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The next week or so felt like a dream. You worked pretty often so you got the chance to see Alyssa during most of the course of her training. She wasn’t always working with you, but there were several times that you were. You were never one to really jump into things without some caution, but Alyssa seemed to be everything you’d always wanted. She was gorgeous, adorable, very sweet, very funny, and really easy to have any sort of conversation with whether the two of you were talking about science, sex, or Star Wars. Then something happened that surprised you. Alyssa caught up with you after work one day before you could leave, a shy smile on her face.

“Hey so uh... you wanna go out sometime? Like on a date?”

It was a miracle that you didn’t fall over in surprise right there and then. Rarely had a girl this gorgeous ever seemed interested in you, but you never would have dreamed that one of them would actually ask you out themselves!

“Oh... uh... wow. I uh...”

“We don’t have to, if you don’t want to.”

“No, no! Sorry I was just... surprised. But yeah. I’d love to go out.”

She giggles a little at your response and looks thrilled as the two of you share numbers.

After that conversation you began going on dates. They started out as simple cute little things. The two of you went out to dinner and she walked you home. Then you offered to treat her the next time which she readily agreed to before ending your first date with a goodnight kiss, something that filled your soul with butterflies.

It wasn’t until the third date where things took a turn for the very interesting...

You had treated Alyssa for the third date, and by the time you drove her home it was quite clear that you were both reluctant to say goodbye. After making a little small talk you made out in the car for a few minutes before she paused you and in the shyest voice you’d ever heard the usually confident girl use, she said, “Would you like to come inside?” With a gentle nod, you agreed.

Inside the apartment the two of you had another glass of wine on top of what you’d had a dinner and continued to talk. Before too long the smiling girl took your hand and pulled you to the bedroom. In the room she sat you down in a chair and from the look on your face you could tell she was nervous.

“You okay? You asked softly. “We don’t have to do th--.”

“No, it’s okay. That’s not it. I uh... I wanted to share something with you. To be honest, I was going to keep it a secret for as long as I could... but I wanted to be honest with you.”

You gave her a warm smile, “You can share anything with me. I won’t judge you Alyssa.”

She still looks reluctant to proceed, but your words make her smile. “You promise?”

“I promise.” You utter out.

“Okay. Heh... well I guess I’ll just show you.” To your surprise, Alyssa begins to fiddle with her belt before taking it off completely. Then she undoes her jeans and pulls them down. You’re confused, and then shocked. Instead of the sexy lacy panties you were expecting, Alyssa was wearing something bright white with a plastic-y material and a cute little beach scene on the crotch of it. Was that a... diaper?

Alyssa looked a little red faced, but she rushed to explain. “I know, I know... it’s super weird. I’m sorry. When I was little I was in a car accident and it left some of my muscles damaged and well... I need to wear these at all times or I’ll... have an accident on myself.” The poor girl looked a little disgusted with herself. “I’m sorry... I know it’s weird, but I thought it better to tell you now than to try to lie and keep it a secret.”

She looked like she was starting to get a little emotional, so you quickly did the one thing you knew you had to do.

You got up and moved next to her, and kissed her deeply with a hand on her waist. The two of you passionately made out for a minute or so, Alyssa’s little cute diaper totally on display now that her pants were around her ankles. When you finally pulled away you were both smiling at each other, Alyssa a little bit teary eyed. You finally spoke up, “Girl. It’s okay. I promise. I said I wouldn’t judge you, and I’m not. And... If I’m being honest... I think it’s kinda cute.”

You reached down and gently placed a hand on her butt, the diaper crinkling as you did so, making Alyssa blush bright red. The smile on her face though matched your own, and she leaned in and kissed you again as the two of you moved towards the bed.
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This story was written by Zander Chesney

You can find more of his content here :

https://zanderchesneyoriginals.tumblr.com/

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