Cupcake: my personal journey through sparkly hell and ribbon DOOM

Submitted by submissive, Xavier Deed as part of his sentence from Trials and Punishments

And I sat there with my face resting in my hand after I had set down the phone. The project clearly outlined. I was to go to Victoria's secret, find myself some sexy clothing and wear it under my clothing. The whole idea of going to buy the clothes was unsettling enough. But the idea of actually wearing it, well that just made my nutsac hang a little less low and my cock want to curl inward. I sighed and went out to purchase the clothing as I was commanded to do. The store itself wasn't that, the salesgirl assumed it was a gift and I just kept right on letting her believe her assumption. After all, confession was not part of the bargain. I found for myself a pair of silky textured thigh high stockings. I picked textured hose in my refusal to actually shave my legs, I figured the texture would hide my leg hair fairly well. A pair of pink panties and a matching bra completed the ensemble. There was a tricky moment when I was asked about size, but I bypassed that by telling the salesgirl my friend often borrows my shirt and pants. I felt fairly intelligent in that bit of covering up.

The following morning after my regime of morning jerk, jog, and shower; I moved to put on the scanty undergarments. Luckily it was a casual day at work so I'd be able to cover any lines from the undergarments with baggier clothing in thick materials. The stockings were sort of tricky. They don't slide on quite like socks do and it took a bit of work to pull them up in little bunched jerks along the hard muscled length of my legs. The texture didn't cover my hair quite like I'd hoped, and little hairs stuck out, much like porcupine quills along my legs. But the silken feeling against my hand as I ran my palm over the sleek line of my calf was oddly enticing. And I do have to admit I have better looking legs than I thought. I did, indeed, wonder how the form of my leg might shift standing in heels. The stockings were oddly tight, especially that lace top around my thighs, it cut in where I thought it would lay smooth. I discovered that lace is not the soft material it appears to be. It's sort of scratchy when it shifts on bare flesh. Again, I spent a moment enjoying the feeling of that silken hose beneath my palm. And I do have to admit my cock did twitch more than once as I rubbed my own leg. It was deliciously naughty.

Next came the bra. Luckily I'd been with enough women to know the clasp in the front and slide the bra around trick. But what I wasn't aware of is how easy it is to twist the bra and half one cup down and one cup up. And I never would have guessed how that rolling band just under my pecs could pinch and roll. I swore if I were a woman I'd just let my breasts swing free. But, oh my God, I loved the feeling of those silk cups over my nipples. To be perfectly honest, that sensation made me moan and my cock did start to lift and grow. I stalled and toyed with my nipples through the material of my bra, easing it back and forth around my body slightly so those tight cups would pass over my nipples. It felt oddly whorish and I wondered how I'd get through the day with that teasing sensation every time I moved my arms. By now I was half hard and my hand kept drifting to toy with the head of my penis. I knew I shouldn't. I knew I should strive to have that swelling fade so the panties wouldn't be quite as tight. But I am weak, and so I toyed away until I reached to slide on the pink panties.

I can not begin to describe how tight they were. It's like they were permanently bonded to the inside of the crack of my ass. My poor sac pressed upward against the under-curve of my torso. I feared dropping anything and swore to myself that today I would not bend over if my life depended upon it. The panties did not quite cover my dick. No matter how I stacked myself within that tight silky tiny garment, I poked out. My only real option was tucking and that just seemed ridiculously uncomfortable. I knew I shouldn't have toyed with myself. Yet, in all honestly, I was unable to stop myself from doing so. I never in my life felt so wickedly whorish. So wanton, so freaking lewd as I did dressed only in tight clingy silky ladies undergarments. I walked to the bathroom just to see myself in the mirror. Now I admit at first I laughed and I debated ripping it all off and just saying I wore it. But, some part of me wanted it. And a larger part of me wanted to do it because she had told me to. So I quickly dressed to hide the sexy clothing and attempted to go on through my day.

I never blushed so much. Each movement of my body in the course of my day brought the reminder I was semi-restrained in sexy pink silk and lace. And just that mental reminder surged a rush of my blood right on into my crotch. It, indeed, was a long day. I debated several times sneaking away into the bathroom for a little stress relief, but I had been told that I could only have the one in the morning. I was a walking hard on. She was right, being a pretty princess under my clothes did excite me.