Kelli pulled her panties back up, hoping the gusset was absorbent enough to keep the cum seeping out of her pussy from forming a wet spot in her jeans until she could shower at the hotel. Jacob fucked her twice during the flight and was then busy landing the plane at an executive airport west of the city. Then they took a cab to a hotel a few blocks from the trade show they intended to visit.
She gasped when they entered their suite situated on one of the highest floors of the hotel with a breathtaking view. She rushed over to stand near the floor-to-ceiling windows taking in the sights. Jacob came up behind her, wrapping his arms around her to cup her tits in both hands. He nuzzled her neck and pinched her nipples through her shirt and bra as she squirmed and giggled.
“So how do like the room?” he asked, slipping one hand under her bra to fondle her erect right nipple directly.
“Room?” she gasped, reaching behind her back to squeeze his stiffening cock through his trousers, “This place is larger than most apartments my friends live in back home.”
After a moment, they ripped at each others clothes to stand naked in front of the windows. Jacob kissed her deeply as he fingered her pussy then turned her around to face the windows. He pushed her until her tits were crushed against the glass as he slid his hard cock into her, humping her wildly before shooting even more cum into her puffy sticky cunt.
Kelli was cumming herself before he finished. Being fucked in that position for all the world to see was one of her deepest fantasies…one Jacob somehow figured out without her ever mentioning it to him.
After taking a quick shower, Jacob and Kelli walked over to the trade show site to look for her former boss. They found him manning a display very similar to the one from the previous year along with a lithe redhead Kelli immediately recognized as Stephanie, a girl who was a year behind her in school and deemed by everyone Kelli knew as by far the sluttiest girl there. Eric, her old friend and former boss, greeted them warmly, giving both Kelli and Jacob tight hugs.
“I know who she is,” Kelli responded while smiling wanly when Eric went to introduce her, “we were in school together but different years.”
Stephanie could barely conceal her smirk when weakly shaking Kelli’s hand. Her entire attitude changed when Eric introduced Jacob, smiling brightly and visibly throwing out her considerable chest. They chatted for a few minutes before Jacob invited them to dinner and excused himself and Kelli to get some shopping done before then.
“You seemed a little chilly towards Stephanie,” Jacob said to Kelli as they walked toward a well known department store to shop for some clothes.
“As I recall, she was the college slut for all three years we were there together,” Kelli told him as they worked their way to the high end dress area, “if someone had a cock or pussy, mouth or asshole, she would happily suck and fuck them, boys and girls, single, couples, groups and even a couple teachers and parents if the rumors were true.”
“Gee, sounds like our kind of girl,” Jacob chuckled, ducking to the side to avoid the punch Kelli aimed at his shoulder.
“I’m not concerned about us and if you want to, feel free to fuck her silly,” Kelli replied, holding up a slinky dress in both hands, “but Eric is almost old enough to be her grandfather and has a really wonderful wife and kids. I wouldn’t put it past Steph to fuck him blind, take as much as she can from him and leaving him a wrecked shell.”
“Well, he is a grown man,” Jacob responded, handing her a strapless red dress that didn’t look like it had enough fabric to cover both her tits and pussy at the same time.
‘Yeah he is and, undoubtedly like most other men like you, let’s his little head do all the thinking when it comes to a pretty girl very willing to drop to her knees or spread her legs for him.”
With that Kelli took the red dress and three others into the changing room while Jacob made himself comfortable on a chair outside. They continued chatting through the closed half door as she stripped down to her panties and put on the red dress first.
As Kelli suspected, when she pulled it up far enough to cover her nipples, the very bottom of her panties peeked out under the hem. To make matters worse, the dress was so tight even the small bikini lines were clearly visible, meaning it was a dress designed to be worn without panties. She stepped out of the dressing room to twirl around once in front of Jacob.
“Oh I like that one,” he chuckled as she glared at him, “seems like the perfect dress for a nudist.”
“Hardly,” Kelli huffed, turning back to the changing room, “it’s one thing being naked at home or the resort and entirely a different matter to have my tits and ass and pussy hanging out of a dress in a restaurant or club here.”
Over the next half hour or so, she tried on different outfits. For some, the color just wasn’t right and others didn’t flatter her body suggestively the way she wanted. Basically she wanted a fairly slutty look without one tit popping out…at least not accidentally.
A sales woman brought additional dresses in a variety of colors. Finally Kelli seemed satisfied with a dark purple backless one that ended just inches below the curve of her ass. It too was so tight it didn’t allow for panties and that actually was just fine with Kelli. She had every intention of removing the inner lining around the built in bra too so her nipples poked out proudly.
Kelli and Jacob had barely ordered their first drink when Stephanie and Eric entered the restaurant, looking around for them. Jacob rose to greet them while Kelli stayed seated, wanting to appraise the other girl critically as they approached.
One thing was immediately evident. Stephanie clung to Eric tightly, her arm locked in his and her body pressed against his side. Kelli’s only remaining question was how long she had been fucking her old friend and boss.
Stephanie wore an outfit nearly as slutty as Kelli’s, a tight black dress that emphasized and complimented her pale skin and auburn hair. Her grapefruit sized tits swayed gently with every step, the sides clearly visible in the deep open cleavage of the dress. The lack of lines also told Kelli the girl wasn’t wearing a bra or panties either. The way she slid into her seat very deliberately gave Jacob a quick glimpse of her upper thigh and most likely her bare pussy.
As the conversation went on over dinner, Kelli’s first thoughts about the young woman proved accurate. Eric hired Stephanie right after she graduated. Two months later, he moved out of his house and into an apartment with her, filing for divorce from his wife of over thirty five years.
Throughout the dinner, Stephanie kept pressing against Eric with her hand under the table, clearly fondling his dick through his trousers. Kelli made some pointed comments about Eric’s wife and kids whom she knew since she was a little girl herself but they didn’t seem to affect Stephanie at all.
When Kelli placed her own hand in Jacob’s lap as they waited for dessert, she could feel his stiff cock pulsing against her palm. His eyes were locked on the girl’s open cleavage and the rock hard nipples poking through the silky fabric.
“She does have nice tits don’t you think?” Kelli whispered in Jacob’s ear as they both watch Stephanie nuzzle so close to Eric her right tit almost slipped out of her dress. “Want to bet if her nipples are pink or brown or if she shaves her pussy or not?”
Jacob turned his head sharply to look at Kelli, an impish grin on his face as he placed his hand on her thigh and dragged it up until he contacted her bare damp pussy slit.
“Are you suggesting we take them back to our suite?” he murmured softly in her ear before licking the lobe with the tip of his tongue.
“Sure, why not?’ Kelli responded, pushing her hips forward slightly so his fingertip found her warm pussy slit. “You want to fuck her and I’m dying to see what Eric says and does when you do.”
“Shaved and pink,” Jacob said lowly, pulling her close for a kiss.
With that, Kelli got to her feet and excused herself to go to the restroom. Stephanie, of course, instantly joined her. After listening to each other pee, they were fixing their makeup in the mirror when Stephanie stopped talking and turned to Kelli with a serious look on her face.
“Jacob is really quite the guy…you are very lucky,” Stephanie told her as she brushed her hands over her own tits to smooth the dress. “I wouldn’t mind at all having a chance to get him in the sack with me…if you were alright with that, of course.”
“What about Eric…wouldn’t he mind you sucking and fucking another guy, especially one young enough to be his son?” Kelli replied, turning to look Stephanie directly in the eye.
“He hasn’t so far,” Stephanie grinned devilishly, taking Kelli by surprise with that answer. “He kind of gets off watching me get fucked and sucking cock. He even likes licking another guy’s cum out of my pussy…and ass.”
“Then I guess you should ask Jacob directly,” Kelli responded coolly after a moment’s hesitation to absorb the new information. “I certainly don’t object if he doesn’t.”
Stephanie grinned at Kelli then walked out of the restroom, her hips swaying suggestively. When they got back to the table, Eric announced he and Jacob were taking them to a nearby club to dance and get another drink.
“So did you say something to Eric when you had the chance?” Kelli asked Jacob as they walked a few steps ahead of Eric and Stephanie.
“He said he was all for a nightcap in our suite after he had a few more drinks,” Jacob smiled sweetly, squeezing her ass cheek with the hand wrapped around her waist, “and if I could give him a few minutes notice when we were going there so he could down some blue pills.”
Kelli felt a twinge deep in her cunt, realizing for the first time that Stephanie might not have been the only one looking for new sexual adventures. Her nipples stiffened thinking she might actually do more than watch when they reached the suite.
On the elevator ride to their floor, Jacob reached over and fondled Stephanie’s ass. She turned and smiled at him while pulling Eric closer to her. Jacob grinned back and moved his hand to her inner thigh just below the hem of her dress.
Stephanie didn’t even turn to look back again. She wiggled her hips slightly and pulled the dress up around her waist until Kelli and Jacob could both see the lips of her pussy dangling slightly between her thighs. Then she spread her feet and bent forward enough to give them a good look at her gaping moist pussy slit and tight asshole. Jacob simply brought his hand up to her slit, splitting the damp lips with a fingertip.
“I told you she wouldn’t wait to get to the room,” Eric grinned cheerfully, turning toward Jacob and Kelli so she could see the bulge in his trousers.
With that, Eric reached over and pulled the top of the teenager’s dress down to join the bottom half around her waist, leaving her firm plump tits bouncing back and forth as she pushed against Jacob’s hand. Kelli smiled brightly and turned around, inviting Eric without words to unzip the back of her dress as Stephanie moaned with Jacob pumping his fingers into her pussy.
The hallway was empty when they arrived at their floor. Stephanie simply followed Jacob to the door to the suite with the dress gathered around her waist. Kelli looked at Eric and stepped out of her dress and handed it to him as she followed the young woman and her husband down the hallway and into their suite, naked except for her heels.
Stephanie squealed in delight upon entering the room. She apparently had never been in such a lavish suite, so high up with floor-to-ceiling windows. She pushed her dress down over her hips, kicked off her heels and threw her arms around Jacob’s neck, kissing him passionately before she fumbled with his shirt and trousers.
Kelli turned and grinned at Eric before stepping closer and very slowly unbuttoned his shirt, unclasped his belt and unzipped his trousers. He threw the shirt to the side as she pulled his pants and boxers down in a single motion She dropped to her knees in front of him, taking his still stiffening six inch uncut cock in her hands. For a few seconds she just looked at his hardening dick then leaned forward to lick the first drop of his precum when it bubbled to the head.
She turned her head when she heard Stephanie let out a loud yelp. She was bent over at the windows with her hands on the glass and her tits bouncing around wildly as Jacob plowed his cock into her cunt repeatedly.
“Stephanie said you like to watch her,” Kelli murmured, getting to her feet and leading Eric to a nearby chair. “You can fuck me or not while Jacob fills her cunt, that’s up to you. We have known each other a long time and I will understand if your uncomfortable doing anything with me. Besides, this is the first time I knew you were not cut.”
Eric wrapped his arms around Kelli and cupped both of her tits, thumbing her erect nipples as his rigid cock pressed against her ass. Kelli squirmed and reached back to swirl the head of his cock in two fingers. In front of them, Stephanie was panting raggedly between shrieks as one orgasm after another rippled through her young body.
“I’ve wanted to be with you like this since you first sprouted tits,” Eric whispered in Kelli’s ear while moving one hand down to finger her dripping cunt, “so I hope I can both fuck you and fill your mouth before the night is done.”
With that, he bent her forward and guided his thick cock into her waiting pussy. Kelli fingered her own clit, sometimes brushing against his cock as he pumped in and out of her. She was close enough to an orgasm that she started to cum when she felt his warm sperm erupting deep in her cunt.
Kelli was surprised by the level of Eric’s adventurousness. He quite happily licked Jacob’s cum from Stephanie’s pussy and then his own from Kelli’s. He eagerly stroked Jacob’s dick while Jacob jerked his as they watched Stephanie and Kelli bring each other to multiple orgasms, Once his and Jacob’s cocks were hard again, he willingly fucked Kelli in the ass at her request but finished in Stephanie’s mouth at hers. He seemed to love licking and sucking Jacob’s cock with both Kelli and Stephanie.
Dawn was breaking when they were all so spent they could do no more. Stephanie managed to get her dress back on enough she could walk through the lobby and into a cab. Jacob and Kelli didn’t even bother getting dressed, kissing them both passionately at the door before crawling into their own bed.
“I guess the bet is a draw,” Kelli giggled into Jacob’s ear before drifting off to sleep, “she is shaved but her nipples are dark brown.”
They spent the next few days with Jacob taking Kelli to all of the usual tourist attractions in the city and a few off the beaten track spots he knew. They also did more shopping for sexier and ever more risque clothing for her to wear to dinner and the clubs at night.
One afternoon, they decided to visit an adult store to acquire some new items for their collection. They wandered around the shop for a few minutes, picking up various items as they went. Kelli could feel her panties getting damp imagining what they could do with all the new toys. Then she noticed a doorway covered with a black curtain inconspicuously located in a far corner. As she watched, a few men disappeared behind the curtain.
“What’s going on back there?” she asked Jacob as he intently examined a double strap-on.
“The viewing booths and arcade I would imagine,” he answered her without much enthusiasm or even looking up.
“What’s that?” Kelli continued as two more guys entered and another exited from behind the curtain.
“There are booths back there playing porn on small screens. Guys, mostly, put money in the viewers and jerk off watching. Others might join them or just stroke themselves watching others.”
Kelli just looked at him for a moment, not comprehending that sort of thing went on in basically a public place. After a moment, she grinned evilly, wrapped her arm in Jacob’s and walked toward the curtain.
“Let’s go see what’s going on back there.”
At first, she was blinded in the dimly lit hallway behind the curtain. After a few seconds, she could make out a few dark shapes of guys standing in the hallway, their flies open as they stroked their cocks. Jacob took her hand and led her down the hall, past a few open doors to empty booths. About half way down the hall, a door on the right was open and a guy was on his knees in the booth sucking another. Across the hall two guys faced each other, jerking themselves off until their cum shot on the other.
Kelli felt a few hands brush across her back as well as one on her ass and another on her right tit. She pulled closer to Jacob, not interested in the seedy guys stripping her with their eyes or feeling her up uninvited as they jerked off. Jacob leaned over and said something to one of the guys and thanked him upon getting a response.
“What was that about?” she asked him, nuzzling closer as a guy nearby cried out and shot his cum into the mouth of another.
“He told me where the glory hole is,” Jacob responded, taking her arm and leading her further down the hall.
“Glory hole…what the hell is a glory hole?” Kelli asked never having heard the term before.
“One or more of the booths will have a waist high hole cut in the wall to the next booth,” Jacob explained as he turned to the right at the end of the hall and opened the second door on the right. “If someone wants to suck a cock, they put a finger on the bottom of the hole and the guy in the next booth sticks his cock through.”
“Just like that?” Kelli asked as they stepped into a small booth not much bigger than a broom closet.
“Yep, easy as that…no muss…no fuss,” Jacob replied, closing the door behind them and taking off his shirt, “well quite often a muss…but no fuss.”
Kelli stared at him for a few seconds then looked around the booth. There was a single plastic chair in one corner and a small video screen previewing different types of porn. She almost gagged at the smell of stale piss and cum and industrial strength cleaner, as well as the way the bottom of her sneakers stuck to the filthy floor. Jacob finished stripping naked but kept his shoes on.
“So where are the glory holes?” Kelli murmured, hearing someone moving around in the rooms on both sides of theirs.
“There and…there,” Jacob answered, pointing to waist high round holes about the size of a volley ball on each side wall.
As he explained that to her, two fingers appeared through the hole next to him and curled around the bottom. Jacob grinned at Kelli and stepped that way.
“Our first request,” he chuckled and slid his half hard cock through the hole to immediately be taken into the mouth of a guy with salt and pepper stubble on his chin.
Kelli looked on in awe, her own arousal growing. She loved seeing guys suck each others cocks and the situation was so perverse she couldn’t believe they were there. Jacob glanced back at her over his shoulder as he pumped his dick through the hole into the stranger’s mouth.
“Get naked and see if someone needs some relief at the other hole,” he told her before returning all his attention to his own blow job.
She pulled off her t-shirt and dropped her jeans, keeping her shoes on too. After placing them on top of Jacob’s clothes on the only chair, she stepped to the hole. She could see a shadow moving around in the next room but not much else. She took a deep breath and pushed two fingers through the hole.
Seconds later the biggest thickest black cock she ever saw even in a porn video punched through right into her hand. It took both her hands to completely wrap her fingers around the head of the monster. A droplet of precum dripped from the tip of that shaft and stretched to the sticky floor after just two slow strokes.