(Long time lurker and first time poster. Please be gentle writing was never my strongest.)

It was a chilly Sunday morning when I decided that it would be one of my few last times, I could wear a full crossdressing outfit while mountain biking. Top comprised of a camo pink sports bra, misty merlot seamless long sleeve top and a dark heather gray BBL style jacket. Bottoms were a grey seamless thong and melanite fleece leggings. After getting dressed I was nervous about heading out biking actually dressed. Having second thoughts if I should just scrap the idea. After convincing myself that little to no one would be out on the trail with it being just below freezing.

Arriving at the trail head and the parking lot was empty. This made me feel better about being dressed. Took another photo in the driver’s seat before grabbing my helmet and gloves. Before exiting the car did a double check to validate that no one was in the parking lot. Quickly unloaded bike, started Garmin watch to track the ride. As I got onto the bike finding my riding position. I heard a car pull into the parking lot. Trails were empty and I got a good 10 miles in. On the return trail I could view the parking lot from elevation. Only saw several cars and only one next to mine. Praying that the car would be empty as I approached. Thankfully the car was. However, I had a note under my windshield wiper. Before removing the note and reading it needed to load up bike and get out of view. Once in the car I open the note.

Hi Joey,

Long time since we last saw each other. I saw you ride away and you looked cute in your outfit. Here is my number.

XOXO Ali

The handwriting looked familiar but none of the vehicles did. I had only known of one Ali and that as a long time ago and more like a friend of a friend who flirted with me when the group went out the bars. I put the note aside and proceeded to head on home to shower and change. Once showered and photos uploaded to reddit I took a look again at the note. Figuring what the hell and gave Ali a text.

Hey Ali. Its Joey. 

It felt like ages before I received a reply back Finally heard the ding from the phone.

Hey Cutie! What are you doing for lunch? I would like to meet for some lunch at the taco truck downtown to catch up

.….I guess… I don’t have anything going on today.

Great! See you at 12.

My face was flush and heart was racing a million miles an hour. Thought why would it be today someone saw? Why would they even put a not on my car? Why me?

Getting dressed in my male clothes remembering that I don’t have any male underwear. Tossed them all out years ago and went to panties for daily wear. Picked out a black thong, go to light brown cargo pants and a graphic tee. Boy was I nervous wreck and thought about bailing. I was hungry and that place does have damn good tacos. Worst-case scenario I would still come out ahead with tacos.  

Arrived at the parking lot 10min till noon. Shut off the car and started to walk up to the area the food truck was at. Ali saw me walking up and waved me over. As I approached, I saw her in bright blue leggings and a white racerback top. She came up and gave me a big hug.

Ali: It’s been forever! How have you been?

Me: I’ve been good. Just been working a lot. You?

Ali: Just moved back here. Just moved back here since I can work remote and to help my parents out.

Me: That must have been a great offer to move away.

Ali: I did. A place Texas had a fast track to a partner that was extremely hard to pass up. Do you still work for the family business?

Me: I am. Grandparents decided to retire and I own the store now.

Ali: Sweet I bet that feels good being the big boss now.

Me: Yeah, it’s also super stressful at times. (Hearing my stomach rumbling.) Think we should get some food?

We walked up to the window and place our order. After receiving the order, she told me to follow her. I wasn’t going to complain it would allow me to have a good look at her ass. We ended up at a table near the back of the court away from anyone. I took the seat that faced the way we came. She took the seat across form me and looked at me and smiled and started to eat. Thinking she wouldn’t being up this morning I kept eating. Just as I took another bite of the taco.

Ali: So,I have a question for you and you can be honest with me and tell the truth. You can decline to answer the question and we can finish lunch and go our separate ways. Were you wearing women’s clothing this morning when you headed off down the trail?

I nearly choked on the taco as she finished asking the question. Looking wide eyed at her. She trying to hide a smile. Taking a drink of water,thinking if I should just come clean. She placed her hand on mine. This made me feel reassured that I could come clean to someone in real life and not just some random person online.  Looking around to make sure no one was in earshot. 

Me: Yes…

Ali: Yes, to what? She grabs my hand harder and leaning in.

If I could look at my face, it would probably be red as a lobster.

Me: Yes, not a good answer? Are you looking for a detailed answer?

Ali: I am.

Me: Ugh. Um yes, I was wearing women’s clothing this morning. Anything else?

Looking up I saw that her eyes had widened and they looked full of joy. She had grin like a Cheshire cat.

Ali: Why don’t we finish eating and then head to your place.

Me: Ummm. I guess we can. Could we not do it another day it’s a bit of a mess. (Trying my best to avoid having her come over.)

Ali: (stern voice) No, doesn’t matter if it’s a mess or not.

Me: Okay. Just follow me when we leave.

We finished eating and headed to the cars. She had her arm around my waist as we walked. She was giggling as we walked and I kept asking her what’s up. Same answer each time, nothing. She followed me to my house and on the short drive I was a nervous wreck. Why did I come clean to her?

Once at my house we walked through the front door to the living room. Telling her she can have a seat anywhere and if she wanted something to drink? She took a seat on the love seat and said she would have a glass of red wine. I walked into the kitchen grabbing the already reopening the bottle of wine from last night. Pouring her a glass and myself one that I promptly drank. Refilled my glass and walked back into the living room with both glasses in hand. As I handed her the glass, she asked me to take the seat next to her. Doing as I was told taking the seat next to her. She turned sideways with her back against the armrest and threw her legs across my lap. Pinning me down so I couldn’t get up.

Ali: So, Joey, was it just leggings and a jacket you wore?

Feeling my heart in my throat. Looking around the room to avoid eye contact.

Me: In all honesty no. I had on a thong, bra and a top under that jacket. I could hear Ali giggle and she moved her right of her leg back and forth across my lap.

Ali: So, are you wearing a thong now?

Me: Do I have to answer that?

Ali: No, not at this time. But you will show me.

After that remake it made me look at her. She had that same playful smile and her eyes were different from before. She had the look of a predator who finally found its prey.

Me: What!

Ali: You heard me correctly. How long have you been wearing them?

Me: For the last few years. I have found them to be more comfortable…

Ali: Oh! I always had an inclination you had something hidden. I’ve got to go powder my nose where is it at?

Me: Down the hall and to the right.

She handed me her glass to hold and then she slowly removed both legs. Feeling the bulge in my pants as she did. When she got up, she looked over her shoulder and gave me a wink. As heard her approach the bathroom I realized that the cage was still in there. I tried to yell for her to stop and use the other bathroom. Nothing came out of my mouth. Fear sat in. She is going to see it and think I’m some kind of deviant.

I hear the door open and then her walking back to the living room. She rounds the corner leaning against the wall with a hand behind her back.

Ali: Anything else you would like to add?

Hoping that maybe I had a towel hiding the cage and she didn’t see it.          

Me: I told you everything. (I knew that was lie. Just didn’t want to scare her off)       

Ali:I know you didn’t. I found something in the bathroom.

Moving that hidden hand to the front and in that hand was my chastity cage.

Ali: I know what this is.

I was petrified. A million thoughts running through my head and how does she know about chastity cages. Should I just sell the store and move to another country?

Ali: I need you to stand up now and keep holding those glasses. 

Me: Ali, do we need to do this? 

Ali: Yes, we do. For years before moving, I have tired flirting with you and you never asked me out. I think the least you can do it follow some simple instructions. Now, stand and I don’t like to repeat myself.

Me: Okay, with an eye roll. 

Ali: Fist off you will call me ma’am and don’t eye roll me.  Chop-chop I don’t have all day for you to get your ass up.

Me: Yes, ma’am.

I proceed to stand the best I could with holding two glasses. Once up I looked at her, seeing her short athletic frame standing in front of me holding my cage. Maybe I was in a dream. This couldn’t be real. Should be waking up at any time then.

She walked towards me one foot in front of the other. Swaying the hips as she does. My mouth drops. This might not be a dream after all. As she arrived, she looked down. I had a very noticeable wet spot. Then she bites her lower lip. That was almost enough to make me cum. With her free hand she grabbed her glass and took a sip and handed it back to me.           

Ali: I can tell you are liking this and I am liking this. I would like to continue with this if you agree.

Me: Ma’am I would like to continue this. 

Ali: I’m glad you do. What I’m going to do next let it happen. Listen to my instructions and follow them. Firstly, you are going to lose the pants. 

Me: Yes,ma’am. May I put the glasses down to do so?

Ali: Keep holding them. I will assist you.

She places the cage on the coffee table and stands in front of me. Lifting my shirt and undoing the belt. Pulling it from all the loops and lets it drop to the floor. Next is the button and fly. Once those were undone the pants also fell to the floor around my legs. She assisted me stepping out of them. Now I was standing with a shit and my thong on display. Taking a lap around me, inspecting her new toy. Tracing her finger along the band of the thong. She stops behind me. Traces the outline of the T part of the thong. Then she gives me a playful tug and a slap on each cheek. 

Ali: You do have the ass for a thong. It’s also really cute. I think I will have some fun with it later.

After making her way all round me. She placed a hand on each of my hips. Two fingers under each side of the band and pulls downwards. Like with the pants she assisted me on stepping out of them.

Ali: How do you feel?

Trying my best to from a sentence. 

Me: I’m do..ng g..od. ma’am.

Ali: Good. We shall continue. Do you best to stand still.

With my panties in one hand, she reaches forwards and grabs my balls with the other. Giving them a squeeze and a pull. I let out a whimper and she gave me a devilish smile. Pulling a little more she begins to tie my panties around my balls. 

Ali: Looks like you enjoy this. You clitty, may I call it clitty? Has leaked on my hand. 

Me: Yes,you may call it clitty ma’am. I’m sorry it leaked on you.

Ali: Good. It’s not a problem that it leaked. I’ll use your leaking as a barometer. Do you have lube or lotion nearby?

Me: Yes, ma’am. I do It is in the coffee table drawer.

Walking over to the drawer she bends over. Giving me a view of her tight ass in those blue leggings. Upon returning with the lube, she squirts some in her hand. Then slowly applying it to the head of my clitty and working her way down to the base. Stoking it softly. Letting out a soft moan as she does. She kept a slow pace. In attempt to get her to go faster I start to move my hips forward. Swiftly I felt a sting on my ass.

Ali: What did I say about standing still! 

Me: It feels good and I want you to go faster. 

Ali: No!

Just as I opened my mouth to say something back and a felt a slap across my cheek. Moving her hand to the back of my head and tilting it down. Forcing me to look down into her eyes. 

Ali: I have plans for you and you will like them. Let this happen.

She began to stroke my clitty at a fast rate and adding a twisting motion at the end.

Me: I’m about to cum ma’am. 

Ali: Hold on a little bit longer.

Me: I don’t thing I can much longer.

As I finished that sentence, I started to cum all over her leggings. 

Ali: Let it all out.

She continued to stoke getting each and every last drop of cum out of me. Becoming a whimpering mess towards the end.

Ali: Wow,you did have a lot of cum built up. My leggings are covered. Continue to stand here. I’ll be back with a washcloth to clean you up. Do you have a change of clothes I could borrow?

Me: Yes, it’s been a while since I last came. You can go into the bedroom and have a look. Its just up the stairs.

As she went upstairs, I heard a scream of excitement. Yup, I know she saw what I had in the closet and in the dresser. The vast collection of leggings, a few dresses, bras and panties. Then hearing her skipping down the stairs into the bathroom to grab a wash cloth and then to the kitchen. When she returned to the living room she had changed into black biker shorts of mine. In her hands were a washcloth and a bowl of ice cold water. Placing the bowl down on the table she placed the washcloth into it. As it soaks she untied the panties that were around my balls and dropped them on the floor. Reaching over grabbing the washcloth from the bowl. Giving it a squeeze to remove let the excess water out.

As she touched me with it, I had the immediate reaction to pull backwards. She had a grasp around my balls that prevented me from backing up. After a thorough cleaning not missing a spot. Placed the washcloth back into bowl and picking up the cage. Separating the base ring from the cage. 

Me: What are you planning on doing with that? 

Ali: Don’t worry about it.

Me: It’s kinda hard not to worry about it.

Ali: You have no clue how big of a crush I have on you still. Flirting with you. I thought you had no interest in me and it did hurt my feelings. The other day when I saw you at the tail head. All those feeling came back. I knew at that point being direct was the only way I could possibly get your attention. 

Me: Yeah…I was a bit dense and didn’t really pick up on those hints. I didn’t think you would be attracted to a guy like me. 

Ali: You think just a bit dense?

Grabbing my balls and slipping them through the base ring and then my limp clitty. Picking up the cage part she slipped it over my limp clitty. Securing it with the lock. Upon hearing the that click of the lock being shut closed. I was about ready to faint. Could this even be real?

Ali: I’m glad that you keep down below the belt shaven but also need you to add your legs. For now, we are going to go upstairs to the bedroom.