My Life as a Sugar Daddy Pt. 01

May 21, 2024 // By:analsex // No Comment

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Main themes: public humiliation, small penis humiliation, cuckold, forced bi, blackmail, financial domination, light racial play, sugar daddy, sugar brat.

*****

“I just love the presents you brought me, Chris! I’m impressed you followed all the requests in my ad. Our first date is going to be amazing. Most people that contact me thru my website are so lame. Just because my profile says I’m a sugar baby, they just think they can buy me a few presents, get in my pussy and then disappear. But, I liked your profile. You said you’re 45, Chinese, have a successful job in high tech. And you claim to be a REAL gentleman. We’ll see about that =) But, that’s what I really want, a nice guy. I haven’t dated Chinese guys in the past, truthfully. I’m quite tall, so I usually date white guys. But, sometimes, they can be so arrogant. They think because they have big cocks or something, they can get whatever they want. I think dating a man like you is just what I need right now in my life. Someone sweet and gentlemanly. Also, with your masters degree and your great job, I’m sure you can mentor me as well while I’m going back to college.”

“Let’s look at what you brought. A black, evening cocktail dress. Ooh, and a sexy short red dress. Of course, some matching high heels. And my favorite, some victoria’s secret lingerie. Maybe I’ll model some of these later tonight =) Let’s start driving. I picked out a great restaurant for us.”

Now we’re at the restaurant…

“So Chris, a little more about how I’d like for us to build this relationship. I can’t lie. I do like the finer things in life. I know this is an expensive seafood restaurant, but life is short. Let’s enjoy every moment to the fullest, right? =) And, I promise to give you what you need, but you do have to earn it. I’m not some slut on Craig’s List. And, I can tell from your kind face, you’re not going to treat me like some hooker, right Chris? Ah, you’re a sweetie. I know a lot about divorced guys like you. You want to feel young again with a young hottie. Relive your youth during your ‘mid life crisis’. Well, I’m going to make that fantasy come true for you!”

As we’re eating our meal, I say “Oh Chris, I see an old friend working at the bar. Do you mind me going over and saying hi? I’ll be right back”. As you wait for me, you notice that I’m taking a few shots with the bartender, a tall, handsome American man. A few other men at the bar take a shot with me as well as we all toast and laugh. After about 20 minutes, I return…

“Chris, sorry that took so long. That’s an old friend, Jake, and his buddies, and he promised to pass my resume on to his friend who works at a company I’m dying to get into. I had to drink a few shots with them to give them face. You have to know the right people to move up in life, right?”

During the rest of the dinner, I’m drunk and giggling as I keep receiving texts, which I take the time to answer. The bill arrives finally, and it’s a LOT bigger than you had expected. “Sorry hun, they must have billed all those shots to our table. Hey, but if I get that job, this will all be worth it! Oh hold on, he’s texting me about that, um, job. Let me go say bye while you take care of this bill.” I take another 15 min to chat with the bartender while you wait for me. You see him hug me goodbye and even pat me on the butt.

—————

Once we arrive back at Chris’ place..

“Thanks again for the dinner! That was so fun. Oh, so how about I try on some of those clothes you bought me?? Make yourself comfortable and pour us a couple glasses of wine.”

I come back out wearing one of the dresses you bought me and twirl around a bit. I then go back into my room and come back out with the lingerie. Then, you move toward me and put your hands on my hips and try to kiss me.

“Chris, not so fast sweetie! Remember, I want to build up our relationship. This is about building something stronger. I don’t want you to just buy me something and get a quick bang out of it. That would make me feel cheap. But, I can see from your little hard on, you have needs to take care of. I’m not naïve =) And, as you remember from my profile, I’m a FREE spirit. So, if you don’t mind, why don’t you sit back and uh, just relieve yourself. Yeah, that’s right. You can do it in front me, I don’t mind. I’ll just keep trying on these clothes, take a few selfies, and drink my wine. Why are you hesitating? Don’t be shy. Whip out that big cock and jerk it for me. You can do it while I’m wearing this lingerie.”

After some convincing, you finally get undressed. You start playing with your cock while sitting on the chair across from me. “Sorry to giggle hun. I’m nervous too. I know it’s a little odd that I’m over here dressed, and you’re over there completely naked and jerking off. Lol. Well let’s just keep going and see how this plays out. Ooh, there you go, stroke it. I’ll go get you some lube.”

“Yeah, I see you going faster and faster. Come one. Oh Sweetie, don’t take this offensively, but are all Chinese as small as this? What do I mean?? Well, I’m used to seeing guys, white guys that are like 8-9 Tipobet inches. Yours looks a little on the smaller side. About 3-4 inches. Sorry, sweetie, didn’t mean to make fun of you. =) Just keep going. Cum for me. I’m sure you’re really good with that cock. Dick. Or whatever. I bet you really go the extra mile when you’re making love =) Just relax and keep going. I’m going to finish my wine and send out a few texts. Work it baby.”

“Ooh, looks like you’re about to cum. Do it! Wow! What a big load. Now, eat it, eat it. Eat it! It would really turn me on. Please? Don’t be silly, that doesn’t make you gay. You don’t realize this, but eating your own cum really turns a girl on =). I’ll help. Let me push your head down. Wow, that was hot! I’ve never seen a man eat his cum before. You really are opening my eyes up. I’m so glad we met. I bet with your experience, you can really teach me things. Ok, well, I have to meet up with some friends now. So, I’ll let you get some rest, after all this, uh, sex action =) I had a great first date! Hugs! See ya”

I take my shopping bags and leave. Over the next couple of weeks, we have a few more dates. I’m ecstatic as these dates go exactly the same. You bring over some fantastic gifts, outfits, shoes, etc. and you jerk your little dick off in front of me while I model the clothes. If you take a while, I just sit on the couch and text while you finish.

—————

“Sweetie, this is our 4th date. I just wanted to let you know how happy you’ve made me! And, from all that jerking and cumming I’ve seen you do, I think you’re having a great time too, right? I think it’s time we get a little more kinky, right? This time, I’m going to flash my tits while I model. And, I have a present for you! Remember at dinner, I told you about how I usually date white guys because they have these massive cocks. My friend Jake from the bar has a big one. I mean, he probably has a big one. I wouldn’t know =) Well, I want you to know what that really feels like. I bought this big dildo with suction cup on it. Baby, I want you to really turn me on and sit on it while you jerk off.

“Why the disappointed face?! What did you expect? I just thought this level of kink would really get me in the mood. I told you sweetie, we have to build our relationship up before I let you in this pussy. I promise, once you turn me on with all this kinky stuff, I’ll give you what you want. Now, lube up, and sit on this big dick. No one will know, it’s just us sweetie. You’ll be AMAZED how good it feels with a big cock in you. “

I flash you a little titty action, and you immediately lube up and sit on the cock.

“Chris, you little slut! =) I knew you could do it. Fuck your ass with that big cock! I know it’s big, you can hardly get it in. But trust me, it’s uh, really turning me on. Lol. Bounce on it faggot! I mean, sexy man. =) Just do it for me. Look, here’s another flash of my tits. Wow, you’re tiny cock is getting hard. Keep going, I’m going to try on more clothes.”

“I’m just taking a selfie of my new outfit. Don’t worry, you’re not in the photo (giggle). Keep fucking your ass. (while I keep fucking your wallet). Just kidding! There you go, look at all that cum that just squirted out. Come on, don’t lie. You loved that. Look how hard you came. No sweetie, this doesn’t make you a fag. This is something you do for your woman to make her turned on! Oh, don’t forget to slurp it up”

“Now, I brought you one more present before I go. See how nice Courtney can be?! It’s called a chastity device. It took a while to find an extra small one on Amazon, but I did it. I just want to be sure you’re mine and no one else’s. This relationship is going so well, I just want to make sure we’re true to each other… Look, if you’re going to complain maybe this is not the right fit for us then. If you want to keep going, then this is the deal. Wear it or else we can end the relationship. I mean, do you know how many messages I get on my website? You should feel really special that I chose you. Are you cool? Ok, that’s what I thought. Now, let me put this on. I swear Chris, we’ll get to where you want soon enough. This pussy is waiting for you, but all good things come to those who wait.”

“LOL. Look at your little dicky in that cage! So cute! Don’t you feel turned on, knowing that I’m the only one with the key?? You’re going to be extra turned on in between our dates. As soon as you arrive at our date with new presents, I’ll unlock the key. You’re going to associate spoiling me with presents with sexual gratification, and it’ll be so much more intense. Let’s take a selfie together. Come on, just for my own sake. You with your little dicklet in a cage, and me in the sexy outfit you got me. Smile!”

—————

Near the end of the month.

“Sweetie! Thanks for coming over. Did you bring your checkbook like I asked? Well, this is a special date. No presents or clothes needed. But, I did think you might want to help me out with these bills over here on the table. It’s end of the month and I have all my utilities, rent and credit card bills Tipobet Giriş due. I’m just a struggling student remember? And I need my sexy, sexy Chinaman to take care of me. I know we usually wait for the weekend so you can release yourself, but I’m going to let you do it early. Here’s the key hun, as soon as you write out all the checks for these bills, you can play with your little dick. I’m going to relax and drink some wine while you write out those checks, ok hun. Muah! Air kiss! =) “

“Thanks so much. I hope your hand is not too tired from writing all those checks, because you have some serious jerking to do! Lol. Look, I have your favorite, big fat cock over there in the corner of the room, all lubed up! Let me unlock you and you can have fun. Oh, I’m feeling bloated today, I don’t want to put on the lingerie. Here, I’ll pin up a picture of one of my selfies on the wall and you can look at it while you bounce and jerk. I’m going to the balcony to have a smoke. Have fun!!”

As you’re staring at my picture on the wall, I’m outside smoking and talking to one of my friends. You can barely hear, but you do make out a few works and sentences. In a soft voice you hear me say:

“hey lisa, my daddy is over again. Yeah, he’s off in the corner jerking himself. Just paid all my bills too. Little chinaman can’t stop touching himself. Lol. Oh hell no, we haven’t done anything yet. I know, easy right!? As soon as little Cha Ching! finishes, I’ll head over. Jake and his buddies are taking us out tonight…”

I open the sliding balcony window and check on you. “Chris, let me know when you’re finished ok? I have to meet up with Lisa later. Are you having fun by yourself? Lol. Ok, sweetie. Work it, and don’t forget to gobble up your cum after. Oh, Lisa says to bounce it baby! Just kidding, she doesn’t know. Lol”

—————

Another Date

“Chris, thanks for taking me to the spa today! I’m going to enjoy my 2 hr massage. And, I’ll be getting my nails and hair done too. You’re so sweet for waiting while I get all these things done. Imagine how sexy I’ll feel once I’m back at your place? The girls here in the salon think you’re such a hottie. None of their boyfriends would wait hours for them at a salon. But, that’s why you’re special! I’m sending them a few of my selfies with all the hot outfits you buy me. Don’t mind their giggles. They’re just jealous bitches. Although, I did show them a glimpse of your chastity device and they’re all so amazed I have that key right around my neck.”

Back at Chris’ place

“Well now, that’ was a fun date. Look at how relaxed I am after the spa. So, Daddy, one thing I haven’t shared with you yet is how turned I am with the BDSM world. I especially love spankings. Once I unlock your chastity device, let’s try it? Well, in this scenario, you have to obey me, no matter what I say, ok? We’ll start light. Just a few spanks on your ass. What are you waiting for? Baby, I can’t go over there and spank you. I just had my nails done. And with all the facial creams they put on me I don’t want to sweat it off. They were expensive! What do you mean it’s not the same if I don’t touch you. Ah, come on. I’ll be here to direct. Here’s a paddle I bought on your card.”

“Stop being a pussy. Now, give me 10 hard whacks. Count them out! 10, 9, 8, 7, 6, 5, 4, 3, 2, 1. Wow, you’re so good. Oh, I did mean 10 on each side. Now left cheek! And say “I’m Courtney’s bitch!” each time. This is hysterical. Let me call Lisa. She loves this shit. Wow, you’re dick went limp. Don’t puss out. Lisa is more dominant than me, she wants to watch and command while she’s on Facetime.”

“Lisa is on the line. She said she wants you to do TWENTY whacks. Either cheek is fine. But…after each one, yell out ‘I have a SMALL DICK!’ “

Courtney talks on the phone. “Dam Lisa, I didn’t know you roll like that. Ok, you heard her Chris. Look, if you keep hesitating, this is going to turn me off and you’ll never get this beautiful, AND BALD, white pussy. Are you going to turn me on or what? I get off knowing you’ll do anything for me, ok Daddy? Let’s go, bitch!”

You start spanking your ass. We stop you to remind you that you have to yell out the phrase. “Start all over! Ok, 20, 19, 18, 17, Louder!. 16, 15, 14. Say it like you mean it. 13, 12, 11, 10, 9 8 7 oh, Lisa is pleased…6, 5, 4, 3, 2, 1. Yeah!”

Suddenly, you hear a muffled sound outside, like some neighbor yelling. You’re mortified. “Sounds like a neighbor just yelled ‘shut up!’. Lol. I hope they didn’t hear =) Ah fuck him, some old loser next door. Let’s keep playing. Lisa, are you touching yourself over there? Yah. She’s getting really hot watching all of this. Make Lisa cum on the other side of the phone ok?.”

“Ok, once more, and this is a fuck you to that neighbor. Come over away from that corner. Kneel right here. Fucking bitch, right here!! In front of the balcony window. I know, intense right? Anyone could walk by and see you. Time to do 20 more. This is how I know you’re my daddy and will do whatever I ask ok? 20 more, and each time, YELL OUT “I’m Chris, Tipobet Güncel Giriş and I’m a small dick bitch!” Yeah, of course you have to say your fucking name. That makes it fun. Don’t freak out, no one will really hear.”

“Ready, 20, 19, 18. 17, 16, 15 Wow, you’re really yelling it. Stop for a sec. Fuck, it’s hot in here. Better open the sliding window. Lol. Don’t bitch out on me, or I’ll leave and not call you ever again. Ready, start again. 20, 19, 18…3, 2, 1”

Lisa can be heard laughing her ass off each time she hears “I’m chris and I’m a small dick bitch”. But, she’s not happy. It’s hard to hear on her end. But, truthfully, she could even hear some neighbors in the background. You’re shaking on your knees feeling so vulnerable.

“Chris…START OVER. Lisa can’t hear. I know you feel so exposed with your window open. I think I even sense neighbors starting to open their windows to see what is going on. Oh well, you have to do this. 20 good ones spanks, and no mumbling your catchphrase. Go! 20 19 18 17 16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1. You’re face is so beat read. Take a breather but stay right there in front of the window.

“Ok, catch your breath? Stand up, get closer to the window. Now, 10 hard whacks, and say “I’m Chris, and I like big cock up the ass!” You HAVE to do this, just to show you love me, ok? Don’t fuck with me Chris. Now get going. 10 9 8 7 6 5 4 3 2 1. Wow!”

You spank your ass beat red. And your face is even redder knowing that people in your neighborhood probably heard that. From now on, you better walk outside with a hat and shades on. I start to put your chastity device back on, and that’s when you realize that you already came. With the beating you gave yourself, you didn’t even notice shooting your load. While you’re cleaning up, you hear me and Lisa talking on the phone.

“Wow, that was incredible. You see all that Lisa? Yeah, of course my nails are in tact. I didn’t even touch him. Girl, you’re just as much of a biatch as I am so don’t hate. Love ya. See you later.”

—————

Next week, I call you up for a special date.

“Chris, I want tonight to be really special. Let’s go to the jewelry store at the mall before dinner. I want to you to get me that necklace and matching ring that I’ve been eyeing for a long time. And for my special, sexy man, I want to do something tonight to make you REALLY turned on, ok? I’m so HAPPY to have met you Chris. Let’s go crazy on the town tonight.

At the jewelry store, I’m trying on the necklace and ring. “Look how beautiful I look with this on? Stop staring at the price tag Chris. I know it’s a few G’s. You’re a Director at your company, right? Ok, I know it’s a lot. But if it hurts your wallet, that’s how I know you really love me. You can do it for your beautiful baby, right? Don’t be embarrassed in front of the sales lady. She’s my friend. She knows ALL about my special daddy, right Lisa? She’s giggling out of jealousy. She was the one on facetime the other night =) ”

I take the chastity key hanging around my neck and dangle it off my pinky finger right in front of you. “Chris, see this key? It’s all that stands between you and an awesome time tonight!” I start to stroke my pinky finger up and down, and Lisa and several of the staff there start to laugh. You finally pay and even have to use two different cards to buy the jewelry. While you’re paying, I’m sending out a text. Lisa and another lady at the store get a chime on their phone. As they look at their text, they bust out laughing. I flash my phone at you and you look in horror as you see a pic of yourself straddling on a big dildo and playing with yourself.

“Look hun, no one else except Lisa knows. And I guess her coworker too. Lol. I don’t really know that bitch. But don’t worry, they won’t spread that pic around as long as I’m happy. Ok hun? Look, here’s another pic of you licking up your cum. Watch as I send it to Lisa and her friend. Shush, don’t talk back to me. Watch. Here we go. Send! Lol. They’re laughing hysterically. Don’t worry, with that fat commission she just got, she’ll shut up. Let’s go home.”

Back at home

“Don’t I look beautiful with my new jewelry on Chris? Of course I do =) Let’s have a drink. I want you really drunk for my surprise gift for you. I want you to have an incredible orgasm tonight, and what better way than to see me naked and fucking, right? “

“Oh, there’s a knock on the door. Go see who it is… Hi Jake, come on in! This is my Chinese sugar daddy that I’ve been telling you about. Chris, remember him from the bar? That nice handsome tall man? I told you he was going to get me a job. Sorry, that was a little white lie. Really, I just saw this hot guy and wanted to fuck him. So I got his number that night. We’ve been fucking ever since, along with some of his friends. This is the real world hun. A beautiful girl like me needs a monster cock to feel good. But, I still love you baby. You’re my world. I just love spending time with you, and spending your money. But that little pee pee locked in that cage is not going to do it for me. You still get to be with a beautiful young woman like me, to spend your money on and be close to me. You’ve even seen me half naked from time to time so you can get off to. Isn’t that a great arrangement? Look with that little dick, you’re lucky to have this nice thing we’ve got going on here, ok?”

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