“Truth or Dare?” [MF] [Str8] [anal]

Isabelle’s face flushed a deep cherry red, something I’d never seen happen in over 8 years of friendship. She didn’t otherwise appear anxious to end the dare, especially considering she kept her bare breasts pushed up against the glass of the window, which faced the street, outside her small studio apartment. I wondered if she was attempting to put on a brave face, to not risk her reputation of consistently remaining cool and unfazed. I wouldn’t have doubted her calm demeanor if it weren’t for her blushing cheeks being an obvious giveaway that she was extremely uncomfortable. I realized that I had maybe taken things too far. I had become so accustomed to thinking of Isabelle as having unshakeable confidence, that I hadn’t even considered that I had potentially just set her up to either turn down a challenge, which is unheard of for Belle, or to do something that apparently managed to humiliate the most unflappable, self-assured person I know. And, I just didn’t feel right about either possibility.

“Okay, okay.. you’re good!” I said, trying to sound satisfied as if I’d seen enough to conclude that she’d succeeded in meeting my challenge.
“What?…” She turned just her head towards me but kept her chest pressed up against the windowpane. She honestly looked to be more confused than relieved, “He hasn’t even looked up or noticed me standing here yet!”
I furrowed my brow at her, but she turned her attention back to the mailman as he approached her building’s walkway.
“Damnit, he won’t look up… he just keeps staring at the mail in his hands!” she moaned managing to feign genuine disappointment, while her beet red coloring continued to expose her nervousness. I was impressed by the level of commitment she was showing.

“He’s taking too long!” I said attempting to offer an out. An odd, totally foreign feeling of possessiveness momentarily came over me, causing me to blurt out, “I didn’t think daring you to press your bare boobs on the glass until the mailman walks up and sees you, was going to end up with you having to stand there exposing your perfect tits to the world for fucking hours!”
She took a step back from the window and pulled her cropped, tie-dye t-shirt back down over her breasts, and smiled at me, seeming amused.
“Perfect tits, hmm? And why do you sound… jealous?” she teased. I was glad she was back to her secure and cheeky self. Thankfully before I had to explain my descriptive wording that revealed more than I intended, the conversation was interrupted by the sound of her mailbox being opened. “Of course, now he’s here looking right at me and my tits are hidden away…” she said as she smiled cordially at him through the window and they exchanged quick waves. As he turned around, to head back to his truck, she looked up at me and her grin widened, “Poor guy has terrible timing… a couple of seconds faster and he would’ve been blessed by an eye full of these perfect tits…” She pulled up her top again, quickly flashing me, causing my cock to jump up and it took everything in me to distract and block the incoming explicit thoughts.

“Wow, you suddenly sure aren’t too shy or embarrassed to have your boobs out now!” I blurted out, without thinking. She just stared at me for a few, painfully quiet seconds; as my mind scrambled to think of how to fix this. I was certain I’d just taken what I’d recognized to be a clearly awkward situation (which I’d put her in, of course) and then I’d unintentionally mocked her for the rare nervousness and uncertainty it caused her to feel.

“When was I EVER embarrassed to show my boobs?!” she asked. There wasn’t any anger in her voice and if I hadn’t seen the intense color change to her otherwise perfect complexion, I never would’ve imagined her to be feeling anything less than confident under the surface.

“Well…” I began, becoming less certain of my observation and the assumptions I’d previously gleaned, “When you were doing the dare, you clearly were a bit… shy or felt funny about the situation.” She lifted one eyebrow at me, but still said nothing, so I continued. “You were blushing so, so much and you kept your eyes shut tightly, only peeking every once in a while, I guess to track how much closer the mailman was getting… and I wouldn’t have dared you to do that if I knew…” My guilt-wracked monologue was abruptly silenced by Isabelle when she erupted into laughter. I waited for her to explain, but she’d stop laughing for a second, attempt to catch her breath; only to then be overcome with giggles again.
“What is so funny about that?” I demanded.

She sucked in a few deep breaths of air, before beginning to explain, “I wasn’t blushing out of humiliation, Lucas! I genuinely enjoy being an exhibitionist, showing off my tits… I mean, you said yourself that they are per…”

“Alright, it’s been made clear that I think they are fantastic,” I interjected before she could finish teasing me. “I’m never going to hear the end of that, am I?! Well while we’re at it, I might as well put it all on the table now…” I could feel the confession pouring out of my mouth as though I had no control to stop it. “Yes you are out-of-this-world gorgeous with an epic pair of tits, but honestly, coming from an ass-man, your butt is somehow even better.” She didn’t say anything, but her smile was genuine and she wiggled her eyebrows at me in a playfully suggestive manner. I quickly attempted to return to the previously derailed subject, and get an answer from her. “Okay well, I’m, at least, really relieved to know I didn’t accidentally make you do something upsetting, that made you feel insecure. But, then what was going on with you, Bells?”

Her smile turned a bit mischievous as she looked me in the eyes and explained, “I don’t turn red like that from nervousness. I get hot and flushed when I’m insanely turned on!” My cock stiffened at this revelation and my mind began to race, as she continued. “I really like the idea of people watching me and seeing my naked body, knowing that they are getting hard. And even more so if it’s a situation where they feel like they need to keep composed, and not let on how much they’d like to bend me over and fuck me.” I shifted in my seat, feeling myself get harder with each word. She glanced down towards my lap and her sideways grin twitched with excitement, clearly knowing the effect she was having on me.

“So, is it just because he’s a stranger?” I asked, trying desperately not to let on to the twinge of jealousy I was feeling. I had inadvertently set up some lucky bastard to be the focus of her intense exhibitionist fantasy, and I was surprised and ashamed of how much I envied anyone affecting Isabelle in such a way, even if he was completely oblivious of it. I tried to play off my interest as casual curiosity, as I pressed her to explain further, “Or do you have a bit of an attraction to your mailman,” my voice started trailing off; I wasn’t particularly proud of the way I sounded, but I continued on, “who I only chose because I saw his truck pull up just as I was deciding what your dare was going to be…”

She shook her head gently while keeping her stare connected with mine and said, “While it would’ve been hilarious to see his shocked reaction once he was within a foot or so of my bare nipples squished against the glass, it wasn’t the mailman seeing me that had me, quite literally, hot and bothered. It was you, idiot.” She paused for a few seconds to inspect my reaction, but when I stayed quiet she continued, “And, I was closing my eyes because I didn’t want you to feel self-conscious about staring and so, I figured if I wasn’t looking, you could ogle me all you want; maybe even touch your cock as you looked…. if you couldn’t stop yourself.” I was stunned and unsure of what to say. So I was grateful when she continued on, “My mailman always takes forever to deliver the mail, and at first, I was just looking forward to shocking the hell out of him; but then it dawned on me that you were able to see me topless, too. And, even though we’ve never crossed that line before because we’ve always remained platonic; it was making me so fucking wet imagining you watching on, and trying unsuccessfully to not let on how hard it was making you!”

“Was it really that obvious? I thought I’d been pretty stealthy about how worked up you were getting me…” I laughed a bit uncomfortably.

“Yes it was immediately evident to me, but I liked it,” she reassured me. “Honestly, it’s pretty crazy that we’ve been friends all these years and we haven’t hooked up. We’re both attractive, cool people who have a great time together…”

“And we’re so modest too!” I said laughing. Then I continued, a bit more seriously, “I think in the past, we’ve always kept our feelings from going that direction because we were in relationships, or dating other people.”

She nodded in agreement, “I always appreciated and respected you for not hitting on me when it would’ve been inappropriate due to circumstances. But, things feel different now that we’re both actually single at the same time..” she hesitated, but smiled before continuing, “and I think the fact you weren’t constantly trying to fuck me, has always made me want you that much more.”

“It’s not like I haven’t fantasized about it…”I admitted.

“Oh ya? In these fantasies, what would you want to do to me most of all?” Her question made my heart race a bit. I pretended to think it over, even though I immediately knew the answer. “Oh come on.. you know what it is!” she said, seeming to read my mind.

“I’d want to fuck that incredible ass of yours…” I said with firm commanding confidence that surprised even me. I didn’t want her to assume that was a proposition, especially an unfavorable one. So I quickly cut the overwhelming sexual tension saying, “Wait a second, you just got an answer to a “truth” basically, so it’s your turn again!”

“No way,” she protested, “You slipped up and gave me that info as a freebie! It’s still your turn! Truth or dare?”

I sighed heavily before giving in, “Well, I’m not revealing any more secrets, so “dare” it is.”

She smiled that devious lopsided grin of hers and boldly announced her challenge to me: “I ‘dare’ you to fuck me in the ass.”

I toss her a quizzical look and wait for her to say or do something that will clue me in on how serious she is being. I assume at any moment there will be an inevitable fit of laughter from Belle, mocking my gullibility, while also crushing any hope that it had been an honest offer.
My mind begins to search for alternative scenarios that could better explain this opportunity for something I’d previously thought of as ‘out of reach’, it just seemed too good to be true. ‘Was she just messing with me? Or maybe she’s drunker than I realized? She did just break up with Travis, maybe this is her attempt at a revenge fuck?’ The optimistic part of my brain tries to counter these doubt-filled conclusions, in an attempt to rationalize them away. ‘She definitely sounded sincere and she can’t be all that inebriated, she’s only halfway through her first beer. Also, even if I am just a rebound, who car..’

Acknowledging my obvious hesitation, she interrupted my confused inner monologue saying, “Travis, I’m serious!” She took a few steps to bring her curvaceous body within inches of mine. “I’ve always thought you were hot, and I’ve imagined what it’d be like to feel your mouth on me… and to have you inside me.” The deep blush returned to her makeup-free face, and the newly gained context of what caused that specific physical response in her sent a rush of blood to my now achingly hard cock. I could feel my erection pushing into the tightening restraint of my clothes. Isabelle also noticed apparently; she gave me a half-cocked smile and I followed her eyes down to my where my erection’s outline was clearly visible through my dark blue jeans.

Before I could say anything, she reached her hand over and firmly gripped my shaft through my pants. Her hazel eyes lit up with delight as she exclaimed, “Holy shit, Lucas! Your cock is fucking huge!” It was something I’d obviously heard before, but it never really got old. Her fingers lingered at my groin and the rapid-fire squeezes she gave me through the denim fabric provoked my mind to come up with a personal dirty-pictureshow depicting me bending her over and giving her exactly what she’d asked for.
It was obvious we were both wanting this to happen, we just needed things to get past the awkwardness of someone making the first move. She’d initially got things started with her bold dare, so now it was my turn to progress the situation.
I encouraged her to indulge her curiosity saying, “You want to see it, don’t you?” She nodded emphatically, biting her lower lip. Any remaining concern of her not being serious was immediately erased by the expression of overwhelming desire mixed with a ravenous hunger that she was now giving me.
I offered a suggestive nod to Belle as a gesture to unzip my pants and get it out. She excitedly pulled at my clothes, leaving them bunched up around my ankles. She didn’t wait for any more instructions from me; instead, beginning to run her fingertips down the length of my shaft, sending a chill through my entire body.

“I, usually, would want to get you excited by going down on you for a bit, but you’re already rock hard,” she marveled, never taking her eyes off my member. “We’ve basically had 8 years of foreplay and now I’m aching for you to be inside me.” She spits into her open hand and then held the tip of my cock. “This should help you slide into my ass a bit easier,” she said circling the head with her lubricated palm; almost like she was chalking a pool cue.

She unbuttoned her tight, high-waisted jeans and wiggled out of them; leaving them behind as she made her way over to the backside of her sofa. She draped her upper body over the back of it, presenting her shapely, round bum for me to take from behind. I pressed my face in between her pillowy cheeks and used long flat laps from my tongue starting at her pink puffy pussy lips and all the way up the crack of her bum. I then focused on the area that held the most interest to me, tickling her tight anal opening with circling licks, causing her knees to buckle a bit and quiver with anticipation. “Fuck that feels so good…” she said in a breathy whisper. I continued my teasing by inserting the pointed tip of my tongue into her hole, penetrating it deeper until my mouth was pressed up against her and I was french-kissing her behind. She was moaning and pushing her butt into my face. I stood back up, the blood pulsing through my shaft, holding it in one hand and pushing my other open palm into the small of her back. I lightly teased her with the tip of cock as I slid it around the puckered pink skin of her asshole. I pushed very lightly at its entrance and imagined the resistance it held to be a good indication of how tight it would feel inside. This thought immediately caused pre-cum to dribble from my dickhead.

Still gripping the back of the couch, Isabelle turned her head to look at me over her shoulder, revealing her beet red complexion. “Fuck me already, Lucas… please!” she demanded. I was insanely turned on by the level of both aggression and desperation in her voice. I spit once more on the entrance of her ass before finally pushing myself into her, causing her to let out a slightly surprised yelp.

I continued to slowly push until my hips were pressed up against her butt. I moved my hands to her sides, feeling her hipbones under my fingers, as I built up a steady rhythm sliding in and out. She still felt tense and I could feel her muscles clenching around me inside her. Physically it was an amazing experience; different than what I was used to with oral or vaginal sex. It was significantly less wet, but there was a completely new sensation; it felt like her ass was grabbing my dick and pulling me in deeper; it was incredible.

I wanted it to feel just as good for Isabelle, and I could see her face flash a slightly pained look even as I tried to fuck her with less intensity. I pulled out of her and took her hands; leading her to the bed, “I want to keep fucking your ass because it feels better than anything I’ve experienced before, but I want to look at you and kiss you while doing it.” I said as we both climbed onto her Queen-sized mattress, “and most importantly, I want it to feel good for you too.”

She nodded and smiled her endearing lopsided smirk, “Well then, I think I know what would help…” she quickly turned to her bedside table and rummaged through a drawer. After a moment, she triumphantly held up a small bottle of lube and a vibrating bullet.

We lay facing each other on our sides, with her knees pulled up near her chest. I slid back inside her, this time with significantly more ease. In this position, she had perfect access to play with herself while I fucked her ass. I took full advantage of the gained ability to look into her hazel eyes which were currently filled with desire, to kiss her naturally pouty lips, or to play with her perky C-cup breasts.
She pressed the soles of her feet into my thighs, guiding the speed and depth of my thrusting. She turned on the vibrator, causing it to buzz impressively for its small size; and then held it to her exposed clit. As soon as it made contact with her body, her almond-shaped eyes widened and she sucked in several quick breaths. Her hips were now bucking in rhythm with mine, indicating she could take me in further. So, I began to push deeper, until we were pressed tightly together and then pulling my cock almost all the way out, leaving only the very tip inside her. I fucked her like this for a bit, watching my shaft slip in and out of her asshole. I was thoroughly enjoying the sights and the feeling of both of her sphincters tightening around me, with increasing pressure as the toy stimulated her closer to cumming.

“I want you to fuck me harder..” she demands suddenly, “Because I’m so close.” I snake one of my arm’s around the back of her neck and grip her protruding hipbone with my free hand, holding her tightly as I begin to fuck her more roughly. Isabelle begins to curse in between loud moans. Her insides are gripping me with a force I’ve never felt and I know I won’t be able to hold on for too long. Just then, her panting gets frantic as she pulls the vibrator away and begins using her hand to rub herself, “Oh my fucking god!” she exclaims as she looks down to see a gush of liquid begin to erupt from her pussy. “Holy shit, I’m squirting!! Don’t stop, Lucas!” I can feel the warmth of her juices flowing over me, and I watch her lift her squirt-covered fingers to her mouth to taste them. Her eyes light up, as she dips them back in her still flowing pussy. “You have to taste this!” she says with excitement. I allow her to push her fingers into my open mouth, and I am surprised by the sugary sweetness of her squirt.

I soon realize that I’m seconds away from orgasm. “I want to finish your mouth, so you get a taste of my cum too.” Nodding in confirmation, she allows me to pull myself all the way out.
Kneeling on the bed in front of Belle, while she’s laying on her stomach, I just watch as she strokes my cock with both hands. I can feel my orgasm building and her expert hand movements feel like they are squeezing the impending load out of me. I’m nearly brought to the edge watching her lick and suck my cock, with enthusiasm.

“I’m gonna cum..” I warn, before letting a long moan escape. I look into Belle’s eyes, the girl who has secretly driving me crazy for years. She presents her eager mouth to me and I climax harder than I ever have before. I unleash multiple spurts of hot, white cum onto her protruding tongue and down her open throat. She then closes her lips tightly around my tip, sucking out the last, final drops.

Finally collapsing onto my back, I’m lightheaded and nearly out of breath. I affectionately kiss the top of her head as she wiggles her way up next to me.
“That was unbelievable, but now it’s back to you…” I begin slowly. She looks up towards me expectantly, and I pause to attempt an impersonation of her signature mischievous, lopsided grin. After allowing her curiousity to build for just a moment, I pose the obvious following question, “Truth or dare?”

Source: reddit.com/r/sexystories/comments/p9p3vs/truth_or_dare_mf_str8_anal