Tag: 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 & 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.” Read more »