The Roommate Pt. 02

"Well, yes, I did sneak a peek," he managed in a squeaky voice. "You know, I guess it's a guy thing to want to check out a woman's undies."

"Well, how would you feel if I rummaged through your underwear and wore some of it?" asked Miranda.

Josh wanted to withdraw like a turtle into its shell. "I didn't say I wore your things," he countered.

"But you did, didn't you? I read people pretty well. I have a sixth sense. Does it give you a thrill?"

"I feel like I'm in a shrink's office," said Josh. "Where's your couch?"

"It's true, isn't it," purred Miranda with a smile, shifting comfortably in her chair.

"You also remind me of my older sister," responded Josh, pausing. "I guess I need to tell you the story. It's embarrassing but I suppose you should know. I haven't talked with anyone about this for years, not even past girlfriends."

Josh continued, "I mentioned my older sister because once my mother found out I was secretly wearing her things ... my mother's, that is."

"What things?"

"Oh, lingerie things like panties and bras and nylons, and once in a while, dresses and stuff. Even necklaces and earrings when there was time. Well, my parents got on me about it and shamed me and my older sister especially kept trying to half psych me out, half tease me. I wouldn't admit to her that wearing these things excited me; I would just say I wanted to see how I looked as a girl and take pictures of myself. Anyway, I was so ... "

"Did you look at your girlfriends' things; wear them?"

"I was so, so, so tempted. But for years after I was shamed by my family I suppressed the urge, thinking it was so unnatural and thought it might turn me effeminate."

"Like you'd become gay; what an awful fate," laughed Miranda. "I can't say that I've ever known any women who got off wearing men's underwear. Take Stevie, she has a masculine streak, of course you've noticed, and she's not one to wear dresses, and would prefer wearing athletic sorts of things and short hair, but they just help her define herself."

Miranda looked around the restaurant as though thinking, and then lowered her voice to a confidential level: "Did you used to masturbate while wearing your mother's things?"

"Whew ... Well, I had my first orgasm while wearing my mother's swimming suit. You must really think I'm a perv now."

"I'm not surprised. Look, everyone masturbates, you know. I'm just going to tell you now, Josh, I don't want you sneaking looks at my things, I don't want you wearing them, and I especially don't want you beating off in them. That would be really creepy."

"I never reached that point; I guess I was already feeling too guilty about doing it. But it could've eventually led to it; so maybe it's good you figured things out."

They finished eating and began walking back to the apartment. Josh was relieved she had such a liberal attitude about his peculiar bent. He was developing a new feeling about her - that she was his new big sister and this new big sister had put him on a long leash, sort of.

Arriving back home, and after having shared such a confidence, and with the air cleared, they shared glasses of wine, and then lit up a joint.

"Josh, I think you should indulge this desire of yours. Even though you live in the big city surrounded by people of all sexual and gender types, you've been stifling your pleasure for years, like you're a penitent or something. That's awful, I think."

Something in Josh's prick clicked and a wet-like warmth spread through his genitals, something he wasn't going to tell Miranda about.

"Hmmmmm," he responded.

"I mean, I'll ask you this," continued Miranda, "if you could just totally relax, which the wine and pot have probably helped tonight (giggle), and fantasize, if you could do anything you wanted and everybody was totally supportive, you know, and you could buy whatever you wanted, what would you do with your hots for women's things?"

Josh thought. "I've had fantasies about living by myself in some remote place, and living as a woman, wearing women's clothes all the time, and feeling like a woman. It's so idealized and dreamy. But I've never wanted to be surgically changed to a woman. Having breasts though would be sexy."

"You really do idealize being a woman, without considering all the extra shit that most women go through. But I'll leave that as it is."

Miranda grabbed his hand and pulled him to his feet, and he was slow to yield, considering his wine-and-pot haze. She led him into her bedroom and he wondered if he was about to get lucky. Maybe his revelations had endeared him to her.

She guided him over to her dresser and opened the panty drawer, took them all out, and picked one - a lacey, stretch black pair. Josh's mind seemed headed for another place, like the first time he'd delved into his mother's lingerie.

"You know, Joshy, this panty of mine is too small and I don't wear it anymore, but it might fit you. No, I don't want you to try it on here. Just take it. It's yours. Maybe it will help you blossom. I don't want to overwhelm you ... "

"Yes ... " said Josh, holding the forbidden garment as though it was a stash of diamonds.

" ... but come in my closet. There are some nightgowns I don't wear much anymore. I'm a sucker for buying nightgowns." She pulled three out and lay them out on her messy bed. "They will be a bit large for you, but you might like the feel of them. Just pick one and see how it feels wearing one to bed, that is, if you don't immediately beat off!"

Josh turned red, but that didn't stop him from picking out a short, silky, gold-colored gown with spaghetti straps and stretch bodice.

That night, he wore both the panty and nightgown to bed, but was so sleepy he didn't pleasure himself until the next morning.

His roommate, he realized, must be an angel from heaven. Somehow he needed to repay her generosity.

(To be continued)