The Secret Night (NSFW Sissy Story)

The Secret Night

I’d stayed at many hotels but walking into this one and trying to keep my composure was proving hard.

The extra luggage I’m pulling, I think, makes me look extremely suspicious. Normal business types in town for a meeting would have a single bag, but I’ve got a big old case with me.

The Kinda suitcase you’d imagine a woman to be wheeling around! Much too big for a single man on a business trip!

“Mr. Hudson,” The receptions says with a smile that makes me feel uncomfortable. “Please enjoy your stay!”

Taking the key off the young man, I give him a wry smile in return.

I couldn’t help but worried he’d seen this all before! Does he know I’m a crossdresser and my bags are full of wigs, dresses, and makeup!?

“Thanks,” I sheepishly reply and turn towards the lifts.

Swiftly making my way upstairs and to my room, I still felt so hot under the collar!

Everybody I passed would give me a smile and say hello. It’s like they all knew what I had planned for tonight and they all wanted to pass judgment on me!

Reaching my room and slamming the door closed behind me, I let out a long sigh of relief.

No one knows I’ve got a guy coming to meet me later!

Wheeling my suitcase in, I throw it up onto the bed.

The meeting is starting soon and I’d have to make my way to the conference center, but before that, I’d need to set out my stuff.

I’d only have around an hour to get dressed and dolled up before Jamie arrives! He ain’t guna wanna see me in my drab male look.

Being super proactive, I’d already got a full body wax.

That meant I didn’t have to shave, I just had to get into my wig, clothing and do my makeup.

Although that was another reason I was feeling so self-conscious.

I felt the woman in my office could tell I’d been waxed and with the fact I’ve been having to wear women's roll-on deodorant too, I couldn’t help but feel it was obvious!

“Argh,” I groan, unzipping my suitcase. “Karen mentioned how nice my eyebrows are…!”

Rubbing at my face in frustration, I bet she’s even more certain that I’m a closet crossdresser!

“Going to have to avoid her today,” I continue, talking to myself.

Having set everything out in preparation for later, I grab my work gear and head to the conference room.

Taking my seat at the table, Karen seems to purposely sit opposite me.

As the meeting slowly rolls on, I feel my phone vibrate in my pocket. Reaching in, I secretly look at the message.

‘Hi Sexy Kitten’ the first message reads.

Instantly getting awkward about it, I look around the room to see if anyone has noticed me getting a text.

Lucky for me and my red face, no one is evening looking at me. I look down again to read more.

‘Can’t wait to finally meet my Kitten tonight,’ the message reads ‘You better be sexy for daddy!’

Trying to hide my smile, I reply with the winky face emoji.

“John….?” I then hear Karen say from across the table. “Please pay attention.”

Nervously looking up, I fumble my phone into my pocket and give Karen a frantic nod.

Gently shaking her head from side to side, I wanted to kick her shins under the table.

Making it look like I was reading the PowerPoint slides on the monitor, I couldn’t stop thinking about how I wanted to gloat that I’m getting dick later and she won’t be!

A small smile forms on my face.

I’ve found a man before her and I’m a man myself!

For the rest of the meeting, I kept daydreaming.

I wanted to turn to Karen and tell her I’m getting action tonight. I wanted to tell her that maybe she should grow a dick, to attract men, rather than just being a dick!

When the meeting finialy finished, I made my excuses to leave the after drinks and head back to my room. Just as I leave the conference room, my phone vibrates again.

Pulling it out and swiping open the message, It’s just a picture of Jamie's dick!

“Argh,” I blurt out, hiding the image from my co-workers.

“Are you ok…?” Geoffery then asks, now walking beside me. “You seem a little tense today. Is something going on at home with the wife…?”

“Noooooo,” I instantly reply, shaking my head from side to side. “Everything’s fine between me and the wife!”

“Alright then,” Geoff responds, patting me on the back. “You let me know if my top salesman needs to talk!”

“Thanks…..,” I answer, still thinking about the dick picture on my phone.

Saying my goodbyes, I quickly head upstairs to my room.

Knowing I didn’t have long to get into my feminine persona, I throw off my shirt and pants.

Balling them up and stuffing them into my bag, I rush into the bathroom to find my shapewear.

The skin-colored hip and bum enhancers really worked to add curves. Matching that with my new breasts forms, I looked very convincing once in my bra and panties.

Soon having my fishnets hooked to my garter, I started battling with my corset.

Once I’d got it all hooked up and tied tight, I knew my figure was complete.

Standing in front of the bathroom mirror, from legs to chest, I looked completely feminine.

The bounce of my chest to the size of my ass, all wrapped up in sexy black lacey lingerie. My body is going to drive Jamie wild!

Now taking the time to apply my makeup, lashes, nails I finish off the transformation with my long blonde wig.

Brushing it out completely straight, I check myself out in the mirror.

“Hello, sexy Kitten,” I say to my reflection, making a claw with one hand.

Then a gentle tap at my hotel room door makes me jump. Quickly spraying some of my wife's perfume, I rush to do the door.

Awkwardly brushing blonde hair from my face, I look into the peephole.

I’d never met Jamie before, so this was the first time I’d seen him for real.

He looked a lot bigger than I expected!

Placing my hand on the doorknob, I felt my heart racing. Was I really going to let this man see me!? Was I really going to have sex with him!?

“Kitty…..?” he whispers through the door. “I’m here!”

Flashes of worry hit my mind as I smell my wife's perfume on myself. How would she feel if she knew her husband was about to suck dick….!?

Knocking louder, I could tell Jamie was getting impatient.

“Kitty!” He gripes, knocking on the door again.

Worried someone might see him, I open the door to him and awkwardly present my body to him.

For a second, we just both look each other up and down.

He stands about a foot taller than me and is wider too.

“Hi,” he says, eventually smiling and looking up from my chest.

“Hello,” I reply, sternly in my normal male voice.

Not waiting for me to move, Jamie pushes past me and enters my room. I slowly close the door behind him and try my best to seem sexy and feminine.

“Kitty,” he says, looking around, then back at me. “Please use your girly voice around me.”

Like a naughty girl, I just with slumped shoulders at his telling off.

“You do look super sexy!” he continues, moving to stand directly in front of me. “Go put your heels on!”

Looking down at my feet, I’d totally forgotten my heels!

“Oh so sorry!” I cry, fumbling into the bathroom and slipping them on.

Seconds later, I stumble back into the room with the heels pinching at my feet.

Lucky the wife's heels fit me. Not so lucky I never got a chance to practice wearing them!

Approving my look, Jamies sits on the edge of the bed and beacons me to him.

Slowly taking one step at a time, I flick my hair back like I’d see sexy girls do on the TV

“Yes Kitty!” he shouts, rubbing his crotch.

His hands move up onto my tighs as stop in front of him. It was such a surreal experience having powerful man-sized hands touching my hairless body.

It felt so dirty as his hands went to my ass and squeezed it hard!

My cock reacted so quickly. My erection was easy to see!

“Good,” Jamie grins, softly stroking my cock.

Having a man touch my erection for the first time, I step backward unsure.

Not pleased, Jamie grabs me by the waist and brings me back in close.

With his large hands holding my quivering body, I couldn’t bring myself to look at him. My body clearly wanted his attention, but I was still super worried about being with a man for the first time.

“Lighten up Kitty,” he comments, gently taking my hand and kissing it. “We can go as slow as your want.”

Reassured, I give him a gentle smile.

Smiling back, he unbuckles his belt and quickly pulls down his pants.

Standing between his open legs, I could see his viper nestled in his boxers. He’s just as excited as I am!

“Touch it,” he says, pulling down his boxers and letting it sprint up to attention.

Impressed with his size, I felt the usual inadequate feelings about my own.

Whilst I was thinking how small I was compared, Jamie takes hold of my hand and forces me down on my knees in front of him.

Letting out a small squeal as I do, I’m left staring at his viper face to face.

The smell of his aftershave coming from his cock was clear as day. It was the sort of thing I’d wear for my wife.

The irony wasn’t lost of me.

Me wearing my wife's perfume and him wearing mine, it was like I’d become…..the wife.

That thought only spurred me on. I’d wanted to feel like that for as long as I remember!

Wrapping my hands around his viper, my hands seemed dainty.

Gently pulling his foreskin back, Jamie lets out a moan of pleasure.

“Kitty!” he groans, putting his hand onto the back of my head. “Kiss it!”

Having never sucked a dick before, I wasn’t very sure how to start.

Pushing my face towards him, I stick out my tongue and lick his head like it’s a lollypop.

Removing the pressure on my head, I take a moment to savor the taste of another man's cock on my tongue.

It tasted salty.

Feeling turned on, I begin to slowly jerk him off.

As he leaned back and groaned with pleasure, I decided it was time to put him into my mouth.

Covering my teeth with my lips, I gently slide his throbbing head into my mouth.

Clamping down with my lips, bob up and down on his cock.

The sensations filling my nose, mouth and brain were a little overwhelming.

Here I am….sucking a cock….and enjoying it!

That’s when Jamie forces my head down and his cock deeper into my mouth.

Unable to take him, I splutter and gag.

Allowing me to take his cock out of my mouth, I cough and gag some more.

“Kitty!” He whines, upset. “….and you were doing so well!”

Wiping salvia from my lips, I look up at him worried. Was he going to punish me…?

Instantly standing up, Jamie roughly grabs my arms and spins me on the spot.

Bending me over, so my ass was pointing in his direction, he laughs.

“Naughty!” He groans, cracking my left ass cheek with his hand.

The pain was so intense, I jumped up and squealed as my arse cheek continued to sting. Even the extra padding on my ass wanted enough to stop him!

Desperate to rub my punished ass cheek, he doesn’t allow me to move.

Forcing his hard body and hard cock against me from behind, she gently kisses me on the back of the neck.

The prickles of his face hair send shivers down my spine.

One kiss after another, he grinds his erect cock into my back.

“Be a bad Kitty,” he says, gently placing his hand on my sore ass cheek. “You get punished!”

Using his powerful hands to spin me around on the spot, my wig falls in front of my eyes.

Brushing the hair from my face, he gives me a smile and gently touches my cheeks.

“Make daddy cum!” he commands, pushing me down to my knees.

Fearing punishment, I don’t hesitate to get my hands around his viper.

Sucking, kissing, and bobbing up and down on his shaft, I’m pleased to hear him moan out in pleasure.

“Kitty!” he groans, pushing himself deep into my mouth “KITTY!”

Feeling his cock throb and pulsate, I knew what was coming!

That didn’t stop me from gagging and coughing, as his warm seed coated my entire mouth.

Trying my best to take it all in, I couldn’t believe how thick and how strong it tasted.

If I wasn’t so turned on by the fact I’ve got a man cumming in my mouth I would have been so disgusted!

Swallowing it all down, I thought popped into my head.

Men pleasured: Karen zero, Kitty one!

“GOOOD GIRL!” he says, with a deeply satisfied moan. “I can’t wait to take your virginity!”

Licking the last bits of the season from his cock, as my wife does, I’m instantly worried.

Looking up, I give him a worried look.

“Don’t look at me like that Kitty,” he says, gently stroking my hair. “I think you’re ready to take your real place in life. A little slutty sissy!”