So. That Happened.

Contains male-on-male sex

My phone rang as I emerged from the subway. "This is Justin."

"Hey, Justin, this is Jim." The voice on the phone had a thick Texan accent.

"Hey, Jim. Thanks for calling." I ducked down a sidestreet to avoid the noise of the traffic.

"So I've been tasked with finding another gentleman to join my wife and me this evening." I smirked at his use of 'gentleman'. "Can you tell me a little about yourself?"

"Sure!" I said and ran the well-practiced lines that bore absolutely no resemblance to my real life.

"Well, you sound like a fine young man." I half-smiled again. I could think of two things wrong with that statement. "We're staying at The Standard hotel. Pam and I would love for you to meet us at the bar at, say, eleven o'clock?"

"Sounds great, Jim. Looking forward to it."

Jim had already mentioned he was staying at The Standard in an email earlier that evening, and I had already taken a train downtown. I was only blocks away from the hotel when he called. But I had half an hour to kill, so I stepped into the first bar I encountered and ordered a bourbon. Then I ordered a second, expecting that I would need it. Jim had mentioned that they were an older couple; 10 to 15 years older than me, and 20 to 25 years older than the age I claimed to be and could usually get away with. No doubt that was the appeal for them.

Jim had sent a picture of Pam. Her body, at least. She seemed to be in great shape for someone in her fifties; petite with a slim waist, and breasts that had obviously benefitted from some cosmetic work. In the picture she wore a sheer white top with no bra, hard nipples clearly outlined beneath the fabric. Jim didn't (or wouldn't) send a picture of himself, which raised a flag, but Pam's picture was enough to seal the deal for me. And, as usual, I was desperate for group sex.

I glanced at my watch. If I took my time, I'd make it to The Standard at around eleven. I pulled up Pam's picture on my phone one last time to steel myself, and left.

The Standard's bar was very quiet, but then again it was a Monday night. I scanned the thin crowd for a couple that included a woman who looked like Pam. They weren't hard to find, sitting at a high-top table near the bar.

"Jim? Pam?" I inquired.

"Yes!" They smiled.

"I'm Justin. Nice to meet you."

Pam was indeed an attractive woman in her late forties or early fifties. I couldn't help but think of that crude but apt acronym; MILF. Petite and blond, she wore a short white dress and a low-cut black cardigan that accentuated her impressive bust. Her legs were encased in opaque white stockings, and on her feet she wore white toe-peep shoes with conical spike heels. Even in heels, she was still only five and change.

Unsurprisingly, Jim was disappointing. He was a grey-haired, heavyset man in his fifties with a soft, but friendly face. He was tall, at least six foot, and wore a cheap suit. Oh well, I thought. I'd come this far.

We talked obligatory small talk over drinks that Jim paid for. They were from Dallas; he was in town on business, she was along for the ride. Whenever they visited the city, they liked to get a steak, see a show, and invite a young New York City boy back to their room.

"Well, we'd both love it if you could join us tonight," drawled Jim. "We just need to prepare first. How 'bout you meet us in our room in ten minutes?"

"Absolutely," I agreed. "See you shortly."

Jim gave me their room number, and I watched Pam totter away on her heels toward the elevators. She turned her head, caught my gaze, and gave me a wink and smile. I ordered another drink to pass the time and wondered what their preparations might entail.

Ten minutes passed. I downed my drink, settled my bill, and headed for the elevators myself. Stopping at the fifth floor, I located their room and knocked. Jim opened the door, greeting me in a hotel robe, and invited me into the dim room.

The king-sized bed was to my right. Pam was lying face down across the bed, naked, except for her stockings and her spike-heel peep-toes. Her head and arms hung over the mattress and she seemed to be restrained somehow at the wrist. After letting me in, Jim stepped around the bed and continued fastening a ball gag around her head. Huh. That's interesting, I thought. He gestured to the chair at the end of the bed. "Get naked and take a seat, Justin," he said. Jim's demeanor had changed, seeming less friendly and more ... domineering?

I walked to the end of the bed and kicked off my loafers and socks. I pulled my shirt out of my trousers, unbuttoned it, and slipped it off my arms before draping it over the back of the chair. Naked from the waist up, I glanced across the bed to see if either of them was enjoying the show, but Pam was still facing the floor and Jim was focused intently on securing the gag.

Shrugging, I pulled off my belt and lowered my zipper, letting my trousers fall to the floor around my ankles. Now completely naked, I stepped out of them, and tossed them on top my shirt over the back of the chair. I sat as Jim instructed. My cock began to harden as I admired Pam's body, her pale skin and white stockings almost incandescent in the dim light.

Jim finished lodging the ball gag firmly in Pam's mouth and untied the belt of his robe. He slipped the robe off his shoulders, revealing a doughy middle-aged man's body. He too was naked, except for a studded black leather cock ring fastened tight beneath the balls of a laughably small penis. This is only getting better, I thought to myself.

Jim's cock was only a few inches long and I couldn't tell if it was hard or soft. A micropenis is a tragic thing, but he seemed to have a kink in place to compensate for it. I hoped that it worked for him.

He retrieved a condom from a box on the nightstand, before walking towards me, opening and discarding the wrapper on the floor. He knelt in front of me and I opened my legs in anticipation. With lifeless eyes, he wordlessly rolled the condom down my eight inch shaft. Cupping my smooth balls in one hand, he lowered his mouth to my cock.

Jim's blowjob was dry, rough, and mechanical, and seemed, ironically, all about him. When Jim was in the Big City, he wanted to suck cock, so sucking cock was what he was going to do. I could respect that. Pam had turned her head and watched from the bed, making indistinct noises muffled by the gag.

Jim stopped and stood. "Go ahead and fuck Pam from behind," he instructed. I stood and stepped over to the bed. Pam pushed herself on to her knees, her butt in the air and her chest still flat against the bed. I knelt between her calves, placed my hands on her round buttocks, and spread them to expose a tight little asshole above small, puffy labia, now slick with wetness.

Jim again stood by Pam's head and removed her gag. She gasped for breath, then craned her neck and began tonguing Jim's ludicrous cock. "Yes, Daddy. Thank you, Daddy," she whispered in a squeaky little-girl voice. This was getting weird.

I effortlessly slid my cock into Pam's wet cunt. I took hold of her spike heels in my fists, and soon found a rhythm. I began fucking her vigorously, my pelvis slapping audibly against her ass. "Daddy! He's fucking me, Daddy! ... Daddy!" she squealed.

"I can see, baby girl. I can see," said Jim flatly.

I continued to fuck her as she easily accommodated Jim's tiny member between her lips. I wondered if it even reached the back of her mouth. Jim raised his eyes from her ministrations and looked directly at me. "Do you want to fuck me in the ass, Justin?"

I took a look at this ordinary, middle-aged man standing naked by the bed. I shrugged imperceptibly. It was something else to fuck and I was horny. "Whatever you want ... Daddy," I replied.

It was if an electric charge ran through Pam, and she writhed ecstatically in response to this magic word. "MMMmmmlolololommm!!" she moaned, her mouth still engulfing Jim's cock. Jim inclined his head, indicating that I should join him. I pulled out of Pam, then Jim released her restraints and helped her to flip over on the bed. She laid on her back, feet close together, but knees wide apart. Her legs formed a diamond shape, brazenly exposing her shaven pussy. Her silicone breasts sat unnaturally high and large on her chest, red-brown nipples engorged.

Jim bent at the knees and waist, lowering his small penis to Pam's willing mouth. Reaching again for the nightstand, he handed me a small bottle of lube. I smeared a little on my cock, then applied some more to my fingertips before gingerly, and with some distaste, reaching between his doughy buttocks. It was a strange dissonance; Jim couldn't have been further from my type, but I couldn't be more turned on by the situation; meeting and fucking these strangers ... who could not be stranger.

I bent my knees to position my cock between his buttocks, then slowly worked my glans inside him. He seemed unfazed by this, staring down at Pam as she continued to mouth his cock. I straightened my knees and pushed into him. "Ungh!" he grunted, as I penetrated another inch or two. After a number of slow, measured, movements in and out, I began to fuck him with relative ease. When a guy like me is horny enough, he will stick his dick in anything: from a tube sock, to an apple pie, to a middle-aged man's asshole. I reached around his hairy chest to his nipples, and began to pinch them with my fingertips.

"Do you like that, Daddy?"

"MMMmmmlolololommm!!" from Pam.

"Yesss," rasped Jim. "When you're ready, I want you to cum on Pam's tits."

Okay, I thought, happy to get this over with. I peered over Jim's shoulder and focused on his sexy wife; her unnaturally large breasts; her smooth pussy with the small, puffy, still-wet labia; her skinny legs encased in white nylon; and her slutty, toe-peep heels. She got me there. I pulled out of Jim and ripped off the condom from the base, flinging it to the floor. Standing at the end of the bed, I furiously pumped my cock in my fist until I emptied myself with a loud groan. Long strands of milky stickiness shot across her chest, breasts, and one artfully across a red-brown nipple.

Pam released Jim's cock from her mouth. "Daddy, Daddy, he made a mess all over me!"

"Oh, yes, baby girl. Yes, he did. Let Daddy clean all this up."

Jim clambered on to the bed to the other side of Pam. On his elbows and knees, he lowered his head to her tits and started lapping at my freshly expelled semen, scooping up thick, white wads with his tongue and swallowing them down. With her head arched back, and her eyes closed, Pam squirmed and moaned. "Thank you, Daddy ... thank you, Daddy ... thank you, Daddy ..."

I shrugged and began to dress. Whatever turns you on, I thought. As I left the room, the couple were in each other's arms on the bed, sharing a deep kiss, no doubt lubricated with my cum.

"Thank you, Justin," said Jim from the bed.

No, thank you," I replied, closing the door behind me.

Well, that was weird, I thought. I checked off the mature, light bondage, cuckold, and incest fantasy categories from a mental list. As I left the hotel, I hoped they had got what they wanted. I certainly had, I thought, my empty balls aching.