A Little R&R

It was my first time visiting Chicago. I had always had heard nice things about it, but had never been and didn't know anyone. Fresh off another failed relationship, I needed to go away somewhere different, somewhere I could forget about work and my ex, just let my hair down and have a little fun.

I have a rather high-profile job in Boston, a high-priced attorney for corporate bigwigs who can't get out of their own way or keep their pants on. So I can't exactly let loose around Boston unless I want to end up in the gossip columns and lose my job.

I considered a trip to an island, it would be nice to just relax on a beach, but then I'd be surrounded by couples, by honeymooners. And while I have my heart set on a couple, I have it set on meeting a couple of men. My last boyfriend wasn't very adventurous and wouldn't even consider a threeway with the third being another woman. I had never been with a woman, though I had had a couple of threeways with two men. But with the right man, I'd be happy to engage in sharing another woman's pussy. But right now, my heart and mind were focused on one pussy only -- mine. I needed some attention, and the thought of being with two men again had me so turned on that before I knew what I was doing, I had booked a flight and hotel, my panties moist at the thought of meeting two perfect strangers.

I arrived on a Friday afternoon, checked into my hotel and took a hot bath. My plan was to stop at a bar I noticed as the cab took me downtown to my hotel, it looked like it might be a good place for after-work cocktails. So after I stepped out of the bath and toweled off, I slipped into a black pencil skirt with a slit up the left thigh, black thigh highs and three inch heels. My cream silk blouse was cool and soft against my skin, and the idea of a man or two unbuttoning it was enough to make my nipples stand at attention. I smoothed out a wrinkle, dabbed on some lip gloss and headed to the bar.

I pulled up a seat toward the end of the bar, my erect nipples poking through my peek-a-boo bra, the silk blouse caressing them. I ordered a glass of pinot noir from the bartender whose eyes dropped to my breasts, slipped on my glasses and took a book out of my bag. Soon, the bar began filling with men in Armani suits, women in Prada.

I saw them right away, two handsosme men in their 30s, talking with a group of men and eying me devilishly. I gave them a coy smile, and averted my eyes, turning back to my book. As I looked up, reaching for my wine glass, I saw one of them put his hand on his friend's shoulder, whisper something while meeting my gaze, and then he headed toward me.

My wine glass was nearly empty, so he offered to buy me another. Accepting, I took off my glasses and he saw just how blue my eyes were, his eyes slowly traveled to my mouth, down my neck and to my cleavage, the silk blouse clinging to my hard nipples.

I turned toward him, rubbing my leg against his as I did, switching my legs to cross left over right, and he saw the slit of my skirt, rising up my thigh to expose the lacy top of my thigh highs.

"I'm Lacy," I said, extending my hand.

His eyes glanced down at the top of my thigh highs and he smiled as he looked up, meeting my gaze. "Yes you are," he joked. "I'm Tom."

I offered him a chair and we got another drink. The conversation was easy and flirtatious, but I couldn't help but notice that his friend kept looking over at us.

"I think someone wants to join us," I said, leaning in to Tom and pointing at his friend, smiling and giving him a little wave.

"Come on over," he called, waving his friend over to our corner of the bar. "Lacy, this is Dave. Dave, Lacy."

"Nice to meet you, Dave," I said, shaking his hand and looking him in the eye, my eyes momentarily fixed on his mouth.

Dave's broad shoulders lead to a slim waist, but the way his pants hung on him gave me the impression that he needed his pants tailored to have a little extra room in the crotch. A good sign, I thought.

"So what do you do, Lacy?" Dave asked.

"She's an attorney in Boston, just here for a few days," Tom jumped in.

"I needed to get out of town for a few days, just kind of let loose and relax, have some fun. So here I am, looking for someone to have fun with."

"Ah, some one to have fun with," Dave said, thinking he may have been out of the game before it started.

I put my hand on his arm reassuringly. "Well, sometwo and somethree aren't words," I teased. "I'm just looking to enjoy my few days off, that's all. I'm spending too much time either working or entertaining myself lately, so rather than be alone I'd prefer a group activity," I said, winking.

"Well then," Tom said, clearing his throat, "what did you have in mind? Anything in particular?"

"I prefer to be spontaneous, and to be surprised," I said, standing up and reaching into my purse.

"Room 442," I whispered to Tom and kissed his cheek. "The hotel next door."

I leaned up to kiss Dave on the cheek, my hand on his chest as I stood on my toes.

"I hope to see you soon," I said, looking directly into his eyes, biting my lower lip.

I gave them each a last sly smile, waved and walked away.

I head back to my hotel room, put on some music, and stepped into the shower. It was just a few minutes before I heard the door open, then close. Tom pulled back the shower curtain and stood before me naked, his hard body surprising me a bit. His hard cock tempting me a lot.

"Well hello again," he said, backing me against the wall of the shower.

He leaned in to kiss me, pulling my right leg up over his hip, pushing his hardness against me. He slid his hand down between my legs, between my lips and felt his way around inside me.

I reached over to turn off the water, Tom's fingers still inside me. He slid his fingers out and we got out of the shower. He lifted me up and carried me to the bed where I hoped Dave was waiting.

I was a little disappointed at the empty bed, but I knew that Tom was going to be a lot of fun, even if it was just the two of us. If worse came to worst, it was only Friday, and it was early evening. I had all weekend to fulfill my needs.

We lay on the bed, wet, entwined, kissing and he made his way down my body, burying his face between my legs. I closed my eyes, drinking in every moment, every motion, every lick and thrust of his tongue and fingers. His arms are wrapped around my thighs and he pushed down on my belly as he devoured my pussy.

I never heard the door open.

When I opened my eyes, Dave stood before me, shirtless and dropping his pants. As he let his boxers fall to the floor, his enormous erection told me I was right, definitely a little extra room needed in the crotch.

I stared as his enormous, bulging cock, and subconsciously opened my mouth in anticipation.

"Is that for me?" Dave asked. "Is that warm mouth for me?" He asked again, stroking his cock and crawling on the bed toward me.

He straddled my face, dropping his balls into my mouth first. I reached up and began stroking his shaft with one hand, kneading his balls with the other, stuffing them into my mouth and massaging his swollen balls with my tongue.

I pulled my mouth back and reached up with my tongue, pulling his cock down toward my mouth to lick him. His pre-cum glistening on his head, I gently licked it off, and making eye contact.

"God I can't wait to feel my cock in your throat," he said to me, keeping his eyes locked with mine.

I licked his shaft, swirled my tongue around his head and sunk his cock into my mouth. I tilted my head back to open my throat and he leaned in.

"Oh shit, that's it honey, open that mouth, open that throat," he said lustfully. "That's right baby, slide it down, that's right ..."

Tom was so turned on by hearing his friend's words that his own hard on began to ache. His tongue and fingers sharing my dripping pussy, he drove his tongue deep inside, and pushed four fingers into me. He pulled his fingers out, grabbed my hips and pulled my hips tightly around his face, fucking my pussy with his whole face, begging me to ride his mouth.

With one hand on Dave's ass, pushing his cock deeper into my mouth, and one hand on Tom's head, pushing him deeper into my cunt, I could feel myself nearing an explosion.

"Turn me over," I beged, pulling my mouth off of Dave for a moment. "Turn me over, I need to get fucked ... now, please!" I begged.

I turned over onto my knees and looked back at Tom. Dave smiled at me as I slid my mouth back down on his cock and Tom knelt behind me fingering my dripping pussy, then slid his cock against my lips, not yet going inside me, teasing me. I backed my ass up, trying to get him inside, reaching between my legs to stroke his balls.

Dave could see my face, see my eyes ... he saw the lust and knew how badly I wanted Tom's cock inside of me.

"Fuck her," he told Tom. Tom slowly pushed his cock into my pussy and I gasped, my mouth full of Dave's cock. Tom began to rhythmically move inside me, pumping slowly, then faster ... I kept time with him. Tom forces his cock in my pussy, I force Dave's cock in my mouth.

Dave saw in my face as I looked up at him, sucking him faster, how much I need this, how much I'm enjoying having both of them.

I'm dying to straddle Dave, but I've never done DP before and I'm a little nervous -- at the thought of either, up my ass or both in my pussy. But I'm so turned on that the idea of two cocks in my pussy is magic.

Just then, Tom cums, he pumps me a couple of last times ... but I'm not done yet. I quickly straddle Dave, his thick cock nearly ready to explode from all the attention my mouth has been giving him. I slide down his cock, and grind into him, hard and fast, my breasts bouncing, my hair in my face. Grinding my pussy into him harder and harder, feeling him against me and in me.

They have never seen a woman fuck quite like this. They have never seen such lust in a woman's eyes. I grind, I fuck, and I ride him until I can't breathe ... and he turns me over, to fuck me from behind at the edge of the bed. He stands behind me, grasping the inside of my thighs to lift my ass up to meet him.

Tom goes around to the other side of the bed just to watch my face as Dave fills me up.

Finally, all three of us collapse on the bed. Tom strokes my belly, while Dave lies across the bed, stroking my leg as we regroup. We are wiped out, and all smiles. Blown away by what we just shared together.

My breathing is normal again ... I look toward the window and see a man standing in the window of the building across the street and I swear he's looking right at us.

Suddenly, I feel a twinge down below and feel the need to slowly spread my legs ... after all, Dave hasn't tasted me yet.

Dave smiles as I spread my legs for him, grinning mischievously.

"I think we have company," I said, looking toward the window. Dave and Tom smile at each other knowingly, Dave picks me up from the bed, kissing me as he carries me toward the balcony.

Tom moves the couch, positioning it in front of the sliding glass door, and fully draws back the curtains. Dave puts me down, and lays on the couch. I straddle his face, opening my pussy for him, and then lean down to taste his cock again. Tom sits on the arm of the couch, balancing one foot on the floor as he eyes my mouth, knowing it will soon be wrapped around his throbbing cock.

As Dave's cock quivers between my breasts, I take Tom in my hands, gently licking his cock all the way from head to his balls, stroking his balls with my tongue, back up to lick the shaft, tasting myself from when he fucked me earlier. I look up at him hungrily as he licks his lips, eager for me to swallow his cock.

I swirl my tongue around the head, the slit, and plunge down, touching the back of my throat with his head. I slide one hand down, rubbing the cock between my breasts, and briefly lift my mouth off of Tom to lick Dave. Tom pushes forward to get my mouth back, and gets close enough to allow me to take both cocks in my mouth, sliding my tongue between them. I focus on Tom, taking my mouth off of Dave but pumping his hardness with my hand, rubbing him between my tits. I plunge back down on Tom and beg him with my eyes to thrust his hips, to force his cock deeper into my mouth.

I turn to look out the sliding glass door, hoping we're still being watched.

Dave pulled my hips down harder, and I bucked against his face, fucking his mouth. I'm dying to feel Dave inside me again, and beg him to fuck me even harder this time.

He lifts me off of his face, and slides back, positioning his cock under my dripping pussy.

"Right here, honey" he said. He holds my hips, and lowers me to his cock, so I am riding him in reverse.

He pumps my hips up and down on his cock as I continue to suck Tom's cock getting him close to orgasm.

"Fuck, I'm gonna cum," Tom yells, pulling his cock out of my mouth and shooting his cum on my breasts, then aiming for my open mouth.

I reach for some of his cum with my mouth, and lick his head clean, taking him all the way in my mouth again to make sure I get every drop.

"I know where I want you now," Dave says, moving to the center of the couch.

"Room service," we hear as the door opens.

None of us stop what we're doing.

"Right here, Lacy, park that ass right here on my cock," Dave says, reaching for a bottle of lube and sliding a slippery finger in my ass.

"Let's see if we can get your ready for your first DP," he says, guiding my hips down to take his cock in my ass.

I gasp as he enters me, the pain not as bad as I expected, but not yet knowing if I like it.

The room service man, a college kid around 20, brings in a bottle of champagne, "Compliments of a friend, no name, just said he's an admirer," he says. He doesn't leave. He stands there ... watching me move slowly, Dave's cock pegged into my ass. Tom stands off to the side, not wanting to block our admirer's view.

"What do you say?" Tom says to the room service man. "Want a taste of champagne?"

"Um, no sir, we can't drink on the job," he says nervously.

"Well how about this?" Tom opens the champagne, and raise the bottle to our friend across the way and the man nods, raising his own glass.

Dave spreads my legs wide, knowing just what Tom is up to. He pulls me back to make sure he stays inside at a good angle, rocking me back and forth, my anus tight around his swollen cock.

Tom takes a sip of champagne and blows it into me, licking it as it drips out of my cunt. The bubbles tingle as it enters and I jump a little ... I lean back even more, sure to give him plenty of room to work. Dave holds my legs wide, not letting me move them while Tom sucks my clit and Dave gently bumps me from behind, kissing my neck and rubbing my thighs with his strong hands.

"So, do you want a taste, of the champagne or anything else?" Dave asks the room service man again.

"Well, if it's OK with her, I'll have a taste," he says, still nervous but undoubtedly excited.

Tom gets up and pats him on the shoulder.

"Go for it, kid."

He smiles and gets on his knees, taking off his uniform jacket.

Dave moves his hands down to my pussy, spreading my lips for the young man.

"Have you ever eaten a woman's pussy?"

"Well sure, but ..."

"She loves it, really eat her, pretend her cunt is a pie and you're in a pie eating contest, just bury your whole face in her cunt and try to lick the edges of the pie plate with your tongue -- really reach with your tongue."

He gently licked me, then pushed his face into me harder, holding onto my thighs as if his life depended on it.

"He really wants to win that pie eating contest," I joked. Holding his head I bucked again, alternately fucking Dave's cock with my ass, and this boy's face with my cunt.

Tom handed me the bottle of champagne and I took a sip. The cold bubbles sliding down my throat, I smiled at Tom and he knew what to do next.

He waved to our admirer, telling him to join us.