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Charlene is waiting on the stairs.
1.3k words
4.44
107.9k
15

Part 1 of the 4 part series

Updated 06/07/2023
Created 09/03/2012
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*

It had been a shitty week. Nagging clients, bosses that didn't want to hear the truth, and 60 hours in that bandbox of an office.

But it was all over, for this week anyway. I was nearly home and I hoped Charlene would be waiting.

As I went to grab my front door handle, I noticed it was ajar. I pushed in and stepped into the foyer, as I started to yell for my girlfriend. Before I could get a word out, I saw her, sitting on the stairs.

"Hello, dear," she said. "I'm glad you are home."

Looking at her, I was glad to be home, too. She was sitting on the stairs, her long legs covered in thigh-high stockings and her feet in a sexy pair of heels. A black lace-fringed half slip covered her white satin panties, which matched her bra.

"I love your outfit," I said as I sat my briefcase on a chair. "You look lovely."

Her face beamed, thrilled by the compliment.

"Have you been here long?" I asked.

"Just long enough to get ready for you," she said.

As I bent to kiss her, I let my hand trail along her nylon-covered inner thigh. As our lips met, my fingers brushed past her cock as it stiffened in her panties. A moan escaped her lips and she gently pushed her tongue into my mouth. My hand continued upward, sliding over her slip and across her smooth belly. My fingers caressed her breast through the fabric of her bra as her nipple stiffened under my manipulation.

After a moment, I broke our kiss and stood up, my hand still on her breast.

"And just what did you have in mind?" I asked.

"Anything you desire, baby," she replied, as her hand slid up my pants and caressed my erection through the fabric. "I know you've had a tough week, I've hardly seen you."

***

Charlene and I been dating for several months, after meeting online. Nearing my 40th birthday and coming off a bruising divorce, I'd finally come to the realization that my desire for mansex was more than just an occasional masturbatory fantasy.

As I browsed the online ads, I was drawn to Charles' profile. He was a cross dresser, though he rarely went so far as to wear make-up and wigs anymore. After striking up a friendship, I started to realize that Charlene, as she liked to be called when she dressed, was the best of both worlds.

Her wonderfully smooth body and round feminine ass was the perfect platform for the lovely lingerie she wore. When she sent me a photo of her completely smooth mushroom-headed cock nearly bursting from a little pair of thong panties, I knew I had to have her.

We met in a hotel near our homes and as I staggered to my car hours later, I knew we would be together from then on.

***

Charlene unzipped my pants and fished my erection from my boxers. She kissed the tip, licking a bubble of pre-cum that had already started to flow. With one swift move, she took me entirely into her mouth, her nose pressing against my abdomen.

I moaned loudly, and my hand found the back of her head, holding her deep on my cock for a few seconds. When I released my grip, she started into a series of long, slow strokes, letting all but the tip of my cock slip from her mouth before taking me as deep as she could.

"Mmmmmm. That's it," I said, as I watched her work my dick.

Charlene stopped her work, let my cock slip from been her lips and reached for my belt. With it undone, she pushed my pants and underwear down around my knees.

She reached between her legs and ran a finger inside her panties. When she pulled it out, I could see the lube shining on her finger.

As she kissed and licked at my shaft, she reached through my legs and pushed her slick finger between my cheeks. I moaned when her finger brushed past my rosebud.

She reattached herself onto my dick head, running her tongue around it as she she pushed gently at my asshole. When her finger slipped past my sphincter and into my rectum, she swallowed my shaft.

I damn near emptied my balls.

"Oh, baby, that's so good," I said with a moan. "So, so good."

Charlene held my cock in her mouth, lightly running her tongue across the underside as she fucked me first with one finger and then with two.

It was pure heaven, though I knew I would come soon if I didn't stop her.

I stepped back and her fingers fell from my bottom as my dick slipped from her lips.

I pulled her up to me, and kissed her deeply. I could taste my cock on her tongue as I pulled her close.

My hands found her ass. I pulled her to me, our cocks touching through the sheer fabric of her panties.

Without warning, I spun her around, my cock nestling between her cheeks as my arms surrounded her. My right hand slid into her panties and gripped her smooth cock, while my left rubbed her nipple through her bra.

My lips found her ear, and I sucked at her lobe.

"I have to have you," I whispered. "I can't wait."

She arched her back, pushing her ass back onto my erection and increasing my grip on her dick.

"Take me, baby." she said. "Fuck me. Give me your hard dick."

I pushed her toward the stairs and she dropped to her knees with her panty-covered bottom sticking out at me. I flipped her slip up onto her lower back and grabbed her underwear at the hips.

With one quick tug, her panties fell to her knees, revealing the object of my desire, her round, smooth and already lubed ass. I kicked off my shoes and stepped out of my pants. My cock jutted out from underneath my dress shirt as I pushed it into her crack.

She moaned with desire as I rubbed my dick in her channel, the lube she'd applied before I got home coating my shaft. When I was well-lubed, I lined up my cock with her rosebud and pushed gently.

My dick head slipped past her outer wall and into her sphincter. We moaned in unison.

My cock sank to its full depth, my balls swinging to touch hers as they hung between her legs.

I pulled back slowly, feeling her silky bottom grip on my cock. My cock popped from her hole, and she shuddered.

"Don't tease me, baby," she said with a whimper. "Give me that dick."

I pushed back in and set into a rhythm, fucking her ass with long, deep strokes. As I fucked her, my hands gripped her hips through the fabric of her half-slip.

She moaned in rhythm to my strokes, a series of "ohs" escaping her lips.

As I watched my cock disappear in her ass, I knew I wouldn't last long. The sight of her bent over on the stairs, coupled with the feeling of the back of her nylon covered thighs against the front of mine had my balls churning and my heart pounding.

"I can't hold out," I said as my balls tightened to my body and my cock swelled inside her. "I'm going to come."

With a final push, I buried my dick deep in her as I filed her hole with my seed. My fingers dug into her hips as my body shook with orgasm.

Soon, the waves of pleasure subsided and my cock softened. I loosened my grip and let my cock skip from inside her. When I did, a steam of cum ran from her bottom, landing on the panties bunched between her knees.

I leaned over and kissed her lower back just above her slip before helping her to an upright position on her knees. I pulled her panties up over her ass, though on the front, her cock jutted out of the top of her underwear.

"Thank you, baby," I said. "I needed that."

Charlene turned and gave me a kiss.

"Let's go upstairs," she said. "We've got all weekend to ourselves."

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5 Comments
Joannemitchell67Joannemitchell67over 11 years ago
Glorious

I loved hearing it from the mans point of view too. As a long time Bi crossdresser (since age 12), I adore the oppurtunity to be a "Charlene".

I know exactly how it feels from my perspective and I adored reading about such a delicious encounter from the mans perspective. :-)

Beautiful.

Joanne

joannemitchell67@yahoo.com

AnonymousAnonymousover 11 years ago
wow

very very hot i just love gettin dressed up in womens longerie and clothes wig make up omg thats hot

toni49toni49over 11 years ago

real nice story nice and sexy

AnonymousAnonymousover 11 years ago
love this story

i love the lingerie and loving sex. i so like charlene

cmoreheadcmoreheadover 11 years ago
Loved it!

I very much enjoyed the story. I like how it was written from the man's point of view.

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