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Boobs Make You Stupid Ch. 01

Boobs Make You Stupid Ch. 1

“That’s pretty!” “Oooh… Sexy!” “Slutty!”

Those were just some of the descriptors I used as I “window shopped” on line. It’s one of my favourite past times. Going to various lingerie sites and looking at bras, panties, stocking, garters, etc. So what you say. Women do it all the time. Except I’m a guy.

For a long while now, when given the chance, and privacy, I’ve dressed up in pretty, dainty things and pranced around my 16-th floor apartment. I stress 16 floors since I’d prance around with my big living room window curtains drawn unafraid of being seen as I look out over the park.

I won’t go into how I started crossdressing but to say after I caught the “bug” I just became so addicted. It was like cocaine.

So today, I was looking for some new bras. I already had close to 20 but the majority didn’t fit my new, new boobs. Let me regress a bit. When I first started, my first bras were training or AAA bras. My fatty pecs were just almost big enough to fill the flat cups. I wasn’t overweight or anything. Standing five foot seven, I thought I had a nicely shaped body; not too masculine and not too feminine. Not that I was complaining but maybe I can attribute my mini-man boobs on all the growth hormone feed given to all the chicken I’ve eaten since forever. Also from eating all the tofu too. I found out recently that tofu naturally contains estrogen.

I purchased one of those breast enlargement pumps which helped a lot. It included various cup sizes including nipple and bum cups. Yes, of course I used those ones too. The pump actually worked. My nipples became a bit bigger and harder. My bum became a little rounder. My chest swelled up from a small AAA to Double-A to almost a small A. The longer I used it, the longer my swelling would last. That meant I needed to buy new bras. Of course with bras, I wanted matching panties. Two new bras, four new panties, and a new satin slip were soon on its way. It was about then when I started buying make-up and wigs. With practice, I accomplished the different looks: sexy, slutty, innocent, demure. In person shopping for jewelry like bracelets, necklaces and earrings was easier since I could say it was for my “gurlfriend”.

At the time, I was very happy with my all my purchases and results. Wow! I looked pretty.

I continued to use the pump and was only able to maintain my size but not increase it. If I stopped for a while, the swell receded. It seemed I had plateaued. When dressed to go out or to the office, I’d taped my nipples and wear a jacket otherwise my pokies were too obvious.

But I loved to feel the swells when I ran my palms over my chest and dreamed of being bigger. Since no one knew of my Femme side, I wasn’t ready to consider other breast enlargement options. Then while surfing at one of the big box stores, I had come across some silicon breast forms. They were advertised for women who had a mastectomy but also applicable crossdressing.

It took a while before I built up enough nerve to order them. Not sure why since the process was pretty anonymous other than the obvious male name on the credit card. And what were the chances that someone processing the order would actual recognize my name.

“Click!” I selected the confirm purchase icon. It would be a number of days before they were scheduled for delivery (I was too nervous to go pick them up at the store). And finally Voila! On-line package tracking on my phone showed they were delivered.

It was at that point I started to fret. Where was the package? The apartment had small letter boxes and the package wouldn’t fit. Would they just leave the package out in the open? What were the markings? Could someone pick it up and read what was inside?

The good news was they didn’t leave the package out in the open. The bad news was I had to go pick it up from the delivery depot. I swear the clerk behind the counter gave me a knowing smirk as she gave me my package. While the box they came in was unmarked, the invoice was misfolded and identified the content as “Silicon breast forms — Size 4(C).

Safely in my apartment, I anxiously opened the shipping box and then took out the bubble wrapped contents. Each of the tear shaped breast form weighed more than half pound. They were beautiful although I was a bit disappointed with the almost flat nipples.

I wiped them clean and dried them before hooking on my bra and placing my new boobs inside the cups. They felt amazing as they warmed to my body temperature. I must have pawed myself for an hour. I snaked a hand inside the panties I wore to work that day and found my rock hard erection. I was so worked up, it only took a few strokes before I exploded.

That weekend, I wore them as much as I could. But there were a couple of problems. First, none of my bras fit properly. The cups were too small and the straps wouldn’t support the weight. This was a happy problem since it meant I could buy new bras. The second problem was since my new boobs were just supported by an ill-fitting bra, my boobs would either shift or fall out.

I solved the first problem by ordering three new bras from Victoria’s. And of course new panties to go with. I solved the second problem with some double faced tape. It seemed to do the job well enough. It hurt went I pull them off. But it was a good hurt.

The cheap, low quality breast pump broke and by now, my swollen naturally breasts had receded somewhat. I loved my fake boobs but shrinking to a small double “A”, I wished my new forms were bigger. Fortunately, my nipples remained hard and erect and my buttocks stayed nicely round.

On line I found an X-dress site that specialized in breast forms. I was so excited by the abundance of choice. My “C’s” were a good initial buy but were inexpensive and of poor quality. I knew going up just one size would be disappointing so I ordered double D’s. When they arrived, I was excited and no longer fretted about bringing them home from the mail depot.

I carefully opened the box and held each form in my hands. The triangular forms were weighty; a little less than a pound and a half each. After cleaning them, I slipped them into my now ill-fitting C-cup bra. My boobs spilled over while the underwire didn’t support me beneath. But I still love it.

I felt my new boobs. They were firm yet giving with a nice bounce. The half inch hard nipples stuck out nicely. The round hugeness was euphoric. I lost all track of time playing with them. That weekend, I attached them to my hairless chest with the glued I ordered with them just so I could wear my demi-cup, lacy bra. The matching, mini-thong panties barely contained my erection. I clipped my seamed vintage, fashioned nylons to the six strap garter belt before sliding on my stiletto heels.

Although it was warmish out today, I shimmied into a pink, knit dress and viewed myself in the mirror. It was tight enough that my nipples were clearly visible. Mind you they were so hard and pointed, they’d poke though steel. I also noticed as the shorter hem crept upwards, it left an inch of stocking welt uncovered.

After fixing my hair and make-up, I promenaded around my apartment. My sharp heels click on the bare floor as I walked and paraded in front of my large living room picture window. “Oh! I should buy some new bras!” And nearly two hundred dollars later, they were ordered and on their way.

Going to the office for work, I continued to wear some of my inconspicuous lingerie beneath my suits. A light spaghetti strap cam under my shirt; panties usually with stockings and garters below. It was unfortunate that I couldn’t wear my bra with my boobs. They looked great filling out my suit jacket at home.

I had been enjoying my double-D breast forms for a couple of months now. It was then when Britney started to work there. Her long blond hair draped down over her firm, C breasts. From her working out, she had a toned body and legs with a nicely shaped bum. Her crystal blue eyes attracted me like magnets to steel.

Terri my super asked if I would be her orientation buddy and of course I immediately said “Yes!” Maybe a little too enthusiastically as Britney tried unsuccessfully to stifle a cute giggle.

Working closely with Britney made me very happy. We became close. It wasn’t long before she asked if I would like to go for a drink after work and I quickly accepted. We soon became a couple. Even with not being a direct report, Britney decided it would be best to transfer to a different department.

Going out with Britney curtailed my ability to dress up regularly; not that I minded. The fact she too loved wearing lingerie and especially vintage lingerie help curtail my desires. But of course I couldn’t “dress” for work anymore and had to settle for my regular boy clothes. The only chance I had to change was when we couldn’t get together either after work or on the weekends.

“Jerry. I have to go visit my parents this weekend.” Britney told me. “My mom is sick and my dad needs some help.”

“Just the weekend? Is he okay? Do you need help? Would you like me to go with you?” I ask. It wouldn’t have been my first introduction to her parents.

“I’m not sure how long I’ll be. Dad just needs help. I took a week vacation from work.” Britney said. “Just in case. Mom’s not sure although the doctor said she just needed rest. But thanks for the offer to go with me. I love you.”

Thursday night, Britney stayed over and then left Friday after lunch. I left a bit later and went straight home to immediately change. My hands trembled as I opened the middle drawer of the tall dresser where I kept my things. I had planned this all day. I laid what I wanted to put on then had a hot shower. Other than some sparse pubic hair that I kept trim (which Britney loved), I had almost no body hair. Any scant hairs I had were so fine, they were pretty much invisible. So shaving wasn’t necessary. I used Britney’s lilac scented bath powder after I towelled off. I painted my finger and toe nails an ultra-shiny red.

I started with my red vintage bullet bra. It was trimmed with white lace and the full cups would easily hold and support my double-D breast forms I glued on. Even if the cups covered my boobs, I used some make-up to blend the edges to my skin colour.

The matching garter belt had a full panel front with three straps dangling from each side. Each strap split into two clips and would easily hold up my rose coloured, seamed, RHT vintage stockings. The four inch wide welts were beautifully laced.

I pointed each foot into the red satin, tap pants and pulled them up to my waist. The shorter legs left my welts and garter clips were exposed. The panties were also trimmed with the same white lace as my bra and garters. My six inch boner rubbed inside the soft, slick material.

I sat in front of my mirrored table dresser and thought. “Why not?” and brought my make-up case out from hiding.

I applied some light foundation first to hide my male imperfections. Eyes next with some smoky purple shadow and dark liner on my lids and heavy mascara on my fake lashes. I brushed on some blush to make my cheek bones more prominent. The ruby red lipstick and darker lip liner made my lips look sexy when I pouted. The shiny gloss sealed everything nicely.

I had a couple of wigs and opted for the Veronica Lake, Strawberry Blond, peek-a-boo style. I added on a string of pearls, drop pearl earrings and a couple of gold bangling bracelets.

I looked at myself in the mirror and was very happy with the results. But I didn’t want to just walk around my place in just my undies. I put on and buttoned up the white, Angora, V-neck cardigan leaving the top few buttons undone. You could see some my red bra and my cleavage; just enough to tease anyone looking. I decided on my knee length poodle skirt would be a good match along with my shiny white, five inch stiletto, open toed heels. Why would I want to hide the darker reinforced toes of my stockings?

I strode into the kitchen. My pointed heels clacking on the tiled floor with each step. Every move of my hand caused my bracelets to jingle. I loved the echoing sounds and it made me hard.

I prepared a simple chicken salad for dinner and enjoyed it with a nice glass of dry white. A glass became another then another until the bottle was empty. I opened another. It was dark out but still relatively early. Sadly I thought. “All dressed up and nowhere to go.”

That thought festered until I didn’t feel like sitting around, drinking by myself and doing nothing. It was barely after nine. I gulped my glass down and giggled. “Well… ‘All dressed up’ no one would know who I am.”

More inebriated than I thought I was, it didn’t take much to convince myself. It would be my debut outing dressed fully femme. I checked my make-up, reapplied some lippy and walked out the door. My heels thundered as I walked down the faux marble hallway floor to the elevator. My boobs heaved up and down with each deep breath. My heart boomed in my throat as I pushed the down button and waited. When the car arrived, I stepped inside. My knees trembled with each step.

I pushed “G”. The doors closed and the car descended. It stopped and opened the doors to the main lobby. A middle aged man and woman, obviously together, were waiting. As I stepped out, the woman looked at me with daggers and distain while the guy’s eyes popped looking at my boobs. It appeared neither seemed to recognise me as not a woman. Further emboldened, I smiled and continued my adventure out.

The night temperature was cool but not uncomfortable. Lucky for me, my Angora sweater kept me warm enough even if it was a short sleeved one. A cool zephyr breezed between my legs and up my skirt; enough to lift it and expose my stocking tops and garters. A guy walking behind, gave me an appreciative wolf whistle.

Embarrassed, I smoothed down my skirt and quickly walked in the opposite direction of my admirer. I really had no idea where I was going, just being out and about. Almost disappointed that there was only a few people out, I sauntered down the sidewalk.

“Hey baby!” Some guy called out from his car. “Want a ride?”

I stared down at him through the open passenger side window. He was some over-weight, greasy, sales guy type. His combed over hair was disheveled. His ill-fitted brown suit was wrinkly. His stomach stressed the buttons on his dingy shirt and stuck out more than my boobs.

“Sorry, Hon.” I teased. “I doubt you have what I want!”

Unexpectedly, he unzipped himself and pulled out his penis. It wasn’t small but it wasn’t huge; maybe about five fat inches. “How’s about just a blow job?”

Slowly I lifted my skirt. His eyes widened as he saw my stocking tops and garter clips. I pulled my panties aside and showed him my cock. “Sure! Come here and start sucking, Bitch!”

His tires squealed and left a tread mark a mile long as he sped away as fast as he could.

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