Caught Red Handed


With Halloween falling on a Monday, my wife Suzie was busy the weekend before trying to find her costume to wear to work. As a dutiful sissy husband that loves shopping as much as any woman, I tagged along, although our choice of stores to peruse is completely opposite.

Suzie is a Goodwill addict, with anything at a bargain giving her much pleasure. Me, I'd just as soon be at Saks or some other high end woman's boutique.

As she drifted through the clothing isles at Goodwill, she found nothing to suit her fancies in the women's section and other than a few mini-skirts, neither did I.

I held up one short little red mini and sarcastically said, "Perhaps, I'll buy this hot little number and show up to work and give the boys a thrill."

"Go ahead, I'm sure Maurice would love to see you on your knees sucking his big black cock." she teasingly said, with a chuckle.

"Everyone would get a kick out of how well you walk in heels and how good you are with your makeup. Plus, Kim would love to see you in drag, seeing as how she once saw you in Macy's lingerie department, fondling girdles." she went on to tease.

Blushed with embarrassment, I replied. "You wouldn't tell them you did my makeup?"

"Oh sure I would, my little sissy." Suzie smarted back.

I put the mini skirt back, much as I wanted it, I had to think hard and long about the idea of dressing at work. I'd met Suzie there years before we married as I contracted at her company from time to time. Her office was filled with women; a couple that were drop dead gorgeous, especially Kim the receptionist.

Every morning I drooled over her as I passed through her area to go to work. She was always dressed to the nines, a natural blonde with green eyes that would melt any man, including me even though I paid more attention to what she was wearing while most men were wishing she was naked.

Kim always dressed the part, very professional and always in a dress or skirt, blouse, and jacket. Her heels were always spiked and those gams always dressed in the finest hosiery.

I thought to myself, if I were to go to work in drag, it would have to be of her caliber of dress, not some second hand mini-skirt from Goodwill.

As we moseyed around goodwill, Suzie hit the men's section and pulled out a very nice Italian made suit from the men's section. It was black with built up shoulders and pleated pants.

Holding it up to herself she stated. "I think this just might fit me."

With that she headed to the dressing room and came back out and showed it off to me.

"What do you think honey, think Desiree would like me in this?" she blurted out.

"If you went as the hot to trot transvestite, I could be your man. I could even buy one of those strap-on dildos you've been begging me to buy.

What do you think?" she asked.

"Sounds good to me but you've got to let everyone that you did my makeup and it was all your idea." I said.

"Oh, without a doubt hun." she convincing said.

With that she went and paid for the suit along with some wingtips she found in the boys section.

"Now, what do you plan on wearing Desiree?" she asked as we got into the car.

"Let's go to the mall and do some real shopping." I grinned.

"We might as well get some practice in first, stop by the house and I'll change into this and you can get all dolled up." she surprised me by saying.

Never the sissy to let a chance to get all dolled up and go out in public, I readily agreed.

With a quick shower and shave, I put a short little silk wrap on and proceeded to do my makeup.

Lashes lush in wet black mascara, brows arched in black with brows highlighted in hues of pink; lips painted full with contrasting shades of fuchsia, and cheeks falsely framed to present the high cheek bones I should have been born with, I finished with two large gold wave shaped earrings. Glancing in the mirror, my cock arched in a semi hard state in admiration of the sweet tranny reflection.

A pair of Donna Karan French cut pantyhose was next and I struggled to tuck cock and balls between the cheeks of my bottom. Next I glided into a very tight waist cincher and finished off the underlings with a black any which a way bra. Fitting in my silicone tits, I loved the way they bounced freely in the unrestricting bra.

I chose a beautiful silk wrap dress in burgundy. Its pendulum waist and slit along the leg oozed femininity. Belted in with a gold buckled deep burgundy belt, my hips suddenly became pronounced instantly turning from slim shapeless man to a woman with curves in all the right places.

Stepping into a pair of five inch black velvety pumps put the shape of dancer's legs into my calves and bum.

Last but not least, I chose one of my strawberry blonde wigs to finish out the look and fluffed it to perfection. A few rings to hide manly hands along with stick on deep red dragon lady nails, I saw nothing but a sexy woman in the mirror as I walked into a cloud of Georgiou perfume.

Stepping out of my dressing room and into Suzie's bathroom, I couldn't believe her transformation. There stood before me was a young man with slicked backed hair and looking quite dapper in her new suit.

"You look quite the lady Desiree, I'm surprised. I always thought of you as being a bit of a tart." she said, giving me the once over.

"Well, a little fancy for work but just perfect for an afternoon of shopping with my gentleman." I replied giving her a peck on the cheek.

With that we headed downtown to visit the high end women's shops. Taking the interstates, Suzie got quite the thrill when several truckers honked in appreciation of the leg show I was giving them in the passenger's side.

"Looks like you have some admirers, Desiree. Too bad it isn't dark enough for a quick pull off so you could stuff some cock in that pretty mouth of yours." she teasingly said.

"Well, there's always tonight." I boldly replied.

Arriving at Saks, Suzie chose valet parking and I felt very much the woman having a nice young man open my door and I teasingly let him have a perfect view of the lace in my French cut pantyhose. I smiled with a wink as his eyes met mine for a brief moment of admiration.

"My, you are but the flirt, Desiree. We might just have to arrange for you two to get together before the day is over." Suzie said as she opened the doors of Saks for me.

Suzie and I went straight for the fine business attire in the women's section and I was a bit confused when she approached a sales lady and without so much as a blink of shyness, told her every detail of our day and plans for Halloween.

"Hello sir or shall we say madam, my name is Karen and I'll be more than pleased to help you today. Might I add, you indeed make a very convincing woman." the sales lady said as she gave me the once over.

"What would please your fancy." she queried.

"Well, I have in mind the likeness of very sophisticated ensemble that our receptionist has worn on several occasions. It had a very short and tight skirt that hugged her body just right with a slit up the back. She wore either a black or white, almost sheer chiffon blouse with a matching tight fitting jacket." I described, as my breasts heaved with nervousness.

"Oh yes, that's a classic look and we do have such right over here. What size are you 12 or 14?" she asked, as we walked over a few isles.

"Twelve if there is any stretch in the fabric." I answered.

She held up exactly what I had described and this one even came with a wide red leather belt with Gucci buckle.

As I marveled over how soft the bright red fabric felt between my fingers, she came back with beautiful chiffon blouse in both black and white.

"Here, try it with both. You can go from day to night with just the change of a top." Karen said.

With that Suzie and I took a well appointed dressing room and she helped me out of my dress and into this hot sexy number. Everything fit like a glove and the white blouse would show my delicates sexily should I get the nerve to do a little flirting at work.

"We should have stopped by the adult store before coming here. You look so good that you definitely deserve some cock." Suzie teased.

I looked at the price of it all and sheepishly pointed out the extravagancy of it all to Suzie, to which she replied with a sly grin. "Guess you'll end up a working girl to cover the expense of such classy taste."

"These will most certainly work, Karen. They fit my sissy husband so perfectly and will make him the belle of the party, no doubt. Now can you show us some fine stockings and lingerie? He'll need the very laciest of bras since you can easily see all through the chiffon." Suzie announced to Karen without a bit of embarrassment.

"Most certainly, he is certainly a lucky girl to have such a generous husband." winked Karen.

Amongst the finest of lingerie, Karen chose a very sexy red lace garter belt and waist cincher and the most delicately laced bra I'd ever seen, complete with a red rose front clasp. For hosiery, she suggested Pam Anderson's Swiss Dot Stockings.

Agreeing to it all, Suzie told her not to forget heels and Karen produced a pair of spiked black patent heels that were out of this world. There name was even sexy. Flippa, she called them; 150mm spiked heels with red leather soles, I felt my heart drop as she placed them on my feet.

"Think you can handle those all day, hun, remember you'll be walking from office to office working on our computers as normal?" asked Suzie.

As I stepped down the soft carpet of Saks, I immediately felt the difference an inch in heel height makes. My steps were deliberately smaller and I was forced to take a much more feminine step with each cross of my legs.

Turning on a dime, I smiled at Suzie and told her I'd do anything to have these heels.

She spied the price of 425.00 dollars per pair and immediately said. "Oh, you'll certainly be doing anything and everything I demand for that price."

Karen thanked us profusely for making her sales day and bid us farewell and Happy Halloween as we completed the checkout.

As we neared the exit of the door, Suzie told me to wait inside a moment and I saw her approach the fine young lad who parked our car. In a moment or two, I saw our car pull up and Suzie waved for me to come on.

As I carefully placed my new feminine treasures in the trunk, Suzie took the driver's seat and mentioned I should ride in back.

I did as told and was a bit shocked when the handsome young man also got into the back seat and immediately began to unbuckle his slacks.

"Well, Desiree, time to start earning your privilege to shop for such upscale women's wear. This young stud has given me a hundred hard earned dollars for you to give him the blow job of a lifetime." Suzie informed me.

I smiled at my young beau and needed little encouragement to do as told. Those heels alone were worth a bucket of cum in my mouth, no matter how Suzie schemed to get her money back.

I took his well defined cock between my ultra curved dragon lady nails and placed his mushroomed head between my painted lips. Twirling tongue under the rim drove the poor boy crazy and when I engulfed his entire cock down my throat, even Suzie was impressed.

Suzie prolonged the eventually filling of my cheeks with his sweet nectar by purposely driving in front of the busiest sections of the mall where I was on display for everyone to see my talents of giving head.

Poor boy nearly shrunk in fear each time a passerby would take notice of the pretty blonde with a cock between her lips. Yet my talents would have him hard again in no time.

After the second or third time he'd swelled in my mouth, he couldn't stand it any longer and drowned my throat and mouth with a load that touted stud. I swallowed eagerly and rose to give him a gently kiss on the mouth, snowballing a bit of his remaining cum into his own.

Suzie returned him to Saks where he thanked us for such a wonderful ride and hoped he'd see us again.

"Well Desiree, let's head to the Love Shack and see if I can find a strap on worthy of a cock sucking slut like you." Suzie said smilingly.

As we strutted into Love Shack adult book store, we got plenty of admiring wolf whistles from patrons of the store and Suzie showed no hesitation in heading straight for the section containing life like replica's of all the famous porn stars.

She took immediately to a molded cock, with a resemblance to a "T" of Eddie Stone's magnificently headed cock.

"Hmmm, this one looks quite a bit like the one you just sucked, does it not, sweet sissy." Suzie declared in a loud voice, clearly stated to embarrass me to the hilt.

"Yes, I can see this one tucked into a pair of my Calvin's, can't you Desiree?" she continued to say.

I just winked and licked my lip glossed lips and nodded approval.

"Good, then we'll get it along with this harness." Suzie stated to the young man who'd stopped by asking if we needed help.

As she paid, Suzie asked me if we should hit the booths for a possible quickie. A big tall black man behind us leaned in and whispered, "If you have the time, I've got the money."

Suzie just grinned at him and immediately took the two of us by her hands and led us to a secluded booth big enough for play.

Dropping in a few dollars into the machine, she told our new found friend, that a hundred would get him the best blowjob he'd ever had or 300 would get him access to a tight piece of ass.

"400 for both sounds good to me." as he peeled off four crisp hundreds and handed it to Suzie, again in a whisper.

"Look at that Desiree, already you've worked off the cost of those Italian heels you fell in love with. I trust you know what to do next." Suzie said grinningly.

With that I peeled off the trousers of my new suitor and was rewarded with the up springing of an already hardened black sword of love. I immediately bathed his manhood with my salivating mouth, getting it good and wet as I knew we had no lube with us. Once I felt it produce the slightest throb, I stood and with long nail ripped a hole in my pantyhose. Without so much as a bit of instruction, I grabbed my ankles and told him to drive it home.

Forced against the wall, I felt as if my ass was going to split wide open when his massive head penetrated my tight ass. He wasted not a moment in slapping his balls against me with such force that just knew this would be a fucking of a lifetime.

Last thing I remember from my pain dazed mind is asking him to please cum in my ass and not ruin my dress.

And cum he did, so much so that I felt my hose becoming wet from crotch to thigh. As he shook off the trailing cum from his cock, a large pud of cum hit square on the tip of my stilettos.

"Better lick that off before it ruins the velvet, honey. Here, I'll scoop the cum from your thighs." Suzie informed me.

As she finger fed me the semen from her hand, she said she was quite impressed and that I indeed did make for a good man fuck.

I sat down, gingerly, beside here and removed my heel and licked it of his cum.

As I looked up, our suitor was again in my face with his softening cock.

"Clean it up, bitch." he said.

I did as told and tasted the nastiness of my unprepared ass as I milked his flaccid cock of every last bit of salty man juice.

"Sorry Desiree, if I'd known you were going to be such an expensive whore today, I'd treated you to an enema before we left. But I suspect that's not the first cock from your ass you've tasted." Suzie said sarcastically.

Once Suzie had fixed my hair and glossed my lips with a fresh coat of pearly pink, we exited the booth, only after quipping. "Well, at least your ass is ready for Eddie Stone now."

Back to the car, we headed home and I was treated to the usual exclamations that she could not believe she'd married such a queer. Adding that she couldn't wait until Monday when all the men at work would find out what a beautiful sissy they had for a computer man. She resigned to the idea of breaking in her new toy saying she didn't want to get it dirty before the big day. With that I went from sexy slutty woman to drab boy again and dreamed all night of my new outfit.

Sunday came and I was surprised when Suzie's friend, Carla, from work who also did nails showed up on our front doorstep.

Suzie greeted her and filled her in with all the details of my coming out debut as Desiree tomorrow at work and that she felt he should really have his nails done professionally.

Carla just beamed with excitement at turning me from man to girly man. With Suzie's, permission she had me strip completely naked and had me lie upon her portable massage table. It was then I felt the familiar warmth of hot wax being applied to my body and soon heard the giggle of the both of them as they peeled off layers of my manhood.

After what seemed like an eternity, I felt cool oil being applied and when I rose up, I saw nothing but pure femininity everywhere, including a cute little patch of hair just about my cock and balls.

She had me lie back down and I felt her paint my toenails a gorgeous color of red polish from L'Oreal called Caught Red Handed.

"Suzie showed me your new heels and outfit. Those heels will give you such awesome toe cleavage and I suspect you'll have to come out of them quite often when the men get a look at you. Men just love painted toe nails." Carla said as she finished me up.

When she had me rise and go to her nail table, I was a bit embarrassed when my cock would not deflate for once I saw my gams and toenails, it was instantly hard.

Sensing my embarrassment Carla comfortingly said, "No worries honey, you are now just another one of us office girls; one with a little something extra. You're not the first man I've transformed you know."

"Yeah, Des, you won't believe who else Carla helps out on a regular basis. But we'll leave that for Monday's surprise." Suzie said temptingly.

My heart was in a flutter as I watch her with great skill turn my short nails into permanent fixtures of femdom. Long and slightly curved, painted in the same tempting red, I wondered silently how I would work a computer tomorrow.

As if she could read my mind, Suzie said abruptly. "Don't worry about typing with those tomorrow; I doubt you will be getting any real work done anyway, although if I have my way, you will most certainly be a working girl."

Once finished, Suzie brought me out a silk robe and we girls just lounged around and watched some chick flicks on television.

Once one had finished, Suzie excused herself for a moment and came back out announcing Carla should close her eyes.

"Open them up girlfriend." Suzie exclaimed standing in front of us in nothing more than a pair of tight boy shorts.

As Carla's eyes opened they fell immediately to Suzie's crotch where she had Eddie Stone securely held by the spandex.

With a flick of her finger, it popped out hard as a rock directly in front of my face.

"Watch how well my sissy sucks cock, Carla." Suzie said as she grasped the back of my head pulling it towards her man hood.

I eagerly went to town and let my wife face fuck me, completely down my throat with every inch of her store bought manliness.

"My my, but he is a good little cock sucking slut." Carla declared.

"Oh, he's definitely a love of all things cock shaped. He likes them small, big, long, hard, soft, wet, nasty. He's nothing more than a cock sucking slut in the tenth degree." Suzie told Carla.

"Well, I'm guessing the term working is going to have a whole new meaning to him tomorrow. I can't wait." said Carla as she packed up her tables and bid us farewell until tomorrow.

"Remember that trick of taping his chest together and how to tuck his sissy cock and balls. And don't forget to give him a good douching." Carla said with a wink as she closed the door.

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bydesireethtttv© 5 comments/ 74568 views/ 31 favorites

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