Caught Out Again and Again Ch. 05

My girlfriend Cheryl caught me girlie dressed in my bra, panties, stockings and garters. Oh yeah, and my stiletto heels. Then she caught me masturbating, still dressed, in the middle of the kitchen. And then she caught me, still dressed, bent over and sucking my own cock.

Long story short, in the end, Cheryl really seemed to enjoy me dressed as a girl and the sex that followed was phenomenal. Over the next while, she insisted on my being dressed up when she returned home from her job. As a result, more and more my girl wardrobe grew while most of my boy wardrobe faded away. But I still was uncomfortable going out full girl.

Saturday morning. I quietly slipped out of bed as to not disturb Cheryl. She looked like an angel as she slept but I knew she was a devil in disguise. Our sex session was particularly over strenuous last night and I wanted Cheryl to be fully recovered for the next time she would ream my ass.

I stripped off my pink nightie and carefully removed my breast forms to clean them before I took my shower. While I loved wearing make-up, it was good to scrub it off under the hot spray of the shower. After I made sure that my hairless body was stubble free, I dried off with my big pink fluffy towel. I gave myself a light dust of perfumed powder and went to my room to dress.

Cheryl insisted that I dress up around the house. My boobs were still a bit damp and wouldn't adhere properly but I'd still have to wear a bra. In these cases, Cheryl bought me number of training bras. All of them were sized Triple A and very tight around my ribs.

I picked out my pretty rose coloured one. The thin straps were not adjustable and only had a single hook and eye to do up. Even with trying to pull the sides of my chest in, my puny man-boobs barely filled the teeny cups. The tight fit around my ribs and cutting straps over my shoulders were a constant reminder that I was wearing a bra.

I pulled up some pretty panties. They were a light pink coloured, lacy bikini with white lace trim and a small pink bow in front. I loved the way they felt as I rubbed myself through the material, but I couldn't walk around the house like that. I pulled on a small tank top, some tight shorty shorts and my pink flip flops.

In the kitchen, I warmed up the espresso machine. I could hear Cheryl start to stir as I prepped. I opened up the fridge for the milk and realized I needed to go shopping. There was just enough for her. I poured her double shot and was texturing the milk as she appeared. My art work still needed lots of practice. Handing her the latte, I said. "Morning Cheryl. I'll need to go to the grocers after."

"Ok. I'm just going to relax, read the paper and enjoy my latte you made for me." Cheryl informed me. "What are you going to wear?"

"You mean under my boy clothes?" I questioned. Of course, I had dressed up in my sexy lingerie before but they were always under my regular clothes whenever I went out.

"No. I mean regular clothes. Girl clothes." Cheryl told me.

"Uh... I... Uh..." I muttered.

"I'll go pick something out for you." Cheryl said and moved to the bedroom before I could say anything. "Where are your boobies? Go put them on."

After making sure my double D breast forms were properly attached, I went to see what Cheryl had laid out for me to wear. She turned to me and smiled. "I love your boobs. Start putting these on."

The shelf bra was extremely bright red with a bit of red lace trim. Cheryl hooked the eyes tightly and re-adjusted the straps short. It lifted my boobs high and my hard nipples poked out over in the satin demi-cups. The matching panties were teeny tangas which I put on before a light coral pink SIL garter belt with eight thick, dangling straps. I slipped on the neutral coloured stockings with a dark seam running up the backs and clipped them. The straps were adjusted tight against my thighs.

My cock started to grow hard in anticipation of what Cheryl had selected me to wear.

"Mmm... Barbie." Cheryl called me by my girl name. "You look very sexy. Good enough to fuck!"

She handed me a top and pants. I put on the light, white tee shirt. It was so small that it was more of a crop; I could barely pull it over my huge boobs and left half my tummy bare. The pants were tight, stretchy, white, low riding legging and pulling them over my stockings took a bit of effort. With the leggings and tee shirt stretched out, the outline of my lingerie was easily be seen. My nipples stuck out so much, they were impossible to ignore. As were the bumps from my garter straps and clips.

"Barbie doll. You better do something about that!" Cheryl nodded down towards my crotch.

I looked down where she indicated and I saw the outline of my erection. It was too hard to tuck under.

"Well leave it for now." Cheryl chuckled. She applied some mascara on my long, fake lashes, a little blush on my cheekbones and a light pink, glossy gloss my pouty lips. "You look like such a slutty whore with that boner!"

I thought it would be fun at first but now I was a bit concerned. Okay, I was a lot concerned. I wasn't wearing my wig nor did I have a lot of make-up on to disguise myself. "Uh... Cheryl? Uh..."

"Oh, don't be such a worry wart!" Cheryl told me. She handed me some white sneakers. "Put these on. And if you're that worried, you can cover up with your coat or maybe a baggy sweatshirt."

"But it's warm out today. I'll be sweating like a... Pig!" I protested.

"Well. Then don't wear anything over it and look like a slut!" She stood there with her arms crossed just daring me to defy her.

I bent over to tie my shoes. I saw myself in the mirror. Bent over, my legging were thin; they became almost translucent and made my red underthings even more visible but it did make my ass look great.

"You better get going before it gets really crowded at the store." Cheryl shoved my shoulder bag into my hands and rushed me towards the door. I managed to grab a light jacket on the way. She gave me a quick peck on the cheek and shut the door behind. "Bye!"

"Click!" I heard her lock the door.

Standing in the hallway and someone coming out of their apartment was too risky so I scooted to the elevator. I pushed the down button and waited. My heart was thumping like the big bass drum in a Scottish parade. I put the jacket on as the doors finally opened. I selected P4 where we parked our car and let out a breath as the doors closed.

The car started its descent. It sounded for each floor it reached and passed. Suddenly, it stopped at the main floor. I started to panic as the doors slid open to the lobby. No one got on. I pounded on the close door button but the door failed to react. I always believed the button was a placebo.

The door took its sweet time to shut and continue to P4. "Bing!" P1. "Bing! P2. "Bing!" P3. "Bing!" P4. The doors opened up. I took my first step to exit and came face to face with another tenant. It was the MILF from three floors down from me. "Sorry!" She apologized. As a Canadian, I mumbled a return apology as I stepped by even though it wasn't my fault. She did give me a weird look; a wry smile and then a big guffaw as the elevator doors shut.

Now safely in the car, I drove over to the grocers but not the regular one I would go to since I was too worried and embarrassed someone might recognize me. It was a bit further and smaller with less selection but I doubted I would bump into anyone I know.

I exited the car in the underground parking at the store. I zipped up the front of my jacket in hope of covering up my boobs, but they were so big the jacket barely closed and only accentuated their largess. The bottom of the jacket covered only half my bum. I left the zip half undone.

My knees were shaking as I walked into the store. Fortunately it wasn't that busy with only a few customers about and it made me feel a bit more at ease. Walking up and down the aisles and picking out my items made it easy for me to forget what I was wearing. I even got used to my big boobs.

"Oh yeah." I thought to myself. "I should get another box of ramen."

I found the ones we liked were on the bottom shelf near the back of the store with the other instant noodle. The box wasn't heavy but was a bit bulky and needed both hands to pick up. I bent over to pick it up. My legging waistband slipped down; I knew my panties and garter belt would show. The seam of my undies bit into my crack to remind me what I had on.

"Nice panties!" Said the female voice behind me. "Ooo... and she's wearing a garter belt too."

"I don't know." Said a different female voice. "She looks a little slutty bitch to me!"

A finger traced along the seam of my legging between my cheeks and then slapped my ass. I stood up quickly but did not turn; too frightened to face them. They called me "she" meaning they didn't realize I was a male. Cheryl had me style my short hair in a more androgynous manner.

Two hands came around my chest and grabbed my breasts. They pulled and pinched my nipples. "She's got huge tits but they feel too firm like she's had them done!"

They spun me around. The two females crowded close to me. Both were taller and blocked any escape. I guessed they were college aged. Both of them gave me a strange "not quite sure" look. A hand grabbed my crotch hard. "Fuck, Nell! She's a guy in drag!" Said the dirty blond haired one.

"What?" Asked the raven haired one. She grabbed me too. "Jeez, Louise! You're right! Holy shit!"

Raven Nell rubbed me. As much as I tried to ignore it, my cock grew hard at the assault. Louise tugged down my leggings. I just stood there with my panties and garter belt exposed. Both of them unabashedly laughed. "Fuck Nell. Look. She's got a boner in her panties!"

"She's pretty though. Maybe we should take her back to the dorm?" Nell said. "I bet the rest of the rugger team would just love to a girlie with a cock!"

"Even that small?" Louise asked sarcastically. "Let's go! She's not worth the effort."

"See you later, Doll!" Nell laughed.

The two of them left me alone in the aisle. My hard on bulged inside my panties as I pulled my leggings back up. I turned around. There was a shorter Asian man standing there. He spoke in with an accent. "Miss. You okay? Those girls bother you? They bad. Always sneak in and bother customers."

I was too scared to speak so I just shook my head a "Yes. I'm okay" manner. I sobbed. As I did, my boobs heaved up and down. I watched his eyes follow. I thought. "Fucking men! All of them pervs over a pair of big boobs."

I rushed my cart to the cashier and paid for my things, then dashed to the car. I was bent over and put my stuff inside. Then from behind.

"Hey babe! Nice fucking ass." I turned to see some yahoo in a red pick-up. Pissed, I pushed out my chest. "Wow, hon. I'd love to tit fuck those!"

"I got something else for you!" I replied and gave him my best sexy smile. I hooked my thumbs into the legging waistband and pulled them down with my panties to expose my cock. "Come on! I'll let you suck me and then I'll fuck your ass!"

Taken aback, he squealed away.

"He looked cute. Wonder how big his dick was?" I smiled to myself as I cover up. I got into the car. "Holy fuck! Did you just wonder about his dick?"