Truth or Dare?
The party had wound down around an hour ago, and Felicity and her roommate Olivia were the only ones left.
“Err, truth, I guess,” I responded, hoping to come off casually.
I’d known the two girls for a few years now through work. Both were incredibly attractive. Olivia was strawberry blonde, quite tall for a girl, with awesome long legs and tight arse. Felicity was a bit shorter, with dirty blonde hair and a very tight body. I was hoping that I had a chance with one of them, so playing whatever games they wanted was all part of looking cool.
“Hmmm,” she pondered, staring at me for a few seconds.
“Have you ever worn women’s clothes?” she asked coyly.
I took a swig of my beer. “Err yeah, a few times for fancy dress.”
Both girls lean forward keenly. “Details!” they both demanded.
“Ok, ok,” I said. “I went as an old woman for Halloween one year and then a ballerina a couple of years ago.”
“A ballerina? For Halloween?” Felicity scoffed. “Why that?”
“My ex Becky wanted me too,” I shrugged, trying to play it cool.
“Well, what did you wear?” Olivia asked curiously.
“Err, a white tank top, white leggings, and a pink tutu,” I muttered, starting to blush.
“Oh, cute!” Olivia replied before finishing her wine and standing up. “I’ll get some drinks,” she said, turning towards the kitchen.
Felicity looked intently at me, making me blush even more.
“So, what underwear did you wear?” She asked, smirking at me.
“Hers,” I whispered.
“Her what?” she whispered back, leaning even closer to me.
“One of her lacy thongs,” I admitted blushing harder.
“Mmm, that’s hot.” She bit her lip as she answered before leaning back against the sofa.
The next few rounds passed without incident, although Olivia was starting to look like she was struggling. Eventually, she gave up. “Have fun, kids,” she said with a yawn, “I’m off to bed,” and stumbled her way from the living room.
“Let’s keep playing,” Felicity said with a teasing look before taking a swig of her beer. “Truth or dare?” She asked.
I was slightly nervous about what she might make me do if I picked dare, so I chickened out and went with “Truth,” gulping slightly.
She studied me intently before asking, “How big is your dick?”
I was caught off guard. Answering fancy dress and women’s clothing was one thing, but this was the next level. Besides, I wasn’t exactly blessed in that department.
“Err, about average, I guess,” I stammered nervously.
“Are you sure about that?” Felicity asked. “Cos I’ve heard a slightly different rumor,” she teased.
“Err, ok, maybe a little smaller than average,” I admitted, my face red.
Talking about this with a seriously hot girl was making my cock was rock hard.
“Ha! So you lied earlier! That’s a forfeit for you!” She laughed in triumph. I tried to protest, but she wasn’t having any of it. “I know, you have to get naked as your punishment,” she finally demanded. “And no covering up,” she quickly added.
A hot girl wanted me to strip, so what else was I to do? Blushing deeply, I stripped off my shirt, followed by my jeans and socks, and finally my boxers. My dick was super hard at this point, and I couldn’t look at Felicity in embarrassment.
“A little smaller than average?” she exclaimed. “More like fucking tiny! That’s easily the smallest dick I’ve ever seen! It barely even counts as a dick!” She laughed, pointing at my erect cock. I was so humiliated but so turned on at the same time. “For lying again, you need to be punished,” she said, still laughing. She could definitely tell this was turning me on. Finally, she leaned close to me and said, “That’s what you want. To be punished for lying about your dick size?” she mocked.
I nodded, still looking at the floor.
“Ok,” she smirked. “My room, now.”
She gathered up our drinks before heading upstairs to her bedroom. I followed her, staring at her ass all the way, wondering what on earth I was letting myself in for, but also not believing my luck at having her take an interest in me.
“Now, I think that you should work for your forgiveness,” she said once we were in her room. “Kneel in front of me,” she said sternly.
I knelt there, looking up at her, my little dick excited. Slowly she began to undress. A smirk etched on her beautiful face. She pulled her dress over her head, revealing a black lacy thong and matching bra. I was in heaven. She reached behind her back and undid her bra, letting it fall onto the ground. Her tits were amazing. Pert, a good size, with pink nipples that were super pointy. Slowly, she pushed her thong down her legs, revealing her pussy to me. Her pubes were trimmed neatly into a triangle that pointed down to her clit, and from my position at her feet, I could tell that she was soaked.
“Put my thong on,” she demanded.
I slid her thong up over my legs. It was wet. The small bit of fabric perfectly fit my small cock and balls, which Felicity found hilarious.
“Looking good,” she teased before pushing me back down onto my knees.
“Ok, close your eyes. I want this to be a surprise,” she said slowly.
I closed my eyes shut, not believing this was happening. A couple of minutes went by, and I could hear her giggling in excitement.
“Ok, now open them for me.”
I did as she said, and inches from my face was a purple dildo sticking out of a black leather harness she was now sporting.
“You look so good in my girly knickers that I think you should be my little slut. What do you think?” she asked mockingly. “After all, your dick is basically a little clitty. It’s so small, so get on your knees, and suck my cock!”
Her tone left no room for arguing, and before I knew what was happening, I was sucking on her strapon dildo. I gagged and spat and licked her cock, caught up in the moment. She was standing over me, her hands in my hair pushing me deeper, a look of absolute lust on her face.
“Yeah, fucking suck that cock, you little sissy bitch” she laughed, thrusting her cock into my mouth.
She fucked my face for what felt like an age, her cock filling my mouth and hitting the back of my throat. I looked up at her as I gagged to see her thoroughly enjoying herself, her mouth split in a mad grin. Then, finally, she pulled the dick out of my mouth and turned around.
“That got me all hot and bothered,” she told me as she presented her arse to me. “Now lick my arse.”
She stuck her bum out as she bent over, her tight puckered hole inches from my face. Tentatively, I ran my tongue across her hole. Thankfully it tasted as she had freshly cleaned herself. As I probed her hole gently, she moaned for more. Then, encouraged by what I was doing to her, I picked up my pace and went to town on her arsehole. My hands gripped her tight arse cheeks, spreading them. My tongue was buried inside her, flicking over her hole then back in, covering her insides with my spit.
“Mmm, yeah,” she moaned passionately as her hand found her pussy. “Lick my fucking arse.”
I obeyed. This was so dirty. I couldn’t believe my luck. My cock was straining against her small thong, begging for release.
“Keep going. I’m going to cum!” she demanded, pushing her arse harder against my face. “Yes, yes YES!”
She finished, as she pulled away from me again, a massive grin on her face as she turned around to face me again.
“Fuck, that was amazing, you dirty little bitch.”
She laughed. She looked down at my cock, examining it intently.
“Hmm, looks like your little dick needs some attention, doesn’t it?” she whispered, pulling me to my feet before pushing me onto her bed.
She spread my legs and ran her finger down the length of my dick, eliciting a shiver. She cupped my balls, then continued further down, sliding her finger up against my own hole. I was so turned on I was helpless to resist as she slid a lubed-up finger inside me.
“Oh, you’re a dirty little anal slut, aren’t you, sissy?” she whispered in my ear as she fingered my hole.
All I could do was nod as she probed me.
“You want my cock up your arse?” she continued seductively.
I gulped, then nodded. She grinned again as she pulled away and lubed up her cock. She was kneeling between my legs now, slowly stroking her dildo and staring at me with an intense stare. She pushed my legs up over her shoulders and rubbed her strapon-on against my hole, coating it in lube.
“Beg for it,” she demanded, leaning right over me. “Beg for my cock up your arse.”
“Please… Fuck my arse,” I begged, needing to be dominated even more by her.
She had me in a trance, everything she had said and done so far had me ready to burst, and I would do anything for her. Slowly, far too slowly, she edged her way into me. First the tip, then finally, finally the full length of her dildo. I was speechless as I was touched in ways I’d never imagined. Fucking hell. This was incredible. Gradually she started to move, thrusting gently into me.
“Fuck,” I let out, drawing a laugh from her.
“Ooo, my little sissy slut likes a big cock up his arse?” she asked cruelly.
All I could do was nod. She started to pick up speed now, hammering into me. The harness must have been rubbing up against her clit as she was moaning away on top of me. That or she was getting off on the power trip. It was hard to tell. I could barely concentrate on anything other than not cumming too quickly. I wanted to savor this feeling. It was so intense.
She was lifting my hips now, propping me up on my shoulders, her tits dancing in front of my face as she pounded into me, putting me into a position I’d never tried to get into. Holy fuck. I was going to cum right on my own face! I tried to protest, but as soon as I opened my mouth, all that came out was a series of high-pitched moans as she continued fucking my arse.
“Oh oh oh oh… FUCK” I moaned.
I came. My little dick spurting a stream of hot cum right onto my face. I must have looked like a proper dirty slut. I collapsed onto the bed as she pulled out, leaving me empty.
“Mmm,” she said, savoring the image in front of her. “That was amazing, sissy,” she said as she turned and walked away, sauntering off to her bathroom and leaving me to pass out in a mess of sweat and cum.
*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.