The cell phone nearly slipped out of my wet fingers and I set it on the bed as I wiped my hands on my legs. I cursed myself for being so nervous. I had not even done anything, yet. I was only considering it. Had been considering it for two days.

I glanced over at the laptop screen flickering from desk. The photo taunted me and I felt my dick twitch, still half-hard from the last time I’d looked at it.

I grabbed my phone and paced the short span of my room at the Chicago Hilton Hotel, wondering what had possessed me to search Craigslist for “erotic services.” It had been idle curiosity, until the photo had jumped out at me. I stopped in front of the monitor. The screen showed a woman kneeling on a bed, nude but for a huge strap-on dildo.

I dialed the number, rationalizing that it wouldn’t even technically be cheating. Not that my wife would ever find out. Letting a hooker fuck me up the ass with a hunk of plastic could not be considered cheating, right? My wife might disagree, but these days we disagreed about most things.

The phone was answered and I managed not to hang up. The woman, Jamie, had a deep, husky voice. For a moment, she sounded like a man, so I asked if it was her photo online. She admitted it was, and those were definitely female breasts, so I swallowed hard and made an appointment.
Jamie smiled and I nearly sagged in relief. No Adam’s apple. She had nice, average-sized breasts tucked into a white tank top. No bra. She wore a plain, khaki-colored skirt and sandals. No slutty hooker attire. Her hair was blonde.

In her hand, she held a large bag. My eyes flicked to it as I invited her in. She smiled again.

“I’m Ken,” I said. I handed her the cash, as instructed on the phone, and she tucked it away into the bag after unzipping it.

“Why don’t you get undressed and get on the bed?” she said throatily.

“Er… just like that?” I asked.

“I’m not paid for foreplay, darling.” She yanked off her top and kicked off the sandals. After shimmying out of the skirt, she pulled the dildo out of the bag—the same one in the photo still on the laptop.

I undressed quickly with shaking fingers while I watched her strap it on. My erection was already standing at attention.

“On the bed, Ken,” Jamie said in a voice that brooked no argument. I lay back on the bed and Jamie sauntered over. She looked down at me and laughed.

“You’re a pretty little bitch, aren’t you, Ken?” she asked. I tried to answer, but the saliva had dried up in my mouth. “Turn over,” she snapped. I did so. “Now spread your legs.” I complied. “Wider. Wider.”

I spread them until my hips creaked in protest. I felt humiliated, but also incredibly turned on. My cock rubbed on the bedspread with every movement. Jamie’s hand touched my ass, and then her cool fingers slid down and caressed my balls. I gasped and felt a trickle of wetness ooze from my stiff cock.

“You want it, don’t you, Kenny? You want me to fuck you hard, don’t you, little slut?”

“Yes,” I whispered and moaned. I opened my legs even wider, wanting her to move her hand down a bit and take my cock. She climbed onto the bed and moved her hand from my testicles, not down, but up to my anus. I jerked at the sensation. My wife had not touched me there, even accidentally, in all the years we’d been married.

Jamie’s fingers disappeared for a moment, and then returned, cold and slick with something. A finger swirled the lubricant around my quivering hole and my cock felt so hard I could probably come just by shifting slightly. I tried not to move.

Jamie suddenly pushed a finger inside and I arched and tensed. I thought I’d been ready, but the experience wasn’t as pleasant as I’d expected.

“Relax, Kenny, I have to stretch you out a bit before I can put my big cock in there.”

I tried to relax. After a moment, she added another finger. I moaned slightly, and then she curled her fingers slightly, and touched something inside that sent a fucking jolt of pure pleasure through me.

Jamie chuckled and withdrew her fingers. I felt something else, wide, hard, and slick with lube take their place. I tensed, thinking there was no way in hell I could stretch that wide, but Jamie’s hands rubbed my ass.

“It’s okay, Kenny, you can take me. You can take all of me, and then I’m going to fuck you right into the mattress. You want me to fuck you hard, don’t you, Kenny?”

I relaxed as the words shivered over me. Jamie pushed further, until I was gasping and sweating. I whimpered and nearly asked her to stop. Her knees prevented my thighs from closing. Jamie rammed into me suddenly, and I cried out. My fists partially tore the blankets from the bed. The strange pressure and pain was nearly unbearable.

Jamie slid nearly out, thank god, and then pushed forward again. The electric jolt came again, overwhelming the discomfort. Holy shit, that was interesting.

“Like that?” Jamie asked seductively. I nodded, unable to form a coherent response. She moved out and rocked forward again. I nearly writhed from the awesome feel of it. Jamie began to move in a smooth rhythm, pushing harder and deeper with every stroke. Her fingers dug into my hips and she pulled me into her thrusts. I could feel my orgasm building like nothing I’d ever felt—and then I came hard enough to see stars.

Jamie’s smooth hands patted my ass and then caressed my hips lightly.

“You’re a natural bottom, Kenny,” she said and I moaned as she pulled out completely. “You dream about big cocks, don’t you?”

I buried my face in the pillow, almost horrified by how much I had enjoyed being fucked, and shocked at the wave of lust that rushed over me at the thought of a real cock penetrating me.

Jamie climbed off the bed and went into the bathroom. I rolled over, wincing at the number of twinges I felt in places I did not know could twinge. I would be walking like a bowlegged cowboy tomorrow, if I could walk at all. My thighs were trembling with reaction.

I grimaced at the huge wet spot on the bed, knowing I’d have to call housekeeping to change the bedding.

Jamie came out of the bathroom, put away her dildo, and began to dress. She looked at me speculatively.

“You know, Ken, since you seem to be, shall we say… curious… I want to do you a favor.”

I wondered how much a “favor” from Jamie would cost me. She seemed to sense the question and smiled.

“My treat. Or actually, your treat.”

She flipped open her phone and dialed.

“Rolf, will you come up here for a bit? I have someone you might like to meet.”

She shut the phone and looked at me as I reached for my clothes.

“No, don’t dress,” she said in that authoritative tone. “You can clean yourself up, but come back and sit on the bed.”

I obediently went into the bathroom and cleaned myself up with a washcloth before returning. I had just seated myself when Jamie opened the door to admit a tall blond man. His eyes shot to me immediately and I flushed with embarrassment.

"Ken, this is my driver, Rolf,” Jamie said. “Rolf, this sweet little bit of flesh is Kenny. He’s experimenting and I thought he might want a taste of real cock.”

Rolf strode forward and I noticed his eyes were very intense and blue. He reached a hand out and touched the side of my jaw. Fuck, I felt myself growing hard. What the hell? I wasn’t gay! I was married, for fuck’s sake.

“I’ll leave you two alone,” Jamie said in an amused tone. I didn’t hear the door shut, because Rolf said, “Unzip my pants.”
I swallowed, but reached up shaking hands to unfasten his jeans, fumbling with the button a bit before sliding the zipper down. I could see Rolf’s bulge straining against his underwear.

“Take them off,” Rolf said and I pulled the jeans over his hips. He kicked off his shoes and stepped out of the denim. He wore boxer briefs and the blue t-shirt he wore barely brushed the waistband. There did not seem to be an ounce of fat on his body, but I hardly noticed that when he said, “Take it out.”

I swallowed hard and pulled the waistband down until the head of his hard cock was exposed. Oh god. My own erection was back and I glanced up to see Rolf smile as he said, “Touch it.”

I slipped a hand over Rolf’s cock, admiring the similarities and differences to my own. His was longer, I thought, and perhaps a bit broader. I pulled the briefs away with my left hand and grasped the velvety shaft with my right.

“Put it in your mouth,” Rolf said hoarsely and I leaned forward to let the hardness slide over my lips. He gasped when I took it completely and I felt his hand touch the top of my head gently. “You know what to do.”

I thought back to the random blowjobs I’d had and tried to recall what felt good. I took his cock as deep as I could, trying to suppress the gag reflex. I loved the feel of it against my tongue and I sucked lightly as I pulled back. I moved my tongue over the head in a swirling motion.

Rolf moaned and I felt a rush of erotic delight. I did it again and dipped the tip of my tongue into the slit, several times. Rolf jerked and I enveloped him again. I settled into a rhythm, pump, pump, pump, suck and swirl, over and over. Rolf was groaning and both hands were twisted in my hair. He was visibly trying to control the need to fuck my mouth, and I kept my left hand on his hip to keep him from choking me. My other hand pumped my own cock and when Rolf shot his hot load into my mouth, I came also, spurting over my hand. I gagged a bit at the taste, but swallowed quickly and sucked Rolf clean, knowing I would appreciate the same.

His eyes were a bit unfocused and I grinned up at him. His hands were still in my hair and he bent down and placed a kiss on my lips, dipping his tongue in to taste mine for a moment. I sucked in a surprised breath.

“How long will you be in town, Kenny?” he asked.

“Two more days.”

“Maybe I’ll drop by tomorrow night. Would you like that?”

Fuck, yes.
Jamie promised to be right over. Three hundred dollars. That wasn’t so bad. Not great, but not bad. I paced the room like a nervous wreck until a knock sounded on the door.