Date with a Sissy

I had no idea what the end result of making a dating profile was going to be. Sure, I wanted to get out there, try and be social for once and maybe even start dating. Getting laid was a distant but nice dream for me, a typical 20 something guy with hobbies that weren't appealing in the aging, fading city I lived in. And of course after setting up the account I got nothing. I wasn't sure how it worked but clearly, hoping for hot chicks to mob me because of my announcement of being available got no results. So I had to see who was in my area, send out greetings that were lame and boring even to me and get nothing back.

I ended up forgetting about the idea of dating after that disappointment, busy with work, digging through my movie backlog and jacking off. Then I got an email alerting me about an unread message on my profile and I hurried to read it, finding it was from a red headed chick named Lorelei who, just from her profile picture I saw she was way out of my league. And further pictures of her left me puzzled but very much interested as to what she saw in me.

Sitting in my worn computer chair, I took my time in constructing an answer, reading each word out loud as I typed it, informing her that I indeed was still single and leaving out the desperation about possessing such a title as a supposed adult. That was nothing compared to still being a virgin but she didn't have to know that quite yet. Or ever, hopefully.

And it worked! She responded and we started messaging back and forth, the discussion gravitating towards movies, a topic I happened to be somewhat knowledgeable about and while I still didn't understand what she saw in me, I tried not to question my luck. Eventually she asked if we could meet up and of course I told her yes, my Saturday evenings were free and usually spent alone. As a janitor at the local community college I didn't have much spare money but thanks to being so boring I'd saved up some cash and there was always the benefit of being able to listen to music or podcasts while working. And that was enough for me.

When the day came I was a nervous wreck and fretted over my clothes, a white button up shirt and new-ish jeans. But it was the best I had and when Lorelei showed up at my apartment in her obviously used car, that made me feel slightly better as we were both on a budget. And seeing her in person? Jesus, she was even prettier than in her pictures! Pale skin only showed off her crimson hair all the more and her tight sleeveless shirt was low cut, showing off so much cleavage. We stared at each other for a second until I hopped in, wondering if she had been checking me out, which would have been a first for sure.

"Oh, do you get into every girl's car that stops here? Or am I just lucky?" She said in a teasing tone and I blushed, making her laugh. "See anything good lately?" And just like that, the conversations we'd had via text were now being traded in person the old fashioned way. I was still smitten by Lorelei but not awed into being mute. Instead I was listening, offering my own understanding on Trainspotting. Of all the first date movies, we were talking about Trainspotting!

We carried on talking about film while at a local Italian restaurant, chatting as if we'd known each other for years instead of days. Nic Cage's vast and uneven body of work was the main subject, with Lorelei waving off Adaptation as being too pretentious and claiming Face/Off was the pinnacle of action movies and maybe even the medium in general. I laughed and mentally cracked my knuckles, ready to venture into what was going to be a knock down, drag out debate.

"Hard Boiled is the best action movie forever and ever, amen." I proclaimed and Lorelei peered at me, a speared meatball pausing in being raised to her mouth.

"Now see, most people don't have the balls to make that claim." She said, glancing around us before leaning closer, voice dropping into an alluring whisper. "I admire the passion." She sat back, looking at me though colored eyelids before smiling, serving as a reminder of how damn pretty she was. 'Soft' was how I can best describe Lorelei, with the dark of her hair, eye shadow and lips contrasting that but not detracting from the allure. "Even if you are wrong."

We debated, I paid and then we walked up and down the idyllic street after, the early fall sunset slow and beautiful as Lorelei took my hand while navigating foot traffic on a cracked sidewalk. I said nothing about it, instead checking out a display window as we walked by, seeing the woman beside me in full.

Lorelei was damn near as tall as I was, five foot ten inches, and with her tight dark blue top and equally snug denim skirt meant her hourglass figure was free for all to see and I noticed quite a few people doing just that, guys and girls alike turning their heads as we walked hand in hand. She had those American Thighs AC/DC had sang about all those years ago, shapely and filled out.

Look, I was desperately horny and Lorelei was a stone cold knock out. Part of it was her confidence and that she wasn't vapid but instead engaging me with movie talk, teasing me about settling for her when my true love was John Woo. I countered by accusing her of wanting to get it on with Nic Cage, which only led to a heavy sigh and a "I wish!" that made me laugh in the deepening dusk.

Only when the streetlights kicked on, the clean light pushing back the night if only in isolated pools, did Lorelei speak again. "Mind if I speak bluntly?" I nodded, not trusting my voice as it surely would have picked the worst possible moment to waver and crack. "Were you hoping to get lucky tonight?" I nodded again, glad for the darkness so maybe she wouldn't see my eyes nearly bug out of my skull. That was blunt alright.

"Same here but we need to talk first." A pause as Lorelei squeezed my hand. "A clarification on my end." Clouds burned red and pink as the sky above us faded from blue to a starless velvet black as Lorelei kept talking.

"I'm the sort of girl who's got to be careful about who I have fun with." I had no idea what that meant but Lorelei pulled me into the mouth of an alley, the street lights not reaching back here and all the sudden we were in a place where crimes always happened in movies, complete with a random puddle.

With a total lack of shame, Lorelei took hold of her skirt hem and pulled it up, revealing dark lacy panties. Swimming in shadows, I don't know what I was supposed to see aside from more temptation, my breathing heavy as I looked into her face. And I thought I saw the glint of reflected light off her chest but it was gone, her voice capturing my attention wholly.

"I've got a little extra down below. If that's a deal breaker then walk away." She sounded miserable as I continued to stand there, my gaze dropping back down to what she exposed. "If you're curious..." She spread her arms and, without hesitation or panic, I went to the submerged in shadow Lorelei.

She was welcoming, pulling me close and her breasts tried to capture my attention before she took one of my hands and raised it to her mouth, kissing it lightly. "I like you, I really do but I need to make sure this isn't an issue." And I let her guide my hand down until I felt that erotic texture of lace panties. Her heat was leaking out and I was familiar with it, having jacked off enough to know that amorous swelter when I felt it.

I didn't wait for Lorelei and instead laid my hand flat against her pubic plain, feeling a hot nub down there which confused me for a moment. Just from Lorelei's words I had a notion of what she was talking about but I didn't know they came in such a small size. And, without thinking about what the fuck I was doing, I rubbed that slight length if only to get a feel for it, to understand what I was dealing with.

A moan from Lorelei snapped me back, aware I was playing with Lorelei's penis in a dark alley, a growing warm spot under my fingers and with her now holding me by the shoulders. Her breathing was harsher now and she started grinding that still soft shaft against my hand and I resumed my motions, getting a deep groan from her of the sort I'd never heard in person before. And the almost pained expression on her face, lips parted and eyes sharp, sexy, both thanking me for this and asking for more.

"Okay..." She moaned, giving no indication that her humping my hand was going to stop anytime soon. "We should go..." Lorelei said, face conflicted until I pulled my hand back and she gave a whine but let loose of me. A deep, shuddering breath and Lorelei pulled down her skirt before unleashing a smile that made me feel like the luckiest guy on the planet. "Whew! I'd say you're okay with me and my uh... Yeah." She said, offering her hand and I took it, talking with her back into the light of civilization and on that buckled sidewalk.

Returning to reality and the glow of light was unwelcome as I wanted more than the tease from the alley. Then the thought that I'd been playing with a dick back there occurred but I didn't stop walking or holding her hand. Sure, I hadn't actually touched it but come on! Lorelei had been not-so-dry-humping me and I'd played along. Glancing over, I saw Lorelei's color was still high and she was smiling, her eyes finding mine as if she knew I was peeking, trying to sort out my thoughts about her, me, then her and me together.

"Sorry, I got carried away back there. I'm not normally that kinda girl but it's been a while." She said while giving my hand a squeeze and I nodded, not having the heart to tell her it'd been never for me. And, there was relief that thanks to being a veteran of jacking off I should be able to cover up at least some of my virgin fumblings.

"I should ask now for obvious reasons: You're an ass guy, right?" I nearly tripped over a jutting piece of sidewalk and found Lorelei's giggling cute as I recovered my balance and composure. All I could do was nod and Lorelei laughed, the sound happy, unconcerned that this talk was happening in public. All I did was sneak a peek at her butt and what I saw confirmed I was indeed whatever Lorelei wanted me to be, as the back of her skirt was rounded out nicely.

Finally, hand in hand, we made it back to the car and Lorelei fired it up, getting us moving towards her place. I wasn't ready when she reached over and placed a hand on my leg, letting it rest there before asking if she could return the favor from the alley. I gave a not quite breathless 'Yeah.' and then Lorelei went right for the goods. Even fully clothed, it was the first time someone who wasn't me touched down there and I jumped while she caressed.

"Someone's excited." She said and I had nothing to reply with so I stayed silent as she kept rubbing my dick. It didn't take long for her to pull into a parking lot and lead me into a brick building, down some dimly lit hallways before unlocking door 117, and letting me in. The living room was dark but she led me to an equally shrouded bedroom, kicking her shoes off while fighting with a lighter to get a single candle burning.

Lorelei was even more attractive by meager firelight, red lips curving into a smile as she slowly shimmied out of her shirt, revealing a black bra that was fighting to contain the bounty therein. God could have shouted my name from on high right then and I would have held up a finger, asking Him to hang on, I had to take this and then continue staring at Lorelei and her almost exposed rack.

"I'd ask if ya like but it's pretty clear ya do." She said and I nodded, understandably mute. She reached behind her and the bra fell away, revealing full bare breasts that were perfect. Perfect roundness, heft balanced with perk, pink nipples with points that betrayed her excitement by standing tall... Seeing Lorelei topless sealed my fate as there was no walking away from that sight. I was hers' and could only watch as she sauntered over, kissing my numb lips and tasting slightly of cherry.

I woke up, having just had my second kiss ever and by the third or fourth Lorelei murmured for me to get handsy and I did just that. For the first time I felt a woman's curves, took her ass in my hands and then just marveled at how she felt so close to me, warm and soft. And when Lorelei asked if I wanted to get more familiar with her boobs, which had been mashed against me during our make out session, I did just that.

I'd whacked it to pictures showcasing cleavage, the curve and shape of boobs having a pull over me that I hadn't been able to reign in. I'm not proud of it but being able to finally feel the real deal was a marvel, a revelation, deep curiosity finally answered. I sucked, groped, caressed and teased as Lorelei held me close, pleased moans and sighs rumbling up from her chest until, after some unknown amount of time her skirt fell to the floor.

Still wholly absorbed in the wonderful paradox of her breasts being soft yet firm at once, I nearly missed when she asked in a low voice if I minded giving her some attention elsewhere. Peeling off her generous chest, I didn't even get to ask what Lorelei meant when she took one of my hands and placed it over a very warm and stubby little thing. It didn't cross my mind as to why she wasn't hard after all we'd been doing, only to rub what she had and was instantly rewarded with more moans and an increasing damp spot on her pure black panties.

"Oh God... Mnnnh..." Lorelei groaned, sounding so satisfied before looking down at me with both kindness and desire with firelight dancing over half of her face, the color there close to the deep crimson of her hair. "Ready for the main event?" She asked in a nearly pained voice and I nodded, Lorelei gesturing towards the bed and so I went. Things were moving so fast and I felt slow and clumsy, having gotten several firsts back to back, one domino falling into the next in line and too, knocking that one over. "Strip please?" She asked and only then did I find my hand that Lorelei had gotten familiar with wasn't dry while I did as she asked in a hurry.

Not that I minded. My memory of that night is clear, from feeling a lingering warmth on my fingers to how amazing Lorelei's heart shaped ass looked while digging in her closet. I marveled at having touched and held that still temptingly clothed part of her as Lorelei turned around, her bare chest instantly snagging my attention as she tossed a large bottle of lube beside me on the bed, followed by a wrapped condom. I knew what to do and started getting ready.

"So I'm guessing this is your first time?" I nodded, not wanting to admit to it but knowing that lying wasn't a good idea when I was this close to getting laid. "Hey, there's nothing wrong with waiting until you meet the right person. Of course, that begs the question if I'm the right person or if we're just really horny." I snickered while rolling the rubber on then began lubing up as Lorelei peeled off her panties and, now naked, climbed on the bed.

"Well? What do you think?" Lorelei extended a hand to me and I gave her the lube, then tried to give a good answer while she was busy preparing herself.

"I... Little bit of both?" Look, saying anything intelligent when Lorelei was naked, within arms reach and giving my dick an approving smirk, was impossible. Because I was seeing the real thing now, that joke about women wanting the D and Lorelei had this sultry slant to her eyes and a small, half smile touching her lips as she poured more lube in her hand then grabbed hold of me. Gasping, I could only watch and feel as she stroked, so taken by pleasure that vision faded somewhat, as if the potency of her touch was overriding the rest of my senses.

"Good answer." Lorelei said, poking me in the chest with a slippery wet finger. "Lay down for me?" I did exactly that, with Lorelei swinging a knee over me and now I was under her. Her still not erect penis was maybe an inch long and the slight bit of loose skin under it must have been what passed for her balls but I didn't ponder on that in the moment. No, there was seeing and reacting, nothing more. Especially when Lorelei grabbed hold of me then thick thighs lowered her body until I felt solid, smooth heat through the condom.

I lay there, breathing hard as Lorelei got us into position, not questioning any of it as my penis touched between her cheeks. Another adjustment and I failed to breathe as she parted around me. Some sound escaped from my lips as all I thought I knew about sex changed in an instant. Lorelei was tight, smooth, hot, gasping, moaning and that ass I'd been admiring was against my hips. I just lay there, seeing the beauty that had taken my dick and virginity in her ass and seemed to be pleased with it.

"Mm, yeah..." She said, rocking to the left and right before pressing down harder on me, that scorching embrace swallowing up all I had to offer. Lorelei tweaked one of her nipples before looking down at me, color high in her cheeks and smiled. "I hope you enjoy the ride." And with that said, she rose oh so slowly before taking all of me back into her, the sensation beyond words and making me cry out loud.

"That's right, let me hear you." I couldn't hold back, especially not when she started going in earnest, the sound of her ass against me ringing out as she picked up the pace. Her breasts jiggled about and the little nub of her dick leaked some but none of that mattered as much as me losing the battle in real time to last as long as possible. Lorelei might have said something but I can't recall, I was lost in this, my first time with another person and when I finally let loose, the orgasm was both familiar and unique. The shuddering flood of pleasure was heightened, more potent, helped along by her ass clamping down on me all the while.

I became aware once again when Lorelei climbed off me, my dick sliding free and listing hard to port like the Leaning Tower of Pisa. My load was trapped in the tip of the condom and it hung there, dangling and off putting. I couldn't do anything about it, too flushed with pleasure and emotion, along with the knowledge I wasn't a virgin anymore. Sure, it wasn't quite how I pictured my first time going but damn, what a ride.

"Here." Lorelei scared me half to death by announcing her return. She was holding a package of wet wipes and used one to unroll the condom then another wipe me clean, their strong, clean smell distinct in the shadowy, small bedroom. Tossing the soiled sheets in a trashcan in the corner, she stood there and I once more admired her. And it was Lorelei's least voluptuous asset that caught my eye and I became aware she was talking while I'd been ogling her.

"If you want to leave after that, I wouldn't blame you..." She said and I wondered, for a second, if she was kicking me out. "Or do you want to..." Lorelei had to have noticed where my gaze was resting and I flushed with heat at the unfinished offer. I'd obviously never had a blow job before but also, I'd never really given much thought to giving one. But Lorelei was so damn attractive and what she had was so... Undemanding? Even now, it wasn't erect or hard but instead still stubby, not hanging down but poking off to the side. I'd never seen it's sort before and was fascinated by this unique part of Lorelei, a fascinating person.

"Yeah? Can we?" I managed to say and Lorelei stepped over to a bedside table, handing me a bottle of water that I nearly drained, handing it back to her to be finished off.

"Sure?" Lorelei said without much conviction but I was working up the will to act on this urge, to not overthink this like everything else in my life. "Should be fine..." She said under her breath but I paid it no mind. Hell, I was freshly laid and the hottest chick I'd ever seen was willing to do more with me. Sanity was on hold and years of horny curiosity, paired with a lovely lady who was willing to indulge me, were now in charge. All that happens next, just remember that I was new to sex and romance was something that happened in movies between attractive people, not me.