Weeks after their initial meeting, Joe spent trying to locate Craig, hanging out at the bar they met, sliding his phone number under his apartment door (which he knew was creepy), and walking about hoping for a chance encounter. He frequently berated himself for being so careless to not get Craig’s contact information. He had several sex dreams about Craig, a constant reminder of infatuation. Discouraged, Joe decided to continue with his life with the hopes that one day he would run across Craig again. On a Friday night Joe headed to a bar where hook ups were the norm. A frustrating week at work, and the inability to locate Craig had Joe wanting some action.
Upon entering the bar Joe ordered his beer, and while scanning the crowded room noticed a large Black man similar in shape to Craig’s. He was with a man, appearing to have a casual conversation with him. Not convinced it was Craig, Joe moved where he could get a better look, trying to be as discrete as possible considering that the man of his dreams may have already hooked up. Before he could get into a strategic position, Joe saw the two men kissing, then returning to their conversation. The place was crowded enough so that Joe would go unnoticed across the room. It was indeed Craig that Joe was looking at. Deep disappointment set in. Joe was crushed that Craig was with another man, believing that he may have lost any opportunity to get back with him. Finishing his drink, he got up to walk out of the bar when he locked eyes with Craig, who looked surprised. Joe froze in his tracks, waiting a further response from the big man.
To Joe’s surprise, and bewilderment, Craig waved Joe over to the table where the two sat. Once there, Joe was warmly introduced to John, another middle aged white man. “Hey man, good seeing you again. This is my friend John,” said Craig, placing his hand on Joe’s back.
With a strong handshake, John appeared to be very masculine and friendly. “Nice to meet you---,” said John, looking Craig’s direction for a name.
The look on Craig’s face indicated that he was unaware of Joe’s name. “Man, I am sorry. Jay?” said Craig.
While disappointed, Joe understood that they had only spent one drunken, high night together. “Joe. Name’s Joe,” he said, still feeling the firmness of John’s hand.
“Well nice to meet you Joe,” said John, releasing his hand. “Can I get you drink? I’m about to get a refill.”
“No, but thanks for offering,” said Joe, looking forward to having a few minutes alone with Craig to scope out the relationship situation, if there was one. “Hey, I tried getting in touch with you, was hoping we could get together again.”
“Yeh man, been working a lot. Plus I didn’t know how to get in touch,” said Craig, guzzling his beer.
“I left a note under your door. Hope you didn’t think that was creepy,” said Joe, admiring Craig’s strong, wide, round facial features.
“Oh so that was you. Well it didn’t have a name on it and, obviously, I didn’t remember your name. Man I’m sorry,” said Craig, looking at Joe with sincerity.
“No problem. So who’s John?” asked Joe, getting right to the point knowing John would soon be returning.
“John’s cool people. We meet up now and then,” said Craig, appearing a bit put off by Joe’s questioning. “Why you ask?”
“I’ll be totally honest with you. I’ve been thinking about you and looking for you. When I saw you here kissing another man I assumed what we had was a one night fling,” said Joe. He pulled out a business card that had his cell on it and slid it to Craig. “I’d love to keep in touch.”
The look on Craig’s face said it all, disappointment and confusion. “Man, we were fucked up. I just remember having some bomb ass sex and waking up hung over and alone. Shit, I didn’t even remember your name.” Craig often experienced men who wanted to spend more time with him after a night of sex. But it was always just sex, nothing more. It appeared as if Joe was no different. John and Craig were fuck buddies, with neither one interested in pursuing a long term relationship with one another. But they had that understanding and Craig didn’t want to have any drama in his life.
Joe knew he had upset Craig but could not explain since John soon returned with a drink in hand. “You two getting along?” he asked as he sat.
“Yeh man, we cool,” said Craig, not giving any indication of what had just transpired. For the next thirty minutes or so the three engaged mostly in small talk. Joe noticed that his business card was gone, hoping it was Craig that picked it up and not a jealous lover.
After John finished his drink Craig stated it was time to go. The two got up together and put on their coats. “Well Joe, it was nice meeting you,” said John.
“Same here man,” said Joe, trying to hide his letdown.
While John appeared to not spot it, Craig knew Joe was saddened. On his way out, he grabbed Joe gently by the neck, gently massaging it, as If to say “tough luck man.”
John was a wealthy attorney who lived in a studio loft apartment in Manhattan’s east side. After being divorced for many years he was living out his fantasy of being servile to a Black man. By now the doorman knew the relationship between Craig and John so was used to seeing them together. Upon entering the apartment John, removed his clothes and outfitted himself in Craig’s favorite attire, black panties, garters and a sheer teddy.
While in the bathroom looking in the mirror, putting on his blonde wig and make up, he saw Craig come up behind him, feeling his hands caress his ass and his lips on his neck. “Damn bitch, you are looking fine,” said Craig, kissing John’s shoulders.
“Glad you like,” said John as he continued to make himself up to Craig’s liking, applying bright red lipstick. “So who was that man you introduced me to tonight?”
“Some dude I fucked because you weren’t around last weekend,” said Craig, moving his kisses to John’s neck.
“Hmmmmmm. Well you know I had the kids,” said John, putting the finishing touches on his face. “I’ve been thinking. Maybe we should consider some type of arrangement. Nothing permanent, just some regular time together instead of chance hook ups at bars,” said John, turning to face Craig. “I mean with all the shit going around. And I know you aren’t going to wear a rubber,” said John, turning around to finish his make-up.
“We’ll discuss this later. Right now I want to see those pretty lips wrapped around my cock,” said Craig, unzipping his pants and pulling out his semi-hard dick. Although John wanted to continue the discussion, meeting the needs of Craig was always priority.
“Mmmmm, anything for Daddy,” said John as he turned back around and knelt before Craig, slowly taking him into his mouth. The look of John’s red lips stroking his dick and the feel of his tongue around him provided immense pleasure to Craig. Before he met John he had never been into cross dressers but there was something about the power he had to make a white man into a sex crazed woman that turned him on. Craig pulled out his fully engorged dick, slapping John’s face, leaving a trail of saliva as he slowly pulled away. “Undress Daddy,” said Craig holding out arms. As John removed each article of clothing he kissed and licked the bared flesh until he was completely naked. Craig walked away, his hard pole swinging in rhythm with the big man’s swag. From a nearby floor chest Craig got out a leather collar and leash, returning to the man on his knees to fasten them. He yanked up on the leash suddenly, and pulled John to the couch, making him crawl faster than he could on the hard wood floor.
John loved the aggression from Craig but tonight it seemed excessive. “Get my belt,” demanded Craig. “I’m going to spank the hell out of that pert white ass before fucking it.” Though not unusual to get paddled, the tone of Craig’s voice expressed anger and a belt was usually not the choice of punishment.
“I hope I have not made Daddy mad,” said John, massaging Craig’s huge, hairy thighs. “Can I make it up to you?”
“Just get the fucking belt,” said Craig, becoming increasingly annoyed with John’s questioning. John hesitated before obeying Craig. He enjoyed the rough treatment but it was usually part of a sexual situation where punishment was pleasurable. This seemed more like Craig was intent on hurting him for something he was unaware. After sheepishly handing Craig the belt, Craig snatched John onto his lap, pulling down the panties and delivering several whacks to his behind. Knowing better than to resist, John grimaced and quietly endured the pain. Once finished, John awaited Craig’s next move while feeling the sting slowly ease. He knew of Craig’s sudden mood swings but never did they result in what he had just experienced. He felt Craig’s hard dick under him and needed no prompts to kneel before him and take him into his mouth. Craig was so excited that he blew his load into John’s talented mouth in a matter of minutes, which John eagerly swallowed. As usually was the case with Craig, the next few hours were spent fucking John and spilling his seed inside of him. Waking up next to a dolled up man excited Craig for another round of sexual submission that John offered so well. In the usual sleeping position, Craig spooned Joe, providing easy access anytime he felt the need. He lifted the sheer teddy, revealing a lightly bruised white ass. Spreading his cheeks showed a red, well stretched rosebud that was still moist from a mixture of saliva, lube and sperm which instantly excited Craig. Rubbing his fully erect penis around the well used hole awoke John, eliciting a slight moan, surrendering to the warm, hard probing flesh. Craig slid easily in, enjoying the familiar warmth moisture that excited him so much. John reached behind him, embracing the thick neck of the man, pushing his ass onto the pole that was slowly entering him, showing how much he wanted it. The smooth feel of John’s asshole, sheer negligee against his chest, the blonde hair in his face, and now the back thrust that further inserted himself in his willing ass resulted in Craig delivering a quick, hard push to feel the entire length of his dick surrounded. The two simultaneously moaned, locked into position.
“Fuck bitch you got a hot ass,” said Craig as he stayed fully inserted for a few minutes while he reached around and rubbed John’s nipples until they hardened, then pinching hard while beginning to stroke, then pounding repeatedly. Without pulling out, he put John in doggy, riding him hard causing the bed to shake violently.
John loved the aggressive fucking of Craig, showing he had stamina and strength to keep his ass up and still the way he knew the big man liked it. Having already experienced orgasms, John and Craig fucked for a good while. After delivering another load while John was on top, the two lie motionless, embraced in each other’s arms until they caught their breaths.
“Fix you breakfast babe?” asked John kissing Craig’s lips.
“Do you need to ask?” said Craig, returning his kisses.
“I’ll get right to it,” said John as he dismounted, admiring the sight of the long, thick black dick that lie to the side of Craig’s hairy crotch. John brought Craig his breakfast in bed, resting his head on his furry chest while he ate.
“You’re not hungry?” asked Craig as he ate.
“No, I’m good. Have everything I need right here,” said John as he took a nipple into his mouth.
“Sorry bitch, those titties won’t feed you,” said Craig jokingly. The rest of the day was spent with John serving his king, bathing him, and making sure he had all his needs met before Craig had to leave.
Determined to enjoy the evening, despite the let down of watching Craig walk away with another man, Joe was on the hunt to get laid. Being no stranger to the cruising scene, Joe’s usual strategy to wait it out until the most desirable bearish, man of color appeared, normally worked. But it was near closing time and everyone was either coupled up, or not to his liking. That night, with legs up in the air, 8 inch dildo working his ass, with the image of Craig on top of him resulted in a stream of sperm covering his chest and belly. Satisfied enough to fall asleep, Joe’s sex dreams occupied much of the time until he woke up, prompting him to stroke out another load thinking about the man of his dreams. The mad lust he felt for Craig consumed him. He felt more determined than ever to get another chance.