Wicked Game Ch. 11


Nathan met them as they all gathered at the table for dinner. This time, no one groaned at his approach; his speech had adequately reminded them of the reality of their situation. They all sat together, much changed from the people they were days ago and much richer as a result. For some, the change had been financial but for all, the changes had been emotional and life-changing.

“Good evening.”

“Evening, Nathan.”

“Wow, you all very elegant tonight. Any special occasion?”

“No.” James spoke for the group. “We just thought it would be fun.”

“Ah, well, I have some good news for you. Tonight, one of you will receive the tenth scavenger hunt task and my benefactor felt that that would be a milestone for you. So, provided that the tenth task is completed, you will be flown to the Bahamas for a few days of rest, relaxation and for all of you, hopefully some sex.” The group cheered, smiling at each other. Nathan couldn’t help but notice that Ashley seemed distracted. “And speaking about sex, you will be permitted to invite one person to go on the trip with you.”

“Invite someone? I don’t understand.”

“Someone from home, Shane, such as a girlfriend or boyfriend. Maybe your sister or your mother. It’s up to you.”

Beverly heard Nathan’s words and saw that he had looked at her when he said the word, mother. There was no way in hell that she wanted to invite her mother on this trip. In the last nearly two weeks, she had lost almost fifteen pounds. She was so looking forward to this Bahamas trip so that she could do some shopping. She had no one that she wanted to invite. She stole a glance at James and wondered whom he would invite. “What if we don’t have anyone we want to invite?”

“Then you go alone. There’s nothing that says that you have to invite someone, Beverly. The offer is just out there for anyone who wishes to take it.”

Shane thought for a moment. Once again, he was the third wheel. Everyone else would be paired up, except him. He thought about whom he would like to invite and one name kept popping into his head. Jaime. Since he’d come to grips with his sexuality, he had given a lot of thought to his best friend and their relationship. He’d known Jaime since the first day of school and they’d been dorm mates ever since. Jaime’s room was directly across the hall from his and they spent a lot of time in each other’s company, either clubbing or studying. A couple of times, he had caught Jaime looking at him and wondered if he, too, was gay.

“I have someone I’d like to invite, Nathan.”

“All right. Give me the information and I’ll get to work on the details.”

Shane went off with Nathan, leaving the group to study their menus. James looked at Beverly, feeling a nervousness that he hadn’t felt in a long time. She hadn’t waited for his escort to dinner and even though she’d smiled at him when they were seated, the smile didn’t reach her eyes.

“How about you?”


James swallowed past the lump in his throat. “Are you going to invite anyone?”

“Don’t have anyone I’d want to invite.”

“Oh.” He watched as she returned her attention to the menu. “Beverly.”


“Why aren’t you talking to me?”

Beverly released a deep sigh. “I don’t know, James. Maybe I don’t want to get hurt.”

“Beverly, do you really think I’d hurt you?”

His eyes were so sincere but she’d heard of James Weathers before this hunt had started. She knew about his women and about his conquests and she had no wish to be another notch on his bedpost. “Not knowingly.”

“Not at all, Bev.”

“Is that what you said to all those other women?”

James saw the pain in her eyes and didn’t look away. “No. I didn’t say anything to those women.” He cupped her cheek gently. “I never felt this way about any of them.”

“But why me, James? An overweight puff of black woman.”

“I can’t really tell you why it’s you. I can tell you that I don’t see an overweight puff of black woman. I did when I first met you. But you’re different, Beverly. You’re different from any other woman I’ve ever met and it’s not just one thing, it’s a combination of things. It’s your color, it’s your laugh, it’s your smarts … but most of all, it’s what I see in your eyes.”

“And what’s that?” She asked softly.


Beverly’s heart skipped a beat, especially when he leaned forward and pressed his mouth against hers. Her stomach flopped and a deep liquid warmth spread through her pussy. James broke the kiss and she just gazed at him for a long moment. “Thank you, James. I believe that’s the nicest thing anyone has ever said to me.”

“I’m not saying it to be nice.”

“I know.”

Shane returned, his usual enthusiasm waking everyone at the table. “Well, ladies and gents, are we ready to order?”


Jaime Scott had been listless all day. He wasn’t sure why but he could trace its beginnings to the day that Shane had left on that scavenger hunt. Oh, fuck it! He went to the refrigerator and pulled out another beer. He knew exactly why he felt this way. He missed Shane. After all, Shane was his best friend. Best friend? No, Shane was more than that but he didn’t know what to do about it.

He remembered the first time he’d seen Shane. Jaime had been on assignment for the school’s newspaper, The Clarion, and had to take photos of the new football players. Most of the players were idiots, fresh from big-man-on-campus in their respective high schools, now low-man-on-the-totem-pole in college and resenting it immensely. All they seemed to want to talk about was where to find the easiest girls and which bars were the best.

Shane had entered the locker room, looking like a lost little boy among the beefier new candidates and offered him the warmest smile and most intelligent interview of the bunch. Jaime was instantly smitten. But Shane was the quarterback and very soon after, became the star quarterback, totally out of his league.

But much to Jaime’s surprise, Shane had sought him out after noticing him taking pictures of the game and had invited him to the after party. From then on, they were almost inseparable. There was a month or two when Shane had dated Loriann Carswell but that was it. For nearly three years, they were close pals.

What Shane didn’t know was that Jaime was in love with him. In love. He had discovered that just in these last two weeks. He had never had a relationship with a man, but he knew that he wanted to have one with Shane. His cock was hard just thinking about Shane’s naked flesh against his. The only problem was … he didn’t know if Shane was gay or not.

The phone rang, breaking his meditation and he grudgingly answered it. “Hello?”

“Hey, Jaime! It’s Shane!”

Jaime’s heart leapt in his chest. “Hey, Shane, where are you?”

“Lake Tahoe but we’re about to head to the Bahamas.”


“That’s a long story, Jai, and I don’t have that much time.”

“So what’d you call for?”

“We’re allowed to bring someone to the Bahamas with us and I want you to come.”

“You want me to come?”

“Yeah, Jaime. Frankly, I couldn’t think of anyone else that I’d want here but you.” Shane’s voice softened. “I’ve really been missing you.”

“I’ve missed you, too, Shane. It just hasn’t been … “

“The same? Yeah, I agree. Listen, Jaime, when you get down here, there’s something I need to talk to you about.”

“About us?”


Jaime’s throat dried up. “What is it? Just tell me.”

“No, I want to wait until you get here. I want to see you face-to-face.”

“You’re making me very scared, Shane.”

“Believe me, Jai, I’m petrified myself.” Shane cleared his throat. “Pack enough stuff for three days. Nathan’s gonna talk to you to get everything arranged and I’ll see you when you get here.”

“Okay, Shane.”

“Don’t be too worried about what I want to talk to you about. No matter what happens, we’ll always be friends.”

That statement scared Jaime even more. He swallowed and said, “I hope so.”


“Oh, Megan! You look sick!” Carmela Donato’s exclamation was heard by all the girls working front desk and she was right. Megan’s skin was white and a sheen of perspiration had broken out on her forehead. “What are you doing here?”

“Just wanted to make sure that everything was okay.”

“Everything’s fine, honey. You go back to bed.”

“Okay.” Megan turned to leave, then quickly returned. “Oh, Carmela, can you get me yesterday’s customer report? I’d like to look it over while I recuperate.”

“Sure. Can you watch the desk for a minute?”

“Yes, just please hurry.”

While Carmela went to fetch the report, Megan pulled the card key drawer open, found the key for room 510 and tucked it into her pocket. A moment later, her friend returned with a sheaf of green bar papers. “Here you go.”

“Thanks and tell Doris that I’ll talk to her tomorrow.”

“No problem. Get well!”

Megan nodded, holding the reports tightly as she fingered the stolen card key in her pocket, visions of her reward from Matthew dancing in her mind.


At the end of supper, Nathan appeared with an envelope and everyone held their breaths as he gestured for Shane to join him. “First, I wanted to tell you that all the preparations for your friend have been made. Once you complete the task, I’ll have the ticket issued and inform him of the flight times.”

“Thank you.”

“And now, the task.”

Shane opened the envelope and read the printed content. “By now, you should have had a nice dinner and are ready to accomplish your tenth task on the scavenger hunt. The tenth task is to have sex with a hooker of Nathan’s choice. Simple task? No. Shane must be chosen to accomplish this. The reward will be $5,000 dollars, with $2,000 for the non-participants. The proof required is an ass full of cum. The proof must be shown to Nathan. If you follow the instructions, you will receive the money upon completion.”

Shane looked up from his reading. “A hooker of your choice?” Nathan nodded. “What does that mean?”

“That means that I get to choose who you screw.”

“That doesn’t sound fair.”

Nathan just smiled. “Are you saying that you don’t trust me, Mr. Kingsley? I’m so disappointed.”

“Uh, no. I trust you, Nathan, you know that.”


“But in light of my recent … er, situation … “

“Ah, I see. You’re concerned that you’ll have to perform with a woman.” Nathan tucked the discarded invitation back into his jacket pocket. “Who said it was a woman?”

Shane perked up at that. “Then what … “

Nathan put his arm around Shane’s shoulders. “Buy me a drink and I’ll fill you in.”

The cocktail lounge was filled with people, mostly women dressed alluringly in short dresses or mini skirts and either dancing or mingling with others. Nathan went directly to the bar and found two seats on the far side and ordered two apple martinis. Shane had never had one before but he didn’t want to anger Nathan. After all, he was making the choice so Shane decided to check out the clientele.

“So, what do you think?”

“L-Looks good.” Shane accepted his drink from Nathan and took a sip.

“Picked anyone out?”

“No. I thought you were going to make the choice.”

“I am. I just thought you might have scoped someone out.”


Nathan nodded. “There are an awful lot of good-looking ladies here … “

“Nathan, you said … “

“I know what I said.” Nathan chuckled. “Just messing with you.”

“Um, excuse me.” Shane turned, smiling into the eyes of a gorgeous Spanish woman, holding a ten dollar bill. “Could you get the bartender’s attention for me?”

“Uh, sure.” Shane gestured to the bartender and watched as the woman ordered a mojito. “That’s interesting.”


“Your drink. Not too many people order that.”

“I can’t help it. I’m from Cuba and it makes me think of home.”

“I see.” Shane leaned back to talk to Nathan and found him gone.

“Your friend left. May I sit down?”

“Uh, sure.”

“I’ll give up the seat when he gets back, if that’s what you’re worried about.”

“Uh, no. That’s not necessary. You’re a lady and ladies get to sit. I’ll give him my chair.”

The woman laughed. “Is he a lady?”

“No, but he’s older than me.”

Her dark eyes sparkled. “I see chivalry is not dead with you.”

“Not at all.” He smiled. “I’m Shane.”

“I’m Rosalinda.”

“Nice to meet you.”

“Nice to meet you, too.”

The conversation continued over the next hour. Shane was aware that Nathan hadn’t returned during the first twenty minutes but after that, his attention was taken by Rosalinda. She was very witty and he so enjoyed laughter to ruminating on Jaime’s visit, worrying about its outcome. She bought the second round and they enjoyed the drinks, talking and laughing.



“Do you have a room here?”

“Would you mind if we went up there? It’s awfully loud down here.”

“Sure. Let’s order a drink and take it up.”


Once upstairs, Rosalinda sat on the bed and gave him a smile. “You seem like a nice man, Shane.”

“I am. Why, is there a problem?”

“No.” She pushed her shoes off, scooting backwards to sit at the headboard. “I think you’re really cute. But I have to be honest with you.”

“Yes?” Shane shucked off his shoes and sat down on the bed also. He had complained to Nathan about a female selection but he was captivated by this woman. She was beautiful in an exotic way but there was something about her … something that he couldn’t put a finger on, but something he wanted to explore. Nathan had never returned; he could only hope that she was his choice.

“I’m a … “ Rosalinda looked down into her drink. “I’m a … “


Her face pinwheeled from surprise to relief. “Yes, but I’m very fastidious about my partners and I always use condoms.”

“That’s nice to know.”

She looked up at him. “Are you okay with that?”

“Yes.” He touched her cheek. “Did Nathan ‘arrange’ you for me?”

Rosalinda’s smile was genuine. “I’m not supposed to tell, but yes.”

“Good. If Nathan trusts you, I trust you.”

Rosalinda set her drink down and moved closer to him. “Nathan is a sweet man. He said that you might like me so … I won’t charge you.”

“That’s all right.” Shane whispered, touching his lips to her teasingly. “I’ll pay you.”

Rosalinda threw her arms around his neck, pulling him close and pressing her coral lips onto his. He responded avidly, his tongue slipping through and tangling with hers. She moaned into his mouth and he shivered, feeling the buzz crawl down his spine and into his hardening cock. When her hand closed over his crotch, his groaned so loudly that she giggled. “Mmm, feels like something down here wants a little attention.”

“Oh, yeah.” He whispered against her mouth, opening his legs to allow her easier access. “How about you?”

Rosalinda took his hand and placed it on her thigh. Shane hummed in contentment as he slid his hand up her stockinged leg, pausing at her hip and running his fingers under the edges of her panties. She whimpered. He let his hand move farther down and … a penis?!?

“Holy shit!”

Shane just stared at the gorgeous woman, his mouth hanging open. She sat huddled against the headboard, her dark eyes filled with fear, then jumped out of the bed, heading for the door.


Rosalinda paused at the door, trembling in fear. “I’m sorry!”

“No, Rosa, I’m sorry. Please.” He kept his distance from her. “I just … I didn’t know.” Tears sparkled on her eyelashes. “I’ve never been with anyone like you.”

Her laugh was forced and nervous. “That’s all right.” Rosalinda opened the door. “I’ll see you later.”

“No, Rosalinda.” Shane grabbed her hand, giving it a gentle squeeze. “Please. Be my first.”

“Are you sure?”

“Yes.” He moved closer, pulling her into his arms. “The thought of you having a penis was a surprise but I’m so hard right now ... ”

He felt her hand move down and give him a squeeze. “Mmm, I see.”

“Will you stay?”

“Will you fuck me?”

Shane chuckled. “That’s a stupid question.”

“Then, I’ll stay.”

Shane pushed the purse off her shoulder, locked the door and wrapped her in his passionate embrace, kissing her deeply. Her small tongue sought to conquer his, tracing the ridges of his teeth and the contours of his lips. He smiled, pushing her back onto the bed and grasping her penis with sure and steady hand. She moaned, pressing against his palm and he pulled her panties down, taking her six-inch cock into his hand and stroking it. Without a second thought, he moved down and took her meat into his mouth, groaning over the sweet scent of her musk and the taste of her pre-cum.

“Oh, yes.” While Shane sucked her prick, she unbuttoned her dress, spreading it open and rubbing her nipples. “Oh, Shane. God, yes, suck my cock.” His tongue slid down its length, laving the soft skin and nipping the edges of the crown. She gasped, a tremble snaking through her body. Shane released her flesh and bit and licked the insides of her silky thighs, driving her crazy with passion.

Rosalinda’s tiny hands stripped him of his clothes and she pulled him down, her cock rubbing against his, spreading sticky juice onto their stomachs and her tongue over his lips. He bent down and took one of her nipples into his mouth, biting down on it and drawing a loud moan from her, his hand stroking her tool. “Turn over.”

Shane took the lube from her hand and squeezed a bit onto her pucker, using a finger to work it in. Rosalinda growled, pushing back and taking his finger up to the knuckle. “Come on, Shane. Quit teasing me. Put that goddamned chunk of meat in me!”

“Is this what you want?” Shane rubbed the fat head of his cock against her slick hole and she answered with a deep moan. He pressed in, closing his eyes and relishing that first feeling of his cock head being squeezed into a tight ass and sliding into its hot canal. He groaned, his hands on her hips as she pushed back into him.

“Oh, yes!”

He gave her a stroke, teasing them both into shudders of excitement, then moved again, finding a steady rhythm that had both breathless. Rosalinda was so beautiful, her sensual dark eyes heavy-lidded and her lips parted, pink tip of tongue just visible as she turned her head to share a lusty look. He pulled out, turned her onto her back and leaned down for a deep kiss, letting his cock find and slowly enter her again. Her entire body trembled and she whimpered with each stroke, her prick straining sandwiched between them.

“Oh, Rosa, you feel so good.”

“So do you.” She murmured against his mouth. “So nice and hard.” She gave a tiny gasp as the head of his cock found her special spot. “Oh, yes! Do that again!” He did, angling his hips just so and scraping her prostate. “Oh, God! You’re going to make me … “ Her gasp and the rippling of her anal walls around him signaled her orgasm, along with warm spurts of cum that greased the flesh between them. Shane tried to hold back, but the feeling of her squeezing his prick sent him over the edge. In the spanse of mere seconds, he felt his cock enlarge then explode, sparks lighting behind his eyes as he pumped her sweet ass with his cum.

Rosalinda welcomed him into the circle of her arms and they lay together for several minutes, panting together and basking in the afterglow of hot sex. She groaned softly as his penis slipped out of her ass. A knock at the door meant that their time was over and Shane arose, yanked on a pair of shorts and admitted the driver.

“Am I too early?”

“No.” Shane shook his head, watching as Nathan bent and peered between Rosalinda’s open legs, pushing a finger into her cum-laden anal canal and sticking the finger into his mouth, sucking it clean.

“Looks like I need to make a call. See you downstairs, Mr. Kingsley.”

Shane closed the door behind Nathan and turned to Rosalinda who had arisen, reaching for her clothes. “Want to take a shower with me?”

Rosalinda just smiled.

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