Penthouse Suite Weekend - Night 1!

I was luxuriating in my tub; taking every possible minute to soak. I had already used my depilatory from neck to toe and showered it off before my bubble bath. I had just finished my third douche and was finishing my second shave. I was smooth from the nose down and baby soft. Sighing because I wanted to continue to enjoy soaking, I got out of the tub and toweled myself dry. I rubbed myself with unscented hand and body lotion from neck to toe. I sprayed my favorite perfume, Egyptian Musk, on my inner thighs, behind my ears and on my wrists. The blood red nail polish on my fingers and toes had dried long before I got in the tub.

I slipped into my prosthetic bodysuit with the silicone breasts, vagina, and open bottom. I pulled on a black satin and lace garter belt followed by a pair of French cut black satin and lace panties. I threaded the six garters underneath the panties. I put on a black satin and lace bra, even though the silicone breasts did not need the support. I rolled the sheerest of 15 denier, jet black, Cuban heel and toe, back-seam stockings up each leg and clipped them onto the garters. I slipped black silk, open-toe shoes with 5" stiletto heels onto my feet. Then I pulled on my black satin and lace camisole and half-slip to complete my underwear.

I sat down at my makeup table and took my time. I plucked a few random eyebrows to complete the arch I had already thinned out. I used volumizing mascara to make my lashes really pop. My makeup palette matched my nail polish. Not quite night-time makeup, it was still very dramatic. I used my curling iron to put lots of waves into my raven black hair which I had just dyed yesterday.

I put on my black silk pencil skirt. It was 4" above my knees and had an 8" back slit. You could easily tell I was wearing garter stockings from the back when I walked. I buttoned up my sleeveless white silk blouse and slipped on the black silk jacket with half sleeves that was part of my skirt suit. I put on a black silk pillbox hat with a fishnet veil that came just below my nose and cheekbones. I added mid-forearm length, black silk gloves. The final touch was my matching cubic zirconia jewelry set. It consisted of tear drop earrings, sweetheart necklace, multiple bangle bracelets for both wrists, and five rings for various fingers on both hands.

I left the private dressing room of my hotel penthouse and walked out into the common area. I had used some of my bonus money to rent this suite for a weekend at the ritziest hotel in the city. It was expensive but worth it. My wife and son were at her parents' house for the next four days so I was treating myself to what I hoped would be a relaxing and sex-filled weekend.

I looked in the mirror and blew myself a kiss. "Maria, you've outdone yourself again. You look like a 1950's debutante! If there was any way Luke (my male persona) could get into your panties, he'd want you. Badly!"

I picked up my black silk clutch purse, made sure I had my room key, and headed to the elevators. When I got downstairs, I stood in the entrance to the lounge area. Nearly every head swung in my direction. There was jealousy on the faces of most of the women there and lust on the faces of most of the men. I strode to the bar knowing that the back slit on my skirt would reveal my stocking tops.

"I'd like a glass of Hennessy Timeless Cognac, please." I told the bartender. He smiled and nodded at my choice. I decided to sit at the bar, near the end away from the entrance. I sat down, crossed my legs, half turned the bar stool so I could see the tables, and began to sip my drink. I deliberately left a lipstick imprint on the rim of my glass. I was approached by the occasional businessman. Most were socially clumsy and not very good conversationalists. I'm sure some of them may have even thought I was a high-priced call girl. I was aloof and distant to them, so they soon realized I wasn't interested and walked away.

Then a very gorgeous young man came up to me and asked, "Ma'am, is it OK if I buy you a drink and sit with you for a while?"

"Certainly. But are you even old enough to buy me a drink?" I smiled and winked at him to let him know I was teasing.

"Yes, ma'am. My 21st birthday was just two months ago!" he said proudly.

I laughed and invited him to sit. He sat down, I signaled the bartender and after carding the young man, he brought me another Hennessy and him a Tito's and cranberry.

"I'm Maria. And you are?" I introduced myself.

"I'm Liam. Liam Stansberry."

"Nice to meet you, Liam. Before we go much further, I want to make sure you understand I'm almost old enough to be your mother. I'm extremely flattered that a beautiful young man like you wants to have a drink with me, but I also want to make sure you know exactly, or nearly, how old I am. A woman never tells her exact age!" I smiled and winked at him again.

Liam smiled back. He really WAS a beautiful young man. He was probably 6' 3" tall, maybe 220 pounds of solid muscle, had dark, dark brown hair and hazel eyes, and the cutest dimples when he smiled.

"Oh Maria, I'm the one who's flattered that an absolutely gorgeous woman like you would even think about having a drink with me." He was blushing when he said this, it only made him that much more attractive. "Are you in the movies or on a show on any of the streaming services?" he asked shyly.

"Oh Liam, you dear boy! Such flattery. No darling, no. I'm just an ordinary woman and have no claim to being on anyone's A-list or even B-list."

"Maria, whatever else you are, I know you're anything but ordinary. You're the most beautiful woman I have ever seen in person in my life!"

I put my hand on his knee, leaned over so he could get a good whiff of my perfume, and kissed him gently on the cheek. I leaned back into my stool but kept my hand on his knee for another few seconds before I pulled it away. "Liam, you say the sweetest things. Tell me about you."

He looked startled for just a moment, touching his cheek where I had kissed him with one hand and the spot on his knee where I had touched him with the other hand. He blushed again. We chatted. He told me his parents were recently divorced. He loved them both dearly, but they were still angry with one another. He had finally asked both of them not to talk about the other one in front of him because it hurt him so much to hear them saying those horrible things about each other.

"You're very wise for your age, Liam. I hope your parents respect your wishes. They need to work this out and should definitely not be putting you in the middle."

He smiled wistfully, nodded, and said, "So far, they are. I'm torn that I feel like I can't be there for either one of them but they're not at the stage where they can have a conversation without saying spiteful things about each other."

I was finishing my third Hennesy and Liam was finishing his second Tito's. I looked him directly in the eyes and said, "Liam, would you like to come upstairs to my room? We can have our next drink up there."

His eyes got big, and he just stared at me. "Y-ye-yess, Maria. I'd love to go to your room to have a drink."

I stood up and led the way. With every step I took, my stocking tops were exposed to him. I glanced over my shoulder and caught him staring. He realized I had seen him and started blushing again, looking down at the floor. I stopped until he caught up. "Dear, sweet, Liam. Don't be embarrassed. It's turning me on to see you looking at me like that. Have you ever made love to a woman in a garter belt and stockings before?"

Liam gulped. "N-n-no. The only place I've ever even seen a woman in a garter belt and stockings before is on the internet."

I giggled. Liam just realized what he'd told me. "Honey, please don't be embarrassed on my account. There's nothing wrong with looking at a little porn. Do women in garter belts and stockings turn you on?" He gulped again and nodded.

We reached the elevators, and I used my room key to get us to the penthouse floor. We went to my suite and when I opened the door, Liam gasped. "A-ar-are you rich?" he asked.

"No, dear. Not even close. I just decided to treat myself for the weekend."

We walked inside and I led him to the sitting room where there was a wet bar. "Would you like another Tito's and cranberry?" I asked. He nodded and I mixed his drink and brought it to him where he was sitting on the couch. I went back, poured myself a brandy, and sat down in the comfortable recliner across from him.

"Liam, before we go any further, we need to have this conversation. During your porn surfing on the internet, have you ever seen or looked at crossdressers before?"

Liam just stared at me dumbfounded. The magnitude of what I was asking dawned on him. "M-Ma-Maria? Are you trying to tell me you're a crossdresser?" I nodded yes. "N-n-no way. No fucking way!" he almost shouted.

"Liam!" I said firmly to get his attention. "Baby, if this is a problem for you, then you should probably go. Now! If you're at least willing to listen to me without getting angry, then you can stay. Either way, I want you to leave whenever you feel like you need to leave but know that you're more than welcome to stay as long as you want to stay."

He gulped, nodded, and blushed again.

"Liam, can I ask you a question?" He nodded. "Have you ever masturbated looking at pictures of crossdressers on the internet?"

This time he blushed beet red. "Yes, but ONLY if I couldn't see their penises. I needed to keep up the illusion they were real women. I have never masturbated to a crossdresser if I could see her penis. I just scrolled past those pictures as quickly as I could."

"Then we have something in common, baby. None of the men I've made love to has ever seen my cock. That's my choice. I wouldn't have allowed it even if they had asked. There are as many flavors of crossdressers as there are people in the world. Some crossdressers will only have sex with other crossdressers. Some crossdressers want their cock involved in their sexual activities. If you can think of a sexual preference, I'm sure there are crossdressers out there who will meet that preference. Me? I like the full illusion that I'm a woman. I like men who like the full illusion that I'm a woman. Doesn't make me right and other people wrong, just telling you what I like."

I stood up. I began to undress. "Wh-wha-what are you doing, Maria?"

"What does it look like, silly? I'm undressing. For you. Like I said earlier, if you feel the need to leave at any time, please do."

I had draped my jacket over the chair. I walked to the closet to get a hanger. I unbuttoned my blouse and took that off. I put my blouse and jacket on the hanger and hung them in the closet. I got out a hanger with alligator clips on it. I reached behind me; unzipped my skirt and took that off. Soon it was hanging in the closet next to my jacket and blouse.

I was standing in front of Liam in my black satin and lace half-slip and camisole. "Well?" I asked.

"Um, well what, Maria?"

"Can you tell yet? Can you tell I'm not a woman?"

"N-n-no."

"Should I keep going or would you like to leave?"

"K-ke-kee-keep going. Pl-please?" he added.

I lifted my arms straight up and slipped the camisole over my head. Underneath, all I had on was my black satin and lace demi-bra. The cups held my silicone breasts up and out but left my nipples completely exposed. I slowly, slowly slid the half-slip down my hips, past my thighs, knees and ankles until it was on the floor. I stepped out of it, picked it up and put it with the camisole.

Now I was standing in front of Liam wearing only my black satin and lace bra, panty, and garter belt set, black stockings and stiletto heels, silk gloves, hat with fishnet veil and glistening jewelry set. Liam was staring at me, licking his lips and absent-mindedly rubbing his crotch. I put my thumbs in the waistband of my panties and rolled them down my legs in much the same way I had taken off my half-slip. I put the panties in my lingerie drawer with the camisole and slip.

I deliberately walked over to the door, very slowly, and opened it. I just stared at Liam. He looked at me confused. "Wh-wha-what? Are you asking me to leave, Maria? I-I-I th-thought you wanted me to stay."

"I want you to do what you want to do, Liam. If you want to leave, then I hope you'll leave. If you want to stay, I hope you'll stay. If you stay, I promise you'll have the most mind-blowing night of sex you've ever had in your young life. But it has to be your choice!"

Liam stood up and walked to the door. For a moment, I thought he was leaving. Then he very gently but very firmly closed the door behind us. He walked up to me, took me in his arms, and kissed me deeply, passionately. His hands were roaming all over my body, rubbing my ass cheeks, my back, my hair, pulling me to him. He pressed his body against mine and pulled my body close to him.

"Oh Liam. Oh baby. Oh darling. Mmmm, Liam, Liam, Liam. You've made Maria a very, very happy woman. I'm going to make you a very, very happy young man."

I led him back into the room. I began to take his clothes off in front of the full-length mirrors in my dressing area. He was watching intently as a 'woman' dressed the way he had fantasized about and masturbated to was disrobing him. When he was completely naked, I molded my body against his and kissed him as deeply and passionately as he had me at the door to my suite.

His erection was pressing against my stomach, I could feel it throbbing and pulsating as if it were a live animal. I slowly began to kiss my way down his body, sucking and licking his nipples and stomach. I was on my knees in front of him when I looked at his 9" cock, standing at attention.

"Mmmmm, Liam." I cooed. "This cock is so beautiful. I can't wait to suck it. I can't wait to drink it. I can't wait until I'm lying on my back with this cock buried inside me."

I was holding just the tip of his cock in my gloved fingertips. I began to slowly run my tongue up and down the underside of his erection. I continued to do this, slowly, until Liam began to sway back and forth, begging me, "Maria, oh Maria. Please, please, oh please take me inside your mouth. I have to feel your lips wrapped around me. Suck me, Maria. Oh, please suck my cock."

I wrapped my lips around just the head of his cock and began to run my tongue around the underside of his prick. I was staring into his eyes while I did this. Liam was groaning. I cupped his ass cheeks and pulled him into my mouth slowly. My hands began to wander down his thighs, caressing him from ass cheeks to knees and back again.

"Mmm-mmm-Mmm-aria!" Liam put his hands behind my head and began to fuck my mouth. At first, he was gently thrusting into me but soon began to pick up the pace as he was getting closer and closer to cumming.

I was deep throating him now, sucking and licking his shaft intensely. The fingertips of one hand were rolling his testicles gently while the other hand was gently brushing against his perineum. He exploded in my mouth, screaming as he came. "MARIA! Oh shit, oh fuck, oh yes, yes, yes, yesssssssss! Suck me baby, suck me baby, suck me! I'm cumming for you, Maria, oh, oh, ooooooooohhhhhhhhhh!"

Wave after wave of salty goodness spurted down my throat. I love drinking sperm and I swallowed every drop of Liam's cum. As I licked the slit in his prick dry, his knees buckled a little and he leaned on my shoulders for support.

"I think it's time Maria took you to bed, young man!" I giggled as I guided him to the bedroom. I turned on all the lights. I wanted to make sure Liam got to see me while we were making love.

"Most of the girls I've slept with always turn out the lights." Liam said a little puzzled.

"And I'm not most of the girls you've slept with, darling. I want you to be able to look at me and see me while we make love. That is, unless you prefer making love in the dark?"

"Oh Maria, no. I love looking at you, I love seeing your sexy body dressed that way. Watching you suck my cock, the expressions on your face when I came as you drank my cum, that was such a turn on."

"I'm glad I turn you on. Knowing that turns me on. Are there any positions you haven't tried yet baby, something that you've always wanted to try?"

"Doggy style!" Liam said this quickly and forcefully.

I giggled seductively and said, "I think we can check that off your list right now, darling Liam!"

I pulled the covers back from the bed and crawled onto the white satin sheets on my hands and knees. The white contrasted nicely with my black outfit; Liam would continue to get his visual turn-on.

Liam got into bed and began to position himself behind me. "Be a dear and grab that tube of edible lubricant from the nightstand. Squirt some up my ass and a little on the tip of your prick." Liam did as I requested, I could feel the cool lubricant inside me. I was watching him in the wall-to-wall, floor to ceiling mirror next to the bed as he knelt behind me and began to penetrate my rosebud.

"Ooooohhhh, baby, oh darling, OH Liam!" His 9" cock was thick and filled me up. His cock was easily the biggest I had ever had inside me. He steadily pushed inside me until his thighs were resting against my nylon-covered thighs. "Look at us in the mirror, baby." He turned his head and his eyes bulged out when he saw us. His cock started throbbing inside me. "Mmmmm, you like that daddy? Maria likes that, daddy. Maria wants her sexy young daddy to fuck her, hard and fast!"

Liam obliged and soon he was pounding my ass cheeks, sliding in as far as he could go and then sliding back out until just the tip of his cock was inside me. His cock was so huge and filled me up so completely, I knew I was going to cum. "L-Li-Liam. Quick, baby, quick! Start stroking my nylon thighs with your hands."

Liam obliged and the feeling of his hands through the nylon on my thighs and the monster cock going in and out of me, brought me over the edge. "Sh-sh-shiiiiitttttt. Fuck, fuck, fuck! Cum, cummm, cummmmiiiiiinnnnnggggggg!" We were looking at ourselves in the mirror. Liam smiled as he saw the orgasmic intensity on my face. He continued to pound my ass until my orgasm subsided.

"Mmmmm, baby, you're amazing. Your cock is amazing, I love the way you fill me up. I love the way you fuck this pussy."

Liam continued to piston in and out of me. He was riding my ass like a stallion in heat. He had the stamina of youth; I had hit the sexual jackpot with Liam!

I started to rotate my hips, first one way, then the other. I was squeezing his shaft with my ass muscles; I wanted his cum inside me; I wanted him to fill me up with his warm juice. I fell onto my elbows so he could penetrate me even deeper. He kept pumping and pumping; I couldn't believe I was so close to cumming again. I looked at us in the mirror. I looked at this gorgeous young stud fucking this beautiful older woman and the sight brought me over the edge again.

"Fuck, fuck, fuckkkkk. Liam, Liam, Liam. I'm cumming again, baby. You're making me cum again. Fuck, oh baby, oh daddy, oh my DARLING LIAM! Aaaaaaaaaaaaahhhhhhhhhh!!!!!"

My orgasmic cries and the sight of us in the mirror finally caused Liam to join me. "Fuck Maria, fuck Maria, fuck Maria, fuck Maria, FUCCCCKKKKKKK!" He was filling me up again and his cum started to drip out of me. He continued to pump my ass until he was spent, and he collapsed on top of me.

I rolled him off of me and laid him gently on the bed on his back. I kissed him and leaned down to clean him up. I licked and sucked every drop of cum from his cock. "Now it's my turn to clean up, baby. I'll be right back."

I went into the bathroom and let as much of his cum drain out of me as possible. I straddled the bidet and let the warm water deep clean me. Then I grabbed the scented douche and cleaned myself even more. I did some minor repairs to my makeup. Refreshed, I went to join Liam. I stood away from the bed and continued to pose for him.