PANTYMAN!

Chapter Three: My First Day in Lingerie

I picked up the phone and dialed my sister. "Hi Mike", she said, without waiting for me to identify myself. She had also answered on the first ring, almost as if she was waiting for me to call.

"H . . . Hi sis. You were expecting my call? Aunt Frank said I should ask you to tell me something he told you."

"Yes, I WAS expecting your call. Auntie said you'd be calling after you opened your special envelope. But first, you're supposed to describe your clothing to me!"

I was surprised about that, but said "Bluejeans, flannel shirt, white socks, white T-shirt and tennis shoes"

"You're not wearing any underpants?"

"Well, er, yes. Pink nylon panties with lace"

She laughed and said "that's better! How do you like them?"

"Well, it's weird, and it looks REALLY weird, but it actually feels OK, softer and more comfortable than my usual jockey shorts."

"All right! OK, Auntie gave me some instructions for you. I'm supposed to take you to Sweet's Lingerie shop!"

"WHAT?!"

"You'd rather go buy your bra, slip & hose alone?"

I thought about that for all of 3 seconds. "No, of course not! I'd appreciate your help sis."

"That's more like it. OK, I'll be there shortly."

She came to the door half an hour later and let herself in. I was trying to watch TV. Oddly enough "Tootsie" was on. Well, at least I didn't have to worry about guys trying to kiss me! Sharon came into the room and sat down next to me. She put her arm around me and said "poor dear, I know it's a lot to ask from a guy, but you are going to enjoy it! First, drop your pants"

My mouth dropped open, but I stood up and did it.

She smiled sweetly and said "Good! Auntie said you wouldn't need checking up on, but I decided to make sure you conformed to his exact wishes. Your panties are very pretty dear! I love the lace! And the color is definitely you!" she giggled good naturedly.

"Don't have too much fun Sharon!" I said in a mock threatening tone, but couldn't suppress a giggle at the absurdity of the situation.

"OK, now off with the socks and T-shirt! Remember, NO men's underwear of any kind for the next month. And I WILL be checking!"

Wordlessly, I took off my shoes and shirt, then removed my socks and T-shirt. Smiling, she reached into her purse and withdrew a pair of pink ankle socks with fold down lace tops. She tossed them to me. I put them on, knowing better than to object. She reached in her purse again and drew out something pink and silky. It was a silk camisole. I took it from her, and put it on too. It actually fit quite well! I hurriedly put on my pants, shirt and shoes. I stuck my tongue out at her "you couldn't have found any thing MORE feminine, I suppose? Why does this fit so well, I'm a lot bigger than you?"

"I coulda' put you in a lace bodysuit big boy! I had a LITTLE mercy on you. I bought the camisole just for you. Looks like I guessed the size just right! Let's go! Ann is waiting."

She drove me downtown to a little storefront. The sign was simple and said "Sweet's Lingerie Shop". We got out and went in. Ann was the owner there, apparently, and greeted us as soon as we came in. She came over and took my hand intimately, smiling sincerely.

"So, you're Frank's nephew! I'm SO glad to meet you."

Taking me by the arm, she escorted me into the shop. There were a couple of middle-aged women looking around on one side, and a couple of teenage girls on the other. Sharon had gone to another corner and was looking at something.

"You know, your Aunt Frank was my best customer! He told me I might see you in here someday with your sister. Now, how can I help you?"

I was painfully aware that all four of the other females in the shop could easily hear what was being said.

I whispered "I need a bra, slip and some hose".

"What dear, speak up, I'm a little hard of hearing you know!"

I said "I need a bra, slip and some hose" a little louder.

"Eh?" she said, holding her ear closer.

"I NEED SOME LINGERIE!" I said loudly. I heard a burst of giggles. I looked up and the two teenagers were looking right at me, their eyes wide! The little blonde looked at the redhead and ducked her head, covering her mouth and snickering. She pointed at my pink, lacy socks and whispered to the redhead. They both burst into giggles again.

"OK", said Ann, glaring at the girls. "What's your problem girls, lots of men wear lingerie!"

"Don't worry Mike, they'll learn!" The teenagers heard that and looked pained, but one of the middle aged women in the next aisle chimed in and said "That's right! I'm picking out a camisole and tap pant set for my husband right now! He loves this stuff!" The other lady said "See! I told you that was too big for you! You're shopping for Harold huh? How long has THIS been going on?" The teenage girls just shook their heads as if we were all insane.

Ann took me over to the bras first. There were so many styles! It was confusing. "What size do you wear?" she asked.

Startled I said "I have no idea!"

She smiled and told me to hold up my arms. She measured around me close to the bottom of my ribcage. She asked me if I had a style preference, and what size cup I would need. Sharon overheard and came to my rescue. She explained that it was my first time, and that I probably wanted something that would conceal under my male clothes fairly well.

"I also need a full slip and some hose" I chimed in. "Pick out what I need, I have no experience buying lingerie."

"OH, I see! OK, So you need a small cup size in a flesh tone bra without much decoration. She selected one and handed it to me. I followed her over to the slips and she picked one that matched the bra. Then we went over to the hose. Ann suggested opaque black hose — people would probably think they were black socks. I agreed, and Ann handed me a pair. Next we picked out panties. This time I specified pink, thinking they would match the ones I already owned.

The middle aged ladies were in that aisle, and they watched with interest. I blushed, but the lady who was shopping for her husband said "It's OK, dear, don't be ashamed!" She came over and patted my arm. "You wear whatever makes you feel good! Don't be afraid to shop for pretty feminine clothes. If it's what you like, just do it!" I thanked her, and she went back to her friend. I feel like explaining that it wasn't a question of "liking it", or "feeling good", but simply a matter of 10 million dollars.

Sharon took my hand and led me back to the dressing room. She had me strip to my panties, then showed me how to put a bra on. It took me several minutes before I was able to get the clasps fastened behind my back. I was embarrassed and blushing, even in front of my sister. The bra definitely felt weird! I had never felt something even remotely like its silken embrace. Next she showed me how to put the pantyhose on. I gathered all the material up into my hands and slid the right side up my right leg to the knee. Then I did the same for the left leg. Then I stood and alternated legs until I got them pulled all the way up.

The slip I put on with no assistance or explanation. I looked at myself in the mirror and groaned good naturedly "Meet your new sissy brother!" She giggled and said "you look comfy to me. How does it feel?"

I always prized honesty, so I said "actually, it feels very nice! Everything is so soft and comfortable! The bra feels weird, the way it hugs me, and the pantyhose are hugging all of my lower body, all at the same time!"

"What do you think of the way you look?"

"I think I look ridiculous! I will get laughed out of the locker room if I do my workout tomorrow. I probably won't for the next month, for that very reason."

"You plan on stopping after the requirement is over?"

"Of course! You think I'm going to run around in women's underwear for the rest of my life? No way! Not me. Don't get me wrong — it was fine for Aunt Frank, because it made him happy. But it's not something I need to do to be happy!"

"OK, bro! Just curious!". She smiled that odd little I-know-something-you-don't smile again.

I put shoes, pants and shirt back on. Sharon took the camisole and anklets and returned them to her purse.

We left the dressing room and Ann asked how everything fit. I told her everything fit great, and that I needed 3 more of everything. She wanted to know what colors and I told her the same colors as I already had. She clucked at me like a mother hen, but shrugged and did what I asked. We thanked her, I paid for everything, and we left.

On the way back to Frank's house, Sharon said that she was glad it hadn't been my macho brother Don given this mission. She cracked up when I told her that Don would dress like a hooker, get breast implants, and proposition a nun for lesbian sex for the chance at being a millionaire.

Continued in Chapter 4