Hotel Club Ch. 05

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Roger returns to San Francisco.
7.2k words
4.83
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Part 5 of the 5 part series

Updated 06/08/2023
Created 11/29/2016
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I woke up from a fitful night's sleep. The slow, soft, wet and sloppy blowjob I had given Cindy did not improve my mood, not after the fight with my...wife? Ex-wife? I sat up in bed and rubbed my face hard. The increased blood flow felt good but did nothing to quell the rising anger.

I showered angry. Brushed my teeth angry. Dressed angry. Ate breakfast angry. And when I got to the office I was brimming with hostility, ready to lash out at anyone. The first person to see that morning was the boss, and she poked her head for a quick sit-rep. Wisely I did not lash out at her. I provided it but could not hold back the short, bitter tones in my voice.

She looked at me, noting the hostility. "What's gotten into you?" she demanded. "By your own admission you're only a good day's worth of work away from that bonus!"

I bowed my head and breathed steadily and slowly while counting to twenty. I lifted my head. "I had...it was a personal issue last night. Bleeding into today. Don't worry," I said holding my hand aloft indicating that I should finish because she looked all the world like she was going to interrupt, "it won't affect my work. I'll be done by 5PM today."

She gave me one of those long considered gazes. Rather than opening that can of worms she simply nodded and left. I stood and looked out the window, at my phone, out again, phone again, and then sat down. I gave a mighty sigh, and then started calling up software and files.

Thankfully I fell into the work quickly enough and worked steadily straight through until three PM. No breaks, no coffee, no food - I think that my barely-contained fury fueled my work. I finally handed over the keys to the project to the boss. She whipped through it quickly and then demanded that her staff start hammering on it. By five her staff had announced that it was working to specifications.

"Well, I suppose that you earned that bonus," the boss said. "Are you still in a sour mood?"

"Yes," I told her. "Not much is going to change that. Not when..." I inhaled deeply. "Not when you were told that you're going to come home to an empty house. God only knows what she's left me with."

"Oh," she said sounding immediately contrite. "I didn't mean to pry."

"No one does until the other person drops the TMI bomb on them." I held up my hands. "I don't know, what are you going to do."

"Well..." she said slowly, "with as hard as you worked, if it really all has gone to shit, let me know. If I can't find you work here, I'm sure that I could get you a bunch of leads on work."

"Thanks," I said with a rueful chuckle. "I might need to take you up on that." I shook my head. "I don't know what's next."

"Keep me in mind," she said. "A man of your talents would be in demand in this city."

Later, after packing and leaving, and finding myself sitting at the airport pondering a very uncertain future, I turned the phone over in my hands. Over and over, an obsessive motion. Should I, shouldn't I? Finally, after uttering a barked but quiet "ah fuck it" under my breath, I dialed Cindy's number. It rang but she did not pick up.

"So," I said with some hesitation, "it's Roger. I'm flying home. Thought I might catch you. Have fun." There was a pause, and in retrospect he wished his voice had not sounded so bitter. "Can't imagine how I'd see you again. Anyway. Bye." He hit end.

By the time I got home, it was nearly midnight local time. I pulled into the garage, and after cutting the car engine peered around. Nothing seemed out of place, but then again the garage had always been my domain. I pushed through the door entering the home through the mudroom, from which there was vantage point to the home's dining room. A dining room, I noted instantly, that was missing its table and chairs. "Fuck," I breathed softly as that leaden ball of anger and worry exploded. As I walked into the house all I saw were signs of a hasty exit.

Kitchen cabinets left open, the shelves bare. Well, there were two glasses left, both of which were from some beer garden I'd bought them from long ago. The fridge was completely empty, as was the freezer. The sofa, gone. The television, gone, only the cable wires left dangling uselessly from the wall. The floor lamps, gone. I trudged up the steps into their master bedroom. Slowly: "Of fucking course she'd take the bed." My clothes were piled into a great heap in the corner, covered by coat hangers tossed every which way. The only piece of furniture left in the room was my rocker, a hand me down from my grandfather.

The closets, bare, looked huge. When they were filled with our clothing, the battles over space were constant. I moved into the spare bedroom. She'd left the bed in there, but - naturally - had pulled all the covers and sheets leaving a bare metal frame supporting a bare mattress. Having no other option, I flopped down on it and stared abjectly at the ceiling, my mind going and not going. I stayed there deep into the night until pure exhaustion took me. Sleep was thin and poor.

Rising from sleep to wakefulness the next morning began with confusion. Then as recollection returned, anger. I paced, his steps thumping along bare floors. I had forgotten where I put my mobile phone the night before and furiously wondered how in the fuck one could lose one's cell phone in an empty fucking house? Finally I found it and opened it. One new text message.

Cindy: Call me anytime, Roger.

Yet in the chaotic months following I forgot all about that message. And the illicit shemale sex, the domination and the pleasure of submitting to it. I forgot all of that. Instead I chose obsession over other things, like "winning" the divorce. Once I got it through my thick skull that it was not winnable I opted for a different manner of attack. I got into shape. I rationalized that nothing would irritate her more than showing up at the final settlement conference sporting a body of a twenty-something, especially after all the years she had nagged me about my weight and health. Plus she had gotten fat so this was going to be icing on the cake.

I entered that final meeting wearing skin-tight clothing showing off a flat stomach and broad chest. I saw the shock in her eyes, but only for a fleeting second. She matched my cold expression with one of her own. But still, that second of bared emotion was enough for me. I had won, and we both knew it.

That night I went to a local neighborhood bar that had served as my unofficial therapy site. The regulars, who now knew me, bought me a shot to celebrate my freedom. Another regular, a younger twenty-something gal, used that night to transition from giving me the expressive eyes to making her move. She was neither good-looking nor bad-looking, and so far I'd avoided conversing with her. It had nothing to do with the marital situation; after all, I'd fucked Cindy while still being married. It has more to do with wanting to be careful, and when I realized that she was practically offering herself to me, my concern grew deeper.

Yet that night came when I finally agreed that taking her home was a good idea. She damn near ripped my shirt pulling me into her apartment, into her embrace and into her kiss. But even that felt a little desperate to me. Later, as I gazed down at her naked back and wide, white butt, looking at my erection sliding into her wet sex, I had a vision of Cindy. This first true sexual activity with another woman did not bring to mind visions of erotic pleasures with women, but erotic pleasures with a woman sporting a bigger cock than mine. The resulting brain cramp left me unable to achieve a climax.

Both parties left that tryst disappointed but for very different reasons. In that aftermath I began reviewing my life. What the hell was keeping me here? Nothing. Yet it took two more weeks of "careful deliberation" before I admitted the decision to myself that I'd make in about two seconds: time to go to San Fran.

About a month later, I paused for a moment before slamming the rolling door shut on the box truck rented to move me across the country. The amount of belongings felt meager, yet I felt a certain lightness in knowing how little I had to move. The destination, a cramped and older apartment in the city was barely affordable given my new job, but despite it's seediness had a certain charm to it. And it was close to work, and my old boss Amanda had assisted me landing that job. My last act in my old home was to call and have flowers sent to her.

Yet once in San Fran, I found myself immersed in this new challenging job and once more lost track of time. My life became a series of routines - waking, showering, riding a bike to work, working through lunch, a ride to the gym for a nightly workout, a stop at a local grocer on the way home to get that evening's meal, and then to cook, consume, clean and fall exhausted into bed. Six months passed, and even though I was in the same city as my long-ago shemale lover I'd not thought of her.

Until a meeting brought me to the tall office building across the street from that hotel. The hotel where I'd met her. And been introduced to her life. This being a Wednesday and happy hour was just beginning, and with a dull ache permeating my body telling me that I was working out too much I decided a night off from the gym was in order. I paused, looking at the hotel, wondering whether I should text her back. But I knew the bar, and the club in the bar. I walked in and looked around, and since I did not see her I found a stool at the bar and ordered a drink.

As conversations bubbled noisily around me I took solace in revisiting the memories of that strange week. I also found that for the first time since being in San Fran that my cock was alert and awake. Between fond memories of exotic sex questions bubbled up - would she remember me? Would she want me if she did? Would she be angry at me for never calling? Then some hot little image would blot out such worries, and my penis would stir to life in my khaki pants.

I waited. Then waited some more. Just when I was done waiting, I thought why not wait longer? But before long the inevitable conclusion was reached - she was not coming. I took my phone from my pocket, turning it over in my hands. I would look at the text call me anytime, Roger and wondered what had stopped me? Finally, having no other recourse, I paid the tab, jammed the phone in my pocket and rose to leave, my shoulders slumped in disappointment.

"Oh my god. Roger!"

My head, having been down, locked onto those heels and hosed feet. My eyes rose swiftly up long legs to the sturdy hips that supported that lovely cock. Her wasping waist leading up to the expanse of her breasts. Then to her pretty face and smoking eyes - whether glinting in pleasure or anger I knew not.

"Hello Cindy. Been a long time."

"You're right. It has. You never called me," she pointed out.

"I know. I'm sorry," I said properly admonished.

She made a pointed look at my left hand. "No ring," she commented.

I agreed with her. "Divorced about seven months now."

"Happier?"

"I suppose. I've been too busy to worry," I explained.

"I see. I missed you," she said quietly. It was how she said it, leaning forward a little, suggesting that her words were for me alone.

"I missed you too. I came out here...as much because of my memory of you as wanting to escape...my old life," I admitted.

"A memory of me?" she asked, smiling and flattered.

"Yes. It was the first time I was with a woman - a woman I probably should not have agreed to go to bed with - but instead of seeing her, feeling her...I was seeing...and feeling you," I said.

"Hmmmm." Her pose suggested that she was angered or holding some distance, but the twinkle in her eyes conveyed a different message. "How did that realization make you feel?"

I chuckled, the tone a mix of rueful and bitter. "Well, two, three weeks later I was on the road here," I informed her. "So I suppose," I continued in a brighter tone, "that it was sufficiently pleasant and powerful to entice me to return."

Her smile returned, wide and sunny. "Well, isn't that interesting!" She patted my arm lightly, and just that non-sensual touch resulted in a lightning shiver ripping from the base of my spine up to my head. "I feel...flattered," she said. Her fingers lingered on my forearm, and she took a moment to study him. "You've lost weight," she decided.

"A lot of gym time," I agreed, "and a better diet."

"Oh yeah. That'll do it." She paused, once more giving me a thorough up-and-down. "You look really good, Roger."

"Thank you, Cindy. You've not changed a bit."

She grinned. "You think?" She executed a slow turn, and my eyes locked onto the curves of her body.

"Yes, I think," I agreed, smiling.

"Well, I think you've earned a trip to the club with me, dear!" she grinned. She patted my elbow, which I had wisely offered. After hooking her arm into the crook, we walked into the club, protected by the same huge Hispanic man who gave us both the same disinterested grunt as we passed.

Once inside, Cindy guided me to a spot near the back. She patted my arm. "I want to have some fun with you Roger," she informed me mixing her prim tone of voice with a wolfish grin.

I smiled back. Already my cock was stirring - no. Already it was hard. Soon it would be raging. "Please do."

"Well then," she said, sliding one foot forward, angling her foot so that the heel lifted off the floor and her toes pointed down, her leg bared and tensed, "kneel and beg my forgiveness for failing to call me!"

I dared shoot a big grin at her, if only for a second or two. "Yes, Mistress," I said and got down. Pressing my lips to her heeled feet did not bother me; in fact, it deepened my sense of anticipation. Having been in the club before I knew that others were going through similar circumstances.

She made me worship her feet for a few minutes before hauling me up. I was made to strip naked and then don a pair of satin bright pink panties. I mean bright pink - nearly fluorescent in hue. I was already hugely erect so sliding those panties on my legs did not improve my erection but ensured it remained huge.

Her hands on my shoulders, she pressed down and I sank to my knees. Now that she had me wearing the feminine attire, she withdrew her shemale cock. It was thick, full and looked delicious. I looked up at her; she gazed down, smirking.

"Please, Mistress, may I suck your cock?"

She smiled widely. "Before you do," she said handing something to me, "wear this." I took it - emblazoned across the front in all caps, pink letters was the word SLUT. And when it went over my eyes, I was unable to see.

"Now you can worship me." Her voice, a soft, throaty whisper, spoken in a volume that only I could hear.

I lifted both hands, and found her bare thighs. The heat of her skin transmitted, the smooth silky texture, and even the little tremor in the muscles were all detected. The girth of the thighs were impressive, and my hands slid upward slowly and naturally.

Sounds assaulted me. The sounds of pleasure, of soft gasps, low moans, guttural growls. Slapping noises in rhythm. Soft whimpers, pleas - words of distress but tones of need. A soft thumping beat, music pumped into the club.

Aromas were next. Cindy, her body, her scent. Musky and deep, and enticing all at once. Never had a smell similar to it. An earthier scent, leather, perhaps.

But touch, back to touch, my head bending backward, hands sliding up as the trembles increased. The sound of her breathing quickening. My hands finally touched her, touched her glorious shemale cock. The organ throbbed like any man's except it was not on any man's body. One hand, sliding and encircling the base of her cock, testing its steely hardness, savoring the supple texture of the skin. The other hand, sliding around to cup her firm, strong ass. Smooth skin over rippling muscle. My head, tipped back, my tongue out, flattened back down to press to my chin.

Touch. Contact. Searing heat, smooth texture, velvet smoothness over the erect flesh underneath. Her sharp inhale, deep, instant and reactive. "Oh yeah right there," she cooed softly. My tongue found that spot, and circled it, teased it. Tip of the tongue, flicking the little spot of her shecock. Flicking circling teasing preparing. Using my hand, pulling the cock down, and my lips pressing to the head. My body shaking, once, another bolt of lightning dancing along my spine. My jaw opens, and the hot thick invader filled my mouth. So thick, hard, delicious. My tongue flinding the head and circling it, slowly, feeling now Cindy's hands fall to my shoulder, her fingers squeezing.

My hand stroking her, my mouth sucking her. My tongue soaking the cock, and my head began to move, to bob. Down, down...slowly, the tongue stuck under the shaft, until I could go no deeper. Clasping the lips around the shaft, sucking hard, moaning deeply. The vibrations pleasing us both. Then, a release, as slow as the descent, leaving in its wake a wet, slick pole of flesh. My hand, at the base, rose and slid now more easily over the shaft, and I stroked.

Slowly, in my mind. `One Mississippi...two Mississippi...three Mississippi..." The head of her organ never leaving my mouth, the hot wet tongue pressing into the tiny hole. Dimly I felt her squeeze on my shoulders, thinking it was involuntary. An idle, random thought - am I a slave to her cock, or is she a slave to my pleasure? Does it matter? Stroking, faster now. Wanting her.

Opening, pulling back. "I want you cum!" I moaned.

"You're gonna get it," she replied just as urgently. I moaned, and engulfed the head again. My hand, tight over the thick tool, stroking stroking stroking. Her breathing, fast and hard. Soft "oh fucks, oh fuck Roger, oh fuck such a good cocksucker!" Her words that should have been demeaning turning me on more. My own cock, throbbing with a hardness beyond measure, yet in a way forgotten. My entire focus, mind, soul, being - focused on her shecock. On pleasuring her. On drawing out that thick orgasm.

"Oh baby here it cums, Roger, you're gonna make me cum, baby get ready oh oh oh baby!" Her last word trailed off. My stroking, hard, fast, detected it first. The way the balls seemed to swell for a second, just a second. Her body, tense, rising in tension, suddenly relaxing, and with it a great grunt.

The hot, sticky cum filled my mouth suddenly, its force shooting down my throat. There was no time to gag because the second pump refilled it. Greedily I swallowed, searing sticky slippery delicious cum slipping down my throat into my belly. Heating it. More of it, I needed more. Moaning on the shaft as it shot, and shot. Each time filling my mouth with the texture of her cum. Each time swallowed wildly with haste and pure need.

Finally, a relenting of the orgasm. Cindy, thrusting me away, her body sagging, her voice soft. "Oh god you're amazing," she said softly. To reply I ran my tongue over my lips, smiling, the taste of cum strong. Overwhelming. Not bad. Not wonderful. But not bad either.

"That was quite a show." This voice, soft, musical, feminine. My ears perked up instantly. I knew that voice. Didn't I? "Turned me on."

"Roger darling?"

"Yes Cindy?" I asked.

"Fancy another big load of cum?"

I gulped. "Yes. Yes please," I added.

A pause. No sound. Were there whispers? I did not know. Then, a step, and a hand, atop my head. This hand, smaller, narrower, more feminine. My hands rose, finding thin thighs yet still supple, still silky. A hand to her ass, narrowed her hips, flatter backside. Yet I could tell - fit, pretty, delectable.

"Are you going to ask me?" this unknown feminine wonder asked me.

"May I...may I suck your cock?" I asked softly.

"Yes, baby," came the soft, gentle reply. She guided it to me. Oh god, it was smaller. Narrower. Shorter. But I could fit it all in my mouth, all of it, and my nose was suddenly buried against warm flesh. Her hands gripped the back of my head, trapping and holding me. I had to yank back, hard, and released her with huge gasps. Then, the moment I was recovered, her hands, on my head, roughly pushing me onto her cock.

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