LwL: Harry Goes Cruising

(This one is a bit different, and i hope you think it has some entertaining twists. Not going to lie, this was fun to write)

(Also, you may have noticed that I've stopped recapping previous stories. This is mostly because the stories have become a bit more episodic, and the last few can be read in any order. If you haven't read the others, suffice it to say that this is about the adventures of a bisexual couple - one member with a lot of experience, the other a newbie - and their various friends/ lovers)

The DJ was spinning "Groove Is In The Heart" as several men dressed in different neon shades gyrated on the dance floor. They ranged from men in their 20s experiencing second-hand nostalgia to men in their 50s attempting to recapture their youth. Harry sat at the bar, dressed in a polo shirt and jeans, nursing a gin and tonic.

"If I knew it was 90s Night I would have dressed more appropriately," said Harry over the thumping bass. The bartender, a stout man with a shaved head and a goatee, laughed.

"Don't feel too bad, most of the time we get more guys dressed like you." Harry wasn't sure if the bartender was trying to comfort him or insult him.

According to the travel website Harry consulted, Alexander's was one of Carter Hills's first gay bars, with "a bit of a lower-key atmosphere than some of the flashier nightclubs, and attracting a slightly older clientele." As someone with little experience in gay clubs, Harry thought it a good place to start, especially as he was in an unfamiliar city.

Harry had some business in Carter Hills, so he and Joan had decided to make a vacation of it, especially since this was an opportunity for Joan to meet up with Marcy. Joan was doing just that right now, so she suggested Harry try some cruising.

"What would it hurt? Just make sure to tell me the details afterwards."

Harry's emotions were cycling between excitement and fear. Even when he was single he had never been partial to anonymous sex, least of all with men. Back then if he couldn't get a date he was more likely to just go home and watch some porn.

From the middle of the crowd came a figure in a red minidress with a yellow daisy pattern. Dayglo rubber bracelets jiggled from her bare arms. A purple-and-orange Dr Seuss hat topped her blonde bob.

"Hey Becks, what'll you have?" asked the bartenders.

"Just a soda with lemon for now, I'm feeling pretty hot." The figure sat down on a stool next to Harry and twirled around.

"Hello, I'm Rebecca," she said, offering her hand to Harry. Judging by the dilated pupils Rebecca was on something a bit stronger than alcohol.

"Harry."

"Good to meet you, Harry."

Even in an intoxicated state Rebecca was quite striking. Rail-thin, she resembled a 1960s fashion model as interpreted by 1990s club culture. Harry couldn't tell for sure whether she felt under the older or younger ends of the bar's demographic. Her makeup, accented by red lipstick and false eyelashes, was smudged but still effective. Only her voice - a baritone masked by a smoky drawl - gave her away.

"I haven't seen you around, Harry, are you new in town?"

"Just visiting from River City."

"Maybe I can show you around."

"That would be nice."

The DJ put on "Strike it Up" by Black Box and Rebecca jumped out of her seat.

"I love this song! Cmon Harry, let's dance!" She clearly wouldn't take no for an answer, grabbing Harry by the hand and leading him to the dancefloor. Harry gamely attempted some moves while Rebecca ground her taut ass into his crotch, putting her arms around him and swaying to the beat. Harry found himself getting hard. He'd never been with someone like Rebecca, and she was turning him on.

The next song was a slower, trippy dance track Harry didn't quite recognize. Rebecca turned around to face Harry, kissing him hard on the lips and grabbing Harry's ass with both hands. Harry felt his cock rub up against a bulge under Rebecca's dress. When Harry smiled, Rebecca smiled in turn, relieved that Harry wasn't upset.

They continued this slow grind as the DJ switched to a hip-hop track with a heavy, slow bassline. Harry was slightly concerned he might come right there on the dancefloor.

They were getting hot and heavy when a ringtone went off. Rebecca suddenly stopped and reached into her handbag and pulled out her phone.

"Hey, what's up," she said to whoever was on the other line. "What? Fuck. Okay, I'll be right there." Rebecca looked up at her dance partner. "Sorry, Harry, it's been nice but I gotta split." She gave him one last kiss and then ran out the door, trying not to trip on her chunky platforms.

Harry stood there for a moment, dumbfounded. He briefly considered finding someone else to dance with, then thought the better of it and went back to the bar. He gave the bartender an exasperated shrug. The bartender smiled.

"Don't sweat it, man, that's just Becks. She's a wildcat for sure." A waiter came up to the bar and whispered something to the bartender, gesturing over to a booth in the corner. The bartender nodded and quickly poured another gin and tonic and handed it to Harry.

"Complements of the gentlemen in the booth over there."

Harry looked around, slightly confused. He spied two men sitting in the booth. The first one, who had brown hair slicked back and a thin mustache, looked like he was dressed more for an 80s Night than 90s Night. He wore a black sport coat over a pale blue T-shirt. The other one, with black spiky hair, was wearing a plaid flannel shirt.

Harry walked over to them and smiled.

"Thanks, fellas."

"We saw you strike out and felt bad for you," said the one with the slicked back hair. "Have a seat. Name's Jim, this is Mickey."

Harry sat down across from the two.

"Do I know you? You two look familiar." Mickey smiled.

"Maybe, maybe not, but we'd like to get to know you better. You here on business?

"Partly, partly pleasure. How did you know I'm not from around here?"

"We know, trust us," said Jim, suppressing a laugh. Jim reached across the table and touched Harry's left hand, stroking his wedding ring. "Is your wife here with you?"

"Yeah," said Harry. He opened his wallet and showed them a picture of Joan."

"Mmm, pretty little thing," said Mickey, which earned a dirty look from Jim.

"She's visiting with a friend right now, so I'm on my own."

"She know you're here?"

"Maybe not this place exactly, but yeah. We have an understanding."

"Oh?" Mickey raised an eyebrow.

"As long as I play safe and tell her about it, we're cool."

"I think I know how that goes," said Jimmy, flashing his own wedding ring.

"So do you live around here?"

"Damn, Harry," said Mickey, "you're not one for small talk, are you?"

"Usually I'm fine with just talking, but Rebecca got me a little hot and bothered."

"So, What do you have in mind?"

"Anything, really."

"Well, Jimmy here is also from out of town," said Mickey. "We could go to my place, but it's a pretty long cab ride."

"Hmm. I'm staying at the Marriott a few blocks away."

"You sure your wife won't mind?"

"I'm sure."

"Well, then let's mosey, cowboy," said Jim. As they got out of the booth Harry saw that Jimmy was about a head shorter than him, and Mickey was somewhere in between the two of them in height. Jimmy was thin and wiry, while Mickey had a bit of heft to him.

The three walked to the hotel and went up to Harry and Joan's room. They were the only ones in the elevator, and Jim took the opportunity to reach over and grope Harry's crotch.

"Calm down, Jimmy," said Mickey. "There's plenty of time for that."

They reached the suite and Harry used the keycard to open the door. They took off their shoes and Harry offered Jim a hanger for his sport coat. As they sat on the bed, Jim made the first move, grabbing Harry by the neck and giving him a long, hard kiss. Mickey put his arms round them both and joined in the kiss, putting his tongue in Jimmy's mouth. Harry ripped off his shirt and began to undo his pants. Jimmy suddenly got up and went to turn off the lights.

"I like it better in the dark," said Jimmy. The room was now lit only by the skyline outside.

Harry was down to his underwear and his cock was already throbbing. Harry heard a couple of soft clicks as Jim and Mickey met him on the bed, both very hard. Harry had been with a few men and was not particularly self-conscious about the size of his endowment, but he was slightly taken aback that both Jim and Mickey seemed to be larger than him in that department. Still, Harry had grown to really like frotting, and he dove lustily to greet his new lovers, stroking all three in his hand.

"Oh fuck, this is nice," said Mickey, kissing Harry on the neck. Harry felt a hand on his cock, and looked down. Through the shadows he could make out Jimmy stroking the shaft and cupping his balls. Harry grabbed Jim's perfect ass and gave it a squeeze. For some reason Mickey and Jim had left their shirts on, but that didn't matter to Harry, who concentrated on their cocks and asses.

Jim reached over to the nightstand and picked up a pack of condoms. Continuing to kiss Mickey and Harry, he slipped on one of the condoms and handed one to both of his lovers. They then spent a few minutes lubing Mickey and Harry's asses.

They arranged themselves with Jimmy in back, Mickey in the middle and Harry at the front. Jim entered Mickey and in turn Mickey entered Harry. Harry gasped a little as this was probably the biggest cock he'd ever had in his ass.

"Oh my," said Harry.

"You like that, huh?" said Mickey, giving Harry a thrust and grabbing his cock. "Yeah, you like that." Mickey used Harry's cock like a joystick to maneuver himself further into Harry's ass.

The three began the chaotic process of timing their thrusts, laughing as they fumbled around a few times before establishing a rhythm. Harry had been with a few men before, and his experiences had ranged from passionate, tender lovemaking to raw, savage fucking. So far, tonight was more of the latter. Jim thrust into Mickey with pure power, and Mickey in turn thrust into Harry. Mickey reached over and stroked Harry with an almost frenetic pace, moaning as Jim kissed him on the back, and Mickey in turn licked Harry's ear.

"Oh fuck," said Harry as the other two moaned lustily.

Harry came first, gushing into the condom on his swollen cock. Mickey and Jim followed, and they spent a few minutes recharging, then switched positions. Harry wiped off his cock and got a fresh condom and entered Mickey's ass while Mickey lubed up Jim and entered him. Soon they were each having another orgasm.

"I think I need something to drink," said Harry. He got up, grabbed a glass from the table and walked over to the bathroom. As he was filling the glass at the sink he spied himself in the mirror and noticed a black smudge on his cheek. Rubbing it with his hand, he realized it was eyebrow pencil and laughed.

"Hey, honey, I think your moustache is coming off."

"What?" said Jim, turning on the light by the nightstand and looking at the mirror on the table. Sure enough, his moustache had started to smudge.

"Goddamn it! Well, at least it lasted most of the night. I guess the jig is up." Jim took off his shirt, revealing a small but well-shaped pair of breasts. Mickey removed his own shirt, showing he was wearing a harness binding his chest. Jim, now Joan, helped Mickey out of the harness, setting free a larger pair of breasts.

"God, this thing is uncomfortable, said Marcy.

"At least you've got a decent pair," said Joan, looking down at her own breasts.

"Eh, yours are just fine," said Marcy, flicking Joan's nipple piercings.

"Tell me seriously, Harry," asked Joan, "how were we?"

"Fucking awesome, as always."

"No, I mean how were we as guys? Did we do a convincing job?"

"Yeah, I mean I'm not the one to say for sure because I knew it was you. But you both make for a pair of sexy men."

"You're a sweetheart, Harry," said Marcy as she got up to get herself some water. "I'm so glad I finally got to peg you." Marcy had always identified as a lesbian, but she was very fond of Harry and had always said if she ever fooled around with a man, it would have to be him.

Like Joan, Marcy had removed her binders, revealing her large, soft breasts. She had also taken off the harness for the strap-on.

"Anybody up for some more?" asked Marcy.

"Yeah, give me a sec," said Harry as he headed back towards the bed. He leaned over and kissed his wife.

"I'm ready, too," said Joan, replacing the condom on her strap-on." "But I'm not getting rid of this."

They convened on the bed, hugging and groping each other. Harry and Marcy concentrated on licking and kissing Joan's breasts, as she geared up to fuck Harry. Marcy surprised Harry by asking him to lick her pussy.

"Are you sure?"

"Yeah. Why not? I've never had a guy down there but it's worth a try."

Harry took it slow and steady, doing his best to make Marcy come. As Harry was eating out Marcy, Joan entered Harry again from behind, stroking his cock while she thrust into him. Joan had never been a shrinking violet, but Harry had noticed that when she took on the more dominant role she became very aggressive and yet at the same time playful. The combination of pressure on his prostate and attention to his cock quickly brought Harry to another climax.

Harry didn't let his orgasm deter his efforts with Marcy. He continued to probe her labia with long, loving strokes of his tongue. Marcy was clearly responding, but she didn't seem close to coming. Joan nudged Harry and gave him a look as if to say "here, let me try."

Joan's skills seemed to do to the trick, and sure enough, Marcy was soon coming in a shuddering, full-bodied orgasm.

As she was coming back down to Earth, Marcy brought Joan in for a kiss, savouring her own juices on the other woman's lips. She then looked at Harry.

"Don't feel discouraged, buddy," said Marcy. "You're one of the first men to try." She stood up and gave Harry a tiny peck on the cheek. "Cmon, I'll show you a few pointers."

Marcy grabbed Joan and gently pushed her onto the bed. She gestured for Harry to join her between Joan's legs.

Joan relished the attention from her two lovers. Marcy and Harry's tongues maneuvered every square inch of Joan's pussy, occasionally meeting for a short kiss. They eventually agreed on a system where Harry licked the folds of the vulva with a circular motion and Marcy concentrated on Joan's clit. This seemed to work, and soon Joan rewarded their efforts by coming in a gushing orgasm. Harry and Marcy stopped to kiss and share Joan's nectars, then moved up to share them with the woman herself. Joan wrapped her arms around them both, relishing the love of her man and her oldest friend.

They slept in late, then decided to get ready for brunch at the hotel restaurant. Sipping her mimosa, Joan paused to ask her husband something that had been bothering her.

"So give it to me straight, hun," said Joan, "would you have gone after that girl if she hadn't left? Did she turn you on?"

"Oh absolutely," said Harry, "I've never really thought about being with someone like that, but she was something else. A little high and sweaty, but really hot."

"That's good to know, because I might know someone back home who we could meet up with."

"Mm that would be nice, but you know what? I'd rather see Jim again."

"That could definitely be arranged," said Joan with a wicked grin.