I’m a regular at a local cafe where I like to work sometimes. Every Friday this woman comes in around the same time as me and sits across from me. She is older than me and dressed in business attire, like she is a lawyer. She has long black hair and wears glasses. I am not usually into older women, but something about her struck me. She is always dressed nice and generally seems a bit intimidating.

On slow days it is sometimes just the two of us after the morning rush, but I’ve always been too shy to introduce myself. Today was one of those days and she walked in as I was waiting for my order. After she ordered, she waited right next to me. This is my chance. Before I could think of something to say the barista handed her a pastry. She walked to her table and I noticed she was wearing a strange necklace with a key on it. The rest of the morning I went back to my routine. Still too shy to say something. However, I couldn’t stop thinking about the necklace. Why a key? I accidentally glanced at it resting on her chest and looked up to find her eyes pointed right at me. I immediately went back to my screen and tried to pretend nothing happened.

That night I got nervous I may have come off like a creep staring at her. Then I started thinking again about that key. Was it a kink thing? I am probably reading way too into it.

The next day I went back to the cafe in the hopes she might be there. I sat down at the table and out of nowhere she walks in and sits at my table across from me. This time she had on a tight black shirt and leather pants. The necklace was resting right above her exposed cleavage.

“I’ve seen you in here a lot, my name is Cass” “I’m Dave. Sorry about yester-”

“I saw you looking at me”

“Sorry, I was just looking at your necklace. I’ve never seen one like that before” She laughs

“Do you want to know what it unlocks?”

“Yeah, I guess I do”

She gives me a look and smirks. “Well it’s nice to meet you but I need to get going. See you around”

She gets up and gives me another look as she leaves. She left a paper on the table. It says ‘8pm tonight’ and an address.

8PM comes around and I feel nervous. I am at the address she gave me and knock on the door. She opens it and is wearing the same outfit, but no necklace.

“I wasn’t sure you’d actually show. You must really be curious”

We go inside and she gets me a glass of wine. We sit on the couch and talk a bit. I find out she works in finance and probably makes much more than me. She says that she usually dates younger men like me and asks what I think of her. At this point I am sweating a bit. “I think you are beautiful” “Well I could tell that by the way you’d always be looking at me. You know yesterday wasn’t the only time I caught you right?” My heart sank. I didn’t even realize I was being that noticeable. She moves close to me and notices some movement in my pants.

“Do you want to see what the key goes to?” She whispers into my ear.

She walks into another room and comes back with the necklace and a small metal object. “Do you know what this is?”

She is holding a small cage. It’s a male chastity device. “I want you to go in the bathroom and put this on for me. Then lock it up with this” She holds out a small lock with the necklace inserted. “Will you do that for me?” I don’t know if it was the wine or my excitement but I nodded without question and did as she asked.

My dick was already a bit hard from all the excitement and it took me a minute to get it on. I noticed the cage was tight against my partially flaccid cock and I started getting nervous. She knocks on the door “Do you need help?” Before I can reply she walks in and presses two ice cubes up to my balls. In one move she pushes the cage snug and closes the lock, taking the necklace into her hand. “There you go. I love how you look locked up” She moves closer and holds me. She whispers into my ear “do you want to be mine?” without a second thought I replied “yes”

She zips up my pants, walks me to the door and we say our goodbyes. I can’t believe what just happened.