Friends With Extra Benefits

by Luke Young

  He watched, mesmerized, as she removed her pajama bottoms and underwear. His eyes traveled down to her completely shaved pubic hair. He swallowed hard and pulled off his shirt.

  “Do you want me to help you with your shorts?”

  He nodded. “Just watch my ankle.”

  Taking hold of the waistband of his shorts, she pulled them down as he lifted his hips off the bed. Then she pulled his boxers down and carefully slipped them off while avoiding his sprain.

  She drank in his body, and then her eyes settled in to watch his quickly rising erection. Climbing over him carefully, she settled her knees down on either side of his chest.

  Lisa leaned down slowly and kissed him. Slipping her tongue into his mouth, she kissed him more passionately. Her eyes rolled back in her head as she ground her hips into his groin.

  Craning her neck, she glanced down at his penis. “Wow, you’re so big.”

  Raising an eyebrow at her, he moved his hand to her breast. She pulled back in pain.

  “Sorry,” he said.

  “Neither of us is one hundred percent.”

  They shared a giggle.

  Lisa moved her hands down and wrapped them around his penis. She began massaging it as he closed his eyes and enjoyed the feel of her touch. Lifting up, she positioned his thick head at her entrance and held her breath.

  “Wait. Should I get a condom?” Eric asked.

  She took a deep breath and held still over him. “I’m on the pill.” He gave her a look, so she explained, “I know, a virgin on the pill sounds weird, but it helps regulate my period, and it really cleared up my skin.”

  “Huh.”

  “Ready?” Lisa asked.

  He nodded, and they stared into each other’s eyes. She opened her mouth wide as she fought for the right angle while still holding his shaft.

  “Oh…” he groaned.

  Finally she found it, and the tip pushed up quickly inside of her.

  “That’s…” Lisa began. She held her breath again and then slipped down onto him, her virginity now a thing of the past. Groaning in mild pain, she pushed down slowly until she was resting completely on him.

  “Are you okay?”

  “I think so,” Lisa replied. She wore a slight grimace as her body adjusted to the fleshy intruder. Circling her hips slightly, her expression shifted to a sexy grin. “Oh, my,” she moaned. “She was right.”

  “Who?”

  “Victoria.”

  Lisa began moving her hips up and down over him.

  “Right about what?” Eric asked breathlessly.

  “How amazing this feels.”

  He smiled. Leaning down, she pressed her lips to his while maintaining her rhythmic gyrations.

  About six minutes later, Eric exploded inside of her with a thunderous orgasm. Lisa didn’t have an orgasm that night but still went to sleep thoroughly satisfied with the matter of her virginity safely behind her. The next day, they took a bath together, and she experienced her first male-induced climax courtesy of what Lisa would refer to, when she shared every single detail with Victoria, as Eric’s magical tongue.

  21

  Jim and Caroline decided to return to the place where they first met, the Borgata in Atlantic City, New Jersey, for a New Year’s Eve getaway. Jim was able to book a reservation in a suite similar to the one where they spent that memorable night during the previous summer. The plan was to relive their experiences pretty much as they had on the night they met, except for a few minor role-playing adjustments. Jim didn’t know exactly what she had planned, but he was told to go to the casino and then search for her in one hour. He was instructed to retrace his steps exactly as he had on that fateful night.

  Jim slipped down to the casino and experienced absolutely none of the luck he had previously. When he found himself two hundred and fifty dollars down at the blackjack table, he checked the time and found he still had forty minutes to kill. While strolling around the casino, he noticed the roulette wheel and grinned. He pulled the remaining forty dollars’ worth of chips from his pocket and placed them down on twenty black, just as he had during his last visit. Jim waited while wearing a confident smile as the wheel spun round and round.

  The ball bounced around from slot to slot until it finally landed on double zero. His smile morphed into a frown as he vowed to never gamble again. He checked the time and discovered he had used up all of three minutes since he last checked. He spent the remaining time watching other lucky gamblers win at blackjack and then wandered around the casino while he waited for the real fun to begin.

  When it was time, he glanced around the casino, trying to recall what his next move should be. His eyes brightened as he remembered that after gambling, he’d enjoyed a drink at the bar.

  As he entered the Gypsy Bar, he discovered a woman facing away from him and dressed in a tight spaghetti strap black dress. She looked incredibly sexy with her hair up and Jim stood staring, his eyes followed her long neck as it tapered down to her slim shoulders. From there, he cocked his head to one side as his glance headed further south to the woman’s tiny waist and slightly curvy hips. It, of course, was Caroline.

  Grinning, he moved to the bar and sat across from her. Aside from the bartender, there were only a few other people around. The bartender approached Jim and took his order, a gin and tonic. Jim made eye contact with the slender beauty, and they shared a smile. When his drink arrived, Caroline moved to the seat beside him.

  She began in a mock Russian accent, “I Tatiana.”

  Jim looked around nervously as if she were speaking to someone else and then glanced back at her. He replied, “I’m Jim.”

  She leaned closer to him with a big smile. He glanced down at her cleavage and narrowed his eyes.

  “Will you buy me drink?” she asked.

  “Uh, sure.”

  “Seven and seven.”

  Jim relayed the order to the bartender.

  Caroline smiled at him and asked, “You staying here?”

  “Yes. Why, yes, I am,” Jim replied a bit awkwardly.

  Caroline gave him a sexy look. “Are you looking for company tonight?”

  The drink arrived as Jim stammered, “Uh, sure. Well, I mean… I have a girlfriend, but—”

  “Five hundred for an hour or two thousand for the whole night.” His eyes widened, and she continued, “For that price, we can do anything you want. Well, except the anal. If you want that, it another thousand.”

  He gave her a casual nod. “That seems pretty reasonable.” Jim paused a moment to let the offer sink in. “So, for three thousand dollars, I can have anal sex with you all night long.”

  Caroline leaned in an inch from his face and fought desperately to hold back her laugh as she said, “And you never forget it.”

  He pulled back a little. “Look, you are gorgeous, but I can’t. I’m actually sorta pre-engaged so—”

  “So, you haven’t actually asked her to marry you?”

  He shrugged. “Well, not technically.”

  “You’re not really engaged then.”

  “I guess you make a good point.”

  “Does your precious girlfriend do everything?”

  “What are you asking?”

  “Does she give you the anal?” Caroline said in a soft, sexy voice as she ran her hand down his shirt to his lap.

  Jim’s eyes followed her hand down. “Oh, well, um sometimes.”

  She squeezed his package hard. He grimaced in pain and then glanced around the bar nervously before looking her in the eye.

  “Yes, she does. She’s a real trouper about that. I mean, like, you know…”

  “When is your girlfriend supposed to meet you here?”

  “She should be here any minute.”

  Caroline gave him a tired look and then asked in her regular voice, “Are you sure, Jim?”

  Shaking his head, confused, Jim said, “I mean, she was supposed to meet me here, so—”

  She put her fingers gently to his lips to sto
p him from speaking. “Would you excuse me for one second?”

  Turning away, Caroline pulled her cell phone from her purse. She smiled at him and then began typing a text message.

  Jim, sorry running late. I’ll be there in one hour.

  She turned back to him and smiled. “Now, where were we?”

  His phone beeped, and he pulled it from his pocket. “Sorry. Do you mind?”

  Caroline shook her head and waved her hand at him to proceed.

  After reading the message, Jim gave her a big smile. “That was my girlfriend.”

  “Really?”

  “Yes, she won’t be here for an hour.” A smile spread across his face as the lights finally came fully on. “Ohhh… She won’t be here for an hour.”

  They shared a smiling nod. “You see, I didn’t get a lot of sleep last night, so I’m a little slow today.”

  Caroline jumped out of character and said, “That’s okay, just try to keep up.”

  “I will.”

  “Ready?”

  “I think so.”

  She placed her index finger on his arm and traced it slowly in a circular shape as he smiled and stared down at her hand. After a moment, she widened her eyes and glared at him. He glanced up at her face and shook his head. “I forgot where we were.”

  Caroline said, “Here, I’ll start again… So, it sound like you will be all alone.”

  “Oh, yeah… I’ve got it.” He attempted to put on a confident grin as he asked, “So, how much did you say for an hour?”

  “Five hundred.”

  “Would I have to wear a condom?”

  She broke character for a moment and nodded approvingly at the sexy question while wearing a bright smile. Then she jumped back into her role and frowned. “Of course.”

  “Even for a blowjob?”

  “You must.”

  “What if I had a little more money?”

  Caroline nodded casually. “For seven hundred, I’ll suck your big cock slowly for a whole hour, no condom.”

  “Will you swallow?”

  Glaring at him, Caroline lost the accent completely. “Don’t push it.”

  He widened his eyes. “Okay, gee, I was just having some fun with it.”

  “So, do we have deal?”

  Jim nodded.

  Two minutes later, they were in the elevator heading up to the twenty-fourth floor. A couple in their early sixties stood next to them. The wife glared at the scantily-dressed Caroline, and the husband’s jaw dropped as he eyed her up and down.

  After catching the woman’s judgmental gape, Caroline shot Jim a quick look. Then she said softly, “Remember, you must pay first.”

  Jim’s eyes shot to the woman, and he spotted the look of horror on her face. The man was grinning. Jim murmured uncomfortably, “Okay.”

  Caroline looked directly at the woman. “Trust me, you’ve got to get the money up front. Once they finish, they don’t feel like paying anymore.”

  Gasping, the woman turned to her husband. She found him leering at the supposed hooker. The wife narrowed her eyes as she punched him in the arm. The elevator doors opened, and the woman dragged her husband into the hall.

  As the doors were closing again, Jim and Caroline broke into giggles. Jim said, “That was mean.”

  “It was, but she was giving me a look. She totally deserved it.”

  “You probably ruined her evening.”

  “I don’t care.” Her frown morphed into a smile. Moving to him, she wrapped her arms around his neck. She pushed her body against his and felt his near erection pressing into her stomach. “You’re already hard!”

  “A little.”

  Caroline moved her hands down to his groin and squeezed. Jim groaned, “Yeah.”

  “I feel like pulling you out right here and—”

  “They have cameras, you know.”

  “Yeah, right.” She pulled her hand away and glanced at the ceiling of the elevator with an apologetic smile. “I think I can wait.”

  The elevator doors opened, and the horny pair rushed to their room.

  Once inside, Caroline stayed in character. Pushing him against the wall, she slipped down to her knees and began running her hands over the bulge in his pants.

  Jim leaned his head back against the wall, closed his eyes tight, and exhaled. “Oh, wow.”

  She unzipped his fly, reached in, extracted his nearly-hard equipment, and began massaging it with both hands.

  Caroline smiled up at him with one eyebrow raised. “You have nice size cock.”

  Jim glanced down at her. “Gee, thanks.”

  Her silly expression changed to a more passionate look just before she plunged her mouth forward, swallowing half his length all at once. Jim spread his hands out wide and grasped for something to hold onto. After finding nothing but the wall, he brought his hands back and put them on the sides of his head. He stared down, dizzied at the sight of Caroline’s passionate attention.

  She kept running her mouth over his length, back and forth, slurping and sucking, as he stood completely still and gasping for breath. Moving his hands down to the straps of her dress, he pushed them over her shoulders. He slipped his fingers to her breasts and worked the fabric down to uncover them. She groaned as he squeezed her nipples firmly. He gazed down at her breasts and began pumping his hips back and forth in small strokes to drive his erection deeper into her mouth.

  Her eyelids fluttered as she floated away in ecstasy, imagining that they were fucking right at that moment. He pushed too fast toward her and caught the back of her throat, causing her to gag. After recovering, Caroline gave him a mock-scolding look as she shoved him hard against the wall and held him there with one hand.

  Jim stared down at her, open-mouthed and panting, as she used her other hand to unbuckle his khakis and pull them down to his ankles. After bringing both hands to the waistband of his boxer briefs, she tugged them down to his knees. She stared at his hovering erection before opening her mouth wide and taking him back inside.

  Groaning loudly, Jim brought a hand to her face and brushed it against her skin. He closed his eyes as she went on pleasing him. After a few minutes more, he couldn’t take it any longer.

  “I’ve got to taste you,” Jim said as he gently took her head in his hands and coaxed her carefully away from him. Sliding back from him, she followed his lead and remained on her knees, just glancing up at him patiently. He kicked off his shoes, slipped down to join her, and kissed her wildly, shoving his tongue deep into her mouth.

  He moved his lips to her neck and sucked at her tender flesh for a moment before sliding down to her breast. He nibbled roughly on her hard nipple before opening his mouth wide and sucking it between his lips. Closing her eyes, she ran her fingers through his hair as she took in a long, deep breath.

  Jim pulled up and drank in her sexy body as the tiny black dress fought to cover her. Her large, firm breasts and creamy thighs were exposed, the fabric bunched around her torso as she remained in that kneeling position, simply waiting breathlessly for what was to come. Staring deeply into her eyes, he moved his hand to her back and gently guided her to the floor.

  Jim took hold of her dress and pulled it up over her hips to expose the tiny black thong that covered her. She spread her legs wide as he moved his mouth lower. He placed his tongue directly on the tiny strip of black satin between her legs and licked hard.

  “Oh, Jim!” she cried out.

  After pushing her panties down, he plunged his head into her and went to work. Using his lips, mouth, fingers, and tongue, he pleased her as if they’d been separated for months.

  Minutes later, she had more than enough of his teasing. She desperately wanted to be filled up and not with more fingers or tongue. She wanted him deep inside her.

  “Put it in,” she moaned softly.

  Pulling up, Jim gave her a curious look.

  “Put it in,” she repeated sternly.

  He knelt up and frantically fought with the buttons of his shi
rt as she tore the dress up and over her head. He kicked his khakis and boxers off as she spread her legs, waiting for him to take her. Jim moved over her, and her hands quickly went to his manhood. He pressed his tongue deep into her mouth as she guided him to her entrance.

  Caroline sucked on his tongue just as he pressed his hips down and slid inside. Wrapping her hands around his back, she pulled him closer.

  He stared into her eyes as he began pumping back and forth, with her pulling him harder into her body with every downward thrust. Soon they climaxed together for what seemed like the first time. It was the perfect beginning to a special night.

  Twenty minutes later, Jim and Caroline relaxed together in the large soaking tub. The toes of her left foot toyed with one of his nipples as he worked his fingers into the heel of her right foot. Caroline cocked her head back and closed her eyes. “God, that feels amazing.”

  “You like that?”

  “Uh-huh.”

  “I read there are all these pressure points in the feet.”

  “Really?”

  Moving his attention to her toes, he said, “Like, if I touch a certain part, I can take away a headache, or another part will stimulate your clitoris in some strange way.”

  “Do you know which spots do what?”

  “Sorry, I didn’t get to the end of the article.”

  She chuckled. Jim moved his fingers to the ball of her foot and worked it firmly.

  Opening her mouth wide, she leaned her head back against the tub. “Wow, I swear I just had a little orgasm… I think you actually reached my G-spot.”

  Jim grinned. “I’ll try to remember what I just did there.”

  He moved forward to take her big toe into his mouth. She lifted her head and giggled. “You know I don’t like that.”

  He pulled his lips from her toe and said, “I love your feet.”

  “You’re weird.”

  “Oh, you like it.”

  “Maybe a little.” She grinned as he took another toe between his lips. He massaged it harder as he ran his tongue around her second toe.

  “You can keep sucking them if you keep rubbing them hard.”