It started out so innocently, honest!
I share quite a nice apartment with the lovely Sarah. She is, while gorgeous and an old friend, a bit of a slob. I had just done a load of washing and after folding mine, decided that rather than have hers left in the basket on the coffee table for the next few days, decided to fold hers as well as the subtlest of hints.
Things were going perfectly well until I got to a red silky panties. "How the hell do you fold these?" I remember thinking to myself, idly fondling the fabric, which somehow led to "I wonder what these feel like on?"
I had seriously never in my life entertained the fantasy of wearing my women's underwear, but it was a slow afternoon and Sarah wasn't due home for hours and that was how, inevitably, I was busted by my housemate on the couch stroking my erection on the couch wearing nothing but her red silky g-string.
"This," she said, putting down her bag, "is unexpected. I need a drink. Want one?"
"Sure." I croaked, as mortified as it's possible to be while still breathing, "I'll just..."
I made to get up off the couch and rush to my room to slip into something more comfortable, which is surprisingly difficult with both hands covering your genitals.
"No, stay there!" said Sarah, grabbing a couple of beers our of the fridge. "Under the circumstances, you'll understand if I'm not letting my underwear out of my sight."
She handed me a beer, smirking when I had to take one hand off my groin, and sat down facing me.
"So, Dan, how long have you been wearing my panties?" She waved her beer at the g-string with its rapidly deflating contents.
"Sarah, you have to believe me, I have never, would never - well okay this once, but honestly, it just seemed like a... good idea at the time. I promise I'll handwash them and we can just forget this ever happened."
She raised an eyebrow and quirked a smile. "Dan, I just walked in on you having a wank in my underpants. It's going to take a bit of effort on your part to smooth things over."
She sat back and sipped her beer, crossing her long legs in her tight business skirt. God, she was sexy. I had wanted to take our relationship to the next level for a while now, but this seemed to be the end of that dream, and I wasn't sure how our friendship could ever recover.
"Look," she said, "There's nothing wrong with a bit of kink, if you'd simply asked to try on my panties..."
On saying "panties", she cracked up laughing. After a few moments, I did too and when we settled down a bit, it felt like some of our friendship had been restored, then her expression grew pensive.
"Tell you what, Dan, how about we make it a kink-for-kink deal. I've always had a couple of things I've been wanting to try, so how about you give a friend a hand and we'll call it even?"
My throat went dry. "I'll be wanting a few details."
"You remember Mark?"
I nodded, Mark was her boyfriend from a couple of years back. I hated that guy.
"Well, he had a bit of a thing for spanking my bare ass."
"Yes, I heard." She blushed a bit then. The walls of the apartment weren't all that thick and I recalled wanking myself silly to the ripe smacking of palm and sometimes wood on her shapely naked ass and her squeals and moans.
"I would be more than happy to spank your bare ass, Sarah."
"Actually, while that might be fun, I was more interested in quite the reverse."
My mental image of Sarah bare-assed over my lap, legs kicking flipped, and was strangely even more exciting.
"Well, someone's eager!" Sarah glanced pointedly at my rapidly growing erection, which I awkwardly attempted to conceal one-handed. "So I can spank you?"
"What exactly are we talking about here?"
"Well, a good whacking with my hand then a bit of a seeing to with my hairbrush."
"Your hairbrush?" It was a big solid wooden beast of a hairbrush. I remember her getting pretty noisy when it sounded like Mark had the hairbrush in play. "That's going to hurt!"
I realised I'd said "going to" at the same time she did. She grinned broadly.
"It's a spanking, Dan, it's meant to hurt."
"Fine," I said, trying to mask my growing excitement. "Where do you want me?"
"Just like that? Well, this has been quite the afternoon. Okay, stand up!"
I obeyed. She was rubbing her hands together with glee.
"Hands on your head! No point being shy!"
Her eyes dropped to my erection poking out of her underwear.
"Go and fetch my hairbrush from my dresser, you naughty boy, and no rummaging through my underwear drawer on the way, or it will go worse for your bottom!"
I scurried off, terribly conscious of her eyes on my be-G-stringed backside. I crept into her room and picked up her heavy wooden hairbrush, slapping its oval back into my palm. Holy shit it was solid! A worm of fear mingled with my heady mix of horny humiliation. I caught a glimpse of my smooth, pale backside in her mirror and gently ran my fingers over it, trying to imagine its introduction to Sarah's hairbrush in a very short time.
"Come on, time for your spanking!" Sarah called from the living room, clapping her hands.
I didn't know exactly how to hold the hairbrush. It seemed wrong to hold it by the handle so I cupped it in both hands and presented it to Sarah, lending a strangely reverential air to proceedings. She had taken my spot in the centre of the couch. She patted the cushion to her right eagerly. I sat and she put her arm around my shoulders.
"Well, Dan, I must admit today has escalated rather quickly. Now I am pretty pissed off at you for wearing my undies without asking, and I do think a spanking would help clear the air, but let's face it, this must be pretty humiliating already, so we're probably even. If you want to back out you can. That said, I really want to spank your cute little butt and just to be clear, it's going to hurt."
"Sarah, I'm really sorry I tried on your underpants and even sorrier you busted me wanking in them. It was a spur of the moment thing and in the spirit of trying anything once. I am willing to offer my ass for a damn good spanking. Anyway, this is already the most embarrassing day of my life already so let's just do it. Just one request."
