. I applied more lipstick and found the legal pad I had acquired during the morning, setting it, along with a pen, on one side of the table in the room, placing the chairs opposite each other. I fetched two glasses and a water pitcher. I took in the scene and it looked perfect. And I was just in time, as the sharp rap at the door and 11:30 am sharp jolted me. I opened the door to see Mr. Businessman, actually Mr. Johnson, at the door.

"Good morning, Mr. Johnson," I began, "please come in. I hope that you find the arrangements to your satisfaction.

He entered, looking around and I think I saw a brief smile crack his lips. He nodded, looking more stern, saying, "Yes, this is fine, Maria. Have a seat." I sat by the legal pad and poured some water for each of us while he removed his suit jacket and hung it on the back of the chair before sitting down and looking me in the eye so intensely that I blushed from my cheeks to my cleavage. "We have some serious things to discuss, Maria," he began, "I have some concerns about your performance, and, to be honest, about the audacity with which you asked for a raise recently."

I swallowed, nodding, stammering without much need to play act. "I-I'm sorry, Sir, I thought that I have been doing a good job lately."

Mr. Johnson continued, "In some areas, yes, Maria, you have done well, but your attention to detail, the number of small errors, the lack of timeliness, they have all outshone your good work."

Feeling genuinely defensive, I countered, "This meeting was on time, Sir."

"Yes, Maria, but you were to meet me in the lobby cafe this morning and you were no where to be found," he said.

I was flabbergasted, the intense feelings coming up in me--Maria *was* there this morning, I saw her, I was timely for this meeting. I was genuine when I said, "I-I don't don't know what to say, Sir, other than I am sorry and I will do better in the future."

"You better, Maria. You know that I am only doing your mother, my sister in law, a favor by employing you. I would not have chosen you had I had a choice and now I am stuck with you."

I felt tears well up in my eyes, "I-I didn't know. I feel like such a disappointment, Sir. How can I make it up to you?" Mr. Johnson let his fingers tap tap tap on the table for far too long. I got restless, shifting in my chair, sipping my water nervously. "P-perhaps, Sir, there are some things I could... do... to make it up to you in the meantime? I do need this job and my mother would be so angry that I let her... and you... down."

Mr. Johnson scoffed, "You are acting like a child, not a grown woman. You have no self-discipline. Perhaps you need some correction."

I lowered my eyes and murmured, "I will do anything, *anything* to make it up to you."

"Yes, you will, Maria, yes you will." he said, standing up and moving his chair to the middle of the room. "Come here, you slut." The word was like a slap in the face and I found myself trembling as I stood before him. "Wearing this low cut dress and those seamed stockings. You look like some kind of whore and maybe I should treat you like one. Turn around." I complied, and he undid the bow of the tie of the dress, letting the dress slide down my body, revealing the matching bra, panty, and garter set. He turned me back around and patted his lap. I went to sit on his lap and he slapped me hard across the face, "No, you stupid slut, lay on my lap face down."

My tears were genuine as he laid me across his lap and I stammered, "Yes, Sir." I was trembling now, wondering what I had gotten myself into. I felt him tug my panties into my crack, leaving my cheeks exposed.

"Count," he said, laying the first spanks onto my bottom.

"One!" I nearly screamed from the surprise, "two, thr-three, four, f-five," I continued as the spanks kept coming rapid fire, some on the left, some on the right, some across both cheeks, some lower cutting across the tops of my stockings. When I cried out, "thirty!" he paused.

"As you know, slut, I turn 50 soon. I am going to give you 21 more. You are 21 and that will make 51 for me with one for good luck."

Without much pause, he continued, me sobbing out the numbers one after the other, keeping count though losing any sense of control of my thrashing and crying in his lap. I did, however, feel the growing hardness in his pants as he took out his frustrations on me. I cried out, "Fifty!" knowing that it would soon be over. He rubbed my red sore bottom tenderly before laying down the hardest of the spanks, across both cheeks. So hard that as I cried out "Fifty-one!" I rolled out of his lap and sprawled onto the floor, looking up at him with tears streaming, makeup streaming down my cheeks.

"Good girl, I hope that will be a lesson to you," said Mr. Johnson. I was so confused. Sore, deeply humiliated, really feeling as though I was the bad young assistant. Though also so turned on, my clitty dripping in its cage. I shakily got to my knees and looked up at him, licking my lips. He "manspread" which I took as a hint. I unzipped his pants, pulled them and his boxers down, he closing his legs to assist me, and I looked up at him with eager eyes. "Go on, slut. I knew you were a whore but not how much. I know about the Onlysluts social media page that you have, you know."

I swallowed, running my tongue from the base of his cock to the tip, gathering the precum there before lowering my head fully on his cock, the rigid member teasing the spot where I had had the gag all night. I closed my lips on his cock and slowly slid out to the tip, licking all the way, only to plunge down again, over and over. After a while, I let his cock go and I took each of his musky tasting balls into my mouth and then both, surprising myself with my skill. After I licked and sucked his balls for a while, he grabbed me by the hair and pulled me back to his cock, ramming me down onto it over and over until I was drooling and crying again, feeling both so out of control and so turned on by not only being used, but also being used for money.

When he was satisfied with the face fucking, he pushed me down to sprawl on the floor, facing him. He put the sole of his fancy Italian loafer onto my neck and said, "That was... adequate. Now, I am going to fuck you into next week." He dragged me up, spun me around, and pushed me to the window. The hotel had an atrium and my window looked down onto it from a middle level floor. I held the window sill and felt him drag down my panties, "Look at all those people. What if they knew you were a whore being fucked while watching them?" He pressed his slick cock to my hole and began to fuck me without holding back. At one point, he reached forward and grabbed both of my wrists, pulling them behind my back, pressing my face into the glass each time he rammed into me.

I gasped out, saying, "I am going to come, Sir. May I?"

"No, you fucking whore, how dare you even ask?" He dragged me away from the window and tossed me down on the bed on my back, pulling my legs up by his shoulders. He plunged back into me and then reached down to grab my neck, pressing in those vital arteries there. My vision began to get fuzzy and I imagined that he saw my eyes rolling back into my head so he lessened the pressure though still held my neck. He did this over and over until, gasping, I blacked out, my caged cocklet spurting out my spunk. I awoke, confused, not sure what had happened, feeling him spurt jet after jet of his cum on my face.

"Ah, ahhh, ahhhhhhhh!" I cried out in my confusion until he released me and let me lay on the bed. I watched him as he cleaned up and zipped up. He let 10 more hundreds flutter down from his hand and land on my body.

"You were worth every penny," said Mr. Johnson. "The real Maria is nowhere near as bad as I made you out to be though I do think she has an Onlysluts page. I have had the hots for her since I hired her and when I saw you last night, I knew you were the perfect person to help get it out of my system." He looked at his watch and smiled, "I have a plane to catch and now that I have your number, I may reach out again in the future."

I gasped out, "Thank you Mr. Johnson, the pleasure was mine." I watched him leave and spent a few more minutes gathering myself before heading to the bathroom to clean up for the afternoon. I looked at myself in the mirror and knew that I had to get a photo of the tear streaked makeup cum covered face, haloed by my mess of blue hair so I took a shot. I would show it to Ma'am later. I showered off, gathered my $1000, and changed for the third time that day, this time into a cute lighter blue loose flapper dress over a powder blue bra and panty set. I found my pair of blue ballet flats and reached out to Ma'am to check in with her.

Ma'am asked that I come to her room and report on my morning. I recounted the story of my time with Mr. Johnson and she smiled and cooed with approval, saying, "Hmmmm, that sounds wonderful. I bet that sissy pussy of yours is aching for more, girl." I made sure to show her the photo I took and she asked me to send it to her.

I nodded, saying, "Yes, Ma'am, I am finding it quite hard to concentrate. And I was pondering whether you would give me another task for today."

Ma'am smiled, nodding, saying, "I bet you can guess my next task for you, girl."

"Find Maria and... connect... with her?" I offered.

"See, boy, our girl is quite smart," she said, turning to me, continuing, "Indeed. Go to your afternoon sessions and find this Maria and get with her. If you think it worth it, offer to bring her back to our room. We have more sessions this afternoon and a dinner so we likely won't be available until around 10 pm."

"Yes, Ma'am," I replied, smiling, relishing the thought of another adventure. I departed, attended my sessions, though was constantly distracted by memories of my experience with Ma'am and her boy, with Mr. Johnson, and what I might discover with Maria. After the sessions were done, I found myself at the bar again.

I was surprised to hear behind me, "May I join you?" I turned and saw Maria addressing me. She looked at my badge and saying again, "Simone. May I join you?"

I gestured to the empty seat next to me and said, "Yes, please. I confess I saw you in the lobby this morning and I thought that I had seen my doppelgänger." I took her in more fully. Yes, bigger of chest than me, the snug business jacket containing her assets, and, yes, indeed, bigger in bottom than me, the pencil skirt hugging her closely and ending just above the knee.

"Likewise, I saw you, too, and I was intrigued. It's been a long day and this seems like a nice way to finish it off. My boss disappeared for two hours during lunch then unloaded a bunch of tasks on me before leaving to catch a flight elsewhere. I finally finished the last item and here I am!"

"May I buy you a drink, then?" I inquired.

She nodded, saying, "That would be lovely. What are you drinking?"

I gestured to the bartender, the same one from last night, who said, "Another rye Manhattan?" And I nodded, gesturing to Maria.

"And whatever she wants, too." I added.

"Oh, my boss would love you, Simone. That's too much for me though I will take a Sapphire and tonic with a twist, please." I nodded to the bartender and set my card on the bar, chuckling to myself that her boss enjoyed me more than she knew. We chit chatted about her work and my experience at the conference. I could tell that she was curious about me though seemed to hold back some. We had a second round of drinks and I found my arm resting on hers, my head swimming a bit. She asked, "What is it, Simone?"

I took a deep breath and said, "Maria, I want to be honest with you. I know where Mr. Johnson was at lunch time."

"How did you know his.... Wait, was he with you?" she inquired. I nodded and she let out a long breath, saying, "Thank you for letting me know though now I am all curious, since, you know, there is some resemblance between the two of us." We finished our second drinks, holding hands, and I signaled for a third before taking another deep breath.

"We met last night, here, in fact, at this bar. I... implied... that my services might be for hire and he gave me his card and an... advance." I watched her for any reaction but her face was unreadable so I continued, "I texted him this morning and we met at lunch for... a meeting... where he called me Maria and punished me for some mistakes that I had made. When we were done, I swear, he said that you were doing a great job but that he had the hots for you and that he needed to get it out of his system. He also said that he suspected that you have an Onlysluts page." I paused to let what I said sink in for Maria.

It was now her turn to take a deep breath and she squeezed my hand, saying, "Thank you, Simone, for sharing this with me. I wish that you had told me sooner though I suspect," gesturing to the drinks, "that you needed some liquid courage." I nodded and she continued, "I won't hold it against you... too much... though if I told you that you had a hot body, would you hold it against me?"

I laughed, saying, "What? Why would I hold it against... Oh! Yes, of course." As we finished our third drinks she demanded that I tell her exactly what happened and I was honest with her. She also inquired about my background and I shared with her that I had met Ma'am and her boy here at the conference and that she had tasked me to get some drinks and a number last night and, with some blushing, that she had, "suggested that I try to find you, Maria. But it seems that you found me."