The First Date

Amateur

The First Date
Intro

To start, just a little bit about myself. I am a 34-year-old crossdresser that has been dressing for most of her life and has reached a certain breaking point of needing to transition. My stories are a way for me to deal with my dysphoria and provide me with guidance as I continue this journey. I’ve met folks that have inspired me to write these stories, so, for now, they are a work of fiction, but maybe one day a reality.
Chapter 1

We had been chatting back for forth for weeks, Sir, as I would refer to him, had been becoming for and more infatuated with me, I was beginning to really enjoy the attention. It started with leaving me Good Morning messages, and cute emojis through the day, and connecting with me on other social platforms. We really started out on Fetlife, I would like some of his pics and he would like some of mine, and leave amazing comments, driving me crazy. Being friends on Fetlife he was able to see all my pics, so I knew he knew what I looked like and he didn’t turn around and run, hehe. As we chatted more and more, our conversations grew more sexual and heated. We lived fairly far apart but who knows if we would ever meet.

A few messages later, Sir informed me that he would be at a conference not far from me, this sent shivers down my spine. As I read further he suggested that we potentially try and meet up and that I join him for a night or two. The immediate scenarios ran through my mind, an I available that weekend, how would this work, what would we do, what would I wear. 😉 nasty little thoughts ran through my mind. I told him that I would think about it and let him know when it got a little closer, maybe I could make one-night work.

Being a crossdresser, I have purged more times then I would like to admit, so I’m constantly rebuilding my wardrobe and coming up with my style. I told Sir that if I would attempt this I might need some new outfits, he told me that we might be able to arrange something, and I should get a wish list together…
Chapter 2

My hands trembled as I entered the code for the Amazon locker, as I retrieved the numerous boxes, I had a good idea of what I would be receiving. I had put together a modest wishlist on Amazon, mostly 2 outfits, one casual and one dressy for dinner. I rushed home as quick as I could to open the boxes and take inventory of everything.

To start, the casual outfit, which consisted of a pair of skinny distressed jeans, with some holes. A cute flower top and jacket completed the look. For the undergarments, a cute pair of pink hipster panties and a pink push-up bra to complete it. For footwear, a cute pair of wedge heels, in black with some straps, to give me some height and to show off my painted toes. Hopefully, to not appear too over the top, I wanted something I could easily pass in and show up wearing.

For the night, a sexy pinup style dress in dark red, with a flared skirt that raises just a little bit when you twirl. To cover the arms and shoulders just a little black crop cardigan. For underneath, dark red thong, a black waist cincher, and a black push-up bra and dark red shapewear with garters to hold up my black fishnets. For footwear, a sexy pair of shiny black retro Mary Jane heels, with some red accents.

There were some additional items, a shoulder-length black/brown wig, some D cup breast forms and clip-on earrings which would all help complete the look I was hoping to pull off. Sir was so nice to provide me with these items, I just hoped I would make him happy and be what he was looking for. I let Sit know that I received everything and that I would be ready for when the day of our date arrived.
Chapter 3

The day of the date I was a nervous wreck and took a shot or two to calm my nerves before starting to get ready. I had planned to do some initial prep work before leaving a fully changing into my casual outfit. First up was a full body shave, getting every last bit of hair from the top of my head down. Coating myself in some lotion and perfume, I was starting to at least smell like a gurl, hehe.

I started on my nails next, first pedicure, and painted my toenails a nice dark shade of red, almost the color of my dress. My glue on fingernails was next, not much going back after that, also done in a nice dark shade of red, similar to my toenails. I always smirk when painting my nails, I love it so much, hehe.

I threw on some quick boy clothes and grabbed my bags and jumped in the car before anyone saw me, once I got closer to the hotel I would find a spot to complete the transformation.
Chapter 4

The door to the unisex bathroom slowly opened as I checked to see if the coast was canlı bahis şirketleri clear, I set up shop in a stall and unpacked the rest of my clothes and items. I removed all my male clothes and started the process of becoming Alexis.

I slipped into my pink bra and inserted the D cup breast forms which had some weight to them. I pulled the flower T-shirt over my head and ran my hands down over my nicely sized rack. I then took out my chastity cage a locked my little clitty nice and tight, I was sure to then take to key, which was attached to a silver necklace and put it around my neck. I slid up my pink panties over my cage and the pulled up my skinny jeans over my painted toes.

Starting to finish the look, I started on my face, try to be as light as possible with my look. Some concealer, and foundation and blush to contour a little bit. Then some light eye shadow and eye liner, but of course some long fake eyelashes and dark mascara complete the eyes. I continue to outline my lips and fill them in with some light pink lipstick and of course some lip gloss. I look at myself in my hand mirror and smile, as the look is almost complete.

I start to finish things up, brush out my wig and secure it to my head and put on my clip-on earrings as they dangle against my neck. I then step into my wedge heels and secure the strap. I give myself a quick look over and quickly pack everything up into my bag, I also switch over from my wallet to my purse and female wallet. I throw on my light jacket and slowly listen to exit the stall, seems like the coast is clear. I give myself a look in the mirror and wash my hands, and start to apply a little more lip gloss. Suddenly I hear the door start to open, I freeze, an older man enters and immediately apologizes, I say not a problem, I was just finishing, hopefully in some kind of feminine voice. I finish my lip gloss and adjust my jacket and walk past him, swaying my ass a little as I go by him. He says, Miss have a great day, I say you too sweetie as the door closes.

I start the long walk back to my car, already getting some looks but nothing crazy that I haven’t gotten before. I get into my car and let Sir know that I am on my way, I text him a quick selfie so that he knows what to look for. I put on my sunglasses and start the drive to the hotel.
Chapter 5

My car pulled into the hotel parking lot and my hands were so sweaty, I hope that my Sirs expectations weren’t too crazy. My instructions were to wait for him in the lobby and he would be down to get me. I grabbed my suitcase and headed to the lobby. I could feel my ass sway with each step in my wedge heels and quickly found a spot to sit with my suitcase. I nervously waited as a couple of folks stared and some guys did a double look as they walked by, I played on my phone, took a couple more selfies and waited.

Sir then appeared, “Hello Alexis” he said to me and my spine tingled a little. I turned around and there he was walking towards me, I quickly stood and welcomed him, I daintily help out my hand with my wrist bent. He took it and kissed it, we then embraced for a quick hug. As he let me go he took my hand and made me do a quick little twirl so he could look me over, I yearned for his approval. He said, “Alexis, you have done an amazing job, I’m so happy with how you look, simply stunning.” I smiled from ear to ear and did a little courtesy and could feel myself start to blush. He said, “We must hurry if we are going to make our dinner reservation!” He took my hand and we rushed off to his hotel room.
Chapter 6

As we made our way to his room, he gave my butt a little pat and a rub, I let out a little girly yelp and smiled back at him and shook my ass a little in front of him. We made our way to his suite and he let me in and took my bag for me. I looked around and made myself comfortable and Sir poured me a drink. I sipped it as I looked out the window and caught my reflection in the mirror and smiled. I could see Sir behind me, and looked over my shoulder and smiled, he took a couple pictures of me and approached me from behind.

I then felt his hands on my hips and then he held me tight, his breath on the back of my neck. I pushed my butt back a little to run against him as he then proceeded to kiss my neck. I was in heaven, this was so far everything I would hope it would be, my clitty strained against its cage. Sir quickly stopped, undid the latch to my necklace/key and put it around his neck under his shirt and said that there would be time for that later and that I should get ready.

I took my bag and headed towards the bathroom, and started to get too work. I decided süperbahis to start over with my makeup, so I cleaned my face and undressed, the only thing I had on was my cage. I started to dress, put on my black push up bra and waist cincher and red shapewear. I put in my breast forms, and then put on my fishnet tights and attached them to the garters. I pulled up my black thong and sat to start my makeup.

I decided to go heavy with my makeup since it was a night dinner. Started with my concealer, heavy foundation and bronzer to contour my female lines. Dark eye shadow and liner and really long eyelashes completed the part, I must have been smiling the whole time, hehe. My lips came next, a dark shade of red to match my dress, outlined to perfection, big and plump, maybe DSLs? I stared over at my dress and smiled as I stepped into it and tingled a little when I zipped it close. To show more commitment I closed the zipper with another lock, the same key as my chastity device. I proceeded to redo/attach my wig and then stepped into my sexy Mary Jane heels, I looked in the mirror and admired the girl that looked back at me and my clitty strained again in its cage.

I opened the door and told Sir to keep his eyes closed, he did as I tried to strike some kind of sexy pose. I said he could open his eyes, he nearly jumped in surprise, and smiled from ear to ear, he gave a little whistle as he looked me over, I did a couple more poses, raised the edge of my dress a little. Sir then grabbed me and gave me a huge kiss, my first one with another man, I kissed him back and embraced him, and raised one my feet back. He grabbed my ass and squeezed a little, I have one surprise for you he said.

He motioned for me to get a box off the desk and to bring it over to him. I brought it over to him and held it out in my hands while he opened it. It was a modestly sized butt plug with a smooth flared base, he sat on the bed and motioned for me to lay over his lap. I laid on his lap and he slowly pulled down my thong and massaged some lube into my boi pussy. He then slowly started to slid the plug in/out, almost teasing me at times with it. He said, “I want to make sure you are ready for later, this with help in a few ways.” He smirked a little. He pushed it all the way in, slid my thing back up and gave me a little smack on my butt, “Time for dinner!” he said.

I grabbed my sweater and purse and we made our way to dinner, hand in hand, my heels clicking away as we walked, the butt plug making its presence known.
Chapter 7

As we rode down the elevator, he rubbed and fondled my ass and played with the edge of the plug through my panties, I squirmed in delight, my clitty strained in its cage. We made our way to the restaurant and our reserved private booth in the back, Sir motioned for me to slid into the booth next to him, I smoothed out my dress and sat down.

Sir did all the ordering and got us a bottle of wine, we toasted to start the night, I sipped my wine a left a cute lipstick mark on the glass, my sexy nails reflecting in the dim light against the glass. We looked at each other and he gave me a quick little kiss as his hand rested on my thigh, playing with my garters. He started to get his phone and smile a little, he was fidgeting with some app on his phone.

All of a sudden I felt this light vibration, I almost thought it was my phone, but then it got stronger, and stronger, pressing right against my prostate, he gave me this devilish grin. The vibration stopped. We started to eat dinner, my little vibrating plug was making me really horny, two can play this game I thought. I started to run his inner thigh and ran my nails across his crotch. I could feel him start to get hard, I gave it a little squeeze and bit my lip as I looked at him.

He opens the app again and I felt the plug start to vibrate, it was driving me crazy, I leaned my head back and bit my lip a little, I let out a tiny moan. The vibration stop and I removed my hand and smiled. We finished dinner, eager to get back to the rest of the activities. We started to make out in the booth, his hands all over me and my hands rubbing his crotch, he quickly paid the bill and he left the restaurant.

All the way back to the room, we could take our hands off each other, we would stop and make out a little, pushing my back up against every wall. He then left the plug on the rest of the way to the room, I could barely stand at times, I almost collapsed by the time we entered the room, and I collapsed onto the bed and the door closed and locked behind him, do not disturb the tag said.
Chapter 8

The vibration stopped again. I sat süperbahis güvenilir mi up on the edge of the bed, Sir proceeded to take more photos of me, I did a couple more poses, showed a little leg, bit my lip a little more. He then said, “Alexis, you were a naughty girl during dinner, someone needs to be punished,”. I nodded in agreement as he sat down next to me on the bed and pulled me over his lap. He then proceeded to spank me, with my bare ass exposed to him, 10 whacks he gave me, I moaned in pleasure. His hand made its way to my plug as he moved it in and out, he turned the vibration on again, I could feel my clitty start to leak a little, he caught some of it and made me suck it off his finger.

He instructed me to stand up and he moved behind me and ran his hands along my sides and down my hips, as he kissed my neck and bit my ear. I returned the favor my grinding my ass into his crotch and letting out a little moan. He then removed the keys from his neck and proceeded to unlock my dress and unzipped it and let it fall to the floor. I stepped out of it, he took more pictures and had me pose and had me get on the bed and do a couple more. I felt so sexy as he watched me the whole time, he was getting harder as we continued.

He motioned for me to come to the floor and kneel in front of him, I did and then pushed him onto the bed. I kneeled in front of him and quickly undid his pants and started to rub his crotch. I then took out his amazing cock and started to run it, I then took it deep into my mouth. Licking the shaft and running my tongue over the head, I could feel it reaching the back of my throat. I felt his strong hand on the back of my head, guiding me up and down on his cock, I was really going at his. The plug started to vibrate again and it was making me really horny.

I then straddled him across his waist, kissing him all over as his cock rubbed against my ass crack. “Sir, I want you so bad I moaned, please fuck me, fuck me now!” He threw me back on to the bed and continued undressing, he told me to get on my hands and knees with my ass in the air. I moved quickly and shook my ass at him, begging for it. He grabbed my ass and gave it a solid slap as he proceeded to take out the buzzing plug. I could feel his fingers probe my ass and he then added some more lube. He then slowly entered me, sliding in bit by bit, and then in and out until he had a good rhythm going.

Harder and harder he continued to fuck me, his balls slapping against my ass with each thrust. I was moaning in heaven as he continued, grabbing my shoulders and pulling him closer to him. He then stopped and put me on my back, looking up at him I smiled. The last key was used to let me out of my cage, my tiny clitty sprang to life, already leaking and yearning for release. He then proceeded to fuck me more, me on my back as he stared into my eyes. Him jerking me off with each thrust, I moaned with pleasure as he feveriously pounded me.

He then got on top of me in reverse and I took his cock into my mouth and sucked on his balls and licked his asshole front and back. All while he proceeded to suck my clitty and tiny balls, we were both moaning. I told him I was going to cum and he moved faster and I blew my load into his mouth, he quickly turned around and kissed me, giving me back all my own cum. I then got in front of him and started to rub him and suck him, tirelessly trying to get him to cum. He then moaned and shot his load all over me, all over my face as I quickly tried to catch it and swallow it all, he collapsed next to me, our members slightly touching each other, I cuddled up to him and laid my head on his chest.

I smiled as I fell asleep, feeling his hands on my body, slowly rubbing my thighs, the high was unreal. At some point, I got dressed in the nighty I brought. I also looked over and saw that the camera was still recording, I look at it and gave a little smirk and stopped it and went back to sleep.
Chapter 9

I woke before Sir did and cuddled my head towards his crotch and started to suck on his dick and he started to wake up. I was eager to stay but I really had to get going, so I went to shower quickly. Sir surprised me in the shower, we washed each other and he then proceeded to fuck me one more time, this time cumming in my ass, but locking it in with the plug, I felt like such a slut. We finished showering and I get dressed again in my casual outfit, Sir locking my clit back up but now keeping the key. After getting dressed and ready I gave him a long kiss goodbye and finished packing.

I told him I had a wonderful time and hopefully we could do it again, he agreed and I knew we would since he had the key. I smiled as I left and walked down the hall, I felt a little tingle as the plug vibrated and I smiled again.

All the way home I thought to myself how I needed more nights like that and to keep down this journey!

Until next time!

~Alexis~

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