Conference Cuckold

I was to attend a conference for my hobby in a city across the state, so I placed an ad for some kink play on a local web site. I am assigned male at birth though very feminine. I present somewhat neutral in my everyday work life though in my personal life, I embrace my feminine side. Many would call me a sissy though I don't resonate with that word, more on that later. I am about 5' 6" with a soft curvy body. I don't have a lot of body hair and I shave my legs and pubic hair regularly.

Because this conference was out of town, I was going to take a chance. When I packed, I included only feminine clothes: lacy panties and bras, leggings, blouses, dresses, ballet flats, a pair of low heels plus some of my favorite jewelry. I prefer a natural look so don't use much of any make up. I also decided to bring a tiny cage that I found on the internet for my clitty. It is metal and covered with pink rubber and has the word 'SISSY' on it in raised letters on it. While I said above that most would call me a sissy, for me, it diminishes my femininity, makes me less of the woman I wish that I was in reality. I also decided to bring a few toys with me though as you will see, I did not need them in the end. I thought about leaving the key to the cage at home though I am glad that I brought it.

A few weeks before the conference, I received a message on the web site in answer to my ad. A women who shared my hobby was attending the conference along with her cuckold husband, would I be interested in meeting to see if we were compatible? She was lovely--tanned skin, dark hair and eyes, moderately voluptuous and with curves in all the right places. She asked in her email, would I mind if she was pregnant. That made my heart skip a beat was that she was far along in a pregnancy. Though she had some photos on her profile, none were of her pregnant. My mouth went dry since I had longed to be able to be pregnant and my porn consumption recently was of lesbians playing where one of them was pregnant.

With shaky hands, I answered the message saying that, no, her being pregnant was not an issue, perhaps we could meet for dinner the night before the conference to see if we hit it off. She replied with excitement, instructing me to meet her and her cuckold husband at such and such restaurant in the hotel at so and so a time, and she included a more recent photo of the two of them so I would recognize them. Pregnancy suited her and she looked all the more curvaceous and voluptuous.

When the weekend of the conference came, I was excited to travel to the city. I passed through TSA and immediately went to the gender neutral bathroom to prepare myself as I would arrive at the hotel near the designated time to meet. I was wearing sheer black and white polka dot panties with a matching bra under a loose black empire waist dress along with black ballet flats. I wore pearls and pearl earrings and my hair was dyed blue and cut in a bob. I had tasteful silver toned rings in each hand, a silver link bracelet on one wrist and a watch on the other. I had my phone, ID, and cards in a clutch as well as my carryon bag. In the bathroom, I slipped my panties down and put the cage on my clitty. The keys were on a chain that I then put around my neck and under my dress, something Ma'am--that is what I was to call her in private--asked me to do. The cold metal against my skin was enticing and I could feel my clitty swell in its confinement.

I left the bathroom, boarded my flight, and had an uneventful trip to the city and to the hotel. I checked it, dropped off my bags, and made it to the restaurant with minutes to spare, holding my clutch a bit nervously, suddenly feeling very conspicuous. As I approached the hostess station, I spied Ma'am and her husband at a corner table and I let the hostess know that I was meeting some friends. She beckoned me forth and I approached the table.

Ma'am smiled and said in her thick southern drawl, "My my, aren't you pretty. Give me a twirl, Simone." I did as commanded and she continued to smile, gesturing for me to sit down. "Some folks post old photos on the site--heck, mine are from before I got knocked up--and I am glad to see that yours are current and accurate."

I smiled and nodded, "It is important to me for people to know what they are getting, Ma'am."

She smiled and said, "Do you have something for me, Simone?" I smiled and nodded, withdrawing the chain from my neck and holding it out to her. She crooked a finger, beckoning me to stand and come to her. She inclined her body forward, clearly indicating that she wanted me to drape the necklace over her head. I stood and approached her, reaching out to drape the necklace with the keys over her head, the keys themselves resting in her cleavage, displayed by the partially unbuttoned blouse which barely contained her breasts, a hint of her red lace lingerie showing under the black silk. Her scent was intoxicating to me and she could tell, saying, "I would have you kneel, but the others in the restaurant have not consented to our scene. I can tell that I have already had an effect on you, my good girl." My heart skipped a beat and my clitty swelled in its cage. "Now have a seat and we will have a light dinner while we all get to know each other better."

I sat, we ordered, and dined, and when we finished, she said, "I gather you would like to proceed, girl."

I nodded, she cocked an eyebrow, "Y-yes Ma'am."

She smiled, "Much better, I won't hold that against you this time. Come with me to the ladies room." She rose, I followed, and we found the ladies room, which she used and suggested that I did as well. She then took some makeup items from her bag. She applied some blush to me, some eye liner and shadow, some lipstick. "Not that you didn't look darling already, girl, I just wanted to fancy you up a bit. Now, give me your clutch. I presume it has your phone and cards." With shaky hands, I gave it to her and she smiled, "Now don't you worry your pretty little head, girl, you will get it back. I am going to leave, pick up my boy, and return to our room. Oh! Give me your watch, too." And I complied. "Your mission, girl, and you have no choice but to accept it, is to get two drinks bought for you and to get at least one phone number. If you are real sassy, you can imply that you are for hire, though I won't require that from you."

I stammered, head swimming, "Y-yes, Ma'am" as she turned and left me there to contemplate my fate. It occurred to me that she did not give me her room number. I would have to figure that out as well as when to return. I made my way back to the bar and made some small talk with the bartender, asking for some water.

After a while, an older gentleman came to the bar and asked, "Is this seat taken?"

I smiled and gestured, "It is now!" in my most breathy voice.

He sat and smiled, asking, "May I buy you a drink?"

I smiled, thinking, this might be easier than I thought, replying, "Yes, please, a rye Manhattan, up, if you well."

He cocked his head, saying, "A woman after my own heart. Make that two, my good man." The drinks came and we chatted, my head swimming a bit from the attention and from the potent cocktail and for being validated in my femininity.

When I was done, another two drinks appeared, and I had accomplished one goal. "Why thank you, I *will* have another!" and I giggled playfully, feeling his hand on my leg. I smiled, leaning over, whispering, "Be careful, if you break it, you buy it."

He squeezed my thigh and turned his head to whisper in my ear, "And if I don't break it?"

I leaned back, cocking my head and smiling before saying, "I have an... appointment... tonight, though I will be here all weekend. Perhaps we can make an arrangement for tomorrow?" He nodded and smiled, putting his hand into his suit jacket pocket and palming something, then grasping my hands in his, where I felt two things--a business card and some bills. I discreetly slipped them into my bra, smiling, saying, "I seem to have misplaced my clutch. I'll have to check with the hostess."

We finished our drinks and I said I would call him in the morning to see if we could set a time and place for our next... meeting. He departed, I finished my water, went to the ladies room, checking my bra and finding his card and 5 crisp $100 bills. I thought to myself, 'I may be in the wrong line of work.' I went to the hostess station and as expected, my clutch was there, though it was empty but for a slip of paper with a room number, a room on a high floor, clearly an executive suite. I thanked the hostess and made my way to the elevator and hit the top highest numbered button. I was feeling tipsy and sassy and wonderfully intoxicated. I went to the room and knocked. Ma'am's husband, her boy, answered the door in the nude, and I took him in more fully before entering. He was not in bad shape and his cock was locked in a small metal cage which seemed to secure via a piercing. I imagine the length of time my gaze took made him uncomfortable and I relished it, finally saying, "Thank you... boy." and sauntering it.

Ma'am sat on a chaise lounge in a tasteful sheer babydoll and panty set covered in a silk robe that was untied. Her boy knelt next to her on the floor and she gestured to an ottoman set nearby.

I sat demurely and Ma'am said, "I like you. Smart, just enough sass, obedient, clever enough to find your way here. I will let you in on a secret. We live in your town, we are here for the conference, too. I would not be surprised if we are on the same flight back. Now let's sit a while and you tell me what has happened since. I related my story from the bar, withdrawing the card and cash from my clutch. She whistled, "This gentleman, Oh my, let's just say he is a mover and shaker in a local industry and quite well off. Let's talk more about you seeing him tomorrow later. I will keep these for now." She set the card and cash off to the side. Ma'am continued, "Now, boy, please tell our girl here our story."

He swallowed, looked down at first, then looked me full in the eye. "Ma'am is a successful business woman who was able to stop working for corporate America and walk her own path. I met Ma'am while she was working as a professional dominant in New Orleans several years ago. We hit it off and whenever I visited, I would spend time with her. I am trained as an electrical engineer and my hobby is furniture building. When Ma'am decided that working with needy rich men had run its course, she made a proposal that I become her full time submissive and husband. Her means are such that neither of us needs to work though I make custom furniture and toys both for our home and for sale. That was 3 years ago and she immediately had my cock head pierced through and put me in chastity. She takes me out from time to time for cleaning though would never let me enter her or anyone else. 2 years ago, we became legally married, and last year, she announced that she wanted a child."

He paused and looked at Ma'am who nodded her head and said, "Go on."

He swallowed and continued, "She denied me for the longest ever, 90 days with no release, caged, teased. One day, she attached me to our bondage bed and removed my cage. She gave me some viagra and teased me to fully erect for the first time in months. She then lowered herself onto me and using her muscles, brought me to several orgasms that were blissful though somewhat ruined for me as she did little in the way of moving to stimulate me. She used a magic wand her herself and I could feel the shuddering climax. After her orgasm, she rose off of me, did some yoga, then washed my penis and locked me in this cage, the smallest yet, secured through the piercing in my cock head. She is due next month and the pregnancy has gone swimmingly. This is something of a last trip before we descend into parenthood."

Ma'am smiled, "Very good, boy, I think our girl has a good sense of how we got to today. Now, I want to reward my boy here though I have no more desire to have him inside of me in any way, his cocklet has served its purpose. If you are willing, girl--yes, you must consent--I would like you to please him and please me this weekend, starting tonight. I have a special surprise for him, depending on how things go. What do you think, girl?"

I blushed and smiled, saying, "That sounds delightful, Ma'am. Your boy is quite adorable and he has that look of desperation in him. I consent. How would you like me to please him?"

Ma'am smiled, saying, "I am going to leave that to you, girl. You have my permission to do what you wish provided you don't do permanent harm and I will be here the whole to observe and guide if needed."

I smiled mischievously and nodded, leaving my seat and motioning her boy to the ottoman and asking, "Ma'am, do you have some rope or restraints and may I have the key to remove his cage?"

As her boy settled on the ottoman, Ma'am said, "Yes, there is a bag of goodies in the closet there, go fetch it."

I fetched the bag which has cuffs and rope among other things. I take in the room and see a second ottoman and push it next to the first, creating a rectangle. I push the boy down and arrange him so his legs hang over one end, I put cuffs on his ankles, then secure them with rope to the legs of the ottoman. I take more rope and circle it under the ottoman and across his thighs, his cocklet straining in the cage. Moving up, I secure his chest as well, affixing him to the second ottoman, putting a small pillow under his head. Lastly, I cuff his wrists and secure them to the bottom of the ottoman, leaving him quite helpless.

Ma'am smiled, "You go girl, you are quite creative, this is quite the show!"

I smile and say, "Thank you, Ma'am, I have had a lot of practice with self bondage." Ma'am hands over the custom key that secures the piercing through the boy's cock head and I remove the cage, his finally free cock, aided by more viagra, springing to full attention. I run my lacquered nails along it and it seems to get even harder, harder than seemingly possible. I look to Ma'am and she nods. I slip my panties off from under the dress though don't remove anything else. I set the panties aside and straddle the boys face, lowering my rear passage onto his face, saying, "Tongue me, boy. I should be clean but I want to be sure." As I first the wet warmth tentatively probing me that more vigorously licking and thrusting into me, I leaned forward and took his cock head into my mouth, looking up at Ma'am, as I suckled the head, listening to the boy moan and buck in his restraints, his efforts on my hole getting more enthusiastic. From time to time, I lowered myself more onto his face and took his breath away which only seemed to make his cock throb all the harder.

Ma'am chuckled and drawled, "Now, my boy is under orders not to release without my permission and I see that you are making that hard--pun intended--on him. Now, if he can hold it in until I say, you will swallow. If not, well, you get to do what you want."

I nodded, plunging his cock deep into my throat. It was not too big and not too small and I had practiced lessening my gag reaction. I could feel the strain of him holding back when I plunged onto him while I ground into his face then hear the gasps of relieved breath each time that I took my wet mouth off of him and raised my hips. After several rounds of edging, I came to realize that Ma'am was not intending to give him permission and I ground my hole into the boys mouth, holding his cockhead in my mouth, and lashing it with my tongue until he bucked and squirmed and stuck his tongue deep into my hole and released into my mouth. The moment that I tasted the salty goo, I stopped moving my mouth, merely sucking him dry and holding his spunk in my mouth. I dismounted him and put my face close to his.

Ma'am picked up on my intentions and said, "Open wide, boy, and don't swallow." I could see the reluctance and obedience on his face as opened his mouth, putting his tongue to the roof and I let all of his spunk fall into his mouth until my mouth was empty, spitting the last bits into his mouth.

I said, "Close your mouth and don't swallow" before wiping my lips and face on his face so he could smell his spunk. I returned to his still throbbing cock and slowly began to jerk him off, his body twisting and twitching in his bonds as I mercilessly pushed him to the edge over and over, the boy desperate to cry out though also trying to hold his own cum in his mouth. I finally relented, watching carefully for him to lose control then letting go of his cock to ruin his orgasm and let his second batch of cum seep down his cock.

His eyes widened and I said, "I hope you did not swallow!" He shook his head, looking terrified. "Good boy," I said, "now lube me up good!" I lowered myself onto his face, grinding my hole into his mouth again, my caged clitty resting on his nose. He tongued me vigorously, using his cum to lube my hole. When I felt satisfied, I dismounted his face and again lowered myself onto his slick cock, coated with his cum, my hole lubed with his cum, and I dropped myself fully onto him, taking him all the way in. He arched his back to meet me and gasped in pained pleasure. I sat on his poor cock and squeezed him with my two sphincters, not unlike what I imagined Ma'am did when he deposited his seed into her. He groaned and cried and it became more desperate when I started bouncing on his cock with abandon. My breath became ragged as my arousal grew and I gasped out, "May I cum, Ma'am, please?"

Ma'am shook her head, saying, "You must edge 4 more times." And I did, taking myself to the place of desperate release and then backing down, my clitty throbbing in the cage, my p-spot throbbing, until Ma'am said, "Now, girl, cum for me."

It took no time for my body to react, my hole pulsing on his cock, my spunk dribbling down in pulse after pulse, me slamming myself down on the boys cock over and over until I felt it start to shudder. I lifted myself so that just his cock head was inside of my and squeezed him until I felt him start to fill me then I let the orgasm ruin as he pulsed inside of me, fulling me with his cum. I lifted myself off of him and lowered myself onto his face again, saying, "Clean me, boy." I could feel the licking and sucking as he took in the last ejaculation that I later learned he would ever have inside of anyone. I could feel my clitty swell from the attention to my hole and I stayed perhaps longer than needed, sometimes taking the boy's breath away only to feel him buck when his air became short.

Eventually, when I was satisfied, Ma'am beckoned me to the pillow on which the boy had been sitting, leaving him tied to the ottomans, saying, "BRAVA, girl, I suspected that you had it in you though I had no idea how skilled that you are, that was a wonderful performance."

While watching us, Ma'am had been toying with her own sex, running her fingers over the panties that covered the swollen lips. With some effort, she shed the panties, turned herself to me, beckoned me to lean forward and open wide, then matched her lower lips to mine. She put her hand behind my head and sighed then I felt the hot stream of her piss hitting the back of my throat, initially overwhelming, especially when she used her other hand to hold my nose closed, leaving me to swallow or pass out from lack of air. I tasted her arousal as well as the acrid nectar that I gulped down. After what seemed like an eternity, she released me and I coughed and sputtered, gasping for air as my head swam. "Good girl, you are passing all of the tests with flying colors. Now, I want you to service me with that pretty mouth."

Shifting her hips slightly, the great belly looming above me, she drew my mouth to her swollen lips and her engorged clit, which I devoured both eagerly and gently, bringing her to three shuddering orgasms while her boy watched helplessly, his cock still raging hard from the little blue pill. Ma'am pulled my head away, glistening with her juices, saying, "Now where are those panties you shed?" I found them and she used them to wipe my face clean and wipe her sex clean, then gesturing to the boy's head. I know immediately what she wanted, balling the panties up, and shoving them into his mouth. I found another bit of rope that I fed under the ottoman and across his mouth to both hold in the sopping panties and to hold him all the more securely.