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 rundown.

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? ?

Haha. Thank you. You’re absolutely beautiful. Oh and yes I am. Promise??

Good ?

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? ?

Sure I can do today, How about CaféDenated?

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 trendy 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 gonna be rainbows and unicorns.

Leyla pulled up in a huge 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 begin 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 find 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.

“LEYLA!” My Mom screamed at her and playfully hit her.

“What? I told you I’d love to make him my personal Gimp.”

“He is fresh out of High School!”

“So what? He’s legal. Your telling me these 60/70/80 year old men can be fucking 18 year olds females. But my 30 year old self can’t spit roast this 19 year smart ass?”

“You’re 37 and you know it!”

“Okay and I fuck like a 25 year old. So let’s meet in the middle.” Laughs Leyla.

“Maths is not a good look for you.” Mom tells her.

“Nope, but my strap-on is.” Answers Leyla and they both laugh.

Even though I had no interest in becoming Leyla’s personal Gimp, I’d be lying if I didn’t say her wanting to use me didn’t have me straining in my cage. The Fusion Deluxe is a solid unit that is completely restrictive. The attempt at an erection basically feels like a pulsating throb. No pain, just the throbbing sensation and me leaking in my shorts.

“I just gotta fill up quickly.” Leyla says pulling into a Gas Station.

“You get better miles per gallon in a less gargantuan vehicle.” Replies my Mom.

“But how would that help me overcompensate for my penis envy?”

“Thought that’s why you have a 14″ strap-on?” I scoff.

“Keep it up kid. I’ll remember all this when I have you ball gagged and hogtied in my dungeon.” Leyla growls with a glare as she steps out the Hummer.

“Why do you let her talk to me like that?” I asked my mom.

“You give as good as you get.”

“Yeah but still. It’s a tad much, no?”

“Well, she means it. Besides that plug she just gave you isn’t exactly cheap!”

“Huh?”

“It’s like a Three grand plug.”

“You’re shitting me?”

“Nope. Best on the market. It heats up and the vibrating pulses have small electrical surges that are so intense the prostate is guaranteed to drain its load.”

Fuck. I thought to myself. Even though I had no desire to stick it inside me, it definitely sounded interesting.

“I’ll probably just sell it.” I mumbled.

“Your gift, your choice. A stupid choice. But it’s still your choice.”

A few minutes later Leyla is back in the Hummer and we’re pulling out of the Gas Station.

“So, Patty. You got him a fusion, huh?”

“It’s the safest and most secure one on the market.”

“Pricey though. Especially if he’s just gonna keep taking it off every 5 minutes to knock one out.”

“He isn’t.” Mom answered sternly.

“Honor system never works, Patty. You know that.”

Then there was silence. The silence grew, and honestly it became deafening, I could hear the wheels turning in Leyla’s head.

“WAIT! YOU’RE ACTUALLY HE’S KEYHOLDER?” She screams in disbelief.

“It’s not like that!” I yelled out.

“NO FUCKING SHIT, DICKHEAD. Of course it’s not gonna be how she is with clients!” Leyla fire back. “Patty! How come you didn’t tell me? This is my literal dream!”

“Your dream is for me to be locked and my mom to hold the key?”

“No, dumbass. My dream is for every male of legal age on the planet to be in chastity. You turn 18 and Happy Birthday. Here’s a card and your present…a cage and welcome to your adult life in chastity.”

“I remember it being a tad more extreme than that.” My mom scoffs.

“I mean yeah, that’s just the holiday card version.”

“What’s the ‘Extreme’ version?” I asked.

“18th birthday you’re booked to get a PA piercing and a circumcision. Mandatory! After that you have weekly visits with your Doctor to check your healing process and take your measurements. Once the doc signs off. You’re fitted with a cock cage that has a titanium PA locking ring. The O ring has a metal fixing plate that allows a metallic waistband to wrap around you and make sure you’re 100% secure.”

“That would never work. People’s weight fluctuates at all times.” I laughed at her. Thinking I had destroyed her misandrist dreams.

“Obviously you’d have monthly check ins, with a nurse, one to perform your monthly milking. Two to check you’re cleaning correctly and that the cage and band is still secure. The waistband can be loosened or tightened up to an inch or two to allow for weight gain and loss. Anything more that the two inches you pay a fine and are put on a diet or booked into a fitness center to maintain a safe BMI. See my plan would also tackle the obesity crisis in this country.”

“So what, girlfriends would have to ask their boyfriends mothers to have access to the keys if they wanted to get physical?”

“Nope! Girlfriends don’t get keys! The doctors do.”

“What? I don’t figure out.”

“Traditional sex would be purely for married couples. And only for reproductive purposes. You make an appointment with the Doctor and when the wife is ovulating then the cage can be removed for a 4 day period to allow for procreation. After that, Cage goes back on. If you fail to get pregnant, try again next month.”

“This sounds horrific?” I gasp.

“It solves every issue regardless of political belief. Against teenage pregnancies, this fixed that. Women want full autonomy control. Does that!”

“Just not for the man?” I snap.

“You have full control. You decide who you date, if you want to get married or not. Just not the ability to jerk off when you feel like it.”

“Just genital mutilation.”

“Hey if men could be trusted, we wouldn’t need to.”

“How can you have an intimate relationship? With someone without sex?”

“STRAP-ONS! The woman gets to pick what dildo she wants or needs to be truly fulfilled. It makes marriages stronger. Because trust is involved and the guy will actively be working to make her happy and most importantly make her cum.”

“You’re psychotic, Leyla.” I tell her, truly horrified.

“Men have had centuries doing what they want. So let the women have a few hundred years and then put it to a Referendum.”

“I’d rather not, thanks.”

‘Says the dude in a cage.” She laughs.

I stayed quiet. I was honestly shocked and sickened by Leyla’s words. But I would be lying if I said my shorts weren’t soaked through. I just prayed they would dry in time for my date.

The rest of the journey was uneventful. I sat in silence thinking over and over about Leyla’s vision for the future, while my mom and her chatted about generic shit. I was engrossed in my own thoughts that I didn’t even notice Leyla had parked up.

“Yo Beta Boi. Gotta get out now.” Leyla snickered.

“Leyla.” My mom says, disappointingly.

“Oh come on, Patty. I’m only playing.” She giggled.

Getting out of the car I check my watch. I got 20 minutes. I tell myself.

“Thanks for the lift, Leyla. Mom, I’ll see you at home.” I say giving an awkward nod and wave, as I turn and start to journey to CafèDenated.

Leyla shouts something at me. But I can barely make it out. Something about fun and not too much. I shrug it off and carry on. I have a date and I’m not going to be late.

I arrive at the cafè first, grab a nice table in the corner and start to wait for Jessie. After a few minutes boredom sets in so I pull out my phone and begin scrolling through my socials, occasionally looking up to see if Jessie had arrived yet, when finally I see her walk through the door.

“Hey.” I say as I stand up to greet her.

“Hmmm…yeah. You’re definitely over 6 feet.” She laughs.

“I did tell you I was.” I laugh a little relieved.

“Yeah you did, but guys do tend to lie, especially when measurements are involved.” She says with a smirk as she takes her seat.

“Fair enough.” Is all I can muster, as I take my seat opposite her. “So err, why the 6 foot rule? Your like, barely 5 foot?”

“I’m 5,1 and half. Thank you very much.” She quips. “I like to wear heels. Like 6 inch heels, and I like looking up at my man.”

“Yeah?”

“Yeah! The only time I wanna look down at a man is when I’m on top.” She says with a wink.

I begin to go red and try to laugh off her statement. But her opinion had its desired effect to put me on the back foot…and to have my cock twitching in it’s cage.

“Let me buy you a drink. What would you like?” I asked.

“Coffee. Cream and two sugars.”

“Sure thing.”

Buying the coffee allowed me time to recompose myself. But as I walk back to the table I feel Jessie staring at me like a piece of meat.

“Thank you.” She says as I hand her her coffee. “So tell me about yourself?”

“Sure. So I’m 18. I start University in Fall. I work at a Pizza Parlour. I like sports, gaming, and erm, yeah. That’s about it. How about you?”

“I’m 23. I work in…well let’s say ‘entertainment’. I love movies. I love to go dancing. Hockey games are a must and museums bore the fuck out of me.”

“Is the age gap okay for you?” I ask.

“Yeah. You look older so it’s not too bad. Maybe grow a beard?” She says jokingly.

“I’ll try.” I laugh.

We were talking for about a half hour. She kept throwing innuendos my way. She was definitely playful. Then she hit me with the bombshell…

“So what are you into?” Jessie asks seductively as she sips her coffee.

“Huh?”

“What gets you going, what cooks your Goose?”

“Erm…I don’t know.” I mumbled completely caught off guard.

“Come on. Everyone is into something. Feet…dress up…role play…spanking. What was the last porno you watched?”

I just laughed nervously.

“No need to be embarrassed.” She said rather blase.

“Okay, well you tell me what you’re into Then.” I sputtered.

“Hmm…Last thing I came too was a dude pumping his meat. Massive schlong. I almost squirted. Before Tumblr became shit. There was this dude…Girthy Encounters. That was probably my go to.”

“Oh…right.” I mumbled, deflated.

“Yeah! There is just something about seeing a massive cock pumping away, get my juices flowing!” She giggled.

“Um, Jessie. Look, I’ll be honest. If you’re looking for a…massive schlong…that’s not, that’s not me.”

“FUCK NO! Just because I like to see things, doesn’t mean I want to experience them.”

“Oh, okay. Cool.” I said feeling pathetic and extremely inadequate.

“So what about you? What are you into?” Asked Jessie once more.

I paused with a slight hesitancy. Just say it! I told myself. She’s too open to not know. She has to be someone my mom sent my way.

“Erm, well I can’t believe I’m actually going to say it. But Chastity.”

“Oooh. Really?”

“Erm, yeah. Like, I’m quite new to it. But I can’t imagine I’ll ever get bored or sick if it.”

“Are you wearing it right now?”

“Yup.” I nod.

“You’re a kinky fucker, aren’t ya?”

“I wouldn’t go that far. More of a regulator.”

“You don’t have a weird porno obsession do you?”

“No. Of course not.” I lied.

“So why chastity?”

I told her all about my high college experience. The bullying, the pictures and the imprint and urges it had left on me.

“Fucking Internet. Am I right?”

“Huh?” I asked slightly caught off guard.

“No internet, and you have no issues growing up. You may even grow up completely vanilla. I mean unless your mom had gimps round cleaning the house.”

“Haha. No. No she did not.”

“So you want a girlfriend or a keyholder?”

“Erm, can a girlfriend not be both?”

“It’s possible, but being a keyholder is a lot of responsibility. There’s teasing. Training. Delivering.”

“Delivering?” I probed

“Yeah. Delivering that anticipated release. No point being locked just to end in an unenthusiastic nut.”

“Fuck.” I mumble. As my caged cock begins to jiggle in my shorts.

“So, sorry to tease you and leave. But I’ve actually gotta bounce.” Jess says.

“Yeah sure. No worries. It was great to meet you.”

“You too.”

We have a hug and out the door she goes. Leaving me with a wet patch in my shorts.

I had several hours before my date with Sara so I took the opportunity to go see a movie. The cinema was empty and it helped killed a few hours.

I got out of there and headed to meet Sara. I’ll save you the details on that one. Our personalities just clashed. It was awkward as hell, neither one of us really spoke. Just kind of walked together through the park and then was like “okay, bye” complete waste of time. I caught the train home and headed home.

When I got in Mom was sitting watching t.v.

“How was your dates?” She asked, pausing the t.v.

“Erm yeah, one was promising the other not too much.”

“It happens.” She says unpausing the t.v.

“Yeah, well I’m a little wiped. Imma head to bed.”

“All good. Goodnight. Oh and I left something on your dresser for you.”

“My key?”

“Nope!” She laughed back.

Can you guess what was waiting for me on my dresser? Any ideas? It was a bottle of Anal Lube. I had completely forgot about the three grand plug in my backpack.

Now I’m not gonna lie, I was horny and I’m not gonna pretend that the wondered didn’t occur to me. But honestly I just opened my top drawer and knocked the bottle in and dropped the plug and shut the drawer. It was not going inside me.

Tuesday

Same morning routine, I met Alisson at the train station. She was really gorgeous. Indian decent, slim, with perky tits. She had a bob haircut, white blouse black mini skirt and knee high leather boots.

We had a coffee and a croissant each, while we chatted. She told me she moved to City a few years back and although she had made loads of friends, finding a partner had proved tricky. I had a nice time, but there wasn’t really much of a spark if I’m honest, despite how beautiful she is.

Wednesday

Catherine messaged to say she had Covid so we had to reschedule. I exchanged some messages with Jessie. But that’s about it. So lets fast forward to Thursday and my date with Paige.

Thursday

Usual shit happened woke up went to etc etc. So lets jump straight into me at work waiting for Paige. I’m in the back rolling dough and action.

Alan my boss came over to tell Paige had arrived everybody’s reaction was different. BB looked pissed, like a woman scorned, Daryl was almost jumping for joy, and Sasha, well Sasha had a look of a disapproving mother. But I was more concerned about meeting Paige in the flesh.

Her picture did not do her justice. She was absolutely beautiful. She has raven hair, some tattoos, skin whiter than snow white, about 5’5 slim create with a great rack and ass to match. From her tinder pic, I would not have recognised her.