Storytime

"Hey Jack, come on in. I have to tell you; I've really been looking forward to tonight's Storytime. I'm curious to find out what you think of my effort. Please help yourself to a drink... and could you fix me a 7&7?"

"You got it Mary, and I gotta tell you, I think I've got the winner tonight!"

Mary ducked into the bathroom with an over-the-shoulder "Just give me a minute and I'll be ready."

My confidence in my story was genuine, but I was also trying to light a fuse. She knew the kinds of stories I liked best - edgy and kinky. Mary's stories tended toward the romantic. They were often more cerebral, exploring things like the power dynamics of relationships. But I was convinced the kind she enjoyed most were the hot and nasty ones. By telling her I had cooked up a good one... well, with any luck she was in the bathroom getting ready via more than just a quick pee.

Mary entered her living room as I picked up where I left off: "I've been looking forward to getting your reaction to this story ever since I worked out the basic concept."

Talk about an understatement! In truth, Mary's reaction was the only thing that would define winning for me tonight. Writing this story had taken twice as long as normal due to the frequent breaks I needed, as my mind wandered off the storyline and into the reaction I hoped to elicit from Mary. Squirming, surreptitious touches, maybe even panty soaking. I had to admit, it would be a pretty big leap from the confines of our current relationship. So far, our friendship has been based on a shared intellect and a mutual appreciation for each other's life experiences. Both in our late 40's, we had each led an adventurous life and neither was ready for pasture.

About a year ago, one of our conversations had wandered into the area of porn, and we reminisced about how much it had changed over the years, from the sparse pickings of men's magazines to the cornucopia now online. Once the discussion landed on erotic stories, the Literotica website came up and we both confessed to being fans. Through sharing some favorites, we found we had similar thoughts and observations on the various writing styles (not to mention pet peeves of grammar and vocabulary). It became apparent that we shared a literary bent that led us to want to try our hand at writing our own.

Now we get together every month or so, whenever we both have a completed story to share. The first few Storytimes amounted to little more than reading our works to each other and sharing thoughts on how to improve them. Lately it had become a good-natured competition to decide which story was better, and which were good enough to submit to the Literotica website. It was also an opportunity for both of us to learn from each other and stretch as writers. Tonight I was adding an additional objective -- to see if I might also be able to stretch Mary in other ways.

"Coin flip to see who goes first?" Mary asked.

"Sure", I said.

"What's your pleasure, head or tail?"

"Oh, c'mon, you didn't really say that? Are you trying to make it hard already? I think you know me well enough to know that I'll take whatever I can get!"

"Okay, slow down there, tiger. In that case I'll call it - heads" she said, with a quick flip. "And heads it is! All right Jackie boy, sit back and listen to this one."

* * * * Best Laid Plans (Mary's Story) * * * *

Here I was, waiting in my hotel room, so horny I was beside myself, aware that I was about to have sex with someone I had met only a few short hours ago... just like I had planned it. Except not -- not at all! This was so different from what I had in mind. I had imagined stepping out of my accustomed role, the one where I chose the man without letting him realize it, then followed their lead the rest of the way. And while tonight didn't go like that, it also sure didn't go like I had scripted it. In my steamy one-act play, I fancied myself a huntress, the single woman on the prowl, choosing a man and taking him to bed. I would be the one in obvious control throughout, following my script. Now that script was out the window and control seemed a distant memory. Not only had I not chosen the man, there wasn't a man at all! Instead, the most amazing woman...

When the third and final day of the conference ended, I had one last night in this huge upscale hotel, this prime hunting ground. Three different bars to choose from and no need to drive to get back to my liar. Trying the first bar, I hadn't even completed an initial scan of the room when the cocktail waitress came up from behind me.

"Hi, I'm Chris, what can I get you this evening?"

Wham! It's just like when someone tells you about their traffic accident... 'I swear, she came out of nowhere'. I felt it as soon as our eyes met. A kind of energy, different from anything I had felt before. It put me off balance, set me back on my heels.

"Uuuhh... Hi. Hi Chris, I'm Amy. Nice to meet you. I'll have a gin and tonic please."

Thank God for verbal autopilot! As she made her way back to the bar I stared, dumb struck. She moved so smoothly, the swaying of her short skirt suggesting a firm round ass hidden beneath. Supported by a pair of very toned looking legs. When she made her way back with my drink, I had my first chance to see the rest of her: very small breasts, tiny waist above the slightest hint of hip flare, all in a package that barely topped 5' tall. She looked to be a decade younger than me; probably mid-to-late 20s. In my mind I pictured a gymnast, stepping to the mat to begin her floor exercises.

I was already gone; I was just too rattled to realize it yet. Over the course of my next two drinks (and more of her time than any customer would normally get), Chris and I enjoyed easy conversation, then started adding a bit of playful banter. Eventually we evolved into boldface flirting. By the time Chris let me know her shift ended at 10 PM it was already 9:40 and I realized I was fairly intoxicated, but it had very little to do with the alcohol. Declining another refill, I cringed inwardly at my lame joke about how I wouldn't say no to room service from the bar later, but the smile I got in return let me know all I needed. I paid the tab with my room number and made my way back there, feeling the need to calm my libido and take stock of the situation.

Up until now I had never done anything with another woman. Sure, I had the typical curiosity... could sex with another woman really be better? Oral with someone who knew first-hand how everything worked? Or maybe it had to do more with a certain emotional resonance, like a two-part harmony. And why her -- why Chris? Undeniably there was an allure to the contrast of our bodies; me being 5'7" and having a shape nowadays described as "curvy", what used to be called "classic hourglass". And Chris being so much smaller, firm where I was soft, angled where I was round. Picturing our bodies together; the attraction of opposites, was undeniably hot! While that was all true, in the end it was just a very rich icing on the cake. Underlying everything for me was that energy she gave off. It flowed into me like it was filling a void. And it was something I had never felt before in another woman. That was why I wanted Chris. Realizing that dispelled my confusion and gave me a sense of calm. Now I was no longer horny and anxious. I was horny and eager!

Finally, the knock came. "Room service!"

I smiled as I opened the door. There she was, smiling back, so cute, so innocent. I took a few steps back to allow her entry. The door shut behind her and she wordlessly closed the distance between us. Our eyes were locked as our hands began to slowly caress, feeling the energy, the electricity. I had an overwhelming desire to kiss her, but I held off, partly because the intensity of her tender touches was already threatening to overload my senses. It seemed like kissing her might cause us to burst into flames. When our mouths did meet, I pushed my tongue into her, beginning the slow, sensuous dance of exploration. Her body was so slender, yet so firm -- the toned muscles moving as her arms pulled me in.

It was an amazing kiss, more intense for me because it was my first time kissing another woman. The kiss gradually became harder, more urgent; my tongue started to dominate hers as the passion of our groping intensified. She cupped my heavy tits, appreciating their impressive weight. She pulled one out of my bra as my hands reached under her skirt, squeezing those firm little buns that had first triggered my lust. I could feel the juices starting to flow inside me and the fingers of my right hand traced the edge of her panties, then slipped inside, traveling down and in. And then she abruptly pulled away, her arm sliding down mine to deny me access.

"Amy, there's something you need to know." But she suddenly seemed hesitant.

I couldn't stand it. "Chris, I'm so damn hot for you right now, whatever it is -- please just say it!"

"My parents named me Chris, but... not short for Christine."

For the second time tonight, I felt that disorienting confusion, like I was coming loose from my moorings. Why would she think I would care what her full name was? Christina? Christianne? Whatever! All I could think was, please just kiss me again!

"It was short for Christian." Her words hung in the air.

And the last of my moorings slipped away. I started spinning in a current, my bearings lost. I stared blankly at her. She was telling me she was... a trans woman. Her lips had tightened, her eyes were searching mine for a reaction. Her face was a mix of fear, anxiety and hope. The first thing I felt was tenderness. Tenderness for the person standing in front of me -- so vulnerable, so open, so honest. My confusion fell away. I suddenly felt my heart bursting for this woman, which is what she was, regardless of what might be between her legs. I gently took her sweet face in my hands and looked deep into her eyes.

"You're Chris to me, and I don't care if it's short for Christmas, I just want to unwrap my presents!"

Her laughter burst out like a damn breaking, and then mine followed. Within seconds our laughter was swallowed as our mouths came back together. Hands pulled at clothes, buttons flew, and we fell onto the bed. Her mouth clamped onto my exposed breast, her lips tugging at my big nipple as it hardened for her. I started to lower her panties, but I couldn't get them lower than mid-thigh without pulling my nipple off her lips. Raising my leg, I hooked them with my big toe and pushed them down and off one leg. She suckled greedily as my hand found her crotch and cupped her package. She hardened quickly as I began to stroke her shaft. She involuntarily broke her lock on my nipple as the sexiest whimper escaped her lips. Seizing the opportunity, I dove onto her little cock, taking the full length into my mouth. It reached the back of my mouth, just short of my gag reflex. Cupping her marbles in one hand, I greedily sucked and licked her hot little poker as she pivoted to bury her face in my pussy. I don't know how long it went on - it was so hard to maintain focus. My concentration kept bouncing back and forth between the delicious dick in my mouth and the incredible feeling in my pussy. I wanted to suck her dicklette and eat her cum. Until she started forcing so many moans out of me that my lips could no longer maintain a seal.

"Oh God, baby that feels sooo goood!" Too good to allow me to continue with my own efforts. I surrendered to her talented tongue and felt my eyes roll back in my head.

"Mmmm. You taste amazing!" She was plunging her tongue deep into my hole, scooping out everything she could find, slurping and swallowing as my pussy flowed more than it ever had.

"I..I... I need to cum. I need to cum so bad. Please suck my clit! Oh God, please suck it!"

Not hard enough! I grabbed her head and pushed it further down on my throbbing nub and she sucked me into oblivion. It began to feel like too much. I was hanging on an edge. I couldn't stand it; I needed it to end. Yet I couldn't bring myself to stop it. I finally nudged her away slightly to regain my senses. My sweet little licker took the cue and shifted gears, starting slow tracings around the center of my universe as I gradually unwound. I looked down to see the cutest slimy face, beaming a beautiful grin of pleasure mixed with pride. I motioned her up to kiss me, then gave her face the tenderest of cat baths. Reaching down, I started to stroke her still hard little poker.

"You know," I mused, "I have a toy at home that is remarkably similar to this little beauty."

"Really? You can buy any size you want, and you choose one so small?"

"Oh, I have larger ones too, but the one like this..." as I playfully flipped it back and forth, "that one fits just perfect in my ass."

I saw a fire spark in her eyes and she leaned in and whispered in my ear 'I want you on all fours".

A shiver ran down my spine and I quickly complied. Now my big boobs were hanging down and swaying right in front of her face. Her hand traced their way down the length of one jug, seeking out the fat nipple, tugging and flicking it until it was rock hard, then repeated the same with the other. She then rose up and knee-walked herself behind me, pushing my legs apart. Gently caressing my bottom with one hand, the other covered my gash, sliding up and down its length. Finding it dripping, she thrust her prick in, taking a few strokes, coating it in my juices. Then she pulled out and used her hands to collect a generous amount of my natural lube, applying it on and around my asshole. Slowly, gently, she began massaging my puckered hole, opening it up with first one finger, then a second.

"Shoulders down, ass up, baby". There was no doubt who was in control now.

I obeyed, spreading my legs farther apart to gain a bit more stability for what I knew was coming.

"Ooooh... my... God!"

I briefly worried -- did she just have a premature orgasm? I was about to console her when she spoke again

"I knew I loved your wide hips. I've envied them since I first saw you. But this glorious ass! The way it spreads out when you're like this... absolutely magnificent!

And then the head of her anal intruder was at my open hole. She pushed gently and I welcomed her in.

No, I thought, this wasn't anything like what I had imagined. It was so... much... better.

* * * * * * * *

"Very nice, Mary!" I smiled and offered golf claps. OK, firstly, 'I just want to unwrap my presents'? Brilliant! I loved it."

"Hah! I'm glad that one landed. So, got any questions?" Mary asked, knowing full well there would be. It had become the standard post read follow-up. Writing critiques and suggestions for possible improvements would come later. The more pressing interest was always to learn just how much the story revealed about the author.

"How much of that really happened? I know you actually have been with a woman before, but how about a trans woman?"

"No" Mary responded, "the opportunity never presented itself."

"Ok, and the anal. You've previously revealed using various toys, but what about a live one? Ever taken a cock in your ass Mary?"

"Yes".

I was trying to coax a blush but ended up getting a half smile and a wistful look. Duly noted. That might be worth revisiting later. "How about the psychology of it. The idea of someone who's accustomed to a 'normal' (air quotes) degree of agency in relationships, wanting to experience more total control. Have you ever felt like that?"

Mary paused on that one, searching her memories. "Hmmm, you know, I'm not really sure. I haven't actually entered into something with that kind of a conscious plan like Amy did."

I waited, sensing there might be more.

"There have been times when I have encouraged certain.. uh... escalations? You know, maybe a half-suggestion, perhaps a subtle nudge on the head of my pussy licker to encourage some southern adventures?"

Yeah, I know that nudge." I smiled.

"Sometimes it works out great, but sometimes there's a little hesitation, a little resistance. And of course, you just let it go and ride the wave you're on, ya know? And naturally there's gonna be a brief disappointment... missing out on the sensation you were hoping for, but I think the bigger disappointment for me is missing out on the feeling I get from the act of compliance."

"I get that," I said, "I do. Sounds like I'm not the only one who's gained a little more insight from that story."

"OK," Mary acknowledged, "Enough with the psychanalysis! I think it's time for nasty Jack's story, don't you?"

* * * Reunion (Jack's Story) * * * *

I picked up my notebook and began reading as Mary sipped her drink and settled in on the sofa.

"So, Allen, in our last session you were telling me about your upcoming ten-year high school reunion and how you're anxious about catching up with a particular female friend. I'd like to explore those feelings a bit more. I believe you said this was a strictly platonic relationship, is that accurate?"

"Yes, Dr Marx, it is. At least in so far as what actually went on between us. And if you ask Sharon, I'm sure she would agree, without qualification."

"How about from your perspective? I take it you are inclined to qualify that description?"

"Yes, although I'm not actually sure how I would. I thought back to all those nights I spent with Sharon, getting stoned together, riding around in her car with no destination, sharing stories of the day's events. Things that were said and done by classmates, things that happened in school that day. Had you been in the backseat listening, you would have agreed that 'platonic' pretty much nails it. But if you had seen me in my bedroom later, after she had dropped me off, you might have thought: how long can this go on before that boy beats himself senseless?

In my masturbatory fantasies I imagined myself as Sharon's boyfriend, holding her tight, pounding my slender little dick into her hairy pussy until she begged for mercy. The fantasy was particularly ludicrous given who I was -- a wimpy little nerd. Average height with a skinny body and a meek demeanor to match. In sharp contrast, Sharon's actual boyfriend was a year older than us and a total stud. A former varsity letterman and a current Golden Gloves boxing champ, making good money working at the local steel mill. And, I was convinced, hung like the real man he clearly was.

"I guess if I had to put it into words, I would call it 'unrequited love' on my part" inwardly cringing at the trite cliche.

"Aah, so you had feelings for this girl."

"Girl... heh. She may have been in high school Dr Marx, but Sharon was a woman by any objective measure. Physically and emotionally mature, with a self-confidence that allowed her to navigate any situation."

"OK, so you had feelings for this woman."

"Yes, I did", struggling to conceal the blush that revealed the level of understatement.

"Did you ever reveal those feelings to her?"

"Once", as I lose the struggle and feel the hot flush on my face.

"And... "

"And she shut me down! Well, in all fairness, I suppose it's more accurate to say she put me back in my place. Firmly." I had relived it so many times. My attempt had been both vague and feeble. "Basically, I had let her know that while I always enjoyed our time together, I wanted more out of it. Mercifully, she interrupted me before I could further embarrass myself and told me in no uncertain terms that what we had together was all it was ever going to be. She gave me a choice: keep things as is, or we stop spending any more private time together."

"What did you choose?

"Doc, I folded like a cheap suit. We never spoke about it again."

"And now you are anxious about meeting this woman again. Why?"