Step-Mother has a Secret

In time, he discovered that he had first a fascination then second a love of transsexuals. He told her that he had seen me dancing topless at a gentleman's club. They both looked to me instantly with the realization that I am their transsexual stepmother. Jerry's face grew a bit ashen. He and I had had a great relationship and we certainly hoped that wouldn't change. Kelli's face lit up with a smile that I immediately noticed - not quite the reaction I had expected.

Richard had been very successful in his professional life and money was no longer a concern. He kept his fingers in the art world a little bit but keeping our house running smoothly was now his primary objective. Richard is 6'2" and very fit. He has a gym membership and he goes at least four times a week to maintain his health and physique. His grey hair is neatly trimmed and accents his sky blue eyes. Richard begins every week with a mani/pedi and a body waxing to keep his chest, pits, legs and privates very soft and smooth. I love my man smooth and feminine and Richard never wishes to displease me.

When it was apparent Richard had said what he needed to say, Jerry stood up and crossed the floor to give his father a hug. I am a transsexual - his stepmother is a transsexual. And his father is a cuckold. Kelli paused a bit before standing up and giving me motion that maybe we should give the men a few minutes alone. I was surprised when she took my hand and led me from the library. We closed the door behind us and she immediately headed to the bar, pouring two glasses of whiskey with ice.

I honestly had no idea what she was thinking or would say. Kelli clinked glasses then took a healthy swallow and I did the same. "I knew ... I knew there was something about you, Michelle. We are kindred spirits. I just couldn't put my finger on it until Richard started speaking." I broke into a smile, the tension I was fearing never existing. "Now, can I tell you a secret?" and Kelli proceeded to blow my mind with her own revelation.

Kelli and Jerry have been married for 12 years. For all but the first two years, Kelli has been the Dominant and Jerry has been her cuckold subbie. The first few years it was just the two of them with Kelli learning what worked for the two of them to achieve the greatest mental and sexual satisfaction. About five years into the learning, Kelli started fucking other men while Jerry was at work then she began leaving him home in the evenings as she went on sex dates.

I must admit that I was finding myself quite shocked to hear about their relationship. I never would have guessed by any of our interactions, or even how they act when with us. I wondered if Rachel knew anything about them. "The apple doesn't fall far from the tree ... " I repeated what Kelli had said when Richard had first told them. We both laughed out loud and swallowed our second whiskey's.

We realized it had been nearly forty-five minutes since we exited the library and decided we should check up on the boys. They were sitting on one of the leather couches sharing whiskey's as well. With the library door closed behind us, Kelli announced our presence with a booming voice. "Cuck! Stand up and display yourself." Jerry's head snapped towards his wife's voice. He hesitated only briefly before setting his glass on the oak table and standing up. His father looked at him with great surprise.

Apparently this had not been discussed at all. Jerry unfastened his belt and unzipped his slacks. He wore babygirl panty's and he pushed them down to reveal his penis caged tightly in steel. "Now turn to show your father the son he has raised." Jerry turned without hesitation and I could see the stripes on his ass from where he had been beaten. He presented his caged penis to his father. I allowed Richard a look to see his son before speaking to him.

"Richard, stand up and show Kelli's cuck your own penis." Richard turned and looked at me as all the blood drained from his face. I am sure he did not expect this, nor did I when the afternoon began not that long ago. Jerry was standing there in only a sweater and dress shirt covering his torso, his pants and babygirl panty's around his ankles as his father slowly stood up after setting his drink on the matching oak side table. He looked at me once more as if to confirm I was doing this right now and my expression left no doubt. Richard fumbled with his slacks and unzipped his fly. He let his slacks drop to the floor around his loafers. His own caged penis glistened in the canned lighting of the library. The steel was wet from his arousal at telling his story, the cage keeping him quite contained. Richard reached under his sac and cupped himself to show his penis to his likewise caged son.

It was obvious Kelli and I shared different variations of the same relationship with our respective husbands. She turned to me and asked if she may inspect Richard and I agreed. The two men, father and son, both cuckolds to their wives stood just eighteen inches apart from one another as Kelli approached them. She fondled Jerry's caged penis with her left hand while reaching out and fondling Richard's with her right hand. Then she laughed at them both. Richard blushed bright red at this form of humiliation. Jerry seemed stoic as if he had endured much worse. Kelli pressed her mouth to her husband's and kissed him quite intimately as she continued to stroke them both then broke the kiss to whisper in his ear. He pulled the sweater off over his head unbuttoned his casual dress shirt underneath. He revealed a matching bra to his babygirl panty's.

I walked out of the room to find our housemaid, Catalina, and let her know that she was excused for the afternoon. Ever the diligent one, she explained that she had not put the late lunch on the table as we had asked earlier in the day. I told her Kelli and I would take care of it and we would like her to leave immediately. She gathered her things and thanked me for the early evening. Once she had left, I bolted the door so she would not return unexpectedly and returned to the library.

Richard had removed his polo shirt and now stood with just his pants around his ankles. They all turned to me as I entered, leaving the doors open behind me. "Richard, you may finish undressing and Jerry you should pull up your panties then go to the kitchen and set the table. Catalina has left us for the evening and you two will take her place tonight." The two men did as they were told and walked past in bare feet. I joined Kelli at the bar as she poured us both a third drink. We turned shoulder-to-shoulder and watched them set the table and present the dinner of lasagne, fresh bread and wine.

As a departure from our usual Dominant/subordinate time, I told Richard he may speak freely throughout dinner as if Kelly and Jerry did not know a thing about us. Kelli let Jerry know he too could speak freely. Surprisingly, dinner was a lively affair perhaps all the whiskey before dinner and the wine with made everyone's tongues a little looser. At some point, I mentioned the somewhat fresh stripes on Jerry's ass and Kelli said that she believes in a firm hand when mistakes or digressions occur. I had never felt this way with Richard but perhaps this was because we both came to this place from different starting points. Kelli and I got quite the pleasure watching the boys do the dishes and clean up after the meal. It was getting late on the Sunday so Kelli instructed her cuck to get dressed for the drive home. I could see Richard wanting to get dressed but I did not give any instructions. We hugged, kissed good bye and made plans for the following Saturday afternoon at Kelli's home.

As soon as I saw taillights in the drive, I instructed Richard to get the lube and to ready himself in the library. I was so fucking horny from all that had unexpectedly happened this afternoon and evening and I just wanted to fuck. I gave him a couple minutes to prepare himself then walked into the library. Richard was still nude and wearing his cock cage. He was on the solid oak coffee table that we had sat around earlier as he told his only son that he is married to a transexual and she dominates him by their mutual choice. His hands gripped the edges at one end, his knees on the wood with legs spread wide on the other end. His asshole gleamed from the lube, the tube now laying on the floor. I slapped his ass playfully as I walked past him.

I used the remote to power on the three video screens that had been concealed by art on the wall before him. On the left screen was a feed for transexual dominating a male video. On the right screen was a feed for lesbian sex on video. And the center caught him totally by surprise. It was a split screen of two photos - one showed Rachel from our encounter standing nude just after I had fucked her while Richard watched; one showed Jerry standing in the babygirl panty and bra set after dinner. I walked behind him and told him not to look away from any of the screens as I reached under him and felt his cock cage. He was dripping wet with his cock nearly bulging at the seams of the steel.

"So Daddy has told his dirty secrets to his children I begin," as I move behind him and press my erect cock to his lubed asshole. "And it seems both your daughter and son had secrets of their own they had kept from you but now you know them." I thrust and Richard grunts then pushes back to me as he knows to do. I thrust again, my cock long and thick penetrating deeply into his sphincter. He feels so tight tonight, it seems we are both quite aroused from what we learned.

"And what does Daddy think knowing his son following his daddy's footsteps to become a cuckold sissy?" I ask with my cock buried deep in his asshole. I fuck in and out, my ball sac swinging loosely after my tuck all afternoon and evening. The feeling is electric as I think about what Kelli had told me in the time we sat alone. Richard grunts with each thrust, feeling how hard I am tonight as the video plays before us and the images of my step-children look at us.

Richard doesn't answer for two minutes while he enjoys my fucking. I am sure he is staring at the two pictures in the middle screen. Finally he responds between my thrusts, "I am not surprised. His mother always did coddle him and it seemed Rachel would bully him from time to time being his older sister." Richard groans as he seems to collect his thoughts. I reach around and caress his exposed ball sac and rub my fingers over the steel as if stroking him. My hand is immediately wet and sticky from his arousal. This table was custom made for my height for this exact purpose. I held his left hip as I fucked, my sac swinging as I could feel myself nearing orgasm from the night and Richard's tight hole.

"If he is happy with Kelli and his life, then I am happy for him. As I am happy to be with you, my love." As he says this, I cry out and shoot my cum deep in his bowels. I thrust wildly pumping my cock and filling his asshole with my sticky hot seed and then I slouch over him. My 38D's pressing into his back as his arms wobble a little bit to hold me up with my cock still buried inside him. I ask him if he wishes to orgasm and Richard cries like a little puppy dog. I fumble with the key without seeing the lock then set him free. I stay inside him as the cage rattles to the table. I tell him he may touch himself and his left hand quickly takes his cock. Richard begins jerking frantically while I tell him how tight Rachel's cunt was when I fucked her. His body shakes when I mention Jerry's caged penis and the whip marks on his ass. I tell him he must cum in the empty whiskey tumbler still on the table.

Richard jerks and shoots as I hold the tumbler's mouth around the head of his cock. He shoots a second stream then whimpers. I know he's done when he whimpers like this. I pull out my cock from his asshole and he clenches tightly to not make a mess. I hold the glass up to the light and see that my husband had quite the orgasm thinking about his offspring while being fucked by his wife. I walk around, my big cock flopping and dripping to present him the glass. Richard tilts the tumbler and drains the sticky goo into his mouth and then I tell him to put his penis away for the night. Richard fastens the cock cage and clicks the lock.

##

Monday morning felt like not only a brand new week but a brand new lifetime. I reflected on the past couple weeks since that terrifying afternoon in the changing room with Rachel and smiling at how amazing it all seems to be working out for Richard and I. He was quite surprised when I woke him up by giving him an amazing blow job. I had unlocked his cock and had him nearly erect before he fully awoke and realized it wasn't a dream. I sucked on his smooth cock for only a couple minutes before he touched my shoulder to let me know he was about to cum. To his second surprise of the morning, I let him ejaculate into my mouth and I swallowed most of his cum. I honestly like the taste of his cum, but I can't let him have this pleasure too often. I climbed up his firm torso, my nails raking his skin as my huge tits dragged along his flesh. My mouth pressed to his and I kissed him with his cum still on my tongue. Richard took it from me as we kissed.

I made us just a little late but Richard had our breakfast ready and I was soon out the door to the office. Richard's Monday takes him an hour away to three towns south for his weekly mani/pedi sessions with Mai and then to the waxing studio with Tina. Both women are well compensated for their services and their silence, especially Tina. It's not all that uncommon these days for men to have mani/pedi's but Richard still gets a little bit flustered when she slips off his loafers and tends to his feet. As for Tina, she is actually an old friend of mine and she knows exactly what I expect. Richard has come to think of her as a girlfriend too, usually bringing her lunch for them to share either before or after his session.

For his session, Richard will strip nude and climb on her table with only his cock cage. His pits, chest and tummy, legs and back are all waxed. He also gets a manzilian, or the male equivalent of the brazilian for women. As I've said, I like my man to be smooth and soft and Tina is the best. She will sometimes play with balls and cock cage while waxing him. She always leaves Richard frustrated from the teasing and I just love her for it!

Kelli and I exchange calls and texts all week, setting up the weekend getaway to her home and the ability to consummate this new discovery of family. I have kept Richard mostly in the dark about my plans other than to tell him we are visiting his son and Kelli on the weekend.

Saturday has finally arrived and it has been a long week of anticipation. As aroused as I've been, I've not had a single orgasm. I've wanted to be ready for whatever happens with Kelli and Jerry. I have been naughty and edged poor Richard every night only to force him back into his cage without nary an orgasm since my Monday morning blowjob. A driver takes us the thirty minute journey to Kelli's home in the country. We have brought along two suitcases, both filled with various outfits depending on mood for Richard and I. I would have brought along toys but Kelli assured me that wouldn't be necessary - Kelli's playroom was quite well stocked.

The kids property sits on ten acres. It's a ranch style home with a large pool and deck out back. The nearest neighbor is over a mile away in any direction. We have been there many times but had never been made aware of the one significant addition Kelli had built after year two of their marriage. A 2,000 square foot dungeon built adjacent to their home. It's accessed either by a hidden door off the pool utility room or by a hidden staircase near their mistress bedroom. Before we left today, we would be made aware.

It is just after noon as we ring the bell. Jerry opens the door and I'm sure Richard is just as surprised as I am at what we see. Jerry is wearing a two-piece bikini, long blonde wig and five-inch heels. He is wearing beautifully applied makeup and actually looks quite attractive. His bikini top has greatly exaggerated fake breasts and there is the requisite bulge in his bottoms from his cage. "Mother, Father ... welcome. Do, please do come inside. My Mistress awaits you both." I am still a bit shocked as we both walk inside and Jerry closes the door behind us. I had texted and talked with Kelli three times during the week as we decided logistics for today but had no idea my stepson would greet us as a large breasted bimbo.

Kelli strides into the room wearing head-to-toe leather. Apparently today she is full-on Dominatrix and already I am deciding what Richard and I shall wear. She and I embrace more warmly than ever - a new level of friendship has been reached. She hugs her father-in-law Richard warmly then whispers into his ear that this will be the last time for today that she treats him as family. She pulls away from him and he obediently lowers his gaze. Kelli says she knows I'm at a disadvantage in her home and quickly has cuck show us to our room so we may change. She says they will be in the back and to join them when ready.

I ask Richard what she had said to him once we are alone. He quietly tells me that Mistress said she looks forward to fucking her father-in-law. I smile at the suggestion. Richard is standing nude when I tell him to bend forward. I did bring one device packed in his suitcase. A modified humbler. It has a deep curve that allows Richard to stand partially straight without the harsh tug on his ball sac that a standard humbler does. I want Richard to be able to move about yet still be constrained. I lock the humbler in place with his balls captured nicely behind him. He slips low open-toed heels onto his feet so his painted nails are displayed, I have decided to wear a leather bustier that pushes up my 38D's without concealing them at all. My thick nipples are already firm and the day hasn't truly started. I wear a leather thong that has a sleeve for my cock to fill. I am sure my cock has been greatly discussed by these two all week. A leather skirt partially conceals the cock sleeve but leaves little to the imagination. And heeled, knee-high boots to accentuate my thighs.

We walk out to the patio to the sound of applause by our hosts. I tease by lifting my skirt and I see Kelli's eyes flash over my stuffed thong. I note that cuck has pulled his bikini bottoms under his ball sac so his cage is now displayed. I have Richard turn around slowly to show off his backside and the modified humbler. His balls now a brilliant shade of red. Kelli squeals with delight then walks over to investigate. Her hand caresses his cheek then reaches down and squeezes his ball sac as Richards muffles a cry. She releases his sac and runs her hand over his torso noting the angle of his body from wearing the humbler. She remarks she will just have to get one of these for cuck.

As Kelli fondles her father-in-law, I move behind my stepson-in-law and rub my leather encased erect cock against his bikini'd backside. My hands reach around as if to grope his as big as mine tits. I press my lips to his ear, slipping under the long blonde wig and whisper, "I bet you have a wonderfully tight asshole and your mother is so very big and hard." Cuck shudders against me as I whisper to him.

"We have a surprise to show you both but first some iced tea for such a warm afternoon?" Cuck returns with a silver tray holding four glasses, a pitcher and a silver sugar bowl. Two of the glasses are of the eight ounce variety and cuck hands one to both Kelli and myself. Two of the glasses are much taller, twenty ounces each, and these are for Richard and cuck. Sugar is added to each without asking then cuck hands one glass to his nude father standing nearby. When I look to Kelli about the sugar, she laughs softly then adds "I've learned that sugar stimulates glands in the male body that accelerates the functions of the kidneys." Poor Richard, I think to myself. Being 63, his bladder is not what it was when he was a younger man. This could be very interesting, and messy, to say the least.