Sugar Daddy

I had just gotten out of a luxuriating bath. The water was so hot my skin had turned pink. The scent of the musk bubble bomb still lingered on my skin. As I rolled the 15-denier, jet black Cervin stockings up my hairless legs (thanks to the electrolysis treatments), I thought back to how I had gotten to this point in my life.

I guess it started when I had to stand-in as a 'mannequin' for my sister. She was a year older than me and had been asked to be the flower girl for a cousin's wedding. The cousin lived out of state. My sister did not travel well and became violently ill during the trip. We arrived two days before the wedding. My sister was supposed to go for her final fitting for her flower girl dress but wasn't even close enough to being well to be up for it.

My mother had the brilliant idea I could stand in for my sister at her fitting. We were almost identical in size at that time in our lives and there weren't a whole lot of options. My mother started having second thoughts when the seamstress insisted I wear girl's panties, a camisole and tights during the fitting. The seamstress was adamant her fittings worked best when they included the undergarments the person would be wearing.

My mother relented, my sister's dress fit perfectly at the wedding, and we went on with our lives. That incident didn't really affect me much, I was more curious about how many clothes girls wore underneath their outer garments than anything else.

They say history repeats itself. It happened again. My sister had been chosen to be a junior bridesmaid for another cousin's wedding. Of course, she got sick during our travels and was bedridden when we arrived. This time my mother told me she would pay me if I would be willing to stand in again for my sister for her bridesmaid dress fitting. I was only an inch taller and five pounds heavier than my sister; this seamstress agreed that shouldn't make that much of a difference.

The difference for me was in the undergarments. I had to wear satin panties, a matching satin bra that the seamstress stuffed to mimic my sister's chest measurements, and a satin garter belt and stockings. Puberty had hit by now and I was overwhelmed by the feelings of the materials against my skin. I had never, ever felt anything like this before. The seamstress was kind enough not to mention my erection and managed to finish the fitting around it.

Those were the only two times in my life I had ever dressed in girl's clothing. The first time resulted in more of a curiosity, the second time turned into an obsession. I never got another chance to dress in women's clothes until after I had graduated from college and got my own apartment.

I should mention I'm the same height as the average American male, 5' 9" tall. I'm well under the average weight checking in at only 155 pounds. I dated off and on during high school and college; I lost my virginity and enjoyed sex with women but there always seemed to be something missing. I tried to get my girlfriends to dress more 'feminine' and sexier, but they always seemed to feel I was denigrating them. Even when I bought the clothing and gave it to them as a present, they would never try them on or wear them for me.

My last girlfriend got mad, not just mad but angry because she felt I was insulting her! She threw the lingerie outfit, stockings and heels at me as she stormed out of my apartment. I was stunned to say the least and more than a little depressed. As I sat around moping, I remembered how I felt when I wore the undergarments and stood-in for my sister's junior bridesmaid fitting.

My girlfriend and I were similar in height and weight. Trembling, I stripped out of my male clothing and began to try on the lingerie, stockings and heels I had bought for her. My cock was rock hard and throbbing long before I finished getting dressed. I stuffed some cotton balls into the cups of the bra to fill it out. I stumbled around in the 3" stiletto heels but managed to get my balance and walk over to the full-length mirror.

I gasped as I looked at the feminine figure in the mirror. From the neck down was a woman I'd want to fuck all night long! I laid down on the carpet in front of the mirror and began to rub my 'clit' through the satin panties. It didn't take long, and I had the most violent, most intense orgasm of my life. Cum oozed through the panties and onto my hand. I watched in the mirror as this sexily clad 'woman' eagerly licked the cum from her fingers. I was hooked from that point on.

Luckily, I had gotten a job as a financial analyst that allowed remote working. I rarely had to go into the office. I allowed my hair to grow out; long hair on a man was nothing out of the ordinary. I got my ears pierced; again, that was nothing out of the ordinary for a man. I began to explore the world of crossdressing online; I was amazed at all the resources available. I made friends with some of the more experienced 'gurls' who were invaluable in their coaching of my transition.

Not knowing exactly what I wanted, I began to explore crossdresser dating sites online. That's how I met 'Daddy.' I won't tell you his name. When I told him I was going to begin telling my story on Literotica, he insisted I not use his real name. After all he's done for me, I willingly complied.

I met Daddy in one of the chat rooms. Daddy was a multi-millionaire. I don't mean tens of millions; I mean hundreds of millions. He was thirty years older than me. He was married but his wife had lost all interest in sex, his sex life was non-existent. He'd discovered crossdressers online and loved the fact that they loved to dress so sexy.

He was clearly infatuated with my photographs but was also a complete gentleman. He showed complete faith and trust in me as he began to shower me with gifts, the kind of gifts I used to give my girlfriends. He asked that I take pictures of myself wearing those gifts and sharing them with him only. After a few months of building that trust, he asked me to meet him in person.

We met in Las Vegas; he paid for my airline ticket and hotel suite. We didn't have sex that first time. We just got to know each other better, the way you can only get to know one another better in a face-to-face situation. We laughed together and enjoyed each other's company, no pressures, no expectations. Daddy told me hadn't enjoyed being with a woman the way he was enjoying being with me in years. That was the beginning of our mutually satisfying relationship.

I became Daddy's mistress. He gave me a credit card to be used only to buy things for my female persona. There were no limits on my purchases. Clothing, make-up, lingerie, stockings, heels.... It didn't matter what I bought. Cervin stockings, La Perla and Coco de Mer lingerie, Cle' de Peau Beaute' and Dior makeup, Louboutin and Mischka shoes, money was no obstacle. Daddy enjoyed seeing me in my glam purchases as much as I enjoyed dressing up in them.

Eventually, I began to pamper myself even more. Electrolysis treatments, makeovers, none of that mattered to Daddy. I was making myself more beautiful, sexier for him and he loved it. I even began hormone treatments, although in very small doses. My breasts grew out to a B-cup; large enough to give me a visibly feminine figure when I dressed to accentuate them but small enough to hide under baggy shirts when I needed to present my male self.

We were in Monte Carlo. Daddy's wife was with him; he had gotten me my own room. She wasn't much of a night person and after they had eaten dinner, she always went back to their room before going to bed early. She knew Daddy liked to gamble. What she didn't know was that Daddy was gambling on her not finding out about me!

I finished rolling both stockings up my legs and attaching them to the garter clips of the black satin, open-bottom, body briefer. It was strapless because I was going to be wearing a black sequin shoulderless cocktail dress that hit just below mid-thigh. It barely covered the tops of my stockings. I slipped on my black sequin open toe, Louboutin stilettos with cut-out sides and sat down to do my makeup.

I went with an evening look, dramatic but not over the top. Daddy did not want me looking like some common street walker. I had gotten my hair and nails done at the finest salon in Monte Carlo earlier that day. My nails were done in an electric red polish by Dior and I set about matching my makeup palette to that color. The eyeshadow, lip gloss, and rouge I applied, all complemented my nails.

I slipped fingerless black satin opera gloves up my arms and began to put on my jewelry. My Adam's apple was virtually non-existent. It's a myth that only men have them and that they're all pronounced. That allowed me to wear necklaces other than chokers. I chose a ruby and white-sapphire tear drop necklace in sterling silver with matching tear drop earrings. I placed a cuff bracelet on one wrist and multiple bangle bracelets on the other. I finished my jewelry off with four matching ruby and white-sapphire rings: one each for the pinky and index fingers of my left hand and ring and middle fingers of my right hand.

Just then there was a knock on the door to my suite. I grabbed my black sequin clutch purse and opened it. There was a mountain of a man standing there. He was 6' 6" tall and all muscle. He had movie star good looks; he was a man you could call 'gorgeous' and it in no way demeaned his masculinity.

"Good evening, Miss Margeaux. I'm here to escort you to Mr. Smith's gaming table." (I'm guessing you know Mr. Smith is NOT Daddy's last name but I'm throwing this disclaimer out there just to make sure.)

"Thank you, Christopher. As always, I appreciate your punctuality and attentiveness." I smiled up at him, he smiled back. Inwardly, I sighed. I had tried seducing Christopher shortly after I started dating Daddy, but he would have none of it.

"Miss Margeaux, I'm going to say this one time and one time only. I'm the head of Mr. Smith's security detail. I will never betray the trust he has in me. And if you're going to be his girlfriend, I suggest you make sure your relationship with him is monogamous unless he gives you permission to do otherwise. If you do cheat on him, I'll find out and what happens afterwards won't be for the faint of heart. Are we clear?"

I gulped and nodded. "I will say that you are easily the most beautiful woman he's ever been with. I would consider myself lucky if a woman as beautiful as you wanted to be with me someday." That took a little bit of the sting out of his words after being stonewalled by him.

I slipped my hand through his arm, and we went to the elevators. He took me to the casino and Daddy's private room. Daddy was positively beaming when he saw me. He stood up, I was slightly taller than him in my heels. We kissed each other on both cheeks, European style, and I brushed my lips gently against his.

"Margeaux! You never cease to amaze me. Every time I think you can't possible look any more beautiful, any sexier than the last time we were together, you manage to exceed all my expectations."

I giggled appreciatively. "Thank you, Daddy. I do it all for you." I leaned in to give him another kiss and let my tongue play over his lips. "I can't wait until we're alone upstairs in my room." I whispered seductively in his ear.

He smiled at me and returned to his Blackjack game. A waiter appeared with my drink. Daddy knows I like white wines and had clearly already ordered for me. "A 2019 Louis Latour Montrachet Grand Cru for Madam," he said. He waited patiently while I took my first sip. "Exquisite!" I told him. He smiled, "Madam's bottle is on ice, chilling. I will refresh your glass as needed."

I slipped one hand through Daddy's arm and sipped my drink with the other. Apparently, he had been on a bit of a losing streak but that changed when I arrived. He grinned as he said, "My gorgeous good luck charm, you've turned my losing ways around." I just smiled and nodded. I had learned Daddy didn't really want to engage in any conversation when he was gambling.

He continued to win more than he lost, he had a small fortune in chips on his side of the table. (Well, it seemed a small fortune to me. It was probably just tip money for Daddy.) I'd had three glasses of wine by this time. There was a small lull in the game as the dealer was opening new decks of cards. "I'm going to run to the bathroom. I'll be right back." I whispered in his ear. He nodded, his attention clearly on the game.

I slipped out the door of his private room and headed to the bathroom down a small hallway. After relieving myself and touching up my makeup, I left to go back to Daddy. As the door closed behind me, a hand clamped around my mouth making it impossible for me to scream. The arm around my waist lifted me from the floor. "Damn, you smell as good as you look," a drunken voice slurred in my ear. "I'm going to love every second I'm fucking you." He began to drag me back down the hallway away from all the hustle and bustle of the casino.

Just as suddenly as he had grabbed me, I was free. I heard a sharp crack like a stick being broken. Christopher stepped around from behind the drunk and placed himself squarely between us. "You have compound fractures in both bones of your forearm. You need to get those set and cleaned as quickly as possible. If they get infected, you'll need to get your arm amputated. And if I ever see you in this casino again, I'll kill you."

The drunk stumbled down the hallway, mewling in pain and fright. Christopher watched until he was gone. Turning to me, he asked, "Are you alright?" I fell into his arms sobbing. He held me gently and just cooed to me like a mother trying to calm a crying baby. Soon enough I stopped. "You might want to go back into the bathroom and check your makeup. I'll be waiting here."

Looking into the mirror, I saw my eyes were red and my face blotchy, some of my makeup had smeared. Sighing, I reached into my clutch and repaired the damage. True to his word, Christopher was waiting in the hallway for me. He took my hand, put it through his arm and led me back to Daddy's private room. "I don't think there's any need to worry Mr. Smith about this. And maybe next time, please let me know before you leave the gambling suite?"

I nodded, unable to find the words, knowing I would never be able to thank him in the way I really wanted to thank him.

I rejoined Daddy at his gaming table. He continued to win more than he lost and was enjoying himself immensely. It was starting to get late when he decided to stop for the night and turned in his chips for his winnings. He escorted me upstairs to my room; Christopher followed us at a discreet distance.

We went inside; I knew that Christopher had stationed himself outside my door and would be waiting to escort Daddy back to his room.

"Margeaux, I'm sorry I wasted so much time gambling. I can't stay long. Could you please suck me off? No one gives head like you, and I know I'll sleep like a baby tonight if you do."

I made a pretense of pouting. "Daddy! I thought we were going to spend more time together tonight. Promise me we'll have a night all to ourselves, no gambling? Promise?"

He smiled at me. "I promise. A night just for Margeaux and her Daddy before we leave Monte Carlo." He sat there for a long minute, just staring at me, and then stood up, unbuckled his pants and dropped them and his underwear down to the floor. His raging erection was throbbing, all 5 1/2" of it. Not too big around either, I had practiced on longer dildos than Daddy. His money and his generosity made up for any deficiencies between his legs!

I knelt in front of Daddy and grabbed his sack in one hand and his cock in the other. I tickled his balls while I slowly licked up and down the length of his entire shaft. I just engulfed the head, licking the slit with my tongue. Then I licked up and down the shaft again while my painted fingernails gently caressed his balls.

Daddy was groaning now. "Oh Margeaux, you tease. You're so fucking hot. Suck me baby; I want to cum inside those painted lips of yours."

I put Daddy's cock in my mouth again and this time sucked all the way to the base. As I came back up towards the head, I wrapped one of my hands around his pulsating erection, stroking him while my other hand fondled his balls. I was giving Daddy a hand job and a blow job at the same time! I began to pick up speed, sucking and stroking him faster and faster. He put his hands behind my head and began to fuck my face. I reached around behind him, cupping his ass cheeks in my hand and pulled him into me. I was easily able to take his 5 1/2" inside my mouth; I've had lots of practice!

Daddy was panting and cussing. "Oh fuck, oh shit, oh yes Margeaux. Oh fuck, oh shit, oh yes Margeaux. Suck me, suck me, SUCK ME!" And with that, Daddy began to cum inside my mouth. I swallowed it all, every drop and was staring into his eyes while he stared back into mine with a dazed expression. When I had drained him dry and licked every drop of cum off his member, I stood up, facing him.