Four horny guys, on a weekend getaway at the Ritz-Carlton, take turns fucking all three holes of an attractive waitress.
Chapter 63:
TAKING TURNS WITH CARLA
63. In an Executive Suite at the Ritz-Carlton Atlanta, I enjoyed a mid-day tryst with a lovely flight attendant. She had told me that not only was she staying at the same hotel, but she was working the same flight I was on returning to Orlando. I showered, exploring the possibilities in my mind. Just imagining her enticing bits got me rock hard. The warm water cascading down on me washed away the results of my orgasm.
The others, Al, Jack, and Tommy weren't due to arrive until late afternoon. I decided to explore the amenities this 5 star hotel had to offer. My first stop was at the concierge desk in the lobby. I asked for the head concierge and was escorted into a private office off to one side.
A soft rap as he opened the door. "Excuse me, Mr. Condon. This is Mr. Sailor from the Executive Suite. He said he had spoken to you recently and wanted to finalize his business with you."
Mr. Condon rose and extended his hand as the other concierge slipped out, closing the door behind him.
"Ah, yes. Welcome, Mr. Sailor. I trust that your suite is up to your standards?"
"Yes, absolutely, Mr. Condon. You may recall that we spoke about the various escort services available. There will be four of us between two suites."
"Certainly, sir. I clearly recall." He went on to iterate the various options available and inquire about our preferences. He even went so far as to call up some of the agency’s websites on his computer, offering his insights and recommendations. "Once you've decided, simply phone me with your choices and schedule. I will personally make the necessary arrangements. And, as a full service establishment, we handle all the billing as well. Will there be anything further, Mr. Sailor?"
"Not at the moment. I'll be in contact later today. Thank you for your time."
With that in place, I wandered through the hotel amazed at the efforts taken to pamper the guests. Everything was first-class, designed to cater to the elite. It was a culture shock to me, a vagabond boater used to wearing nothing but my boxers and eating off paper plates. Eventually I returned to the suite, ordered some room service food, and relaxed.
I must have fallen asleep because the next thing I knew I was rudely awakened by a commotion at the door. It flew open and in walked Jack and Tommy, two of the Sorry Six. A great hubbub ensued as we greeted each other, hugs and back slaps included.
"You guys must be thirsty after your travels. Let me pour you a drink and we can flesh out our agenda. Al left word that his flight from St. Thomas had been delayed. Not sure when he'll arrive."
I poured drinks and we sat in the living room in animated conversation. I filled them in on my plans regarding escorts. Jack was ecstatic and rattled off his requirements: big butt, big tits, natural bush, Brazilian preferred (Jack hails from Brazil), Latina acceptable. Tommy sat quietly, a look of concern on his face. "OK! Got your number, Jack. How 'bout you Tommy? Short or tall, skinny or fat, blonde or brunette? What’ll it be?"
Tommy is a sweet soul, not a mean bone in his body. He's smart enough to have graduated with us from a prestigious private university and followed on with law school. But he doesn't come across as the sharpest pencil in the box. He's not a flamboyant courtroom litigator; his talents and intellect are better suited to backroom legal research, finding that obscure precedent that wins cases. He's very awkward socially. After an uncomfortable pause he murmured "Hate to spoil the party guys, but I'm gay now."
You could have heard a pin drop in the ensuing silence. Simultaneously, Jack and I stumbled over each other's words letting him off the hook, accepting him for who he is, and suggesting that we could arrange a male escort for him.
I stepped away into the bedroom to call Mr. Condon with this update. While I was on the phone there was more commotion with excited voices coming from the other room. I finished my call to discover that Al had arrived! Al and I were roommates for 3 years at college. It was great to see him again.
Now that we were all assembled, the drinks started flowing. We decided that since all the Sorry Six weren't here, we would carry on as the Fucked Up Four. I got Al's escort order, and we agreed to host them Saturday night. I disappeared to give Condon a call to finalize our 'order.'
We collectively agreed to visit the hotel restaurant for dinner. Once seated, a comely lass appeared to take our order. Al and Jack were all over her, flirting mercilessly and dropping not so subtle hints that her talents were being wasted and how much more she could make for "just a simple visit to our suite." She flirted right back at them showing interest in just how much she could make. When she served us our after dinner drinks, Jack peeled off five, hundred dollar bills, laying them on the table. "An equal amount when your visit's over."
Her eyes popped open, and she sucked in her breath. Regaining her composure she inquired "Now which suite was that again?"
Four boisterous men, half jacked on booze, created a commotion as we stumbled through the lobby to the elevator. We went to the other suite, Jack and Tommy's. To be honest, I couldn't see enough difference between our suites to warrant a $300 price difference. Until, that is, Jack opened a cabinet door by the kitchenette revealing a fully stocked liquor cabinet. No need to call for bottle service, no sir.
With fresh drinks in hand, we relaxed in the living room. We waxed nostalgic, reliving some of our college pranks, exploits and shenanigans. Uproarious laughter, some pantomimes of our dirty deeds and general hilarity ensued. Then came the knock at the door. Tommy answered it.
She had changed out of her waitress garb into a sleek, tight fitting dress. Some fresh makeup and high heels had turned her into the fantasy we all craved. Except Tommy, that is. Grasping the situation, Tommy ushered her into the room, adopting the role of her guardian. "Hi, guys! My name's Carla."
Jack spoke first. "I'm Jack. Why don't you step over here and let us get a gander at you, Carla." Jack slid the coffee table to the side and Carla sauntered into its place. She struck several poses for us, showing off her assets. She was a beauty, and we were oohing and aahhhing in unison. "Lovely." "Beautiful." "Smokin' hot." "Nice rack." "Look at that fine ass."
"How about a little drinky-poo, guys? Just something to take the edge off, you know?" Tommy scurried to the bar. We made her stand in front of us as she hurriedly finished her drink. Tommy got her another and we continued to examine her nicely shaped body. She relished the attention and kept twisting, turning, and bending to give us a tease of what to expect.
Taking the lead, Jack stood, grabbed Carla's arm, and pulled her toward the bedroom, leaving the door open. We could hear zippers, shoes dropping to the floor and female giggles.
I took the opportunity to console Tommy. "Look, Tommy. I know you're gay but think of it this way. Whether you're a top or a bottom, it doesn't matter. I'm sure that you've had your cock sucked and you've fucked an asshole or two. Just think of her as a guy with long hair and boobs. Or keep your eyes closed and you'll never know the difference. She'll suck you and you can fuck her ass. What's the difference whether it's a guy or a girl. I mean, a blowjob's a blowjob and an asshole's an asshole, right?"
Al picked up where I left off, trying to convince Tommy to "grin and bear it" while I disappeared into the bedroom. Jack was lying on his back, and Carla was riding him. I stripped down, stepping to the edge of the bed. Carla instantly reached out and started stroking my cock. I got them to shift position, sliding closer to the edge so that we could DP her.
I got my dick wet with spit and positioned it at her puckered ass. With Jack pumping her pussy from below, I entered her ass driving him in deep in three strokes. As we were rocking her with our thrusting, Al entered the room. The next thing I know is that he was nude, standing on the bed, fucking her mouth. Poor Tommy! He didn't know what carnal delights he was missing!
When we stopped to rearrange, I noticed that Tommy was now in the room, sitting in a chair in the corner watching us have our way with this slut. He had his pants down to his knees and was jacking off. Once Carla was disengaged from our three cocks, she moved over and kneeled between Tommy's legs, wresting his cock from him, sinking her mouth down on it. He didn't object but you could tell that he was uncomfortable. Carla sensed it, too. She returned to the bed, laying on her back with her equipment at the edge. "Okay guys. Time to line up and come pound my pussy one at a time."
Al went first. We watched as he stood there thrashing away at her cunt. Full strokes going faster and harder. Soon there was the unmistakable cum groan. His cock made a wet, popping noise as he withdrew it, leaving his dripping cum for the next guy. Jack went next folding her legs up and wide. He mounted her and immediately began a high RPM piston fuck. His dick was slamming fast, and she was making guttural sounds of enjoyment. His high-speed hip thrusts suddenly stopped, and he cried out "OH FUCK ... PUTA ... VAGABUNDA ... PROSTITUTA!" A few more jabs and he was complete.
Next it was my turn. I had her turn over into doggy position. Obviously, no lube or foreplay needed so I grabbed her hips and impaled her. My strokes were measured, deep and each stroke ended with a quick, hard jab. I pumped into her cum filled cunt, pulling her hips back to meet my thrusts. After I made my contribution to her cum bucket, I stepped back. "Your turn, Tommy. Come on, slugger. Come get some of this nice tight ass."
Tommy had been sitting in the chair gently stroking himself and watching us take turns with our play toy. He looked surprised when I called his name. "Your number's up, Tommy. Time to come fuck this asshole. It's paid for and it's your turn. Hurry on now or you'll lose your place in line." He slowly stood up, reluctant and unsure if he wanted to do this or not. He ambled over and stood behind Carla's protruding butt. He looked at me, then at each of the others. Each one of us smiled at him and made hand motions to go ahead, do it.
Carla sensed his reluctance, so she reached around, spreading her ass cheeks for him. "Come on Tommy. I've been waiting to feel your nice cock stuffed up my ass. Have at it now, enjoy an assfuck. This one's on me, darling."
Tommy took hold of his dick and positioned it against Carla's anus. There was plenty of cum juice covering her whole crotch, so no extra lube was needed. He rubbed it around some, then pushed it in slowly. Carla let out a sigh. "Oh, yeah ... that's it, Tommy ... that feels awesome, baby." Her encouragement spurred him on some. He pushed and pushed getting about half his rod past her sphincter. He gave it a lackluster try, reaming it in and out about a dozen times before he withdrew and sat back down.
Al immediately took his place and began fucking the hell out of her poop hole. Her body was lurching each time he slammed into her making it hard for her to take Jack's dick into her mouth. Jack had climbed up on the bed standing in front of her, desperately trying to get his cock into her mouth - now a moving target. I stood by Tommy, congratulating him on at least trying to fuck Carla. "See? It wasn't that bad now, was it?"
"I'll be honest, Sailor. The whole time, all I could think about was sucking you off or having you fuck my ass. It may be a surprise to you, but I've had those thoughts and fantasies about you ever since college. It's the God's honest truth."
Hearing that, I stepped in front of him and grabbed his head, forcing it down on my shaft. He took to it greedily, alternately fucking me with his mouth and letting me skullfuck him. His was a wet, sloppy affair with lots of slurping and drooling. Toward the end, I held his head still and pumped my load into his mouth. He swallowed, gasped a bit, then looked up at me. "Thank you, Sailor. Thank you. You don't know how much that means to me."