I sit at my vanity, putting on my makeup. It’s my night of the week to go out. As always, I wear my black wig, and tight black skirt with a nice blouse, not that I have that many to choose from. I stuff my bra with cotton and pull my pantyhose over my black thong panties, checking to make sure I’m well tucked. I’m thirty-six and barely passable, so I can’t be too careful.
I sit in medium-sized hotel lobbies, there are four in town I like. I frequent a different one each time I go out. Can’t afford to let the staff know my face. My fetish is to get picked up and get paid for sex. The only other place I cross-dress is at home.
I try to get there around eight-thirty when the guys usually come in after eating or drinking with clients. I can spot a traveling salesman a mile away.
I’m sitting in a lobby drinking coffee, pretending to read a newspaper as I scan for men coming in. I see a guy looking at me, and I smile at him. He looks down when I smile, so I wait for him to look back up and I smile at him again.
He smiles back at me this time, and I uncross my legs. He keeps looking, so I smile again and get up. I wiggle my ass at him as I walk towards the bar. He follows me into the bar and I wait for him to move towards me.
“Looking for some company?” he asks nonchalantly.
I smile. “Could be,” I reply.
He buys me a drink and we find a secluded table. He asks the usual questions and tells me he’s on the road a lot on business. I tell him I live in town and wait for his next move. I feel his hand touch my thigh.
“It gets lonely being on the road all week,” he says.
I think he wants me.
“If you have a room,” I say, “$50 buys my company.”
“Who could resist a lovely lady like you?” he signals his desire.
“I’m not your usual lady,” I warn him, just to make sure.
“That’s obvious,” he says.
I don’t take that as a compliment, but I’m well aware that I’m barely passable. At least he knows what’s under my skirt. He takes my hand and I stand up and smile. We get on the elevator, no one else is riding. His hand slips under my skirt and I open my legs a little.
His hand touches my bottom, and my cock begins to grow. His other hand comes up the front of my skirt and brushes my cock. He places his hand on it. I touch the front of his pants, smiling that his cock is already hard for me.
The elevator stops, and as the door opens, I lift the back of my skirt. He gropes me all the way down the hall as I giggle until we reach his door. As soon as we’re in, I take my skirt off as he drops his trousers.
I’m hungry and go straight to his cock, which is very thick and very hard. I lick it good before taking it in my mouth. I love it when he moans for me and tells me what a good little cock sucker I am.
“Thank you,” I say, and gobble him back up.
I love sucking cock and hope he cums in my mouth.
Then he pulls back. “I want to fuck you,” he says.
I stand up, a little disappointed, but I’m here on his dime.
“Wanna lie on the bed?” I ask as I get the lube and condom from my clutch purse.
I put a condom in my mouth and roll it down his cock, just like I practice at home with my dildos.
“You’re pretty good at that,” he compliments.
“Practice makes perfect.” I giggle and push my pantyhose to my knees.
I put some lube on my hand and straddle him, rubbing my hand up around his cock and holding it.
I have no trouble positioning him. He’s been rock hard since we left the bar. I work his cock into me, shuddering as my hole opens and his thick cock splits me.
I sit right down on him and wait, my stiff cock standing out as I relax myself around him. He grabs my hips as I move my tight ass up and down on him.
“Fuck, you feel damn good up there,” he says as he pushes up into me.
“Oh, fuck… your cock is so thick,” I tell him, and I’m not lying.
“Oh, God,” I moan, “you’re going to make me cum if you don’t slow down.”
He can’t slow down, and brings me to an anal orgasm, my favorite way to cum. He fucks me hard as my cum shoots onto his chest in big spurts.
I feel his cock spasm and I know he’s cumming inside me. I move up and down on him faster, milking him and making sure he’s empty before we stop moving.
The condom slips off him and stays in my ass as I kneel beside him to lick my cum off his chest. I then clean his cock with my tongue and mouth as he tells me how pretty I am.
I go into the bathroom to pull the condom out of my ass and clean myself up. Fifteen minutes later, I come back out clean and dressed. He hands me $70 and says, “You were great, darling. I hope I see you next time I’m in town.”
“Don’t be shy if you see me,” I tell him. “I like regulars.”
He gives me a hug and I want him to kiss me out the door, but he doesn’t. They never do. Still, I happily skip down the hall $70 richer with a happy ass and having cum myself.
It’s the best a barely passable crossdresser like me can hope for. I return to my apartment a happy ‘girl’, looking forward to next week.
