A Frank ConversationbySquiresBoy©
She was sitting at the bar, dressed like a nun compared to the majority of the other women around. It was Vegas, baby, and the outfits ranged from the slutty to the half-naked. The woman I was interested in, and maybe it was the outfit that did it, was all business. Charcoal black suit, white blouse open at the throat, blazer draped over the back of her stool. Her long, muscular legs were crossed at the knee and the high heel of her dangling foot kept slipping off and revealing the back of her foot. Okay, you got me, I have a thing for feet.
I got up from my table and made my way over to her. I signaled the bartender for a drink and, over the chimes and bells of the surrounding slot machines, said hello to her.
She was in the middle of taking a drink, so she looked at me over the rim of her glass. She put the glass down, sucked her top lip into her mouth and tilted her head to one side. "Hello."
"What are you drinking?"
"Are you offering to buy me a drink?"
I smiled. "Don't tell me I'm the first to offer."
She laughed and pinched her straw between her thumb and forefinger. "Okay. We're in Vegas, right? Why pull punches? Let's be frank and upfront about this from the very beginning. Okay?"
I shrugged. "Why not. When in Vegas, do as the vegans do, right?"
She sucked the moisture from the pad of her thumb and said, "You want sex, right? That's why you came over here. You're not looking to begin a long, fulfilling relationship, you just want to get laid."
"Nothing wrong with that?"
"Oh, no! No, not at all." The ice cubes in her glass clinked together as she stirred her drink. "Let's up the ante then, all right? You're looking for a blow job. You want to see me naked. And if I let you, you would fuck me in the ass. Right?"
I was trying my best not to blush, and also trying to angle myself so the bulge in my trousers wasn't apparent. I coughed into my fist and lifted a shoulder. "Sure. As long as we're being candid."
She turned on her stool, put her elbow on the bar and rested her chin on her fist. I inadvertently glanced down and saw the way her dress rested on her thighs, the material of her stockings. She said, "What would you be willing to do? To be with me tonight, all night."
"What did you have in mind?"
She looked past my shoulder and nodded with her chin. I turned and looked into the crowded rows of slot machines. "The man in the gray suit, blue shirt... do you see him?"
I had to look for a moment, but then I saw him. A little taller than I was, dark hair cut short to his scalp. He had wide shoulders and a strong jaw. He was focused on the slot machine. I nodded. "Yeah." I wondered if she was a prostitute and he was the man I was supposed to pay.
"I want you to fuck him."
I looked back and her and frowned. "Say what?"
She smiled. "A threesome, cowboy. You, me and him. But I want to watch the two of you first." She uncrossed her legs and moved to the edge of her stool. She put her hand on my thigh, the other sliding across the bar to cover my hand. "You do what I say, when the time comes, I'll let you fuck me. However you want, as long as you want. I'm sure that, given a good enough pre-show, I'll too horny to say no to anything."
I swallowed. I looked back over my shoulder at the man she had indicated. Was he just a random guy pulled out of a hat? Was it a test to see if I was willing and, if so, would a yes answer led to a drink splashed in my face and a shouted curse about me being a faggot? Then I would not only lose her, but any other prospects in the bar. My night would be shot. When I looked back at her, my eyes focused on the open collar of her blouse. God, why must I be such a sucker for a woman in a suit?
"If that's what gets you off," I said. "Sure. I'm game." I had never been with a man before, but I had to admit there were times I had thought about it. Never enough to do anything about it, of course. But I was curious. And for the bombshell sitting in front of me offering the moon, I decided maybe the time had come to see how far I could go.
She quirked an eyebrow and said, "Really? Well. I must say, I never expected to get a yes." She straightened on her stool and turned to her drink. Her hair was pulled back in a loose ponytail and I noticed the shell of her ear was bright pink. Looks like I wasn't the only one taking a shot tonight. She finished off her drink, motioned for the bartender even though he seemed too preoccupied by the blonde wearing cocktail napkins as a dress to have brought my drink yet.
I was horny, but my mother had raised a gentleman. I could tell that she was suddenly uncomfortable. Maybe she had just been trying to get rid of me. What kind of guy says yes to "the devil's threesome"? I said, "Hey, look. If you want to back out, I understand. No hard feelings."
Her head snapped back to me. "Oh, no you don't. You're not getting out of it that easy." She dropped a fifty on the bar, took my hand and slid off her stool. She took her blazer off the back of the stool and led me out of the bar. She led me over to the man by the slot machines and she got his attention by sliding her hand from his shoulder to his elbow. He turned, smiled at her and looked at me with interest. "Hey. Look what I found."
He looked me up and down. Describing him, you may have pictured a high school football coach or something like that. Unfortunately, I was nowhere near that category. I'm no schlub, but I felt like a ninety pound weakling under his appraisal. I'm about five-ten, he looked to be six feet. I was average weight, I doubted he had an ounce of fat on him. He was in that game-show-host suit, I was wearing khakis and a button-down blue shirt. Not exactly a catch. But he must have seen something he liked, because he smirked and said, "Nice job, Amanda. I'll finish up here, and meet you up in the room."
"Okay," she said. She stepped closer to him and stretched up to kiss him. She still had my hand wrapped up in hers, so I couldn't exactly turn my back to the scene. Not that I wanted to. I took the opportunity to look at her ass, the shapely curve unmarred by panty lines. I licked my lips as she broke the kiss and brushed her hand down his chest. "Don't be long."
The woman, Amanda, apparently, led me away from the slot machines to the elevator. She reached into the pocket of her blazer and withdrew a room key. As we waited for the elevators, she turned to me and looked me over again. The cocksure woman who had suggested the terms of the evening was gone, replaced by a woman nervous about having her fantasy come true. She looked me in the eye and said, "Well, I suppose introductions are in order. I'm Amanda, that was my husband Richard."
"Nice to meet you, Mike." The elevators arrived and we stepped into the car. A few other people joined us before the doors closed and we ended up in the back corner. She was standing slightly to my right, her hip pressed against mine due to the crush of people. I moved slightly so I was directly behind her. I wrapped the arm closest to the wall around her hip, pressed my hand to the front of her skirt and pulled her back against me. She gasped slightly when she felt my erection against the crack of her ass. She turned her head slightly, smiled and twisted her hips against me.
It was all I could do not to come right there.
We reached the ninth floor all too soon and we were forced to separate. I followed her to the room, watching the way she walked and knowing she was dripping wet. She swept the keycard into the slot above the door, pushed it open and backed into the room. She pulled me inside with her, breathing hard as I kicked the door shut behind me. The room was pitch black and I took the opportunity to kiss her, press her against the nearest wall and run my hands over her body. Her breasts were full and firm, and I pinched the nipples through her blouse.
She gasped and arched against me, one of her legs slipping between mine. I moved my hands to her ass, got a good grip and pulled her to me. We kissed as she rocked against me, riding my thigh. Her tongue was in my mouth, her hand working my belt as I kneaded her ass. I was just beginning to think that the threesome offer was a test after all when the room was filled with light from the hallway. It was a brief glow, quickly cut off as Richard came into the room and shut the door behind him.
With her pussy warm on my thigh, her hand cupping me through my boxers, I was too turned on to care when Richard pressed against me from behind. I felt his cock against my ass just before he started to grind against me. Then his hand was over mine, and he pulled Amanda even closer, pinning me between them in a sandwich almost too tight for me to breath.
Amanda broke the kiss and said, "Okay, okay. Calm down, boys. Let me go."
We released her and she leaned back against the wall. My eyes were adjusting to the dark, the lights of the Strip seeping through the curtains, and I saw her wipe her mouth. She withdrew from my thigh, tugged her dress down and straightened her blouse. She walked to the bed on unsteady feet and sat on the edge of her mattress. She pushed her hair out of her face with the back of her hand, exhaled and touched her tongue to the corner of her mouth.
She crossed her legs again, this time to take off her high heels. She ran her hand up her calf and said, "I believe we had an agreement, boys."
I looked at Richard. He had his jacket off, his tie loosened. He was undoing the cufflinks on his shirt and I couldn't help but look down at his crotch.
"Wait," Amanda said. We both looked at her and she said, "You were a gentleman earlier and you were willing to walk away when I looked uncomfortable. I'm giving you the same chance right now. You can go if you want. If you're uncomfortable at all, I don't want you to feel obligated."
I was grateful for the escape opportunity, but the truth was, how could I possibly leave? The option was stay here, go through with it, and have possibly the best sex of my life, or go back to my hotel room now and masturbate to some movie on Pay-Per-View. Been there, done that. Besides, how would I ever live with myself if I left now? I shook my head and turned to face Richard. I was breathing hard, and wondered if I was horny enough that it wouldn't matter that I was about to do what I was about to do with a man.
"How far are we going?" Richard asked quietly enough that I knew he was asking me and not Amanda.
"As far as you want. Just... go slow."
He nodded and stepped closer. One hand went to the back of my head and he brushed the other down my chest. It slid over my stomach, to my belt, to the bulge his wife had started. He cupped it, squeezed and then leaned in. His breath smelled like liquor and he hesitated just before his lips met mine. It was a chaste kiss, if I could ignore his hand gently massaging my erection, and I kept my eyes open throughout.
His tongue gently probed my bottom lip and I opened my mouth to him. He stopped rubbing me, moved his hand to my belt and slipped his hand into my pants. I have to admit, a part of my brain rebelled at the thought. I was standing there with a guy's tongue in my mouth, his hand moving ever-closer to my cock. I needed a quick shot of heterosexuality, so I looked to my left to see what Amanda was doing.
That business skirt that had first drawn my eye was pushed up. Her hand was between her thighs, the muscles of her arm showing that she was furiously working herself. She had unbuttoned her blouse to reveal the lacy top of her slip. My cock twitched just as Richard closed his fingers around it. I gasped into his mouth and he groaned. I decided to help him out. I moved my hand between us, unzipped my pants and grabbed a handful of the material. I tugged, and they fell to the floor.
Richard pulled his hand away from my cock long enough to push my boxers down. My shirt was long enough to cover me, but I suddenly felt completely naked. Richard returned his hand to my cock and I was aware that it was a warm, soft hand that was currently stroking my cock from base to tip. When he reached the head of my cock, he brushed the thumb over the tip and I shuddered. I started returning the kiss with passion now, focused entirely on the hand on my cock, the tongue in my mouth, the warm body pressed against mine.
We broke the kiss and he backed up, looking down at my cock in his hand. I'm no giant, and there's a reason I never even considered a career as a porn star. My cock is nice. Not too big, not too short. I've never had any complaints. But right then, with another guy looking at me, I suddenly felt very inadequate. I looked at him, then across the room at Amanda. She was breathing hard, but managed to say, "Take off his shirt."
I thought she was talking to me, and Richard thought the opposite. We both went for each other's shirts and hesitated. Amanda said, "Undress each other."
My hands were shaking as I undid the buttons of his shirt. He pulled the tie over his head and tossed it toward the bed. When I got the shirt off, he shrugged out of it. The suit had definitely done him justice. I stared at his shoulders and chest and wondered if there was any way to keep my shirt on for the rest of the night. But he had already finished undoing the buttons and pushed it off my shoulders.
He moved his hands down my chest. He must have felt my heart beating, because he hesitated before he continued his downward trek. He cupped my balls with one hand, gripped my cock with the other, and looked into my eyes. He stroked me slowly and then bent down. He kissed my neck, my chest, and then knelt in front of me. I swallowed hard and looked at Amanda.
She had moved to the edge of the bed and her shirt was gone. She had lost her dress, leaving her in just a slip and stockings. If I thought she was gorgeous in the suit... I groaned as Richard ran his tongue along the top of my erection from head to base. He turned his head, kissed the side of the shaft and then pulled back. I felt something wet on the tip of my cock. It swirled, then enveloped me and I gasped when I realized he had taken me into his mouth.
I closed my eyes and rolled my head back. He took me completely into his mouth (like I said, I'm not shrimp but I'm nowhere near a porn star) and rolled my balls in his hand like a pair of dice. Then his hand moved between my legs. I had no idea where he was going, but I was willing to go with it. He rubbed the space between my balls and ass, then pushed one finger between my ass cheeks. My eyes flew open as he circled, then penetrated my anus with his middle finger.
Suddenly, a pair of hands slid over my chest and I was embraced from behind. I felt Amanda's breasts against my shoulders and I turned my head. Her eyes were half-lidded with arousal and I kissed her as her husband tongued the slit of my cock. I thrust my hips gently into his mouth and his finger worked slowly in and out of my ass. The warm, definitely female, body pressing against me from behind was just what I needed.
Richard finished sucking me, pulled back and watched as his wife's hand wrapped around me. She stroked my cock, wet with his saliva, and looked down at him over my shoulder. "Stand up, Dick." At first I thought she was talking to my penis, already as "up" as I thought it could go. But then Richard stood up. She undid his pants, unzipped them and fished out his erection. Lord Almighty, and I was embarrassed to have my chest compared to his.
Amanda wrapped her fingers around it and pulled him forward like a dog on a leash. When his cock was even with mine, she brought her other hand around and gripped me. She pushed our erections together, laced her fingers on the underside of the shaft, and said, "Thrust. Thrust..." I thrust forward and he thrust backward. Our cocks, captive inside the bowl of her hands, rubbed against each other. My head rolled back onto her shoulder; I had never felt anything like it.
We continued with this dance for a few seconds, smearing pre-come on each other's erections, before she released us. I continued to thrust, rubbing my cock against his, before I realized I was free. But I didn't want to stop. I reached down, squeezed his cock and watched as it jerked in my hand. For the first time in my life, I thought about putting a cock in my mouth.
As it turns out, I didn't get a chance. Amanda was far too hot. She stepped back and said, "Bed?"
"Yes," Richard said. His voice was rough with arousal. Amanda took my hand and led me over to the bed. She sat down on the edge, spread her legs and brushed her hands over the bare skin between the top of her stockings and the hem of her slip. She lifted both legs, planted her feet on the mattress and laid back. "Come on," she said. Her breasts were rising and falling with each breath and I knelt between her open legs. I pushed her slip up, looked down at her pussy and my cock gave a grateful twitch.
I lowered myself on to her and kissed her hard. It was quite possibly the most passionate kiss I've ever had, since it was partially an attempt to prove my masculinity after having another man's finger fucking my ass. I reached between us and gripped my cock, touched the tip to her wet labia. She groaned, squirmed against me and lifted her hips. I took that as an invitation and pushed my head into her pussy.
She was tight, wet and ready for me. Who wouldn't be, after the show we had just put on for her? I sank into her, my eyes closed and my jaw dropping as I finally got what I had lusted for since ordering my first drink in the bar downstairs. I put my hands on either side of her, clenching and unclenching my fists in the sheets. She looked up at me, smiled and rolled her hips. I groaned. "Oh, fuck..."
Again, Richard surprised me. I needed to stop forgetting the guy was there. He crouched on the bed behind me, his knees between mine and his wife's feet. While I had been getting my first feel of her wrapped around me, he had been getting undressed. I felt his naked flesh against my back and hips, and his cock came to rest between the cheeks of my ass. Due to the unnatural, smooth feel of it, he was wearing a condom.
I bowed my head and kissed Amanda. Richard reached around me and circled my cock with his fingers. He stroked me when I pulled out of her, spread her labia when I pushed back in. He found her clit with his thumb and brushed it, and she began to moan into my mouth, around my tongue.
I saw so intent on fucking her, on kissing her and watching her breasts against the smooth silk of her slip, that Richard pushing his cock into my ass was a complete shock. My spine went straight, my knees dug into the mattress and I hissed, "Jesus Christ..."
Richard moved his hands to my hips. I looked down at Amanda's breasts and focused on them as he pulled out, then pushed back in a little at a time. I put my hand on Amanda's breast, pulled down the material of her slip. She shrugged her shoulder out of the strap and her breast was revealed to me. It sagged naturally against her torso and I cupped it in my hand. Big, natural, beautiful breasts with beautiful brown nipples and... oh, fuck, Richard's cock nudged my prostate and I pinched her nipple between my thumb and forefinger.
"Harder," she grunted. "Twist it..." I did as she asked, grateful she didn't expect me to be gentle. When I pulled my hips back, I pushed Richard's cock deeper into me. When he thrust forward, he pushed me deeper into Amanda. We worked up a smooth, steady rhythm and I bowed my head to Amanda's neck. I nuzzled, licked, sucked and bit, grunting a little every time Richard thrust into me.
Amanda ran her hands over my body, my chest and my back, down to my hips. She dug her nails into my ass pulling me into her. She kissed my ear and said, "Do you like that? His cock in your ass? Fucking you while you fuck his wife? Huh?"