Back when I was 18, I worked as a bagger at a local grocery store. I'd pack up the customer's order in paper or plastic bags, then wheel it out to their car to put it in their trunk. One time, there was this older woman, probably in her mid-forties. She had long, wavy brown hair, a beautiful face, a plump ass, and tits nearly the size of my head. Considering she was wearing a blouse with a deep v neckline, I was understandably distracted as I put her groceries in bags. She caught me staring a few times, which seemed to amuse her. As I pushed the cart out into the parking lot, she started chatting with me.

"Hey there handsome, how old are you?"

I blushed and replied, "18, ma'am."

She stroked my hair and said, "Finally old enough to make and receive requests, huh? I bet the girls are all over you at school."

I shrugged and looked down. "Not really. They mostly pester the guys on the sports teams."

The woman clicked her tongue and shook her head. "Don't worry about it, they'll come around. Oh, here's my car, lemme pop the trunk."

She pressed a button on her key fob and lifted the trunk lid. As I started moving the bags in, she started rubbing my back. It felt rather nice, and comforting in an almost maternal way. She asked, "But you have had sex before, right?"

I blushed and nodded. "With one of the volunteers that came to health class."

The woman frowned. "And no one else?"

I slowed down as I put the last of the bags in, embarrassed at what I was about to admit. "I just... don't want to impose on anyone who isn't attracted to me."

She cooed, "Oh honey, you sweet, sweet child."

I would have been even more embarrassed if she didn't wrap her arms around me and push my face into her bountiful boobs. She smelled sweet and faintly floral, and felt soft and warm around my head. I hesitantly hugged her back, a little awkwardly since I was partially hunched over. She stroked my head and said, "Honey, I want you to play with my body and fuck me. Can you do that for me?"

I looked up at her in wonder. "Are you sure?"

She smiled at me and said, "Check how wet I am for you, babe."

I hesitantly slid my hand under her skirt and pushed her panties to the side. She shivered and bit her lip as my fingers brushed across her slit, coming away wet with her juices. I looked at her with wide eyes. "Woah, you are wet!"

She giggled and pecked my lips. "You bet I am. Now, take your time and play with me however you like. I may be the one making the request, but I really want you to enjoy yourself."

I straightened up and hesitantly cupped her face in my hands. She winked at me with a smile. I couldn't resist any longer, and pulled her into a kiss. My tongue slipped into her mouth without resistance, meeting and twining with her own. She hummed happily, her hands roaming across my chest. Taking it as a suggestion, I caressed her breast through the fabric of her blouse, marveling at how soft and warm it was. She broke the kiss and said, "Go ahead and squeeze them, honey. You can get a little rough, I won't mind."

I was already hard before, but that sent a surge of arousal through my body. I couldn't help but grin as I lifted and squeezed her tits, coaxing them out of her bra and top. She giggled when they spilled into the open and I stared at her hardened nipples. I didn't need any prompting to flick my thumb across it. When I pinched the nub lightly, she squirmed and rubbed her thighs together. "How do you like my tits, handsome?"

I kissed her lips for a brief moment and beamed at her. "They're amazing!"

She smiled and said, "I'm glad you like them, I-"

At that point, I lifted one of her boobs and started sucking on her nipple. She moaned, running her fingers through my hair. I couldn't believe the sounds I was coaxing out of her. The volunteer in health class was one of the chubby lunch ladies, who mostly spread her legs and ignored me to chat with the volunteer next to her.

I felt adventurous, and while I was sucking on the cougar's tit, I unzipped and pulled down her skirt. My fingers dug into the plush flesh of her ass, squeezing and kneading. She cooed happily at that and stroked the bulge in my pants. A jolt of pleasure shocked my system, and there was one thing I absolutely had to do. I turned her around and she braced her arms against the car trunk. She had an eager, hungry look in her eyes as I pulled down her silky lavender panties. Her crotch was absolutely soaked and glistening in the afternoon sunlight. I quickly pulled down my pants and boxers and stepped closer. She shook her ass at me, just enough to make it difficult to line up my cock with her slit. I growled and slapped it without even thinking. She let out a sweet cry of surprise and pleasure.

I held her hip with one hand, and pushed my glans into her blushing pussy. She hung her head and panted, "Oh, fuck. Keep going, fill me with your cock!"

I was happy to comply, plowing my length into her feverishly warm, silky wet depths. She whimpered and ground her ass against my thighs as I hilted inside her. Experimentally, I spanked her ass again. She moaned and clenched around me, making it feel like my dick would melt inside her. I thrust in and out with short, sharp strokes. I had to pause every couple of thrusts, coming dangerously close to ending the fun each time. While I waited for the tide of my arousal to recede, I reached around and grabbed her dangling titties. They felt so heavy, so soft, so right in my hands. Her breath hitched when I gave one a particularly hard squeeze. I asked, "Did that hurt?"

She shook her head and clenched her pussy around my dick. "Like I said, you can be rough with them."

Experimentally, I crushed her breast in my grip, drawing a moan out of her. Then I tried slapping her other tit. She cried out, "Oh fuck yes!"

I slowly worked my cock in and out of her writhing honeypot as I alternated slapping her tits and ass. She flung her head back and groaned, "I'm so close! I'm going to fucking cum on your cock!"

I kept up the abuse, turning her ass a glowing pink. A few strokes later, her pussy flooded with her honey, milking my cock desperately. I didn't last a second longer, my vision going white as pleasure overtook me. Rope after rope of semen fired from my cock, pooling deep inside her. It felt like I was cumming for over a minute, just desperately pumping more and more spunk into the sexy older woman.

After we caught our breath, I slowly pulled out of her. A small torrent of our mingled cum spilled out and ran down her inner thigh. She stood up and turned to face me, glowing with post-coital bliss. She cupped my face and kissed me deeply, her tongue plundering my mouth for several long moments. Finally, she pulled back and gazed at me in adoration, her huge chest heaving. "That was amazing, I think you might have a talent for this."

I grinned at her, impulsively grabbing her tit. "Really?"

She nodded and bit her lip, looking me up and down. She knelt in front of me and sucked my softening cock into her mouth, slurping up her juices from it. I shivered in pleasure, just starting to feel overstimulated. She mercifully let it fall from her mouth, then turned to grab a pen out of her purse and write something on her receipt. She handed it to me and said, "Call me if you ever want to make a request, I'll be over as soon as I can."

I blinked as I stared at the phone number, then at her. I pulled her in for one last kiss, tasting our mingled cum in her mouth. I broke the kiss after a handful of seconds and grinned at her. "I usually masturbate before going to sleep, but I think I'll call you instead."

She chuckled as she bent to pick up her skirt and panties. "I'll be looking forward to it."

We said our goodbyes, and I spent the rest of the shift in a state of deep contentment, tinged with anticipation for the evening. I had a feeling I wouldn't get much sleep tonight.