That Dirty Old Rascal

My favourite customer and my first older man.

Hey y’all, I’m Megan. I’m 26 now, 5’6” with long chestnut-brown hair that falls past my shoulders, bright blue eyes, curvy as ever, and yeah, I have big ol’ 34F boobies that pretty much announced themselves way too soon.

I was always a curvy girl, but at 14 my boobs exploded. By 15 I was already a D-cup and getting stares everywhere I went. I was pushing an E-cup at 17, and reached 36F at 18. It was futile trying to hide them at that point.

I still wore baggy hoodies, but they just made me look ridiculous. Boys were dumb about it, girls were either jealous or mean, and grown men… well, they weren’t subtle at all. I felt embarrassed and awkward for a long time, constantly crossing my arms.

Then suddenly I was like, ‘Okay, this is my body. I have really big tits for my frame and age, get over it, Megan.” I started standing up straighter, wearing clothes that actually fit me… even if they showed a lot of cleavage, and I learned how to do sexy makeup.

That’s when I discovered I could turn heads on purpose, instead of just by accident. My first real intimate experiences were a bit later than most girls, because I was so self-conscious about my chest. I lost my virginity at 18 to my high school boyfriend, Brad.

He was sweet, but clearly obsessed with my boobs from day one. The first time we were alone in his room, and I took my shirt off, his eyes went wild.

“Holy shit, Meg!” he reacted.

I remember blushing so hard while feeling this weird rush of power. He wasn’t gentle either, and spent more time there than anywhere else. It felt good, but I left that night accepting my big boobs were all boys cared about.

After we broke up, I had a short fling with a slightly older guy named Mikey. He was far more experienced and actually knew what he was doing. That’s when I started learning that my breasts could be a huge source of pleasure for me too, not just for guys.

Mikey loved playing with them, sucking, squeezing… and I discovered I was really sensitive. Sometimes just the right touch would make my whole body light up on fire. I started getting more confident in bed because of that.

When I turned 19 and moved to the city for college, I started embracing my body even more. I got my first proper bra fitting, and realized I didn’t have to be ashamed of how big they were. That confidence carried into the bedroom.

My first one-night stand was with a guy I met at a party. I wore a tight little top that showed serious cleavage, and I remember the look on his face when I took it off. Instead of feeling shy, I felt sexy. I took the lead a little more that night too. and it was super, super hot.

Having gone from the shy girl hiding in hoodies, to the girl who loved guys staring at my big, juicy tits, admiring their weight, their softness, how they stretched and filled my tops, I successfully applied for a waitressing job at Hooters. I was so damn excited.

I worked there for a whole year, starting when I’d just turned 20, and one of my favorite regulars was Max, a much older guy in his early 50s. He was always well-dressed, polite, and came in by himself every couple of weeks when he worked on the road.

Never loud, never creepy like some guys could be. He always sat in my section, ordered the same food and beer, and he tipped really well. He was a nice guy, divorced, successful in business, enjoying the inviting view.

One slow Tuesday night, after I’d been serving him for almost a year, and my time at Hooters was coming to an end, Max waited until after his meal, and when the restaurant was pretty empty, before talking to me very discreetly.

“Megan, I’ve been coming here a long time because you make an old man feel young again. You’re beautiful, sweet, and you’ve got the kindest smile in the whole place. I’d like to offer you something. If you’d be willing to spend the night with me… just you and me, no pressure, nice hotel. I’ll give you a thousand dollars. Cash. No one has to know,” he said, his tone respectful.

I froze for a second, holding his check. A grand was a lot of money for a Hooters girl. I looked at him… really looked. Max wasn’t sleazy about it. He was sincere, a little nervous even, and he made it clear it was completely my choice. No hard feelings if I said no.

My heart pounded as he glanced at my prominent mound in the orange tight shorts, before his gaze lingered on my big boobs straining against the white tank top. But the way he’d always been respectful, the stack of bills he’d already tipped me over the months… and yeah, part of me was so curious.

Max was older, experienced, and clearly knew how to treat a woman. I bit my lip, glanced around to make sure no one was listening, and then I smiled at him. “I’ll do it,” I whispered.

He looked surprised, then genuinely happy. “Tonight? After your shift. I’d love it if you came back to my hotel with me exactly as you are, Megan.”

“I can’t do that,” I giggled. “Company policy. I have to change before I leave, but I can change back into it once we’re in your hotel room,” I giggled again.

“I like the sound of that,” Max chuckled.

After my shift, I changed into my jeans, t-shirt, and a hoodie, then met Max on the corner outside the restaurant. He smiled and nodded, promising me he would be respectful and gentlemanly. I told him I trusted him, then we walked casually to his hotel a block away.

Once we were inside his hotel room, Max lived up to his promise. He poured me a glass of wine, told me how beautiful I was, and how he’d been thinking about this for months. I thanked him before going into the bathroom to change once again.

He was sat on the edge of the big bed when I’d returned, still fully dressed in his shirt and slacks, grinning at me from head to toe, then fixing his gaze on my breasts as I stood in my Hooters uniform, my hair falling down my back.

“Megan darlin’… stay right there and let me look at you… without worrying people will catch me admiring such a beautiful young woman,” he said softly, his voice low and controlled.

I stood still but relaxed in the middle of the room, arms by my sides, chest pushed forwards slightly, as Max stood up slowly and walked around me, his hands gently brushing my waist, my hips, my ass. He was clearly in awe, murmuring how perfect I looked in the uniform, how incredible my tits were.

He then stepped back, eyes dark with lust. “Now… take the top off for me, sweetheart. Slowly… very slowly.”

Heart racing with nervous excitement, I hooked my fingers under the hem of the tight tank top and peeled it up over my stomach, then over my heavy, bulging breasts. They spilled out with a soft bounce as I pulled the shirt over my head and let it drop to the floor.

Max’s eyes went wide. “Jesus Christ, Megan…” he gasped. “You got a rack and a half on you, sweetheart.”

He stepped closer and reached out tentatively, like he was afraid they might disappear. His hands were warm and surprisingly gentle. He cupped them from underneath, lifting their heavy weight, feeling how full and soft they were as his thumbs brushed over my rock-hard nipples.

Aroused, I reached down and unzipped his pants, pulling out his old, thick, veiny cock. Something about him was already rock hard too. While he explored my tits, squeezing and kneading them with utter confidence, I started stroking him slowly with my hand, long smooth strokes, twisting a little at the head, making him quiver.

“God, Megan… he groaned deeply, eyes half-closed, completely lost in my breasts.

He lifted them, pressed them together, watched them overflow his hands, then leaned in and kissed the tops, then the undersides, then sucked one erect nipple into his mouth while his other hand continued groping the other breast. I kept working his cock with my hand, feeling him throbbing.

After a while he pulled back, breathing heavily, and grabbed a bottle of massage oil from the nightstand. “I need to see them shiny,” he said, voice thick. He poured a generous amount right onto my chest and started rubbing it in with both hands, slow, deliberate circles, making my big tits glisten under the light. The oil made them look even bigger and heavier as they slid and jiggled in his palms.

“On your knees, sweetheart,” he instructed kindly, sitting back on the edge of the bed, pants bow around his ankles, his thick cock standing straight up, shiny with clear, yummy liquid.

I dropped to my knees between his legs, pressed my slick, oily breasts together around his cock, and started giving him a long, slow tit-fuck. Max moaned loudly, leaning back on his hands, watching every second as his cock disappeared between my huge, glistening tits. I moved up and down, squeezing them tight around him, letting the head pop out at the top with every stroke so I could lick it.

“Oh yes. That’s it. Lick my old cock as you work me with those beauties.”

I’d done it a few times before, usually with difficulty because my boobs were so big, and the guys were average. Not Max. He had a good seven-eight inches of rigid, veiny meat to work with. I licked the head of his cock and made him feel young again with my tits until he told me it was time to finally fuck.

He stood me up, turned me toward the large mirror on the wall, and bent me over the dresser. He then pulled my white shorts down in one swift motion, no panties. I watched in the reflection as he lined himself up and pushed into me bareback, slow, thick, and deep.

“Oh, so wet… yet so fucking tight,” he growled. Oh God, your pussy feels good, Megan,” he growled, bottoming out and grabbing my wide hips.

“Go slow to start with,” I panted, eyes flickering from the sudden pleasure. His cock felt good, and I secretly loved that he was so, so much older than me.

“Oh fuck, we should have done this months ago. You’re worth every dime.”

He started thrusting, steady and deep, while we both watched in the mirror. My heavy, oil-slicked tits were swinging and bouncing with every thrust. The sight was filthy and hot, watching myself getting fucked by a man in his 50’s.

I reached down and rubbed my clit in time with his strokes, faster and faster, until the combination of his cock filling me and the visual of my tits swinging pushed me over the edge. I came hard, moaning his name, my pussy clenching around him.

Max didn’t stop. He kept fucking me through it, then pulled out, turned me around, and sat on the bed again. “Ride me, sweetheart. Nice and slow.”

I straddled him, guided his cock back inside me, and sank down until he was buried to the hilt. We moved together slowly, deep, rolling grinds. My big breasts were right in his face and he buried himself between them, kissing and sucking while I rode him.

His hands gripped my ass, guiding my pace. Eventually his breathing got ragged, his grip tightened, and with a deep groan he pulled me down hard and came inside me, pulsing for what felt like forever.

We stayed like that for a while, both catching our breath as he stroked my back and told me how incredible I was.

I very, very reluctantly didn’t take the money. I wasn’t a whore and Max was too nice. But when I handed my uniform in two weeks later, to concentrate on my studies, my manager handed me a thick envelope in return. Inside was a tip from Max. A thousand dollars in cash.

I looked up at my manager in shock.

“Don’t worry,” she said. “You’re not the first hooters girl with big tits to sell your soul to Max. He’s been doing it for years. I’m sad to see you go, Megan. If you ever change your mind, you know where we are,” she said, grinning.