Sat at the dresser of my hotel room my mind is swirling. My body trembles inside with fear and trepidation. Jenny finishes applying the dark red lipstick to my lips gesturing for me to blot it on some tissue paper.
After doing so, I carefully stand up in the black shiny patent leather heels making sure I don’t stumble or fall as I regain my posture and balance. The heels are the highest I’d worn in a long time so I’m conscious of my stance and equilibrium.
Catching the reflection of myself in the mirror, I feel another wave of excitement flooded over me. I’m standing there looking very much like the whore I’m planning to be. A sheer black with purple trimmed basque with stocking straps give me shape and elegance, the matching sheer full panties trying best to cover my modesty and the flesh coloured stockings with a thick lace top help to elongate my legs perfectly. My makeup finished off the look. Darkened eyes with a well blended and toned foundation, rounded off with the red lipstick expertly applied by Jenny. The dark curls to my hair fall below my shoulders and gave me an extra sultry look.
“Are you ready to go?” Jenny asked.
“Eh-hum,” I reply to confirm.
I open the wardrobe and take out the long black mac on the hanger and slipped it on, button up the three centre button and tie the belt loosely around my waist. Picking up my small clutch bag, I check my room key and phone is in there. Snapping the purse shut I let out a deep exhale.
“Dawn, you’ll be fine. Go on, have fun and tell me all about it later.”
Jenny walks me to the hotel room door before placing a gentle kiss on my cheek as to not affect my makeup, “I’ll wait for you here but take as much time as you want.”
I smile back at her before opening the door on to the corridor.
“I love you.”, I say as Jenny, my wife stands at the door.
“I love you too sweetie,” she replies.
I carefully walk in my heels down the corridor to the lift, press the button and wait for it to arrive. Looking back at Jenny, I see her wave before closing the door. A few seconds later, the lift arrives and I step into it, pressing the button for the fifth floor. Being only two floors above me I arrive within seconds to a bing as the doors open.
Looking at the signage I make my way to room 529. I feel the pull of the straps to my basque, the rub of my stockings against my thighs and the comfortable snug feeling of my panties. I’m beginning to feel wet already.
Upon reaching door 529, I pause, exhale before knocking gently on the door. Within seconds the door opens and I’m greeted by a man dressed in a suit who smiles and gestures for me to enter.
“Please Dawn, do come in.”
I nod and smile back before entering the room.
Looking around, the room is tidy and neat. A bottle of wine and two glasses are on the dresser and music is playing quietly in the background.
My heart sinks as I hear the door shut behind me.
“I’m Chris but you already know that right?” walking passed me towards the dresser and pours some wine into the two glasses. I notice he’s shaking slightly.
“Care for a drink?”
“Sure. Thanks,” I reply taking the glass from his hand.
I hold it in both hands to stop my trembling being evident. He picks up his glass and raises it to toast with me, “Here’s to new adventures.”, Chris says as we chink glasses.
I take a sip and taste the cool taste of the wine. There’s an awkward silence as we look at each other whilst trying to avoid eye contact. After what seems like an age, Chris kağıthane escort tries to lighten the mood.
“Jenny said you were beautiful and she wasn’t lying.”
I blush slightly at his compliment. “Thank you,” I say taking another sip of wine.
Again, another bout of silence falls across the room.
“Sorry, I-I-I’m just not sure how to do this,” Chris mumbles looking down towards his glass.
I can see he’s as nervous as me, so take the opportunity to take the lead.
“I’m not sure either but I know we can have some fun,” saying it with a wry smile.
I step forward taking his glass from his hand and lean over towards the dresser ensuring my ass sticks out slightly and hoping my loosely buttoned mac shows off a bit of my leg. Glancing back at Chris, I see him checking me out.
Staying in that position for longer than I should, I finally make eye contact with him. Doing so, I place my purse on the dresser alongside the glasses and turn back towards him.
Getting close to him so I can hear him breathe, I whisper in his ear, “If you like what you see, I can show you more?”
Leaning back slightly, I see Chris nodding in agreement. Right, it’s now or never.
I slip his suit jacket off and place it in the wardrobe before walking Chris by the hand to the dresser chair lowering him to his seat and place his hands on his knees. Turning away as I walk, I begin to unbutton my jacket. My heart is racing and it feels so exciting.
Turning once again to face him I slowly loosen the belt to my mac and let it slip off my shoulders onto the floor beneath me. I’m stood there in front of him in my basque, panties, stockings and heels, and place my hands to my hips to help extenuate the shape of my body. After a few seconds I carefully lower myself to my knees and crawl towards him on all fours, maintaining eye contact like I’ve seen all the porn stars do.
As I reach the chair, I place a hand on each of his knees before running my hand up his legs towards his zipper. Stopping at the top of his zip I ask, “May I?”
Chris quickly nods looking both excited and nervous.
This is all new to me. I’ve never been in a hotel room dressed like this before let alone be unzipping a man’s trousers like such a slut. Still, I’m here and loving the power I have over Chris.
I unhook his belt and lower the zip. I place one of my carefully manicured hands into his trousers and boxers in search of his cock. It doesn’t take long to find a huge hard lump in there and my slightest touch makes Chris let out a gentle sigh.
Grabbing the base of his cock I ease it out, releasing it from the bounds of his underwear and for the first time I’m greeted up close my a real cock. It feels so warm to the touch and harder than I imagined. The head of his uncut cock glistens slightly with precum from his excitement so far. With a gentle thumb I press the ridge at the underside of his cock helmet and watch him twitch slightly at my slight contact.
I finally know the power a woman can have over a man. I’m now so engrossed in the moment, instinct takes over. I lean forward and place a kiss on the tip of his cock before opening my lips and filling mouth with as much of his cock as possible.
I’ve had plenty of practice giving head to Jenny with her various strapons but to feel this real cock in my mouth fills me with so much sexual energy I feel like I could explode! I regain composure and begin to work that cock like a good whore should.
Jenny taught me well. With one kaman escort hand I cup his balls whilst the other I work along the length of his ever growing cock in time to my moving mouth. As each stroke finishes at the top, I swirl my tongue around the head before engulfing it deep in my mouth and throat with each downstroke. I continue to do this as I hear Chris’s breathing quicken. I’m really doing this. I’m really sucking off a well hung man and by the increasing girth in my mouth and twitches with each tip lick, I think he’s enjoying it too.
Just as I’m gathering a good rhythm, Chris abruptly stops me by holding my head and pulling it off his cock.
“Christ all mighty, I thought I was going to blow my load right there and then!”
With a devilish look in my eye I stand up again before walking towards the bed. Climbing on the bed on all fours once again with my pantied ass facing him, I look back saying,”Well don’t waste it then” and give him a wink.
Chris quickly gets to his feet and comes to the edge of the bed. I feel his hands run up the back of my ankles, along my calves and up to the top of my stockings before tracing the lace stocking tops and on to the suspender straps of my basque. A shudder passes over me in anticipation.
He pushes my knees together before slowly slipping my panties down so they are below my stocking tops, keeping my knees shut. I feel his hand rise up the inside of my thigh before approaching my ass, “I was a little nervous about fucking my first crossdresser but you’ve certainly made it easier for me.”
With that I feel him ease the plug out my ass before a finger skirts across the edge of my slightly gaping ass pussy.
“I especially liked the fact that you’re wearing a little cock cage too. Really adds to the touch of cock slut well.”
Chris flicks a finger on my little chastity cage hanging between my stockinged thighs and I let out a slight whimper. The added excitement of being with my first man whilst wearing a cage dressed this slutty adds to my horny feelings and I can’t help myself.
“Will you fuck me Chris?” I look around at him as he stands behind me.
“Too right I will,” as he fumbles to take the condom out the wrapper.
“You don’t need that. Fuck me without it. I want the first cock I take to be done properly. I want to feel it all!”
I’m shocked by what I’ve just said but equally I’m massively turned on. I can remember Jenny telling me that getting fucked without a condom is the best feeling ever for a woman and I want that feeling too.
“Dawn, you really are the crossdressing slut Jenny said you would be.”, and with that Chris places the buttplug, only just pulled from my ass, into my mouth as I feel the tip of his cock press against my eager pussy.
What exactly had Jenny been telling him? I know they were loosely connected though work but how much as she said?
The taste of my ass juices as well as the pressure from Chris’s cock entering my virgin ass makes me exhale deeply on the plug filling my mouth. I feel him slowly guide his whole length deep inside me making my stomach flip in excitement.
“Oh fuck Dawn, that feels so good.”
He begins to withdraw his cock so only the bulbous tip remains inside me before pushing it back down. My arms give way to the pleasure as I fall to my elbows. His pace quickens as he uses my gurly ass for his (and my) enjoyment. The sensation and feeling of this large cock sliding in and out of me is overwhelming and I feel a string of cum dribble kapaklı escort from my encased clitty. I hold the plug to my mouth and suck hard on it, imagining I was being spit-roasted right now. My slurping noises are increasing in volume, as I noisily gag on the plug.
His hand runs over my basque covered back and down my stockings. A feeling I love when Jenny does so. The panties half way down my legs at the knees prevent me from opening my legs wider, making me feel tighter than I want to be. Still Chris ploughs into me with increasing power and speed. His two hands grip my waist as he rails me harder and harder.
My mind goes to mush as I’m taking to another level of pleasure. I’m here with a stranger dressed like a slutty whore, taking a huge uncovered cock in my ass pussy and I’m loving every minute and inch of it.
I hear Jenny’s voice in my head. ‘You’ll love your first proper cock Dawn, she said whilst stretching my ass with her strapon in our marital bedroom a few days earlier.’ And she was so right.
The sound of Chris moaning brings me back to the moment. With a vice like grip he impales me for one final time as I feel his balls explode through his cock and deep inside me.
“Fuck!!” he lets out a cry in pleasure as his thrust subsides.
More cum drips from my caged clit and into my panties beneath me.
The sensation for me is that of being electrocuted without the pain. The charge felt in me has every nerve and sense tingling and buzzing. I take the plug out my mouth let out a deep grunt in release of my feelings.
Chris takes the plug from hand and promptly places it back in my pussy.
“I want Jenny to see my cum in your ass when you go back. That way she knows her husband is a sissy cock whore that just got fucked properly.”
Hearing Chris say that makes me squirm with shame and excitement. I can’t wait to tell Jenny that I’ve got a load of cum in my pussy and loved it.
“You’d best go. My wife is due to arrive in town soon, so I need to go shower and meet her from the station.”
That’s it. He’s used me like he was paying for it and now he’s rushing off to see his wife. I was his bit on the side, his chasity wearing fuck toy and it feels so good being so.
Chris pulls my panties back up and helps me off the bed. My knees are weak from the pounding I just took. Walking towards the dresser I can feel my cum lubed ass ache after the fucking he just dished out and I try to grip the plug to stop anything dribbling down and to prolong the pleasure.
Grabbing my jacket and purse I head for the door. Chris helps me put the mac on and I fasten it back up. At the door to his room, he stops me by placing a hand on my shoulder.
Chris says, “Sorry if it feels like I’m rushing you away but I can’t have her finding out about this. Besides, we can have more fun next time yeah?”, with a kiss on the lips and a wink, he opens the door and I step out into the corridor once more.
I walk down the corridor back to the lift with a sense of disgust in myself for being used in such a way but a more overwhelming feeling of sexual power and horniness for taking my first cock so well.
As the lift doors open a middle aged couple greet me with disgruntled look on their faces as I step into the lift with them.
Do I look like a prostitute? Yeah, probably.
Do they know I’m a crossdresser? Probably not as I’m more than passable.
Do they know I’ve just had my ass cherry taken? Only if my wriggling or the seeping cum down my inner thigh gives it away.
Do I care? Not a jot!
At floor two, I step out confidently and purposefully in these fuck me heels and stride down to the room where my wife is waiting for me to tell her the details and I won’t leave anything out. Especially not the bit about me wanting cock again. I’m sure she’ll understand.
