In For a Penny...

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see.

NOTE: Every word of this is true. (Except for "Every word of this is true.")

*****

I sat on the edge of our four-poster bed and gazed at myself in the mirror.

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 (#725, 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 hugs 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.

The D-cup bra holds a pair of silicone breast forms, which are attached to my chest with medical-grade adhesive.

And I'm waiting for my wife.

Only she doesn't know I'm waiting for her. Not like this, anyway.

Let me back up a minute. I have some 'splainin' to do.

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.

Did I mention the butt plug in my ass? No? Well, there was one.

I looked at myself in the large mirror attached to my wife's dresser.

The hell was I thinking?

I doubt I'll ever pass as a woman. After all, I'm middle aged, slightly overweight (but not terribly so - I'm pretty active) and kind of tall for a gal. In these heels, I stand about 6'4". I weigh around 220.

I glanced beside me on the bed at the 6-inch black strap on and harness, bottle of lube, and four neat piles of coiled rope. Was this really a good idea? What will my wife think? Will she be turned on? Disgusted?

The longer I waited, the more of my nerve I lost.

How did I go from macho man to "lesbian" escort at the age of 45? For that matter, what was it about those Birthday Present Lit stories that, okay I'll admit it, turned me on?

I think it was the fact that my wife is a bi-babe who'd had two lesbian encounters while we were married. She loved it. (So did I, truth be told; I got to participate in one of them.) Our mutual female friend with whom she'd experimented moved away, and my wife has missed that kind of excitement. So I copied the links to the Birthday Present stories and sent them to my wife in an e-mail along with a lot of links to lesbian porn (her fave) from XHamster and stories from Lit.

After that, I didn't hear anything more form her - although from time to time she'd use one of the phrases in the stories in casual conversation. "In for a penny, in for a pound," she'd tell me, off handedly.

One day, while helping her make a backup of her laptop, I found a very steamy Word document titled "For Jim" on her desktop. I opened it...and my jaw dropped open.

In it, she had written (in great detail, mind you) all the delightfully kinky things she wanted to do with me - from movie theater encounters to sleazy hotel sessions complete with me roughly playing with her breasts and tying her up, to - this surprised me - bending me over the bed, tying my hands to the bed posts and fucking me from behind with a strap on...while she stroked my dick wearing latex gloves.

I'm not the smartest tool in the shed. But I put two and two together. Those stories had made a bigger impression on her than I first suspected.

A couple of years passed with no action taken, by either one of us.

After awhile, I began to think about those stories again. Why not do something really out there and crossdress for my wfe, greet her at the door some evening, and tell her - in my best femme voice - that her husband knew how much she wanted another lesbian encounter and that I had been hired for an hour to service her?

So, I decided to play the role of a crossdressing escort. And I decided to play it to the hilt.

In for a penny, in for a pound.

I began to shop around, buying bras and silicone inserts here, a few tubes of lipstick there, and an occasional dress or skirt with a nice top. I got away with it - even when one of those self-checkout scanners balked at a price tag I was trying to scan (it was a lacy black 36 B-cup bra) and a female clerk had to come over and help me.

"Figures it breaks down now," I laughed, thinking quickly and making sure she saw my wedding ring. "My wife sends me in to buy this for her and look what happens."

The clerk chuckled at my predicament. But she didn't suspect I was buying the bra for myself, thank God.

No matter what I bought, though, nothing really got my motor running. It just wasn't enough. Not sexy enough. Not sleazy enough. Not femme enough. (There's only so much Walmart can offer a guy interested in crossdressing for his wife.) One day, I discovered there's a very large store in our state that specializes in a wide variety of items for the crossdresser. So I visited their web site and bought some of them.

Okay, a lot of them. Including humongous D-cup breast forms, thigh-high leather boots (very kinky!), and LaDame women's shoes, which are specially made for men. When all the packages arrived (it took a couple of weeks), I opened them all at once. Jeepers creepers. Just what I had been looking for. Shoes! Any guy can buy dresses or tiny silicone inserts at Walmart. But until a guy buys women's high-heeled pumps - or thigh-high leather boots with a 5-inch spiked heel - well, he just can't call himself a real crossdresser - a statement that made me chuckle. What guy would want to call himself that, anyway?

I put on the boots, practiced walking in them, and then applied the breast forms, slathering them with the special adhesive so they'd stick tight, and stuffed them into the D-cup bra.

It gave me a whole new outlook on life.

Over the summer, I practiced in earnest, trying on this and that, wearing outfits I'd purchased, and even applying different colors of lipstick.

Once, I even put on the bra and D-cup breast forms and went to get a pack of cigarettes at the local convenience store. Granted, I wore a large, baggy jacket that I hoped hid me enough so that no one could tell I was rather busty for a dude. Still, I wanted to try going out to see what it felt like.

It felt good.

So I took it a step further, got dolled up (breast forms, a tight black miniskirt, dangly earrings, and a really nice purple and black top that made my breasts look huge) and I found some lesbian porn.

Let me tell you, beating one's meat while wearing an outfit like that is a thrill I can't even begin to describe. My breasts bounced and swayed and jiggled. Boy, did they jiggle. Now I know what a woman feels like when she is getting fucked. I also discovered why women with larges breasts complain about backaches. My back was sore after spending a day wearing these lifelike silicone forms. (Gals, my sympathies.) For an extra bouncy thrill, I'd stuff the D-cup forms into the B-cup underwire bra, which caused my breasts to spill over the top and jiggle like six pounds of Jello in a three-pound bowl.

I was able to do all this without my wife finding out because she travels a lot for work, and is often gone for days at a time.

One night when I was alone, must have been around twelve o'clock, I decided to walk outside total en femme. So, I put on the entire outfit - black pumps included - and started toward our car. The heels made a horrendous racket on the pavement. The dead of night, instead of providing ample cover to practice my femme skills, amplified every sound of my walking. I chickened out when I got about half-way to the car and turned around...and quickly walked back inside, click-clacking the entire way.

Still...

I was determined to go through with it, which must give you an idea of how badly I wanted to rekindle our sexual spark. I really do love my wife. And I know she loves me. So I was hell-bent on doing whatever it took to rev up her engines, even if it meant totally embarrassing myself.

But, at that point, I still wasn't sure what "it" was. I just knew that I wanted to turn on my wife - and, hopefully, myself while I was at it.

Eventually, I discovered crossdresser porn that gave me outfit and makeup tips. I found a lot of it, mostly on Tumblr sites - not to mention a few threads on Lit. A lot of those crossdressers were hot. And their outfits were, well...let's just say I was jealous they had the bodies to pull them off.

Bolstered by my new-found confidence, not to mention a growing femme verisimilitude, I began to hatch a plan. I even bought the aforementioned butt plug, thinking that would help stretch me out to the point where my wife could, well, live out her fantasy.

Which brings me back to the beginning of my story...and why I found myself sitting, dressed as a cheap hooker, waiting for my wife. Well, maybe not a cheap hooker. More like an expensive - or, at least, reasonably priced - escort.

It was now or never.

I was ready to give my wife a treat a la the Birthday Surprise stories, plant whore-red lipstick kisses on her breasts, lick her delicious pussy, make her come a few times, and then let her have her way with me while she was all steamed up.

That was the plan, anyway. And I had carefully rehearsed it for a week or two, even down to what I'd say and how I'd say it.

Funny how real life has a way of throwing pre-scripted events to the wind.

The night I sat en femme (en ho?) waiting for my wife, she was late getting home; hence, my ebbing nerve. The minutes crawled by. At 5:45 (she's usually home by 5:15), I was ready to pack up all of my stuff and forget the whole thing.

But then I thought of my wife, Samantha (Sam for short), and our waning sex life...and I stayed put, waiting.

Sam is a hottie who stands about 5'6" tall, maybe 130 pounds, has a 100-watt smile, and really nice C-cup breasts that jiggle just so when she walks. And let's not get started on her ass, which is delectable. When she puts on her black leather thigh-high boots, garter belt, black lace panties, teases her hair, applies thick mascara, and pours herself into a corset she looks like a MILF. Okay, a streetwalking MILF. But you get the idea. She looked hot.

At least, that's what I remember. She hasn't worn an outfit like that in years.

So I figured I would.

And I was. Minus the corset, of course. I had on what I thought was a hot, albeit whorish, outfit. Waiting. Waiting. Waiting.

Finally, I heard her car pull in the driveway. I glanced at the alarm clock. It was nearly 6:00.

I lept to my feet.

It was now or never. No way to back out - especially wearing the adhesive-attached breast forms - in the scant moments it would take her to walk from the car to the front door. I had to go through with it.

I gave myself a final once over in the mirror, smoothed the leather skirt over my ass, ran my hands up my stockings, boosted my tits upward, gave the butt plug a little push to keep it tucked inside, and raced to the door as fast as my high-heeled legs would carry me. The plan was to throw open the door, and breathily whisper (in my best feminine, husky voice - which, in my mind, was supposed to sound like Marilyn Monroe singing Happy Birthday to JFK) "Surprise!"

Only I never got that far.

I opened the door and got as far as "Sur-" when I saw not just my wife standing there...but her coworker Cindy as well. I had never met Cindy before. But she fit my wife's description of her perfectly.

"Oh, shit," I said.

The look on my wife's face probably matched mine: abject horror.

The look on Cindy's face was hard to read.

I had to think. And damn fast.

"Trick or treat!" I said with as much bravado as I could muster.

Probably not the smartest thing a guy who resembles a tawdry crossdressing escort could say. But it was the week of Halloween. So I thought I could pull it off.

There was a pause. A long one.

"I can see what the trick is," Cindy said. "But what's the treat?"

I laughed. It probably came out sounding like Don Knotts in the Ghost and Mr. Chicken, or Danny Kaye in White Christmas - you know, high-pitched and nervous. More of a giggle than a laugh.

My wife just glared at me.

Clearly, Cindy - who I've long suspected my wife fancies - is also a hottie. Even Stevie Wonder could see that. She's a blonde, big-breasted woman about the same age as Sam (35), but a little taller. They'd gone out to movies before and an occasional evening with the girls. But, to my knowledge, the two of them never did anything sexual because my wife wasn't sure Cindy fancied her back. Because they only hung out a few times, and - as I mentioned, I had never met her - I had no reason to believe my wife might bring Cindy home with her tonight.

Since I was now stuck with it, I embellished my Halloween cover.

"So, what do you guys think?" said I. "Will this win me first prize at the office Halloween party?"

I regretted it the second I said it. I didn't have an office. I was a consultant who worked from home. My wife knew that, of course. I just hoped Cindy didn't

"Can't tell yet," Cindy said. "Give us a twirl."

My wife still hadn't said a word.

I backed away from the door into our house. I didn't want our neighbors to see me like this. I was embarrassed enough as it is.

As I backed up, Cindy boldly stepped forward, followed by my stone-faced wife who, bless her heart, at least had the courtesy to close the door behind them.

I gave them a twirl.

"Yeah," Cindy said. "Not bad. Not bad at all."

She turned to my wife.

"What do you think, Sam? Will she win first prize?"

Sam found her voice.

"Maybe," she said, slowly. "But it depends on what her name is. That might make or break the look she's going for."

She paused.

"So," Sam said, obviously pushing me, "what's your name...hon?"

Hell. I hadn't thought that far ahead. Not even my "script" for this event included a name for me. I was just going to be the nameless, shameless whore, hired for a romp in the sack with Samantha.

"Uh, Veronica," I said. "But you can call me Ronnie." I extended my hand to shake someone's. Anyone's.

"Ronnie," Cindy said as she took my hand and gave it a light, feminine handshake. "Pleased to meet you." Pause. "So, Ronnie, are you going to invite us to sit down? Or do you expect us to stand here all night?"

My wife did not extend her hand. I glanced down at her shoes, thinking I was later going to get an ass kicking with them. I wanted to see what I was in for. She had on a conservative office-appropriate pants suit and black 3-inch pumps. Maybe black 3-inch pumps wouldn't hurt much, I thought. Maybe.

"Have a seat," said I, not know how far I should take this charade. After all, the Big Event I had anticipated wasn't going to happen now. So what was the point of continuing as Ronnie any longer?

"I think I'll go upstairs and change," I said, turning toward the stairs.

"Hold on, Ronnie," Sam said, emphasizing the name Ronnie. "Could you get us a couple of glasses of chardonnay before you change out of that, uh, adorable little outfit?"

I froze. Now what? I thought.

"Sure," I said. "Just be a minute."

I crossed the living room and disappeared into the kitchen, my thigh-high boots click-clacking across the tile floor. I rummaged around to find two wine glasses. Well, why not make it three? What kind of host would I be if I didn't have a drink with them?

As I popped the cork and poured the wine, I heard whispers and laughter coming from the living room. I couldn't make out what they were saying. But they seemed to be having a good time of it. At my expense, no doubt. My face burned red. The hell had I gotten myself into?

I returned to see Cindy sitting on the couch. My wife sat next to her. I mean, right next to her. Cindy was smoking a cigarette...and watching me intently.

Since I have a bit of a smoking fetish, I could feel my dick starting to rise; however, I was only wearing lace panties under my leather skirt and I was afraid it would quickly become obvious that I was more of a Ron than a Ronnie.

It would look suspicious if I turned around now. So I quickly walked over to them, my tits bouncing with each step. I handed each a glass of wine in turn - starting with my wife. I hoped that would earn me some points...and avoid the impending ass kicking.

As soon as my hands were empty. I spun around and headed toward the kitchen. Why I didn't take that opportunity to dash up the stairs to get out of this ridiculous outfit is beyond me. The hell was I thinking?

"Where are you going, Ronnie?" my wife asked.

"Just getting a glass of wine for myself," I said, willing my dick to behave itself.

Once in the kitchen, I grabbed my glass of wine and took an unladylike gulp. I poured it full again and strolled carefully (heel, toe, heel toe) back into the living room and sat in the chair opposite them. I crossed my booted legs, hoping beyond hope that my growing excitement had gone unnoticed...or, at least, wouldn't be noticed if it happened again. Hmm. Come to think of it, I could have sworn I saw Cindy glance southward when I entered the room the first time...and smile, ever so slightly, like Mona Lisa.

Maybe I imagined it.

What difference would it make if she smiled at me or not? Cindy isn't my wife. And it wasn't like I could quickly shoo Cindy out so I could jump my wife's bones...even if she wanted me to - which, at this point, I was quite sure she did not.

But I couldn't take my eyes of Cindy. She was pulling out all the stops, smoking a Marlboro Light 100 sensuously and slowly, taking long drags, French inhaling, even demonstrating a wicked snap-inhale technique. She took measured sips of her wine and looked at me with an expression I could not read. Bemusement? Pity? Why was she looking at me - well, aside from the fact that I was obviously a guy dressed as a hooker.