Caught Out Again and Again Ch. 01

Caught Out Again and Again Ch. 1

"What the...?" My girlfriend Cheryl shouted out.

I was standing in our apartment kitchen preparing lunch. That wasn't so bad but I was in a pinny which was open in the back and left my panty covered bum exposed. Up until then Cheryl had no inkling of my dressing fetish. But... let me start earlier. Before I met and moved in with Cheryl.

I'm not sure when I got the urge to dress up but it was a while ago. After graduating and moving into my own apartment, my desires really bloomed. Of course, in an apartment building, there are no in apartment washers or dryers; it was all provided in the basement laundry room. That's where it began.

I took some dress shirts downstairs to wash. Most of the machines were running; those that were finished had wet clothes in them waiting to be transferred to a dryer. I waited a few minutes but when no one came by, my patience was short and I pulled out the wet stuff and shoved my stuff in. When I returned, all my white shirts had a pink hue to them. At the bottom of the washer was a bright red, women's thong.

Pissed at the fact I had to try and wash out the colour from my whites, I kept the thong and returned to my place. I noticed how tiny the triangular crotch piece was and how thin the strings were. My cock was rock hard. I took it out and used the thong to masturbate with and ejaculate a huge creamy wad into.

The following times I needed to do laundry, I rummaged through all the machines to see if I could find more panties. Sometimes I was really successful, other times not so much. My collection of female underwear grew. Then I was looking through a washer and found one of those lingerie bags. I opened it up and pulled out a matched set of white lacy bra and panties. Quickly I zipped the bag up and returned it the washer before dashing off back to jerk off.

I had started wearing one pair of panties while I used another to beat my meat with. So this new set added a new sensation. My new bra was a bit tight around my chest and had to stretch the elastic a bit. The lacy cups weren't that big; maybe a B. It felt good when I rubbed my hard nipples through them.

I slipped on the panties. I looked at myself in the mirror. The matching panties were high-waist, tight boy shorts that left some of my bottom ass cheeks exposed. My pink knob was pointed up towards the waist band.

"Bing!" The reminder to change my clothes over to the dryer shouted out.

"Shit! I'll have to jerk off later." I took a chance and just donned some sweats think it was loose enough to hide the fact I was still wearing the bra and panties before I nervously dashed downstairs to the hopefully empty laundry room. Of course it wasn't. The girl whose laundry I just pilfered was also changing over her stuff. She didn't look happy.

"You need to be careful." She said suddenly. "Someone has stolen some of my stuff from the washer!"

"Yeah." I answered sheepishly as I pulled out my wet stuff. "Can't trust anyone now, eh?"

I guess I didn't realize how loosely my sweats fit. While the oversized shirt hid the bra, I didn't realize the back side crept upwards. Plus I didn't tie my sweat pants that tightly. With my arms full of wet clothes, the high waist panties kept me from feeling my pants slipping down.

"Ooo... Very sexy!" I heard her say. "I have a pair of panties just... Hey! Those are MY panties! You're the fucking thief aren't you?"

By now my pants slip down even more and were around my knees. "Uh. I.. Uh..."

"You're wearing my panties you sick fuck!"

I tried to run but with my pants around my ankles, I ended up on my face instead. I tried to get up but her foot on my back stopped me. "You sick fuck! You get off stealing and wearing women's underwear don't you?"

She took her foot off my back and told me to stand up. I obeyed her order and found her videoing me on her phone. Although it was too late to hide, I quickly tried to pull up my pant and cover up. "Leave them. I'm missing the bra too. Are you wearing it? Take off your top."

Still filming as I pulled off the shirt and showed her I was wearing her bra I was now under her command. From then, I was basically her slave to do as she wished. Ms. Lara lived with her partner Ms. Natalie. Dressed in the same bra and panties, the two made me clean their apartment or do their wash or generally just do stupid little things for them.

After a bit, Ms. Lara and Ms. Natalie noted how seedy my outfit started to look. They ordered me to buy and wear a classic French maid's outfit. The bra had padding sewn into it to give me boobs. The panties were white and frilly beneath the short black maid's dress with plenty of stiff crinoline. The stockings I had to wear were fishnets held up by a garter belt. And of course I had to wear shoes. Four inch pencil heels with open toes to show off my red painted nails.

But finally, the two got bored of me. They still called me to do some stupid tasks but mostly left me alone. I was actually disappointed but they let me keep the maid's uniform which I wore around my apartment.

From then I started buying my "stuff" on-line. It was so much less embarrassing than buying lingerie at a store in person. For work, I almost always wore my lady's undies under my man clothes. Of course I couldn't wear a bra since it was too obvious but I had found some chemises that would pass for undershirts. Panties and stockings were another matter. Sexy French lace panties, Wolford stockings and six or eight strap garter belts were regular occurrences and easy to hide behind my desk.

Miranda or Randi as she preferred, worked in the next cubical to me. She was a cutesy, extroverted, blond BBW and we were close workmates eating lunch together or gossiping about others. Her big, ice blue eyes were penetrating when she looked at you.

We were packed into a conference room to listen to Billy "the big boss" Boggs hype last quarter's results and the upcoming quarter funnel. Randi and I sat in the back of the dim light room. I leaned over and whisper a rumour into her ear about Todd the brown noser. Randi chuckled. She placed a hand on my arm and told me. "Sonita got ahead by giving head!"

I supressed a snicker.

"...last quarter's star performer is..." Billy announced. "Sonita! Congrats!"

"You mean, star blow job performer!" Randi leaned towards me but then lost her balance a bit. She caught herself by bracing a hand on my leg.

Now for those of us who wear stockings and garters, there are a couple of tells. One: tight stocking welts make a slight indentation around your thigh. Only noticeable when you feel them. Two: garter straps while hidden under your pants can be also be felt through the covering material. My straps were 3/4 inch wide to make it more obvious. Three: Both the adjustment buckle and the clips make protruding bumps if you aren't careful.

Randi didn't remove her hand. She traced her finger up along the strap and then down to the clip. Her piercing icy glare bore straight into my brain. I could feel myself start to sweat. We remained silent for the rest of the meeting.

Quitting time that evening, I tried to leave while Randi was away from her desk but she caught up to me at the elevators. "Where do you think you're going?"

Silently and obediently, I followed her to her apartment. Behind closed doors, she made me strip and show her the delicates I wore. She used a strap-on and fucked my ass sore all night and then I became her office bitch where I had to do nearly all of her work. That lasted until she got fired for not doing her own work.

A bit later, I met Cheryl. We seemed to hit it off well. The first time we had sex, it was the greatest I had in a long time. She was constantly hot and horny so it kind of quelled my crossdressing desires. Plus I didn't want the chance of being discovered. When she got her associateship, we soon moved in together. It was due to her new position that caused her to dress up more. She always dressed sharply but with the additional income, her sexy lingerie beneath her business suits and high heeled shoes had become a new normal part of her work attire. I'd watch her dress and get an erection every time; not just because she was so sexy but what she wore. Her demi-cup red lace bra just cradled her F sized boobs under the silk camisole. A string thong so small it barely covered her hairless plump pussy and left her smooth bum naked. Seamed, RHT, coral coloured silk stockings glide over her perfect shapely legs. The four inch wide, red lace welts were clipped to her red, eight strap garter belt. All hidden beneath her white silk blouse and cream coloured jacket and mid-length skirt. Her shiny red, five-inch stiletto heels made her bum and boobs stick out even more.

It was enough to get my crossdressing juices flowing again. Underneath the bed sheets, I secretly stroked my hard cock at the thought. Pre-cum coated my palm making it easier to slide up and down. After Cheryl kissed me good-bye and left for work, I immediately went for her dresser drawers.

"Gold Mine!" I said to myself. She had a number of very scanty items. Cheryl being very shapely meant it was easy to find things to wear, but then the thought. "Should I?"

After a moment, I actually said to myself aloud. "Of course I should. What kind of a stupid question is that?"

While her white shelf bra was a perfect fit (sans boobs of course) around my chest, the boy short panties were a bit tight. I pulled up some opaque white thigh highs and slipped on a pair of her high heeled, open toed mules.

I looked at myself in the mirror and rubbed my erection through the panties. I watched my reflection. My body was vibrating and my knees were trembling. I started to cum. "Uh... Uh... Uhhh...!"

I couldn't move. I couldn't breathe. I could barely stand.

It took some time before I recovered enough. I remained dressed in my bra and cum-filled panties and went to my home office. Instead of work, I went on line and ordered a whole shitload of things: bras, panties, stocking, garters, heels you name it. Then I came across a website that sold breast forms.

I scanned through all the options and sizes and decided on a relatively decent set of triangular shaped, double-D sized forms with the biggest nipples available. Of course I needed to go back and change my bra orders to the right cup size.

Little by little, my packages arrived. With Cheryl away at work, I had little fear of being questioned about their arrival. Wearing the different items was great but finding a hiding place was difficult. At first, I hid it in my sock drawer but as the number of items grew, the drawer became insufficient. I cleared out a filing cabinet drawer and hid my stuff in there.

In a typical day, after Cheryl left for work, I'd shower and shave. Fortunately, Cheryl loved my mostly hairless body and never questioned it. I'd leave a small soul patch because I thought it looked cute under my panties. After dressing up, I'd do some work in my office but often would get too distracted and need to jerk off. Of course I'd always time it to change back to my regular clothes before Cheryl returned.

Weekend was laundry day. I had taken down a load. Since I always do the laundry, I wasn't concerned with washing my delicates. I'd place both Cheryl's and my white or light washables into one of those bags that allowed you to use a machine rather than hand wash. I had a single red g-string thong to wash separately so I just threw it in with some dark socks and tee shirts knowing it would be okay.

I guess I was cleaning out the bathroom when the reminder to change the laundry over went off. I thought I heard Cheryl say something but only heard the front door shut and continued scrubbing the bowl. The smell of bleach from the gleaming porcelain was always a satisfactory sensation. Pleased with myself. "Oh! I didn't heard the laundry timer. Better go swap it over before someone drags our shit out of the machine."

I walked to the living room and found Cheryl sitting there. Dangling from her middle finger was my red thong. I tried not to react. "Nice. You buy new panties? They look sexy."

"No Geary. It's not mine. I found it in wash with your stuff!" Accused Cheryl.

"Uh... I've never seen them before!" I lied. "Maybe they were there from the last person to use the machine and forgot them."

She still looked at me suspiciously.

"You know, sometimes things get stuck to the tub after it spins!" Which is true but these machines don't spin anywhere close to being fast enough for this to happen. I lied some more. "It's happened to me a couple of times. I'll take it back down in case the owner comes back to find it."

I could tell from her eyes, Cheryl still wasn't sure but she said no more as she flipped the offending red thong at me.

"Phew! That was close!" I thought to myself. "I'll have to be more careful."

I tried to take more care to not get caught again, but as things quieted down a little, carelessness increased. More often than not when Cheryl left for work, I'd "dress" for my work too: a bright red bra and pink and frilly panties. Stockings and garters were always a must regardless of the weather. I loved the taut straps against my thighs. "Mail should be here by now."

I pulled on some loose fitting sweats to especially hide the fact I was wearing a bra, changed my heels for some flip flops and went to the mailroom. In our mail slot was a notice to pick up a package at the post office. I hoped that it was the delivery I was expecting. I felt my cock inside my panties get hard and I got on the elevator back to the apartment.

"Hey, Geary!" Said Terri from down the hall who just jumped in before the elevator doors closed. Her eyes drifted towards my chest and then down to my feet.

"Oh, hi Terri!" I stuttered a reply wondering if she could tell what was beneath my shirt. I thought. "Was I showing? Could she see the outline of my bra? Shit! I'm wearing stockings. Can she tell?"

The rest of the trip was silent although she tried not to stare.

Safely back in my place, I closed the door behind me and panted. I was incredibly turned on by almost being found out. I checked myself in the mirror for any tell signs but couldn't see anything. Feeling a bit relieved, I looked at the pick-up notice. The two kilo package was indeed what I was hoping for; my new breast forms.

Of course I had some forms before but I thought them too small and were not that expensive. These ones were big double-D's with extra big and pointed nipples. These boobs were self-adhering, higher end, realistic looking and feeling.

Excited, I soon forgot about the close call with Terri. I changed into some jeans over my panties and stockings but with the warm weather couldn't wear my sweatshirt. A golf shirt would do zero to hide my bra so reluctantly I took it off.

At the local post office, I handed the notice to the female clerk. A few minutes later, she returned with the plainly wrapped box. She smirked as she handed me the box. A quick glance at the misfolded invoice let anyone looked know there were breast forms inside.

I took the package and quickly returned home with a raging hard on in my panties.

In my home office, I carefully took off the outer wrap and opened the box. They were beautiful and big. Each weight over 600 grams; about a pound and a half. I carefully wiped them clean and placed them against me. They seemed to just naturally stick on to me. I could have almost gone braless even as the heavy weight pulled down on my chest but I thought it would be too skanky to go around without one. My bra cradled my new boobs perfectly.

I pranced around the house just loving the way they felt and felt sad when I had to removed them and change back into my boy clothes before Cheryl got home. I couldn't wait until the next time.