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Tango on the Razor's Edge Ch. 07

Story Info
A crossdressing cuckold has a play date with a new friend.
6.8k words
4.38
10.5k
7

Part 7 of the 20 part series

Updated 06/10/2023
Created 11/24/2020
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I woke with Holly's head resting on my chest and her arm wrapped around my side. I held her there, afraid to move, as I savored memories of a time not so long ago when I routinely awoke in her embrace. This was the first time I'd slept with her in almost a month, and I wondered if I would ever be the man in her life again. She sleepily brushed a hair from her nose then pulled her body closer to mine, snuggling in for a few more moments.

I drew the long slow arcs on her back that lovers make when thinking about how happy they are. As I did, she slowly stirred. Her fingertip played with my nipple. She kissed it and said, "I'm so proud of you."

"You are?" I asked, hopefully.

"Of course, You're the perfect wife."

Deflated, I kissed her forehead and replied, "Thank you for letting me have this role in your life." I'd hoped that she would look up so that I could kiss her lips, but her head stayed down as if she was inspecting the lines that her fingernail traced along my sternum.

I laid back and enjoyed the soft attention she was paying to me. Her hand wandered around to my nipple, pinched it hard, as she knew I liked, and then meandered to the other nipple and pinched it as well. With my cock caged, there was little else she could do without getting the strapon, so I rolled her over and kissed her on the lips. We kissed each other intensely for a long moment; then I released her lips so that I could kiss her neck.

She put her hand under my chin and said, "Hey, there's something we need to talk about."

I moved down a little further, kissed her erect nipple, and said, "You talk. I'll listen," as I sucked her breast into my mouth.

She lifted my head with her hands and said, "No, I need you to look at me."

I kissed her nipple one last time and looked her in the eyes. "I'm all yours."

"I know. That's part of the problem. Dan is really jealous of you."

"You're kidding, right?"

"No. He saw the mess we made in my office yesterday, and he wants it to stop."

"He's fucking my wife, and he's jealous?"

"Yeah, I know. Bulls are hard sometimes. The point is that you can't go down on me anymore."

"I went down on you last night."

"I know. I should have stopped you, but..."

"How is he ever going to know?"

"That isn't the point. Dan wants it to stop, so it has to stop."

"What if I said you can't fuck him anymore?"

Holly softly caressed my cheek, "Oh, Baby, you're in no position to do that."

I rolled away from her and said, "Jesus, Dan was right."

Holly got up, put on a silky black robe. While inspecting herself in the mirror, she asked, "What was he right about?"

"He said I'm nothing to you."

"Don't be like that. You know this is what you want. You're a princess. You want us to treat you like a princess."

She hadn't denied it, which meant it was true. Once Dan sold his company, she'd run off with him and his money, and I'd be left with nothing but a feminine wardrobe. Holly must have read my expression. She kissed me softly on the lips and said, "Trust me, please?"

"I wish..."

She stood at the foot of the bed and waited for me to finish my sentence. After a long pause, she asked, "You wish what?"

"I don't know. I guess I wish I'd been smart enough to avoid this situation."

"Oh, come on. You're having fun."

I exhaled. "I'm losing you. That's not fun."

She wrapped her arms around my head, drew me in close to her body, and hugged me against her taut stomach. "Sometimes, the only way to keep something is to let it go."

I wrapped my arms around her waist as I inhaled her sweet scent, afraid that this might be the last time I held her. "That's just the bullshit people tell themselves after a breakup. Once I let you go, you'll be gone."

She smiled with compassion I hadn't seen in weeks. "Do you remember when you were young, you would run across a stream by jumping from one stone to the next? If you ran fast enough, your momentum would carry you across, but if you hesitated, you'd fall in?"

I could visualize crossing a creek in my mind, but I had no idea what she was driving at.

"Well, our situation is a little like that. Right now, you're in the middle of a transition. It's like you're in the middle of the creek jumping from stone to stone. You'll get across if you keep moving, but if you stop and worry about all the things that might go wrong, you'll lose your momentum, and you won't be able to take the next step. You can't let that happen. You've got to let go of all the crap that's holding you back and press on."

I shook my head. "I don't have any idea what's on the other side."

Holly smiled reassuringly as she combed her fingers through my hair. "I'm on the other side. Come join me."

She let me embrace her for a few more moments, then she said, "We've gotta get going," as she pried herself from my grasp. In the span of a moment, her mood shifted back to the domineering mistress that I'd grown accustomed to. She said, "Go downstairs and fix me a poached egg on toast."

***

Later that morning, I was on the shop floor with Raul when Holly called me to her office. Once I'd joined her upstairs, she bid me close the door. For an instant, I'd thought she'd changed her mind and wanted me to go down on her, but she had me sit on the other side of her desk. She said, "I just got off the phone with Darlene. She has a new dress, and a matching pair of heels that she thinks will be perfect for you." She passed me a scrap of paper with the address and said, "She's waiting for you."

"You want me to pick up the dress at her house?"

"Is that a problem?"

"Won't her husband be there?"

"I suppose. Why?"

"This is just another setup, isn't it? You want me to have a sissy playdate with Darlene's husband."

Holly laughed. "I just want you to pick up the dress."

"No. This is just like the shopping trip. You're setting me up again."

She smiled like a parent might smile at a confused child. "I just want you to pick up the dress, but you have my permission to have a sissy playdate with Darlene's husband if you want."

"That wasn't what I said."

"Oh, I heard what you said, Baby. I understand that you're horny, and you want a little time with another sissy, and I think it's good that you're embracing your feminine side."

I was at a loss for words. Somehow she'd twisted everything I'd said. Rather than battle on, I made a tactical retreat. "I'll pick up the dress on my lunch break."

Holly replied, "That's a good girl." With a subtle shift in her demeanor, she added, "If you're going to have a playdate, you should stop by the house and change into something appropriate."

"What?"

"Put on a nice dress and your highest heels. You want to make a good impression."

"I'm just going to pick up the dress."

"Oh, Baby. Don't be like that. Put on a dress, make yourself look pretty, and have a good time."

I shook my head, "Seriously?"

She smiled reassuringly and added, "Promise me you'll have fun at Darlene's, alright?" It was like she was encouraging me to ride a rollercoaster that was just a little bit too scary. "And promise that you'll run this little errand en femme."

I nodded as I tried to compile the implications of what was going on. Was I losing my wife, were we deep in the middle of one of her games, or was something else going on?

***

Darlene's apartment was downtown, a couple of blocks from the river. It was in an old neighborhood where strangers routinely came and went. I checked the address twice to be sure I was in the right place, then parked the minivan across the street. Guys dressed in hoodies and baggy pants congregated around the building's entrance. I wasn't comfortable in the neighborhood, and I didn't know the protocol for getting past the group of guys, so I took a few moments to watch them.

Young men in hoodies fist-bumped and hand-slapped their way past the loitering hoodies, but I wasn't going to be able to get away with that in my dress and heels. I waited several minutes before a woman my age approached the building. She smiled invitingly at the guy reclining on the stairs, laughed at what he said, and then waited for one of the other guys to open the door.

I performed a quick inspection of myself in the van's rearview mirror. The bob wig framed my face perfectly. It set off my cheekbones, which I had contoured to align with the wig's sharp lines. My lipstick was harlot red, and my mascara and eyeliner were perfect. I collected the handbag I'd borrowed from Holly, locked the van, and crossed the street. I'd had just enough practice in my heels to get by, but I was a long way from appearing elegant.

"Ho, ho, ho, what did Santa bring us today?" joked one of the betas that orbited the reclining alpha.

"There's a fine hoe coming my way." rhymed another beta.

I smiled seductively at the reclining alpha and said, "What does a girl have to do to get past you handsome gentlemen?"

He was muscular, relaxed, and comfortable in his domain. He might have been my age, which was quite a bit older than I expected. He looked up at me with a confidence that was unexpectedly sexy and said, "That depends. What do you want to do?" He reached down and tugged at his crotch while he talked. My eyes followed his hand, watching as he adjusted himself. He smiled a cocky smile and said, "I think the fancy lady likes what she sees."

I imagined him pulling my hair and forcing me down. I'd be helpless as he pushed up my dress and pulled down my panties. Without thinking, I'd spread my legs and all but beg him to fuck me, but that wouldn't matter because he'd force himself on me anyway. My ass would burn as his large cock forced its way in, and then I'd start to moan and plead for him to cum inside of me. Of course, it wouldn't play out that way in reality. Once he found out I had a cock, it wouldn't matter how hot I looked, how badly I wanted to fuck him, or how well I gave head. He'd beat the shit out of me and leave me in a gutter somewhere.

Briskly, I said, "Of course I like what I see, but that isn't why I'm here."

The alpha male looked up from his recline and asked, "Who are you here to see?"

I pulled a piece of paper from my purse and read the address, concluding with, "It's about a dress."

"Is it as nice as the one you're wearing?"

I smiled seductively and said, "It's supposed to be a lot sexier."

The posse on the steps broke into howls and catcalls.

The alpha male said, "I'll have my boys let you in if you promise to model it for us on the way out."

I smiled as seductively as I could and said, "That sounds fair to me."

***

Darlene's husband answered the door by opening a door-chain-constrained slit. He peered through it and asked, "What do you want?"

"I'm Nicki. I'm here to see Darlene."

"You're Nicki?"

"Yes, that's what I said."

"No. You can't be."

"Don't be silly. I'm here for a dress."

"If you're Nicki, then show me your cage."

"What?"

"You don't look like Nicki. Show me your cage or fuck off."

I looked left and right to make sure the dimly-lit hall was empty and then lifted my dress and pulled my panties to the side.

Darlene's husband took a long look at my caged cock, closed the door to release the chain, and let me in. She said, "I'm sorry about that, but you look hotter than the typical sissy in a cage."

I smiled and said, "Thanks. You're hotter than I expected too."

She smiled at the compliment. Her complexion was fair, and her hair long and red. Her lipstick and eyeshadow matched the sprinkling of freckles that crossed her nose. She was wearing a long black nightgown that was tented by her modest erection. She told me that Darlene would be available in a few minutes and then lead me into the living room.

The room was furnished in dark woods and polished steampunk steel. Antique industrial lamps illuminated the sturdy coffee table covered in vinyl padding with shiny metal fittings around the side. Heavy-duty hooks were attached to a beam in the ceiling, and leather straps were suspended from similar hooks on the wall. Incense covered the odor of stale sex, and masculine grunts and feminine moans emanated from the bedroom.

Darlene's husband glanced at a clock on the wall and explained, "My Queen is in there with her bull. He usually leaves around 1:00, so you're going to have to wait a few minutes." There was a surrender in her demeanor that I understood all too well. The woman she loved was fucking another man in the next room, and there was nothing she could do about it. Even more humiliating was her shame-induced arousal, which she had no way of hiding.

I'm sure she would have liked to explain it all away. Her wife really doesn't care for the bull anymore. He hardly ever makes her cum. She just does it to embarrass her. But there was no point. We all knew what was happening. The bull was there because Darlene needed him, and I was there to witness her husband's inadequacy.

I wanted to console Darlene's husband by holding her close. I'd stroke her hair and tell her that everything was going to be alright. For an instant, I imagined her suckling from my fictitious female bosom. Without thinking, I did the next best thing; I reached out and clutched her stiff penis through the fabric of her nightie and gently stroked it. I asked, "Does the humiliation get you excited?"

She nodded without looking me in the eyes.

"It's okay. I know exactly how you feel."

Her cock was warm in my hand, throbbing with each beat of her heart. Her eyes closed, and her head tipped back. "Please don't."

I might have stopped if not for the conversation I'd had with Holly that morning. I knew that consoling this poor half-man was the right thing to do, and I wasn't going to worry about what might go wrong. I drew her body into my grasp as I continued to slowly stroke her stiff, little penis. I kissed her neck and nibbled her earlobe, and then I whispered into her ear, "Doesn't it feel good?"

"Mmmmm," she moaned before softly saying, "My Queen will be furious if I cum," but she did nothing to stop my long, slow strokes. She tipped her head back and brushed her crimson hair aside so that I might caress more of her neck with my lips.

My cock strained against the confines of its cage, aching in the most erotic way imaginable as I continued to stroke Darlene's husband's stiff little cock. My cock lifted the cage's weight, stretched my black panties, and pushed up my dress. I desperately wanted to fuck the man-woman in my arms, despite my mechanical castration, her protests, and the presence of her queen only a few yards away. My hips slowly undulated as I mindlessly rubbed the cage against her thigh, pushing myself to the precipice of orgasm with no hope of satisfaction.

Muffled moans and grunts came from the bedroom. Darlene said, "Oh, Baby, you have the nicest cock. I love how it fills me."

The words were undoubtedly spoken for her husband's benefit. Still, I imagined them being said by the woman in my arms while she was laid out on the coffee table with her legs spread wide and my cock buried deep in her ass. My fingernails would dig into her flesh as I bore my stiff shaft into her dank, dark hole again and again.

"Oh, Baby, your cock is AMAZING," Darlene enthused again.

Her husband shuddered in my arms and said, "She says that every time."

I tried to take her mind off of her wife by stroking her cock a little faster. Her eyes closed, and she tipped her head back with her plush red lips slightly parted. My lips met hers. We softly kissed, and then kissed again, and then again.

Between kisses, she said, "Please don't make me cum. She'll kill me if I cum."

I pressed my off-hand against her ass and whispered into her ear, "Well then, you'd better not cum."

Our hot breath mingled as her tongue silently licked my lips, and then she softly said, "Please."

The pace of the grunts and groans in the bedroom increased. Darlene shouted, "Fuck me, Baby. Fuck me." One of them would be coming any minute.

I pressed the fabric of her sheer nightie against her boi pussy with my finger as I stroked her small, stiff penis with my other hand. I said, "I didn't expect you to be so hot," then I forced my tongue into her mouth as I kissed her again.

Her mouth opened to yield to my penetration. As we kissed, she lifted up my dress and began to fondle my balls. She kissed me and said, "I wish I had your key."

I sucked her tongue hard into mine and then said, "I wish I had your stiff little prick in my mouth."

Her breath caught, then she said, "Please don't say that." After a brief pause, she continued, "Not unless you really mean it."

Her body shuddered as I squeezed her penis. "Oh, I mean it. I'm going to take your cock in my mouth while I push my finger deep into your boi-pussy. I'll take you in front of your queen, and I'll make you cum for me while you plead for me to stop." I slipped my hand between her panties and her ass and pressed my finger against her boi-cunt.

The bed in the bedroom banged against the wall as Darlene's bull drove himself home. He moaned loudly and said, "Baby, you are such a good fuck. Why don't you ditch that sissy and come live with me?"

Darlene's husband tipped her head back while she relaxed her sphincter to let my finger push its way inside her body. She moaned softly as she said, "Oh fuck, that feels so good," as her ass accepted my intrusion.

I nipped at her ear as I stroked her cock with one hand and probed her ass with the other. My lips brushed her ear as I whispered, "I'm going to make you cum. I'm going to do it right here, right now."

"Oh, God. No! She'll kill me if I cum without her permission."

My strokes became more energetic. "You'd better hold yourself back, then."

Her body tensed as the strokes became faster and shorter. But before I could get her off, the bull emerged from the bedroom, wearing only a t-shirt and socks. His dick was at half-mast and covered in spunk. He said, "Hey faggot, knock it off. It's time for you to take care of me."

Darlene's husband shuddered and pulled herself from my embrace. She looked at me for a second and then turned her attention to her queen's bull. She dropped to her knees in front of him and wrapped her mouth around his softening penis.

The bull put his hands on her head and thrust his cock into her ready mouth. He said, "That's it bitch. You know who your daddy is," as he sneered contemptibly at me.

Darlene's husband's head bobbed up and down on the bull's shaft, which appeared to stiffen a little bit with each bob. She took a breath, then licked the sex residue that mingled with the pubic hair at the base of the bull's cock.

The bull looked at me. "I bet you want to suck my dick too, don't you faggot?"

Without saying anything, I knelt down next to Darlene's sissy husband. She smiled at me and held out her master's saliva-covered cock for me to worship. She said, "Master has a great cock, doesn't he?"

I kissed the head of his uncut masculinity and said, "It's beautiful." I took its base securely with one hand and began to suck his cock. His two hands pressed at my scalp, encouraging me on. After a couple of shallow gulps, I obliged him, swallowing him whole. My face pressed into his pubic hair. I pulled back to measure his satisfaction, then swallowed him deeply again. I wrapped my free hand around Darlene's husband's sissy penis, which was still hard. I squeezed it tightly and stroked it in time with my movement on the bull's cock.

She responded by dipping her head to bite my shoulder as her hand lifted my dress and slipped under my panties. Her middle finger descended the crack of my ass and then bored its way into my asshole.

The bull extracted his cock from my mouth and slapped it against Darlene's husband's red lips. She kissed the shaft on the side then took it deep into her mouth, looking up into the bull's eyes as she did.

12


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