Tango on the Razor's Edge Ch. 03

Chapter 3/27: A Sissy Cuckold Shopping Spree

The story so far:

Nick expected Holly to beg for forgiveness after discovering her affair. Instead, she coerced him into admitting he was a crossdresser. The next morning she fed him a fresh cream-pie from her pussy then asked him to try living as her cuckold for the next couple of months. When he reluctantly agreed, she rushed him out the door to begin their new adventure.

***

Usually, I would have driven, but Holly insisted that she was in control now that I was the sissy. She asked, "Have you crossdressed before, or has this just been a fantasy?"

"I have, but not very often."

"Do you have a secret stash of women's clothes?"

"I used to, but hiding it was awkward."

"Did you ever wear that black babydoll of mine?"

I looked at her sheepishly.

"Come on, my little sissy. We're in it this far. Take the plunge and open up."

I took a breath. "Yes, my Goddess, that was a good one."

She smiled, "That explains a lot."

"I'm sorry I stretched it out."

"We'll get you your own babydoll, but this time we'll get one that fits. You can wear it anytime you want." She rubbed my cock through my pants and said, "You'd like that, wouldn't you?"

"Yes, My Goddess."

"Isn't it liberating to be able to share your secret with me?"

I nodded silently while I tried to imagine what was coming next.

She dropped into thought as she casually toyed with my cock while driving down the highway. "I've learned so much about you that no one else knows. I know you like to crossdress, you like to be cuckolded, and you'd eat another man's come." She paused for a moment, tapped her chin, and said, "Let's see. What else do I know?" After a brief pause, she continued, "You like gay blowjobs; I bet you even dream of sucking cock, don't you?"

There was no point in denying it, so I tried to minimize it. "Maybe someday I'll suck a cock."

Holly squeezed my stiffening cock, smiled, and said, "Maybe someday soon."

***

We went into one of those department stores that was being killed by online shopping. A few people milled about, but it was far from crowded. At the high-end makeup stalls, young girls applied rejuvenating creams to the faces of middle-aged women desperately clinging to their waning youth. The lingerie section was staffed by a full-figured woman who did an outstanding job looking sexy without overstuffing her clothes. She asked, "May I help you?"

Holly responded matter of factly. "Yes, my husband would like to buy something feminine and sexy in his size. Is that something you can help us with, or would you recommend we shopped at one of the fetish boutiques downtown?"

The saleswoman smiled broadly. "Oh, I will be more than happy to help you with that." Her enthusiasm took me off guard. She introduced herself as Darlene as she shook Holly's hand. Then she led us back to an alcove that was surrounded by changing room doors. Holly took a seat on a sofa and watched as Darlene sized me up. She said, "Let's have a look at your princess," as she stood back to take me in. She wrapped a measuring tape around my waist and fetched a pair of panties. She directed me to one of the changing rooms and said: "Go put these on and come right back."

The skimpy panties barely concealed my semi-aroused penis, which I hid behind my hands.

Darlene lifted my hands and said, "Sweetie, the first thing you have to learn is that girls flaunt what they've got. You've got a nice body, so stand tall, push your chest out, your shoulders back and be proud."

I did my best to imitate a pose I might have seen in Vogue. Darlene said, "That's it," while Holly softly applauded.

Darlene carefully inspected my body. "Let me see, we need to minimize your shoulders and direct the eye to your legs. You have great legs, but you are going to need to shave them."

Holly added, "He'll need to shave everything."

Darlene smiled, nodded, and said, "Yes, everything." She took a few measurements, asked my shoe size, then went off to select some items for me to try on.

While Darlene was away, Holly's phone chimed and then chimed again. She typed out a text and then snapped a picture of me.

"Is that Dan?"

"Yes. He thinks you look cute in panties. Spin around. I want to send him a video."

I turned in front of the camera once, but Holly wasn't happy with my performance. Before I could do it again, Darlene returned with an arm full of frilly items. She laid out an assortment of different styles and then explained the differences between them. She picked up a basque and held it up to my chest and said, "This will break the line of your shoulders and make you look more feminine."

"Do you like that?" Holly asked.

"Can I try it on?"

"Of course," said Darlene. "But first put on these." She handed me a shoebox that contained a pair of black heels. "These will accentuate your legs."

I slipped on the heels, then pulled on the silky basque. Its tight fit made it feel super sensuous against my chest. My nipples hardened, and my penis began to stretch the lacy panties.

Darlene said, "I think she likes it," as she adjusted my panties to cover my hardon. She straightened the basque at the waist and then slid her hands across the silk fabric, concealing my chest's muscles. In a sultry voice, she asked, "It feels sexy, doesn't it?" Without waiting for a response, her hand flowed over my back down to my ass, where it came to rest on the lace drawn tight across my butt. Her finger pushed in, stretching the fabric between my butt cheeks until her fingertip pressed against my asshole. While her finger danced on the rim of my anus, she squeezed her large tits against me, exposing her deep cleavage.

I covertly admired her large breasts that were drawn tightly together by her low-cut bra. Despite her large frame, Darlene was an unusually sexy woman. She walked and talked with a self-assured ease that commanded respect and expected desire. Her lipstick was deep red, her eyes were darkly shadowed, and her perfume was dense with wildflowers. Her dark skin was smooth and inviting.

She rubbed her tits against my body while her finger circled around my puckered ass. I would have dropped to my knees to please her if she had simply spread her legs; instead, she asked in a smoky voice, "Doesn't it make you want to bend over and let someone take your tight little boy pussy?"

Holly chimed in, "Oh, she likes it when people take her ass. Don't you, Sweetie?"

I sheepishly smiled while I shook my head in embarrassed disgust.

Darlene smiled. "Oh, don't be like that. I've got a little girl at home just like you. She likes to get down on her knees and show me how good she can be."

"Do you let her play with your lovers?" Holly asked.

"Sometimes, if she's been especially good, but usually I let her play with her sissy girlfriend. They make a cute couple all dressed up. With frilly underwear poked up by their stiff little penises."

Holly laughed, "Is that what you want Nicki, a cute little sissy girlfriend to play with?"

Darlene stroked my raging hardon then said, "You'd like that, wouldn't you?" She turned to Holly and said, "We definitely should arrange a playdate."

Holly replied, "Is that what you want, Nicki, a playdate with Darlene's sissy husband?"

Nicki? Where did that come from? This game was getting out of hand. I'd fantasized about crossdressing, not becoming a toy doll. I had no interest in a playdate with Darlene's husband. But any protest I might have made would have been undermined by my state of arousal, so I smiled as I looked through the lingerie.

Darlene said, "We really should get our girls together. They would have so much fun," as she took a seat next to Holly on the sofa. I continued looking through the items while I eavesdropped on their conversation. Darlene asked, "Do you have a boyfriend yet, dear? You simply must have a real man to take care of your needs when you're married to a sissy."

Holly smiled and said, "Oh, yes. I do."

"Have you introduced him to your husband?"

"Yes, they're well acquainted."

"Have you had your husband formally submit to him?"

"What do you mean?"

"There can be only one alpha male in your life, Dear. You have to make sure your sissy knows who's boss by making her formally submit to your lover. I had my husband give my lover a blowjob; after that, everyone knew the pecking order. We repeat the ritual every few days, just to be sure she remembers her place. At first, she resisted, but now she accepts her new role in my life."

"How long did it take for her to accept it?"

"It wasn't that long. I think she was just pretending not to like it." Darlene laughed, then said, "You know how sissies are when they're around a hard cock." The two women giggled like they knew I was listening.

I thought of kneeling in front of Dan in the conference room wearing the basque, a pair of panties, and silk stockings suspended from a garter belt. Holly would watch as I unzipped his fly and extracted his cock. She'd say something encouraging while she pushed at my head. She'd use some crazy pretzel logic to explain that this was something I needed to do to make our marriage stronger. It was insane to think that sucking her boyfriend's cock would strengthen our marriage, but it made my cock frighteningly hard nevertheless. What the fuck had I gotten myself into?

Darlene said, "The best part of having a sissy husband is having her submit to you. Once she knows that nothing matters but your happiness, your life will be better than ever. You'll wonder why you hadn't done it years ago."

Holly nodded in thoughtful agreement for a moment, then asked, "Are you sure she's ready?"

Darlene replied, "Of course she is, just look at her."

I looked up to see the two women looking at me. They both smiled with the calm confidence of a predator whose prey was cornered, out of options, and with nowhere to run. In their minds, my fate was sealed.

Rather than listen to any more of their insanity, I picked up things I liked and said, "This should do it. I'll go get dressed so we can get out of here."

Darlene replied, "There's no rush. You take your time and make sure everything fits."

Holly checked the time and said, "She's right. We've got a couple of more stops before we have to pick up the girls."

"Well, call if you want to arrange a playdate. I'm sure your little sissy will enjoy it."

Holly smiled and said, "Of course! It will give us time to talk more about establishing the pecking order."

Darlene directed me to one of the cashiers, where I paid while the two women chatted. I followed Holly to the car. From the passenger seat, I asked, "What else do we have to get?"

Holly smiled and rubbed my leg. "You don't want me to spoil the surprise, do you?"

"That depends. Are they setups like Darlene was?"

"What do you mean?"

"Darlene was expecting us. She didn't have a name tag, and she handed the sale off to the clerk, who pocketed the commission. So, it's a pretty safe bet that she doesn't work at that store, which means you arranged for her to meet us there. Besides, what are the odds that the first saleswoman we encounter is married to a crossdresser? It was a setup."

Holly laughed. "Aren't you the clever little girl? Does it bother you that I wanted to make our day out fun?" She stroked my cock and said, "Judging by your hard little pee-pee, I'd say you enjoyed yourself."

Hard little pee-pee? What the fuck? I shook my head and said, "It would be a lot more fun if the stakes weren't so high. You're fucking my boss and humiliating the shit out of me. I'm trying to play along, but it's pretty fucking difficult for me to enjoy myself with my marriage on the line."

"Okay, that's fair, but let me ask you something, where is the line? Is my affair too much? Is sending pictures of you in panties to Dan too much? Or is it watching us have sex or forcing you to suck his cock? Tell me where the line is because I don't know. It all seems to turn you on. I know it turns me on, and I want to find out how far we can push this."

I thought for a long time before I said, "Wow, I don't know how to answer that."

"I know, right? I want to dance right up to the edge, and I want to do it with you."

"What if you push too far?"

"I don't know, but I'd like to find out."

She pulled the car into the parking lot of a sex shop and set the break. With relaxed confidence, she said, "Let's go strain our relationship a bit more."

She led me by the hand to the corner of the store filled with dildos and strapons. In a voice that was louder than necessary, she said, "Pick the one you want me to use on you." The few men milling about took a second to size us up. I'm sure that they thought of me bent over while Holly thrust her hips to drive the silicone phallus deep into my ass. Most of the guys returned to their shopping, but one guy smiled at me. I think he thought I was lucky.

Some of the strapons had ridiculously large dildos. A few of the dildos had bumps or simulated veins that were presumably there to increase their stimulation. They were clear, caucasian, pink, blue, black, and brown. I picked out one that didn't look too painful: "What about this one?"

"Do you think you can handle that? It seems kind of big for a tight little ass like yours." Once again, her voice was too loud.

"You'll just have to be gentle."

She stroked my head and said, "Of course, I'll be gentle with you."

The same bunch of guys surrounding us simultaneously smiled in amusement.

Holly picked up the big black one and said, "Are you sure you wouldn't rather have me be gentle with this bad boy?"

"I don't think that much gentleness exists."

Holly laughed and put it back against the wall. "We'll save that one for later."

She picked up the smallest of all the dildos, which must have been meant to be a clitoral stimulator. After inspecting it for a moment, she said, "This one's about your size." Once again, she said it much too loud.

Once again, every guy in the store looked to see what she was talking about. Two of the guys laughed out loud. A third said, "It looks like they both need more meat," to the laughter of the other customers.

A big guy with a couple of magazines in his hand approached Holly and said, "Hey beautiful, I've got what you need."

Holly smiled at him. "I'm sure you do. Do you want to show me now, or are you going to keep me in suspense?"

"Come back to my place, and I'll show you. I'm sure your little man wouldn't mind." He turned to me and said, "You don't mind, do you, pussy?"

I was too humiliated to respond, but Holly's smile broadened. "That may be okay with my husband, but I don't think my bull would like it."

"You already have a boyfriend?"

Holly's smile broadened even further. "I've already got a bull, but we're open-minded, and there's still room in my stable. I'm sure my husband wouldn't mind if I let you clean me and my bull every once in a while."

The big guy looked from Holly to me in horror. The guys surrounding us let out catcalls, and a guy with a lousy haircut made the siren sound followed by a kaboom of a cartoonish World War II airplane crashing and burning. The big guy scanned side to side for support from one of the other guys. When none was forthcoming, he was left standing in disbelief as Holly led me off to another part of the store.

She held me by the hand as we crossed the store. "The next thing I need you to do is to yield control of your orgasms to me."

"Do we have to do that?"

"It will be good for us. Wait and see."

"Do you have to completely emasculate me?"

"Of course, silly. What'd you think we were going to do, play house?"

The guys from the dildo aisle watched as she led me to the display of male chastity devices. There were about a dozen different choices. Some were plastic, and some were stainless steel. Some came in specific sizes, while others claimed one size fits all. We were trying to sort through them when a young woman asked if we needed assistance.

Holly replied, "I'd like to lock up my husband when I'm out." With a wry smile, she added, "I want to make sure he's in the right frame of mind when I come home if you know what I mean."

The cute young woman said, "Of course you do. Are you out for just a few hours, or are you away for days at a time?"

"Sometimes hours, but I'll be traveling for several days next week."

I noticed the guys from dildos drifting in our direction. One pretended to be interested in books on bondage. Another inspected battery-powered clitoral vibrators that were disguised to look like lipstick tubes.

The salesgirl nodded thoughtfully, then asked, "Is your husband large, medium, or small?"

Holly looked at me and asked, "Do you think you're large, medium, or small?"

I look over Holly's shoulder to catch the small guy with the crappy haircut looking at me. He hastily turned to inspect a display of leather restraints intended for gay men.

I said, "I'm larger than average."

Holly patted my shoulder and said, "Of course you are, Princess." She addressed the salesgirl and continued, "Let's say small and get one that fits."

The salesgirl replied, "I understand." The guy with the bad hair was now smirking to himself while he looked at cock rings.

"You should probably consider one of the flexible plastic cages. The metal cages are good for a couple of hours of tease and denial. But they can get uncomfortable after more than a day if they don't fit exactly right."

Holly played with the sample of a soft plastic cage for a few moments. She shook her head and said, "This doesn't say 'My cock is in a cage' to me. I want something substantial, something that screams, 'I'm locked up.'"

The saleswoman smiled and said, "I know what you mean." She picked up the most expensive cage on display and said, "This is the one I bought for my boyfriend. He's wearing it now." She touched her hand to the chain at her neck and said, "Here's the key."

Holly said, "Oh, that is so sweet. You wear his key around your neck."

"Yeah, it keeps us thinking of one another."

Holly turned to me. "Would you like me to wear your key around my neck?"

I replied with the only acceptable answer: "I would be honored."

Holly beamed at me. "You see. This is going to be fun."

A couple of guys looked at me briefly and then quickly returned to browsing. The guy over Holly's shoulder stared at me with an expression that was a mixture of envy and disgust. The guy looking at cock rings was smiling from ear to ear.

The saleswoman retrieved the cage from a locked cabinet. "This cage is a little more expensive than the others." She pointed to the selection of polycarbonate cages. She said, "With the others, the occupant can escape by pushing the pins back or squeezing through the gaps, one spongy bit at a time. This cage doesn't have any slippery pins, and it's much more rigid, so it won't flex to let the balls squeeze through the gaps. With this baby, you can rest assured that you'll be coming home to someone who is thoroughly and completely chaste."

Holly replied, "Oh, I like the sound of that!"

The saleswoman smiled. "I thought you might."

I protested, "Didn't you say the metal cage was intended for play rather than long-term chastity?"

"Well, yes. The plastic cages are a lot more comfortable, but that's the price you pay for true peace of mind."

Holly stroked my arm. "You care about my peace of mind, don't you, Sweetie?"

Holly, the saleswoman, and the half-dozen guys who had been eavesdropping on our conversation all looked at me. I tried to focus on Holly, but I knew I was speaking to a much larger audience. "But, this one looks so painful."

"Well, it's your choice." She inspected the metal cage. "But with you wearing a cage this substantial, I could spend nights with Dan without worrying about you. Think how much happier that would make me."