Lottery Winner

Prelude — An Interest of Blowjobs

(MF Mdom FSub BDSM Oral)

I suppose she was right, in a way. Money changes perspective, and a lot has happened to me since I won the lottery. But it wouldn’t have happened except for Cassie. The money wouldn’t have come, and certainly none of the things I did afterwards would have happened either. Playing the lottery was her idea, even down to the numbers we played; I even bought the ticket on one of my days with her.

It was an early November day, and errands brought me to the Short North when I got a text message. I was in C&C’s Leather Or Lace, mainly taking in the scent of leather. I was also talking to Carl, one of the proprietors about his more expensive floggers, and looking through the new toys with an eye on expanding my toolbox.

I flipped open my phone, and smiled to myself when I saw the message. It was from Cassie, and was simply “dads pmt here.” I texted back a quick “brt,” and finished my conversation with Carl, who was telling me where to purchase buffalo hide that had been tanned appropriately for a flogger. At over $200 I wasn’t quite ready to buy his yet, and he was a crafter, so he got the whole do-it-yourself thing. I work from home, and often have downtime during which to make things. A decade of customer service — and nearly as long in the scene — allowed me to finish the conversation politely, tentatively agreeing to come to his whip-making demo over the weekend.

I left his shop, and headed up High street to her place, trying not to crash. It wasn’t easy, my mind was on Cassie, and the smell of leather had me horny already. Not that it was a long trip from normal to aroused for me, but I’d traveled it before I got in the car. Thankfully, Cassie lives less than a mile from the shop, in an area I quaintly called the car-B-cue zone, after some over zealous football fans -cum- rioters a few years ago. She inhabited a single bedroom basement apartment that I’d helped her qualify for, and to outfit appropriately for a college student out on her own.

She was a freshman at OSU, only a smidgen over five feet, and round like only someone with her Italian heritage can be. She had full breasts which were still reasonably firm, but probably wouldn’t stay that way, and a wide hips that were perfect handles when we fucked. She also had one of the most talented and capable mouths I’d ever experienced and, well, given my history that’s quite a compliment. She was also a brilliant biochemist, and blew me away with her insights pretty regularly.

My phone buzzed, vibrating against my hardening cock, and I pulled it out of my pocket while I waited to turn onto the alley behind her house. I could drop by her place pretty much anytime for a quick suck and potential fuck, payment days were special. They were on her schedule, and she usually planned something nice for me; to peak my interest, as it were.

I turned into the alley, and flipped open my phone. “Wtg 4U,” the text read, and I smiled to myself. Yep, interesting indeed. And to explain the joke: late in August, I found myself in receipt of a large payment, and Cassie found herself in receipt of some large bills. Enough that it was going to put her housing in jeopardy, since Daddy had only promised her a stipend after paying tuition. That, or she could go home to Toledo, and go to school locally.

I pulled into the gravel parking lot behind her place, and put the parking tag up on my mirror. It came with her place, but she didn’t have or really need a car. She was close to campus and the main bus routes, and knew how to get a ride from me or probably half a dozen other guys if she wanted.

I took the half stair down into her apartment unlocking the door with my key, closing and locking the door behind me. Her place is one long hall with a small kitchenette and ending in a single room, which was living room, dining room, den and boudoir. She had wooden futon, which was currently upright; a small desk facing the one window in the place; and a bookshelf with a small TV on it. She was sitting in her desk chair, wearing a short pleated mini, and a button down shirt that wasn’t really buttoned up. One button strained to keep her in, and I knew it wouldn’t for long.

Her right knee swung back and forth, closing her legs, and then opening her skirt. The requisite white cotton panties were nowhere to be seen. “You like?” she asked, and I looked up at her face. Her shoulder-length hair had been tied up in a couple of ponytails, and she was chewing gum. She looked right at my crotch, and said, “Never mind, I see you do.”

She gently pushed me, making me sit on her futon, and knelt between my legs, pulling my pants down as she went. She smacked her gum, made a big show of swallowing it, and then grabbed the base of my cock with one hand, and sank her lips over its top, her tongue finding the whole in the tip, and began to lick and suck my cock.

I reached for her pony tails, and she brushed my hands away. “Not yet,” she said, taking her mouth of my cock for a brief moment before engulfing me entirely, something she always did right away, every single time since the first.

She was good to start with, but she’d only gotten better. I don’t know if she was better overall, or had just refined her technique for me. I never wanted for blowjobs, but since meeting her, I’d had many many more. Not enough, of course, but there’s a fine line between “enough” and “too much.” While you can quickly go from one to the other, I was sure I wasn’t anywhere close to too many blowjobs.

My cock was buried down her throat, and she was just holding herself there, swallowing a little, and not breathing. Her nose pressed into my groin. I noticed that her hands were up her skirt, though, and I brushed the shirt back a bit, enough that her tits fell out of it. Their light brown skin contrasted with the too-white of the shirt, causing my cock to twitch in her mouth.

She pulled off my cock then with a gasp and cough, catching her breath. Her hands were working her cunt, and she began to bob up and down my cock in time to her own fingering. Her breasts bounced, brushing against my thighs, and all the tension that had built since I entered the sex shop just exploded out of me and down her throat.

She yelled then, my cock still in her mouth, as she had her own orgasm. Her lips clamped around my softening cock, slowing and reversing that progress. One of her hands fondled my balls, and she looked up at me, flashing her eyes happily, as worked my cock back to full hardness.

The ponytails danced around as she sucked on my dick, getting me hard. I reached for them again, and she brushed me away again. I knew what I wanted, so I glared at her, as she looked up at me. “It’s payday,” she said, pulling off my cock again. I nodded, and let her continue. I was a bit frustrated that I couldn’t have my way, that she was playing with the rules that we had, but her spirit was half of what was wonderful about her, so I let her have her way. I could get my payback later.

The thought of that, her lips, and her fingers on my cock and balls was all it took to revive my old dick. She could always get two or three out of me, lending me some of her youthful enthusiasm or genuine hotness. She lifted up off of me, turned her head and wiped her mouth. Then she engulfed me again, and pulled right off of me. “Ready to fuck?” she said.

“Condoms?” I asked

“Already on.”

I looked down, and she was right. “You’re good at that,” I said.

“I’m motivated,” she said, and climbed on the futon, flattening out as I stood up behind her. I flipped the blue and green plaid skirt up, exposing her round ass. I grabbed my handles, and pressed into her, finding her pussy, and sliding my cock inside. She was wet and ready, and let out a moan as I slid home.

After just coming, I was going to last a while, so I decided to play with her a bit. I slid all the way in, then all the way out. Then I just penetrated her with my cock head, which felt really good to me, but just wasn’t enough for her. I did that a few times, then thrust home once or twice. She let me know how much she liked that, moaning, and pushing her ass back up at me. Finally she was squirming below me, so I settled into a steady pace, pounding into her, my balls slapping against her clit, my hands firmly on her hips, holding on as a fucked her.

She started to come, and I thrust into her as she cried out. I laughed, happy to be going what I’m doing, and dominant, making her come. That day she was unabashedly my submissive.

That day, in her apartment, things progressed well. I held on to her hips, her ponytails bounced, and I slammed into her. She came a couple more times from the intense fucking, and then I pressed against her. I put a foot up on the futon, and moved my hands to her back. I reached to pull on her ponytails, but again, she asked me not to. I slapped her ass in frustration, and she laughed.

So I fucked her harder.

In this position, I got really deep inside her, and I was over her, above her. She was pressed into the futon, and she was mine to use. I fucked her hard, my cock sliding in and out of her faster and faster. I put one hand on her neck, holding her down, and the other on her generous hip, holding her still as I pounded her. I let go of my control then, still gripping her
tightly, but losing myself in the sensations around my cock, my balls, her cunt tight around me. She started to come again, this time a really big one, grabbing my cock. I pressed into her, and she gasped, and I came.

I cried out, holding her out, feeling my cock shoot, and shoot again, filling the condom, and then once more. The neighbor upstairs, who was home pounded on the floor to tell us to be quiet. We laughed together then, and I collapsed next to her on the futon.

I pulled off the condom, and tied it off. “I thought you were going to do the call girl this time,” I said.

“Next time, I promise,” she said. “That needs more arranging, and better clothes. Here’s your envelope, sir, courtesy of Daddy.” She handed me a plain white envelope, with “LW” written on the side, and a nice chunk of green bills on the inside.

“So you’re done?” I asked, putting the envelope on top of my pants.

“I’m done with you,” She said, smiling up at me, her eyes twinkling. She arched her back and continued, “That is, if you’re done with me.”

“I’m an old man,” I said laughing. “Give me a few moments to recover.”

She laughed, and patted the bed beside her. It was a single, so I scooted behind her, and she spooned up against me, her skirt still bunched up around her waist, our skin touching. I draped a hand over her, and cupped her breast. She snuggled back against me. As I drifted off to sleep, I thought about how we’d met and why we were together, and that little envelope of money she’d give me after we’d fucked.

---

I met Cassie at a munch, a little public get-together for kinky people. I found out later that she was a bit young for it, according to the rules and laws of the State of Ohio. But that was later, after we’d adjourned to my place. Something about her had caught my eye (somewhere between her bubbly personality and her bouncy breasts.) So I invited her to my home, and we sat around my coffee table drinking wine and chatting about the scene.

I promised to flog her soundly — at some future date. I don’t play when I’m tipsy, much less as drunk as we were getting. Still, she was so excited, she’d paid me off with a blowjob right then.

She unzipped my trousers, pulled me out and engulfed me with her throat. All I could see was her wavy brown hair splayed out over my lap, and all I could feel was her hot wet throat squeezing my cock. In no time she was bobbing up and down, nibbling the tip, then swallowing me whole. Very soon I passed the point of no return, and she was looking up at me, licking her lips and saying, “Not bad for an twenty year-old, eh?”

“And here I am supporting underage drinking,” I said huffily, but not really angry. I mean I just got an awesome blowjob, right?

She giggled. “I had to do it now, before I pass out.” While she still had liquid courage, I guess.

We sat on the couch and talked, and kissed. “Why me?” I asked. “I’m not exactly the young good-looking type.”

“And I am?” she asked. She was beautiful, but in a way that a twenty-year old probably couldn’t see. I just nodded and smiled at her. “That’s part of why,” she said. “The way you look at me. And the other said you were safe, and good with newbies.”

I kissed her then. It was reasonably true, what she said. I had a reputation in the community, a fairly good one that I’d established early, and worked hard to maintain. I was a safe player; I was good at negotiation; I had a lot of varied skills. I could teach (and had taught) a lot of submissives and other dominants. Only I knew that I wasn’t really safe, that I had desires way beyond anything I’d let myself do. Some of them I wanted to do to this beautiful, round, way-too-young girl on the couch beside me. “Safe, huh?” I said with a smile.

“Not really,” she said, her hand caressing my forehead. “I can see it in your eyes. It’s controlled, but powerful.” I kissed her again, and she whispered, “I wish I wasn’t so drunk.” I felt the same way.

She wouldn’t let me do anything to her that night. Nor would I let myself. Our conversation dwindled down until she fell asleep curled up against me on the couch. I slowly extricated myself, draped a blanket over her, and went to bed.

The next morning, Cassie woke up with a mild hangover, and a demand. She walked into my kitchen, barely dressed, and declared, “You owe me a flogging.” She grinned at me, and stretched. She wore only the simple t-shirt that she’d had last night. It was fine with her evening ensemble, but as she was naked otherwise, I got a glimpse at her full bush as the t-shirt rode up.

“A debt I’ll gratefully pay,” I conceded and handed her a cup of coffee.

She rubbed her temples. “Too much to drink,” she said. “And too much to do. I’m staying with some friends right now, but I’ve got to get on my feet first. Find a place to live. Find a way to pay for it all.” She told me about her situation — she’d lived at home in Toledo for her first two years of school, always planning to transfer to OSU. Daddy had agreed, and was willing to pay, but wasn’t helping at all. “He thinks he’s just giving me enough rope to hang myself,” she said.

I nodded, “So how much do you need to get settled?”

“Six grand pays my bills, gets me an apartment and furnishings. Daddy took care of the school expenses, and is giving me enough to live on — just not enough to start out on my own.”

“And he won’t advance you any of it?”

“No, this is his way to make sure I come home. He knows what it’ll cost to get settled here. And he’d forfeit the tuition money to get it, too.”

I knew if she went back now, he’d get his money back, and tuition at OSU wasn’t a small amount of money. I also knew that I’d just gotten a early completion bonus that more than covered what she needed. I was going to upgrade the servers here, but that could be done in several smaller steps. I also knew she was sitting at my breakfast table wearing nothing but an almost-too-short t-shirt.

I’m in my forties. Twenty year old girls don’t come home with men like me very often; they don’t give us spur of the moment blowjobs either. It happens sometimes in the scene, where I was a well known mentor, but that was different — people of all ages and walks of life are in it. Someone might have told her about me, and she might be interested, but she couldn’t be sure of what she liked yet, either. Few people did at her age. She seemed the right type to me: sexually comfortable, interested in learning and exploring, and a bit of submission deep inside her, coupled with a desire for independence.

And that’s what decided me. I wanted to keep her around. So, I made my offer. “I could advance you the money,” I said. “If it’ll keep you around.” I smiled at her in a way I hoped wasn’t too predatory.

“Just like that?” she asked.

“It’s a loan,” I said. “You can pay me back as you get your stipend from ‘Daddy’.” It wasn’t that simple of course, there was something I wanted. She didn’t seem unwilling, but I still pressed her on it. First with the loan, and then with more.

“You’re just going to give it to me?” she asked. “And all I have to do is pay you back over the next year?” She seemed incredulous. Excited, but uncertain to have a strange man just give her a bunch of money. I touched her face, as she looked up to me. She was near tears in relief and stress and uncertainty.

“I could charge you interest,” I said. “But that would leave you less to live on.” I admit I was standing there, fantasizing about the night before. I wanted to keep her around, but not just to have her in the city. I wanted more, but she was young and inexperienced. But smart, very smart.

Her hand brushed my cock; it was getting hard as I stood there next to her with the memory of the night before and the fantasies of future nights ahead running through my mind. “I could offer something else. A blowjob, a fantasy when I pay you. Would that be interesting enough?”

God, I thought when she said it. Was she reading my mind, my desire? If she was this willing, could I push it further?

“You’d plan it?” I asked. She nodded. “You’d be my slut? My call girl? My schoolgirl? My harem wench?” She nodded to it all. “You’d plan it, and I’d come along for the ride, and then you’d pay me for it all?” She shuddered then, and nodded.

“Yes,” she whispered, and looked away. “Once a month, I’ll pay you the money from Daddy, then I’d fuck you and blow you; be your fantasy. Please.”

I touched her face, and she looked up at me, and then I knew. “I want more,” I said. Her nipples pressed against the t-shirt, her face pressed into my hand, still looking away from me. She was flushed, warm and excited. Her headache, I was sure, was gone now. “You’re going to be in my debt all year; interest is always accruing. I don’t care if you date other boys, or even men. But I want a blowjob, whenever I want a blowjob. You understand?”

She shook her head, and looked up to me with an unsure, uncertain look in her eye.

“I don’t have regular hours,” I said. “It could be eleven in the morning, I’m horny, and I’ll call you. It could be 2 am, or dinner time. I’ll call, and if you’re not in class, if you’re not busy with school or plans, you’ll be available to me.” She shuddered beneath me, and moaned. She was coming from the idea, if only a small one.

“What if I am busy?”

“If you are busy, and it’s not class, you’ll be punished. And then I’ll fuck your throat.”

She closed her eyes. “I don’t know. I don’t know if I’ll like that or not.”

“It’s punishment,” I said. “You probably won’t.” I kissed her forehead. “Think about it.”

I walked into the other room. I needed to cool off, and find a couple of things that I’d need if she said yes. Keys. Condoms. Bank card.

“You want me to be a whore,” she said from the doorway between us.

“No,” I said. “The money is a loan, you’ll pay it back. It’s friendly, no interest. But I’m offering you the loan to keep you around. I want to fuck you, to top you. I want you to give me more of those wonderful blowjobs. I’m willing to risk some money to make it happen.”

“You liked it that much?” She blushed, and kind of smiled up at me as she said it. Her hair caught the light from the kitchen, and glowed a bit making her beautiful. Her nipples made sharp tents in her t-shirt, making her desirable. I nodded, and moved toward her. She backed into the kitchen, until she hit the table. “Are you going to fuck me now?”

“Yes,” I said, brandishing a condom. I leaned toward her, and she leaned up and we kissed, a perfect eternal moment.

“Oh, God,” she said. “You don’t kiss like other boys.”

“That’s because I’m not a boy,” I said, and lifted her up onto the round breakfast table. She smiled at me, her eyes capturing the morning light. I kissed them then, and she sighed against me. Sometimes she was a talented woman, and sometimes she was a girl. I wanted the woman, but the girl was what made it wrong. Was what made it hot. It’s what kept me from waiting. I wanted her right then, not later.

The first time I took her, I could have taken her to my room, to my bed. Being an adult means not having to improvise in the back seat of a car, or on the couch while the parents are upstairs in bed. But she was there, and I was there, and that was all that was necessary. I kissed her again, and our tongues touched and played against each other.

My hands found the hem of her shirt, and lifted it up. I broke our kiss, and lifted it above her head, dropping it on the table behind her. She leaned back, and I lowered my mouth to her breasts, first teasing one, then the other, and finally settling between them. She pressed and rubbed her breasts against my head, while I moaned against her skin.

Cassie grabbed my shorts then, ineptly pushing them down over my hard-on and let them fall to the floor. I groaned at her need and the sensation, and picked up the condom I’d brought with me to the kitchen, tearing it open and rolling it on. The table was the perfect height. I’d seen to that, although I’d never used it for quite this purpose.

Her pussy was ready for me, and right there. It would have taken more effort not to slide into her. She was warm, and wet, and gasping as I filled her. Her hands clawed my back, and her legs wrapped around me, urging me on, and I fucked her there on the table.

My own hands slid between us, grasping her breasts, and pushing her down. She reached out to the edge of the table, holding on, and I teased and mauled her breasts, while I fucked her. Her legs worked me at the rhythm she wanted, which was fine with me then — I just wanted her. Control would come later.

She began to talk then. “Make me your whore, make me your slut. Your call girl, your blowjob queen. Fuck me, fuck my cunt, fuck my mouth, god fuck me!” Her head thrashed back and forth, her hair covered her face as she spoke. She looked wanton and hot. Her breasts bounced under my hands as I teased and touched them.

I stopped teasing her breasts, and just grabbed them; I leaned over her and fucked her hard, taking my own pleasure. She moaned, and began to come. Some part of me realized it was the first time I’d made her come, and I drove my cock deep inside her as her pussy clamped down on me.

I’d like to say I rode her to some more orgasms, but not that day. Not the first time with someone new, someone as hot as she was. I came soon after her, filling the condom, and then collapsed beside her on the kitchen table, while she lay there and twitched.

“So, will you fuck me like that again?” she asked dazedly.

“Not right now,” I laughed. I was limp and sated.

“But if you loan me the money, you will.”

“Cassie, I’ll do it whether I loan you the money or not.”

“But if you don’t, I”ll have to go home.”

“That’s a possibility,” I said.

“Okay,” she said.

“Okay?”

“Yes,” she said. “Let’s do it.”

---

Three months later, and I was lying next to her in her apartment, sleeping after my third payment. There were still nine to go, but that day everything changed. As I stirred from our nap, my movement woke her up. She was still cuddled tight against me, only now her nipple under my hand was stiff, and my dick between her ass cheeks was hard.

They say you are as young as the one you sleep with, and my cock was taking it to heart. She stirred against me, and made a happy noise as she wiggled her hips. I worked my hand out from underneath her, and took hold of her ponytails, pulling them back, baring her neck. She gasped, and I nibbled at her neck.

I squeezed her breasts, treating them roughly and she just pressed back against me. I gave a low evil chuckle, and slid my hand down her body. She turned in the bed, parting her legs, and I slid my fingers down to her lower lips. “You like me pulling your hair?”

“Yes.”

I rubbed her still-wet pussy lips. “So,” I said, pulling her hair a bit harder. “Why didn’t you let me pull your hair earlier?”

“Uh…mmmm,” she replied. Admittedly, she was distracted by my finger moving against her clit, and my teeth nipping at her neck. I moved my finger away, and she whined.

“You should be punished for that,” I said, pinching her thighs lightly several times as I spoke.

“Yessss…” she moaned. I doubt she knew whether she was responding to me, or the way the pain felt. I knew she liked it.

“I’m glad you agree,” I said. I kissed her neck, and she moaned, turning, trying to get my hand back where she wanted it. I let her go, and she sighed. “Onto the floor.”

She slid out of bed onto the floor, and I sat up, with my legs on either side of her body. I grabbed her pony tails again, and said “Open.” Before she could do more than react, I pulled her down, over my cock. She gagged for a moment, then moaned as I began fucking her mouth.

“This is your punishment,” I said. “I’m not going to fuck you again today.” She whined around my cock. I admit that just made me harder. “But I see no reason why I shouldn’t get off.”

She mumbled something incoherent around my cock, and when I didn’t respond, she slipped her hands between her legs. She was still wearing that little plaid skirt, and her hands disappeared under it, and jerked back and forth. Sure she was twenty, but I was fucking the hot mouth of a schoolgirl. Perhaps that sounds crude, but it started to push me over the edge.

Her orgasm is what did it though. She was shaking her whole body, vibrating around my cock as I continued to fuck her and then I thrust into her and came, shooting in her mouth. I pulled out of her, and she knelt there, a bit of a dreamy look on her face, and my come drooling out of her mouth. She licked it off, and smiled at me.

I smiled at her, and felt a real connection with her.

We weren’t exclusive, just two people who fucked. But I think I was falling in love with her even then. It was stupid, she was less than half my age. If I’d known what was going to happen, I might have left her then. I might have loved her enough for that.

But if I had, it wouldn’t have happened at all.

I stood up, and started getting dressed; Cassie shucked the rest of her clothes, and crawled back into bed. When I picked the envelope back up, she asked me, “What are you going to do with all that money?”

“I dunno, I just got paid for some work, so I’m not strapped for cash. Mega-Millions is way up there right now.”

“You’re kidding me, right?” she said.

“I dunno, it’s at 280 million,” I said.

“You might as well give it back to me then,” she said.

“I’d only buy one ticket,” I said. “I know better than to waste it on the lottery.”

She got a kind of quizzical look on her face. “So, if you won, would I still have to pay back the money I owe you?”

“Of course not,” I said. “But I’d miss paydays. And I wouldn’t mind if you paid back all your interest.”

“Sounds cool,” she said. She streteched and yawned. “Sorry, I need a nap before my date tonight.”

“Keeping a busy schedule?” I asked.

She shrugged. “He’s cute, but he’s not you.” I leaned over and gave her a kiss. She smelled of sex, and tasted like my come, but that never bothered me. She kissed me back tenderly, and I headed for her door. “Go ahead,” she said. “Play the lottery. Use our birthdays, why don’t ya?”

“Sure,” I said, smiling down at her. I kissed her one more time, on the cheek. And left her place, locking up as I went. I pulled a bill from the envelope, there was a convenience store half a block from her place. I could get a soda and a lottery ticket. It might be fun.

It didn’t really matter, after all, there was a one in 170 million chance of winning, and I was only going to buy one ticket.

Still, things happen sometimes. They certainly did to me.