“I’m worried that won’t fit around my gut!” He pulled up his red flannel and exposed his hairy bulging stomach. I laughed.
“It barely fits around my gut,” I said. “Maybe I can get creative and make something work.”
“I brought my own panties, by the way.”
I was honestly impressed. “Oh really? Well let me see them! I want to be sure they match.”
He pulled out a pair of black cotton French-cut panties with a lace trim on top that was squished in one of the pockets of his jeans. His face flushed as he rescued them from the tight space, but he looked at the panties lovingly.
“Those are really nice. I think they’ll look great on you,” I said. “Really, can’t go wrong with a pair of plain black panties. They will match with anything!”
The garter I picked out for him was also black. The black lace garter, the black panties, and the nude thigh-highs made for a sexy combination.
“I would like to try it on,” he said.
“Yeah, of course!” I walked toward the dressing room, then stopped myself. “Hey, um, I have to ring you up first. Once I take the stockings out of the box I can’t put them back in. I’m sorry.” I hope I didn’t just ruin the moment. This was a delicate situation. Being a cross-dresser enthusiast/motivator was a new and exciting part of my job, but doing inventory on pantyhose was also part of my job.
“Oh yeah. Sorry. Like I said, I’m new at this,” he replied.
We went back to the register and a few customers were actually waiting for me to ring them up. I had forgotten about the rest of the store. Fortunately, they had punch and an assortment of porn DVDs to keep them occupied.
“Let me check these people out and I’ll be right with you,” I said to the lumberjack. I rang up a few people who were getting standard stuff. Lube for one person, a mix of pornographic DVDs from our $5 bin for someone else, a Barely Legal magazine and a Fleshlight (an incredibly popular replica of a vagina that conveniently comes in a receptacle that resembles a large flashlight—for those of you who didn’t know) for another. I quickly got them out of the way so I could get back to helping the lumberjack, whom I realized I should stop calling “the lumberjack.” Personal attention was the key to good business, was it not?
“What’s your name, by the way?” I asked him when it was finally his turn at the register.
“Billy.”
Billy. I liked this name. It was kind of unisex, so no matter which gender he identified with I could use the same name. I always thought the name Billy for a woman was hot. There was a woman named Billy (or Billie, actually) on Days of Our Lives, which I watched in its entirety when I was sick one week in college. And damn, that character was hot. Had I not been sick at the time, I would have definitely been aroused.
I rang up the pantyhose and the garter belt. I stretched the sides of the lace in the garter as far as it could go, and it still didn’t look like it could fit Billy.
“I’ve got an idea.”
I took the safety pins off the garter that were holding the merchandise tags and moved them to the back of the garment. I attached pieces of twine I normally used to tie down cardboard boxes that went in the recycling bin in between them. It gave the garter an extra foot of length. The twine really complimented his burly, grungy look. My Saturday night-shift was suddenly like an episode of Project Runway.
“Let’s get you back to the fitting room!” I said.
The fitting room was actually just the bathroom. Calling it a “fitting room” just felt fancier and I assumed he wanted to feel fancy, with thigh-highs and a garter and all. He took his purchases and went into the room. I stood nearby.
“If you need anything let me know!”
I hung around outside for a while, almost hoping that Billy would call me in to see him. I was definitely invested in his fetish well-being at this point. Several minutes passed and I realized that I just looked like a girl who desperately had to pee.
“Are you ok in there?” I knocked and asked.
“Actually—could you come in here?” he answered, after a few more minutes of silence. I was secretly very pleased, but I put on an air of concerned professionalism.
He unlocked the door and I entered. Just as I suspected, he was having issues tying up the twine in the back. He had put his pants on top of the thigh-highs and the garter was peeking out around his belly.
“I want to see the stockings,” I said. “After all, I did pick them out!” I truly did want to see them. I had never seen a large man in lingerie before and I found something about the dichotomy between his personality and his outer appearance to be very… sexy.
He turned his back to me and unzipped his pants. He did a great job picking out panties; they fit him nicely. His asscheeks hung out of the bottom, and his ass was actually more toned than I expected. I tied up my twine concoction in a knot so the garter belt would stay up.
“There you go,” I said. “Fits like a glove. I mean a garter. Ha!” I nervously laughed.
He turned around and I stared at him. His flannel was still on, and I could see a giant bulge inside his panties that appeared to be slowly growing. I had never seen a man’s cock inside of dainty women’s panties and I surprisingly really enjoyed the sight of it. His flannel was still on and his jeans were around his ankles. I unbuttoned his shirt, his chest was hairy and his gut was large. He was so manly up top and so delicate on the bottom, and the twine all kind of tied it together, literally and metaphorically. The few men I had sex with in my life were tall and skinny so I assumed that was my “type.” I had no idea I could be attracted to a man like this and I didn’t know a man like this would ever want to wear sheer thigh-highs.
“Take your pants off!” I said. “You’ll see the full ensemble without anything blocking the view.”
“But I don’t have the right shoes,” he sighed.
I looked down and realized he had cowboy boots on, which actually sort of made sense with the outfit.
“I will order some large heels for you, if you’d like. You know… for next time. But I think your cowboy boots look good! It’s not like you’re wearing construction boots or dirty sneakers.”
As he took his pants and shoes off, someone knocked on the door.
“One minute!” I said. Damn it. This was the only bathroom. I thought we were in an actual fitting room for a moment. He went to pull his pants back on and I stopped him.
“Why don’t you walk around the store for a bit in your new clothes? I can hold onto your pants for you; when you want them back just let me know.” I could see a big smile underneath his beard, he took a deep breath and let out a big sigh of relief.
“All right, I can give it a try.” I picked up the pants and we walked out the door… and right into Sandy, who had apparently been standing outside. Shit—was I in trouble?
“He paid for the stockings. I promise.” It was the only thing I could think to say.
“Hon, I know!” She looked at Billy. “Well don’t you look nice!” And she gave him a kiss on the cheek. Dreams really do come true here. An insecure, oversized man was now being admired by a woman twenty years younger and twenty years older than him at the same time.
I went back to the register, giggling. Like I was just caught having sex with someone in my bedroom by my mom, only I was really just tying a piece of twine around a man’s stomach in a public restroom. Billy walked around the store, and I retreated to the register. We kept looking at each other. He flexed his muscles and made funny faces at me. He grabbed random porn DVDs and looked at them and I could see his cock grow inside his panties. He moved his hands around the upper parts of his thigh covered by stockings. He rubbed his hands up and down his legs as far down as he could reach. It sure was a good thing he wore cowboy boots and not heels, or he would have fallen over. He rubbed more and more furiously… and then the stockings ripped. He looked so embarrassed. I rushed over to him to make sure he was ok.