Lindy was not quite ready for bed. She decided to stop into her hotel’s bar for a drink or two. Lindy was in town for her high school best friends wedding. She was one of the attendants, and the wedding party had finished the rehearsal dinner, and decided to go out together as a “last night of freedom” bash. Her friend could get pretty crazy, and knew that Lindy’s job was such that she couldn’t exactly be photographed participating. Susie told Lindy to go get beauty sleep, that they’d likely need someone to be the sane voice of reason. Lindy laughed and thanked Susie and her friends for understanding. Susie’s friend Beth promised to save a “penis straw” for Lindy.
As Lindy took her seat she noticed a man sitting at the bar in a suit. He was attractive, with gray hair and glasses. She pegged him to be about 15 years older than her. Lindy ordered her glass of Malbec, and sipped it slowly. Chatting with the gal behind the bar. Soon, she was aware of the man. He asked if he could sit next to her. She agreed. As he took his seat, she sensed a duality of confidence and shyness that was intriguing.
The man introduced himself as Douglas, Lindy shook his hand and said, Melinda, but most call me Lindy. Douglas explained that he wasn’t in the habit of accosting single women in hotel bars, but Lindy had him intrigued. “You are wearing a very nice little black dress, Stella by Stella McCartney, and you’re sitting alone. Either you’ve had the worst first date ever, or there’s a story here”.
Lindy laughed. Something about his manner was very appealing. He was humorous, but also he put her at ease. “Well, I’m in my high school best friend’s wedding. They just had the rehearsal dinner and are having a combined last night of freedom. My friend can get pretty crazy, and my job is such that I can’t risk having those photos online”.
“Ah, I see. Does this mean you never get into crazy activities, or does this mean you’re just not photographed?”, Douglas looked at her. He wasn’t sure what overtook him. He normally would never approach a woman like Lindy. Hell, he was usually set up on dates. Douglas was confident about many things, but not about women. He was locally considered a catch, but most women only saw his bank account, not the real Douglas. The real Douglas was a voracious reader, and wanted an intelligent woman, not just a good looking one. However, Lindy was quite beautiful. Also, quite Celtic looking which was right up Douglas’s alley.
Her deep blue eyes sparkled, and her dark brown hair was quite curly. She had freckles, and he loved that. His question made her laugh. Douglas quickly apologized if he was being cheeky.
Lindy was quite attracted to Douglas. It was clear he was in good shape. He also had very light aftershave on. His outfit was well made, but not trendy or “the” designer. She replied she liked his cheek, what she saw of it. And that it depended on how one defined crazy if she got into such activities. She then demurred that she liked her activities to be behind closed doors. With that Douglas’s eyes lit up. Lindy couldn’t quite believe she was flirting so outrageously with Douglas, but he was funny, smart, attractive, and from what she could tell had a nice body.
Douglas laughed as she replied but wondered if she was flirting with him as he thought. When she moved to turn more towards him, her leg slowly brushed his. Oh, she was flirting alright. He wondered just what sort of bra and panties were on under her very appropriate little black dress. It had been a long time since he had indulged his physical desires.
Lindy’s breasts were healthy, if he had to guess, easily a c cup, natural. She noticed his gaze. Lindy soon found herself leaning towards him to show off her breasts more. Douglas was ready to see just what she was up for.
Lindy then asked what he was doing at the hotel. He explained that it was a community charity function he was active in, and as the head, he got a hotel room for the night. He was very adamant about not drinking and driving. As the hotel manager went to high school with his daughter, he made sure that Douglas had the honeymoon suite as it was not in use. “I even have a complimentary bottle of champagne at my beck and call” he explained, “but no one to drink it with”, he said with a laugh.
Lindy decided to test the waters herself. “Funny, my favorite wine is champagne”, she shot back.
Douglas took her hand. “Well, why don’t we go indulge?” Douglas indicated to the bar tender to send up the complimentary bottle but while Lindy was distracted, he slipped the bartender some extra money and asked her to send up a better bottle. If he was going to seduce Lindy, he was going to play the part.
When they got up to the room, it was very tastefully furnished. Before they really had a chance to get settled, room service brought the champagne. Lindy and Douglas were standing close. He popped the cork and poured them each a glass. It was then that Lindy stopped him. “Look, I’m not the usual pick a guy up in a bar type, and if my instinct is right, you don’t normally bring ladies up to an expensive room with champagne, but both of us are enjoying this fantasy. I want to enjoy the fantasy, but honestly, it’s YOU Douglas, that is making me want to do this”.
Douglas looked at her. “Lindy, thank you. I’m not suave, nor am I a complete dork as they say, but I noticed you the minute you walked in. I knew I wanted to talk to you, but I had no idea where that would lead, not that I’m complaining”.
“Douglas, I want you to be direct. Something tells me you are very direct in your business life, not so much in your personal life. So, my fantasy is, you tell me exactly what you want”. Lindy knew he wanted her, but oh how she wanted him as well. She wanted him to be direct, confident. Lindy liked this guy, and was pretty sure he liked her, more than just wanting to bed her.
“Well, I want to enjoy champagne with you as we make out, and if it’s not uncomfortable, I’d like to have you sitting on my lap as I kiss you and then find out just what you are wearing under that little black dress. Lastly, I’d like to remove those garments from you, and enjoy every covered up part of your body, until you are well sated”.
Lindy gulped. His forthrightness was amazing. She was really turned on. His subtle peeks at her breasts turned her on, and by now her nipples were straining against the fabric of her dress. She noticed a definite bulge in his pants. If that were any indication, she was in for a good time. She moved closer to Douglas.
Douglas sat on the settee, and pulled her onto his lap. “Am I being appropriately seductive enough Lindy”, Douglas asked.
“Oh yes, can’t you tell”, she whispered. His hand slowly cupped a breast, and he ran his palm against her nipple.
“Yes, I believe I can”, he said. He was kissing her tenderly, and sweetly, which made his confidence, feigned or not that much more enjoyable. It was this mix of bravura and tenderness that had her wanting to be everything he wanted in that moment.
“So, Douglas, if we’re role playing, what should I be”, she asked.
“Well, as much as I could come up with some scenarios, I’m rather liking you having the freedom to be uninhibited, where there are no cameras, no corporate overlords to worry about. So, without that pressure, what do YOU want to be”, he asked.
She moaned, as he flicked his tongue across her earlobe. “I want to be had by you. I want to feel like you are seducing me, as much as I’m seducing you. I want us to do it as many times as we want, and I don’t even care if I’m tired for the wedding tomorrow. It’s been so long for me. I need to feel a man, and to be had properly by a man”, Lindy sighed.
With that Douglas put a hand in her hair and met her lips with a crushing kiss. It was passionate. He wasn’t one to sleep around casually. But this woman, with her ripe breasts, curvy hips was wanting him. It was even more arousing that she was needing this release too. That her life seemed to be as bound by rules as his. He had the strap of her dress down her shoulder, and was massaging her breast. It felt oh so good in his hand, and by her squirming, he could tell he hadn’t lost his touch. “Is this the sort of shenanigans you want Lindy”, he said huskily.
“Yes, Douglas, oh yes”, she moaned. His lips returned to hers, and his tongue took possession of her mouth. He knew how to kiss a woman, and Lindy matched his intensity. Soon, he had unzipped her dress so that both shoulders were off, revealing a very sexy, lacy bra. Douglas moaned when he saw that.
Now both hands were on her breasts, groping, massaging, kneading. He was aware of her grinding against him. He then noticed she had his jacket off, and his tie as well. She was unbuttoning his shirt, and had it out of his pants completely, and she was shoving his shirt off. God how she wanted him. He knew exactly what got her off, and oh was he hard underneath her.
“Lindy, I want you to remove your bra…you did say you wanted me to be direct, well, I want you to remove it slowly, making eye contact with me, as you watch me think of all the things I want to do to those lovely breasts of yours”.
Lindy shuddered. That was probably the hottest thing a guy had said, and he wasn’t even using slang terms. She slowly unhooked the back, and then a hand moved around front to keep both cups firmly on her full breasts. They were so close, so Lindy arched back a bit so she could better see Douglas’s face. He grinned as that pushed her mound further into his aching bulge. Lindy blushed when she realized but could not help but grind just slightly to let him know she was hot and wet.
“Now, Lindy, I’m going to have to remove these pants so that they are not still wet tomorrow” he teased. “Someone is awfully wet and going to soak my trousers”.
“Well, I can’t help what reaction you’ve produced”, Still holding onto her bra, she raised up a little so that he could slide his pants down. Soon, before he could protest, she used her other hand to push down his boxers. She wanted to see him. He was full and hard. His length was average, but his girth was on the larger side. She could not wait to feel him filling her. With that he lowered himself down. It was clear Douglas had not been treated like a sexy man in a long time. That surprised Lindy, as clearly he had that side to him.
She pressed back against him, and soon realized he had take advantage of her distraction to raise her dress up. Now it was just a thin piece of silky fabric between his hardness and her oh so wet, hot opening. She instinctively rubbed against him.
“Mmm, there’s time for that Lindy, but now, weren’t you removing something for me”, he teased her again.
Lindy arched again, and now slowly removed one strap then the other. Her hand cupping both breasts was the only thing keeping her bra on. Douglas was ready to have her then and there. Sensing that, Lindy reached for her purse, and in doing so, the bra fell off. “Oh yes, very lovely”, Douglas murmured.
His hands began their work again, as Lindy quickly put a condom on Douglas’s straining member. Lindy was wondering if she should remove her panties, when Douglas’s hand stopped her. “Have you ever been had with them on? Has a man ever wanted you so much that he didn’t even want to take the time to remove them?”, Douglas whispered into her ear. As he did so, his hand was rubbing her through her panties. She was soaking wet. His fingers moved aside the crotch of her panties and began rubbing her juices all around. He then put two fingers into her, and wiggled them, bringing out her juices which he rubbed onto his member.
“How do you not have women every night, Douglas, truly”, she gasped. “You…now…please”, she could barely talk.
“Ah, I’m not usually this suave, Lindy, you must be bringing it out in me, but yes, I think it’s time”, he agreed. He kept her panties pushed to the side, as he slid his thick manhood into her. This rubbed her panties against her clit, and she moaned. Douglas smiled as he pulled the panties tighter, causing more friction. Lindy began to rotate in circles, enjoying the feeling of being so filled. She didn’t want to go up and down just yet.
Her rhythmic circles prompted a “Yes, oh yes Lindy” from Douglas. He was right, the panties created the most teasing sensation. She continued to circle and his mouth found a willing breast. As she got more turned on, his hand found her clit and worked it through the panties. The combination of the fabric and his pressure soon had Lindy coming. She moaned his name into his neck. Douglas began to thrust into Lindy, and she cried out. Douglas wanted her panties off, but hated to pull out. Lindy was so turned on, she wanted them off too. In a moment Douglas realized that they were close to ripping, he didn’t want to damage them, and let Lindy know. With a wicked grin, she asked if he had ever wanted to rip a pair of panties off of a woman.
Indeed, Douglas had had that fantasy before, but…now? Lindy flicked her tongue on his nipple and bit down ever so slightly. She pulled back and arched her back, so that her panties were really straining. Damn, Douglas thought, how did he ever have the good graces to run into her. Soon, he realized tearing her panties off was as much a turn on for her as for him. He squeezed a breast as he grabbed a hold of the panties with his other hand, he was bringing it as tight against her clit as he could. Lindy shuddered. He then pulled and could hear the rip of the fabric. Lindy moaned loudly and that was all the encouragement he needed.
Her panties were soon ripped in the center. He stopped and Lindy shook her head no. The thin string that held each side on her hip was sure to break as well. She put his hand on her hip. Douglas then broke the string and soon had her panties in his hand. She arched her back again, as this really turned her on. Douglas couldn’t help himself, he began bucking hard into her. Her cries and pulling his face into her breasts indicated this was the right choice. She was answering his bucks just as forcefully. Soon, Douglas was coming hard. His hand found her clit and he masterfully worked her until she came again.
Lindy collapsed against him. He removed her dress, and had her completely naked. His hands still exploring her body. He suggested taking the wine and moving to the bed. Lindy helped him fully remove his clothes. His body was in good shape. They drank wine, and talked more. Lindy was still pretty wet, and rather turned on. She suggested that he could be her guest at the wedding, and perhaps help remove the attendant’s dress later on. He grinned at that suggestion and readily agreed. She let him know she wasn’t needed until 11:00. Douglas said that was good as it gave them time for room service breakfast and perhaps another interlude. Douglas then took her glass of wine and with his set it on the bedside table.
He thanked Lindy for being so open and willing a bed partner. He inquired how many condoms she had in her purse, and she said five more. He grinned and said he’d be sure to get more while she was at the wedding ceremony. Lindy gasped at the delicious thought of being had by him five more times. Douglas then kissed his way down her body and began to lick her wet willing center. She shuddered as he sucked on her clit. How on earth did she get so lucky. Not going out with her friend was the best decision. He ate her out while she climaxed two more times, and soon was ready for more action.
Douglas walked over and grabbed another condom. He put it on, and was aware that Lindy was watching. He enjoyed her attention. This evening had easily given him back several years of his life. He needed to have a woman, and Lindy was quite enjoyable to have. He noticed that in her carnal haze, she was fingering herself. He decided to sit in a chair and watch. Lindy was so emboldened by the no one will know ethos of the evening, she was working herself into another climax. She continued to do so as she reached for the champagne glass. She sipped on it. Douglas was well aware this side of Lindy was rarely seen, and he was damn thankful to be the one to see it.
He strode over and took the glass from her. Soon, he pulled her down so she was on her back, he positioned himself between her legs, and thrust into her opening. Lindy cried out his name softly. Douglas was using long, assured strokes pumping her body and watching her breasts jiggle with each stroke. He kissed Lindy hard on the mouth. She looked at him. Completely out of character, but completely in the spirit of the evening Lindy bluntly told him what she wanted when Douglas asked what she’d like.
Douglas didn’t think he could get harder, but when Lindy was explicit, his member jolted upright. He soon complied and was thrusting hard into Lindy who was rolling her head back and forth in a state of arousal. She was not speaking now, just grunting. Douglas firmly grabbed a breast and began kneading it as he sensed she was close to a hard climax.
He was right. Lindy shuddered and moaned as she came hard, her muscles gripping him and milking him. That was all it took for him to follow. They lay naked together, he apologizing for not having night clothes for either of them. Lindy purred that she liked the idea of sleeping naked with him, as that was another thing she had never done.
In the morning, they took advantage of Douglas’s morning state, and then ordered room service. Both had on robes, and enjoyed the breakfast. Lindy then removed the robe,and went to take a shower. The sight of her naked had Douglas surprisingly ready for action again. He was hesitant until Lindy called for him to join her. They agreed to meet later before the reception. Douglas wasn’t sure what was ahead, but was certainly eager to find out…