Hotel Club Ch. 02

I woke the next morning in the unfamiliar city, not having slept well from the combination of the long flight, and the crazy evening with the Amazon Cindy. I had never sucked a cock before, and I'd not even had anal sex before, yet last night I sucked a she-male's cock and pumped a giant load of my cum in her ass. All these firsts; it was too much to consider that morning.

I went to the office site and although it took me a while to get up to speed, I was able to start working at my regular pace. The customer was pleased with the work so far, and was pleased to be able to put a face to my name. We got along well, and she asked me if I liked the hotel where I was staying.

With a straight face, I said "Yes, it was really good. I slept okay, you know that first night is always a treat."

She nodded knowingly. "They have some sort of special club over there I've heard. You should ask about it."

"Oh?" I asked, feigning surprise. "What kind of club?"

She shrugged but I caught the scent of a lie. "Not sure. I've never been there. I've only heard about it, you know, from some other people. I guess it's pretty exotic," she concluded.

"Huh. I'll ask, I guess," I said as I did my best to look uncertain. "I'm not much for clubs these days, though."

She laughed. "Honey, none of us are, but like I said, it's supposed to be some special attraction for that hotel. That's why I suggested you stayed there! Maybe you could get in and tell me all about it!"

"Yeah, we'll see," I agreed easily.

By the time I got back to the hotel, it was nearly six and I was just about exhausted. I was hungry, though, so after going to my room and freshening up, I went into the hotel bar and ordered a drink and a meal. I chose a small booth off to the side where I could see the television. It was a novelty to see Monday Night Football on so early, and there was a television in my booth, so I watched as I ate in silence.

"There you are! I hoped that I'd see you again!" a deep but female voice said. I looked up and there she was in all her glory. Cindy. This night she was wearing a simple sundress. She looked really good, with nice boobs and nice legs. If I didn't know what she was packing under that dress, I'd be fetched.

"Hi Cindy," I said. "What's going on?"

"I came here looking for you, hoping to find you. About...maybe one in five guys come back to this bar. Now," she asked in a higher-pitched tone, "I never know if they come back just hoping that I show up again, or they come back because they don't want to go elsewhere. But a girl can hope, you know?" she smiled prettily at me.

"Well, you found me," I parried, "although I'm not sure what shape I'm in, or how I feel about...things," I said evasively.

She slid into the booth across from me without asking. She smoothed her skirt, and looked all the world like she was just another pretty businesswoman at a dinner with a work traveling companion. I was struck by the dichotomy of it - that she could be so different sexually yet project an air of normal femininity. "How do you feel?"

I forked a piece of food into my mouth and chewed slowly. It was a diversion for me to think. The truth was, I didn't know. For certain. I swallowed and replied. "I'm not sure yet."

"What did you think this morning?"

"Confused, a little. But not...not, um, not repelled, I guess is the word."

"Repelled? That's a harsh word. I'm glad I did not repel you!" she said with a soft smile. "Did the recollection of last night entice you?"

I looked steadily at her for maybe thirty seconds, admiring her face, memorizing it. "Yes," I finally admitted. "There were two firsts for me last night, I have to say that, outside of the atmosphere of that club, that I found both...appealing."

"Oh?" With a bright smile, she leaned forward. I could not fail to notice how her large breasts rested on top of the table. "What were the two firsts, and why did you find them appealing?"

"Um." It was hard to say it out loud. "Well, uh, going down on you."

She interrupted in a whisper. "You mean sucking my she-male cock?" she said.

"Well, yeah," I replied in a shy tone. I felt my face heat up and knew that I was blushing.

"Aww. You're blushing. That's cute. What was the other?"

"Anal."

"You've never had anal sex before?"

"No, never."

"Well," she said leaning forward to continue her whisper, "you certainly did a terrific job of filling my ass with your cum!"

I shifted a little in my seat. My penis was alerted to this sexy vixen sitting across from me, and it was rising to attention. "Um...thanks?" I said rather sarcastically.

"Don't be a snide little bitch," she warned me. "You liked it," she added snottily.

"Yes, I did," I sighed. I've never been able to fight well against pretty women and that seemed to extend to those who had male bits instead of lady bits.

"What else did you like?"

I shrugged then. "I can't say much else, you know? It was an erotic atmosphere."

"Yes, it's always that," she said sitting back a little. I noticed how her hand dropped to the swell of her chest. "I like you Roger," she said softly. "You're honest. I can tell."

You can't tell that much, I thought guiltily, as the fact that I was married popped into my head. It was almost like she read my mind, as her soft hand slid over mine and her fingers played with my wedding ring.

"You're honest enough," she amended. "And you're here and she's not. And she's a woman and I'm a she-male. Nothing matters anyway," she concluded.

"I suppose."

"Will you buy me a drink?"

"Yes."

"Do you want it here, or would you prefer it up in your room?" Her eyes bored into me, dazzling, bright, intense eyes suggesting all manner of delights. My penis was now standing at full attention.

I gulped. "How about a bottle of wine?" I suggested. "With two glasses."

"Tell you what," she smiled now that she had won, "I'll even get the bottle. I know the bartender!" she said and slid out of the booth. I paid the waitress on the room tab, and then waited until Cindy returned with the bottle and two glasses; my erection had subsided enough that I was able to leave the booth and walk normally.

We walked to the elevator and rode up to my eleventh floor room. She walked beside me down the hall to room 1117. "Here we are," I said quietly.

A sense of confusion had settled over me again. Confusion at betraying the last thin cords of my marriage. Sexual confusion, to be sure. Yet Cindy's allure was so powerful that it felt right to open that door and guide her in. I closed the door behind me.

She had opened the bottle already and poured two generous glasses of wine. She sat on the edge of the bed, her legs crossed primly, and patted the open spot next to her. "Sit down, Roger, relax. Take your shoes off. Enjoy yourself. There are worse things than spending time with a pretty woman," she said.

I took the glass and sat. "You're right." I sipped the wine. For courage? I don't know, but as we talked quietly about other things, like life in San Francisco, and life where I lived, the wine was consumed, and after maybe an hour the bottle was empty. We were still just sitting next to one another on the foot of the bed.

"It's too bad that the club is closed on Monday nights," Cindy said.

"Yeah, that was hot," I said.

"Any part in particular?" she wanted to know.

Fuck it. "When she was behind him, unzipping his pants, taking his big cock out and stroking it. For some reason that reach-around handjob has always seemed so sexy to me."

"Oh really?" she grinned. "So at least I know my opening move, huh?"

"Well, yeah," I said. At that moment I had brought my face up and turned it towards her. She was already looking at me, and our gaze met. It was a hot, smoky, steamy gaze, full of promise and lust and need. She gave me the tiniest wink and I moved in, and our mouths opened. The kiss was warm, wet and hot, and resulted in my cock stiffening almost immediately.

Cindy's hand found it, and she moaned softly into the kiss. The vibration on our tongues was pleasurable, and her light fondling through my clothes was very arousing and pleasurable. She did her best to grip it, and that resulted in me finally sighing.

"Stand up," she said softly after breaking the kiss. "Let's see if I can give you a third 'first'!" she grinned. I did, and her hands wrapped around my waist, and she locked her hands over my stomach. She pulled me tightly against her body and I was first surprised by her considerable strength. I felt the hardness of her she-male cock bulging between the cheeks of my ass, and I wiggled my hips back into her.

"You feel my cock, Roger?" she cooed into my ear. She was as tall as me, and when she put that massive mane of hair of her head around my ear, all that hair cascaded all over the place. It was soft and fragrant, and her breath hot and sexy on my earlobe. "You like my big, thick cock?" she purred.

I moaned as her hands moved from the waist clench and found my khaki pants. She deftly unbuttoned them, and they fell to the floor, and my erection poked out of my boxer shorts. Her touch was delicate and light, and first she only encircled my hot shaft at the base. Her slow stroke from base to head left me moaning and my legs quivering from the power of the sensations; adding to it was the fact that her hard cock was poking against my ass.

"Does this turn you on, Roger?" she purred softly again. "A big she-male stroking your nice, thick cock? Hmmm?"

"Yes it's turning me on!" I moaned. She used maybe only three fingers but it was enough. The heat of the palm of her hand burned against my rigid shaft and the heat added to the pleasure.

"Imagine if we had any lube," she said.

"I have some," I admitted.

"Oh? Get it," she ordered. I stepped out of my pants and walked into the bathroom; in the bottom of my kit I stored some sexy goodies that I brought with me. I got the lube and brought it back to her.

She had climbed onto the bed, on all fours, looking at me. "Rub my ass, Roger. You tease me now. You play with my thighs and run your hands up them and over my ass. Lift my skirt up and expose my ass to you," she said in a needy tone. She wiggled her bottom for good measure.

After putting the lube down, I positioned myself behind her. I put my hands on the back of her ankles, and ran them slowly up the shapely, muscular calves and over the back of her knee, and then slowly up her thighs. They were soft and warm, and above the top line of the stockings, where bare flesh met flesh, she shuddered. I continued pushing my hands up over her bottom, feeling the soft sexy material of her panties, and with it her dress bottom lifted. The pale yellow panties under her pretty dress looked fetching. I was fetched.

"Spank me, Roger. Spank me and call me a bad girl," she moaned. I could not resist, and turned to the side a little to deliver several quick spanks. There was a loud crack as the skin hit skin, but I did not deliver it with enough force to leave any marks. Just enough to redden the exposed skin of her flesh butt.

"Oh I love it when my guy spanks me!" she squealed. "It makes my cock throb!" she moaned. "Are you throbbing, Roger?" she asked.

"Yes!" I moaned back, resuming the slow massage of her thighs. From butt to knee and back again, and at the top I gave her a few more spanks.

"Oh yes!" she squealed in delight. "That's hot, Roger, that's so hot!" I did it a few more times, and then she rolled over and stood up aside the bed, and in one swift motion removed her dress from her body. She was wearing a full lingerie getup, the matching panties and bra and stockings. The breath was sucked out of me entirely; the sight was legendary. She was exactly the type of woman I lusted after in my fantasies, the full, thick-bodied and heavy-breasted woman of my dreams...with a big, thick cock to match. I knew I had never seen a sexier sight.

She sauntered over to me, and put both hands on my shoulders, and turned me around. She clenched me tight with one hand around my waist, trapping her turgid erection between our bodies. She used the other to open the lube, and pour the cool, thick fluid over my raging erection, and then her hand began stroking me lightly again.

"Oh fuck oh my god oh god," I moaned uncontrollably. Everything about it exploded my need - her arm trapping me tight against her body, her boobs pressing into my back, her cock nestled between the cheeks of my ass, and her hand, her hand and its slow, mind-blowing stimulation of my cock. Nothing had been better; fantasies were not as good as real life, I realized.

She pulled me even tighter against her body. "You're really loving this aren't you Roger?" she cooed.

"Yes!" I admitted with delight. "It feels so good, all of it."

"Even my cock against your ass?"

"Yes!" I moaned again.

She put her mouth next to my ear again, and delivered her next lines in a breathy whisper. "I'm going to take your boxers off soon, Roger. And then I'm going to take my panties off. And you'll feel my thick cock pressing against your asshole."

I quivered as uncontrollable lust imprisoned my body and mind; that was answer enough for her.

She released the clench but not my cock, and I felt her step away. I did not want to look. She then tugged at my boxers, lowering them from my body. "Feel this, Roger," she said. The pressure of her hot, throbbing cock against my asshole triggered another rush of lust.

"Push it, Cindy, push it against me."

"You want my cock in your ass, Roger?" she asked.

"Yes! Fill my ass with your gorgeous she-male cock, fuck me, Cindy, fuck me!"

"I've never heard better words!" she chuckled. She used generous amounts of lube, and then held my hips firmly with her hand. She used the other to guide her beast, and the thick head was pressed against my tight asshole. The lube made it easy for it to push in but then its girth was met by my body's resistance. "Shhh, relax," she advised as she pushed harder.

I reached back and grabbed an ass cheek, spreading it wider for her. "Go ahead," I whispered. "I can't wait to feel that cock in my ass!"

She shoved; her cock penetrated fully; I howled in pain. We stood there for a few seconds until the sensations of the penetration died down, and then she began sliding it out. "Oh my...god..." I moaned. She used more lube, and slid it back in balls deep. I felt like had a massive sausage stuffed up there. After withdrawing and adding yet more lube, she pushed in again.

Between my legs, my cock felt impossibly hard and yet funny, like I had to pee, as her cock slid past my prostate. It was a new sensation, not good nor bad, but all the same added to my slide into pure lust.

"There we go," Cindy finally said. "And now, for a good ass-fuck!" she said. Both hands gripped my hips, and then I was treated to a muscular, powerful slam of her hips, driving that beast deep inside of me. All I could do was whimper, but I didn't want her to take it out.

She began thrusting hard, deep and rough. My cock leapt, driven forward and back from Cindy's hard actions. Her balls slapped against my ass, meeting my swaying balls. Cindy's breathing picked up pace quickly. "Oh god Roger I'm gonna cum!" she moaned. "I'm gonna fill your asshole with my hot sticky cum, Roger, oh Roger I'm cumming!!"

The final thrust was almost the most painful of them all, but then I felt the pulsating of her cock and my insides felt thick and slippery as I was filled with shemale cum. Nothing had felt better, and then nature took its usual course, and her cock went flaccid and slipped out. She was behind me, and slurped up the cum with gusto. "I love eating my cum from a man's ass," she moaned, spreading my legs to get better access. The sensations were pleasurable, not as great as having my ass filled with her cock, but pretty damned good anyway.

Done, she made me sit back down on the bed. She knelt on the floor in front of me. "I'm going to make you cum in my mouth, Roger," she told me. "I'm not going to swallow your huge, thick load. As soon as I'm filled up, I'm coming up for a big kiss and you're gonna share eating your own cum."

"Good, do it, hurry, I need to cum!" I moaned. At that moment, nothing in the world sounded more appealing.

The amazon took my cock into her mouth again, and as she had the night before, teased it to girths I'd never experienced. It felt huge, thick, and just bursting with cum, and then finally the orgasm arrived. I cried out loudly as my cock jetted streams of thick, gooey cum into her waiting mouth. She put her hand on my cock and jerked fast, getting every last drop out, and then she stood up.

The cum was dripping from the corners of her smiling mouth. She put both hands on my head, and brought her face to mine. I didn't care, and opened my mouth; she slippery mess slid from her mouth to mine, and mixed with her tongue and kiss and I swallowed and it was glorious, it was the best tasting thing ever. We kissed and kissed, and she pushed me back onto the bed and climbed atop me, still kissing. I wrapped my arms around her thick, strong body and pulled her close to me, enjoying the pressure of her bodyweight on me, pushing me into the bed.

Finally, the kiss broke and she rolled off of me. "That was some kiss, honey," Cindy said in admiration. "You're pretty good for a first-timer."

"It's gotta be you, Cindy. I've never been like this before."

"Hmmm." She smiled prettily at me. "I'd like you to do one more thing for me?" she asked nicely, her fingers tracing gentle lines over my face.

"Sure."

"Wear these panties until I see you again tomorrow night?" she suggested.

"With pleasure."

"Don't masturbate into them," she warned.

I grinned. "I won't. I think I'll be falling right to sleep."

"Perchance to dream?"

"One can only hope."

"Tomorrow, then, same time, same place." She dressed and left; I fell into a deep, satisfied sleep...wearing her pale yellow panties.