I was sitting at the hotel bar, still waiting. I already knew, deep down, that I had been stood up. I knew why, too. I had been seeing this guy Mark for a few weeks, and he had clearly been hoping to get in bed already, but I’ve always been kind of shy about that sort of thing. I guess my conservative parents still held some sort of moral power over me, despite me moving across the country to get away from their tepid ways.
My dating life had been miserable for months. I had been called a tease, ghosted, and stood up several times. It was just something about being so… vulnerable, something shameful, about taking that last step into the bedroom with some guy I barely knew.
I was looking at myself in the large mirror behind the bar when someone tapped my shoulder. My heart raced as I turned around, but it wasn’t Mark. It was an older gentleman, perhaps in his late fifties or early sixties. He was tall and had greying hair and a closely trimmed beard, almost a little handsome in a rugged way.
“Hi, are you Sandra?” He asked, looking around almost nervously.
I wasn’t Sandra.
“Yes,” I said, before my mind could stop my mouth. I think back on that moment now, the moment that changed everything, and still can’t figure out why I said that. It was just… loneliness? I don’t know.
Anyway, the man smiled at me and patted my arm in a strange, proprietory way.
“Oh, you are even more gorgeous than I had hoped.” He sat down next to me, ordering a new drink for me and a beer for himself while I sat, stunned into silence by my own lie.
This man clearly thought I was his blind date. And I don’t know who had set his real date up because he must have been more than twice my age, as old or older than my father.
He sipped his beer with a slightly shaking hand.
“I don’t usually do this sort of thing, you know. I haven’t… met anyone since my wife passed, almost ten years ago. I’m a bit nervous.”
His voice was pleasant, deep and gravelly. Was I attracted to him? I don’t know, but something in me felt an urge to see where this went. Maybe it was pity. Maybe it was just my own loneliness. I put my hand on his arm, stroking the sleeve of his shirt.
“It’s okay to be nervous. I’m always nervous before meeting someone new, you never know how things will go.”
I smiled at him, sipping my drink as he nodded.
“I guess you’re right,” he said after another draught of his beer. He looked at me, taking in my body in a way I thought both rather inappropriate and strangely… erotic. I felt my cheeks burn a little, and he chuckled.
“Oh my, that’s a pretty blush. You are truly breathtaking. I was hesitant about this, but now I’m glad I came.”
We started chatting a bit, about general things. He seemed to avoid personal questions, and I obliged.
I thought seemed rather forward for a first date, especially for someone who hadn’t dated for years. Or maybe, I pondered, that was why he was a little… rusty.
After about ten minutes, he touched my arm again.
“Well, thank you for making me more at ease. You really are a pleasure. He winked and downed the last of his beer. “Shall we go upstairs?” He asked, and stood up. I was dumbfounded for a second before I remembered the rooftop restaurant of the hotel. It was a really fancy place, too fancy for me but this man seemed rather well off. I suddenly realized I didn’t even know his name, but now it seemed awkward to ask.
“Let’s,” I said, not really knowing what to do. My brain was not working properly, I felt. Why had I started this charade? It felt too late to back out now, and to be honest, I was starting to enjoy his company.
We walked in silence to the elevators. He seemed to be getting nervous again, so I put a hand on his arm. He placed his much bigger hand over mine, which sent a strange tingle down my spine. Here I was, on a blind date with a man more than twice my age. We rode the elevator in silence, as I couldn’t think of anything to say. Suddenly the elevator stopped, after what felt like too little time. I looked at the little floor indicator. We were just halfway up, but the man started leading me out into the corridor.
My heart and mind began racing. Was he taking me to a room? My brain felt like it was moving too slow and too fast at once. How had I ended up here? I was about to say something, anything, but I couldn’t get my mouth to open. Just as I was about to yank my arm away, he stopped in front of a door.
“Well, here we are.” He said, and I froze. He opened the door and ushered me inside. I meekly went along, like a sheep herded by a dog. My heart was pumping so fast now, and my mind was racing. I was alone with a strange man in a hotel room. A very nice one, I might add. There was a large double bed, a little salon with cozy furniture and a huge bathroom.
I just stood there, feeling trapped and strangely elated. Where was my little lie taking me?
He stepped over to a small dressing table, taking out an envelope from a drawer. “Brian said you would want pay in advance,” he said as he stepped over to me, handing me the thick envelope. I just stood there holding it for a second, my mind blank.
He thought I was a whore.
The realization struck me like a thunderbolt. Of course he had been nervous. He was not on a date, he was purchasing someone. Me. I looked at the envelope, dumbstruck. “It’s all there, but you’re welcome to count it!” He assured me, smiling nervously.
I opened the envelope. There was a thick wad of bills there. I didn’t know how much, but it looked like… a lot.
I just swallowed. And then I put the envelope in my purse.
I couldn’t think straight. I, the prude stuck up who got stood up for refusing to sleep with someone I actually dated, was now in a room with an old man who wanted to purchase my body.
Who had purchased my body, I realized, as he smiled more assuredly and took a step closer. He looked me up and down.
Go. Run. Leave. Give the money back. Say it was all a mistake.
All this went out of my mind as he bent down and kissed me, hungrily. His beard was softer than it looked, but it still scratched my jaw. I kissed him back out of instinct. Then out of some strange, shameful desire which sent both a pang of guilt and a wave of arousal.
His large hands started to caress my body through the little black dress I wore. He grabbed my ass so suddenly and firmly that I yelped a bit into his mouth, which made him chuckle and pull back.
He seemed more confident now, and I could feel his erection growing between us as he pressed his body into mine.
He took a step back, looked at me and then went and sat down on the bed.
“Could you undress for me, please?” He said, staring at me hungrily.
I swallowed. And again. And then I took a step forward, my heart beating faster than I ever remember it doing, and pulled my dress straps down from my shoulders.
The dress was tight and had no zipper, so I had to wiggle a bit to make it come down my body, all the while being consumed by his hungry eyes.
In spite of my non-intentions of sex, I had worn rather nice underwear. My lacey black bra felt smooth as I traced my fingers along it, and then, with shame in my heart and desire growing between my legs, I unhooked it. I let it fall to the floor, letting my heavy breasts bounce a bit. The room was a bit cold, and my sensitive nipples were already stiffening. Perhaps from more than just the cold, I shamefully admitted to myself.
The man’s eyes were firmly locked onto my breast, and the desire in his gaze was burning now. It made me even more aroused, in a strange way, and an odd confidence started to bloom inside me.
My fingers found the lining of my panties, started tugging ever so slowly, then stopped.
My heart was pounding now. I was really doing this. Well, in for a penny… some part of me whispered.
“I’ll show you mine if you show me yours,” I said, surprising myself with both my own words and the huskiness of my voice.
He grinned, hunger in his eyes. Quickly, eagerly, he unbuckled his belt, undid his suit pants and took his cock out.
My eyes widened. I wasn’t a virgin, but not very far from it either, with only one serious relationship after college that only lasted a couple of months.
This man was far, far bigger than anyone I had been with. It was uncut, veiny and almost a bit wrinkled, with grey pubes surrounding it. The size, especially the girth, scared me a little, but it also stirred something deep in me. I felt a warm, wet stirring between my legs as my moist cunt started to swell in anticipation.
I slowly removed my underwear, letting him see the little trimmed bush and the wet slit that now hungered almost as much as he seemed to do.
My mind was far from clear now, arousal sending every notion of shame away as I without a second thought knelt before the bed. I couldn’t have stopped myself from taking his throbbing cock in my mouth if I wanted to, and to be honest I didn’t.
There was salty precum glistening on his foreskin already, and the salty taste sent a shudder through my body as my warm tongue lapped it up. With a groan he grabbed my hair firmly in his fist and I eagerly took more of him inside. I had never dealt with an uncut cock before and at first it was vexing me, but I managed to move the foreskin back with my lips so my eager tongue could play with the head. He pushed my head down, just slightly, and I started to bob up and down. I couldn’t take it very far in, as it was too wide, but his grunts made him seem like he enjoyed it.
I was enjoying it as well, I realized, as I felt a slow droplet of my own juices run down my inner thigh. I was losing myself in the arousing wrongness of the situation as my tongue played along the shaft of his veiny cock, and suddenly I had a hairy, big ball in my mouth. He moaned deeply as I sucked on it, his grip on my hair lessening. Instead his heavy hand started petting my head, which oddly enough set an even deeper fire burning in my wet, swollen cunt.
I went back to the cock, slurping loudly as I started to work the swollen head, his cock throbbing on my tongue. Suddenly he pulled my head back, and shame returned as I audibly whimpered in disappointment. He didn’t seem to hear, too caught up in his own lust. He bent down and picked me up like I was nothing, almost throwing me on the bed. He ripped of his shirt and took out a condom out of his pocket. Honestly, I don’t think I would have even thought of that, so deep was my arousal.
In one motion he rolled the condom on his cock, flipped me over to my stomach and positioned himself over me. I moaned in arousal as he put a thick finger inside without warning, finding my sweet spot in an instant. I was so wet now that his finger almost made a splashing noise as he worked me up, my ass grinding up towards him in eagerness.
I couldn’t think, couldn’t do anything but focus on the moment as he shifted and slowly started pushing his fat cock inside me.
We both grunted like animals as he entered me, filling me completely. My whole body was awash in pleasure as he started pumping, slow at first but building up speed, building up pleasure, building up glory, I started to cramp up, the walls of my pussy tightening around his veiny member, him leaning forward to lick my ear, his warm breath on my skin, and suddenly, release.
I came harder than I ever had before, wave after wave of pleasure rushing from my clit, up my spine and out through my whole body. He grunted, too, pulling out while I was still in bliss, and flipped me over again. Ripping off the condom he crawled up the bed som his cock was in my face, and I obliged by taking the almost pulsating head in my mouth, licking eagerly while he stroked his cock in a frenzy. After just seconds, he exploded in me, his throbbing bucking in my mouth as waves of salty, wet cum filled my throat. He groaned deeply and held his cock there for a few seconds, and I swallowed it all down like a hungry bitch.
We lay there panting afterwards for a while, his softening cock inches from my face before I silently got up, quickly dressed and left the room, my hair in a mess and the flavour of his cum in my mouth.
And that was only the beginning.
Source: reddit.com/r/eroticliterature/comments/uvbuja/taking_my_first_steps_in_sandras_shoes_fm_female