From Cucked Husband to Sub Wife Ch. 27

Chapter 27 New Lambs in the Fold

The Samuelson dinner was just a few days away, and we were excited about the prospect of cucking the scion of an old blue blood New York family. We had our regular cleaning service come Thursday before the big dinner, and I got to shop for a new outfit. Friday, I left work early so we could be fully prepared. Angel came with me; despite her crazy unconventional look, she had a really great eye for fashion, and we had become bosom girlfriends.

We had a lot of fun shopping fancy boutiques uptown and chic and trendy ones downtown. I was looking for something very specific. It had to be sexy, but not too much, fun but stylish. I had to draw out Ashley Samuelson to broach the subject.

I picked up some super sexy lingerie (a girl could never have enough) and finally found the perfect outfit for the dinner. It was simple black dress that revealed all of my assets just perfectly while still being totally classy, and would cover up most of my breast markings (which we feared might put Ashley off, if she saw too much to soon). I got a pair of black pumps to go with it. They were all very expensive, but totally worth it.

After the shopping, I had spa day, while Angel accompanied me—drink in hand the whole time. She wasn't really "a spa kind of girl," she said, "more of a spa voyeur." So, she just watched, while I was being massaged, pampered, waxed, facialed and mani-pedied, with a never empty gin and tonic in her hand regaling me with stories of adventures both with and before Bob.

I got home to the wonderful aroma of Vera's dinner preparations. Vera was wearing a very smart French chef outfit and Bernie was dressed as a waiter. They looked cute as a button, but I had my doubts about Bernie's ability to pull the thing off. I showered, cleaned and primped myself inside and out. Daddy got home just as I was doing my makeup in my dressing room. He popped his head in to see how I was progressing.

He had actually made an effort, which was unusual; it was hard to get him out of black tees and chinos. He had gotten a haircut and a shave and had on a casual jacket but a black tee under and a pair slacks. He was looking so tasty that I suddenly felt a pang of jealousy. I was setting up my man to have this hot rich bitch as his slut; what the fuck was I thinking? But I caught myself before going too far down that road.

Though I knew he really didn't like it so much, I made him kiss me deeply and passionately before I put on my lipstick. I was trying make out hot and heavy, and he was trying to squirm out of it. But I grabbed his head and held him into mine, until I was satisfied. Just as I let him go, I realized what I had done, but he seemed to understand that every once in a while, I needed a bit of control.

We were all ready, looking dapper and sexy, when the intercom buzzer went off just on time. The Samuelsons were soon at the door. I opened the door with Daddy next to me with his arm around my waist. A tableau of conventional domesticity, we went through the customary exchanges.

"Good evening, Jake and Ashley," I said, "this is my fiancé, Jordan James Jenkins. Honey, this is Ashley and Jake Samuelson."

"Come in, come in. Very glad to meet you both." Daddy said graciously. Reached for Jake's hand and engulfed it in his, reached with the other arm drawing Ashley close and pecked her on the cheek casually.

"Oh, thanks for inviting us, lovely to meet you," Ashley purred.

I could tell from their attire that they too had gone to some trouble preparing for our date. I had thought Jake looked good for fifties, but he was actually 63, and his wife 37. She looked stunning in a rich royal purple fitted-coat, and when she took it off, she had on a yellow silk halter top that accentuated her generous globes and tight little skirt that struggled to cover her enviable buttocks and accentuated her long shapely legs.

He was wearing a tight gray flannel suit, but the jacket had brocaded panels of colorful faux paisley. He wore a long muffler and a long leather frock coat over it. He looked like an even more eccentric Sherlock Holmes. It was clear that unlike my man, Jake was a big fan of fashion. He was not unhandsome, but though taller than average, he had very delicate features that made him seem like a smaller man.

I very carefully watched her reaction to Mr. Jenkins to get a read on her. Her response was a lot like Lori's that first day at the PT clinic. This was a good a sign. I would have to get her alone to further gauge her interest. We had decided to allow them to think we were swingers and progress gently from there to where we really wanted to go. We moved into the living/dining room area near the kitchen.

They complimented the apartment, though I was sure they had something even more extravagant than ours. It still amazed me that this was my home, now. I grew up within walking distance, but it might as well have been a galaxy away. My mom and I lived in a one-bedroom walk-up (really a studio cut in half to make the bedroom), and now... we had rooms, as big as that apartment, which I had seen only a few times since I had moved in.

We sat down to drinks and again, neither Jake nor Ashley stopped checking me out, though now they seemed to alternate between me and Daddy.

"So, how did you two meet?" Daddy posed, knowing almost every detail full well from my telling and the Internet.

"Well, we worked together at Jake's foundation; I helped set it up. I can't say it was love at first sight, but let's just say he wore me down. We've been together, what is it, Jake? Six years?"

"Yeah, about that. I didn't have to wear you down all that much, as I remember, sweetheart. Hee hee hee."

"Oh, shut up, you're lucky I gave you the time of day, you old geezer."

"Hey, I'm still not too old, ha ha ha. So, about you two?"

"That's a bit complicated," Daddy put in and changed the subject, "So, Jake, I know your grandfather was in railroads, but what does your company do these days?"

"Yes, Jordan, that was great-grandfather, but we diversified long ago. We are mostly a capital equities firm now. We buy or takeover problematic companies and either liquidate their assets or turn them around. I say we, but I don't really have much to do with the day-to-day anymore. Ashley has more to do with it, and she mostly works on foundation stuff, which is where our real focus is these days. I don't even sit on the board anymore, and Ashley's seat is mostly ceremonial, like the Queen. But that's just boring stuff. What do you two do for fun."

I worried this line of questioning too would present problems this early in the conversation, but just then, Vera came out of the kitchen to declare dinner ready. I motioned Ashley to go "powder our noses" together, and we excused ourselves and went into the powder room across from the dining area. It was like the rest of the apartment huge. It was set up for large parties, so it had two stalls and two sinks and sitting area with vanities.

"Oh, my God, you got so lucky with that Jordan. He is just gorgeous! What's he like... you know, ahem... erm... downstairs."

"If you think I got lucky upstairs, you have no idea how lucky I got downstairs."

"Oh, my, my! Do you mind if I ask you a personal question?"

"More personal than my man's penis size?"

"You've got a point, but, actually, kinda, yes. You are trans, right? Not that you are not gorgeous yourself and sexy as hell too. I'm just curious."

I had considered this question before. At this point, I had met quite a few trans people at different points on the spectrum. Many, maybe most, had said to me that they had always known. For me, it was different, because it came as a shock. I thought myself happy enough in my assigned gender. But regardless of how I got here, I realized a long time ago that that was wrong. I was much happier, braver, more confident, and emotionally better-adjusted as a woman than I had ever been as man. Even with our very unconventional relationship.

As a man I was a wimpy nerd, regularly bullied by bigger guys. I had one friend in high school, who proved to be not much of one and a "girlfriend" who wasn't much of that either. I was married to a woman for six years with no idea of how she really felt about me or how she was fucking everyone within a fifty-mile radius, including my one true friend, Joe. Yes! I thought. I was definitely not really happy in my assigned gender and trans the whole time, I was just too repressed and in denial to realize it. Until He came into my life.

"Yes, I am, Ashley. That's not so personal; it's just who I am. I am not ashamed of it."

"So, do you still..." She wiggled her finger in pantomime.

"Well, not much of one, and not for much longer; in two weeks I am having the last surgery."

"Oh, WOW! That's amazing. Well, you look delicious. You have to give me your plastic surgeon's number for future reference."

"How about Jake? I mean... uhm... downstairs" This was the question that might seal the deal.

"Him? Well, dear I'm afraid I'm not as lucky as you, upstairs or down. He's sweet enough, but he's not so virile. He's kind of small and likes me to peg him." Excellent! I thought.

"Oh, well poor you, huh?"

"Can you keep a secret?"

"Of course!" I made the lips locked and throwing away the key gesture.

"I've hired out guys off the internet. I think he must know I sleep around, but I don't tell him. I couldn't have an actual affair on him; that would be a PR nightmare. So, I go to a different city, check into a cheap motel, and hire one these guys."

Bingo! This was the trifecta: he was small, unvirile, and, though she didn't think of it that way she was already cheating on him.

"Hmm, well, Ashley, I believe we may be able to help with that, but it may be a bit different from what you imagine. Let's go in to dinner, and we'll talk more. Do you promise to keep an open mind?"

"Oh, now I am intrigued! Sure!" She cooed with a big grin.

When we got to the table, Mr. Jenkins and Jake were sitting next to each other at the head of our ridiculously large table, and there were two place settings on either side. They both stood up gallantly and pulled out our chairs; I took the side next to Jake, to give Daddy a chance with Ashley, while I distracted Jake. Ashley was staring hard at him from the moment we sat down. Vera and Bernie came with the first course, which was this incredible French fish soup.

As I talked quietly with Jake on my side, I kept an eye on Ashley and how she was leaning toward Mr. Jenkins. I was pretty sure she had her left hand on his leg under the table while she ate the soup with her right. I was purposely whispering to keep Jake's attention on me. While Daddy worked on Ashley. I couldn't quite make out what he was telling her, but she was blushing with almost every word.

Jake was whispering how sexy he thought I was, and intimating how much he would like to suck on my perky titties. I decided to give his leg a squeeze myself to keep him interested. At this point, I thought our success imminent. I said, in a husky whisper, "what would you be willing to do to for that, Jake?"

"What do you have in mind?"

"Oh, we'll get to that. What do you think your wife would be willing to do to have a go with my man?" We looked over to her; she was looking at Daddy like a tigress eyeing a tasty antelope.

"A great deal, I believe, my dear!"

I got Daddy's attention and gave him the signal that maybe now was a good time to bring up the subject. I was pretty sure she had made her way to his big cock because of the lust in her eyes; and he looked like her manipulation was having some effect on him too. When he finally caught my eye, I nodded, and he straightened up and so did Ashley who was listing about 20 degrees to the left of center.

"Shall we adjourn to our sitting room, where we can get, uhm, more comfortable." They almost leapt off the table. Daddy ordered drinks from Bernie, "what would you like, Jake?"

We moved to the sitting room just next door to the playroom, a very comfortable room, though a bit stodgy; most of the furnishings left over from the Smiths. It had two large comfy overstuffed chairs and a backless settee, which had often proved useful. We sat in the chairs and the Samuelsons on the settee. Daddy switched effortlessly from attentive host to commanding the room.

We were sipping our drinks casually, when he asked, "may I ask you a personal question, Ashley? She just nodded for him to continue. "When was last time Jake made you come with his cock?" Jake stiffened and scrunched up his face as if he had been slapped, and, for a moment, it looked like all our preparations might be for naught.

"Never..." She said quietly, almost to herself. Mr. Jenkin's tone made one want to be as honest as possible, even as he asked painful questions—this I could attest from personal experience.

"Speak up, dear, what was that?" He demanded confidently.

"Never! He's never made me come with his tiny dick. Sorry, Jake, but I'm pretty sure you know that, don't you? Why do you think you have to fuck me with a dildo after?"

"No, no... I didn't know that! I know it's small, but I thought you enjoyed it." This "new" knowledge threw Jake off. He had been at the point of umbrage, having heard the question. When Ashley answered, it was like the air let out of a balloon and this tiny shrunken man.

"Oh, I never enjoyed it enough to actually make me come. Sorry, honey." She touched his leg gently. This whole thing was starting to feel very familiar to me. I identified with poor Mr. Samuelson. Out of instinct, and to help soothe him through this rough part, I got up from my comfy chair and knelt next to him and caressed him, as Daddy was about to destroy his ego, so he would understand why he had to give up trying to sexually satisfy his wife.

"That must be hard to hear, Jake, old man, but you had to have an inkling about it, my friend. Didn't you?"

"Yes, you are right. I have had this problem all my life." It began to feel like couple's therapy.

"Do you mind if we see? Show us what you got to work with, Jake? Let Michelle help you. My dear, help him undress." His command made one just want to do as he said. Jake stood up and started taking off his belt; I helped him remove his pants. I sat him back down on his skinny naked butt and took of his shoes and socks and peeled his pants off. I knew Daddy wanted him completely naked, for effect, so I helped him off with his top half too. I was super gentle with him; touching him affectionately, as I helped him strip.

Ashley sat stone still with her jaw gaping wide, as we did this. There were tears in her eyes, but she was not crying, per se.

"That... is rather small, Jake. Maybe you're just nervous. Michelle, dear, help him relax. You don't mind if my sissy helps you... erm... relax."

"Oh, no, indeed!"

I sat him back down very gently and kissed him tenderly at first then more forcefully. I pulled down the front of my dress and offered him one my breasts to suckle on. He was half sobbing and whimpering, but he enjoyed suckling my tits. I reached down and fondled his little guy. He was probably not much bigger than I was at the start of my transition.

Then, I engulfed his little dick and sucked on it like a popsicle. I lifted it up and licked his balls, then I lifted his leg; and, while licking his asshole, poked a finger or two in, and stroked his wee dickie. Despite his recent emotional turmoil, or perhaps in part due to it, he was really excited; his tiny cocktail sausage was engorged, and by the time I got it back in my mouth, he was coming. I looked into his eyes as he came and watched them glaze over.

He moaned and sobbed at the same time, grimacing and shuddering as he came. Although it took so little to get there, he was experiencing a very intense and emotional ecstasy. I tried to signal sympathetically with my eyes that it was okay. That everything would be okay. I held him in my mouth until he stopped coming. Holding his small load, I opened my mouth, so he could see it, then turned to show Ashley and Daddy. I turned back toward him and swallowed the whole it in one gulp.

I smiled sympathetically and licked my lips to reassure him. The taste was not bad, just little bland and runny. I tenderly held and kissed the rapidly shrinking wiener, and took his hand in mine and kissed it gently. I turned up my face and pulled him down to kissed him tenderly. I was trying to comfort him, knowing exactly how he felt, and what was to happen next.

"Oh, boy, Jake. That was not very long. Surely, he took more time with you, Ashley, dear?"

"No..., that's pretty much it, right there. Sometimes, I barely get him in me, and he's spurting. I don't ever blow him, he would come just like that."

"So, Jake, you thought your wife was satisfied with your tiny pecker that spurts before it ever gets in her? How did you think that would work, buddy?"

"Yes, yes, of course I knew, I'm sorry, honey. You deserve better."

"Hold that thought, Jake. Michelle, come here and help me show them something." I went back to him and helped him take of his jacket and top, then his pants; he kept his boxers on, for now. But the outline of his big beautiful cock was definitely visible through the material, and there was clear evidence of how much he was enjoying this. When I moved away and they could see it, the Samuelsons gasped audibly.

"You like what see?" Oh, hell yeah... they did! They both nodded their heads enthusiastically.

"Sissy, come here!"

The first phase of our plan was more or less accomplished. Jake was ready to be cuckolded by my fiancé and Master, but there was the whole domination side that we had yet to broach. We had to walk a fine line, here. Once he was cucked, we could work in the other part later, but if we scared them away tonight, we could lose the whole deal. I knew by his tone he wanted to proceed, tonight. I was a bit nervous about it; Jake was very sensitive.

I walked over and knelt at his feet and put my hands behind my back. "We're ready for the next demonstration. Jake, I want you to undress your wife for me, please? Take your time; do it sensuously. She's a good-looking woman; use her to seduce me; show me her assets, Jake."

Jake was tense and nervous; his hands shaky, and he seemed nailed to the spot. I knee-walked over to him, took his hand and placed it on my perky tits. He looked down on me and smiled.

"Master gave you a command; you should respond, sweetie." I whispered in the softest, kindest tone I could muster.

"Y-y-y-es? Sir?" He finally whispered in tremulous voice barely audibly. His wife was throwing daggers at him with her eyes, but said nothing.

"What was that, Jake? Did you say something?"

"YES, Sir." I led him over to Ashley, still on my knees. He reached out to her, stood her up in front of the settee, and began to do as instructed.

As Jake was doing that, I made my way back to Daddy; he had me raise my arms and lifted off my new dress. I was left with nothing but my pretty panty and bra set and pumps, all black. They could see my body, still ravaged from recent activities. I'm sure they saw we were more than just swingers from the evidence written in welts and bruises on my back and tits.

Daddy stood up, and I used my teeth to pull down his boxers for dramatic effect and when it finally came out, they both oohed and aahed behind me. He angled my head up, had me open my mouth wide, and spat in it, then aimed his big cock to drive that massive beast all the way down my throat in one fell swoop. I was ready for it, but I was still gagging and choking from it; I didn't panic and let it just freely take over my throat, as I had become accustomed.

Our audience gasped at the feat. I felt like a sword-swallower at a side show, and I was proud of the accomplishment; it had taken a long time to be able to take his cock in like that. Whenever I could, I glanced over at the Samuelsons; Jake was following instructions dutifully. He removed Ashley's clothes one piece at a time with devotion and total concentration.