Sugar Daddy Pt. 02

Daddy pulled his underwear and pants back up, refastening them. He held out his arms to me and I went to him. He hugged me tightly to him, kissed me tenderly, and turned to leave. "Thank you, Margeaux. I know I'll sleep like a baby tonight. I'll be dreaming of you."

I smiled at him with longing in my eyes but as soon as he left, I sighed deeply. I began to compile a list of 'pluses and minuses' in my mind about my relationship with Daddy. I knew this had nothing to do with how Daddy had presented himself from the beginning, what he was willing to provide to me, and what his expectations of me were. I had come to realize just how lonely being a mistress could be sometimes.

I looked at myself in the mirror. I had spent hours and hours trying to make myself as beautiful, sexy, and desirable as I could. My old male self would have killed to be with a woman like me. And yet despite looking like one of the hottest women in Monte Carlo, here I was, all alone.

I liked sex. No, I loved sex. I resolved to at least broach the conversation with Daddy about pursuing other relationships outside of ours. He was very much the businessman; he couldn't have become so successful without thinking like one. I wasn't going to be asking for anything other than to enjoy myself when I wasn't with him.

The next night, we were lying in bed together after a wonderful evening of sex. I was in Daddy's arms, and he was stroking me tenderly. Running the fingers of one hand gently through my hair, teasing my back lovingly with the fingers of his other hand.

"Daddy?"

"Yes, Margeaux?"

"I'm not sure how to say this or where to begin. I don't want you to think I'm ungrateful or that I don't enjoy being with you or coming to all these fabulous places you take me. But...."

"But you want to know if you can see other men. You're hoping I don't view our relationship as exclusive despite the fact that I am very much a married man."

"H-ho-how did you know that's what I was going to ask?"

"Margeaux my dear, you don't get to be as successful as I am without being able to 'read' the people you are in business relationships with."

I winced when he said that. "I'm not trying to hurt you by saying that my dear. But let's be honest. From the beginning, our relationship has never been based on romantic love. You enjoy all those things I provide that make it even easier for you to BE Margeaux. I enjoy all those things that Margeaux does for me that my wife is no longer willing to provide."

I nodded in agreement. It was hard for me to argue with what Daddy was saying.

"Quite frankly, I'm surprised it has taken you so long to ask this of me. By the way, Christopher told me you tried to take him into your bed early in our relationship. I certainly admire your taste in men. Not only is he a man of impeccable character; he is a 'hunk' as you young people say."

I blushed deeply. I shouldn't have been so surprised that Christopher had told Daddy about my advances toward him. As Daddy said, Christopher is a man of impeccable character.

"So yes, I have no problem with you being with other men as long as you are willing to meet my requirements about such relationships."

I raised an eyebrow, sucked in my lower lip, and nodded for Daddy to continue.

"Number 1 -- Our relationship still takes precedence over any other relationships you might develop. If I want you to be somewhere with me, you will agree to do so even if you have already made plans with some other man. Of course, in return, I will do everything in my power to give you as much advance notice of my requirements as possible.

Number 2 -- Our relationship must remain a complete secret. You may not, you cannot, tell anyone about me.

Number 3 -- If you do have a liaison in between meetings with me, you must get a complete physical before we get together again. I cannot afford to contract an STD when my wife no longer sleeps with me.

Number 4 -- I expect you to be just as careful in establishing any other relationships as you were in establishing ours. No one-night stands, no friends-with-benefits, no group sex; in short, any other relationships you might develop will be just as well thought out as ours has been.

Number 5 -- Your femme name and image may not pop up on social media anywhere. I know that your male persona has some social media accounts; Margeaux O'Grady does not. It must stay that way.

If you think you can adhere to all these requirements, then you are more than free to seek out other relationships with my blessing. If there is anything you don't feel you can agree to, if there is anything you are unwilling to agree to, then we need to end our relationship. You can keep everything I've given to you, but of course your credit card will be canceled."

It didn't take me long to decide. Daddy was being more than fair. He wasn't asking for anything more than a man in his position would ask for. He was giving me his blessing, with certain limitations, to be with other men. That was what I had wanted and quite frankly, the conditions he was insisting upon were probably just as good for me as they were for him.

I rolled him on his back and straddled him as I guided him inside me again, and said, "I agree completely. Let's not just seal this with a kiss though."

He pulled me on top of him, rubbing my nylon-clad thighs. He placed the other hand behind my head and pulled my face towards his. I threw my arms around his neck and began to kiss him passionately. He sucked my tongue into his mouth and began to rub my ass cheeks as well. I was in heat!

"Daddy, Daddy, oh Daddy, yes, baby yes. You are so hot; you're turning me on so much. Take me, make me yours again. Make love to me all night long. Please Daddy, please. I want your cock so badly; I need to have your cock inside me." I reached underneath me to rub Daddy's cock; he was erect and throbbing again.

I straddled his legs facing him and reaching underneath me, I guided him to my rosebud and sat down on his hard cock, engulfing it all the way down to his balls.

Daddy groaned. I just sat there, smiling at him. I was squeezing his cock with my ass muscles but that was it. I wasn't moving at all, just milking him with my educated ass. He started begging me, "Margeaux, this is so fucking hot. Please ride my cock baby, please fuck me with that hot ass of yours."

I began to rotate my hips, first in one direction, then the other all the while squeezing him, but I did not ride him up and down. "M-Mar-Margeaux please, PLEASE fuck me, please!" I smiled at him again, but again, did not ride up and down his shaft. "Oooooohhhhhh, Margeaux, shit, shit, shit! Fuck me baby, please fuck me. Ride this cock, ride this cock, ride this cock. Fuck meeeeeeee!!" I could feel Daddy begin to throb and tremble inside me, now was the time.

Still squeezing, still rotating, I began to slide up and down the length of Daddy's shaft. Slowly at first, very slowly, I wanted to feel every inch of him going in and out of me. I would lift my hips until just his prick was inside me, then slide back down until my ass cheeks were resting on his thighs. "That feels so fucking incredible. I love this pussy, Margeaux. So tight, so good. Mmmmm, damn, damn, damn. Fuck me, baby. This cock is yours. Take it, Margeaux, TAKE IT!"

Daddy was shivering underneath me; I knew he was close. I began to pick up speed, riding his cock faster and faster. Soon I was gliding up and down his shaft, he was stroking my nylon thighs firmly. This sent me into a frenzy, and I started humping him furiously. We came simultaneously. Moaning, groaning, screaming, swearing, we continued to fuck each other through our orgasms. Finally, both spent, I collapsed against Daddy's chest.

He was holding me close to him, kissing my hair, stroking my back and ass. "No one has ever made me feel the way you do, Margeaux. You are so hot, so sexy, so loving."

When we got back to the States, I began to search dating sites on the web for that perfect someone. I was now in my late 20's. I began to narrow my search to only include younger men. Daddy was the older man in my life; I thought it might be fun, exciting and erotic to be a MILF.

I took my time. I was in no hurry. I wanted this new relationship to be every bit as successful as my relationship with Daddy. I chatted with a few guys for a while, but nothing ever came of it. Most of them were too impatient and didn't want to spend any time getting to know one another. They just wanted to fuck and fuck now! The others weren't interested in a MILF. The fact that I was going to be turning 30 wasn't something that turned them on in the least.

Then I met Nicholas. He had just turned 19. He was the youngest child in his family; he had two older sisters. His father divorced his mother shortly after he was born. He was raised in a household with no masculine influence around. His mother and sisters were very old-fashioned in the way they dressed. They rarely wore pants. Even at home they always wore makeup.

When Nicholas began to try the dating scene, he looked for a woman who had those same qualities as his mother and sisters. The majority of modern women just weren't into the style Nicholas preferred to see a woman wearing. That led him to pornography and masturbation. As he looked at porn online, he discovered crossdressers and became enamored of their ability to present themselves as beautiful women, the kind of woman he had long fantasized about dating. That led him to dating websites; he found one where I just happened to have a profile. He reached out to me.

"Your profile said you were looking for a younger man; I hope I'm not too young for you. I'm really new at this; I've never been with a woman like you before. I hope I'm not too inexperienced for you either. I just think you're beautiful. I hope you'll be willing to take the time to let me get to know you and for you to get to know me. I'm extremely nervous; I'm sure I don't come across as suave and polished as other men. But I'm genuine and I don't play games. I hope to hear back from you soon."

Nicholas was exactly the kind of man I was looking to meet. I replied, thanking him for his interest in me and his honesty. We began to email one another sharing more of our life stories. He was cute and caring in a way that Daddy wasn't. I was grateful to Daddy for everything he'd ever done for me; he'd allowed Margeaux to blossom in ways she never would have had the chance to do without his help. But at the end of the day while our relationship was very enjoyable, it was also very much a business one. And Daddy was in complete control of that relationship.

Eventually, Nicholas and I exchanged phone numbers. I purchased a burner phone for the express purpose of communicating with Nicholas only. He began texting me daily, but he would only call if he received permission from me. He never cold-called me. He definitely sounded much younger than me, which he was, but he had a gentle, soothing voice. We finally decided to meet in person to see if the electronic sparks we felt from our emails, texting, and calls would continue face-to-face.

We arranged to meet at a local coffee shop, late one morning. I decided to dress down somewhat but still wanted to go for that feminine look I know Nicholas adored. I chose a beige, knee-length gauzy wrap skirt and paired that with an off the shoulder flower print blouse that tied in front. Underneath I wore a strapless beige body briefer with thigh high, lace top, suntan stockings. I chose cream-colored strappy sandals with 3" stiletto heels. My makeup palette complemented the flower print from my blouse.

One last look in the full-length mirror on the door of my bathroom and I felt ready to go. I was nervous, but hopeful Nicholas would continue to like what he saw in my pictures once he got a chance to see me in person. There was a knock at my door. Looking out the security peephole, I saw Christopher standing there. I was stunned to say the least.

"Christopher, what brings you here? Please don't misunderstand what I'm saying but please don't tell me you're here to let me know Daddy wants to see me."

Christopher smiled. "You look very lovely, Margeaux. Even dressed casually, you're as beautiful as any woman I've ever met."

I smiled back. Personal compliments from Christopher were rare. He handed me a manilla envelope. "What's this?"

"Mr. Smith knows you don't have the same resources he does. In his own way, he does care about you. This is a background check of the young man you've been communicating with. Hopefully it aligns with everything he's told you or will tell you. Mr. Smith said he hopes you will look upon it as a sign he really does care for you and not as an invasion of privacy. Have fun today. I hope your date with your young man is everything you're hoping it will be."

Christopher turned to go. "Thank you. Please tell Daddy I AM appreciative of this gesture. It is very kind and caring of him." Christopher paused and looked at me again. Really looked at me. Sighing, he turned and left.

I went back inside and before I opened the envelope, I texted Nicholas to let him know I was running a few minutes late. All of the background information matched up with what Nicholas had told me. In addition, there were some things he hadn't told me but weren't over-the-top relationship killers.

Nicholas was a college sophomore. He was only 5' 8" tall but weighed 175 pounds. He was a member of his college's gymnastics team; his specialty was the rings. He was majoring in Economics and had been on the Dean's List ever since he started school.

I hurried to my car and drove to the coffee shop where Nicholas was already waiting. I was seven minutes late. I recognized him from the photos he had shared, he was even more handsome in person. He stood to greet me; I was definitely a few inches taller than him in my heels. It didn't bother me; I hoped it wouldn't bother him.

He held out his hands to me, I put my hands in his. We kissed each other on both cheeks, European style. "Nicholas, I am SO sorry for being late, especially the first time we're meeting in person. I pride myself on my punctuality. Just as I was leaving, a delivery man brought a package for me. I had to sign for it and take it inside my place before I left."

"Please don't apologize, Margeaux. I understand completely. Besides, a beautiful woman like you is more than worth the wait."

I leaned down and gently brushed his lips with mine. "Thank you. You are a true gentleman in every sense of the word."

He pulled out my chair and seated me. Definitely old-fashioned but I loved being treated like a lady. The waiter came and took our orders. We made small talk until our coffee and pastry arrived.