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By Edward Stiles
My "date" pushed my back against the wall. It was OK. I don't mind a little rough stuff, as long as it doesn't go too far.
He put his hand between my legs and fondled my pantied balls. He pressed his lips to my painted ones. We kissed--necked. He tasted vaguely of stale cigarette smoke. He felt my bra cups but the only thing in them was a gold lipstick tube. He fondled me again and ran his hand up over my limp penis.
"You feel nice in your little panties," he said. "Hot."
As we walked past the kitchen entrance I offered him a drink. I certainly needed one. Another one. After douching myself, just in case, and showering and putting on my makeup and dressing, I'd had two drinks--flavored vodka--while sitting on a kitchen stool with my stockinged thighs crossed, waiting.
He told me he didn't drink. I've made a couple of observations over the years, while entertaining other men. One, once they hit their mid-forties most men turn bisexual; and two, most claim they don't drink. This astounds me. They're cheating on their wives with another man, a crossdressed one in my case, and they don't need a drink to calm their nerves? This worries me more than astounds. What kind of men are these?
"Mind if I have one?"
"OK. But make it a quick one. I only have a half-hour," he explained, as he had previously in his email. This was another thing about these men, these dates: they almost always had a narrow window for sexual encounters. The wife and kids were waiting.
As I poured myself another vodka, over ice, the man pointed at my steps, to his right. "I want to fuck you. There."
"There?"
"On your staircase."
I'd never been fucked on stairs before. But now that I looked at it it made sense. You'd kneel on one step and rest your arms on the next one up. Your partner would stand behind you. Because of my dogs, however, the steps were covered with a coarse, industrial-grade carpeting. It would probably tear the knees of my thigh-highs. Black nylon, for some reason, just doesn't hold up.
"OK," I agreed. He'd only asked, in his email, for a blowjob, but I was always up for a fuck. I was always ready to bottom for one of my dates, my clients. "It'll cost you sixty dollars, though."
"I know that!" he said defensively. All well and good but some guys think they can fuck you for the cost of a blowjob--twenty dollars. I may sound like a cheap slut, a whore, but I'm not. It's just the reality of the market. Men are cheap, what can I say? "I get a blowjob for that, too, right?"
I nodded.
"Well finish your drink and get on your knees and make me hard. Then I'll fuck you."
I set my glass down, empty of everything but ice, and came over and dropped to my knees in front of him and began opening his pants. His cock flopped out. It was engorged but not yet erect. It was clean--freshly showered. I took it in my mouth. I fondled his balls as I sucked him. I let go of the base of his cock and reached around with my free hand and kneaded his ass. It was firm, round. Most men his age had gone flabby, soft. I sucked him, expertly, for what seemed like five minutes, though it may have been less.
He told me to stop and get on the stairs. "You have lube?"
I pointed behind myself at the nearest kitchen drawer. "In there."
"What a little whore you are," he said, as he went to it. I assume by this he meant only a "whore" would keep a tube of K-Y jelly in a kitchen drawer. But you never know how things might play out. Some guys, in their narrow time window, want to fuck you on the livingroom couch. I'm open to just about anything, and remain prepared.
I got off my knees only long enough to position myself on the steps. As he lubed his cock up he told me to go one higher, and I did. He told me to spread my legs wider. He told me to pull my panties down. Stretched, now, between my wide knees, I wondered if they would even fit when I pulled them back up.
He put the head of his circumcised cock to my hole and pushed in. He went in easily. "You don't have condoms?" he asked, while halfway in me.
"No, I have them."
He pushed deeper, all the way in, and that was all he said about safe sex. About possibly practicing it. It depended on the man but I usually didn't mind having a bare cock in me. They were all married, I figured, and healthy. Besides, I love it when a man ejaculates his semen in me. I love carrying it around in me afterwards, knowing it's there. The man may leave and I'll never see him again, but a part of him remains in me. For a while anyway.
He began fucking me, hard. I moaned with each thrust but he told me to shut up so I kept my pleasure-cries bottled up, inside me. My elbows were rubbing on the carpet and so were my knees. I knelt there envisioning holes forming in my stockings. $15.99 down the drain. Oh well...
I wasn't really doing this for the money. Charging men for a BJ or a fuck just added spice to the encounter. I'll leave it to the psychologists to explain why I like being a crossdressing whore. Actually I went to a shrink once and he had no answer. I stopped going.
He fucked me silently, aside from the slapping flesh. No moans. No cries. Occasionally he slapped my bottom. There was that.
He came in me silently, too. I only knew he'd finished when he pulled out. I looked over my shoulder at him. "Did you cum in me?"
He didn't reply. I took this as a yes. His glossy penis was already drooping, and there was a small dot of white sperm at its tip. I wanted to suck it out of him but he was already pulling his pants up.
"I'll get a towel and clean us up," I offered. And I got up off the steps, my stockings in tatters and my knees red, and went and got a wet dish towel. I wiped the lube from my crack and then went to clean off his penis. But he was securing his belt by then. I couldn't imagine, having twice been married myself: going home to the wife with your cock covered in dried lube and smelling faintly fecal.
Without my asking the man fished three twenties out of his pocket and slapped them on the counter, as if a resentful gambler who'd just lost a bet. He hurried toward the door. Even though, by the stove clock he still had ten minutes left in his thirty minute window.
"Come back any time," I said brightly, encouragingly, as he turned the lock on my front door. He mumbled something noncommittal. He left. I watched until he'd backed out of my driveway. I knew I'd never see him again.
I took the sixty dollars and stuffed it in a ceramic cookie jar in one of my kitchen cabinets. Money for a rainy day. I was feeling very fem in my wig and bra and panties and ruined stockings. I still had the ghost of his penis inside me along with the reality of his load of sperm. Large, small, I didn't know. It was deep inside me, however. Warming me.
I fixed myself another drink--a double--and opened my laptop. Another man said he could come over at nine, thirty-five minutes away. He might show. Or he could be a faker, or lose his nerve at the last minute. I gave it about a 33% chance of him showing.
Still, I had to change my stockings.