Confessions of a Sugar Baby

Story Info
I need to finally get some of my history out.
9k words
4.87
7.1k
11
Story does not have any tags

Part 1 of the 2 part series

Updated 06/11/2023
Created 11/20/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Where do I begin telling you my story? I'm not going to start back at the beginning because my current situation is way more interesting. I might tell you the beginning part of the story another day but let's focus on the recent.

Much of what I'm writing about is true and how it happened to the best of my memory so that is a different spin than most things you read here. I need to get it out, and you'll understand why I can't really tell anyone, so I am putting it here for you all to read.

First, I had a great childhood. My parents loved my younger sister and I and always made sure we knew it. They put us in all kinds of activities and were always on the sideline or window cheering us on. Everything from Dance to Gymnastics to Hockey to Soccer, we did it all. I don't have daddy or mommy issues.

When I was a freshman at college someone ran a red light as my family was headed one of my sister's softball games and I was suddenly all alone. It totally crushed me and changed my view on having a family. I never wanted to have a child go through what I was going through.

The accident had another impact though, I was no longer anchored to Ohio. Truth be told I couldn't get out of Ohio fast enough. There were too many memories, so I arranged with a fiduciary to take care of selling my parent's home and rental property and put all my earthly possessions in a van and got on the road. When I got to the 70 I flipped a coin and then turned west and just kept driving.

I was angry, and I knew it, but driving was something that I always found to comfort me so I just kept driving. I had no destination in mind, I was leaving mid January and just drove. The 70 turned into the 44 which turned into the 40 and I just kept driving.

The next thing I knew I sitting on the beach in Santa Monica crying. I cried until I couldn't cry anymore. I contemplated many things that someone shouldn't, but my parents always drilled into us life is for living and no matter what happens, when life knocks you down, you get up. Period. You always get up. So I did, I got up, wiped my tears and took my first breath in weeks.

I lived in Santa Monica for a few months but moved down to Orange County when I was accepted as a transfer to UCI. I had a monthly stipend, plus the proceeds from the sale of the houses to make sure I was covered. The fiduciary were smart and implied I had to talk to a financial planner before I would be able to get the money, so I wouldn't be spending it all like a regular 19 year old, so I was set up for several decades.

I bought a small house in Newport Beach on the non-beach side of PCH and focused on school.

At that time I had just turned 20, I was 5 foot 3, 100 pounds, C cup round full breasts with a cross between a hourglass and rectangle body. I was skinny and a little thin, but after what I had gone through, people either loose or gain weight. That said, I looked great in a bikini and I spent a lot of time at the beach.

The first time I realized that my morals were not what most people considered normal was when I had a fight with a girl in university. She was a typical stuck up California future real house wives type of person. Apparently I had parked in "her spot" in the garage and she made my life hell for a week, so I slept with her boyfriend, took pictures and sent them to her. It was easy and I loved the power. I felt no regret, in fact I loved it.

The power high was intoxicating. It was a drug fix. I'm mature enough now to know it. From then on, for about a year, if you rubbed me the wrong way, I slept with the person closest to you. I didn't care if it was your husband, your boyfriend or brother, I slept with them a few times and made sure you knew about it.

The stories from that part of my life make me laugh in retrospect, but those are stories for another day.

When I was in my Jr year a set of things happened and I ended up with my first sugar daddy. I was 22 at the time and it just happened. He was 40, had made millions in tech and was doing what he wanted. Yes he was married with kids but I really didn't care. It was a thrill knowing someone was risking everything they held special to be with me. I also wanted clothing and to be treated and he wanted to think he was doing something wrong. It lasted for about a year and half until his wife hired a private investigator to follow him. Of course he got pictures of us in all kinds of positions and situations, his wife left him and his life spiraled and I exited stage left.

Over the next decade and a bit I had 3 other sugar daddies. When I was 28 my sugar daddy wanted me to go through breast augmentation and paid for a top of the line under tissue procedure that brought me up to a 34 DDD and they look and feel fantastic.

Even as a female I know that I have what most people think of as the perfect body now. I work hard for it to stay this way but I do. I now weigh 115, I have a nice tight back side, I have abs but not that sick looking too thin look. My legs look great either in heels or barefoot. I have shoulder blade length straight dark hair with blonde highlights. I'm 34 and well established and secure. My house is now paid off, I drive a Mercedes and am doing well. I sell real estate to the mid level crowd and yes will do whatever it takes to get the sale. Again more stories there.

That brings me to where we are now, mid July 2021. Yes the second year of COVID, but this is Orange County and people are done with COVID and masks. I'm sitting at the bar at Billy's at the Beach waiting for him.

Mike is the guy I'm waiting for. He is the owner of 8 wellness centers between here and Austin. He took the company over from his father with 1 office and has grown it big time. He spends 2 days here a week and broke up with his last sugar baby Amber 2 weeks ago. She and I are acquaintances. When you are a sugar baby long enough, you meet others that are in the same situation. I knew of Mike, his tastes, his kinks, his back story, what he didn't like and what made you fall out of grace, but most of all, he didn't know me.

There are rules that you need to be aware of becoming a sugar baby. They are pretty simple, the answer is always yes, never question or ask a personal question, act without hesitation, know your place, and never ever get attached and make a scene. When he tells you it's over, and it can come at any time without notice, you smile, show no emotion, and walk away head held high.

The attachment part is hard for a lot of women and that is generally the straw that breaks the back. I have never had that problem, usually the guy becomes attached to me or he gets sloppy and his wife finds out.

Mike doesn't know that I have been waiting for him, he has no idea how much I know about him or he is very much going to the hunted tonight. He is usually the hunter, but tonight he is pretty much already done like dinner. I want to hook him and I have everything planned. I have prepped for 2 weeks for this moment.

I know every Tuesday around 5:45 he takes a Duffy across the channel in Newport Harbor, comes in for drink and maybe a light meal and then goes and tours around the water. He then usually spend the night on his 55 foot yacht or goes back to his condo at 611 Lido park. He sits at one of two spots at the bar every week. He used to be here with Amber but last week he came solo and left quickly after just a single drink.

He is a good looking guy but not over the top wow type. He is fairly fit for his age but it's aura that I am always drawn to. Amber said he was had a nice size package of around 7.5 inches and a good girth.

I'm sitting at the bar wearing one of my favorite outfits. A choker around my neck, a black Deep Cowl Neck Party Dress made by Mapale and a pair Christian Louboutin Suola Loubi heals. My chest looks amazing and of course I don't have a bra or panties on.

I can see him getting close in the Duffy and I get myself ready. A Duffy is an electric boat that is quite popular in the Newport Beach Area. They are anywhere between 16 and 21 feet long and great for just putting around. They are usually full with people having a bottle of wine or two.

He docks his Duffy at the dock and walks up the ramp to the bar. I pretend to pay no attention to him for about 15-20 minutes. I have another drink and pretend to look at my watch as though I'm waiting for someone. He is looking at me ready to pounce and I chuckle to myself thinking if he only knew.

I pretend to lose patience with the person I'm supposed to be waiting for and pay my tab and start to walk away smiling politely at people.

When I get to him he says "Don't leave so soon, the night is just starting."

I give him a mock laugh and say "I bet you say that to all the ladies, I was supposed to meet someone and he has stood me up. I got all dressed up and took an uber here just to be stood up."

"Join me for a drink then, I'm here solo and some non-pressure conversation is maybe what we both need." He says pointing to the seat beside him.

When I hesitate he extends his hand "I'm Mike, and it's just a drink and maybe some food by the water."

I mentally wait just a second so I don't look too eager and then shake his hand "Hi Mike, I'm Veronica or Vicky for short, it's nice to meet you." And sit down.

"Mai Tai's?" he asks lifting his glass.

"Most certainly." I say

He orders the drinks and turns and smiles and is about to open his mouth to say something when I cut him off.

"Don't try to boast, just talk. We can tell we both do well enough to be here, just know you will do better without the bravo."

This actually makes him laugh hard and genuinely.

"Noted, and thank you. I don't get to laugh much. Tell me, what happens if the person you were waiting for shows up?"

I can see him stealing glances at my chest and I smile at the thought of when I get to watch his face when he sees me naked.

"He won't show up, his family is keeping him occupied, which is too bad from him."

This catches him by surprise and his face shows it.

"His family?" he says without realizing.

This is almost too easy I am thinking but I keep the charade going.

I roll my eyes, smile, lean in towards him and almost whisper "Ok, I know it's considered wrong, but it's always been one of my kinks. I love being a sugar baby. I was meeting him for the first time tonight and I think he chickened out." I say and then sit back and have a drink.

I catch my breath and let that last part sink in and then add "I don't need to be one, but I get off on it. Anyway who are you and remember, don't boast."

Mike laughes again.

"This is easy, my name is Mike, I'm the oldest of 3, I'm in health care, and I'm here a couple of days a week. That is me without any boasting"

"That is very refreshing, thank you Mike. Do you surf?"

And with that simple question we start an hour long chat that has no boasting and just going back and forth about fun stuff and it one of the easiest conversations I have had in a long time. I catch him looking me up and down and trying to steal glances when my breasts move but for the most part he keeps eye contact. He is totally disarmed and ready to be taken.

"You have been mostly good about not staring but if you want a look say you want a look."

"I want a look." He says with half a laugh-half challenge to see if I would do it.

Without hesitating I turn to the side so he gets a good profile side and slide my left hand between the fabric of the dress and my breast and pull it forward so he gets a good look and then turn back to him smiling.

"You act like you have been a sugar daddy before."

"I have."

"How do you like it?"

"It depends, OC girls rubbed me wrong lately."

"I'm from Ohio." I say smiling

He laughes again.

"You do make me laugh. It's refreshing." And then his eyes focus on me and he goes rapid fire "Ok, let's see if you are different. Anything I say, when I say, how I say, safe word allowed but the day you say no, is the day it's over."

"Agreed, no abuse, no violence." I counter.

"Agreed, no limits though, any kink allowed."

"I'm sure my list of kinks is longer than yours" I say challenging him.

"Swallow."

"Eagerly"

"Anal"

"Happily, I have explosive orgasms that way"

"Facial"

"Yes even in public"

"Multi people"

"In any combination"

"Birth control"

"IUD, no desire for kids"

"PDA?"

"Whatever you want"

"Are you an escort or pro?"

"Never have and no. I like being a sugar baby, I like belonging to only 1 person."

He pauses and I know I have him.

"What's in it for me?" I ask

"What is your expectation?"

"Allowance, treats, surprises, 7 a month would be a start."

"No Drama, ever" He says without hesitation at my last statement.

"Never, same goes for you though, no family drama" I say.

"If I tell you to go and make out with a woman, what will you do."

"Without hesitation."

"The one at the table by the rail. Pink outfit." He says with a nod of his head indicating a table behind me.

I know this is a challenge, he did the same thing to Amber so I knew it was coming.

Without any hesitation I slide off the stool and turn and walk to her. She sees me coming and involuntary looks me up and down and smiles at me. I walk straight to her lean down and plant a deep kiss on her lips. She resists at first and then her tongue reaches for mine.

When I break the kiss she catches her breath and says "Never had that done to me before. Thank you"

"No, thank you I say." Before turning and walking back to Mike.

"That was well done." Mike says

"Thank you sir." I say submitting to him

"Are you a sub?"

"I am everything sir. I will be a sub, I will dom, anything, anywhere, anytime. If you want anything from me, take it, or tell me. But yes, submitting is natural."

When I was passing the test he moved our chairs closer together and now our legs are between each others.

"Is that a yes, sir"

"Yes." And with that he slides his free hand on my inner thigh sending bolts through my body.

"Well this evening has turned out way better than I hoped." I say while opening my purse.

"The guy I was supposed to meet had me bring these."

Mike looks inside and sees the toys that I brought to give me an idea of my kink side. He pulls out the crystal topped stainless steel anal plug and smiles. I slide forward until I'm on the edge of my stool.

"I was told to bring these and a good sugar baby does what she is told."

"Block him and never talk to him." Mike says very authoritative.

I smile "Happily sir" and block a number for a fake account I had created.

"Do you enjoy having this in?" he asks hold the plug in his hand.

"Honestly yes, it's naughty and it's private, I love having it in at the beach." I say

He leans in towards me to close the gap and comes up to my ear, but what he has really done was conceal his right hand as he slides up my skirt.

I feel the plug inch its way up my thigh.

"Are you going to take me bare?"

"Yes"

He has it against me, spinning it and lubing it.

"Are you clean?"

"Yes, I assume you are as well."

"Yes"

"Do you know anyone here?"

"I don't care and wouldn't stop you." I say and then add "A little bit further back"

He pushes is hand further until the plug is against its entry.

"Right there, now push it in."

He does as instructed and my body eagerly takes the toy and then he pulls his hand back to my thigh. Little does he know I have spent the entire day with a larger one in and took it out only 30 minutes before I got here. My eyes always roll back when I'm first entered and I come back to him and smile.

"I hope you'll be sliding something else in there."

"Let's head out" he says standing and leaving a $100 bill on the bar for the bartender.

"Are you ok to walk with it in."

"Oh yes, I'll go all day with it in without any issue."

He takes my arm and we walk to the dock and his Duffy.

Mike helps into the boat and points to the bow of the boat where the dock lines are as he gets in and turns the batteries on.

I bend over to grab the lines from the dock hand knowing full well that my skirt has hiked up and gives Mike a prefect view of the crystal plug. I take the heels off and walk seductively back to him as he pulls the boat out of the docks and into the main channel and heads south.

I grab the bottle of wine and 2 glasses and pour us a couple of drinks before sitting down in seat beside him.

"To something new." I say raising my glass to him

"To something new." He echoes me.

We have pulled away from the edge and are now in the middle of the channel and I turn on the seat to face him. He hands me his glass of wine and then slides his hand finally against my breast and grazes my nipple.

The moan escapes my mouth is one of utter relief. One that I hope to have several more times tonight.

"I hope you are good for a few rounds tonight." I say biting my lip.

"I took a red pill before I left, so multiple rounds are expected." He says as he continues to stroke my nipple which is making more wet by the second.

"Can I go down on you here or is it too public?"

He finally leans forward and kisses my lips

"I was just about to tell you the same thing, but be quiet as I call home."

I know this is a test and I know he has a family back home, but to be honest I don't care because I know I'll be getting what I want. I take a pillow and lay it on the deck and kneel down on it smiling up at Mike. This position is such a power rush for me. It drives me wild knowing that I can basically ask for anything I want at this point and every guy will say yes.

I undo his belt, and bite my lip as I undo his button and pull down his zipper and reach into his boxers to pull his cock out. Amber was right, it's a nice remote, shaved smooth and clean. This is the way like it. All men should shave or trim their cock in my mind.

I smile up at him and make no pretense of being slow, I engulf it in one shot. This is when I start to embrace my inner slut and just the power I have.

I look up at him as he is taking my picture. I know he likes taking pictures and I smile up at him with his cock in my mouth. I focus back down on my task at hand and hear the phone dialing. To my surprise he video chats with his family at home while both driving the boat and having his pole smoked. Maybe men can do more than one thing at a time. I think about it, and it makes sense. A wife can't argue when you get to see his face every day.

I slowly keep working his cock for 20 minutes as he wraps up his call with his family and I'm more turned on than usual knowing the power that I have.

With his call over I focus on finishing him off. I wrap my hand around his cock and put it against my lips and then twist on every stroke. He doesn't last 30 strokes before he puts his hands on the back of my head and drives his cock down my throat and unleashes himself. I put my tongue on the bottom of his cock and feel his vein pulse as stream after stream are pumped directly in tummy.

I wait for him to finish before releasing him from my mouth.

He recorded the whole thing and still is so I look up, smile and say to the camera "Thank you daddy."

I take back my glass of wine back and have a sip to clean out my mouth but remain kneeling in case he wants me start again.

"Come sit up here with me."

It's close to 8pm and we still have about an hour before the sun sets. We have looped around the harbor and have finished the bottle of wine. Our conversation has been fun and light and he has seemed to be finally very relaxed.

We pull up to the shared dock behind his condo building and he ties up the Duffy and plugs it in to be charged overnight. He extends his hand to me to help me out of boat. He guides me to the back entrance of the condo and he pushes the button for the elevator.