*That* night still felt like a dream to him. Two weeks later and he could still feel her. He could feel her breath on his neck, her soft skin and supple curves, her tight grasp on his swollen cock. He never had an encounter like that. Two weeks passed and he was still thinking of her when he masturbated. She had consumed his desires, and now all he could do was think of her. Think of *that night.*
…
He was young, single, and very mobile. He had a thick mop of dirty blonde hair which he kept neat and combed back. He was tall and lean, a result of many winters on his collegiate wrestling team. His chest sported a thick bush of hair which was black over his slightly tanned skin. College brought a course auburn beard to his face. His right arm was slowly being covered with tattoos. He often traveled for his work, and often fantasized of hooking up on the fly with a stranger. He had a girlfriend or two in college, with whom he had solid relationships and great sex with, but non the less were lacking. What he really needed, what he had fantasized about the longest, was an older woman. A woman with experience who knew what they wanted and took it when they saw it. A woman that we see through his façade and understand what to do with his fantasies. He had come close with an old professor, but out of mutual respect and professionalism it never went further than a few risky text messages. A mere sampling in the face of his unrelenting desire.
The opportunity continued to elude him until tonight. His flight landed late, and when he arrived at his hotel, he was relieved. The flight had not been the best, and it was raining steadily when he landed in Seattle. His ride downtown to his hotel was quiet. He was thankful for that. He was in Seattle for a big presentation, one which would help him with a promotion. This was his first chance at a promotion, and he was nervous. He rested his head on the car’s window and let his thoughts drift off. He went over his presentation notes, and with that brought a new wave of anxiety. *I’ll grab a drink at the bar.* He thought. That would calm his nerves. However, deep down he knew what he really wanted. What he really needed.
The hotel was grandiose and inviting. He quickly checked in and went up to his room. The room was modest but sported a grand view of the city. He plugged his phone in on the nightstand by his bed and went to shower. His bathroom had a spacious standing shower with a generous hot water supply. He turned on the shower and let the steam slowly fill the bathroom. He removed his clothes, a simple business causal ensemble, folded them, and placed them on the sink counter. He stepped into the shower and let the hot water flow down over him. He washed himself. He lathered his body with soap, taking big relaxing breaths as he went. He closed his eyes and gently moved his hands over his chest, pausing at his nipples. He gave each of them a slight pinch and then rubbed them gently with his thumbs. This made his cock twinge and he slowly slid his right hand down to meet it. He ran his hands through his other bush, he sported his pubic hair proudly. He gripped his shaft and felt his flaccid cock begin to bulge. His thoughts drifted away from work. The hot water felt soothing, and soon he was stroking his fully erect cock. He leaned slightly forward and ran his other hand down his back. He slowly ran a finger between his cheeks and teased his hole. He pressed gently until his fingertip was inside him. His other hand stroked his cock faster and worked his finger on the other end. With each stroke his finger went a little deeper inside himself. He moaned softly as he got closer to the edge. He got himself as close as he could get to orgasm and then stopped.
He stood there breathing heavily and let the cooling shower water work its magic on his cock. His erection slowly receded as he turned the shower off, stepped out and dried himself. He loved to edge himself. He loved the intense build up and the slow come down. He loved the feeling of blue balls and denying himself an orgasm. It made him feel sexy and in control. He brushed his teeth and freshened himself up before leaving the bathroom. He opened his travel suitcase on the ground, put his old clothes in a bag, and set out a fresh outfit. He then produced a smaller black bag. Inside were two items: a small bottle of lube and a butt plug. The plug was about five inches in length. It had a circular faux jeweled base and was a slim conical shape. He squeezed out some lube on his fingertip, bent over, and ran his finger around and then inside his hole. He then squeezed a generous amount of lube on the plug, bent over again, and slowly worked the plug into himself. He pushed the plug until he was completely full and his ass gripped the base of the plug snugly.
He loved being plugged up. He took a few deep breaths to calm himself (and his cock) and continued to get ready. He loved his slutty little secrets. He pulled on a pair of briefs which showed off his bulge and kept the plug in place. He thought that if he was unsuccessful in finding a lover tonight, he would at least make himself cum hard.
It was late, but well before last call. He put on his more casual clothing, a well-fitting pair of jeans and a flannel button up shirt. His jeans hugged his muscular thighs and showed off his ass nicely. The flannel hung loose over his upper torso, and his rolled-up sleeves gripped around his bi-ceps. He stuck a room card in his wallet, grabbed that and his phone and set out for the lobby.
The hotel bar was empty and quiet. He took a seat at the bar (secretly being reminded of his current filled up state as he did) and ordered a whisky neat. He took a gander around the bar and saw a few patrons, but the dampened lighting added a shroud of mystery to the place. He stoically sipped his drink and was just about to pull out his phone when it happened. More like when *She* happened. He felt as if her presence filled up the entire room as she passed through the entrance of the bar. He caught a quick initial glance, red hair in a short pixie cut and a business casual outfit much like the one he wore on the flight earlier. Before they could lock eyes he quickly looked down and only heard the sound of her heels grow and then fade as she passed behind him. He pretended to scroll through is phone, and when he finally had to courage to look up, he noticed that she was only a few seats away at the bar.
He continued to sip on his drink and fake scroll through his phone all while attempting to sneak more looks at her. Her voice was direct when ordering and then pleasant as she laughed at some comment the bar tender made. Her blazer was draped over her chair, she sat back into the chair after ordering her drink and revealed more of herself. Her collar was unbuttoned just above her breasts, showing slight cleavage. Her blouse fit tightly around her torso and chest. She had creamy pale skin, supple red lips, and piercing green eyes. Her short hair was kept up in a faux hawk, and she oozed confidence. He had to guess but felt that she had to be at least ten years older than him. He couldn’t put a finger on it, but she carried herself with a certain confidence that only comes with experience.
The bar tender placed her drink in front of her and she thanked him again. It was a glass of wine, something red and full bodied. *A perfect match* he thought. He felt his ass grip the plug and his bulge tighten in his briefs. He shifted in his seat (teasing the plug again) when it happened. Just as she brought her glass to her lips, they locked eyes. Just for a moment. He felt his face flush and he quickly looked away. *Now you’ve gone a ruined it* He thought. He looked up again and caught her stare once more. Her green eyes were pensive, and a little smirk formed on her lips. He could not believe what happened next, it felt like everything was in slow motion.
He watched her pick up her drink and get out of her seat. This revealed the bottom half of her. Her breasts protruded further out as she straightened up, and he was able to take in her entire frame. She was tall, even without the heels on. Her frame was thicker, not overly athletic but *powerful*. Her dress pants gripped her waist and legs all the way down to her ankles. Her heels were black and professional. She slung her blazer over her shoulder and made her way towards his section of the bar. He felt as if he was swimming in her every movement. Her breasts and hips bounced slightly as she walked. The sharp click of her heels grew louder with each step. Her green eyes locked with his and he was entranced, unable to do anything more than bask in her aura.
“You don’t see very many men these days rock a full bush like that these days” She chided.
His tongue was in knots, and he was unable to speak. He just looked her, taken aback that she acknowledged him at all.
She pointed to her chin. “You’re beard, its quite impressive. Is this spot taken?” She motioned to the chair on his right.
“Its all yours.” He finally managed to say. Her scent was intoxicating, but it didn’t smell like any perfume he had experienced before. In fact, he couldn’t place her scent anywhere in the dictionary of his ole factory. She placed her blazer over the chair before she sat down, and he caught the slightest bit of perspiration around her armpits. This small detail drove him wild on the inside. He took another sip of his drink and placed the empty glass on the bar.
“Looks like you need to be filled up.” She said, and he almost spit his drink out.
“Huh?” he leaked out.
She pointed to his drink. “Whisky neat?” She motioned to the bar tender. She used that same direct tone when ordering, only fueling the fire inside of him. She let out a sigh and sipped on her wine. “You know I think you were on my flight earlier.” She said. “You were the unfortunate one stuck next to that rather large fellow in the emergency exit row?”
“Hah! Yes I was.” He eased into himself a little more, the whisky was working some confidence back into him. “It wasn’t the worst, but I am glad to be off that flight.” His next drink arrived.
“What brings you to Seattle on a rainy fall Wednesday night?” she asked, her pensive green eyes taking him in. He was aware that she had positioned herself a little closer to him than a normal causal conversation would permit.
“Work actually.” He said. His confidence was coming back, he sat up and reminded himself again of his plug. He twitched ever so slightly, and he knew that she caught it. “I have this huge presentation tomorrow, and it could really help me secure a promotion.” He locked eyes with her and smiled. “but I feel really under prepared. I’ve been traveling for work all month and I’ve felt like I’ve spent zero time on it.” He continued.
She took another drink of wine. “I’m sure you’ll do just fine, if you have the confidence to rock that face bush, then I bet you can conquer just about anything.” She smiled. “Do you travel for work often?” With this he caught the slightest taste of her wine on her breath. It took a serious effort to keep himself under control.
As his whiskey worked its way through is system, he continued to converse with her. They swapped travel horror stories. He found that she was very easy to talk to. She ordered one more drink for each of them and they continued to converse with ease. Her wine appeared to be working on her as well, as she eased back into her chair and slung an arm around the back of the chair to better face him. Somehow her blouse seemed more open that he first noticed, her breasts seemed to pull him in.
The bar tender broke this magic when he announced last call. They finished up their drinks and it all appeared to be ending. She had made a few jests at his posture during their conversation. Only now had he become aware of his posture as she made another jest. He chided about how sitting like this helped ease his back after the cramped flight. She accepted the answer. Only he knew the truth, that he had to sit up straight when he had his ass plugged.
Then she leaned in extra close and whispered in his ear. Her breath was hot, a mix of sweet and sour that filled up his nose.
“I know how little sluts sit when they’re all filled up.” She whispered bluntly. He was caught. “Why don’t we go to my room, and you can show me just how much of a little slut you are.”
All he could do was agree. She paid their tab and got up. He followed her out into the lobby, drinking in her powerful figure as she walked, her pants hugged her ass which bounced firmly. They stepped into the elevator and when the doors slid shut, she ordered her next command. It was the same voice she used at the bar. Direct and powerful. “Unzip your pants and pull out your cock for me.”
He did as he was told. His cock was flaccid, he was too charged up to mount an erection. She reached over and cupped his cock and balls with her hand. Her nails gave a sharp edge to her grip. Her hot breath was in his ear again. “Do you know how to use this *little* thing?” She asked. He could only nod. She unbuttoned her blouse a little more, showing him another tease of cleavage. They reached her floor and she stepped out first, still cupping his cock and balls. “No need to put these away” she said as she led him to her room.
Her room was like his, with a better view of the city. He stood in the entry way, feeling a little silly and very horny. She tossed her blazer and turned back around the face him. “Now that I’ve seen yours.” She teased. She slowly began to unbutton her blouse, she let it fall to her elbows revealing the black lacey bra which was holding back her breasts. She maneuvered her hands behind her, and the bra dropped off, finally revealing her breasts. He felt his cock begin to rise as he stared at her breasts. They were somewhere between a C and D cup and stood firmly on their own. Her pink areolas were medium sized circles around her nipples. She continued to gaze at him as she moved her hands down and unzipped her pants. With a little effort she lowered her pants until the dropped at her ankles leaving only a black thong. It barely covered her pubic hair, which was exceptionally curvy and strawberry blonde.
She laughed. “You’re not the only one rocking full bush.” She dropped her panties as well. She was now only in her blouse, which she brough back up around her shoulders and left it unbuttoned. Her nipples poked through the white shirt. He could now take in the true beauty of her curves. Just like him, the athletic build that she once sported had faded just slightly as time and age marched along. If she was nearer to his age, then he would have labeled her as “thicc”, but the only descriptor that came to his head now was *powerful*. She stood there a while longer fully nude in front of him, without the heels she was still a good head taller than him. “Your turn” She said.
As she sat down on the edge of the bed, he removed the rest of his clothes. He got down to his briefs before she stopped him. She had spread her legs open and was sitting back. Her pussy was now fully exposed. “Now I want you to turn around and slowly take off those briefs.” She said in the same direct tone from the bar. He stepped closer to her and did what he was told. “Now bend over and show me your little secret.” He spread his cheeks and revealed the faux gem base of the plug. “Oh that is so adorable!” She exclaimed. She reached forward and grabbed the base. He kept his cheeks spread and she teased the base back and forth.
He let out a moan, he could not contain it anymore. “Do you enjoy being a plugged up slut?” She asked.
“Yes.” He moaned. “I love it.” He could hear that she was wet as she moved her fingers across her pussy. She was still playing with his plug when she reached around and stuck her fingers in his mouth. He could taste her wetness. She then wrapped the same hand around his cock, which was swelling full of blood and growing harder with each stroke. All in one movement she stood up and leaned him forward, he put his hands out and placed them on the dresser in front of the bed.
She was behind him and all around him at the same time. He could feel her breasts against his back and her hot, heady breath was on him again. “Are you going to be a good little slut for me?” She asked.
“Yes.” He moaned. She slowly pulled out the plug. He moaned louder. She teased the plug back in, which is hole accepted willingly. Her other hand released his cock and slowly worked up his chest, her fingers ran through his chest hair and pinched one of his nipples. She continued this slow tease and pushed on his back until he was fully bent over the dresser. She worked the plug in and out with one hand and caressed his body with the other. He was moaning, out loud, louder than he wanted to admit. He was in total bliss, seduced by this older woman, and he was all hers.
She spanked his ass and turned him around. She led his face to her left breast, which he took in one hand and placed his mouth over. Her breasts where natural and firm, and he began to suck, working his tongue around her areola and biting down delicately on her nipple. She moaned now too and led his other hand down to her pussy. She was soaked. He gently worked his way through her lips and found her clit. She held him there for only a moment, moaning as he worked. Keeping breast in hand, he looked up at her. There eyes locked and he leaned in. Their lips and tongues danced, and he continued to taste that hot, wine laden breath. It was intoxicating. Her breathing began to rise, and she brought him in closer, wrapping her arms around his shoulders and neck. “Don’t stop.” She said bluntly. She grabbed the hand that was in between her thighs and motioned for him to work faster on her clit. His cock was so hard that it was poking into her hip. She squeezed him tighter and her breath became sharp, husky gasps. “Oh fuck, just like that.” She whispered. “I’m.. going… to.. CUM.” She let out one more heavy sigh and released her grasp.
He could feel the perspiration form on her body. When they separated, she was smiling and glowing. She ran a hand through her short hair and gripped his cock with the other. “My turn.” She said. She led him to the bed. “Lay down.” He laid down on the bed, his erect cock defied gravity and was standing straight up. His tip glinted with pre-cum. She stood over him at the edge of the bed. Her breast, curves, and bush towered over him. She bent down and began to work his cock with her mouth. He tried to place a hand on her head but was quickly denied. “No touching.” She chided. He laid there in ecstasy while her warm mouth slid up and down his shaft, her hand working up his chest to find his nipples. They were playfully pinched. She brought him just to the edge as he had done to himself earlier in the shower. Then she stopped. He let out a playful moan. “Just wait.” She said. And she left him like that. He watched her walk over to the bathroom. “Just a sec!” she said. He laid there, smelling her pussy on his fingers and gripping his own cock.
She returned, much to his surprise, sporting a strap-on and holding a bottle of lube. The harness hugged her hips snugly and the dildo was of medium length and girth. She approached the bed and kneeled, *her* cock was now in his face. Without saying anything, he gripped the dildo and began to work on it with his mouth. “Yes, take it all in my little cock slut.” She said as she squeezed some lube onto her finger. She worked her hand back and slowly stuck her finger in his hole, which was still loose from the plug. Her finger slipped right in. She massaged his prostate while he worked on her cock. He took it in as far as it could go, worked it back and forth until it was covered in drool.
“You’re so hard, you love sucking my cock don’t you?” She asked. Mouth full of cock, he muffled in agreement. She retreated after one last deep throat. They locked eyes and he knew. Finally, it was time, he was finally going to be the slut he always knew he could be. He lifted his legs up and fully produced his asshole to her. She slid over on her knees until they met in missionary position. She poured a healthy amount of lube on her cock, first teasing the rim of his hole, and then pressing firmly but slowly, worked her cock inside of him.
“Oh fuck.” He moaned. “Oh fuck. I am so full.” She leaned over and kissed him passionately. Her hips moved back and forth, working her cock in deeper. He tasted her breath and smelled her aroma. She smelled so sweet, with the tiniest hint of salty body odor. They released their passionate embrace, and she leaned back. While still sliding in and out of him, she gripped his cock. It throbbed in her hand and he squirmed, helplessly in her grasp.
“Do you want to cum now?” she asked. While he did not want this moment to end, he was eager for release.
“Yes.” He moaned.
“Then beg for it.” She demanded.
He whispered please as she stroked his cock and milked his prostate with her cock.
“I’m so close.” He moaned. She thrust herself deep and held it there while she stroked his cock faster. She leaned in as much as she could.
“Cum for me.” She commanded.
And he did. He finally released, his body tightening up and releasing as he ejaculated. His warm cum spilled out on her hand and over his chest. He was covered. She chuckled, bent over and kissed him. She slowly pulled her cock out, and then crashed onto the bed beside him. Eventually they both got up and went to shower. It was late, and he was feeling completely exhausted.
She stood behind him in the shower, rubbing his shoulders. “Feel more relaxed now?” she said.
“Definitely.” He said. “That was incredible, I’ve never done that before.” He felt like a new person, his confidence felt renewed.
“Well I don’t think we’re quite done yet.” She said. She pushed him down gently and he went to his knees. She leaned against the shower wall and guided his face to her pussy. It was still wet, and not just from the shower. He grabbed her hips with his hands and pushed his face into her bush. He kissed gently around her pubic area and worked towards her pussy, all while she ran her hands through his hair. She gently pushed his face into her pussy as he began to lick and suck on her clit. He reached up with his right hand and grabbed her breast, giving it a hard squeeze.
As he licked and sucked, she continued to push on his face and gyrate her hips. She was grinding her pussy on his face now. She began to moan and he could feel her fresh juices gushing onto his face. She tasted amazing. He felt his cock begin to swell with another erection, however he paid no attention to it, all he needed was in front of him. He focused his attention on her clit, first sucking, then sticking his tongue out to let her grind on.
She suddenly pushed him away. “I need that cock, now.” Her direct tone was back. He stood up, they were still in the shower and the hot water was fading.
“Should we go back to the bed?” He asked. She didn’t respond, she only turned around and stuck her ass out at him.
“I want you to fuck me right now.” She stated. He obliged. He guided his cock into her pussy as she pushed back on him. She was so wet, and his cock slid right in. Her pussy was warm and tight. It gripped his cock as he thrusted in and out of her. He reached around again with his right arm and grabbed onto her breast. Her moans grew as he continued to thrust. She pushed back on his cock, eager to take it all in.
“Fuck right there, don’t stop.” She said. ‘Don’t stop, don’t stop, don’t stop!” He continued to thrust as she let out a mighty orgasm. Her pussy gripped his cock tight and he felt her warm cum around his shaft. He gave a final thrust, pulled his cock out and ejaculated all over her backside. He had never came twice like this before.
She turned around and kissed him deeply. “Wow.” She said. “I think I’m going to keep you.”
The shower was cold by now, so they both stepped out and toweled off. She put on a robe as he put his clothes back on. She wrote something down on a piece of stationary and handed it to him.
“Let’s meet again sometime, my little slut.” She kissed him and saw him out the door.
He returned to his hotel and crashed.
…
Two weeks passed. The presentation came and went. He received the promotion with flying colors. However, none of that seemed to matter. All he wanted was her. Another week went by, and he was almost convinced that it was all some sort of sexually charged dream. As luck had it, he needed to return to Seattle towards the end of the year. He texted her. No reply. The flight came, no reply. He landed in Seattle, no reply. Just as he was about to give up hope, his phone pinged.
*Room 315 at the Waldorf*. It read. *I hope my little slut knows what to wear.*