Two for One Drink SpecialbyCharlieGG©
Jennifer squeezed her boyfriend Greg's hand as the elevator opened on the 6th floor. They took a step into the hallway and then she turned and looked him in the eyes.
"Are you sure, Greg? I mean, really sure?" she asked.
Greg smiled and looked down the hall nervously.
"I think so. I mean, yes, yes. We can do this. I WANT to do this for you."
His response didn't totally put her at ease but it emboldened her to nod and turn to walk toward the stranger's room, her fingers still entwined in Greg's. She could feel herself breathing heavier than normal, her chest heaving a bit which caused her to look down and see her white barmaids blouse unbuttoned further than normal. She smiled at her earlier flirtation and marveled at where it had taken her now.
When they got to the room, she knocked on the door. The out-of-town businessman answered it, still in his dress shirt, although the tie was nowhere to be found.
"Hi," Jennifer said, in a meek tone that suggested teenage school girl. "Um, Greg, this is Alex. Alex, this is Greg..."
Alex shook Greg's hand and then looked back to Jennifer. "Well I'll be damned..."
= = = = =
ONE HOUR EARLIER
Jennifer glanced at her watch as she approached the bar. The time she saw on it was consistent with what her legs were telling her. She'd been on her feet slinging drinks and appetizers in the hotel bar for almost eight hours and now those feet were screaming at her.
"Almost there," winked Alexa from behind the bar, shoving a gin and tonic at her for her one last active customer of the evening, along with a shot glass full of golden liquid.
It was a weekday night, Wednesday to be exact, so the crowd had thinned considerably and most of the remaining barflies were sitting at the bar, watching the late innings of the Yankees game on TV. Well, that and Alexa's tits straining against her tight white top. Alexa made a lot in tips.
"Indeed," Jennifer smiled, and knocked back the tequila shot the bartender had offered, before grabbing the gin and tonic and spinning on her heels.
Normally Jennifer would have been perturbed with a lone straggler at the tables. Once he cleared out Alexa would certainly let her go and just handle things on her own at the bar for the final hour or so. But Jennifer's boyfriend, Greg, wouldn't be there to pick her up for another half-hour or so anyway so she was in no rush. That and the man in the shirt-and-tie drinking gin and tonics wasn't to bad to look at.
"Thanks Jen," the man smiled as she placed the drink in front of him. Jen bent at the waist to put the drink on the table, offering the patron a quick glimpse of her cleavage as she did. Alexa had nothing on Jennifer.
"Hey, am I keeping you here?" the man asked as Jen was about to turn away.
"Oh, ha, kind of but not really," Jen replied. "You're my last customer but I'll probably hang out and have a drink anyway so..."
"Well, then, why don't you have it with me," he smiled again.
Jennifer was more than used to being hit on at the bar, especially late when the night was coming to a close. It always presented a bit of dilemma as Jen had to let them down easily while also keeping her tip as high as possible. Like most waitresses, she kept her boyfriend a secret to customers, a single girl is more likely to get flirted with and get tipped better, but at the end of the night the boyfriend was also the easiest way to accomplish her goal.
"Hmm, I don't know," Jen said, considering the offer. "I'm not sure my boyfriend would love that and he's coming soon to pick me up, ya know?"
"Then I'll buy him a drink as well," the man said, non-plussed, kicking out a chair. "Come on, you're going to have one anyway, right?"
Jen paused. This was usually the time when she gave a big flirty smile and said "Oh not tonight, thanks though..." but the idea of getting off her feet was virtually irresistible.
"Okay, one drink it is," she acquiesced. "I'll even get it myself..."
A few minutes later, Jen had lost her apron and notepad and was sitting across from the handsome stranger sipping a dirty martini.
"I'm Alex, by the way," he said.
"It's nice to meet you Alex," Jennifer beamed, taking another sip.
"So does your boyfriend always pick you up after work? Save you from terrible letches like me?" Alex asked, smiling.
"Ha, not always, but usually, yes," Jennifer laughed. "But I don't need saving, I can take care of myself."
"I'm sure that's true," Alex said suggestively.
Again, Jennifer usually would have gagged at the sleazy come on but Alex was more than a little attractive. In fact, the more Jennifer looked at him (and the more the martini went down) the more she liked sitting there.
"So what's the plan tonight for you," Jennifer leaned forward, placing her elbows on the table and once again pushing her tight-fitting white top with the buttons forward.
"You're looking at it," he said, raising his glass. "Flew in town today for a conference, starts tomorrow morning."
"Well I'm flattered you're spending your first night in town with little ol' me," Jennifer giggled, warming to the flirting game with the good-looking out-of-towner.
"So let me ask you..." she continued. "Why buy me the drink, even though you know my boyfriend is on the way?"
He smiled and leaned back in his chair.
"Why not? You're good company, nice to look at," he made a point of looking her up and down. "Let me turn the tables, why did you say yes if the boyfriend's on the way?"
She mimicked him, leaning back against the soft backing of the chair.
"Why not? You're good company and certainly nice to look at!"
They both laughed.
"Well here's to good-looking people drinking together," Alex held up his glass and clinked it against Jennifer's when she did the same.
"I'm glad I measure up," Jen beamed.
"Oh please, you're well aware that you do," Alex chided her playfully, his gaze sliding from her eyes down to her chest. "The outfit certainly helps the cause. I'd imagine you and the bartender get your fair share of leering eyes."
"Oh, occasionally," Jen smiled and ran her fingers over the buttons of her shirt. "See the problem is these damn buttons never stay fastened..."
And with a flick of her fingers she let another button on her shirt go, exposing more cleavage.
"Now you're just being mean..." Alex shook his head. Jennifer laughed again.
"Oops! Did I do that?"
Alex continued shaking his head.
"Mean, I say."
"Well now I feel bad for teasing you like that," Jennifer gave him a wide-eyed look, going for innocent.
"I'm quite sure," Alex laughed. "Okay, seeing as you seem more than comfortable around strange men, let me ask you a question..."
Jennifer reached up and pulled the hair band from her head, shaking out her long brunette locks, letting them fall over her shoulders.
Alex stared at her for a couple of seconds, as if sizing up how far he could go. He went pretty far.
"Tell me your favorite unfulfilled sexual fantasy."
Jen stared back. "What?"
"You know, what would you like to do sexually that you and the boyfriend haven't done..."
"Wow, no small talk here, huh?"
Alex laughed and leaned back in his chair.
"Okay," Jennifer said, steeling herself. "I guess I'd like to have a threesome with two guys."
"Ah yes," Alex nodded. "A very popular choice I'm sure."
Alex paused, looking at Jennifer for a couple of seconds before adding, "Well, let's see what your boyfriend thinks when he gets here!"
Jennifer almost choked on her martini.
"Oh God, don't tell him I told you that, he'd probably bug out!"
"Well how are we going to know if he's willing to do it tonight then?"
Now it was Jennifer's turn to stare for a few seconds.
"Wait. Are you... are you saying you'd be willing to do that?" Jennifer's felt a lump in her throat as the thought of Alex joining her and Greg filled her mind.
"Well, sure, what else do I have to do?" Alex laughed.
Jennifer still wasn't sure if he was being serious or just messing her.
"Listen, buddy, don't go getting a girl's hopes up like this!" She joined his laughter.
Alex shook his glass, rattling around the ice cubes and looking at Jennifer.
"Looks like I'm done here," he stood up. "So here's the deal. I'm in room 607. If your boyfriend decides he's up for it, come find me..."
Alex winked, threw a handful of bills on the table, grabbed the suit coat from his chair and headed toward the lobby.
"It's not going to happen!" Jennifer called after him.
"Then it'll be my loss!" Alex called over his shoulder with a smile, not breaking stride.
"Well I'll be damned..."
Alex stood at the door looking out at Jennifer and Greg.
Greg was not what he had expected. He was good looking enough, and seemed athletic standing in his athletic shorts and a hooded sweatshirt, but he wasn't the stud he expected Jennifer to fall for.
For Jennifer's part, she had actually unbuttoned another button on her blouse and Alex could see her peach-colored bra peeking out.
"So..." Jennifer said, trying to sound a little more in control than she felt. "We're, well, we're here! Can we come in?"
"Of course," Alex stepped to the side and let them enter the room.
"So here's the deal," Jennifer started in before she had even cleared the doorway. "Greg and I have talked about this a bit downstairs, we have some pretty simple rules..."
"Of course," Alex said. He smiled but Jennifer could see he was still processing their appearance. His manner didn't quite have the same devil-may-care feel it did earlier in the bar. She realized he was nervous too.
"If either of us, well, I mean, if ANY of us get uncomfortable and they want to stop, we stop, everything," Greg chimed in. Now that he was in the room he was having second thoughts himself and was thankful that Jennifer had insisted on a couple of shots at the bar before they went up. The buzz was hitting him just now.
"Agreed," Alex nodded.
"And..." Jennifer continued, looking from Alex to Greg and then back to Alex again. "We've never done this before, I mean, you know that and... well, we also decided downstairs that you and I..." she motioned to Alex, "shouldn't have sex. I mean, you know, no actual intercourse between you and me."
Alex nodded slowly but didn't respond at first.
"Okay, yes," he finally agreed. "That makes sense..."
Jennifer took a deep breath. That was it. That was really all they had come up with. The right for anyone to stop it at anytime... and no sex. She and Greg had agreed that they simply didn't know how they would react to this experience. Softening the impact seemed to be the right way to go.
Jennifer turned her head to Greg and looked into his eyes.
"I love you sweetie," she said and wrapped her arms around his neck. Greg leaned in and kissed her softly on the lips... and then a bit more hungrily, his tongue pushing into her mouth. She returned his kiss and then felt her hair sweep to one side and another mouth begin to rain kisses down on the back of her neck. She moaned into Greg's mouth as Alex's hands moved around to her front, pressing between their chests, and began to unbutton the rest of her blouse. Jennifer continued to kiss her boyfriend, her tongue pressing against his as Alex pulled her blouse off her shoulders. A couple of seconds later she felt the clasp of her bra release and it fell to the ground, letting her 36Ds fall free.
Greg pulled free from her mouth and kissed down her neck to her breasts. As Alex held her tits up to Greg's mouth, Greg flicked her nipples with his tongue, hardening them. Jennifer leaned her head back and found Alex's mouth behind her, their lips meeting to make out as her boyfriend licked and suckled her nipples.
Greg's hands moved down to her skirt and tugged it down to the floor, leaving her in nothing but her peach panties and heels. She felt Alex move away from her and then he pulled her down on the couch, with him seated behind her. He continued to kiss and nuzzle her neck as his hands reached around and played with her breasts.
For his part, Greg knelt between her legs and kissed his way up her legs... starting with her calves and then the inside of her thighs... before finding his way between her legs. He pulled aside her panties and his tongue found her wetness, sending a shiver up her spine and she let out a loud groan.
"Oh my Goddddddddd...." She breathed, spreading her legs to give Greg access to her now dripping pussy.
Greg's tongue began lapping hungrily at her while Alex whispered in her ear "My God, you're beautiful..." while he kneaded her globes with his fingers.
The reminder that there was another man with her and Greg turned her on and Jennifer began to writhe against Greg's tongue. She felt her cheeks and chest blush as the shivers down her spine intensified and soon she was letting out a guttural groan as she reached orgasm faster than she ever had.
"Fuck, I want to see you guys..." she whispered, pushing Greg away.
She rolled to her right and pushed Alex to his feet.
"No fair, I'm the only one naked!" She giggled, standing up between them. "Let's get some of these clothes off..."
She turned to Greg and lifted his sweatshirt up and over his head and then his t-shirt quickly followed, leaving him in just his shorts. She looked him in the eyes and took a deep breath. She turned to Alex and kissed him hard on the lips as she unbuttoned his shirt. She felt Greg's motion behind her as he moved and Jennifer slid her hand down to massage the bulge in Alex's groin, sliding her hand up and down slowly. Alex let out a moan as she found her target. At that moment, his shirt slid backwards off his shoulders and Jennifer, still kissing Alex, opened her eyes to see Greg behind Alex, pulling his shirt off.
Jennifer braced herself for Alex to buck at the realization that Greg was running his hands down his back, but instead Alex didn't flinch at all, putting his hands on Jennifer's panty-covered butt and continuing to kiss her.
She put her hands on Alex's bare chest and pushed him back a bit, releasing from their kiss. She took two steps back and sat on the couch, her fingers sliding down her body as she pushed her hand into her panties and began playing with herself slowly, never taking her eyes from Alex's.
"Remember the rules," she cooed softly. "If you want anything to stop, just say so..."
As she said that, Alex felt Greg's hands reach around him and undo the button on his dress pants. Greg's fingers then took hold of the zipper and slid it down slowly while Jennifer watched from the couch.
"Holy shit you guys are soooo hot," Jennifer breathed out, her fingers picking up the pace on her clit.
With one tug of his hands, Greg pulled Alex's pants and boxers to the floor, causing Alex's hard cock to spring forward.
"Mmmmmmmm," Jennifer licked her lips as she saw his length. "Fuck..."
She pushed herself off the couch and knelt between the two men. Her one hand clawed at Greg's boxers while the other encircled Alex's rock hard cock and guided it into her mouth.
"Oh yesssss..." Alex moaned, his head falling back when Jennifer wrapped her lips around his shaft and bobbed her head slowly. Greg gave an "mmmm" of his own as her fingers stroked up and down along his dick.
After 30 seconds of sucking and stroking, Jennifer turned her head and gave Greg his turn at her wet mouth, rubbing her saliva all along Alex's thickness.
"Your cocks are gorgeous guys," Jennifer giggled when she finally pulled off of Greg. "I can't decide, I want them both!"
She tugged playfully on each, bringing them closer and finally together so she could encircle both with her mouth. Bobbing her head downward, the two erect shafts stretched her mouth to the max as she attempted to take them in.
After a short attempt at the double blowjob, Jennifer was ready to change it up.
"I want Alex to eat my pussy," she looked up at Greg for approval.
"I wouldn't mind seeing that myself," Greg nodded, warming to the idea of his girlfriend's body on display.
Jennifer laid back on the couch and spread her legs. Alex didn't need an invitation, he spread her legs with his hands, pushing her knees back toward her chest and dove in with his lips and tongue.
"Oh fuck yessssss," Jennifer hissed, looking down at Alex. "Eat that fucking pussy..."
Greg stood watching, stroking himself, mesmerized by Jennifer's brazen display.
"Come over here and fuck my mouth!" Jennifer growled at him and he quickly obeyed, kneeling on the couch and thrusting his cock toward her face. "Mmmppph" she let out a grunt as he slammed his cock in and out of her mouth, the back of her head pushing against the couch.
For the second time that night, Jennifer came as a man lapped at her pussy with his tongue, this time so hard that she pushed Greg away, for fear of biting down on him. Instead she buried her mouth in the couch pillow, letting out a low scream.
"Okay," Alex said, coming up for air. "We need to switch here or I'm going to violate your second rule!" referring to their ban on Alex having sex with Jennifer.
"FUCK ME!" Jennifer practically yelled at Greg and shoved him off the couch.
"And you... " She looked at Alex with a wild-eyed look, "get over here..."
Alex sat next to her on the couch as Greg positioned himself between her legs. Alex ran his hand up her stomach to her breasts and tweaked her nipple as Greg slid his cock into Jennifer's waiting pussy.
"Oh yeah..." She smiled and then turned to kiss Alex.
As Greg began to slowly push in and out of her, Jennifer's tongue played softly with Alex's. Instead of the heated, hungry passion that had been the staple of the night so far, now Jennifer felt the need for a slow, sensuous stretch. She ran her hand over Alex's chest as he did the same to her and the two of them kissed passionately.
Greg watched, aroused and began to thrust a little faster, a little harder...
Jennifer reached down and took Alex's cock in her hand. Again, she began to stroke him, enjoying the feeling of his thick shaft in her hand as Greg fucked her long and hard.
"Oh GODDDDD this is AMAZING..." she let out, and turned to watch Greg plunge in and out of her. Alex laid back against the couch and watched as well, feeling the sensation of Jennifer's soft hand massaging his penis.
"I want you guys to cum all over me..." Jennifer said, looking each of them in the eyes as she said it. "Come on guys, cum on my fucking tits and stomach..."
She closed her eyes as another orgasm built inside her. Her body tightened and the familiar flush came across her chest as she tensed up and then released, letting out a long "ahhhhhhhhhhh."
Immediately following that, Greg pulled out at the same time Alex pushed himself up to kneel over her. She continued to stroke Alex as Greg squirted line after line of cum along her stomach.
"Yes, oh yes, hot and sticky..." Jennifer licked her lips and stroked Alex faster and faster. Seconds later, Alex reached his own orgasm and he sprayed all over her chest and stomach, mixing his own cum in with Greg's.
"mmmmm hmmmm hmmm..." Jennifer giggled, massaging her hands over her tits and stomach, rubbing the cum over her body. "Holy SHIT that was fantastic!"
She leaned forward and gave Greg, still on his knees, a huge kiss.
"That was amazing, thanks Alex," she giggled, her glistening breasts bouncing playfully.
"Anytime," Alex waved at them as he fell back on the couch and laughed.
"Hey, do you mind if we use your shower?" Greg asked. "I think we need to clean her off before we go..."
"Oh," Greg added. "and next time, I think I'd like to see Alex fuck you..."
Jennifer's mouth dropped open and she felt her pussy get wet again.
"It's definitely a date..." Alex smiled.