Andee’s Sexual Adventures Continue in Chicago

Andee tossed her purse onto the hotel bed and dropped her suitcase onto the rack tucked away in the closet. She had one last stop – this time Chicago – before heading back home.

She hadn’t really had the chance to discuss everything that occurred in Denver with her husband, other than to allude how a certain fantasy of hers had become a reality. Of course, there is only so much fun and excitement to be had via webcamming with someone halfway across the continent; even less so when you long for the physical intimacy when describing the events of the night in question.

Given that she had permission to continue on her sexual adventure, she wasn’t worried about any consequences when she got home from her road trip – well, other than a rather sore vagina from the repeated sexual pounding she knew she would get the minute she walked in the door; not like she wasn’t still feeling a bit used from her wild night in the Mile High City just a three days previous. She figured it would easily be a couple weeks before she entertained any idea of anal sex.

Her feet hurt from the long day … and her pussy was only now beginning to feel its sexy old self. It didn’t help that after her encounter with the guys back in Denver she had masturbated several times over the following two days; and once for good measure before leaving to catch her flight to where she found herself now.

She plugged in her laptop and flipped on her camming account, waiting to see if her husband would be logging in as arranged. They spent a few minutes chatting, before she said she was going to have a quick shower and then hit some of the stores along Michigan Ave. Outside of a handful of the key sessions, this was the one thing she was really looking forward to in the city.

The first day of the conference was relatively uneventful and fairly predictable. Andee met a few new people including a charming man named Don. She learned he was staying in the same hotel – well, as were others – and would be presenting at the one session she had specifically come to Chicago for.

Innocently enough, she invited Don to join her for dinner so she could pick his brain about the seminar subject beforehand. On the elevator ride up from the hotel lobby, Don agreed and said he would drop by Andee’s room and pick her up before they headed out to a restaurant that he had been told about and was eager to visit.

When she got to her room, she logged onto her computer again to catch up with her husband. It had been almost two weeks since she had been home and, despite the wild romp with the three guys in Denver, she was feeling exceptionally horny.

“I’m going out for dinner with one of the presenters, but when I get back I want some serious Skype sex,” she typed to him.

Andee gave her husband a quick update on the dinner plans she had made – repeatedly stating that this time around things were nothing more than professional. He teased her about making such claims, knowing full well that his wife had an adventurous and flirtatious streak a mile wide.

She was still typing away her defence to his claim when she heard Don knock at her door. She angled the computer so that it wouldn’t be too obvious that she was in the middle of a conversation with her husband and went to let her friend in.

Andee was impressed with what she saw when she opened the door. Don, who she figured was edging close to 50, was quite built. It was obvious that he spent a good amount of time in the gym. He was wearing a black leather blazer and had changed into a nicely fitting blue dress shirt and matching tie. She, on the other hand, was still in the clothes she had worn throughout the day and felt just a little under-dressed as compared to him.

“Sorry, I kind of lost track of the time. I’m just finishing up something really quick,” she said, inviting Don in to wait. “Won’t be a minute.”

“We have time, so no need to rush. Been shopping on Michigan Ave., I see,” Don said, giving a nod to the parcels on the chair as he followed her into the room.

“How can you not?” Andee laughed, grabbing some of them so her conference mate had a place to sit.

“I’m always amazed at how they give you the largest bag for the tiniest items,” he added, holding up the Victoria’s Secret bag she had missed in her initial swipe.

Andee blushed, and grabbed it from his hands. She didn’t mind him being so familiar, but she wasn’t so sure she really wanted him to know exactly what was wrapped up in the tissue in the bag – or how true his comment was about tiny items.

Don laughed at her girlish embarrassment. “Maybe I should get you to take me there later. Bringing something home might score me some serious points with my wife.”

“I know my husband appreciates it,’ she replied, ensuring Don knew she was married. “Let’s see how dinner goes. If we have the time we can stop in and I might be able to offer some advice for something nice. Where are we going?”

“It’s a little Italian place that someone recommended to me. Apparently the atmosphere is great and the food is amazing,” he said. “I figured it would be the kind of place to enjoy a glass of wine and talk about what you wanted to know.”

“Hmm … sounds kind of fancy. Maybe I should change?” she said as she dropped back down into the desk chair and typed a quick update and goodbye to her husband at the other end of the online conversation.

“How would you ever pick an outfit?” Don shot back with a smile, nodding his head towards the shopping bags he had just teased her about. “But I suppose you could start with what is in that one.”

Andee looked away from the computer screen to see which one Don was talking about, only to see him pointing to the lingerie package. She looked at him with a slight smile. For a few silent moments they held each other’s eyes.

“How do you know there’s even anything really interesting in that bag,” she said with a flirtatious and biting tone. “They sell more than just the sexy stuff, you know.”

For a moment, she thought she had Don off his game. She knew where conversations like this usually went – having had many with her male co-workers back at home.

Don sat quietly, almost poker faced, then said, “I’m willing to take that chance.” He reached over from his seat on the chair, grabbed the handle of the Victoria’s Secret bag and then held it aloft with two fingers. It was like he was inviting her to challenge his ‘dare’ … something he either saw in Andee or had already figured it out about her personality.

“I’m shocked at your suggestion. What would your wife think?” Andee shot back with a healthy dose of pretend surprise, practically sauntering over to where he was sitting.

“I would just tell her it was research for whatever item I brought home in a similar bag for her.”

Andee snapped the bag from Don’s hands, and then leaned in so they were almost nose to nose. “Well, research is what we are all about.”

She grabbed a few of the other parcels and strutted off to the bathroom to get changed. Smirking at the feigned disappointment in the “where are you going?” coming from behind her.

She quickly slipped out of the clothes she was wearing and routed through the packages she had dumped onto the bathroom counter. She pulled out everything from Victoria’s Secrets and plotted how she would make this work. What Don didn’t know, even in his jest, was that she had purchased some very – seductive – lingerie that wasn’t exactly meant for a night out with anyone but her husband. Even then it was more in line with being on the floor longer than on her body.

She gently removed the tags from the very lacy bra and panties first. After she slipped them on, she adjusted the matching garterbelt and wrapped it around her waist before removing the sheer black stockings she bought to finish the look. She took a quick look in the full-length mirror, giving a little twist and turn to check that everything was sitting just right. Her hard work and sweaty hours in the gym back at home was paying off.

The lingerie really didn’t do much other than offer a visual indulgence for anyone looking. The bra was so sheer that her nipples could be clearly seen. The tiny wisp of pubic hair above her pussy wasn’t hidden any better.

Next up was the dress. Andee wasn’t sure exactly what she was going to do here, as once again, her shopping had not been for work-appropriate clothing; least of all going out in public with someone she had only met a few hours earlier. “What the hell,” she thought to herself as she held up a wispy red number. It was clingy enough to show off her curves … and probably a bit more given what she had on underneath.

“Ready,” she stated in a loud voice, checking her hair in the mirror one last time and stepping into the black pumps she had brought along.

“Wow!” Don said as she emerged from the bathroom. Andee smiled as the expression on his face was the only compliment she was really looking for. “You look … wow … uh, not what I was expecting … I mean it’s really good … gorgeous.”

“Thank you,” she smiled touching his elbow as she passed by him the way to get her purse. She could sense his eyes checking her out from behind. It made her feel even better about asking him out for dinner, knowing she would have his undivided attention; even if for some rather dubious reasons.

Throughout the meal they chatted about all the business things she was hoping, mixed in with some personal stuff. Every now and then, she would catch Don’s eyes wandering over her body. She was excited at another reinforcement that she still had the ability to attract another man’s attention. It was something she and her husband often talked about in this sexual adventure Andee was pursuing.

It didn’t hurt that the wine was making her feel a lot more at ease, and added its own hint of spice and innuendo to the conversation. By the end of desert, the business talk had all but disappeared as they each opened up a bit more about life away from work, relationships and past experiences. They took turns sharing some of the unusual moments from their business travels. It didn’t take Andee long to figure out that Don definitely was a bit of a player when he was away from home.

“So what does your wife think about you being away from home so much,” she asked, taking a sip from her wine glass.

“I think she is pretty much used to it now,” he replied. “I guess it doesn’t hurt that she’s banging her boss on a regular basis.”

Andee was shocked at the statement. “Oh my god! Really? How do you know?”

“Some things aren’t hard to figure out … especially when she forgets to hide the condom wrappers,” he said bluntly. “I don’t need condoms.”

Andee let the silence take over for just a moment, speechless at her companion’s personal revelation.

“Besides … I’m not really bothered by it. It gives me a bit of freedom of my own,” he continued. “Don’t get me wrong, it wasn’t all that easy to accept at first. But we still love each other. Sex is just sex, love is something … more. I guess some people just aren’t meant to live a life of monogamy.”

Andee listened and drank the rest of her wine as Don continued with his explanation of how his marriage worked. A lot of what he was saying wasn’t so different than what she was experiencing in her own relationship. Having married very young, she sometimes felt the pangs of having missed out on so much; a big reason for why she was now in the midst of a great personal journey of discovery – with her husband’s unwavering support.

“I think every married couple has their own quirks in their relationships,” she said. “The ideal of a white picket fence at the front of the house can often hide a very twisted reality behind the closed doors.”

Don chuckled. “That, my dear, is a very deep philosophy.”

As they walked back to their hotel, Andee slipped her arm through the crook of his elbow. They strolled almost aimlessly along, casually discussing the realities of commitment and its relationship to personal desires and growth.

In the elevator ride back up from the lobby, Don leaned in very close to her. Andee felt a wave of excitement flow through her at the sensation of his body pressing against her.

“That was one of the best nights I have had at one of these things in a very long time,” he said in a soft voice. “Thank you for listening.”

Andee turned her head to reply. Her face was just inches from his. She looked into his eyes and couldn’t really catch herself from saying, “It doesn’t have to be over just yet.”

In her mind she found herself cursing at what she had just said. She had promised herself that she wasn’t going to misbehave anymore on this trip, but found herself attracted to Don more and more as the evening went on.

She blinked herself back to reality and quickly added, “I mean, we could just continue our conversation …”

“That sounds good,” Don said as the elevator arrived at Andee’s floor. She slipped out ahead of him, giving him the opportunity to watch her walk from behind. He remained behind her as she slipped her card into the hotel door and pushed it open.

“Unfortunately, I only have a couple of ‘girly drinks’,” she said as she walked into the room.

“I’m OK,” Don replied without taking his eyes off her ass. “But you go ahead.”

Andee bent over and grabbed one her vodka coolers from the bar fridge. It wasn’t that she really needed any more to drink, but she felt comfortable with something in her hand to fidget with. As she reached for the bottle, the hem on the back of her dress rose up just enough for Don to catch a perfect glimpse of her stockings from behind. She turned and sat on the edge of the bed as Don sank into his spot in the chair from before.

“So …” she said, fixing the hem of her dress so that it sat just right on her thigh. “What kind of things would your wife be interested in … other than condoms … if I was to take you shopping tomorrow?”

Don laughed out loud. She lifted the bottle of her cooler to her lips, trying to put on a sexy look without being too obvious as she took a sip and waited for his answer.

“After trying hard not to get caught staring at your legs all night, I think I would enjoy getting her something exactly like what you are wearing under that incredible dress,” he replied.

Andee smiled as she uncrossed her legs and then crossed them very purposefully as Don’s eyes fixed on them.

“A leg man, eh?” she said, with a hint of her Canadian stereotype coming out. “You think I have nice legs?”

“Fucking amazing legs,” he sputtered, not tearing his eyes away. “And the rest is goddamn incredible too.”

“Thank you. I’ve been trying hard all night to catch you looking at them. I was beginning to wonder if I should take my purchase back to the store and complain.” Andee stretched one leg straight out, as if the give it an inspection, revealing more of the lace nylon around her thigh.

“Uh … no … no, your purchase is working fine perfectly,” he said, scanning the full length of her outstretched leg and up her body until his eyes met hers. “In fact, I’ve been trying hard to hide just how well it has been working, all night.”

Andee glanced down at her companion’s crotch. She could see he was visibly turned on.

She got up from her seat on the bed and walked over to Don. She placed a hand on his shoulder and leaned in close to his ear, knowing his eyes would be shooting a glance down the top of her dress.

“Keep that thought in mind for just a minute,” she whispered. “I have one little thing to take care of.”

Andee walked over to the desk where her laptop was sitting. She smiled at Don as she sat down in the chair and crossed her legs, letting the hem ride up to reveal the naked flesh of her thigh above the stockings. She figured since the ‘secret’ was already out, there wasn’t much point in trying to hide behind some false modesty.

“Hey baby,” a message popped up on screen as she logged in. “Been waiting for you to get here. How was dinner?”

“I have a friend here. Still enjoying the evening,” she typed in. “Sit back, be quiet and watch.”

Andee left her computer on and turned to face Don. She purposefully struck a pose on the chair with her legs spread just enough for him to be able to see a hint of the black panties between her thighs. Carefully waiting for him to be distracted, she gently nudged the laptop with her elbow so the webcam would see most of the room.

She stood up and walked back to where Don was sitting. His erection was even more pronounced after he got a clear look up her dress. Andee took his hand and pulled him up out of the chair. With her heels giving her a few inches of extra height, she was able to almost look him in the eye. She wrapped her hands around his neck and smiled.

“Since you seem to be such a leg man, maybe I could take you to get some stockings for your wife? That is if you think she would be into something like that,” she said in her best seductive voice. “But you’re going to need to include a few other pieces, you know.”

Andee let her hands drop from his shoulders. She stayed close to him and unbuckled the belt around her waist that was holding her dress together, unhooked the small snaps and let it fall open. Don took his hands from her hips and slid them inside her open dress, touching her bare flesh for the first time. Andee felt a sharp tingle shoot through her body as his hands gently traced around to the back of her pelvis, down the soft spot where her back curved in above her butt.

Andee placed her hands on Don’s shoulders, allowing him more freedom to explore the curves of her body with his hands. He pulled her in and held her gaze for a moment before bridging the last few inches between them. She parted her lips as his met hers, and closed her eyes as his tongue gently slid in to touch hers. The electricity in this first kiss hit Andee right between the legs. She could feel her pussy come alive as the passionate embrace continued.

Breaking the kiss for a moment, Andee pushed back from her friend and slipped off her dress slowly, letting it reveal her flesh and sexy lingerie inch by inch. Don watched intently, licking his lips like a kid waiting for an ice cream sundae.

Once she had removed it completely, she turned and walked over to her suitcase and laid it down. Mostly, this allowed Don the chance to watch her ass and get an even better look at her in the sexy underwear. Andee turned back to face her friend and struck a little ‘hand on the hip all business’ kind of pose.

“Your turn,” she said, waving a finger up and down at him. Don smiled and pulled off his shirt. He was rather built for a man his age, obviously cared a lot about his body. He kicked off his shoes, pulled down his pants and stepped out of them. Andee could see the outline of his hard cock under his boxer briefs.

“The rest,” she said, her eyes fixed directly on his crotch.

“Holy fucking moly!” she gasped as his large cock sprung forward as he slid off his underwear. “Your wife is one lucky woman.”

Don had a very large cock, definitely the largest Andee had seen in person. While a ruler had never been a major part of her sex life, she figured he was a good nine inches long and thick. As he stepped out of his underwear and stood at the side of the bed, his massive erection was pointing straight at her.

Andee walked back over to her now naked friend. She took his erection in one hand and stroked him a few times, admiring how hard and hot it was. She watched herself stroking him and his hands began to explore her body, first brushing over the thin material holding her breasts in place, then sliding one hand under the edge. Andee closed her eyes in delight as Don played with her nipple. His touch sent a sensual pulse straight to her pussy.

She looked back up just as he leaned in for a kiss. His tongue darted in and out of her mouth as they continued to torment each other. Andee could feel her pussy getting wetter; kissing was one of the most surefire ways to turn her on – and Don was very skilled at getting her turned on.

Andee released her fondling grip on his large member and pressed herself against him so that they were chest to chest, penis to vagina. She gently adjusted him so his cock would run against her as they carried on with their kiss. After a moment, she felt Don’s strong hands grab her from her sides and lift her up. She wrapped her legs around her waist to hold herself up off the floor. He maneuvered them to the bed and gently laid her on her back in the middle.

Don kneeled between her spread legs and reached his fingers under the edge of her panties, pulling them to the side. He wet pussy was completely exposed to him, and it was obvious she was turned on. He ran a finger up and down the edges of her swollen lips, massaging her moisture and delicately spreading her wider.

His touch was driving Andee crazy, especially because every now and then his massive dick would touch her thighs as Don stroked her pussy and kissed her thighs where her bare flesh met the lace top of her stockings. She wiggled her hips in anticipation of more; she was growing anxious to feel that hugeness inside her.

As she moaned her pleasure, she felt his long finger slip into her hot cunt. Although her time in Denver had left her feeling rather abused between the legs, Don’s skilled internal massage hit on all the right nerves. Andee was now in sexual euphoria once again. He slowly explored the smooth inner walls of her slippery hole, twisting his finger around so he could find the spot where all her nerves came together. Andee was throbbing with excitement as Don’s finger found the little hump inside … the elusive g-spot. As he rubbed it, her muscles clenched hard around his finger, then relaxed. Andee’s breathing was getting very heavy.

Finally, he slid his finger out from between her pussy lips, massaging her sensitive clit with his thumb as he did. Andee shivered at the feeling and then felt what she had been growing desperate for. Don inched up towards her and positioned the head of his cock at the wet opening to her cunt. At first, he just rubbed the head of it up and down her wet slit until it was glistening with her juices, then pushed forward and slowly worked himself into her. Andee gasped as he parted her pussy with the wide girth of his manhood and slipped it in about halfway.

“Oh my god,” Andee moaned as he inched his cock in deeper and deeper. “You feel so … fucking … huge.”

She arched her hips up off the bed to meet his downward thrust, forcing even more of him into her. Andee clutched at his shoulders and tossed her head back. “Oh fuck,” she groaned, squeezing her fingers into his skin.

Andee shuddered as Don reached his deepest. She could feel his balls against her ass as he gave one last push. She pulled her body tight against him and let out a deep moan again. She held herself there for a moment, as if she was trying to catch her breath.

Don lifted himself up on his arms and began to slowly pump in and out of her cunt, letting her wetness lubricate his cock thoroughly. As she settled into the rhythm of having him fuck her, Don began to pick up speed and became a bit more forceful as he drove her hard against the hotel mattress. Andee matched his motion, gasping and groaning with each thrust of his cock into her.

“Fuck you’re big … fuck you’re big,” she repeated between her grunts. She was being pummeled into the mattress as her new friend fucked her with a sexual fury she had not experienced in some time. Andee loved a really hard fucking every now and then, but with the girth and length of a man like Don, she was lost in the heat. Not even with her biggest dildo did it feel this good to have something buried in her pussy.

Then, with just as much tenderness as aggression, he slowed down his pace, allowing her cunt to feel every inch of his cock as he pulled almost all of the way out of her and then gyrated it back in. He had this hip action that would angle his cock to rub against her g-spot as he did. Andee was clutching at the mattress and had her legs tightly wrapped around Don’s waist as he expertly fucked her. As he slipped his cock all the way in, she would squeeze her cunt muscles, trying to hold him there as long as she could before he would slip back out inch by inch.

She was lost completely in the moment, arching her back and surrendering as much as she could to Don and his steel hard rod. She had been so masterfully fucked with such an impressive cock, and deep inside her mind she knew she would be totally spoiled for any fucking that came her way after this moment.

Andee could feel the odd burning building within her cunt as her mind gave way to the physical sensations. She was close to having an orgasm, which was odd for her. It had been many years since she had experienced a vaginal orgasm without a little extra help. But the monster cock assaulting her cunt with such expertise was drawing one from her. She grabbed at Don’s arms and arched her back as she began to cum.

“Oh god, oh … fuck … OH FUCK yeah, Don … I’m cumming, I’m cumming,” she moaned loudly through her gritted teeth.

Then, as her cunt began to go off, Andee yelped almost involuntarily as she came on Don’s rigid cock. She twitched and jerked with delight as he kept up the throttling of her pussy. The wave of ecstasy was incredible.

Andee was still panting when the second wave hit her. She tightened her legs around Don and held him deep within her as her cunt throbbed. Sweat was running off her forehead, off her chest as she slowly came down from her orgasm.

“Oh my god, that was fucking amazing. Do you know how long it’s been since I came like that,” she said in between deep breaths. “Oh my god …”

Don kissed her as she gradually settled down, slowly grinding his still hard cock in and out of her. Andee broke the kiss between them, looking at her friend from underneath.

“I want to watch you fuck me,” she said. “Do me from behind.”

Don pulled his cock from the hot wetness between her legs and twisted around so he was on his knees. Andee quickly got up on her hands and knees facing the large mirror hanging on the wall at the bottom of the bed. She reached back with one hand and grabbed his cock, then slipped it into her cunt again. Don placed his strong hands on her hips and drove his erection the full length into her. Andee moaned at the sensation of him going so deep into her. She loved getting it from behind for this very reason.

Andee looked up at his reflection in the mirror, watching his face as he slammed away at her. She casually turned her head to the side, just for a moment to flash a sexy smile of delight at the open laptop on the desk. She knew her husband was getting the most incredible sex show of his life.

She could feel Don’s cock swell as he pushed himself deep into her. She knew he was on his way to unloading a torrent of cum into her. Then with one last thrust from behind, she felt the hot flood of his cum pumping into her cunt. He grabbed her hips and pulled her ass hard against his crotch; his hard cock throbbed as he let go shot after shot.

He held her there for a moment, letting his cock slowly deflate inside her. Andee kept her ass up in the air, but dropped onto her elbows, reaching back with one hand to gently massage Don’s balls as the last of his cum dribbled into her. After a few minutes, Don pulled out from her cunt and collapsed onto the bed.

Andee flopped onto her back in the middle of the bed beside him. Don’s cum oozed from between her legs as she rolled onto her side and rested her head on his chest. She reached down and gently massaged his now soft cock.

After a few minutes of lying there together in silence, Don rolled over and off the edge of the bed, heading for the bathroom still without saying a word. As soon as he closed the door, Andee leapt up and slid into the desk chair, bringing up the messenger screen that had been minimized throughout the whole encounter.

“Get all that,” she quickly typed on her laptop. Don’s cum dripped onto the chair, as she anxiously waited for an answer.

“Every delightful moment,” the reply came back on screen. “Enjoy your shopping trip tomorrow.”

Andee smiled as she folded down the screen from her laptop just as Don emerged from the bathroom.

“Anytime you’re ready to go again …”