Tag Archives: sissy maid

“Little Dick”

A few days ago, the woman who runs Waggytail, the agency I foster dogs for, emailed me to ask if I’d like my apartment cleaned.  Again! Yes, the “apartment cleaning panty boy” I posted about here was also provided by Holly, who was a pro-domme in a previous life. “We girls gotta stick together,” she loves to say, when she has these men show up bearing cleaning supplies, dog food, ice cream and, sometimes a donation! Fostering dogs can get expensive! Not to mention the amount of paper towels we go through!

So I was excited about this latest panty boy because not only would he be cleaning my apartment and providing me with some much-needed supplies, he was gonna give me a few bucks! I just needed to hold up my end of the bargain by making fun of him. I’ll admit, that isn’t always as easy as you’d think. Being mean is a lot more palatable in print; doing it in person is tougher, especially when I’m faced with a panty boy. I’ve always had a soft spot for fetishists and am more apt to feel empathy than disdain. So it would be a stretch!

Holly showed up and introduced me to “Little Dick,” a suitably doughy, self-deprecating, semi-middle-aged man. He proffered the paper towels and retired to the boudoir, where he could change into his lingerie. He had quite an impressive selection of panties and proudly paraded them around my living room, asking if I’d like to take photos. He also provided me with a script, of sorts, and requested that I read my lines:

10 things you say to a guy with a small penis
1. OMG!! (giggle and point)
2. Are you cold?
3. Does it get any bigger?
4. I didn’t know they came that small.
5. Aww, it’s hiding.
6. I hear excessive masturbation shrinks your dick.
7. Is it in yet?
8. Are you kidding me?
9. My 8-year-old brother has one like that.
10. It’s soooo cute!

Mind you, I had to insert my editorializations:
1. I’m giggling! I’m pointing!

2. I know you’re not cold, cause it’s warm in here.
3. I’m sure it does get bigger! No, I don’t want to see!
4. I do know they come that small, ’cause I’ve seen smaller. I know! Well, I’ve seen a lot of penises…
5. Yeah, hiding. Hah!
6. If excessive masturbation shrank dicks, everyone would be dickless!

7. It isn’t anywhere close to being in. And it won’t be!

8. Yes, you are kidding me! We’re kidding each other! Right?
9. I don’t have a brother!
10. It is, actually, kinda cute!

Holly didn’t hang out too long, so soon I was alone with Little Dick. Anyway, I was actually enjoying myself. We had a great conversation about fetish parties, old and new, Hellfire and how things had gotten so mainstream and how that had made it all feel like less fun. I took photos of each “costume” change and critiqued him on which pair made his penis look smallest. He even asked if he could “finish,” which meant I’d really be earning my money. He giggled as he pointed out that he was “only using two fingers” and I had to force myself to be patient. The fact that someone would be ringing my buzzer any minute added an exciting dimension of urgency.

All in all, Little Dick and I  had a lot of laughs and it turned out to be a far more enjoyable evening that I’d anticipated. He wasn’t the best at cleaning but he was good company. Of course, the $50 sure didn’t hurt! I’m looking forward to him back.

Apartment Cleaning Panty Boy

Yes, I have a strange life. I travel all the time but want to be in one place. I say I want a job but I don’t know how I’d fit one in! I manage to live on almost nothing and make it look damn glamorous. Many people I know say they envy me, that I’m “livin’ the dream.” I can’t say that I disagree! Though it would be nice if my glamorous life were just a bit more profitable.

In keeping with my usual weirdness, I had a cleaning person at my apartment this afternoon. You might wonder how I can afford a cleaning person, being broke and all. Well, I didn’t pay this cleaning person. He did it all for free. And dressed in nothing but a pair of lacy magenta panties.

He wasn’t bad looking, not exactly fit ‘n’ trim but not a total slob, either. I can’t say the bikini panties were the most flattering choice but I’m sure they make him happy! His back was hairy, which is always a bummer, but he wasn’t overly hirsute elsewhere. He had a pleasant demeanor and engaged in small talk, not the usual silent, slavey sort.

His first task was to chuck my Christmas tree out the window. I know, weird. But there’s a pile just below that looked destined for the city’s mulch project and it made more sense to toss it out the window than drag it through the hallway, trailing pine needles the whole way. He swept up the mess and started on the kitchen, washing my dishes and mopping my floor. Then I had him tackle the bathroom, scrubbing those floors, as well as the toilet. “Better you than me,” I cracked as I walked by the bathroom and saw him bent over the commode.

I had to keep him busy until 8:00 because his next gig was with a girl who wouldn’t be home til then. I’ve become almost obsessively neat so I didn’t have much more work for the guy! I was already having him clean things that weren’t all that dirty. I had him sweep and clean the living room and hallway floors but it still wasn’t 8:00! I sent him out to pick up some dog food for the girl he was going to next, just to stall, and he said he’d get himself some dinner as well.

When he returned I packed up the little puppy that he was to deliver to his next appointment and showed him to the door. He did a great job but I have a feeling I didn’t offer him as much ridicule and humiliation as he’s ordinarily subjected to; I just didn’t have it in me. Maybe I’m just not as weird as I used to be.