Trey and the Lost Bet

*Author's note: Everyone is over 18 in this work.*

Horny and desperate were Trey's most pronounced personality traits. Traits that always seem to get him into trouble. Tonight, was no different as he was now in the midst of poker game with three smoking hot babes. A poker game he was losing badly. When they came up to him earlier that day in the college cafeteria he thought he was in a dream. They were being all smiley and flirtatious and Trey didn't know how to handle it. These were the cutest girls who he had known since high school and here they were talking to him, acknowledging his existence, and seemingly flirting with him. He didn't have a chance.

They invited him over for a game, he didn't know it was poker at the time, but for them he would have agreed to anything. He recalled how Summer approached him her long blonde hair swaying freely as she walked, her stunning blue eyes so bright they almost burned to look into, on her face was smile that would knock anyone off their feet. She wore a yellow sun dress that showed off the cleavage of her ample tits, the skirt portion flowed whimsically around her tight ass. Seeing her like that brought him straight back to high school where they attended together where he often fantasized about her. Behind her was her best friends Violet and Samantha.

Violet wore a short green dress that complimented her busty figure, her curly brown hair tied into a tight bun. She was shorter and curvier than Summer, but still quite stunning, her brown eyes were hidden by sunglasses. Samantha was freckled redhead with emerald green eyes, taller and thinner than the other two and more cute than gorgeous, but her bubbly personality made her magnetic to say the least. She wore red summer dress which split the difference in length between Violet's and Summer's.

"Hey Trey! We haven't seen you since graduation! How have you been!?" Summer asked all smiles while Violet and Samantha matched her expression. The way they smiled at him both confused and aroused Trey. He couldn't place what the emotion behind the smile was, mainly because he could read the emotions of women due to his lack of experience, all he knew was that this experience was new to him.

"I-I've been good Summer!" He said a little too loudly, squeaking as he did. The girls exchanged a series of smirks at his response.

"Soooo we were gonna have a little game night tonight. Just the three of us and we were wondering if you wanted to join us?" She said without her mysterious smile leaving her face.

Trey didn't even need a second to respond. "Yes! I'll come!" He said with way too much enthusiasm. The girls exchanged some looks like they were fighting back a laugh, Trey assumed it was due to his over-enthusiasm.

"Great! Here's my apartment's address! Be there at 8 tonight!" She said as all three girls flashed a big smile and walked away. Trey had watched them eagerly as their asses swayed.

That was earlier though and now Trey was losing badly. He wouldn't care normally as he was just happy to spend time with the hot ladies, but unfortunately the stakes were something he couldn't afford to lose.

He recalled when he arrived. He had been so eager all day, he could barely sit still in class or focus on anything at all. He just kept thinking about Summer, Violet, and Samantha. He had knocked on the door his heart beating so hard he thought it would pop out of his chest. Within a minute Summer answered the door. Instead of the dress she wore earlier she now wore a pair of light blue leggings that showed off her toned legs and ass, her top was a black spaghetti strap top, showing off even more of her tits than earlier. Trey's eyes bulged at the sight, Summer smirked and invited him in.

Violet was on the couch, her hair down and styled now as her loose curls framed her face, she wore a black sports bra with short orange booty shorts. As Trey walked in he also saw Samantha coming down the hall from the bathroom wearing a red tube top, a black pencil skirt, and nylon stockings.

Trey felt like he was underdressed in just some jeans and a plain t-shirt. He admitted as much while complimenting how stylish and attractive the girls appeared. They all giggled and thanked him for the compliment. They asked if he wanted a drink and he accepted. They hung out awkwardly for around ten minutes drinking when Summer finally spoke up about the game.

"So, we invited you over here to play a little game Trey?"

"Y-yeah you mentioned that." Trey replied nervously.

"Well we were thinking of playing poker. Have you ever played?" Samantha spoke up smiling cutely.

"Uh yeah once or twice." He had played before but not seriously and he could barely recall the rules.

"Good! So, we wanted to play that!" Summer said excitedly.

With that Violet got out a deck of cards and started expertly shuffling, making Trey a little like he was outclassed. Samantha got out some chips and they all moved to the table.

They played for about a half hour, mostly quiet and awkward, when Violet spoke up. "This is kind of boring with no real stakes..." She trailed off.

Samantha also spoke up. "Yeah what can we do to make it more interesting?" Trey started feeling bad like he was the reason this was so boring. He wanted them to have fun and he thought he would do anything to ensure that outcome.

"Well..." Summer started. "We could raise the stakes a little bit..." She said suggestively causing the other girls to smile wickedly.

"What do you have in mind Summer?" Violet asked.

"We could make a little bet?"

"Oh! What kind of bet?" Samantha said without her devious smile changing.

"How about whoever loses has to strip and run around the apartment complex naked!" She said excitedly. Both girls laughed and quickly agreed, but not before Violet accused Summer of being a bad girl.

The three turned to Trey and he nearly broke into a cold sweat. He had to admit that the idea of seeing any of these girls nude was exhilarating, he had never had sex yet and seeing hot girls naked in person would be the greatest experience of his life so far. He mulled it over for another minute before he shyly agreed.

Before long Trey couldn't recall what it was like to think that it would be nice if the girls lost as he was now on the verge of losing and he was scared out of his wits. The girls were ringers who turned up the heat as soon as the bet had been made.

He had a few chips left when he was dealt pocket kings, he decided to play it safe and check. The girls all checked as well, on the flop a king, an ace, and a 2. Trey's hard leapt as he saw an opportunity to win. He bet half his stack and Summer called, her expression completely neutral. Trey couldn't read her at all. Violet and Samantha folded.

The turn came next and it was a 10. Trey went all-in, honestly hoping she would fold and he would increase his chip count by half, however she called. He and her both turned over their cards and his heart leapt once again leapt as she had an ace and a two. His 3 of a kind was the better hand and he started grinning. He was still in this game he was going to keep playing and avoid humiliation.

His elation was short-lived however as the river was an ace. His heart sank and his expression shifted from happy to forlorn in an instant. The girls all grinned deviously as they looked to Trey.

"Well, well, well. A full house. It looks like you lose." Summer said as she haughtily sat back into her chair staring into Trey's eyes. Trey sank into his chair hoping he could just teleport out of their or go back in time or anything to get out of the predicament in which he found himself.

"A bet is a bet! Now don't be a bitch and strip!" Violet said forcefully, standing as she did so.

"Look I know it's embarrassing," Samantha said with an almost understanding tone, "but you shouldn't welch on a bet, I mean you wouldn't want to disappoint us." Pouting her lips as she said the last statement.

Summer just sat back smugly and said. "Well, we're waiting."

Trey being a man of his word had no intention of backing out though he did feel he was tricked into this situation. He was so nervous he was shaking, but he still moved himself. First, he took off his socks and shoes. Then his t-shirt, the girls giggled little bit then.

"You're so pale!" Violet teased harshly.

"I think it's kind of cute! At least he's in good shape! It's always more fun when the guy is attractive!" Samantha said winking. The encouragement did make Trey feel a little better and he was surprised to hear that she thought he was cute.

Now he proceeded to unbuckle the belt in his jeans, the girls watched captivated. Next, he unbuttoned the jeans themselves. They now all wore matching devious grins. He bunched his jeans at his ankles and stepped out of them. Violet picked up all his clothes and put them on the table. He was now only wearing his boxer briefs before them, he shivered not from the cold but from the nerves.

"Enough stalling!" Violet said as she walked over and yanked his underwear to the ground. He quickly cupped his privates, shielding them from prying eyes. Violet pulled sharply on the bunched undergarment at his feet causing him to stumble out of them. He caught his balance without revealing his manhood so they still hadn't seen all of him.

Summer laughed as she stood up. "Wow! A little shy there, Trey? What are you hiding behind those hands?" Her expression was one of pure amusement.

"I bet it's tiny that's why he's hiding it!" Violet teased with a spiteful smile across her face.

"Guys it's not really fair to him. He could be a grower. Of course, he's shy he's never been naked with one woman let alone three." Samantha interjected on his behalf. Trey's felt like protesting that he had been with a woman but he thought they wouldn't believe him and what was the point anyway.

Samantha got up and walked over to him with a warm smile that made Trey feel very warm. She circled him once while the other two watched mischievously. As she came behind him, Trey felt goosebumps form all over as she got an unobstructed view of his ass. The he felt a sharp slap on his cheeks (not on his face), causing him to jump and face her.

Samantha had as sly smirk. "Sorry I can't resist smacking a nice bare butt when I see one." Trey was dumbfounded. He couldn't comprehend what he just heard, but before he could process it he heard a wolf-whistle come from behind him and he turned quickly.

Violet had apparently been appraising his behind and approved as she had an open grin, Summer had only a small smirk. "You aren't wrong Sam! He does have a nice ass!"

"Well Trey are you just gonna stand there with your hands on your balls or are you going to show us what you got!" Summer said speaking up her smirk never leaving her face.

Violet spoke up again. "Yeah show us that dick!"

Samantha got in between them and Trey. "C'mon girls he's nervous. I think he needs some motivation." She turned to him then and grabbed his waist and pulled him in for a kiss. He was so taken aback he froze until he realized the heaven he was in and began kissing her back, his hands never leaving his package.

She pulled away slightly and moved her hands further on his back to his ass, pulling him closer then she whispered to him in an intimate tone. "Trey we all want to see it. I know your nervous but it's gonna be so hot. I get it, you don't want to disappoint us. I know you won't just embrace the feeling I can see plastered on your face and show us how big you can get!"

The combination of her words and her hands on his ass caused the desired effect to take place. Before long he hands could no longer cover himself completely. Samantha noticed pulled away and looked down. She returned her gaze to Trey and whispered "Now I know they won't be disappointed in that!" She said with a smile.

She separated from Trey and walked to join the other two all while Trey dumbly covered his aroused member.

"Now Trey, it's time. Drop your hands." Samantha said with a kind tone smiling sweetly. Trey complied and the girls fell silent.

They each dropped their jaw, their eyes smiling. The tension was in the air as each person in the room was feeling the eroticism of the situation. Trey had to admit this was the most turned on he had ever been and it showed!

Violet was the first to break the silence. "Jeez Trey! Down boy! I mean woof!" She said grinning at him.

"How on Earth did you not get laid in high school with that monster!" Summer added.

"Oh Trey! I knew you were cute, but I had no idea you were such a stud-muffin!" Samantha said beaming.

Trey rubbed his shoulder self-consciously feeling more naked than he ever had before as the women drank in the sight of him shamelessly.

"Well that was the first part of the bet. Now for the rest of it!" Summer said grinning maniacally.

"That's right! You have to streak our complex now!" Violet said giddy at the prospect.

"I guess a bet is a bet..." Samantha said with a hint of reluctance in her voice as she looked sympathetically at Trey.

For the first time Trey spoke up. "Please don't make me do it!" He pleaded. Samantha looked like she was ready to cave, but Violet and Summer were stalwart in their resolution.

"Not a chance! You wouldn't have let us out of streaking so we're not letting you skip it!" Violet teased.

"That's what you get! Don't let your mouth make a bet your ass can't cash!" Summer said rebuking Trey.

"Listen girls! I could get arrested, if someone saw me-"

"Ha! Well then you better not get caught!" Violet interjected.

"B-b-but-"

"No, you can't cover your butt! That's silly!" Summer mocked. "Listen the sooner you do this the sooner it'll be over. Here we'll sweeten the deal. You make it all the way around the complex and Samantha here will show you her tits! How does that sound?"

"Her tits?" Trey said looking to Samantha who was now blushing and smiling shyly. "You would show me your tits?"

Samantha giggled a little bit. "Yeah I could do that." She said shyly smiling and looking to the corner of the room away from Trey cutely.

Trey looked at her chest and his dick jumped at the prospect. Violet laughed, "I think he likes the idea!"

Trey got frustrated that he couldn't hide the effect Samantha had on him from his audience. Try as he might he couldn't deny that the chance of seeing her tits was way too tempting to give up.

"Okay, I'll do it!" Violet jumped up and cheered, Summer sat back smugly, and Samantha blushed a little bit deeper red.

They all made there way to the door Trey grabbed the handle and looked back at the girls. His gaze lingered on the eyes of Samantha for a moment, then he glanced at her rack then back to her eyes and she smiled once again. He thought to himself that he would do anything for that girl in that moment.

"Let's get this show on the road!" Violet shouted.

Trey took one more deep breath, turned the doorknob and exited.

As soon as the door shut behind him and the cool night air hit his skin he regretted his decision. He turned to the door to open it, but his heart sank as he heard it lock and two female voices laugh maniacally behind it.

He realized that he had no choice now and so he went off into the night hoping he wouldn't get caught.

There was no one on the walkway on the floor he was on, but anyone in the parking lot could see him if they were there, only a short safety rail shielded him and it provided no where enough coverage to hide his nudity. Trey conscious of this got moving as quickly as he could without making noise, hoping he wouldn't run into anyone in such a vulnerable state.

He made his way to the nearest staircase and made his way down. His heart pounded with every step and his stiff cock bounced with every movement. By the time he was at the bottom he found his nerves were at a maximum as was his erection.

On the bottom floor he found himself running briskly trying to get all the way around the complex as fast as possible. As he ran his mind drifted back to the three girls, the way they stared at his nudity, the way they teased him, the way Samantha whispered to him. With that last thought he felt his dick jump. He realized that this was no way to get rid of a boner and so he stopped himself.

Before long he came to the center of the complex which was comprised of a courtyard with a small pool and jacuzzi, surrounded by a fence and the four buildings that constituted the complex. He began running across on one side underneath the walkway on the second floor, so no one above him could see him except across the courtyard. It felt nice to have some shielding.

He was about to go into a small exterior hallway that led to the back parking lot when he heard the gate ahead of him open. In the hallway was a woman in business attire looking at her phone and carrying a small bag. He panicked and turned to run. He knew he only had a few moments before she would look up from her phone so he needed to act fast. The adrenaline quickened his decision making. He thought through a dozen options in his head in an instant until he resolved his best option was the a bubbly jacuzzi dip while she passed.

Trey opened the fence, turned on the bubbles, and jumped in. He tried to settle in and look casual as she passed. When she came into view she was already looking at the jacuzzi. Trey recognized her in the dim light of the pool area as someone from his past. When they made eye contact he could see a glimmer of recognition in her eyes as well.

"Trey! Is that you?" she said.

"Y-yeah!" He squeaked failing to act nonchalant. Then he recognized her "Tiff-Tiffany! It's nice to see you!" he said trying to feign enthusiasm and hide his embarrassment.

"I didn't know you lived here! I haven't seen you since we worked at Ollie's together! How long has it been? 2 years?" She said smiling widely at him.

"Uh...Almost 3 I guess." He said lamely. He actually knew for a fact it was close to three years as he remembered when she left. Trey had had a massive crush on her, at the time she had braces, deep blue eyes, and bright brown hair that shimmered in the sun. Now it seems that the braces paid off as her smile was gorgeous and so was the rest of her. "And I don't live here I was just visiting a friend, we came to the pool and he decided to go to bed. I didn't feel like leaving yet that's all."

"Well, why don't I keep you company? I have a bathing suit in my apartment, don't move!" She said enthusiastically and rushed to her apartment. Much to Trey's chagrin it was right in front of the pool so she would be back quickly.

Ordinarily he would be enthusiastic about spending time with Tiffany while she wore a bikini... or less. Now though, he was scared to death she would notice his nudity and think him a pervert. He was about to get out and make a run for it when her door opened. She now wore a revealing blue polka-dot bikini. Trey's eyes nearly bulged out of his head and his cock, that had been relaxing at last, lurched upward causing Trey to sink a little deeper in the jacuzzi.

She came in the gate, set down her towel, and joined Trey in the jacuzzi. Trey had never been so grateful for bubbles in a jacuzzi in his life.

"So how have you been!? It's been so long! What have you been up to?" She asked her smile never leaving her face.

"Well...I've been going to school mostly. I want to better myself, you know?"

"That is great! I love it when a man shows ambition!" Trey blushed at the comment.

Trey realizing it would be rude not to ask about her started. "So, what have you been up to?"

"Well, I got a job at this office, it kinda sucks but it's not too bad. It certainly pays the bills!" She said with a laugh. Trey laughed trying to hide his nerves.

"I always found jacuzzies so relaxing. Like, this is helping me unwind so much after work! Don't you just find this relaxing, Trey?"