Sweetness

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A crossdresser meets a man at a snowy hotel.
20.8k words
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Author's Note: Hmmm, a little fantasy, a little wish fulfillment... a sexy little story in real-time... I hope You like it.

***

Friday, February 19th

Tomorrow is my thirtieth birthday.

So I was ready, I took a shot of tequila to calm my nerves, and I took a deep breath.

"Ahh," I sucked in, "Whoo." I blew out.

One more check in the mirror just for the heck of it, then I opened the door. I stuck my head out, I looked to the left, I looked to the right. "Whoo."

'Everybody look to their left

Everybody look to their right

Can you feel that, yeah

We're paying with love tonight'

I had my phone hooked up to my new selfie stick, I had my last one for almost four years. I shut off the music. I put on the camera. I made sure I had my key, then I closed the door. My favorite hotel, my favorite hall, my favorite floor. The hallway was nice and empty, it was long and carpeted, it would cover the sound of my heels. My perfect heels. They were off-white sandals, five inches, a nice strap right up the front, and another around my ankle. I stood by the door, and listened for a couple of seconds, listened for kids, people coming back from a late dinner, hotel employees bringing up more towels or peaches and cream and Champagne. I shook my hair, I pursed my lips, I was ready. I held out the stick, pointed at myself, I could see my mysterious grin on the face of my phone, my full lips. I would smile a little later. I strutted to the end of the hallway, I had a great walk, I knew how to strut, move gracefully. I stopped and looked out the window, the snow was still coming down, it was a crazy day for weather, a crazy day to be trapped in a hotel. I couldn't be happier.

I walked the other way, toward the little kitchen, maybe I was just out to get some ice, some coffee, some unsweetened ice tea. Maybe I was a little peckish while wearing my thin little cocktail dress, showing off all types of cleavage, it could happen. I stopped next to the elevator. I saw the tall blonde in the mirrors. I loved that mirrors were installed next to elevators to distract people, 'women' like me, and give them something to look at while they waited. I watched the almost beautiful blonde, she put her stick over her bare shoulder, she looked completely distracted. I scrunched my face, I stuck out my tongue, I imagined I was a flirt.

"Hi." I did a little wave, I was very feminine when I wore a cocktail dress. I was very feminine when I was in shorts or a T-shirt, almost anything slightly girlie brought me into a different mindset, a different realm of being. I moved closer to the mirror, to check my lip color, it was a little bit rose-colored, the mirror, not my lips, I looked very nice in it. My long blonde hair was styled, parted in the middle, and slightly fluffed up. It went right past my shoulders. When it was straightened it was even longer, but I liked it more full, more bouncy. I had on my peach dress, it was a summer dress, definitely not for February, nor for looking sexy in the snow. The light cotton dress had spaghetti straps and showed off my breasts, my new breast forms in all their glory. I now owned three pairs of them, D cups that slipped over my head and were more of a breastplate, I had C's that slipped into my bra, or I could glue them onto myself. I wore these with a strapless dress, bathing suits, nightgowns, and a few of the dresses I owned. I was now wearing my new favorite. They were expensive, they were from Japan, made of silicone and filled with some sort of gel, they were double D cups and they made me so happy, made me feel so sexy. It was like a shirt, it slipped over my head and came just under my chin. It covered the top half of my body, and my arms, and ended at the wrists and right below my breasts still showing off my tight flat stomach.

I found thick plastic bracelets to cover the end of the forms on my wrists, it was perfect, it looked like all me. I posed in front of the mirrors, taking pictures, my dress tight at the waist and full on the hips. The hem dipped in the middle of my thighs showing off my nude pantyhose, hiding my peach color panties. I had my hand on my hip as I clicked the phone, I was trying to show off my nails, light peach, very long press-on ones. I bought them this afternoon at the drug store, always on my to-do list, with mascara, nail polish, and polish remover. Once I forgot remover, oh boy!

I turned around, I took pictures of my backside, my ass, it wasn't easy.

Ding.

"Excuse me," Three people got off the elevator, watching me, I was stunned. A man, a woman, and a little boy. They held the elevator door for me. I smiled, I got on, I was embarrassed, but I was glad they didn't find me traipsing the hall with my selfie stick. I waited for them to leave. I held the doors, they were beeping like crazy, somebody needed the elevator and I was holding it up, I slipped out and went the other way. I started to head to the ice machine again, I heard it in the distance. I had the stick low taking video of my legs, my ankles, my heels. I thought I heard someone, I hurried into the little kitchen. I loved how I looked walking fast, my hands up for balance, taking tiny quick steps in my heels. I looked at my phone it was after ten o'clock, this was early for me. Usually, I minced around the halls after midnight, after everyone was asleep after I couldn't take it anymore when being alone was too lonely. I needed to go out and show off my legs in the hallway.

"Oh, no." I sighed practicing my voice, "I should have brought an ice bucket, there was one right on my desk just waiting to be filled." I had a finger on my lip, I realized I should have brought some money too, all I had was my key card with me, "Oh, well." I slipped the card back into the slit in my pink phone case. I didn't even have my clutch. The one that matched perfectly with the heels, with this dress. "Maybe later." I cooed, I felt myself smile, I was just being silly, I was being distracted again by my legs, my breasts. Maybe even my Dior Pure Poison.

"Oh, I'm sorry."

I was startled, there was a man in front of me, he was blocking my escape, he was tall, he made me quite nervous. I wasn't used to speaking with someone who wasn't behind a desk or giving me change.

"That's okay, I forgot my bucket." I shrugged, I smiled, I tried to pass, I retracted my selfie stick.

"Use mine." And he held out his. He was smiling, he was looking down into my eyes, with my longer than usual lashes, with my copper eyeshadow. He was glancing at my lips with my peach coloring. "Here I will fill it up for you." I didn't know what to say, so I stayed quiet I had a confused grin on my face, he was being nice. He was being handsome if that's a thing.

The ice machine made so much noise, I was glad I didn't do it myself, I would have woken up the people across the hall. "Come on I will walk you to your room, a pretty woman shouldn't be alone on such a dangerous slippery night, you know snow and all." He was trying to be cute, he was flirting, he was trying to make me comfortable. It was working, I was enjoying being flirted with.

"I'm down this way." He followed me, I'm sure he was watching my ass, my legs in my high heels. I had never run into a man to talk to while I took pictures in the halls. Sometimes a cleaning woman said hello to me, sometimes a manager was on his phone, sometimes just sometimes some of the help was hiding in the stairwells, vaping, or eating. I usually just nodded, I never had to speak, I never had to be followed. "This is me." I tapped my long nails on the door. I opened it, I got my ice bucket. I turned around, he was in my room, I had a man in my room. I swallowed, I got a little tense, a little excited.

We traded buckets. He smiled at me. "Thank you," I said, my hands finally empty, I played with my hair, I had another on my hip again. I felt my long legs get into my favorite position, well, second favorite position. Slightly bent at the knee.

"If you want we could just get a drink at the bar? Save the ice for another time."

"Ooh, I better not, I'm not dressed up for the bar," I told him, I don't know why I referred to my outfit because now he was studying me, looking at my hips, legs, heels.

"You are all dressed for a party, you are quite beautiful, I am so glad I ran into you, heh."

I couldn't believe a man gave me a compliment, I liked it, it did something to the adrenaline in my body, maybe the estrogen too, haha. "Thank you," I looked down at his shoes, he was dressed for a party too. He had on a dark blue suit, nice Italian shoes, he smelled wonderful.

"How 'bout this, I will come back in..." He looked at his watch, he pulled up his sleeve, it was such a masculine move to perform. "A half-hour, if you want to get a drink or something to eat, or just hang out, you know whatever." He smiled again, he was making me relaxed, but I started to bounce a little on my heels.

"We'll see. Don't get your hopes up." I scrunched up my face, my hair hiding one of my eyes, sometimes I was cute too. I followed him to the door. We said goodnight. I closed the door quickly and jogged to see myself in front of the mirror. I wanted to see what I looked like, what he saw, did he see a pretty woman? Did he notice I was a crossdresser? Did he care?

My makeup was still so nice, my cleavage so inviting. I was 5'8" and 140 pounds, I had long legs, a round ass, and longer hair. I wished I had a thinner waist and thicker hips. I looked quite happy gazing in the mirror, my big gold hoops moving against my cheeks, my lips still looking perfectly peach. I threw myself a kiss, then I started to play with my 'pussy' through my peach dress. I was already breathing heavy, I was already excited. I pushed, I rubbed, I started to moan. I realized that I loved talking to a man while dressed up while looking like I was invited to a party, like I had just come back from one. I would have to do that again.

I rummaged through one of my bags, I found it, my favorite six-inch toy. It was a perfect cock, balls and all. I attached it to the desk, in front of the mirror and I pumped it, making believe it was the man from the kitchen. I could smell his scent. I had one hand on the cock and another rubbing my panties. "Thank you sir for walking me back to my room, this is how I thank all the men I run into," I giggled as I started to massage my flat crotch, felt my fingers investigate, I felt like a woman. I always felt like a goddess, wearing my outfits, watching in mirrors, and practicing my lines for men. "Oh, my god, your cock is very big." My lips made an O, my eyes were wide, my hand gripping the silicone cock, I couldn't believe it but I started to cum, I was completely tucked in my panties but I was cumming. My panties felt so wet, I imagined the man was playing with me, kissing me, pushing into me, then fucking me against the wall. I fell back onto the bed exhausted, my legs now in their favorite position. I came so fast, I came so hard. "Sorry sir for cumming so quick. Next time I will wait for you."

I had such a great imagination.

***

This Afternoon...

'Everybody look to their left

Everybody look to their right

Can you feel, yeah

We're paying with love tonight'

I was in the Motel parking lot, my first stop of the weekend. I had the key to the small ugly room in this overcast ugly neighborhood. I picked up my phone I wanted to call my wife, Lora, and get it over with. I lowered the volume of the music.

"Hey, busy?" I asked, she was always busy lately.

"Yeah, probably finish late, but everyone is here, everyone is helping."

"That's good, say hello for me,"

"Mmm, oh, I am going to stay at Mom's all weekend it's gonna be some storm tonight." She sighed, I looked out the window, it was dark for early afternoon. "I might stay 'til Monday, see how bad it gets."

"Okay. Have fun then."

"I will, and I'm sorry I'm missing your birthday. We can celebrate next week or something. Have some cake for me okay? I'll call."

"Okay, love you, bye."

"Bye."

I held my phone, I took a deep breath. She wouldn't call me the rest of the weekend, she would be too busy with her family and the church, painting, cleaning, setting up whatever she was setting up. She would never remember to call.

*

I always stop off at the South Amboy Motel to dress up, to get ready before I go to my favorite hotel. My favorite, in the middle of nowhere, the middle of New Jersey. I shower, I shave a few stray hairs that have popped up since last time. I was almost completely hair-free, for years, just a little strip in my panties, I went and had it done slowly. Lora didn't mind when she found out, she ended up going herself, she thought it was a good idea. 'Cleanliness is next to godliness' was her favorite quote. She was pretty clean, I have to admit. Sometimes she was a little too clean a little too religious too, but I digress.

I cleaned myself outside and in, I had a small bag of toys I was going to play with this weekend. I neglected them for so long and I was missing them, I never took them out at home, ever. I had a suitcase full of clothes, dresses, cocktail dresses, heels. I had been crossdressing since I was young, tiny, now I had to leave my house and lie to the wife, tell her I was working, and get away for a while to become 'Sabrina.' Had to check into a hotel, check myself out for the weekend, just to become the woman I was inside my head. It was crazy but necessary.

I put on my soft dark pink robe to put on my makeup, curl my long hair. I sat in front of the mirror for over an hour and a half until I was satisfied. Just a little bit of eyeshadow and mascara, false lashes, light rose color on my lips. I always make believe I was a businesswoman working away from home. Meeting clients, meeting co-workers, it was a nice little fantasy for me. I slid on my new breast forms, added my bra, panties, stockings. I had a short sleeve black dress. It came down to my knees, when I was 'working' I was very demure, very professional. But, when I was ready to play I was beyond sexy, beyond feminine, in my mind and my soul. I put on two-inch black pumps and then slipped on a long black jacket. I was ready for the boardroom, ready to take orders, ready to give direction.

I had on small round clip-on earrings, a small watch, a big black bag filled with my ID and essentials. Perfect.

This morning when I checked in, I told the older man at the Motel desk that I just needed a shower, maybe a change of clothes, I had been driving all day. Ha, I lived 65 minutes away, a little apartment in Northern New Jersey. I was now back in the car, finally feeling like a woman, I was done with the motel. I put the music loud again.

'It's not about the money, money, money

We don't need your money, money, money

We just wanna make the world dance

Forget about the price tag'

I made a quick stop at a local pharmacy. Always the second stop. I loved shopping as a woman as long as I didn't have to talk to anyone, it made me too nervous. I loved walking the aisles, catching the men and some of the ladies watching me look for tissues, or bending over and reading the ingredients on the back of cardboard boxes. Once I was done, putting away my purse, dropping my purchases in the backseat, I was completely ready for my 'Sabrina' weekend. Next stop my favorite Hotel, The Best Western. Had long halls, wall-to-wall carpet on the floor, and quiet. No one stayed in Hazlet in February, hopefully, I would have most of the floor to myself.

I parked right near the entrance, there was plenty of room, the hotel looked emptier than usual. I took a deep breath, a quick check in the rearview mirror, and made my way in, clicking on the hard marble floor, nodding to the workers who turned to look.

I always called the hotel the morning before, left a message, and I always walked into the Best Western as a woman. I had my credit card with my femme name on it, they always called me Miss. I had been coming here for over five years, I had been mostly married for two of them.

*

I was waiting, slightly bouncing on my heels, I got ready to use my perfect voice. I have practiced for years, on the phone, online, waiting for chances to use it in real life. I greeted the young woman behind the counter. "Hi, I have a reservation." I smiled, I put my bag on the counter, ready to search for my purse.

"Yes, name?"

"Sabrina Langton. Here is my card." I loved holding it with the peach nail color, the longer than usual nails. How does a businesswoman handle such long nails, I thought. Every little move became more feminine, slightly sexier, it was hard to focus.

"Oooh, yes, welcome back. We have your favorite room 1201, here you go."

"Thank you,"

"And this is for the restaurant tomorrow, happy birthday, stop by for cake." She smiled, did a little giggle, and handed me a birthday card. "Oh, and there is a message for you, let me get it." She then handed me a small piece of paper.

I looked at it, then smiled at her, she was being so nice to me, "It's from my boyfriend, he's going to miss my birthday." I made a little frown.

"Aww, well don't fret, the staff will take good care of you."

"I hope so," We laughed. "What's your name sweetness?" That's what I called the few women I talked to when I was being one of them, I didn't even know why, maybe I thought I was being cute.

"Samantha, make sure you come back and say hello, Miss Langton."

"Ha, Sabrina, please."

"Sabrina..." She gave me a huge smile, she was being quite pretty, she was too pretty for Hazlet. I wished I had known her forever. I waved and then drifted off to the elevator, pulling my suitcase.

***

This was what I looked forward to. I counted the days. Coming to this hotel, this room, surprisingly, was the best part of my life. What a great idea it was, what a great way to fulfill my fantasies without Lora or anyone else knowing. She would absolutely hate having a husband that wears dresses, earrings, sanitary pads, and talked with such a feminine voice. I wish I knew she would eventually become homophobic, a little judgemental, and completely to the right before we got married. I wasn't ready for such a sudden change. After the small ceremony, we moved back to her hometown, she got a new job, made new friends, and then had a life-changing experience. It had nothing to do with me, though it changed my life drastically as well. All her new friends thought it was for the better, they were so happy for her. She started going to a church, with her Mother and HER friends, Then WE started going. I was a relapsed Catholic, I haven't gone to mass since I was in St. Peter's grammar school I was too busy relapsing. I didn't miss it. Lora now loved it. It was some type of Protestant offshoot, I didn't even know what it was called. It had a long complicated name and only a few parishioners. Personally, I'd rather hang out in hotels.

"I'm leaving." She would say, "I promised to help clean the rectory, the baptismal, the bathrooms. I promised to check the books, the sermons..." She was at the church a lot. After a while I didn't mind, it seemed to of given her life more of a purpose and it gave me time to be alone with my heels, nothing too complicated, I saved that for my time in the Hotel. Now I was sitting on the bed, getting ready to change my panties again, they were so wet. I have a habit of getting too excited driving in heels.

Now after talking to a man I was getting ready to go for another walk, or maybe even go out for a drink, that would be a first. I had never done that before, never even talked to anyone really, always just myself.

That's what I get for walking around so early.

*

I was sitting on the bed, glancing at my makeup. I put on darker eyeshadow, a little more mascara, and liner. My long nails still looked incredible, they have been on since this afternoon. I curled the bottom of my hair, just big ringlets, feminine and sexy, I wanted to look sexy, I wanted to look like a girl going out for a drink.