Friday Girl

Story Info
He is lured to the edge of his limits as a man.
1.2k words
3.83
125.4k
6
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

4pm, on Friday, and I have my little tapestry valise packed and ready. I shut off my computer and put on my coat. It’s the coat I bought in the women’s section of the Gap. The way it fits, a little too snugly and not quite big enough, it seems very obvious to me. I slip on my soft knit gloves, which hide the pink polish I’ve applied to my nails. I did them at my desk, with the office door closed, like Charlotte told me. My toes I did last night, as we watched television. I stop to say goodnight to my assistant, Tracy. She looks up from her computer and smiles and I blush. I wonder, as I always do lately, if she knows. She looks at the little tapestry valise in my gloved hand and then back at my face. She wishes me a good evening, and a good weekend. I return the wish, and hurry to the elevator.

The motel is about fifteen miles from the suburb where Charlotte and I live. It’s one of those rundown looking places on the side of the highway. The reservation is already made, and I retrieve the key from the office. The night-manager looks me over briefly, and I see disgust and curiosity register on his face, before he dismisses me completely.

It’s at the end of the row, the room Charlotte has rented. I unlock the door, step inside, and feel my heart catch. There is no telling what she has planned for tonight, what she’s decided she’d like me to do. I am helpless in her hands, and her desire to feminize me has rendered me her slave. Quickly, I strip and shower. My body has been waxed and smooth for some time now. The lacy panties, the garters, the stockings—all in white. The pink lipstick and lipliner. The blush beneath my cheekbones. I do my eyes dark. I clip the fall of her hair to my own. I slip my arms through the push-up bra and I actually have cleavage.

Inside a pair of white platform pumps, I feel sexy and vulnerable. I turn down the bed and lie down. The heat is just beginning to warm the room.

With a shaky hand, I’d already lit the votive candles Charlotte instructed me to light. I wish I had a drink, or a cigarette, but I have neither. The light flickers over the smooth skin of my flat tummy and I touch my painted fingers just beneath my pierced navel. I touch my crotch, lightly, and feel myself swell. Distracting myself, I rub one stiff little nipple against the irritating lace of my bra-cup.

A key in the door, and I’m on my belly. It’s Charlotte, of course, and she’s with someone else. A man, I can tell, from his voice, the way the air changes in the room, and he’s talking to her about me. He’s confirming what he can do to me for the money he’s paid. There is the sound of them making out behind me. I don’t want to look. He is groaning with pleasure and shame burns me alive. He has dropped and removed his pants from the sounds I hear, and Charlotte is complimenting him, his size, his hardness. She calls on me to turn around and have a look.

She says, Look at him, Michael. Look at how big he is. How beautiful.

Looking back, I don’t want to see his face. I am too embarrassed. So I stare only at his penis, large and dark, wrapped in Charlotte’s delicate pale hand.

He is asking again, with difficulty, what he can do. My head is back down in the pillow. I hear Charlotte tell him that he can fuck me.

She says, You can fuck my pretty little pussy up the ass.

In spite of his excitement, the man laughs. He is on the bed already, rubbing my cheeks with his large hands. He tugs at the panties, ignoring the little satin ties over my hips, yanking them off me. He slaps me once, twice, three times very hard on my ass. I feel the tears in my eyes. Charlotte tells him to wait just a moment. She wants to put a condom on him. She promises to suck him a little first if he agrees to wear protection. I listen while she performs all this on the man kneeling behind me.

There is the sound of him spitting, and then his fingers in my tight hole. He spits again, and shoves more fingers inside me. He asks me if I’m clean, and he demands to hear me say it.

I say, Yes sir I’m clean.

He growls, Say it again.

I say, Yes sir I’m clean.

Bitch, he says. I’m going to fuck your ass.

He sounds angry, and repeats how he is going to fuck my ass, only the second time he says, I’m going to rape your ass. I feel the head of his cock against me. It’s tip is blunt, slick, and cold from the rubber he’s wearing. He calls me a faggot, a sissy, a whore. He shoves his cock an inch inside me, groans, collects himself, and pushes it in further. I can feel the delicate tissues back there tearing, burning, bleeding. Charlotte, I moan, Charlotte. I’m not even thinking when I call out to her. She is stroking the back of my hand, finger clenching the cheap quilt. She is telling me to be quiet, to relax, to let what must happen just happen.

Too tight, I’m too tight, and I know it, but there is nothing I can do about it. I’m tensed up against the man pushing his cock inside my ass. At first I think I’m fighting against what’s happening, and maybe I am, just a little. But it’s my own erection that is tightening the muscles back there. My orgasm is spontaneous, and shattering, and in it’s wake his cock pushes easily through my suddenly relaxed and traumatized tissues. I can feel it, hot now even through the condom, splitting me open hopelessly.

Fucking me now, he’s lifted my fragile hips off the bed. I am his plaything, his sex-doll, his delicate slut. I’m done for now, and the knowledge makes me cum again, only this time it’s without an erection, and the contractions inside my body, which sheathes his thrusting cock, bring him, too, to the point of no return. He holds me motionless, thrust as deeply inside as he can go, and then slams frantically into my passive body, which suddenly wants all of him, all of him it can take, and somehow even that is not yet enough.

Sometime later, I am softly crying. My head is lying in Charlotte’s lap and I can feel the tears under my cheek. Her thighs are soft and naked and she is stroking the side of my face. She is telling me that everything is okay, that she loves me, that I am wonderful. What happened after the black man came inside me, I don’t remember. I fell, it seemed, into a steep decline of ecstasy. I woke here, in Charlotte’s lap, wrecked and bleeding. I am licking at her pussy as I weep. She tells me how amazing it feels. On my tongue I taste another man’s sperm and the hint of my own shit. I want to die now and I tell Charlotte of my wish and she says how beautiful I am just like this and then she cums.

Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Dressed To Please Kate Husband and wife both enjoy the femme side.in Transgender & Crossdressers
Turning Him Into A Whore She turns him into a trick turning whore.in Transgender & Crossdressers
Pretty in Pink Ch. 01 I catch my bf wearing lingerie...and decide to roll with it!in Transgender & Crossdressers
Lisa and Jack: Crossdress Fun Lisa explores a new fetish to liven up their sex life.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
More Stories