Hey guys(maybe some Gals too) welcome back. Wow it's been a minute huh? Okay so let's see where we leave things? Oh yeah, I had just started going on dates. Do you wanna hear about them? I mean there were A LOT! Yeah maybe that's too much. Okay I'll tell you about some and maybe see who you think I end up with. So let's do a quick recap.
Monday
I woke up with those messages and I started messaging back and quickly began to organize some dates.
My first organized date was with this stunner called Jessie. Jessie is a natural redhead like 5,1 slim but busty. We had agreed to meet at a coffee shop. Wait. Wanna read the DM's so I don't have to explain? Okay cool.
Jessie
Hey, I'm Jessie. You're really cute. BUT!!! Are you REALLY 6ft? π€
Haha. Thank you. You're absolutely gorgeous. Oh and yes I am. Promiseπ€π»
Good π
So I passed the height test, now what?
Now we meet in person
Okay where/when is good for you?
Anywhere in the city is fine. Mon-Thur only though.
Ooookay, I'm free most of the week.
How about today? π
Sure I can do today, How about CafΓ©Denated?
That works. I can do 12-2pm?
Brilliant. See you then.
Yes you will
Then there was Sara who wanted to walk in the park that evening. Her message was generic. Then there was Alison who wanted to meet on Tuesday, again plain and simple message as well. Catherine on Wednesday. Then there was Paige who was available to meet Thursday, and she seemed feisty.
Paige
Me you Thursday. Who says no?
Definitely not me. Lol
Sweet. You like pizza?
Is the pope a Catholic?
You know Joeys on Main?
Haha. I actually work there.
Excellent. You can get us a discount. How does lunch sound?
I'll tell my boss I need an extended lunch break.
Good. See you then XoXo
See you then
So there it was. With several dates booked and my first I'm a few hours I jumped out of bed and walked over to my mirror dropping my bottoms to gaze at my caged penis. I had never been popular and now I am, thanks to this. I stood there dreaming away stroking my balls at the possibilities.
"Hey, Leyla is swinging by to take me to work. If you want a lift into the City make sure you're ready in 10!" My mom called out, snapping me back to reality.
Now normally I'd rather have my balls whipped (which I'm sure Leyla would personally love to do) than be stuck in a car with her. But seeing as I had a date in a few hours and several more on the way, I was prepared to bite the bullet for the financial savings.
"Actually a lift would be great, thanks. I'm coming right now."
"Yeah we both know that's not true." Mom laughed back.
"Sooo not appropriate, Mom!"
To be fair to her, that's just my mom's sense of humor. Dark. But I guess when you're a pro domme your personality traits are hardly going to be rainbows and unicorns.
Leyla pulled up in a massive white Hummer. Winds down her window and gives me a look and then swivels her gaze to my mom.
"What am I, a taxi service?" Leyla yells.
"You really gonna make me take the train, Leyla?"
"No she is not." Answers my mom
"Depends."
"On?" I ask.
"You still in that piece of shit cage? I don't let unlocked guys in my motor!"
"No, I'm not in the piece of shit cage anymore. But...I am currently locked...so I can have a lift right?"
"Flash us your cage and I'll give you a lift!" Leyla smirks, licking her teeth.
Now a week ago I would've been too embarrassed. But seeing as this bad boy has me almost 30 women interested I'm not even slightly bothered. So with my mom's back turned, I unbuttoned my jeans and flashed Leyla my cage.
"Oooh. Mommy got you an upgrade I see." Laughs Leyla. "Get in."
We get in the car, my mom sits upfront and I jump into the back and start responding to my DMs.
"So how'd you get him to change his mind?" Leyla asks my mom.
"I'll tell you later." My mom says.
"You better!"
We're not driving five minutes when my peripheral vision detects something. I look up and see Leyla's eyes in the rear view mirror glaring at me.
"Shouldn't you be focusing on the road?"
"Patty. Open that glove box and hand me that box." Asks Leyla, completely ignoring me.
As my mom hands it to her, Leyla tosses back in my direction.
"Was a gift from a client, but consider it a late Graduation present, kid."
I opened the box to discover a metallic silver butt plug. Titanium Bluetooth Vibrating Butt Plug
"Erm, thanks, Leyla. But that's a one way street for me." I told her.
"Why are men the biggest pussies?" Leyla asks my mom as they both giggle.
"That's the best on the market and isn't exactly cheap. Don't be ungrateful. Besides, it'll revolutionize your orgasms."
"I don't put shit in my ass."
"Yeah that's not gonna last long with chastity. You'll be bouncing on a dildo in no time."
"No I won't."
"Oh you will. And cumming from the bussy is going to fuck your mind up!"
"Bussy?" I asked, confused.
"Boi pussy." She laughed.
"Leyla, can you stop?" My Mom interjected. She then swivels in her seat and looks at me. "Look, there is nothing wrong with anal stimulation and it CANNOT make you gay."
"I'm just not interested." I told them.
"And that is completely fine." Mom answers.
"Anal does keep you healthy though." Leyla snapped.
"So does cumming." I snap back.
"So does cumming..." Leyla mimics. "Listen, WebMD. Cumming may clean the pipes but a prostate massage is what keeps the orgasms coming..."
I didn't respond because I didn't know if she was serious. It sounded legit. But I'll have to Google it later.
"...Besides, if you don't start practicing soon, how will you be able to take my 14 inch strap-on up your bussy." Leyla laughs.