In For a Penny… Ch. 02

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To the reader: Thank you for all the positive feedback and encouragement to write Part Two. I apologize for taking so long. However, I didn’t want to submit a story that contained any clichés, so I had to take my time to think through how this next installment was going to play out. Let me know how I did.

This chapter picks up immediately after Part One. If you haven’t read that, please do so. Part Two will make a lot more sense if you do, although I think I included enough from the previous installment to get everyone up to speed.

NOTE: Every word of this story is true (except for “Every word of this story is true.”)


I found myself in our upstairs bathroom looking at myself in the mirror.

“The hell was I thinking?” I asked myself, not for the first – or probably the last – time this crazy evening.

“More importantly, what was I going to do now?”

I was wearing black thigh-high lace-top stockings, black leather thigh-high Pleaser boots with 5-inch spiked heels, impossibly large silver hoop earrings, Revlon Love That Red lipstick (
25, if you’d like to know), nail polish meticulously matched to my lips, a sexy black lace D-cup bra, and a black leather miniskirt that hugged my ass like a second skin (thank you, Forever 21).

My eyes were painted with heavy black liquid eyeliner (Taylor Momsen eat your heart out!), and I wore a black chiffon-like top with longish sides that could be tied in the front. (I had them tied thus so that my tits jutted out.)

My blond hair was brushed out straight and swept over my right shoulder, partially obscuring my eye in what I hoped was a kind of Veronica Lake peek-a-boo look. The contrast between my very blond hair, the black clothing, black eye makeup, and my red lips and nails was, if I do say so myself, striking.

My only other accessory was a black choker with rhinestones on it that spelled out “SEXY.” Although “SEXY” may be too kind. The word that best described this ensemble is slutty.

Oh, and I’m a guy.

Name’s Jim.

Downstairs sat my wife and her – as I discovered – well-endowed co-worker Cindy. The last I saw them they were sharing a cigarette and daring me to make the next move. So I did.

I told them I had to freshen my lipstick and I ran upstairs, my tits bouncing with each teetering step.

I did so probably as much to buy time to allow my skirt-tenting dick return to its normal position (slightly to the right, if you must know) as to reapply my lipstick. I found myself doing both, applying the bold red Revlon color as well as thinking as swiftly as I could what my next move was going to be.

You see, I’m a big fan of Lit. So is my wife. A few years ago, while I was browsing the stories, looking for something suitable to share with her, I stumbled across a very steamy 6-part series titled Birthday Present written by an author named donnaallure. The excellent stories were about a wife who gives her husband what she thinks will be the ultimate surprise on his birthday – a femme makeover. The objective? To turn them both on and give her a lesbian lover who’s actually her husband. The stories were very well written, and included a bit of BDSM to spice them up. (As if they needed any more spicing after that premise.)

Over the past few years, our sex life has dwindled a bit. Okay. A lot. Granted, we’ve been married nearly 12 years. And we’re incredibly busy with our careers and so, as a result, tired a lot. So, the hot, kinky, and raw sex from the early days of our marriage has been absent. And we both miss it. For some reason, I thought the erotic Birthday Present stories might do the trick and add back some of our earlier vigor.

I’d never thought of crossdressing. Or, if I did, the idea held no appeal for me. I wasn’t gay. Nor was I bi. Nor a cuckold. Nor a sissy. I don’t begrudge others if they embrace those orientations or lifestyles. But none were for me. So what would be the point of crossdressing?

And yet, there I was, dolled up like a tart.

I had planned a steamy, albeit kinky, evening with my wife, Samantha (Sam, for short). But I hadn’t planned on her arriving, late I might add, with Cindy, her coworker. That threw my well-laid plans out the window. And flustered the hell out of me, while simultaneously giving the girls something to snicker about.

I carefully applied lipstick and, for an extra nice touch, some lip gloss to make them even more prominent.

“Now what?” I asked. “Now what, now what, now what?”

“How are you coming, Ronnie?” I heard my wife yell from downstairs. She emphasized the word “coming” in an all-too-obvious way.

Ronnie, or Veronica, was the name I made up on the spot when I opened the door and saw not one, but two hotties standing on the step. Why Veronica? I have no idea. Let’s see you come up with a better name under those circumstances.

The hell was I thinking?

I smoothed my nylon-clad legs, gave my tits a little upward push, pulled down the black leather skirt, and…

…remembered the butt plug in my ass.

What manisa escort was I going to do with that?

I gave it a push, too, and made for the bathroom door.

With each tit-jiggling step back toward the stairs, I wondered what I’d find in the living room. Would the two women, who had obviously been very close before this evening (maybe, maybe not), be even more provocative, no doubt for my benefit? Would they even, gulp, have their clothes off?

I felt my dick rise again and I quickly remembered my mantra: Think unsexy thoughts. Think unsexy thoughts.

At the top of the stairs, I heard Cindy’s voice call out to me, “Ronnie? Are you ever coming down to see us?” She, too, placed undue emphasis on the word “coming.” “We have a cigarette ready. You did want to share a smoke with us, didn’t you?”

“She’s taking too long,” said Sam. “I guess we’ll have to start without her.”

Start what? I thought.

“Be right there,” I said in my best femme voice.

I slowly descended the stairs, slowly and sensuously as I could muster.

“Come on, Ronnie,” Cindy said with a stern tone to her voice. “We’re not going to wait all day for you. Are we, Sam?”

“No, we’re not,” she said.

I got to the bottom of the stairs and looked at the two hotties sitting on the couch. Sam’s was leg was draped casually over Cindy’s. I noticed that her own work-safe business-suit blazer was, like Cindy’s, draped over the back of the couch. She wore a black lace cami with no bra underneath, her nipples poking seductively through the thin material. Damn. Did Sam always go to work without a bra? Or had she removed it while I was upstairs?

Then I noticed the pink lipstick prints from Sam’s neck down to the top of her cami. I assume the kisses didn’t stop there. But I didn’t want to imagine where else they went beyond for fear of popping off in my leather skirt.

Think unsexy thoughts. Think unsexy thoughts.

Both women smoked their own cigarettes now, and wore a smug expression, like the proverbial cat who’d just eaten the canary.

Cindy snapped her fingers and pointed to a spot at her feet.

“Come, come, Ronnie,” she said. “Make yourself useful.” She took a drag on her cigarette and blew a thin stream toward the ceiling.

She looked seductive as hell. And, although I’m ashamed to admit it, I took a step toward her.

That may have altered the entire course of the evening except for one thing: she laughed.

Not a genuine laugh, either. Cindy laughed in that fake dominatrix way that always drove me nuts when I watched those Dom/cuck videos. You know what I’m talking about – the throaty, head-back, I’m-going-to-show-you-how-to-serve-a-woman-you-pathetic, limp-dicked…


I stopped.

I wasn’t about to become Cindy’s bitch for the night.

That’s not what Sam’s husband had “paid” me to be.

“What’s the matter, Ronnie?” Sam asked, for the first time a twinge of doubt flashing across her face. It was only a momentary look. And I doubt Cindy saw it. But it was enough to tell me Sam felt – for just a split second, perhaps – that she’d lost control of the situation.

She had. But I wasn’t about to let on that I’d noticed.

“I forgot something,” I said. “I’ll be right back.”

I spun on my spike-heeled boots and headed back toward the stairs.

“Ronnie!” Cindy said sternly. “You come back here this instant!”

“Just take me a second,” I said as I bounced back up the stairs from whence I had just descended.

I chuckled to myself.

This was going to be fun.

Think sexy thoughts. Think sexy thoughts.

The game had changed.

When I got to the top of the stairs, I strode purposely toward our bedroom, entered, and walked up to the nightstand beside our bed.

I opened our toy draw and pulled out a red ball gag, a pair of handcuffs, and leather ankle restraints.

I smiled.

“Ronnie!” Cindy said from the living room. “I’m waiting!”

Yeah, I thought. You are. But you’ll keep on waiting, too.

I laid out the toys on our bed and looked into our mirror.

This outfit wouldn’t do. Not for what I had in mind now.

Oh, the boots and skirt were okay. But the top was all wrong. Too tame. Too dressy.

I dug under the bed and pulled out a leather dress (thank you Charlotte Russe). I took off the black lacy top and wiggled my way into the leather dress, not bothering to unzip it first. It was so tight that it clung to every curve like Saran Wrap around a pork loin.

Because the dress was made for a woman, it didn’t cover enough to actually be a dress on me. It was more like a large leather top. So I tucked the bottom of it into my leather skirt and turned to face myself in the mirror.


Not only did it feel amazing to be encased in leather from neck to, well, toe if I count the boots, I looked like a Dom hooker about to give a sub a swat on the keister.

Which was not that far off, frankly.

In my mavişehir escort mind’s eye, I pictured the legendary Taylor St. Claire in her heyday, wearing a skin-tight black leather dresses and thigh-high boots in one of those fetish videos she used to make before she chunked up a bit (age will do that to a person, I guess).

Don’t get me wrong. I hadn’t a snowball’s chance of looking like Taylor, especially since she is a brunette, and I’m a blond. But more to the point: she was a hot babe and I’m a guy on a mission to rock his wife’s world. I knew that. But I had to psych myself up somehow. Why not imagine I’m Taylor?

“Ronnie!” I heard someone downstairs say. “If you don’t get down here this minute…”

She let the thought trail off, probably because she (whoever it was) didn’t exactly know what the punishment would be if I didn’t hustle downstairs.

I didn’t answer.

Instead, I rummaged around in our toy drawer until I found a pack of Parliament Light 100s my wife kept there for when she was feeling frisky (I have a thing for all-white cigarettes). I lit one and sat on the edge of our bed, leisurely smoking and occasionally looking at myself in the mirror.

I flicked my ashes in the ashtray on the nightstand, and reveled in the fact that the two of them were probably wondering what I was doing – likely, in their minds, chickening out. Ha! Let ’em wait.

Finally, I picked up the handful of toys in my right hand, kept the cigarette in my left…and turned back to the stairs.

This time, I walked with more confidence because, this time, I was the one in control. “The hell was I thinking?” my ass. I knew exactly what I was thinking.

I descended the stairs, stopped about ¾ down and took a drag in my best Taylor St. Claire fashion and made sure my handful of toys was visible to them.

Now Sam looked really worried. I grinned inwardly.

“What do you have in your hand, Ronnie?” Cindy said. “Are you in the mood to let us play with you?”

“No,” I said.

Cindy pouted.

“I’m in the mood to play with you,” I said, “whether you let me or not.”

I wish you could see the look on their faces. Even Cindy, faux-Dom Cindy, looked somewhat taken aback.

I walked to the couch and wiggled my ass until they moved apart. Then I sat down with a plop between them.

“Where were we?” I said. “Oh, yes. We were going to share cigarettes. Here, Cindy. Try my Parliament.”

I extended it to her, filter first, a red lipstick mark visible on it. She paused for a moment, wondering what my game was, and leaned in for a drag.

She blew a stream toward the ceiling.

“No, that won’t do,” I said. “Blow it into my mouth.”

To my surprise, Cindy leaned over, took another drag, and then her lips met mine. She exhaled. I inhaled, and then blew out the smoke.

I didn’t even care that my dick was rising faster than a pole barn in an Amish community.

“Your turn, Sam,” I said as I held out my cigarette, filter first, toward Sam. To my surprised (and skirt-tenting pleasure) she didn’t hesitate. She leaned in and took a drag.

Instead of exhaling, she leaned closer until her lips met mine. She exhaled. I inhaled.

Ahh, the joys of sharing smoke with two hotties. Well, three, if you count me – which, by that time, I did.

I looked at both of them, paying special attention to the lipstick marks on my wife’s chest.

“What were you naughty girls doing while I was upstairs?” I asked. “Whatever it was, don’t let me stop you now that I’m here.”

I stood up and turned to face them.

“Please continue,” I said. “You don’t mind if I watch, do you?”

I saw them shoot a glance at each other. Clearly, they had been playing me all along, seeing if they could titillate me, push my buttons. I had called their bluff, and turned the tables at the same time.

“Come, come,” I said, emphasizing the word “come” just as they had done. “I don’t have all day.”

I paused, waiting. They didn’t make a move. This time it was Sam who’s eyes were pleading with me. I didn’t give any hint as to what my plan was.

I slowly walked over to the chair I had sat in before bolting upstairs to freshen my lipstick. I laid down my handful of toys on the seat.

“Why don’t you start by sharing a cigarette,” I said. I walked back over and I reached for Sam’s pack on the table beside her, took one out.

“First,” I said. “I think you two need to freshen your lipstick.” Pause. “How about pink? It looked so good on Sam before. And it apparently made such a nice trail of prints down to her cami.”

I glanced at Cindy. “Hon, why don’t you put some lipstick on Sam?” I asked, sweetly.

Cindy reached for her purse and withdrew her tube of lipstick, pulled off the top, and twisted the bottom until the cylinder of pink emerged again. She leaned toward Sam, who – bless her heart – leaned over to her, pouting her lips. Cindy applied a nice layer of lipstick and sat back to admire her work.

“Not menderes escort bad,” I said. “Now, Sam, why don’t you put some on Cindy?”

Sam reached for Cindy’s tube.

“No,” I said. “Not like that. Like Cindy did before. Share what’s on your lips.”

Sam glanced at me, wondering how far I was going to take this. But she did it, leaning over to Cindy and planting a healthy kiss on her lips…and kept them there, smearing the lipstick evenly until they both wore the same shade, albeit a slightly lighter shade because of it. They eventually broke their lip lock and looked at me for approval.

“Yes,” I said. “Very good.”

I paused for dramatic effect.

“Now, please continue. I’d like to see pink lipstick marks on Cindy’s neck and chest. You can do that, can’t you, Sam?”

I lit the Marlboro Light 100, exhaled a stream, and handed the cigarette to Sam., who took it and took a drag.

“Maybe you two could share a smoke while I go freshen up our drinks,” I said and grabbed all three glasses, which by now were empty, and strode into the kitchen, my boots once again click-clacking on the tile floor.

This time, I didn’t hear any giggles and whispers, although I may have heard a moan or two. Maybe.

I filled the glasses and walked them carefully back into the living room. I didn’t spill a drop, which pleased me. I was getting pretty good at walking in thigh-high boots.

The two of them had been busy. Now it was Cindy who had lipstick kisses down the front of her chest.

Cindy took a drag from her cigarette and leaned over to Sam, exhaling into her mouth while Sam inhaled.

Sam blew out the smoke and looked at me with a “what next” expression, obviously proud of herself for following my directions.

Perfect. Time to take this to the next level.

“Not bad,” I said. “But I think you can do better. You both seem to have ample breasts.” I glanced purposefully at their chests as I said it. “Why don’t you put a nice lipstick kiss on them?”


“Sam,” I said. “Get Cindy’s tube of lipstick, freshen your lips, and give Cindy’s breast a kiss. Come on, darling. Don’t keep me waiting.”

Sam glanced at Cindy with raised eyebrows. If I could get them to do this, I could put my plan into action.

Cindy handed Sam her tube of lipstick. Sam took it and handed her cigarette to Cindy.

Sam applied the lipstick, heavily, while Cindy took a long, slow drag. Then Sam reached over and pulled down Cindy’s top to reveal a really shapely breast that momentarily took my breath away. Outwardly, I remained cool – unless you count my growing erection. That would have given me away had the two not been so intent on what they were doing.

I grinned and picked up my toys. I sat down in the chair with my glass of wine and sipped, watching. Waiting. My leather dress was smooshing the breast forms into my skin in a way that made them feel part of me. I liked it.

Sam leaned over and took Cindy’s right breast into her mouth and sucked. When she pulled away with a pop a neat little ring of pink lipstick was left behind, encircling Cindy’s areola.

Cindy looked down and moaned. She was getting turned on.

“How about the other one, Sam?” I asked. “You don’t want to leave Cindy looking lopsided, do you?”

Sam grinned and re-applied Cindy’s lipstick. When it had covered her lips with a thick coat, she reached over and pulled Cindy’s other breast out of her top. She wasted no time attaching herself to Cindy’s left breast. This time, her tongue swirled around the nipple, causing Cindy to moan even more loudly. Another hard suck and – pop! – Sam pulled away leaving behind a matching ring of pink.

Cindy leaned back and took another drag of her cigarette before passing it to Sam. Sam took a drag and blew out the smoke – directly toward me. It was like she was throwing down the gauntlet.

Well, okay, then. I wasn’t about to let that go unchallenged.

I held out my toys.

“Sam,” I said. “Please put this ball gag in Cindy’s mouth.”

Cindy’s eyes went wide. Sam hesitated, but just for a second. She reached for the ball gag.

“Come here, Cindy,” she said. “Face the kitchen.”

Cindy sat up straight and stubbed out her cigarette. She turned her back to Sam and reached for her top with the intent of pulling it back up.

“No, no,” I said. “Leave it down. The pink lipstick looks good on you.”

Cindy lowered her hands. Sam brushed Cindy’s hair aside and put the ball gag into Cindy’s mouth, buckling it tightly behind her neck. She smoothed Cindy’s hair back in place over the strap.

“Perfect,” I said. “Now the handcuffs.”

I held out the silver cuffs. Sam took them.

Cindy placed her hands behind her back and Sam snapped the cuffs on. Cindy shuddered and began to breathe more heavily.

She looked spectacular with her tits jutting out, a red ball gag in her mouth, and her hands cuffed tightly behind her back. I reached down to my tenting skirt and moved my cock to the side so my lust couldn’t be seen as readily. Sam noticed, though, and grinned.

“One more item,” I said, and held out the ankle cuffs.

Sam took the ankle cuffs and, with the practice that only comes form using them – often – she slipped them around Cindy’s ankles, just above her high heels, and buckled them in place.

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