I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at the theater club where I had been displayed on my coming-out evening. The pumping of my boobs and cock had enlarged both. My erect cock was now 4-1/2" long, but it didn't look like it was making any more progress and I was still struggling with premature ejaculation. I had only managed to hold off coming until Hannah was satisfied by my strapon extension one time, but we were both pretty happy with our sex lives now. We both looked forward to the weekdays and to the weekends.
One Saturday after breakfast, Mistress Hannah told me this would be an afternoon I would long remember. I was to prepare by being as clean and feminine as possible. She laid out an outfit that was like a serving maid's dress, but it was ridiculously short, especially in back. It was pink instead of black and had a short white apron. It barely concealed my dangling balls, which wouldn't stay inside the thin crotch of my brand new satin hot pink thong panties, and it didn't conceal the lacy tops of my pink thigh-hugger stockings. Of course, I was wearing my blond wig and had red painted finger and toe nails. My shoes were hot pink patent leather flats, more suitable for serving than the higher heels I normally wore for our nights out on the town. My body smooth and my makeup was as flawless as I could manage. I knew that I could never pass inspection for long with a real woman, but Mistress Hannah said I could do much better than most men.
While I was dressing up, Mistress Hannah dressed in the sexy schoolgirl outfit that she sometimes wore for our play during the week. Then she whipped together a luncheon. It was clear that we had enough food and drinks for several guests, so it wasn't a big surprise when the doorbell rang. Mistess Hannah brought me to the door, which was unusual when I was crossdressed, because we didn't want the neighbors to see me. After peering through the peephole, she ordered me to answer it. I was surprised to find a petite young Asian woman there. "Hi. Is Hannah here?", she asked.
Mistress Hannah stepped out from behind me and squealed, "Leelee!". I was treated to several minutes of squealing and hugging as the two women had their reunion.
After they were done, the young Asian woman introduced herself to me. "Hi, I'm Lisa. My friends call me Leelee."
Before I could say anything, Mistress Hannah spoke up. "Leelee, this is my husband and little sissy-boy. I call him Michelle or Slave Shelley. If he fails to call you Mistress Leelee, you may punish him."
Mistress Leelee seemed completely flabbergasted. "This is a man? Your husband? What's going on?"
"Oh, dear. Didn't my 'other guest' clue you in? That's just like her isn't it? Oh well, Michelle will be serving our every need as we catch up with each other."
"Oh," said Mistress Leelee. "No your 'other guest' just told me to be prepared for something different. She didn't tell me you were married to a sissy-boy."
Just then, the doorbell rang again and after Mistress Hannah checked the peep, she told me to welcome our 'other guest'. I opened the door and to my surprise, Mistress Bella was there. I let her in and the squealing started again as Mistresses Leelee and Bella hugged and chatted with Mistress Hannah. Apparently this was the first reunion with Mistress Leelee since they had been sorority sisters in college. Eventually, Mistress Hannah suggested they sit in the living room while I prepared a pitcher of mimosas for them.
When I returned with a serving tray and three glasses, I served the first to Mistress Leelee and turned around to serve the next to Mistress Bella. As I bent over to hand it to her, Mistess Leelee giggled and said, "Oh look, he's got writing on his butt and something inside it." The writing was added with a red Sharpie that morning by Mistress Hannah. She had once again written "FUCK HERE" across my ass with arrows on both cheeks beneath it that pointed to my buttplug.
Mistress Bella said, "Oh, that's nothing. I'll be putting something much larger up his ass before the day is over. You can too, if you want. Hannah wants us to try and wear him out." This made Mistress Leelee giggle again and I began to suspect that she would enjoy today no matter what. The visiting mistresses started to nibble at the platters of finger sandwiches and snacks that were on the coffee table so Mistress Hannah dismissed me to the kitchen. I could hear them talking and giggling for quite a while.
Soon after they got quiet, I heard the call bell and returned to the room. Mistress Bella had changed into a black leather dominatrix outfit and it appeared that she was going to demonstrate how to dominate a sissy boy for Mistress Hannah and Mistress Leelee. To kick the festivities off, Mistress Hannah addressed me as Slave Shelley and formally ordered me to obey the commands of the other mistresses and to attend to their needs as I would hers.
With that out of the way, Mistress Bella pointed her riding crop at a point on the floor and ordered me to stand for inspection. "Before I begin the inspection, you must curtsey respectfully to each of us." I had been practicing this, so I placed one foot behind the other, parted my knees just slightly, and as I dipped, I spread my dress skirt wide and lowered my eyes, first to Mistress Bella, then to Mistress Leelee and finally to Mistress Hannah. "Freeze," she ordered as I straightened. "Your form was adequate, but you did that in the wrong order. You must always start with your owner. Now try that again."
I curtsied first to Mistress Hannah, then to Mistress Leelee and finally to Mistress Bella. I chose her to be the last because she was directing me and apparently that was the right choice.
"Now bend at the waist one quarter." I bent as directed and received only one sharp smack from the riding crop across both ass cheeks. She started the personal inspection with my nails and makeup, then ordered me to remove my dress. Mistress Leelee giggled as I removed the dress. My cock was hard under my panties and Mistress Bella pointed that out to Mistress Leelee by placing the riding crop under it and lifting it slightly. "This is why he became a slave. It's too short and thin to please his owner."
"Now remove your bra and panties." When I complied, Mistress Leelee seemed quite impressed. My shaved cock and balls were of course very pink and my hairless body is very pale except for freckles on my arms and shoulders. My breasts had responded nicely to the pumping and I now had manboobs that were probably a AA or maybe an A cup. Since I was now very slender from the aerobic workouts, the swell of my boobs was very obvious. I was bejeweled with gold pierced earrings set with large pink gems, a gold chain net which suspended my balls from a gold waist chain and of course, gold nipple rings with a thin gold chain dangling between them. I also had feminine toe and pinky rings, gold bracelets, anklets and a choker necklace, all subtle symbols of bondage.
As I stood there embarrassed in front of them, my cock had grown harder and jutted straight out. Mistress Bella lifted the tip with her riding crop and commented that it had obviously grown at least another inch since she had measured it and that was probably all I could hope for. Speaking directly to Mistress Leelee, she said, "This cock is still pathetic, but it was even shorter and thinner a few months ago. He's been stretching it with weights and a suction pump, but a teeny cock isn't his only shortcoming. Just watch." She bounced my cock on the end of the riding crop, occassionally brushing lightly across the tip from above. In less than a minute, she held her drink glass at the tip just in time to catch my eruption. I could have prevented myself from coming so quickly, but I knew what was expected of me and I didn't want any more swats from the riding crop, so I didn't ignore any of the stimulation or use any of the other tactics I had learned to postpone orgasm.
"wow! That's quick," Mistress Leelee said. Of course, I hadn't come even once for the past few days because Mistress Hannah hadn't been in the mood for sex. I suspected Mistress Bella had requested that for the sake of making this a more memorable event. She swirled the cum around in the glass, mixing it thoroughly with the remains of her Mimosa. Then she handed it to me and ordered me to drink it.
As I complied, she explained to Mistress Leelee. "When you have a man who has so little control, there are some tricks you can use to get better performance out of him. What I did is called 'milking'. He was so keyed up with thoughts of what may happen to him later, that just that little bit of stimulation was too much for him. Now that he's been drained once, he'll calm down and last longer later."
Mistress Hannah noticed that Mistress Leelee's drink was empty and asked if it was time for another round. "Good idea," said Mistress Bella. "Bring mine in a clean glass, slave."
I picked up my tray and collected their glasses, being careful to keep my glass separate. As I poured their drinks, I secretly poured another splash of Mimosa into my glass and washed the rest of my cum down. After serving their drinks, Mistress Bella ordered me to stand in front of her again and resumed speaking to Mistress Leelee. "It's very important when you have a male slave to punish him sometimes for no reason at all. The point is that you control him. Watch." Then she ordered me to "Bend over one half slave." She was on her feet now and delivered two smacks to each ass cheek. As I remained bent, she pulled slowly on the nipple chain until I gasped. Mistress Leelee watched in fascination the entire time.
Mistress Bella stepped in front of me and ordered me to rise and lick her nipples. They were as pink as mine and they poked out from her black leather half-bra. She also wore a corset and open crotch pants which completely exposed her hairy red bush. Stiletto heeled boots completed her ensemble. I licked her nipples, including the vertical silver barbell studs. As I licked she clipped a long thin chain onto one of my nipple rings around my back and to my other nipple ring. After both of her nipples were hard and erect, she ordered me to kneel and kiss her ass, which she turned toward me. After planting kisses on both of her ass cheeks, she sat back on the edge of her chair and ordered me to lick her pussy.
Remembering my lessons from the first time we met, I kissed my way down her leather clad thighs and, when I reached bare flesh, kissed and licked my way down into her hairy muff, beginning at the bottom, and working gradually up. She was quite aroused and I could tell that I was pleasing her. As I had my face buried deeply and my tongue on her hard clit, she pulled something from a bag next to her chair and I heard Mistress Leelee gasp and then giggle.
Mistress Bella ordered me to stop and raise my head. When I did, I was staring at the business end of a big rubber strapon dong. "Suck it," she ordered. I put my best cocksucking skills to work and soon was gagging as she thrust it deeper and deeper into my mouth. Next she stood and ordered me to strap it tightly onto her. "This adds to the humiliation," she explained to Mistress Leelee as I installed the instrument of penetration and adjusted it to her satisfaction. She handed me a tube of lubricant and I lubed the head and shaft. "Now we'll see if you've been stretching that pussy for me. Kiss the carpet."
I placed my face to the floor and my ass in the air as she got behind me and removed my butt plug. Without much ceremony, she pushed the head roughly into me. This dong was the biggest thing that had ever been inserted in my ass and I groaned as it stretched me. She didn't even hesitate as she just kept pushing all of it into me until I felt her leather pants against my ass cheeks. Then she pulled on the chain across my back until my nipples were pulled as far apart as the other chain would allow, which was enough to stretch them quite painfully without pulling the rings out. "This is what you get for being a sissy-boy. My cock up your little ass-pussy is what you deserve for having such a tiny cock and being such a lousy fuck. You are not a real man. You are a pathetic male thing. You have only one thing I can really compliment you on. You are smart enough to know that the best place for you to be right now is impaled on my big fat cock. Now beg me to fuck you."
"Please fuck me Mistress."
She started fucking me, but she commanded, "Keep begging until I finish with you. Embellish it."
"Please Mistress Bella, please keep fucking me. I love your cock. Please fuck my ass. I'm your little sissy fuck boy. Please fuck my ass hard. Oh yes. Oh fuck me hard please. Oh, fuck my ass please." I kept up the patter as she picked up the pace until soon she was slamming into me so hard that her leather chaps were making loud slapping sounds against my thighs and ass. The welts from the riding crop were definitely stinging. With the chain, she was pulling me back to meet her thrusts and then giving me a little slack as she slid her cock back out until I felt the head almost pop out of me. She began to moan as her orgasm hit and her trusts became erratic.
When her spasms subsided, she released the chain and pulled the big dong from me, sliding the butt plug in and then slapping my stinging ass with the riding crop to make me grip it. Next she unclipped her chain from my nipple rings and slapped my ass one more time with the whip. "Now that's what you do to a sissy-boy. Next!" she said as she handed the riding crop to Mistress Leelee.
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<a href="https://www.lushstories.com/stories/crossdressing/mistress-hannahs-pathetic-husband-part-3.aspx">Mistress Hannah's Pathetic Husband Part 5</a>