A Night to Remember

Hello, everyone. I decided to try something a little different with this story, sort of coming out of my comfort zone by switching perspective. This is a story more fantasy than truth (though there are some true elements still), so I thought that was appropriate. I hope you agree. It's also a bit longer than my usual offerings. Please let me know in the comments if you think it came out all right or not. Enjoy!

*

They were hoping for a night to remember.

Ali and her sometime girlfriend Sharon were visiting Ali's hometown for the weekend. While they were there, they were going to see an old friend of Ali's in a show. Dean and Ali had reconnected on social media recently. When Ali mentioned that she would be in town, Dean quickly invited her to come see his performance. Ali was happy to agree. She'd had a crush on Dean back in her school days. Going through his social media now, she remembered those old days. And, she was pleased to see, he'd grown even more handsome in the intervening years. A chance to renew and perhaps deepen a friendship? Why not?

She told Sharon about wanting to see Dean's show, and showed her his pictures. Sharon agreed that he was quite good-looking and that the show seemed like a fun idea. Perhaps afterward they could go out for drinks, she suggested. And maybe, she continued, with a frank look at a particularly sexy picture of Dean, come back to the hotel for something more...Ali laughed lightly and gave Sharon a quick peck on the lips. They'd never done anything like that before, but there was a first time for anything...if Dean was interested, that is.

The night of the show, they prepared themselves excitedly. They laughed as they dressed, modeling various combinations of underwear and outerwear, hoping to coordinate and come of as easygoing, up for anything, but not overeager. They settled on contrasting dresses: Ali in blue, Sharon in red. Makeup, some artfully placed perfume, and some quirky accessories completed their look. Going braless and with panties in opposing colors—Ali's red, Sharon's blue—made them feel confident and sexy. Ali waggled her eyebrows suggestively as Sharon posed for her. "If Dean doesn't want to come back here, I may just ravage you myself," she said with a grin, reaching out to squeeze one of Sharon's breasts. Sharon laughed, swatted Ali's ass, and answered, "Not if I ravage you first." After a quick kiss, they left the hotel hand in hand to head to the show.

The show was lots of fun. Dean looked amazing on stage, mesmerizing. Ali felt herself getting wet watching him perform. She looked over at Sharon, who was equally entranced. The two squeezed into a hug and squealed with laughter.

After the show, they waited in the lobby of the theatre. Dean had texted Ali he would meet them there after he got cleaned up and changed. Eventually he joined them, smiling broadly. Ali opened her arms and pulled him into a tight hug, closing her eyes and inhaling his scent as he squeezed her in his arms. When he let go, she stepped back and indicated Sharon. "Dean, this is my friend Sharon. Sharon, Dean." Dean smiled at Sharon—a killer smile that made her knees go slightly watery. He held out a hand and said, "Pleased to meet you," in his low voice.

Sharon regarded the outstretched hand with a slight smirk, then pulled Dean into a hug of her own. "Why should she get all the fun?" she whispered into his ear. Surprised and amused, he laughed and returned her hug. She arched her back slightly, pressing her breasts into his chest.

My god,

she thought,

he really is hot. This will be fun...

Dean suggested they adjourn to a nearby bar. The girls had come in an Uber, so they all piled into Dean's car to make the short trip. In the bar, they sat at a booth, the girls on either side of him. They toasted each other, his performance, and their trip. Dean and Ali spent some time catching up, and Dean asked Sharon to tell him about herself. Time passed pleasantly for all. At one point, following a prearranged signal, Sharon excused herself to go to the restroom. After she'd left, Ali winked and whispered to Dean, "She's really into you." Upon Sharon's return, Ali excused herself. Sharon scooted in close to Dean and murmured, "Ali can't take her eyes off you. You know, she's had a crush on you for years."

Dean was no fool. He realized the two ladies had planned this evening, and couldn't wait to see what they had in mind. Looking into Sharon's eyes, he said, "She is very attractive. You are, too." Greatly daring, he put a hand on her knee. Feeling her nipples tighten, she smiled sexily and put one of her hands on his, giving it a slight squeeze. When Ali returned to the table, Sharon gave her a knowing look and a smile. Ali suggested they pay their tab and return to the girls' hotel room.

After driving downtown and parking his car, Dean walked into the hotel with Sharon on one arm and Ali on the other. In the elevator, Sharon's and Ali's arms moved down Dean's back, clasping each other's hands and squeezing his butt. He laughed at this, then dropped his hands down to squeeze each of their backsides as well. They giggled; then Ali pulled Dean's head down and kiss his cheek. Sharon repeated the gesture on her side.

They got out of the elevator and walked to Ali and Sharon's room. Once inside, the two ladies stood in front of Dean, holding his hands and each other's. Dean looked from one to the other—blonde Ali, brunette Sharon, each regarding him with open desire. "You were amazing tonight," said Ali in a low voice. "So very sexy," said Sharon softly. Dean regarded them both. "You both look so sexy tonight. Very hot." He squeezed their hands and smiled.

Ali took the lead. Still holding his and Sharon's hands, she stepped forward and raised herself up to give Dean a gentle kiss on the lips. Before he could get too engaged, she pulled back and glanced at Sharon. Dean looked at her as well, and she too stepped up to give him a brief kiss. Then Sharon and Ali kissed each other. They pulled apart and looked at Dean. Ali bit her lower lip; Sharon licked hers. Dean felt his blood boil in his veins. His cock created a slight tent in his pants.

Ali gave Dean and Sharon another quick kiss, then went into the restroom. Once in there, she reached under her dress to flick her fingers against her clit through her panties. All the flirting and kissing had made her extremely wet, and the slight touch was almost enough to get her off. She regarded herself speculatively in the mirror, then pulled her panties off and discarded them on the bathroom counter.

No sooner had Ali left them then Sharon made her move. She threw her arms around Dean's neck and kissed him passionately, pressing her body against his. He returned the kiss, squeezing her ass with one hand and palming one of her tits with the other. After a few heated moments of passionate kissing, she pulled away. She pushed him against the wall and sank to her knees, swiftly undoing his pants and removing his hard cock. Without a word she grasped it by the base and engulfed the head with her mouth. Stroking him swiftly, she bobbed her head back and forth, making loud sucking sounds. Dean exhaled softly and put one hand on her head, closing his eyes.

He opened them a moment later when he heard Ali come out of the bathroom. He looked at her, somewhat shamefaced. She smirked at the sight of her friend blowing him and shook her head. She watched the scene before her for a moment, rubbing her pussy with one hand. She locked eyes with Dean. Taking her hand away from her crotch, she sucked on her finger sensually. With a toss of her hair, she slinked over to where Dean stood against the wall, took his face in her hands, and kissed him passionately. As their tongues wrestled, she slid one hand down his chest to rest lightly on Sharon's head.

Sharon was thoroughly enjoying Deans' hardness in her mouth, and the smell of his arousal as she sucked him. She looked up when she felt Ali's touch. The sight of her friend kissing their guest sent a jolt of desire through her body, causing her pussy to grow wetter. She lightly drew the nails of her free hand up her inner thigh and slid a finger inside her panties. Feeling her wetness made her moan, a sound which Ali echoed seconds later as she broke the kiss with Dean.

Between one beauty sucking on his tongue and another sucking his cock, Dean's state of arousal seemed to keep growing. He smiled at Ali when she pulled away, and his heart skipped when she smiled sexily back. They looked down at Sharon, who made eye contact with both of them before pulling away from Dean's dick. It left her mouth with a loud pop, and she stood up. She pulled Ali to her and kissed her deeply. "You have got to taste his dick," she said in a low voice. Ali looked at Dean and smiled. "I intend to," she replied. Then Sharon turned and kissed Dean. Dean grabbed her in his arms, returning her kiss passionately.

Ali moaned lightly watching them French. She reached one hand to caress Dean's still hard cock. Sharon broke the kiss with Dean and turned to face Ali. Bending down slightly, she started kissing Ali's neck and chest. She slid one hand down Ali's front and back up under her dress, expressing no surprise when she discovered Ali had shed her panties. Instead she knelt down, pushed Ali's dress out of the way, and began eating out Ali's pussy.

Ali sucked in a sharp breath and put a hand on Sharon's head, holding her in place. Licking her lips, she reached with her other hand and played with her nipples through her dress. Dean walked around behind her and used both his hands to caress her breasts. His hard cock pressed against her ass as he kissed and licked her neck. She arched her back into him, her breaths coming faster as Sharon's tongue brought her close to her first orgasm.

Sharon lapped at Ali's clit and ran her tongue along her pussylips, determined to make her friend cum. She ran her nails lightly along Ali's inner thigh, a gesture that she knew drove her friend wild. She could tell from Ali's increasingly quick breathing and the tightening of her grip on Sharon's hair that Ali was getting closer and closer. Sharon slid two fingers deep in Ali's pussy as her mouth closed around her friend's clit and she sucked hard. That was enough to push Ali over the edge, and she squealed as she came.

Sharon stood up, and Ali grabbed her friend and pulled her in for a quick kiss. "Thanks," she said breathlessly. "I needed that." Then she turned around to face Dean. "What did you think?" she asked coyly. He smiled and said, "That was hot." Ali smiled impishly and took his erection in her hand, giving it a small squeeze. "Come on," she said, nodding her head in the direction of the king bed. "I still need to taste this cock." She squeezed his cock again let go, then walked to the bed, hips swaying sexily as she pulled her dress over her head.

Sharon took hold of Dean's arm. "Doesn't her ass look amazing?" Sharon whispered into his ear, giving it a lick that made him shudder. He turned to look at her with a smile. She leaned up and kissed him, pushing her tongue deep into his mouth so he could taste Ali's pussy. He growled deep in his throat. Sharon moaned lightly when he squeezed one of her breasts.

Dean pulled off his shirt and kicked off his pants, then followed Ali to the bed, pulling Sharon along by the hand. When he got to the bed, he took Ali by the shoulders and kissed her long and hard. She moaned into the kiss, her knees watering and her pussy flooding. She put her arms around his shoulders and pressed her naked body against his.

Sharon pulled her own dress over her head and dropped it to the floor. She slid a hand into her panties and toyed with her clit, watching Dean and Ali make out. She could smell both of their arousal in the air and on her skin. She pushed her panties to the ground.

Ali broke the kiss and pushed Dean down onto the bed. He slid up on the mattress, laying flat. His hard cock lay up against his belly. Ali crawled between his legs, took his manhood in her hands, and slowly lowered her face towards it. Extending her tongue, she gave a long, sensual lick from the base to the tip, then swirled her tongue around the head. Dean let out a low, throaty growl and pushed his hips up slightly. But Ali continued to tease, gently stroking him with one hand while she moved her mouth down to caress his balls.

Sharon giggled and reached out to spank Ali lightly, then crawled onto the bed and kissed Dean again. He pulled away and looked at her naked body lying on the bed next to his. "Your tits are fantastic," he breathed. She flushed with pleasure and pulled his head down, encouraging him to suck on her nipples. Dean happily complied, licking and kissing first one, then the other, making Sharon moan.

Ali, meanwhile, had ceased her teasing and was now sliding Dean's cock in and out of her mouth, stroking the shaft in time with her lips with one hand and lightly stroking his inner thigh with the other. She was so turned on by his thickness and hardness and the taste of his precum which kept spilling out. Her eyes were closed, but the sounds of Sharon's moaning made her look up. Seeing her friend's tits being ravaged by Dean made her own tits swell with desire.

After a few minutes of Dean's sucking, Sharon's nipples were taut and super sensitive. She was enjoying his ministrations, but wanted to feel his lips somewhere else. She pulled his head away from her breasts, kissed him hard and quick, then swung one leg over his body, positioning herself so he could eat her out while she watched Ali suck his cock.

Dean growled low in his throat at the sight of Sharon's neatly shaved pussy above him. He grabbed her ass roughly when she sat on his face, sliding his tongue along her pussylips. She squealed in delighted surprise, and his cock swelled in Ali's mouth. He knew he was close to cumming, and wanted to get Sharon off before Ali got him off. Kneading and squeezing her asscheeks, he fucked her pussy relentlessly with his tongue. She moaned and writhed above him, one hand holding the wall for support, the other twisting and squeezing her nipples. He lapped at her pussy, penetrating her folds with his tongue, savoring the taste of her arousal.

Ali decided that her pussy needed some direct stimulation again. She pulled her mouth off Dean's cock and she climbed up on top of him. Holding his cock in one hand, she squatted down over him and inserted him into her dripping snatch. She ground down slowly, savoring the feel of his hardness filling her pussy. With her hands on his abs, she began pistoning her body, loving how his cock felt inside her. Dean groaned deep into Sharon's pussy as Ali fucked him. She reached forward to grab Sharon's tits and pull her into a kiss. The room filled with the sounds of their arousal as the three fucked each other.

All too soon, Sharon felt her first orgasm approaching. She moaned into Ali's mouth as she rode Dean's tongue. Dean held her ass in place as he ate her out. Pulling away from Ali and breathing hard, Sharon ground her pussy on Dean's face until she came with a loud cry. The way Dean's body moved as he fucked Ali caused little aftershocks of pleasure to course through Sharon's body. After a moment she crawled off his face, which she noted with pleasure was shiny with her cum.

Seeing Dean's mouth covered with Sharon's juices, Ali leaned forward and kissed him deeply. Dean returned her kiss and moved his hands to her breasts, fondling her taut nipples. The sensation sent lightning bolts of arousal deep to her pussy, and she came again around his cock.

Sharon moved behind Ali and bent down to lick at Dean's balls. She reached up and pulled Dean's cock free of Ali's pussy and sucked it, groaning with desire at the taste of her friend's pussy. The sucking sensation was too much for Dean, who finally grunted that he was going to cum. Sharon sucked harder, moving her mouth so that only the head of Dean's cock was in it and stroking his shaft with her hand. With a loud groan, Dean released his seed in her mouth. She moaned around it as she sucked, holding the cum in her mouth.

"Don't you dare swallow," Ali commanded in a mock-serious tone. She pushed herself away from Dean and quickly turned to face Sharon. "Give me some of that," she said, pulling Sharon into a deep kiss. Sharon used her tongue to push Dean's cum into Ali's mouth, and the two of them traded it back and forth for a few seconds before swallowing. They turned to look at Dean, arms around each other's shoulders and caressing each other's tits. "I hope you're not finished for the night," Ali said in a low voice. "You still need to fuck Sharon."

Dean smiled ruefully. "I may need a second," he said.

Ali laughed lightly, then turned to look at Sharon. "Okay. I can keep her warm for you."

"I'm plenty warm," Sharon said dryly, returning her gaze. "As you can see. But I can't say no to you."

Dean moved to make room for the two of them on the king-sized bed. Ali and Sharon lay down next to him, with Sharon sandwiched between the other two. Dean reached out and caressed her thigh as Ali bent down to nuzzle Sharon's tits. Sharon shivered with pleasure and turned to give Dean a kiss. She reached down to guide Dean's hand toward her pussy, which he noted was still sopping wet. After a moment he felt a cool hand on his still semi-erect penis, which he realized was Ali's. She stroked him lightly while he continued to kiss Sharon and play with her clit. In a few minutes he was hard again. Ali released his cock, then reached up and took Sharon's hand and guided it down to him. She moaned with desire when she felt his erection. Breaking the kiss, she looked him in the eye and said, "Are you ready now?"

"Absolutely," he breathed. "How do you want me?"

"Get behind me," she answered. She positioned herself on her elbows and knees on the bed, feet hanging off the edge. Dean moved to stand behind her and beheld her round ass, with her pussy open and waiting for him. He positioned his cock at her entrance and pushed inside her slowly. They both moaned as he entered her, and Ali, watching, echoed them.

Dean put his hands on Sharon's hips and began fucking her, sliding his cock inside her and pulling it almost all the way out in long, slow, deep strokes. Ali lay on the bed, watching, legs spread and sliding two fingers of one hand in and out of her own pussy in rhythm with Dean's cock. Her other hand played with her breasts. She was so turned on watching her friend get fucked.

Sharon shivered as Dean's cock slid in and out of her. Resting her weight on one arm, she reached between her legs to rub her clit. Eyes closed, she gave in to the feeling of Dean's cock. Ali was right—it was amazing; but she wanted more. She opened her eyes and looked at Ali. "Bring that tasty cunt over here," she said.

Ali smiled. She crawled over to her friend and kissed her briefly before turning around and presenting her butt to Sharon. Spreading her legs a bit and resting on her knees, she lay her head down on the mattress to give Sharon access to her pussy.

Sharon started by reaching up with one hand and sliding her fingers along Ali's pussylips. She leaned in and inhaled her friend's arousal, and the scent made her shiver. Then she licked slowly from Ali's clit to her asshole and back down, causing her friend to moan. She licked her way up Ali's pussy again, and then briefly teased her tongue around Ali's starfish.

Ali groaned. She and Sharon had had sex before and were no stranger to pleasuring each other's pussies, but they hadn't done much anal play. At the moment, Ali briefly wondered why that was. But, she figured, tonight was definitely a night for new experiences. What was one more? With a quick backwards look and a smile of encouragement, Ali wiggled her ass in invitation.