Sugar Daddy

To be honest, I still wasn’t over the weird feeling I had about using a site that helps connect young women with sugar daddies when he sat down at the table.  


I was a junior in college at the time, and bills were stacking up. I had a friend who’d been using sugar daddy sites since freshman year with almost no problems. While I was eating beans and attending a Desi culture, Bible Study, and Jewish studies club every week to eat the free food offered, she was eating Chipotle every night. She had a Fenty highlighter in every available shade, and her textbooks and a chunk of her rent were paid for. 


I was a couple of weeks of kidney beans for dinner deep when I figured I was ready to suck an older man’s dick for that Chipotle-every-night money. 


However, when he sat down across from me at the table, the reality of it really sunk in. 


I have never been particularly seductive or charming or diminutive in the way that girls get rewarded for. I definitely look the part, but all that is usually ruined the second I open my mouth.  


He introduced himself as Leon and reached his hand across the table, and I felt only anxiety. Could I make this work? 


Could I pretend to be a stupid blonde girl for long enough to get paid? How long until he saw through me? How long until he realized that even though I’m skinny and blonde and young I am very tired and very bitter? 


Could I put on a happy face long enough to get the electric bill covered? Being able to have the AC on in July would be great.  


I put on a smile for Leon.  I figured it was either doing a customer service job where I made absolutely nothing to put up with a bunch of people’s bullshit or doing this and getting extravagant gifts to put up with one guy’s bullshit.    


I would have been a stripper, but I have the rhythm and flexibility of a steel beam. 


Also, Leon turned out to be a lot more attractive than your average angry 40-year-old mom demanding a booth last minute during the dinner rush at Chili’s. 


However, that also played into my nerves a lot. Leon was an established, wealthy and attractive architect in his 50s. I really wanted to know why the fuck he was looking for women on a sugar daddy site. Women of all ages had to literally be throwing pussy at him from across the room all day long. 


I assumed that Leon wanted to shake hands, but when I held my hand out to him, he flattened my palm and kissed my knuckles. The warmth of his lips shot sparks up my arm. In 19 years no one has ever kissed my hands in any capacity. Honestly, it was the last thing on Earth that I truly expected.  


“Order anything you want,” Leon said.  


That’s when I opened the menu and realized that we were at one of the most expensive restaurants I have ever been to in my entire life. There wasn’t even an appetizer that cost less than $25. 


Part of me hysterically thought to order one of everything just in case this was my last ever date with him. I wanted to get the most possible out of this transaction.


Then, I remembered that it was only lunchtime, and we had agreed to go shopping together after. In the end, I opted for a lobster and truffle linguine. It was one of the only things on the menu that I actually recognized. It was also expensive enough that it made me feel like I was getting my money’s worth. 


Leon ordered something I couldn’t pronounce and a bottle of wine for the table. I watched as the server looked at him and then looked at me. He was definitely considering carding me. He could 100% tell I wasn’t old enough to be having wine. 


A quick glance from Leon sent him on his way. I wasn’t exactly sure what happened there. Later I would learn that Leon went to eat there about twice a week and the entire staff knew him. They would give him basically anything he wanted all the time. 


My pasta was incredible. I quickly decided that from that moment on I was going to ride this thing out to the absolute fullest. I wanted more pasta. I wanted more Lobster. I wanted that Fenty glow. I wanted my electric bill paid for. 


Leon and I didn’t speak very much, but it was a comfortable silence. At some point, our feet had curled together beneath the table. It was almost like this was an actual date or something, but was it? 


I wasn’t sure. The closest thing I had experienced to a date in college was a guy inviting me to a party at his apartment. By the time I showed up he was so wasted that he had already blacked out unconscious in a chair. I had some free beer and went home alone, pretty faded, at about 1 am. 


Incredibly romantic, I know


Considering I hadn’t been on a bunch of regular dates, and I had never tried the whole sugar daddy thing before, I felt pretty out of my depth. I wasn’t really sure what was going on or how to qualify it at all. I decided that I would leave all that shit to Leon and just enjoy my pasta.    


I think I had only had Lobster once before in my life. It melted in my mouth like some kind of decadent oceanic dessert. I wanted more Lobster, and Leon was my Lobster Guy. He was my hookup. He was my connect. 


“How do you like it?” He asked after a while. I’m pretty sure that was an almost redundant question because I had been audibly moaning throughout the entire meal.    


Later, I would learn that one of Leon’s main pleasures is giving other people pleasure. But I had yet to learn how deep that actually ran with him. 


I was honest with Leon. I told him it was the most delicious thing I had ever eaten. I expressed that I’d never really had Lobster before. 


The look Leon gave me in return was almost heated. He has dark brown eyes on the verge of black, and they almost seemed to burn. 


Leon likes to be the first in all things. He really liked being the first to feed me lobster. He wanted to expand my horizons. He wanted to do so in many ways. And I was more than happy to let him.  


We finished up lunch and wine. I only had a little bit; just about half a glass. Honestly, I knew the wine was expensive and probably tasted great to bougie people who knew things about wine, but to me it tasted like vinegar. At that point in my life, my favorite wine was Franzia. I really loved the notes of cardboard, like the box it came in from the gas station. 


Feeling full and satisfied with such rich and delicious food was amazing. It was a sensation that I had forgotten. It had been a rough few semesters. And while before I left for college I wasn’t exactly eating lobster every day, my mom would always have enough Hamburger Helper on the stove for everyone.  


After lunch, we walked around the city center from store to store. We wandered from Anthropologie to Aritzia to Coach to Bloomingdale’s. I wondered just how much money Leon made at every store when he pulled out a black credit card. He let me buy anything I wanted. It was as if money flowed out of an endless tap for him and was clogging his sinks. He didn’t even notice it dripping from his hands.  


There was only one stipulation. If it was clothing, I had to try it on for him first.  


The first time it was a little bit humiliating. I couldn’t really get used to it the rest of the time, either. I felt like everyone working in the store watched me as I went into the dressing room with a $1000 glitzy gown. I felt like they could tell that I didn’t need or deserve things like that. I felt like they could tell that the fanciest event on the horizon for me was the Desi’ club’s Garba celebration I would be attending with a tin-foil lined purse. 


I took a deep breath and came out of the dressing room in it for Leon’s inspection.  


Perhaps inspection is the wrong word. His eyes would scan me from head to toe and then rescan me from head to toe. Sometimes he would even have me spin. He never really critiqued anything or shared any of his thoughts whatsoever. 


But I could tell by his gaze that he loved this gown on me.   


I stood in front of the large floor-to-ceiling mirror in the store. The dress was blood red and hung down to the floor, but left most of my back and shoulders exposed. He came to stand right behind me. As my entire back was exposed I could feel the heat of his body burning through his shirt against me. He placed a hand on my waist, and it seemed almost like a strange kind of gravity was pushing us together. 


Out of the corner of my eye I saw one of the sales associates pretending not to watch us. Her face twitched. Up until that point, she likely thought that Leon was my father. I watched as her confusion turned to an uncomfortable understanding as his hands slid slowly down my exposed back. His fingertips stopped where the fabric met my skin. They couldn’t slide beneath, but I could feel how much he wanted them to. 


I shivered. I had turned my head to take in the expression of the sales associate. I had left the long line of my neck exposed. Leon’s lips hovered there and I found myself desperately wishing that he would make contact. 


One of his large hands was on my stomach over the silk of the dress and his thumb was lightly stroking it.  I could not help but melt against Leon. The gown was thin and silky and I felt as if I was standing naked in the store. I felt like all the employees were watching him stroke me through the dress and inhale my scent. 


“What do you think?”  Leon asked me, and I had fallen so deep into his gentle touche that I don’t think I even had the language to answer him.         


“Do you like it?” He asked just as his thumb slowly skidded down my torso.  

I thought at that moment that I wanted his hands to keep going. I wanted him to touch me through the dress where I was throbbing. I don’t think I’d ever been turned on like that before in my life.   


“Yes,” I finally said and felt like an incredible act of will to form even that single word. 


“Do you want it?”  He asked me and my brain short-circuited. I wanted many things. I considered grinding against him in the store. 


I settled for leaning back ever-so-slightly. He inhaled sharply, and I wondered if maybe I was far more seductive this entire time than I had realized.


Maybe I could make this work after all. Especially if Leon continued to make it so fucking easy.  


Many thoughts ran through my mind. If he wanted me and I wanted him and he wanted to buy me things and I wanted to be bought things, then what exactly was the problem?  


I slid my hand between my stomach and his palm. He laced our fingers together. Our joined hands skimmed my torso and came to rest on my hip bone. His hands were much larger than mine, and his thumb still rubbed tiny circles into my hip. I felt like I was burning alive.     


“I want it,”  I said.      


“Good girl,” Leon whispered in my ear.  I had taken off my panties to try on the dress and I hysterically wondered if I was so wet that I was dripping onto the floor between my feet under the gown.  


I felt like I was going to explode.  


When he detached himself from me to go announce to the sales associate that we would be taking the dress and a few other things, I felt suddenly unanchored. I was dizzy and turned on. I was running hot. The sudden lack of touch was like a slap in the face. I was freezing.      


Going back into the dressing room alone to take off the dress and get back into my normal skirt and sandals felt wrong. I wondered what strange and surreal world I had entered. 


I stood next to Leon as he paid for the dress and all of the jewelry I had chosen.  All together it cost nearly $2,000. And that was just at the one store. He had spent maybe three or four months of my rent in an hour. I felt dizzy. 


I could feel the eyes of the sales associate on me, and I wanted to play a little bit.     


“Thank you so much,” I said as Leon swiped his black credit card. “I love them.” All three of us were a little bit surprised when I kissed him on the cheek. I’m not sure if Leon or the sales associate was the most surprised.  


When we left the store, I was carrying four shopping bags and Leon was carrying three. I honestly couldn’t even remember the extent of everything I have bought or how much it cost. But I did know that I wanted to fuck Leon really really really bad.


We stood in silence for a second on the sidewalk just looking at each other. We were overloaded with all of my bags.  I was pretty sure that he wanted to fuck me too.  


Usually, I was not so bold. But something about having a man rub my hip bones through a silk dress in public for an eternity while he breathed into my hair had, had me soaking wet for what felt like hours. 


“Can I kiss you?”  I asked. Leon looked absolutely floored, but he ducked down so I could take the kiss I wanted.  


It burned like fire. We were both trying to wrap our arms around each other, but couldn’t because of all the bags.        


We pulled apart and Leon looked incredibly confused. I wondered if he took out four different sugar babies a week and none of them ever really wanted to fuck him.  


Leon was an almost 50-year-old man with beautiful dark eyes, a full head of salt and pepper hair still clinging to some of its original jet black. He kissed like the devil and could drop five grand in four hours on a shitty 19-year-old like it was no problem. On our first date, he was even wearing a black button-up shirt with the sleeves rolled up, revealing muscular forearms with thick dark hair, like some kind of sexual lumberjack cliche. 


I don’t really know what more Leon could do to be devastatingly fuckable. If he was any more fuckable it probably would have been illegal.   


“Do you want to come by for coffee?”  He asked and I couldn’t help but laugh a little. That was so old school, so Seinfeld. No one in real life had ever pulled that one out on me. 


I said yes, and we walked a few blocks. His building almost seemed to blend into the surroundings. I had passed his place a thousand times while doing things in the city and had never even considered it.  


Inside, however, it was a veritable fucking palace. It almost reminded me of an old school hotel with uniformed staff sitting at the desk and waiting at the doors to help people carry things. For a second I wondered if it even was a hotel. It had that old world rich Art Deco look and thriving plants as green as gemstones everywhere. Even the elevator was plush and red and gold inside.   


He placed my shopping bags on the ground, and I did the same.  


Again, there was that strange gravity. Our hands joined somehow. Then we were facing each other. His hand was on my face. Leon took a strand of my hair that had come loose from my bun and tucked it behind my ear.  


“Coffee? He asked, and he sounded breathless already. 


The sound of Leon’s voice like that did things to me. It was rough like we had already spent hours in bed. Instead of answering him I tilted my head back and parted my lips. I waited for him to swoop down and kiss me like I wanted.   


He gave me that too, and it tasted like an absolute victory. He picked me up like I weighed nothing and pressed me against his closed front door.


Leon’s hands held me up by my ass, and my legs wrapped around his waist. He squeezed one of my ass cheeks in each hand, and I couldn’t help but try to grind against him. 


I needed to be even closer.    


I was wearing a long silky midi skirt, and it pooled up around my hips. It did almost nothing to separate me from Leon where I most wanted him to touch me. He kissed me long and deep. My heart was pounding. I moaned openly when he sucked my tongue into my mouth.  


Suddenly we were on his sofa. It was a luxurious and buttery deep reddish-brown leather. When he plopped me down onto it, I felt like I was sinking into cool clouds.   


My legs spread of their own accord, we could both see just how wet I was through my panties.  I suddenly felt the urge to cover myself. I went to move my hand down so he couldn’t see how much I had soaked through my white panties.     


He caught my wrist. 


“Let me see,” Leon said and for the first time in the entire day I felt shy.  I flushed with embarrassment down to my chest and he followed it with his eyes. I felt like he was devouring me alive piece by piece with his eyes alone.  


He pressed two fingers against me where I was wettest suddenly and the shock of it sent me reeling. He ghosted his fingers against me through my panties. Leon stroked softly until I started to push against him demanding more. Steadily, he gave me more and more pressure but it wasn’t enough.           


Leon seemed to pull off my panties and skirt in a single motion. Before I realized what exactly had happened he had two fingers deep inside me. 


I hadn’t had sex in months and even just those two fingers felt so big inside me. I was gushing wet and throbbing inside. I was so turned on that I seriously felt like I could have died. 


I felt myself shaking inside around his fingers. I wondered at that moment how I would ever take his cock. Even at that point, that’s all I was really thinking about. It had been so long since I had even had sex. I wanted to see it. And I wanted to feel the stretch of it deep inside me.   


Leon remarked about how tight I was. Then he looked into my eyes and said something that almost made me pass out beneath him on his sofa. 


He said that he was going to have to get me ready first. He said he was going to have to stretch me out because I was so fucking tight. 


I thought he was just going for dirty talk, but then I looked into his eyes and he looked genuinely concerned. Leon asked me if I had ever had sex before, and I turned beet red under him. 


“Am I your first?” He asked. I felt too embarrassed to answer. I tried to shake my head. But, when I tried to answer, Leon started pressing down against my clit while he fingered me. My head fell back against the sofa and my legs spread even wider. I was beyond ready to let him do even more of whatever he wanted with me. 


He decided then that he was my first, and I wasn’t about to take that away from him. I shuddered as he worked my clit until I dripped down his fingers. 


I was desperately riding his fingers, and he kept kissing me and breathing heavily into my mouth. He smelled so good and it was driving me absolutely insane. 


“Please!”I finally begged. I don’t even know what I was asking for or what I wanted Leon to do. I wanted more and I wanted it immediately and I wanted him to give it to me.  


“Please, what?” He asked as he twisted his fingers inside me. I let out a long low moan of pleasure. 


“Please, what?” Leon asked again. He sucked a bruise into my neck and I felt it all the way down to my throbbing core. 


“Tell me what you want,” He said. “If you don’t tell me I can’t give it to you, baby.”   


My face and body were on fire, and my pussy was throbbing.


 “Fuck me,” I finally said.       


“Anything for you.” Leon said. I watched as he got just far enough away from me to unbutton his jeans. He peeled down his jeans and underwear just far enough to take out his cock. 


He is a tall man and his cock was big and thick to match. I felt myself quiver inside as it sprung up, hard and ready to be inside me. Leon took a condom out of a little golden box on his coffee table. He slid it onto his cock with ease and sat back on his knees. 


“Since it’s your first time I want to give you control,” He said. “You decide how deep I go. You decide how fast. You decide how hard you get it. Is that okay, baby?”   


Leon beckoned me forward, and I crawled over to him to position myself in his lap so I would be ready to sink down. He held his cock at the base so it stood at the perfect angle for me to take it. I saw him carefully watching my face for signs of discomfort as the tip of his cock slid in, but I only wanted more.  


I was determined to have him inside me as deep as he would go. I sunk down all the way to the hilt in the space of a breath.  


I felt myself quiver violently inside. I have never felt such a delicious stretch and burn so deep inside me before. I ripped off my cami top and threw it onto the floor. Then I threw my bralette somewhere else. I was positively dripping with sweat as my body got used to being stretched by that fat cock.    


I felt dizzy. I swayed on some strange precipice of pain and pleasure that I couldn’t even begin to describe. I wondered if I was going to pass out.  


“Breathe, baby,”Leon said softly. And I did. I couldn’t believe that I had literally forgotten to breathe.  


“Are you okay?” Leon asked. “Does it hurt?”   


I answered by using every ounce of my strength to just squeeze down on his cock. Leon shook.  And his moan hit me like a burst of Fire.   


“If you keep doing that I’m going to come,” he said. He sounded like a broken man. 


“How about you try grinding on a little?” Leon suggested. He took in my blank stare and clarified. “Rock back and forth a little on it see how that feels for you.”   


I did. I slowly started to rock back and forth in his lap with his hard cock inside of me. It was a long sensual grind that stretched me in all sorts of directions I had never anticipated. I loved it and before I knew it, we had built up a little rhythm. We were rocking together while we kissed. He nibbled on my lips and sucked on my tongue.   


When Leon took control a little and decided to randomly pump into me, maybe even barely an inch, I nearly screamed. I turned to jelly in his lap. 


 “Oh, that’s the spot huh?” He asked and I shook my head.  


“No, it’s not?” He asked, teasing me. After a little while of sensual rocking that was making me slowly burn from the inside out he hit that spot again and my eyes rolled back into my head. 


“I think it is,” Leon said. Then he flipped me onto my back and slid all the way back inside me. His fat cock jammed right into that spot. I had never been fucked so hard before. I loved it.   


 I wailed. I think I started to cry.   


“Do you like that?” Leon asked. “Do you like being fucked a little bit harder?” 


I didn’t even know how to answer. When he slammed back inside me to the hilt, my eyes rolled back into my head, and I forgot how to breathe.  


I wrapped my legs around his waist to try and keep him inside me as close as possible. I was almost hanging off of him swinging as he fucked me deeper and deeper and deeper.   


I felt like I was on fire and like I was going to die. I needed Leon to keep fucking me more than I needed to breathe. I was screaming, and I can’t even tell you what I said.    


On one particularly deep thrust he bit down into my shoulder, and I screamed. 


“You really like it rough.” He said. Was this that rough? I didn’t think so. I just thought it was fun. “Would you like it if I slapped your ass?” 


Oh no.     


I did want that. 


“No,” I insisted. It did not sound even remotely convincing. On his next thrust deep inside me, he reached down and slapped my ass. I clenched down on his cock so hard that we both let out a small groan.  


Leon spun me around and positioned me on all fours so my hole was in the air ready for him. He slid right back into me and slapped my ass. He fucked into me a few more times and then slapped me again. It was absolutely delicious, and I was wailing. My face was pressed into the sofa. Leon cursed long and low before losing all control and fucking into me with wild abandon.  


I felt like I was going to break apart. I clamped down on his cock inside me. I was trying to take him in even deeper all the time.  


His nails were digging into my hips, and his cock was spearing me open inside. I could tell from the feeling of his thighs slapping against my ass that it was sore and red from where he had slapped me. I saw out of the corner of my eye but we had disturbed some of the bags full of the beautiful things he had bought for me. They were scattered all over the floor. I couldn’t believe that this was my life. 


Leon came inside me with an animal growl that went straight to my pussy. When he pulled out of me, I was quaking. I hadn’t come, but I was so ready to. I watched him get up and tie up the condom and throw it away in a sort of manic daze. I could feel myself clenching on nothing inside, and my body almost freezing where contact with his skin had set me on fire seconds before.


Leon came back to sit with me on the sofa and kissed me long and low. I started to rub myself desperately against his leg.   


“You didn’t come?” Leon asked, and I shook my head.   


He kissed down my neck and sucked one of my nipples into his mouth. While he teased that he applied his fingers to my clit again. I squirmed and rode his fingers as I sat in his lap. I was naked, and he was still fully clothed.    


It only took another few kisses and a cleverly savage twist of his fingers inside me to have me cumming in his lap. Leon held me in his lap. He kissed my neck and my chest and my lips as I lay boneless in his arms panting and sweating.   


Suddenly, I opened my eyes and the room was much darker. Leon had big glass doors open to a balcony overlooking the city. I could see the sun setting through them.  


I had fallen asleep in his arms earlier in the day without even realizing it, and he had let me sleep. Maybe for hours. 


I was still naked and he was fully clothed. His jeans felt rough against my sensitized naked skin.   


“Have a nice nap, baby?” Leon asked.