An Evening At Pearl's

This story was originally published for the HALLOWEEN 2026 Story Contest.

**********

An Evening At Pearl's

Everyone Dresses for Halloween

**********

Randall and Vivian had been dating for a few weeks. As planned, they had gone to Pearl's, the local queer bar, for their official first date. Now, weeks later, they sat on the bed in Vivian's apartment making plans to attend the Halloween party there. Even post-sex, Vivian was wearing her frilly underwear since she wasn't yet comfortable with Randall seeing her boy parts. Randall had no problem with being naked next to her, though. As they sat staring at Vivian's closet, it was clear that she didn't have a lot of costume options. Without any family support she could barely afford her apartment, let alone a wide variety of clothes.

Randall said, "Look, whatever our costumes are, yours should be something you can wear other times, too. I can just match you. Don't worry about that."

Vivian looked from Randall to her closet. "But... My clothes aren't costumes. They show what I am. What I want people to think when they see me."

"Yeah, I get it. But regular clothes can still work as a sexy costume." Randall stood up and pulled a red pleated skirt out. Holding it against his own naked hips, he said, "What about this? You only need an orange sweater and you've got a costume!"

"What costume?"

"Velma from Scooby-Doo! Yeah, maybe glasses and a magnifying glass would finish selling it, but it would work!"

Vivian jumped up and hugged Randall. "That sounds great! Who will you go as? Shaggy?"

Randall leaned over and kissed Vivian. "Maybe. That is an easy costume, too. Have you been to Kohler's recently? We could try there; that is where Hannah often gets clothes."

Vivian let her hand slip down to Randall's naked ass. "Are you asking to go shopping with me?"

Laughing, Randall said, "Not only am I asking to go shopping with you, but I'm offering to take you shopping. I'll buy the clothes. How does that sound?"

Vivian laughed, too. "Well, we will have to get dressed first."

With a deep sigh, Randall said, "That is a sacrifice I am willing to make." Then he grinned at Vivian before starting to get dressed.

Kohler's was busy, as always, but the store was pretty big, so it wasn't crowded. The young couple held hands as they browsed around, and for perhaps the first time in her adult life Vivian felt loved and supported. It only took a few minutes to settle on the best choice for her baggy turtleneck sweater.

Randall asked, "The orange isn't perfect, but it is pretty close, don't you think?"

Vivian smiled, "Just right. It's lovely!"

"Ok, you go try it on. I'll look for tights or long socks that match."

Inside the changing room, Vivian stripped off her shirt to reveal her lacy bra. She looked at herself briefly, and for the first time in a long time she was happy with what she saw. The bra was shaped by breast forms, sure, but she wouldn't need them forever. Even if she never got around to the drugs or surgery to have permanent breasts, Randall had shown her that she could be loved without them.

Vivian smiled as she pulled the sweater over her head and smoothed it down over her stomach. It looked good on her, and set off the red pleated skirt she was wearing just right.

Meanwhile, Randall had found long orange socks that matched the other sweaters still on the racks.

On the way back to the changing rooms, he walked past a display of scarves and stopped to look at them. There was a wide variety, mostly solid colors, but a few with patterns. He reached out and stroked a silky green scarf as a smile spread across his face. He pulled the scarf loose and hurried back to the dressing area with a grin.

He arrived just in time for Vivian to come out and show off the sweater. She spun around and asked, "So, what do you think?"

"Perfect! And these socks will make it even better!" Randall went to his knees next to Vivian, and he held the socks against a bare thigh. He let his hand brush against her soft, smooth skin as he said, "Lovely."

Vivian laughed at his flirtation but pointed at the green scarf. "What's that?"

Randall handed Vivian the orange socks as he stood up and threw the scarf around his neck. "I've decided against Shaggy. I'll need a red wig, though..."

Vivian stifled a giggle by covering her face and asked, "Would you really?"

"There is no better place for it than Pearl's, right?"

Vivian laughed as they hugged one another and walked toward the checkout line.

A few days later, Randall sat on the edge of Vivian's bed wearing the scarf, a red wig and a purple dress. Vivian knelt between his spread thighs, with her hands running up and down the white thigh-highs covering them. Her mouth was bobbing up and down on Randall's hard dick while she slobbered noisily. Randall had his hands tangled in her hair, but was only gently holding her. His hands followed her movements as he gazed down on her. Vivian, for her part, looked up into Randall's eyes.

"Oh, god, Vivian, I'm going to come!"

Vivian drove her face down onto Randall and started humming as she buried the head of his cock into the top of her throat. She tried to smile, but with a dick spreading her lips she couldn't quite manage. Randall saw the smile around her eyes as he blasted into her throat, though.

Once his body stopped thrusting into Vivian, Randall let himself fall back onto the bed with a sigh. Vivian crawled next to him and watched him breathe. After a moment, Randall opened his eyes and looked up at Vivian, who was smiling down at him.

"That was great, babe. Are you sure you don't want me to..."

Vivian shook her head. "No, not that. Just the other thing to get ready for later."

"Ok. As you wish." Randall stood up and smoothed his dress so that it fit better. It wasn't perfect; the dress was made for a woman's frame and they hadn't been able to adjust it. It still looked good enough, especially when standing next to Vivian's Velma.

Vivian had rolled onto her hands and knees, with her knees barely on the edge of the bed. Randall flipped her skirt up, revealing her panty-clad ass. Feeling his hands running over her ass caused Vivian to sigh in pleasure. Randall lowered her panties enough to reveal her boy-pussy, but left them covering everything else. He knew she was sensitive about him seeing the rest, even though they had been together several times over the previous few weeks.

Randall leaned down and kissed one of Vivian's ass cheeks before turning to the bedside table to pick up her pink butt plug. It was the larger of the two, but still smaller than Randall's dick. Holding it in his left hand, Randall squirted lube onto it and made sure it was well coated. The curved handle would fit between her cheeks to hold it in place for the evening, and nobody would ever guess that it was there. Randall started massaging her opening with his lubricated left hand to make sure that she was ready.

Vivian sighed again, causing Randall to ask, "Are you ready?"

"Yes, please. Put it into me."

Randall slowly inserted the butt plug, making certain to insert it little by little until Vivian relaxed enough that the whole thing slid into place. "Unhh," she said, "There it is."

Randall wiggled the grip up and down the crack of Vivian's ass to be certain that it was well seated. "How does that feel?"

"Good. Stretchy, but good."

Randall leaned down and kissed her ass again. "Great! Let me wash my hands and we can get ready to go!"

The streets around Pearl's were pretty busy, but it was late enough that there weren't many kids still trick-or-treating. If there were any still out, they were in the suburbs, not downtown. A steady trickle of people moved toward the bar, and music spilled out into the street every time the door opened.

There were two big burly guys standing outside the front door checking id's. One broad shouldered guy wore a blue and white checked dress that fell just beneath his knees. Long braided pigtails and shiny red sneakers finished his look. The second guy was dressed as a lion, with a large medal pinned to his chest. Neither Vivian nor Randall recognized the lion, but when he asked for their IDs, Randall pointed to Dorothy.

"Oh, we are friends of Dorothy. We've been here before."

Dorothy smiled at the couple and spread his arms wide. "Randall! Vivian! You both look great!"

Randall took the hug and squeezed Dorothy for all he was worth. He was out-squeezed, though, and Dorothy picked him up almost without trying. Dorothy put Randall down and also offered Vivian a hug. That offer was much more reserved; it was barely a spreading of his hands. He knew that Vivian wasn't comfortable in her body and didn't like hugs, but offered anyway. Vivian shook her head 'no,' so Dorothy opened the door and ushered them inside.

Pearl's had once been two separate establishments. The main serving area they entered was dominated by a large u-shaped bar in the middle that was surrounded by stools, with small tables between the bar and the booths that surrounded the walls. The place was busy, with almost every seat taken, and some people standing between chairs chatting with their seated friends. Almost everyone was in costume, although many were barely dressed. There were lots of guys wearing just a speedo and some accessory to identify their costume. There were even a few similarly dressed women wearing only enough to make them legal to walk around in public. Pearl's welcomed everyone, regardless of gender or sexual preference.

The music came from a set of double doors to the left that led to the dance floor, where more people were congregating. Vivian and Randall made their way there, passing a Shaggy who bobbed his head and said, "Hey, man! Nice to see you both out tonight!"

"Hey, Shaggy!" Randall waved as they walked past.

Vivian asked, "Do you know who that was?"

Randall shook his head. "No idea! But now I'm even more glad I didn't dress as Shaggy!"

There was another bar in the dance room; it stretched down the near wall, but there were no stools for it. People would approach the bar, wait to order a drink, and then move back across the dance floor. The center of the room was lit by lights flashing in time to the music. There were lots of people dancing, including a man and a woman, each dressed as Wonder Woman, who were dancing together and making out on the dance floor. Although nothing was visible, the woman was humping the man's bare thigh, their joining barely covered by their skirts. Vivian watched as the man held onto the woman while she shook through a public orgasm. Several other people watched as well. As one song faded into the next, they smiled at one another, hugged, and went to different groups.

Randall asked, "Do you think they know each other?"

Vivian shrugged, "Probably not. They wouldn't have both come dressed as the same character, right?"

Vivian and Randall watched the dance floor while waiting to order a drink. It was crowded with costumed people moving in time to the music. Many of them were just having a good time, but some were so into one another, like the two Wonder Woman characters, that they seemed to be having sex in the crowd. There were a number of men in full drag, looking like actresses on the red carpet. Marilyn Monroe, Jessica Rabbit, and Dolly Parton danced in a tight circle next to a foursome of Xena, Gabrielle and women dressed as Wayne and Garth.

As the couple moved around the outside of the dance floor, they passed a group of gyrating men dressed as mummies. They were almost naked and strategic spots were barely covered by tatters of bandages. One of the guys called out, "Randall!" who turned to see his friend Brayden.

Brayden spread his arms wide and moved to hug Randall, who returned the hug and kissed the mummy on the cheek. Brayden said, "I thought that was you! I'm surprised to see you here! That red wig is great!"

"Brayden! It's great to see you! I'm here with my friend, Vivian!" Randall turned and motioned her closer. "Vivian, this is my friend Brayden. The guy I told you about."

Brayden glanced at Randall, surprised that he seemed to have told his girlfriend about their weekend together. "Hi Vivian, it's nice to meet you." He offered her a hug as well, but she just stuck out her hand in response.

"It's nice to meet you, Brayden. Do you come here often?"

While shaking her hand briefly, Brayden shrugged, "Sometimes. But I always make it for the gay high holiday!" Brayden waved his hand at the crowd with a flourish and a smile. "Come on, let me introduce you to my friends!"

Brayden introduced Randall and Vivian to his mummy friends, and as the evening progressed, they met lots of other people. Shaggy came back to them and introduced himself and Scooby, too. She was a tall brunette wearing a furry brown bikini, fake floppy ears and a choker with a stylized 'SD' on it.

Gays, lesbians, straights, bi's, other trans people all mixed and often Vivian wasn't certain where someone fit. When she realized that it didn't matter, she choked up a little.

Seeing a tear in her eye, Randall asked, "Are you ok? Did something happen?"

Vivian let a smile creep onto her face before she said, "No. Nothing happened. It's the people. Everyone is just people. Not men or women, just people."

Randall kissed her on the cheek as he moved to hold her hand. "Tonight is even better than a normal night here, isn't it? Everyone is in costume, but the costumes are obvious. Not costumes to blend in, costumes of who people want to be."

Vivian squeezed Randall's hand and leaned against him, "Thanks for encouraging me to come back after my first try. And for bringing me here tonight. These people are great."

"You would have gotten here on your own. You are stronger than you give yourself credit for."

The couple stood close, leaning against one another while watching the crowd of happy people. They both smiled as they watched the two Wonder Woman characters leave together. Other people were leaving together as well. After a few minutes, Randall asked, "Do you want to go home?"

Vivian sighed, "No. I want to stay here forever."

"If we stay too late, we will both be tired when we get back to your place." Randall ran his hand down the small of her back and let it linger on her ass with a gentle caress. The reminder of the toy hidden there was enough to convince Vivian that it was time to leave.

"We can come back, right?"

"Absolutely."

The drive to Vivian's apartment was quiet and comfortable. They held hands when Randall didn't need both to drive. Vivian led Randall to her apartment, unaware that he was staring at her swaying ass the entire time.

Once inside the couple embraced and Vivian held Randall close, squeezing his thigh between her own as she had seen the costumed couple do earlier in the evening. She let her hand drop to Randall's hard dick and said, "Is this for me?"

Randall ran his hands through her hair and kissed her back. "It is if you want it."

"I do. Let me pee first, though." Vivian rushed into the bathroom. Out of habit, she turned on the water so that Randall didn't know what she was doing. She pushed Randall inside once she was done. "Your turn, lover!"

It took Randall a couple of minutes to get soft enough to urinate, but he didn't run the faucet to cover his activities. By the time he was done, he found Vivian on her bed with the bottle of lubricant in hand, massaging her plug in and out. She was still wearing the skirt and sweater of her costume, but had removed her underwear. It wasn't the first time that Randall had seen Vivian's penis, but it was the first time she had not tried to hide it.

Randall hiked up his silky dress enough to kneel between Vivian's thighs. He let his fingers trace his own tight-covered thighs as he leaned close to watch Vivian probe her own asshole. He asked, "Would you like me to take care of that for you?"

"The plug?"

"Yes. And your big clit, too. If you want." Randall stroked Vivian's smooth, bare thighs.

"Are you sure?"

Randall slid Vivian's hand off the plug's handle and started fucking her with small, gentle strokes. "Very sure." Randall stroked Vivian's dick a couple of times and held it straight up so that he could lick the head. He stared up Vivian's body and maintained eye contact as he took her dick into his mouth for the first time since they got together.

Swirling his tongue around, Randall sucked on her dickhead while stroking her shaft and fucking her boy pussy with the toy. Vivian quickly orgasmed and shot her cum into Randall's mouth. He continued to make love to Vivian as she caught her breath. When she looked down at Randall, he stopped playing with her big clit and asked, "Is it ok if I fuck you now?"

Vivian laughed and said, "Use me, big boy, fuck me good. Please?"

Randall removed the plug, causing Vivian to sigh, before pulling his own dress up to reveal his hard dick. Vivian was already slick and stretched, so Randall started slipping into her with short, slow strokes. By the time he was taking full strokes, he had moved up over Vivian and was holding her down with his hands on her shoulders.

Vivian wrapped her legs around Randall's back while running her hands up and down his sides; she loved the feel of his dress covering his taught muscles. She made sure to pull his dress up to keep it away from their coupling. Randall focused on Vivian's red and glistening face as he approached his own orgasm.

"Are you ready? Can I do it?"

"Yeah, baby, come in me! Cream me good!" Vivian wasn't hard again, but she enjoyed the feel of Randall's dick sliding in and out of her boy pussy.

Thrusting all the way inside, Randall held himself as he squirted several times. Vivian smiled up at him as his face contorted in pleasure. Randall let himself relax down onto Vivian, but he held himself off her a little. He knew his whole weight had been uncomfortable for her in the past, but this time Vivian wrapped her arms and legs around him and pulled him down into a strong hug. A sigh escaped her as his weight crushed her just a little.

"Mmm, that feels so good."

Randall kissed her and replied, "I thought so, too." He moved his hips a little and asked, "Do you want me out?"

Vivian smiled and pushed him a little. "Yes, please. I want to clean up. I'll be right back."

Randall rolled over and lay on his back as Vivian left the room. A few minutes later she came back with a warm, wet washcloth and started cleaning his groin. "Can you stay tonight?"

"Of course. I don't have any plans for tomorrow, either."

Vivian grinned as she started disrobing. She had always been reserved about being completely naked with Randall, but tonight was different. Randall noticed and asked, "Are you ok? You seem changed somehow."

Shaking her head, she replied, "I'm good. Great, really. Everyone was wonderful tonight. They were just there, living their lives. Comfortable with who they are." She pulled on a pair of frilly underwear and her sleep shirt while Randall watched.

As she moved to get into bed, Randall stood up and said, "Hold on. Unzip me first, please." Vivian unzipped Randall's zipper and slid into bed. Randall made a show of undressing; he dropped the dress from one shoulder, and then the other; as it pooled at his feet, he bent over and slowly rolled his white stockings down.

Standing naked next to the bed, Randall asked, "Are you comfortable with who you are?" He pulled the underwear he had left on the floor earlier on before sliding into bed with Vivian.

As she cuddled up against Randall's side, Vivian smiled. "Yes. Are you?"

"I am comfortable with where I am and who I am with, yes. As for the rest? I'm still working on everything else." He bent his head and kissed Vivian on the forehead.

Drifting off to sleep, Vivian murmured, "I'm glad you are here."

"Me, too."

The end, for now.

**********

The Story Contests and Challenges are a lot of fun, and the authors work hard to make their offerings entertaining. Please check out the other submissions. Your votes and comments are the best way to support all the authors' efforts.

I am trying to complete the Survivor Challenge of writing in every Literotica category. I am also trying to complete the challenge while including the same character, Randall, in each story. Some categories are harder to complete than others.

If you have any feedback or suggestions, I would love to hear from you.

Thank you for reading!