Sometimes it can lead to something much more.
“God that’s an incredible ass,” someone breathed behind me as I bent over to slide another label into the bottom shelf.
Knowing that the task was going to take me most of my shift at work, I’d worn my oldest and most comfortable pair of yoga pants for it. Having some creep objectify my backside hadn’t been in the plans when I had made that decision.
Standing back up while whipping my head around, my long hair covered my face and I angrily shoved it back behind my ear so I could see the offender. “What did you say?”
The man looked stricken as his mouth dropped open. It began moving rapidly but nothing was coming out. Finally, he blurted out, “I’m — I’m — I’m so sorry. I didn’t mean to say that out loud. I don’t why I did — I’m sorry.”
Looking duly chastised, he wandered farther down the aisle with me watching him in stunned silence. His apologies seemed sincere, and he was cute, even if he was twenty years older than me. My anger quickly dissipated.
“Wait,” I called after him. Still red in the face, he walked back a few steps toward me. Looking around the empty aisle, I still checked to see if anyone was listening. “Did you mean what you said? About my ass?”
With my self-esteem in the dumps after my breakup with my boyfriend three months prior, I had been feeling bad about myself of late. Even a misogynic comment by a complete stranger made me feel better, despite my initial anger. Plus, the guy did seem nice regardless of his very public faux pas.
He blushed a deeper shade of crimson. “I’m so sorry,” he told me again. “I didn’t mean to act like that. I don’t normally. I was thinking it and — and — well — it just came out.”
Looking him over, he wasn’t just older and cute but ruggedly built as well. In his forties with a beard tinged with gray, he was handsome while being youthfully hot at the same time. It had been so long since a man, not a boy, had paid me any attention, I was getting wet just having a conversation with him. The reaction was as unexpected as his compliment about my ass had been.
“I was a bit taken aback at first,” I admitted. “But — ” I looked up and down the aisle again. “Truthfully — I liked it. Thank you.”
He seemed to visibly relax at that point. “Again. I’m so sorry.”
“Don’t be.” I stuck my hand out. “I’m Carrie.”
“Jimmy,” he offered as his hand enveloped mine.
“Umm — Jimmy?” I started before faltering. It had been so long since I had propositioned a man, if I ever had, that I was searching for the right words. “Would you like to — I don’t know — maybe see that ass? Like as in — have me from behind?” His mouth dropped open again as I offered myself to him and prayed that he wouldn’t turn me down. “It’s just that it’s been a while for me — sexually — I had a rough break up with my ex-boyfriend several months back. And well — I don't usually do this — but will you have sex with me?”
“Yes,” Jimmy blurted out immediately. “Absolutely.” He calmed himself before asking, “When and where?”
“Now?” I offered as I bit my lip then added, “Before I change my mind.”
“Lead the way,” Jimmy told me, and I wanted to take his hand to lead him to the back of the store. Instead, I simply walked in front of him and put an extra sway in my hips just to give him an inkling of what he was about to get.
At the condom section, I stopped to pluck a three-pack off the shelf, but he stopped me by taking them from my hand. “Here,” he put them back and picked up a box of large size condoms. “This will be better.”
“Kinda full of yourself.” I winked at him.
“Not as full as you’ll be a minute,” Jimmy grinned, and I was suddenly glad he hadn’t reached for the extra-large. Something told me that unlike most of the college boys my own age I’d been with, Jimmy would turn out to be a large man.
Leading on, we headed for the manager’s office in the back. It was perfect, with me being the manager on duty for the day. In the office, I locked the door behind us then turned to my new impromptu lover. I wasted no time wrapping my arms around him to kiss him while at the same time hoping that no one would notice I was missing. Breaking the kiss, I turned my back to Jimmy and shoved my yoga pants down over my fleshy hips then bent over presenting my ass to him. He gave a low whistle of appreciation as he stepped behind me.
“Incredible,” he whispered as much to himself as to me as he gently ran his hands over my milky hips. His touch was making me wetter.
“Fuck me,” I told him over my shoulder and heard him fumbling with his pants, then felt him stroking his bare cock against my ass.
His velvety cockhead brushed my skin as he jerked himself off to get hard and it was only adding to what was becoming a flood between my legs. A second later, he was tearing open the box of condoms and I was making a mental note to pay for them when we were finished.
The box and a condom wrapper were deposited on the desk next to me and a few seconds later, I was filled by the largest cock I’d ever had in me. While not grossly huge, he was filling me incredibly nicely. I arched my back and gasped as I was stretched open.
“You’re big,” I moaned as he slid into me balls deep.
“I told you,” Jimmy said gently as he took my hips in his hands and began thrusting.
Laying my forehead on the desk as I was fucked, pleasure shot through my body, and I was moving with him as I pushed my ass back to meet him. “You feel so good,” I moaned as he picked up the pace.
He was sliding his long cock in and out of me, and I was soon panting into the desk as I reached across it to grab the opposite side for something to steady myself with. Behind me, Jimmy was slamming his cock into me as I struggled to keep from crying out.
“This is an even better view,” Jimmy told me as he fucked me over my boss’s desk. “Better than I could ever imagine.”
“Please don’t stop,” I begged remembering my ex's penchant for finishing way before I did most of the time.
With Jimmy being older and far more experienced, there was no chance of that happening. Rather, he snaked a hand around my hip to probe between my legs. Expertly finding my clit in my slick folds, he began tracing circles on it as his cock filled me.
“You’re not — ” I gasped as he fingered my clit, followed by, “I’m — coming.”
I climaxed instantly.
Pleasure exploded through me as I had the biggest orgasm of my life with Jimmy’s fingers working on my clit and his large cock drilling deep into me. As I exploded in ecstasy, I couldn’t keep quiet and cried out as I came despite all attempts not to. As my orgasm subsided, I became worried that someone had heard us.
“You gotta come — please!” I begged him.
Jimmy’s grip on my ass tightened as he dug his fingers into the excess on my hips. His impressive cock began pulsing inside me and for the first time, I wished that he wasn’t wearing a condom so I could feel every wonderful inch of him. A second later, he groaned behind me as he filled the condom before slumping over top of me. My legs were weak, and I crashed under our weight onto the desk until the edge of it bit into my hips. Seconds later, Jimmy pushed himself up off me then stepped back. As he did, his incredible cock pulled from me, and I moaned at its absence.
Finally, I stood back up on wobbly legs and turned to face him as I reached for my pants. Jimmy's eyes locked on the plump shaved crease between my legs, and I followed his gaze to see it coated with my cum and condom lube. Reluctantly, I pulled my panties and yoga pants back up and settled them into place as I eyed Jimmy’s beautiful cock for the first time.
Encased in the soiled condom and starting to soften, he was far bigger than any boy I’d ever been with. The first real man to fuck me, I couldn’t help but gawk at the size of his softening erection and remember the full feeling that it had given me. He pealed the condom off carefully, then wrapped it in a tissue to throw in the trash to hide the evidence.
“So, where do we go from here?” Jimmy asked me as he tucked his spent cock away.
“Would you’d like to get some dinner? We kind of did this whole dating thing backward,” I replied.
“I’d like that.” He smiled at me. Despite having just been fucked by him, asking Jimmy out had still made me nervous. “When does your shift end?” he asked.
“Seven.”
“I’ll pick you up here at seven then.”
It was my turn to blush as I made a date with an older man that had just fucked me. Feeling increasingly better about life and myself than I had in months, I tucked the strands of my hair that had come loose behind my ears and smiled up at him.
“You really do have a great smile to go along with that incredible ass,” Jimmy told me, and I began to like him more and more. He certainly was a charmer.
“See you at seven then,” I beamed at him. I knew it was the beginning of something good.