Caught Out Again and Again Ch. 03

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Why am I always caught in women's lingerie?
1.7k words
4.52
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Part 3 of the 6 part series

Updated 06/10/2023
Created 08/09/2020
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grgy56
grgy56
1,564 Followers

There I stood. Dressed and girlie in the middle of the kitchen with my spent cock in my palm. Cheryl my girlfriend came home unannounced to get some files she forgot this morning and caught me in my bra, panties, stockings and garters cleaning up my lunch dishes. She didn't recognise me at first especially with my make-up and blond Farrah Fawcett wig on.

She was really angry and stormed out the apartment door. I wasn't sure of how I felt: scared at being caught; scared of what was going to happen next; scared of what Cheryl thought and scared what would happen next. I just found I was totally excited by my predicament.

I pulled aside my pinafore apron and took my erection out from my panties. In the middle of the kitchen, I jerked myself off. She had forgot the files again and suddenly returned in time to see the end results of my masturbation. I jettisoned my cum onto the Spanish tile floor.

"You're a fucking sicko!" Cheryl spat out as she grabbed the forgotten files and stormed back out the apartment again.

I looked down into my palm and at my wilting erection. My body and legs quivered in post-orgasmic vibrations. The last dribbles fell onto my RHT stockings peeking through my open toed stilettos.

It took a few moments to gather up enough strength to move. I tucked my leaking, flaccid dick back into my panties. Then getting some paper towels and on my hands and knees, I wiped up the spillage from the floor. My panties dug into my ass crack and I felt a stirring in my panties.

Normally, if I dress up and cum, I feel I no longer want to remain in drag. But today was different for some reason. "Well, I've already been caught out. Cheryl said she won't be back until late this evening so I may as well stay dressed up for now! At least before she gets back tonight."

I spent the rest of the day trying not to think about Cheryl catching me but the consistent boner in my panties prevented me from thinking of other things. I kept edging myself hopeful that it would be sufficient to quell my horniness, it helped a bit but in the end, no. By four-thirty, I realized that it wasn't going to do anything anymore. Watching shemale porn on the big screen only exacerbated my wantonness. On the chesterfield, cock in hand, I stroked myself mimicking the actresses I was watching. I continued to edge myself until I came across some self-sucking/self-facializing action.

I always loved watching the self-suckers, but the thought of me doing it never really crossed my mind for some reason. Today I wanted to try it. I laid back on the cushions and brought my stocking clad legs over my head. Looking at my stiletto heels and my painted toes made me even harder. I brought my knees closer to my head. My cock was about a half inch from my straining lips; I could just lick my sweet pre-cum from my pee hole with the tip of my tongue.

I needed more downward force.

On the floor with my back side up against the couch, I spread my legs over my head into a wide vee and brought my knees downwards again. It was a bit better as I was now able to get my lips around the fat part of my knob. I shimmied and wiggled my butt upwards. My knees were actually touching the floor. More than half my shaft was inside my mouth.

Now Cheryl is a great cock sucker. Her talent is comparable with any other girl but I know what I like to feel.

I pulled back my foreskin and exposed my pink knob and swirled my tongue around and around. I gulped down the pre-cum free flowing down my throat. As I reached between my legs to play with my asshole, I found I could slip my elbow passed and pin myself against the floor. "I wish I had something stuck into my ass right now!"

Not wanting to break the moment, I guess my finger would have to do for now. As I fucked my hole with my middle digit, I thrusted my cock deep into my mouth. I used my other hand to squeeze my balls. My finger tip found my prostate gland. It was like a big red button to launch a nuke!

My white hot cum exploded into my mouth. I tried to swallow it all but there was too much and some of it squirted out from between my sealed lips.

"Jesus fucking Christ!"

I recognised the voice. Cheryl was standing at the open doorway.

My cock was still rock hard, in my mouth and pulsed the dregs of whatever cum I had left in me.

I untangled myself; cum still dripped from my chin. I looked ashamed at Cheryl who just looked stunned. She shook her head and said. "Unbelievable."

She entered the bedroom and closed the door behind her. I cleaned off my face and went to my office. Unfortunately all my man clothes were in the bedroom and I dared not go to retrieve them. I removed my wig and sat in my chair and waited and waited and waited.

About an hour later, I hear Cheryl come from the bedroom. She stood in my doorway dressed in a baby blue night gown. She shook her head at me again. "Jesus! Don't you have any shame? Why are you still dressed like... like... like that!"

"I... My clothes are in our bedroom and..." I began but was immediately interrupted.

"I'm not sure it's OUR bedroom anymore." Cheryl glared. "So why... this?"

"I just like to dress up in women's things. I'm not gay or anything. I just like to wear nice lingerie." I explained but even I had a tough time believing what came out of my mouth. "I was going to change back before you got home... the second time but you came home early again."

"I was so upset at seeing you in..." Cheryl used her head to indicate my feminine attire. "I couldn't concentrate at the meeting. We couldn't get the contract signed and cancelled the dinner after that."

I tried to apologize but Cheryl didn't want to hear it. She just stood there. I couldn't figure out what she was thinking. Finally she spoke.

"If you want, go change but you're not sleeping in the bedroom tonight. I need time alone to think about this." Cheryl spun and went to the bathroom.

I scurried to the bedroom and stripped down as quickly as I could. I changed into some sweats and collected my girlie things before returning to my office. I figured I'd have to sleep there tonight.

I re-emerged from changing and found Cheryl sitting and sobbing. I'm not sure apologizing was the right thing but I tried anyways. "Cheryl. I'm sorry."

"What? Sorry you got caught? Sorry you're a cross-dressing sissy? Sorry you've upset me?" Cheryl questioned me back.

"Mostly sorry that I've upset you." I admitted truthfully and then lied. "And sorry for the way you found out."

"Tell me. How long have you been wearing women's things?" Cheryl queried me.

"A long time. Way before we met. While I was still at home." I told her. "I just like the way it feels against my skin. It makes me feel so comfortable and at ease."

"Do you only dress up at home?"

"No. I've worn my lingerie under my clothes some times when I go out. I would never go out dressed as a girl."

"Is this the first time you've been caught?"

"No. I've been caught before. A number of times before we were together; a couple of times a little while ago when I went grocery shopping." I related and added. "And you almost caught me a couple of times. You were coming out of the shower and almost caught me. Remember the laundry/thong thing? Those were mine. There were some other close calls."

"A couple of times? Who caught you?" Cheryl demanded.

"About a month ago, I was in the grocery parking lot. I was wearing panties, garters and stockings." I started. I couldn't believe how the words just fell out of my mouth. "The stockings were actually stay-ups with heavy elastic welts that made my clips difficult to hold. One of my clips popped and I wanted to fix it before I went shopping. I opened up my jeans and pulled them down just a bit to fix the front clip but the back one ended up popping too. I had to push my jeans down further to reach around and fix it. As I tried to reattach it, I didn't notice the woman standing beside the car watching me. She just smiled as I pulled my jeans back up."

"And the other time?" Cheryl asked.

"Anastasia from down the hall." I told her. "I had stretch to reach up and get something from the top shelf. When my shirt rose up, she saw my panties sticking out from under my shirt. I'm sure she'll use it against me somehow."

"So even though you've be caught a number of times, you still dress up in women's clothes and still go out that way. Have you ever had sex with anyone else since we've been together?" Cheryl continued and added. "Female or male or anyone!"

"No. I have been truly faithful to only you." I was I guess a little proud of that. "I love you very much. And only you."

That seemed to ease her mind a bit but she continued her inquiry. "Did you ever dress when we went out?"

I looked at Cheryl as she asked me her questions. She didn't appear as angry or upset as before; now, almost curious. "A couple of time, I wore some panties under my pants when we went shopping."

"When I caught you in the kitchen today that turned you on didn't it?" Cheryl probed. "You jerked off as I watched. After I left, you stayed dressed didn't you? Then when I came home tonight and found you SUCKING your own cock... You didn't even stop. In fact I think it made you cum harder. Didn't it?"

All I could answer was. "Yes."

grgy56
grgy56
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  • COMMENTS
1 Comments
cdCindy1cdCindy1over 3 years ago
please continue

This is a very realistic story. I know if my wife caught me that she would react similar to your wife. Once the questions start, I think it might just take some time before she comes around to accept you (and me) for who we are. Yes, we are sissy crossdressers. I myself have taken it further and have engaged in hot gay sex with men who love being with CDs. It turns them on and it turns me on too. Maybe you might explore too ?

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