Tag Archives: Waggytail

“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.