I thought I would be a little vulnerable and share something that happened to me recently. Last weekend, I turned 26. It wasn't the most eventful day, but it did lead to this.
"Don't forget we are meeting at 7 for sushi!" I posted in the work chat. I got a few hearts on the comment, which made me smile. I have been a bit of a recluse the last few months, so the thought of going out with some friends felt exciting.
I propped my phone up and pressed play on the video, then went back to the long process of curling my hair. It was nice to get dressed up more than usual, even if it took extra time to get ready. I had redone my nails and was trying out a new pink eyeshadow to match it.
To be honest, I was a bit distracted by my phone. Sometimes I'll turn on porn, mostly as background noise as I work or do things around the house, but I was a little enthralled.
I checked the clock. I only had an hour before I had to be at the restaurant.
"Shit," I whispered, stumbling half-naked out of the bathroom.
Fortunately, I had already picked out my outfit the night before, pieces sprawling over my bed in indecisive piles. I had decided on some light, washed-out, high-waisted jeans, a cropped graphic tee, a denim jacket to throw over it, and my favorite open-toed boots. I even wore my lucky black cat choker.
I got to the restaurant with five minutes to spare. A little lip gloss and an excited giggle, and I was on my way inside. I sat at the reception area, but I didn't see anyone. Every time the door opened, I grinned, only to have it fade when I didn't recognize the person.
Fifteen minutes passed. Then fifteen more. And still, it was just me. After 45 minutes, it was apparent that no one was coming. I was so frustrated that when I pushed open the door to leave I bumped into someone.
"I'm so sorry," I said, "I didn't see you."
"Stephie?" grunted the man. I looked up at him.
"Charlie? What are you doing here?" I asked.
"You said sushi was at 7, right?" he asked, checking his phone. "I know I'm a little late."
"No," I laughed, "what are you doing in Utah? Don't you live in Texas?"
"Oh!" he smiled. "I have to be at a meeting tomorrow. I would have gotten here sooner, but it took a while to get checked into my hotel and fight traffic." He frowned at me. "Are you leaving?"
"I am the only one that showed up," I shrugged. "Or, I was."
"Well, if you haven't eaten yet, want to get a booth?" asked Charlie.
"Just the two of us?" I asked.
"Why not?" smiled Charlie. He held open the door and let me back inside.
All the frustration that I had felt moments before seemed to wash away as we were led to a corner booth. I thought Charlie looked handsome. He was a bit older than me, but that had never bothered me.
"I like that colour on you," I said, flattening the wrinkled corner of his shirt. "Looks good."
"You think?" he asked. "Becca picked it out. I wasn't so sure."
Married, how did I forget that? I thought.
"I like it," I smirked.
He let me scoot into the booth first. "You look really cute tonight," Charlie said, sliding in next to me. I looked to my left and right as if the compliment had been for someone else.
"Thank you," I blushed. "That is sweet of you to say. Do you want to start with some appetizers?"
I leaned over Charlie with my phone to scan the QR code and pull up the menu. Sloppy moans erupted from my phone with the video I had forgotten to close.
"Bah!" I yelped, failing frantically to close it.
"Woah!" laughed Charlie.
"I am so sorry-- I don't know-- I um-- I am so embarrassed," I whispered.
"I didn't know you were into that stuff-- you are always so shy," said Charlie with poorly hidden laughter.
My cheeks flushed with a color to match my eyeshadow.
"If you want to leave, I understand," I began.
"Wait-- you are serious? Hey, Stephie, honestly, don't think anything of it."
"You sure?"
"Positive," said Charlie. "Actually, do you think you could forward that to me?"
"Ha ha," I smiled. "I feel like I might pass out."
"You are overthinking this way too much," he said, gently grabbing my arm. "Here, look, just to make you feel better." Charlie unlocked his phone, filtering through a tab and opening a video of his own. "See."
I blinked a few times. "Oh," I managed.
Charlie quickly closed his phone and turned away. "Actually, I think you were right. That was way more embarrassing than I thought it would be."
"Right?" I giggled. "I mean, I would watch that video, just not here, sheesh Charlie."
"Hey!"
"Alright, how about this? We agree never to speak of this to anyone?"
"Oh I'll take that deal!"
We laughed it off, then ordered our food and some drinks. We chatted about work mostly, then got to know each other a little better. It was easier given that we had shared an embarrising moment. I liked Charlie. He was always kind, and the more time I spent with him, the more attracted I became. I knew he was married, so any flirting was mostly harmless. Mostly.
"Oh wait," said Charlie suddenly. "It was your birthday last week, right?"
"Yup. I turned 26. Was a bit of a boring day, actually."
"You didn't go out?"
"I drank wine and watched Netflix in my pajamas," I laughed.
"Netflix," he gestured. "Mmhmm."
I pushed his arm.
"I haven't been out with friends in a while," I continued. "That is why tonight was sort of a big deal for me. I am really glad that you came, by the way."
"Who could turn down sushi," he jested.
I started to really relax as the night went on. And I realize now that I was getting a little too flirty. I would touch his arm when he made a joke, gradually sat closer to him, teased a boot against his leg as if it had been an accident.
It didn't help that I thought he was flirting back. He put a hand on my knee when I said something funny. Constantly looked from my eyes to my lips. Gave me random compliments.
It is all just playful, I thought at one point. He is married, it isn't flirting.
He brushed a stray hair behind my ear and I turned bright pink again.
"Sorry, I should have asked before I did that," Charlie said nervously.
"No, no, it is alright," I said, leaning into him a little. "It was bothering me anyway. So really, you did me a favour." I looked at the time. "Getting late. We should probably get the check, ya?"
He seemed sort of bugged by the comment, but I wasn't sure. We paid the check, Charlie kind enough to walk me to my car. I gave him a quick hug and then started for my car door.
"Feel free to turn this down," CHarlie said behind me, "but I brought some hot chocolate mixes with me that are incredible. If you want to have some with me? The hotel is not far."
I wanted to say yes, but I hesitated. "I should probably get going. I am watching my niece tomorrow, so I should get ready for that."
Charlie waved a hand and smiled. "No worries. Thanks again for getting sushi, definitely hit the spot."
"It really did." I pursed my lips and fumbled with my keys.
Charlie started to walk away.
"The hot chocolate is really that good, then?" I blurted.
"The best. I promise."
"A quick hot chocolate," I said, "and then we can call it a night."
I followed Charlie to the hotel, biting my lip as we got in the elevator. It is just hot chocolate, right? I really shouldn't be alone in a hotel room with him. What if it is more than hot chocolate? I wouldn't mind if--
Charlie gently guided me through the elevator door as it opened. He flipped on all the lights as we entered the hotel room. "Make yourself comfortable. Shouldn't take long." He got a couple of mugs from the cabinet and some packets from his suitcase, then got to work.
"It is a nice view," I said, looking past the balcony window. I caught my reflection, adjusting my hair a little and straightening my jacket.
I pulled out my phone, mostly out of habit and a little out of nervousness. Opening and closing tabs a bit absently.
"Oh good, we can finish that video you were showing me," Charlie said from the kitchen.
"No way," I laughed.
"Too bad," smiled Charlie. I couldn't tell if he was serious or joking.
"How about this-- you open up a category on your phone, and then I'll pick one to watch," I jested.
"Hmm, alright," said Charlie, flipping out his phone. The microwave beeped as the first mug finished heating up. He pushed his phone towards me. "Here."
I picked it up, thinking it was an elaborate joke. I imagined that it would be a page of kittens on Google, and we would laugh. I was wrong.
"Swallow," I whispered, reading the category.
"I saw that you had it tagged when you flashed your video," Charlie grinned. "I am curious."
I bit my lip as I searched, finding myself a bit turned on. I clicked one, then paused it.
"Here you are," he said, handing me a steaming mug. When our fingers touched my heart leaped.
"Thank you. Mmm, this is good."
"See, I told you! I am glad that you like it."
We went out on the balcony, sipping quietly. Charlie held the phone between and pressed play.
I remember the title, 'Big Cock Fits Perfectly In Tight Jucy Pussy (Lots Of Facial POV) Elena Ross.'
"She's cute," whispered Charlie. "I like her fishnets. And she has pretty feet."
"She is cute," I whispered. "And nice boobs."
It was a little strange watching the video with Charlie, but also really fun. I've never watched it with someone before.
"I like how sensual she is when sucking," he said.
"Yeah, it's as if it were her first blowjob. So gentle."
The more I watched with him, the hornier I was getting. The wind caught beneath my jacket and I shivered. Charlie moved closer to me. I looked up at him. He was so close to me. And before I knew what had happened, I kissed him. Our lips held together for a long moment.
"I am really sorry," I said, stepping back. "I don't know what I am doing. I think I should go."
Charlie set down his mug and stopped me, kissing me back. I like the way that he held my chin with his hand.
One kiss turned into two. And then a few more. And before I knew what was happening, I was breathing hard, swirling my tongue against his. Biting down on his lip. Savouring the taste. We moved step by step back into the room.
Where I had been cold, I was now hot. I took off my jacket between our kissing, laying it on a chair. Charlie sat me down on the end of the bed, pushing me on my back a little. I expected him to get on the bed but he grabbed my ankle and lifted my leg lightly.
He unzipped one of my boots, sliding it off.
"Fuck," I moaned.
"You like that?" whispered Charlie. He slid off my other boot and held my bare feet in his hands.
"Yes daddy," I said, not thinking.
"Are you going to be daddy's good girl?" He kissed along my ankle, and I moaned a little. Then more when he kissed my soles. Then more when he started sucking on my toes.
"Fuck. Yes, daddy, don't stop," I whimpered.
It was so simple and yet so exhilarating. I sat up as he set my legs down, still sitting at the edge of the bed. I looked up at Charlie standing in front of me, reaching to unbutton his shirt. He leaned down and we kissed as I undressed him.
The palm of my hands felt cold against his chest. His shirt fell to the ground, and with it went mine. Charlie ran a finger beneath the shoulder strap of my bra. Just teasing me. I decided to tuck my fingers into his belt to tease him back.
Charlie stood me up, then fumbled at the button on my jeans. I wiggled out of them, tossing them with the rest of our clothes. I couldn't stop kissing him. And now, standing there in just my bra and thong.
"I want you," I whispered.
When I unclasped his belt and unbuttoned his jeans, Charlie pushed me onto my knees. "Thats a good girl, get on your knees."
I pulled his jeans down at his hips so that his boxers stayed on. I could see his cock bulging and stroked him on the outside of his boxers.
Charlie groaned with pleasure as I felt him. I watched him as I slid down his boxers and his cock sprung out against my face. My mouth watered at the sight. I grabbed his shaft, licking and sucking softly at his balls as his cock lay across my cheek. I was slow with how I used my tongue, working up and down the shaft.
"I want your cock in my mouth," I said. His cock was warm against my tongue as I held the tip with my lips. I swirled my tongue around the ridges of his cock feeling every bit of it.
"Show me what your mouth can do," he said. Charlie moved to the edge of the bed, careful to keep his cock in my mouth as I crawled on the ground. I opened his knees and slid between them. Charlie put a hand through my hair, sliding his cock deeper into my mouth.
I loved the way that it curved down my throat. I gagged but kept him in my throat, looking up at him as he moaned. I gasped with a sloppy breath, spitting onto his cock as I started to suck.
"Oh fuck, don't stop," he moaned.
I pushed his cock against the back of my throat, working it in and out with sloppy gasps.
Charlie liked when I pulled on his balls, massaging them as he fucked my mouth. He pulled my hair back, and I let him have his way. I liked how strong and forceful he was with me.
I wonder if it feels as good as his wife, I thought. It made me sit back and catch my breath. Charlie seized the moment to unfasten my bra. I moaned as he squeezed my little breasts. He leaned forward and bit my nipple, sucking hard. I tilted my head back, my fingers gliding up and down his wet cock.
He pulled me by my hair onto the bed. I got on all fours, my bare feet hanging off the edge. I was nervous. Charlie knew that I was a transgirl, but did he know I had a transcock? My tuck was barely staying beneath my thong. And now, with my legs spread, I was nervous about what Charlie would think.
He grabbed something out of his bag and stood behind me.
I held my breath as he slid down my thong, spreading my cheeks and rubbing a finger on my asshole. My limp transcock swung between my legs, and I quickly hid it with my hand. Charlie tossed a condom wrapper next to the bed and spread my ass.
I yelped as he pushed his cock into my asshole. It was so tight, and his cock so big. When he had the tip in, he grabbed my wrists and held back my arms. It struggled a little, but he held me down until he was balls-deep against my asshole.
Back and forth he thrust, slowly, and then fast and deep.
"Fuck, fuck, fuck," I moaned. I could feel my transcock getting harder. I tried to free my wrists but Charlie held them firmly. When he let go, I braced against the bed, still on all fours. My asshole thwomped as Charlie pulled out his cock.
I was shaking with pleasure. Looking behind me I saw Charlie take off the condom, teasing my asshole with the tip of his cock. He didn't cum already, did he? But the condom was empty. He wants to fuck me bareback.
I bit hard into my lip as his cock slid inside me for a second time. It could feel the warmth of it. I could feel the grooves of his tip as it spread me open. And then I felt it. I was going to orgasm. It was just a small one, but enough to make me scream with pleasure.
Charlie shoved me onto my stomach and continued to fuck me hard. It hurt, but I could tell that he liked it, so I let him. Tears of pleasure and pain were streaking down my cheeks when Charlie rolled next to me on the bed.
He got on his back, spinning me onto his cock. I lay on my stomach with my feet in the air as I took his cock in my mouth. I could taste my ass, which only made me want more. I suck him wild and deep.
"Good girl, just like that. Work it down your throat. All the way down-- fuck. Just like that."
Charlie's cock was covered in spit and precum as I sucked. I slurped as much as I could. Then I sat up and got into a reverse cowgirl position.
"I want you to fuck my asshole, daddy," I said, grabbing his cock. He pushed it into my ass and I moaned.
He held my bare feet as I bounced up and down, gripping his balls with each sloppy thrust. I could tell that he was close to cumming. I spread my ass to make it easier to slide in and out of my asshole.
Charlie started to grunt and his breathing slowed.
I spun around, quickly locking my lips around his cock. Charlie stretched and grabbed the back of my head.
Cum shot into my mouth. Charlie's cock pulsed over and over, each time spraying the inside of my throat with warm goo. I moaned with pleasure and satisfaction. I kept my lips tight around his cock until I knew every drop was in my mouth.
"Show me," he gasped.
Slowly I parted my lips, sticking strings of cum stretching around my tongue. I let Charlie watch as I played with it, slurping and enjoying it. It was warm and thick as I swallowed, holding out my clean tongue to Charlie.
"Fuck," he whispered, laying back. "Wow."
I rolled over next to him and let my heart rate settle. "Wow." I turned and kissed him. "Be right back."
I grabbed my thong and went into the bathroom. My reflection is not what I expected. My hair was a mess, my mascara smeared and streaking. My boobs were bruised where Charlie had sucked at them. And my asshole was pink and raw.
I put myself together as best I could, slipping into my thong. I thought I heard Charlie talking as I came out of the bathroom.
"No, sorry I missed your call, I didn't see it. I am just in bed, what about you babe?" Charlie said. He held a finger to his lips as I walked over to the bed.
"Becca?" I mouthed.
Charlie nodded with a yes.
I crawled at the end of the bed, parting his bare legs and sitting between them, cross-legged. I grabbed his hand and put a finger to my mouth, then started to suck on it. Charlie pushed it down my throat.
His cock was soft when I grabbed it, and hard by the time I sat back and put it between the soles of my feet. I gripped his shaft with one hand, pushing the tip of his cock against my toes. Charlie leaned forward and squeezed my breasts.
"Mmhmm," he said into the phone.
I leaned down, sucking the tip of his cock while I held the shaft with my feet. Charlie stifled with a moan that he covered up as a cough.
Charlie sat up and positioned me so that I was on my back with my head barely hanging off the edge. He stood over me, dropping his balls into my mouth. One at a time, I took them into my mouth until his sack was fully in my cheeks. He tapped his cock against my face as I used my tongue to play with his balls.
Spit dripped over my face as he took out his balls and pushed his cock into my mouth. He put the phone on speaker, then set it on my stomach. Becca was in the middle of some story, but all I could focus on was Charlie.
With his hands free he held onto my books, slowing fucking my mouth. I could feel his cock bulging in my throat. I fought off the constant urge to gag as he deepthroated me. And then I felt his balls tense.
Cum sprayed over my lips, then my face, then my chest. Charlie drenched me with his cum, fighting off a moan as his cock pulsed over and over again. He was quick to grab his phone before any dripped onto it.
I sat up a sticky mess, my mouth gaping with surprise and excitement.
"Really?" I mouthed, cum stretching between my lips and hanging off my chin.
Charlie gave a happy shrug.
It took me longer to clean up this time. I was in the bathroom for a while, trying to fix my makeup and rebraid the bits of my hair that had come undone. I checked the time, it was really late now.
"I know I said this before," I said as I stepped out of the bathroom, "but I should probably go. I have to get up early--"
Charlie was fast asleep. I thought about staying, but I really needed to get home. I got dressed as quietly as I could, then stepped barefoot into the hallway.
