The Prologue
Some years ago, I injured my back. While it healed at the time, it has flared up once in a while, most recently a few months ago. The urgent care doctor suggested physical therapy so I found a local person who, to my surprise, did sessions not only in person but also on telehealth. I was skeptical at first, though--let's call her Annie--she did a great job with me via telehealth. From the first visit, I found her charming, a bit disarming, and, to be honest, a bit dorky in an endearing way. She's probably in her 30s, does the sessions from her bedroom so she can demonstrate the different techniques, often with her dog asleep on the bed, which has a few stuffies along with the pillows. She has a somewhat average build, not too small, not too large, with brown curly hair that is all over the place. She tends to where leggings and a loose button down top when we do our sessions. In a few of our sessions, I could see quite easily down the top of her shirt without even trying.
When we had our first session, I revealed to her that one of the things that seemed to have helped my back was being anally fisted the weekend before at a kink play party. She took this information in stride, dead-panning "Well, we won't be doing that, though it is good information." I commented that it must have been like getting a massage from the inside and she laughed. I appreciated her being candid that she had trouble doing her own exercises, and she understood that it was hard to develop a new habit. We did a number of sessions that gave me a good foundation for helping my back and completed the treatment for now. A part of me wanted to continue because I enjoyed my calls with her and I wondered what she was like when not working.
The App
A few weeks after we finished, I was scrolling through an alternative lifestyle dating app and who did I see but Annie! Her profile seemed like it was written for me, and I later learned that it more or less was written to catch my attention. Where I was mainly looking for a dominant feminine person, she was interested in exploring dominating a transfeminine person. She was interested in kink and somewhat new to it though her kinks seemed to line up more or less with mine. She was non-monogamous and wanted something the casual but consistent. And she not only worked nearby, she also lived not too far away. She had posted a few photos of her out and about with her dog and her partners and there were a few hidden photos that were only for matches. I bit my lip before swiping right and wondered if I had made a mistake though there was no way to turn back now.
A few days later, we matched, and I got to look at those hidden photos, one of which was a "down the shirt" shot and another was her in a cute bra and panty set wielding a strap on cock. I sent her a message: "Fancy meeting you here!"
She replied, "Indeed, I was pleasantly surprised to see you here. I have to admit, the hospital would probably not approve of this though I won't tell if you won't tell."
I smiled, again appreciating her candor replying, "I won't tell if you won't tell, either. It seems like we have some things in common. I liked the hidden photos. I'll be honest, the 'down the shirt' photo reminded me of some of our session."
"Oh, I am so glad you caught that!" she replied. "I'll admit that my shirts were a few buttons more open for our sessions."
I was gobsmacked. I was thinking and fantasizing about her from the first session and she was flirting with me, "I... I don't know what to say."
"Well, since we are being open and honest," she continued, "I found your stories on Literotica and I really enjoyed them. I also thought I recognized your profile photo even though it didn't show most of your face. My username is REDACTED. And I would really really like to meet... Simone."
I was floored and almost dropped my phone. I had enjoyed her comments on my stories--every one of my stories--and I had considered reaching out to REDACTED to let them know that I appreciated their words. I was also suddenly deeply self-conscious since my stories are rather intense. "Thank you for your comments, I really enjoyed them. I almost reached out to you but I was shy."
"I almost reached out to you, too," she replied, "but, you know, I wasn't 100% sure and I was a bit shy, too."
"Lest this seem too forward, the app says you are about a mile way. How about we grab a coffee soon?" I offered.
She sent a smiley emoji and replied, "'How Soon Is Now?' referencing the song from The Smiths. "What I mean is, I am done for the day and I am free for the evening... and the weekend, in fact. We can just cut to the chase. I am not interested in meeting anyone other than you on this app. And rather than coffee, how about an adult beverage?"
I imagine my mouth opened and closed and opened and closed a few times, and I finally replied, "I guess I was not too forward, then. Let's meet at that fancy cocktail place on the main street in an hour."
"Sounds purrfect, she replied, "and put on one of your... what do yo call them? wee cages?... and bring the keys for me. That would please me."
My cocklet stirred. I would have to stop thinking about this if I was going to be able to get the cage on before seeing her. I replied, "Yes...."
"Ma'am, is fine," she replied, catching my drift.
"Yes, Ma'am, I look forward to seeing you soon."
"You better!" she replied, then logged off of the app.
The Meeting
My mouth was a bit dry. I hopped into the shower to clean off and clear my head. I touched up my shaven public hair and was just barely able to get the cage on. I put on some skirted leggings and a casual feminine top that criss crossed over my chest. Underneath, I wore my favorite polka dot panty and bra set. On my feet, I wore my blue Maryjane flats with the strap across the top, My nails had been done recently so they were pretty. I chose some of my regular jewelry, let my hair dry in its natural blue bob, and I caught a car to the cocktail bar, I didn't want to think about driving.
I got there with about 10 minutes to spare and took a seat at the bar, near the back. It was late afternoon and the place was empty. I asked the bartender for some water and told her that I was waiting on a friend. When she came back, she had a drink, it turns out, my favorite, a rye Manhattan along with the water. She winked and walked away. I toyed with the keys on their chain, suddenly more nervous than I had been in a long time.
The weather was nice and the door was open. I saw a silhouette, shaggy hair on top, and knew it was Annie. I stood up and took her in for the first time in person. She wore a button-down summer dress that went to the knee and casual low heels, her toned legs bare. A few more extra buttons than usual were unbuttoned at the top of the dress. She had the familiar rings on her fingers and simple earrings. She saw me and smiled, giving a nod to the bartender and approaching me, "May I hug you, Simone?"
I swallowed, not used to hearing that name out loud, saying, "Yes, please, thank you for asking." She was a little shorter than me though not much, maybe 5'10", the heels bringing her to my height. I had explained that in my stories I was the height that I wish I was, 5'6", and not the 6' that I am.
She pressed her body to mine and held me close, whispering in my ear, saying, "You probably can relate, I have waited for this moment for a long time. Since our first session." And she broke the embrace, leaning on the barstool next to mine. "I think that you have something for me?"
I cocked my head and she looked at my hand, still playing with the keys. She had indeed read my stories! "Oh, yes, right here." I extended my hand and she shook her head, leaning over to give me a lovely view down the top of her dress, so familiar, though now so close. My shaking hands put the chain over her head--I only then noticed that she was not wearing her usual necklace, and the keys settled into her cleavage.
"Good girl," she said, and my clitty throbbed in its cage. The bartender brought over another beverage, a glass of red wine, and set it before Annie. She raised the glass and said, "Cheers!" We clinked glasses and I sipped my cocktail, looking into her eyes as one does when toasting and she sipped her wine. "I was glad when you suggested coming here. I am... somewhat of a regular... though I don't come here with my nesting partner. He has his own go to place."
I nodded, setting my drink down, resting my hand on the bar, saying, "So, just so you know, I am not just shy, I am neurodivergent, so, you know, a bit awkward sometimes."
She smiles, saying, "That is not surprising, to be honest. I won't take it personally if you are awkward. I won't even," air quotes "'punish you' for it because what fun is it if you are going to enjoy the punishment?"
I blushed some and took another sip of my drink, murmuring, "You have read all my stories, which was your favorite?"
She sipped her wine and said, "The one you will not doubt write about us will be my favorite."
I laughed, saying, "Well, if you insist, I will do my best and I hope to do justice to... whatever we do."