I had just walked in from settling a dispute between two high-school-age bagger gathering shopping carts outside when she flashed me her million-dollar smile.
“Hello, Jack.”
I was one of the front end supervisors at a local grocery store while I was in college and she was one of my cashiers. It was the summer between her sophomore and junior years at college and I was about to start my fifth year to complete a double major. The two of us hit it off well. Ashleigh was a beautiful woman and we had bonded nicely as supervisor and cashier. She was a quick learner and did her job well. But she was definitely a distraction.
The two of us exchanged innocent flirts back and forth. Ashleigh knew she was a beautiful woman as she knew just how to flaunt her 34B breasts and very well proportioned ass for her athletic five-foot-seven stature to the customers – and to me. Her blonde hair, when down, went just below her shoulders. She was the type of girl that every man has dreamed about.
She had started in late May and by mid-June, it became a guessing game for me – is it her ass or breasts she is going to lure me in to stare at today? It even had reached a point where we, mainly Ashleigh, were finding ways to “accidentally” touch each other’s hand or arm in conversation. I could tell when she would play dumb to get me to come over to her register to “help” her.
There were even a couple of times where she timed her movements just right where her ass or breasts crashed into my body. She always acted so apologetically for being in the way and not that an inappropriate touch between a supervisor and his employee had just occurred. Of course, twenty-three-year-old me didn’t mind at all. She was very sexy.
At the time I thought she had a boyfriend. I never had directly asked her if she did or not because the way she spoke hinted that she had one and that was the way my mind was set. And that brings us back to, “Hello Jack.”
“Hey there, Ashleigh,” I replied.
“Is it about my break time? Trisha is back you know.”
“Yeah, sorry. Was dealing with Kyle and Blake outside. You may go on your break.”
Ashleigh puffed out her chest a bit and bounced in the air as she said, “Thanks, Jack!”
I slyly watched her walk away as long as I could without drawing suspicion. I thought to myself that her boyfriend had better know he is one lucky guy to be dating a woman like her.
Strolling back to the main aisle way to watch over the front end, Carla, who was the customer service desk attendant and basically my supervisor, called me over to her.
“Jack, you need to go take a break or something,” she said. “You’ve been here over five hours and haven’t taken a break. Go now!”
I reluctantly agreed, clocked out and headed for the breakroom.
I entered the empty breakroom and sat at a round table to watch television. Moments later the door opened and Ashleigh swiftly walked in and sat in the chair next to me. Not saying a word, she placed her hand on my crotch.
“Is this what a girl has to do to get your attention, Jack?”
I was stunned. Disbelief even. I couldn’t compile any words to even form a gibberish sentence. Then Ashleigh did the unthinkable – she unzipped my pants and stuck her hand inside. I was already forming an erection from her hand on my crotch and now she had her hand inside my pants and grasping my cock.
“Mmmmm, someone’s happy to see me,” Ashleigh said with a delightful smile across her tanned face.
I finally pulled myself together enough to say maybe the most obvious sentence I could have said.
“Of course. You are sexy… very sexy Ashleigh.”
With her free hand, she reached across into my pocket and pulled out my phone. We had interacted so much in the past month that she had seen me open my phone hundreds of times and knew my password without asking. She sent herself a text message and inserted my phone back into my pocket. With her hand still in my pants, holding my now rock hard cock, she took out her phone and sent me a message back.
“We are both off at 10 p.m., right? I just sent you my address. Meet me at my house after work and we can both get what we have been desiring.”
She put her phone away, withdrew her hand from my pants, and zipped me back up. As she stood up to leave the break room, she leaned down and kissed my cheek.
“See you back out on the floor, boss,” she said winking as she exited the room.
The next two and a half hours were difficult, but I managed. It’s never easy supervising the front end on a Saturday so maybe for the best, Ashleigh wasn’t on my mind the entire time. But she did cross it a number of times.
Ten o’clock soon arrived and business had died down enough for Ashleigh to clock out right at 10 p.m. She said goodbye to everyone while looking at me and headed for her car. I clocked out a few minutes later after wrapping up a few things. She had parked right next to me in the lot and was waiting by my driver's side door.
I walked up to her and gently leaned in for a kiss and my hands found her ass to squeeze her cheeks. She squirmed and moaned before breaking the kiss.
“Not here. My place. Don’t rush,” she said. “I’ll still be horny if I beat you there.” She winked once more, entered her car and drove off as I gave chase.
I arrived at her place, a townhouse, and exited my car quick enough to see her running inside. I ran to the door which was left open. I hadn’t entered the house ten seconds before she pounced on me and our lips locked. I pinned her against the door and locked it. Then she pinned me against the adjacent wall – our lips never uncoupling. As we made out, our hands roamed the other's body. My hands drifted under her shirt to feel her soft, smooth skin then down over her pants to grope her ass.
She started to lead me to the bedroom as we gasped for air. We approached the bed and I playfully pushed her on her bed at which point I started taking off her pants. She wore pink lace cheeky panties. I kissed her pussy through the wet fabric before slowly removing them from her body. At the same time, she flung her shirt off to reveal a matching pink lace bra that had just a bit of support.
My tongue started to dance around her clit but my eyes darted between her shaved pussy and lace-covered breasts. Both were the most beautiful I had ever had. I soon focused my concentration on her soaking wet pussy, giving it my full attention. As I gave her a fifth long lick with my tongue, her hands grabbed me by my hair and moaned loudly. Her hips began to squirm and my one of my hands drifted up to cup her breasts. I massaged her left then her right breast as I ate her pussy.
“Jack, I need your cock inside my pussy,” Ashleigh said in between moans.
I was slightly disappointed because I love making women cum with my mouth. But I stood up and took off my shirt. Ashleigh lifted herself up by her elbows as I ripped my pants and boxer briefs down simultaneously.
“Woah,” she said somewhat shocked with a big grin on her face.
“What?” I asked worriedly.
She started to slide off the bed and onto her knees as she said, “I didn’t know you were this big, Jack.”
I was at full mast, harder than I had ever been. Her right hand grasped my shaft as her left cupped my shaved balls. She then licked my cock head slowly and seductively.
“Ohhhh, Ashleigh…” I responded as her tongue repeatedly licked my cock.
She giggled before using her mouth to engulf my cock. A few plunges later and she had me in my entirety in her mouth.
“Mmmmmmm,” she said as she removed my cock from her mouth. She looked up from my shaft to my eyes and said, “I’ve never had one this big before.”
She licked her lips and stroked me. It was wonderful and she stopped right as she realized I was about to cum.
“Not yet, big boy.” She stood up and we kissed. My hands cupped her ass again, making her squirm once more. She pulled me back towards the bed, still with my cock in her hand and she laid down on the edge. She lined me up with her entrance and when our eyes met as she looked back up, I pushed in slowly.
Her eyes closed and her head fell backwards, and my head fell, too. The sensation of my cock piercing her pussy was like none I had ever experienced before with another woman. She was very wet, and her pussy clamped down around my cock. My pumps inside her were slow as I wanted to savor each new inch I explored.
The tension I didn’t know that had built up between Ashleigh and myself were being released as told by our nearly synced up moans. Then I felt more pressure around my cock it became harder to penetrate this depth of her pussy.
“Ohhhhhhhhh, Jack!” Ashleigh moaned loudly as she sat up. “Andy hasn’t ever touched there…” her voice seductively trailed off.
That confirmed my longstanding theory that she did have a boyfriend and unfortunately for him, Ashleigh wasn’t lying when she said she hadn’t had a cock as big as mine before. I quickly looked down to size up the situation. I was roughly five and a half inches inside her with another inch a half to go. With my cock still inside, I lean down to kiss Ashleigh. She reciprocated with a long slow kiss. Before I restarted my efforts to bury my full cock inside her, I gave each of her breasts a kiss.
As I wrapped up kissing her left breast, I slowly pushed my cock further into her pussy. Her moans filled the townhouse as I reached depths of her pussy no man had been before. I was gentle with my thrusts. Not only did I want to remember the feeling myself but I also wanted to remember the expressions on her face. She bit her lips, closed her eyes, squeezed her bra covered breasts, moaned with her head constantly moving until I had my entire cock inside her.
“I feel so full, Jack. Oh my God,” she said looking down at me completely buried inside her. “Now please, Jack – fuck me.”
There was no need for me to say a word. I simply moved my hands to her hips, held her firm, and began to thrust my hips in and out. The volume of her moans increased with my pace. I felt her pussy squeezing my cock with each push inward.
I then moved my hands, while I continued to thrust into her pussy, to her knees and lifted her legs into the air and onto my shoulders. I held each leg as I threw my weight into her with each push into her depths.
“You fuck me so good, so deep,” Ashleigh said between moans.
“You squeeze my cock just right,” I said, “I can’t believe I didn’t make a move sooner and first.”
She tried to moan seductively but I thrust forward, and it came off as just a normal moan of enjoyment.
I then spread her legs wide fucked her in a modified spread eagle, but it didn’t last long.
“I want to be on top now, Jack,” she said with authority.
I withdrew fully from her pussy for the first time in what seemed like hours. I bent down quickly and gave her pussy a quick but long lick and I kissed her clit.
“Ohhhh, Jack, mmmmmm, you know exactly what to do,” Ashleigh said with definite delight in her voice. “Now lie down here. It’s my turn to fuck you now.”
I did as I was told. I lay down admiring her body once more as she sat on her knees on the bed waiting for more of me. Her eyes darted between my eyes and my cock which was covered in her juices.
Ashleigh climbed on top of me, straddling me right above my hard cock, which rocked back and forth with the beat of my heart. She then, finally, removed her bra to expose her bare 34B breasts to me. They were beautiful, just like her, and were perfect for her body type. The bra had a little support but otherwise, she had firm, round, youthful breasts.
My hands instantly moved up to cup them. I felt both all over. I then felt her take ahold of my cock as she lowered her body. She guided her pussy to engulf my cock. Never stopping, never slowing, she had my cock encased in one push downward.
“Ohhhh, yes, Ashleigh,” I said in response.
“You fill me up, Jack,” and she began to bounce up and down.
Every downward push she took herself down to the hilt. My hands eventually faded down to rest on her thighs as she fucked me.
Her hands, which had been bracing herself on my chest, then moved up to her head. She held herself down on my cock, wiggling back and worth with small pumps mixed in. I sensed she was close to cumming as was I. I repositioned myself off the pillow, lifted her up slightly with my hips, and began to thrust upwards. She attempted to match my rhythm but simply held herself there.
“I’m cumming Jack!” she said.
I thrust harder as I felt her orgasm race across her body, through her pussy, and around my cock. I gave one more thrust up into her depths and came deep in her pussy. She collapsed onto my chest as my hips sank back down with my cock still buried in her, spurting cum.
Still catching her breath, Ashleigh said, “Why did we wait a month to do this?”
“I thought you had a boyfriend,” I said with a chuckle.
“I do, but now,” she paused impressively, “I have work lover.”
I responded to her with a kiss. It wasn’t until she realized I was still hard and in her pussy that she broke the kiss. She lifted herself off my cock, scooted down my body, and took ahold of me with her hand. Her ass was raised in the air as her tongue worked over my cum covered cock.
Once she had cleaned my cock, she inched it into her mouth. Soon, she had every inch of me inside her. Working me between her lips slow then fast, then slow again, she worked my cock like her life depended on it. Soon my moans and grunts of lust turned into the signal that I was about to cum. She rapidly moved me between her lips, teasing my head.
“Ohhhh Ashleigh….” was all I was able to say before I blew a second load, this time in her mouth. When the spurts subsided, she looked up smiling at me, and swallowed all of my load.
She migrated back up towards me and I wrapped my arms around her. We lay there naked for another hour before I saw the clock read 1:30 a.m.
I kissed her forehead before gently removing her from my body.
“Going home so soon, Jack?” She said with a fake pout.
“Tonight, I have to. The next time though I can spend the night,” I said.
“I’m so glad you want to have a next time, Jack. I... I really enjoyed this," she said pulling a blanket across her body with her blonde hair masking part of her face. "See you at work tomorrow,” she said seductively and winking.
“See you at work tomorrow, Ashleigh."
