Carol gives me her ass.

Kara was out on a date, of sorts, and I was enjoying some tea and futzing around on Twitter. I like to be selective about whom I "follow," but it's true that I have a weakness for interesting, sex-positive women involved in one element or another of consensual adult fun. For me, that usually means fellow writers, sociosexual pioneers and advocates, or local porn stars. Take Montreal's own online 'amateur' Carol Cox, a fiery mid40s blonde, for example. Her ballsy don't-fuck-around-just-fuck-me-goddammit attitude makes me smirk.

To me, Carol Cox is among an interesting, seasoned sex-positive internet elite. I'm intrigued with people who saw the internet's sexual potential early on, and she began sharing her saucy self long before the days of Twitter or Facebook. I think that's very cool.

So recently, when she tweeted about finding a past picture of herself, I couldn't help but peek.

@CarolCox Just came across an old promo pic for my website...



I can't help but notice the sparklybits barely hiding the girlybits on the other model. I'm in a goofy mood, so I reply. Does Carol know me? Nah. I'm just being a fun smartass.

@UrbanRoguery When I die, will I head toward the light?

@CarolCox The dark is always much more fun. ;)

@UrbanRoguery Oh, now, if you're offering me *that* option... turn over. ;)

@CarolCox hahahaha, I wasn't even thing about that, but it's all yours for being quick ;)

Mmm. All mine. Which, of course, gets me fantasizing about fucking this delicious blonde sexythang in her tightest places. Ain't I bad?

@UrbanRoguery Ok. Now I'm thinking about @CarolCox 's beautiful derriere. Be still my heart. Thank you, Twitter.

@CarolCox Thinking about my derrière? Just for you ...

I think I made a new friend.

Sunday comics.

Tank girl.

For almost ten years, we were together. She was my first love, my first partner, and we met when I was a rascal in my late teens, fresh from high school, spanking new to the bdsm scene, plying my trade as a carnie at Renaissance festivals throughout the northeast coast. She was a mid-20s United States Marine and sometime-stripper who had just finished a tour of duty in Hawaii and had daydreams of flying fighter jets. She had come to the Renaissance festival with her biker friend and her daughter. With an equally rascally buddy, I was doing my job: drinking heavily and teasing the living hell out of "the mundanes."

I was dressed in skintight black Capezios, boots, and a hard, leather jerkin with a lovely blade dangling from my waist. She was ogling me from a short distance, her friend not far behind. I had a belly full of mead and spicy, flirtacious wit, so naturally when I spied her spying me, I approached her as any self-respecting rascal would.

The blade swayed from side to side, its hilt clinking against the vessel of whiskey that dangled from my belt, the outline of my package as easy to see as sinners on a Sunday, as I approached her. Slinking close, she smelled sunshine-warmed sandalwood oil in my light beard as I took in her body language, full of approval, bringing my cheek to her ear.

"Hello, m'lady," I whispered, booze on my breath and faerie dust on my perspiring brow. "Prithee... do you come to the faire to watch the men in their tights?"

She laughed a head-thrown-back, saucy, ribald laugh, the laugh of a tipsy girl from Southie who likes her man to have a nice ass, and nodded. She gave me a "kissing stone," a small rock painted with a tiny, inviting red heart. Within the next hour, she was getting friction burns on her knees as she rode my cock on the upstairs floor of my rustic merchant's booth, amid my camping equipment and collection of medieval costumes.

Not long after we were done, her biker friend had her turn, suffering my carnie friend's pair of leather wrist restraints as he bound her to a rafter and had his way with her in the same room. They never stayed in touch afterward, but what started for my new friend as a sexy, drunken Renfaire fling would become my first longterm, primary relationship.

Had I more courage at the time, I would have married her. I should have. I almost did.

Before Kara, and even before The Grrl who influenced the development of this blog, there was Diva. I keep referring to her in passing, so on the event of her birthday, it seems fitting to share a glimpse.

I so loved Diva.

She's a dirty blonde vixen who has always managed to fuse the allure of whitecollar elegance with bluecollar spirit. One moment, I'd be enjoying watching her sip champagne from Baccarat crystal over braised quail, and the next minute, she'd be belching in the car like a Plymouth longshoreman after a trip to the package store. An occasional stripper (for which she very nearly faced a "conduct unbecoming" charge while on active duty), she wasn't exactly an innocent when we met. Still, in our time together she found herself introduced to a panoply of adverturous play and shared ecstacies that, I smirkingly know, lasted within her well after our relationship ended.

I introduced her to kink. When I wasn't haggling to buy men's wives or children during my hysterically drunken Renfaire taunts ("Oi, m'lord, two pigs fer yer wife thar... my, but she's a purdy one, neh? Lesse her teeth now... oh yeh, yeh, two pigs an' a chicken then, wot say? Tis a good chicken..."), I was working at either an adult toy store in Greenwich Village or bouncing at the clubs, and it wasn't long into our relationship that she discovered exactly how much she loved receiving a good spanking on her beautiful ass.

Diva would squeal so satisfyingly when she was across my lap, and over time, she developed such a tolerance for OTK play that by session's end, her derriere would be fire-engine red and burning throughout the night. She became so enamored of having her hiney whupped that, after we broke up, I was amused to find sex-networking listings from her on various internet sites where she openly sought "the attitude adjustments I so deserve."

She drove from Boston to New York once to surprise me when I was on-duty at a club. She strolled in as I was supervising a scene between two lesbians, and by the end of that night, I had her dangling from the chainlinks suspended from the cieling as I tortured her with horsehair whips and riding crops.

Once, while visiting her, her brother accidentally walked in on us as she lay sprawled on the living room floor as I hovered above her, slowly dripping hot wax onto her pretty B-cup breasts. Oops.

At another club, after spanking, paddling, and restraining her on a St. Andrew's cross as I pinched her nipples with clamps, I took her into a blacklit booth where I pressed her hands against the wall and fucked her from behind. As I drove deeply into her, tugging her adorable ass against me hard and fast, masturbating voyeurs moaned and stroked both their cocks and pussies as they jockeyed in position for the finest view. When we were finished, Diva told me later about the streams of anonymous semen that found itself splashing along her leg while I pumped her senseless.



We had friends among T-Bears MC, a kink-positive women's motorcycle club, and with them we became part of the clique that founded the Boston chapter of the National Leather Association. It was Diva who, during a relaxed party at our pad, came up with the name for its newsletter, Scarlet Leather, which it retained long after the group redeveloped into the New England Leather Alliance.

We were social butterflies (or wasps, if you prefer) then, movers 'n shakers, the Kind Of People You Wanted To Know. I did workshops at NLA meetings about riding crop use as sex toys; Diva dropped trou to help me demonstrate. I drove our black Ford conversion van as we trekked to another private playparty; Diva knelt on the van floor as our brunette BBW friend, Jacqueline, opened her legs to receive Diva's expert tongue.

And her tongue was deliciously expert. Diva was superb at sucking cock, and knew all about that balance between a firm, wet grip of the fist while also offering a tight, sucking, pouty pair of lips. We would embrace for vast stretches of time, orally spooning as we lay on the bed on our sides, her head at my waist and my hands at her head as I vigourously pumped my cock into her willing, wanton mouth.

She would crawl on all fours, clad only in a teddy, onto the center of the Oriental rug in the playparty host's parlour. There, in the center of a circle of chairs occupied by voyeurs, men and women alike, she would bend her head to the floor and raise her lovely ass high to receive whatever spanking, paddling, cropping, waxing, icing, clamping torment my naughty imagination could muster. How she loved being tormented upon her ass.

Diva's ass. Diva loved to have my cock, deep and thrusting as she perspired under me, inside her ass. How she would hiss and growl as she felt herself get taken, how she would gasp and loudly whisper "Hot! So hot! So... hot!" as my fiercely pumping thrusts burst my cum deep into her body.

Three times I shared her with other individual men, where she was
DP'd each time until she gasped and rolled her eyes back and dropped limp with ecstatic oblivion. One man was a celebrity, of sorts, whom we knew. Another was a bodypainting artist we met at the Renfaire. The last was a mutual friend who was about to wed a woman who detested anal sex, and we gave him something to remember.

At least one orgy, four couples. More playparties. The couple who rented a 1-bedroom apartment just for their swinging trysts. The couple who wanted to simply see a demonstration of my Topping skills as the sound of Gregorian chant echoed throughout their basement dungeon. The teen couple, both redheads, also from the faire. Picking her up after a shift at the stripclub. The afternoon I fucked her on a hillside in the snow as friends nearby sought for us. The night beside the lake as I took her from behind, knees on grass, as a crowd of nude, ribald men and women danced naked around the bonfire to the thrumming of drums and song, our visage barely visible by the glow of embers under a starry sky.

I have written a great deal about my lovers in this blog, but after some thought, nothing I have written to date can come close to the quantity, the quality, of adventurous sexplay that she and I had explored during our tenure together. I've had lusty, imaginative daydreams about exploring nearly as much, being nearly as active in the kink community again, with a partner as I had enjoyed when Diva and me were the Thing we were.

But, yes, it ended. Maybe it was the 7-Year Itch, or maybe the planets simply went kerblewie out of alignment, or maybe it was just time, but we eventually drifted apart. I moved out on Christmas Day. The ripple effect among our circle of friends was vast. I pierced my right lobe (the left ear had been done when I was sixteen) to mark the monumental change in my world.

I would never have admitted it then, but losing Diva was one of the best things to ever have happened to me. For all my sexual exploration and streetwise education, I was a kid then who didn't really know shit about women, relationships, communication, the vulnerability that comes with love. Diva, in her own way, taught me those things, as she taught me certain life-affirming maxims that are tattooed to my forearms. She showed me how to appreciate women who have cajones.

After our breakup, she raced motorcycles for a time and travelled to Europe. Her landscaping business flailed in the recent recession, and she's since moving on to become a corrections officer. It's a career choice that I think she'll do fine in.

Oddly, she's single. Her last boyfriend strung her along for the longest time, never getting the message that all she really wants is a steady, committed partner with whom she can build and share. Maybe her attitude gets in her way, because she's as openmouthed as she is openminded.

We didn't talk for the longest time, but we're friends now, and call on rare occasion. Her mid20s daughter, whom I raised with her during our relationship, calls me Daddy to this day and had her second child by her good husband, a Coast Guard seaman, within the last few years.

I loved Diva very much, and I still do, in a fashion. She's clan. From time to time, like on her birthday today, I think about her and send her good vibes.

Happy birthday, beautiful.

I still have the kissing stone.

Kara.

The truth is that I hardly know where to begin. If I've seemed silent lately, believe me when I tell you that it isn't because I've been idle.

Clarity is a healthy and good thing, and while there will remain a great deal about what was shared (such as it seemed) between my last primary partner (such as it seemed) and myself that I still enjoy the memories of, I also know that sometimes it takes a complete redirection in the world before beginning to comprehend what was amiss prior to change. In these last few weeks, and in the last week or so in particular, I feel as though I'm getting fast-tracked into some bold, healthy, sexily glorious new awarenesses and opportunity. Aphrodite is being both kind and revolutionary. I have clarity, fun, and sextastic possibilities before me. Life is good. Really, amazingly, comfortably, finally good.

Kara, the Math Teacher, is a gentle, savvy, sassy, articulate, sharp, lithe, faerie whisper of a tomboi woman with short dark hair and eyes like small jade discs. I have to remind myself that she's in her early40s, because in both looks and spirit she is a woman of half her age and could easily pass for one of her probability students. Gracefully feline, I behold art incarnate when I hear her chant in the morning, or see her in natarjasana positions.

Her petite, dryad's form belongs on canvas adored by Waterhouse. With her shorn, straight hair, the nape of her lovely neck is always edibly available for me to feast upon (which she adores), and her skin, soft as oak moss in the wood, faintly tastes of almonds and spiced vanilla. Her deliciously charming, small faerie breasts are capped like candies with alert nipples standing proudly atop tiny, sensitive, pink areolae. Despite having brought a pair of excellent, delightfully golden children into the world, yoga and biking have left her with a taut, sexy tummy. Her beautiful, sensual ass is small, heart-shaped, and as pert as a split peach. A fabulously soft triangle of short, dark curls beautifully adorns her feral pubis. When aroused, her outer cushions swell and darken like ribald, wild fruit begging to be tasted slowly, its nectars a thing to be savoured.

It pains me that, as I am told, few past lovers have given her the bodily adoration a lovely waif such as she deserves.

This I have every intention to amend.

In my life, I've languished in the company of many bodytypes of women, and I've treasured them all. But if I were ever asked of what visage would make me happiest, as a man, as a lover, would I have no other choice for a playmate for the rest of my scandalous days, what I might share would likely surprise some people: mildly dykey, just slightly geeky, educated, shorthaired, petite brunettes. And I've found her in Kara.

She is the stuff of my fantasies.

But even more important than her appearance, and this to my own surprise, is the immediate ease in which she and I seem to be drawing closer to one another. There is no angst, no sense of struggle, no discomforts of note, no worries. There is no superficial narcissism or disconnects. There is no expectation for unyielding openness while retaining battened hatches. There are no hidden agendae. There are no yo-yos. We get along as easily as if we'd known one another since grade school, and every thought shared between us reminds us of the real, resonant, giving desires we each have come to learn about ourselves because we are each smart enough to have learned about ourselves.

Not that we don't have some differences. My sense of kink is almost entirely new for her, and that to the strong contrast to where my previous partner has since gone. But, much to Kara's delightful surprise, we're embracing this difference as a delicious opportunity rather than a liability between our sexual selves. My experience in kink offers her a pirate's treasure of sensual new possibilities that no previous man (or woman) has been able to previously share, leaving only in question of how deeply, how greedily she would wish to dig in the island sand... and her combination of curiousity and innocence delights my thickening cock with every fantasy I've ever had about corrupting young beauties down a wayward path to sensual perdition.

And for the first time in years, I'm not feeling a "need" to date elsewhere, at least for the forseeable future. Whether or not this new partnership will become monogamous remains to be seen (we both agree in the view that monogamy is fundamentally alien to the human animal), but for the first time in a long time, I'm much more interested in nurturing and exploring the possibilities ahead of me, building this foundation, rather than take time and energy away from that prospect. I suspect, if and when extracurricular play might happen, that it would more likely occur with us as the team we're becoming. That's a paradigm I've known and enjoyed before, and would be thrilled to see it in my world again. After all, adventurous sexplay is just so much better when it's shared with one's best and intimate friend, I think.

Kara's presence in my world is a fun, vibrant, feral, welcome change. I'm looking forward to seeing where the faeries take me.

Service while u wait.

She was getting ready for a weekend away with friends, and her car was in the shop. That afternoon, she was supposed to be grading papers, but instead she made a booty call. Such a hussy.

The Schoolteacher is one my newest friends, and while we really have precious little in common (she the condo-dwelling Catholic school soccer mom, me the artsy-neighborhood heretical leatherman), she really likes me and enjoys nurturing her latent bad-assness when I'm around.

And it's so hard for me to turn down a good opportunity to corrupt a woman of God.

I smiled to myself as I drove out to meet her at her mechanic's garage. The last time we were together, we talked about kink and basic bondage play, which she readily admitted having had fantasies about for years. It quickly became clear that I hadchainlengths worth of more experience there than she, and the possibilities seemed astronomical. So, naturally, I packed a little toybag before I left the house.

I arrived at the garage. She greeted me with a kiss. The car would only take a few short hours, Mechanic Guy said. Come back in a few.

The Schoolteacher, an extraordinarily buxom longhaired blonde, sashayed her denim-covered hips with a laugh as she looked at the clock on the dirty garage wall. I rolled my eyes with a smirk as we made our way to my car.

At her condo, there was only the briefest smalltalk before she reached for me as we lounged on the leather couch. Her kisses were deep and hungry, and once again I felt the incredible presence of her truly huge breasts upon my chest. After a while, she got up to pour me some wine, but took none for herself.

She had given it up for Lent.

But cock, I soon discovered, was perfectly fine.

I carried my wine in one hand, her wrist in the other, as I led her into the bedroom. We made out as we stood before the foot of her pillow-strewn bed, my hands caressing her back and tugging her long locks. I unbuttoned her top to reveal an elegant burgundy bra straining with round fullness. She lay herself down. I removed my shirt. She groaned at the sight of my broad chest and reached upward to caress my nipples and shoulders. Smiling, I placed a knee between her knees as I climbed atop of her, and as I planted a firm and searching kiss onto her open mouth, slowly pressed and circled that knee against her mound. Even through both of our jeans, I could feel the heat that seethed between her legs as I bit her lower lip and flicked a tongue along her jawline. She gasped and writhed deliciously underneath me.

"I love how you make me feel," she said to me in a whisper.

"You'll love this," I replied as I began undoing her jeans, tugging them down over her feet, and parting her legs.

Her panties were moist already, and when I swabbed the fullness of her sex with the wet flat of my tongue after tugging them aside, her hiss filled my ears. Her hips rode up and I kept pace with her squirms, never letting my tongue leave her folds or the thrumming button inside them until she eventually came in a long shuddering sigh.

I spun her over to reveal her ass to me. I yanked the panties down her legs. I gave her butt a few friendly swats before tugging my belt open and removing my jeans. I lay down beside her.

She tasted her sex on my mouth as she kissed me again, and gradually moved her way down my chest. Soon, I was right back where I was during my last visit to her bed: on my back, my head enveloped by huge pillows, the Schoolteacher'sblonde head bobbing slowly in my lap as she languidly sucked my dick.

But our time was short, and I had an agenda to fulfill. Inspired by an image I had posted here recently, and by her expressed desire for light bondage, I slowly pulled myself away from her teasingly. My wet cock wagged in her face for a moment as I did so, eliciting the nicest little whimper of disappointment from her throat.

She looked at me as she lay curled on the bed. I reached for my wineglass and savoured a long pull from it. Standing at the foot of the bed again, I placed mytoybag next to her feet and opened it, looking into her eyes and smiling.

"What are you doing?" she asked.

"Do you know what a safeword is?" I asked this beginner in return. Her eyes widened just a little as she nodded.

I already had her little wrist restraints handy, those same restraints she previously confessed to me as enjoying to wear "just for the feel of them." From my bag, I withdrew some steel clamps and my pair of ankle restraints.

I love these restraints. I don't remember how I acquired them or who gave them to me, but I remember being told that they are genuine patient restraints from a mental health facility. That salacious history and their supreme construction, thickness, hardiness, and comfort allow me to forgive the fact that they are brown leather.

"On your hands and knees," I instructed. She obeyed.

"Face down, all the way down," I instructed. She complied.

This left her ass high and round in the air, especially when I adjusted her so that her upper body weight was supported by her shoulders against the bed. I reached for her wrists, securing them in her restraints, and brought them under her massive tits and against her feet. I secured my asylum restraints to her ankles, smiling as their brass rings slid through their leather slots unforgivingly. Using a pair of double-ended steel hooks, I clikked ankle to wrist to wrist to ankle into a continuous line of leather and steel.

Her feet dangled over the edge of the bed. The side of her face and her shoulders were firmly planted onto the sheets. Her ass was fully available, raised saucily high, completely vulnerable for my use.

I admired her soccer mom's posterior as she got used to her position. I sipped the wine that she so obediently denied herself. I began spanking her broad, round, naughty ass as she cried out loud and pleaded. Ignoring her protestations, I didn't relent until each cheek was appropriately red and blushing, framed with the strokes of my nails along her thighs and back, dappled with the tiniest scarlet dots and faint handprints. Her face was flushed with embarrassment, but her quivering pussy was flushed with excitement. Her folds were almost purple and dripping when my hand began swatting her there also. I cleaned off my dampened fingers with swipes across her brutalized ass.

She squirmed in her restraints, undoubtedly experiencing some of her first stirrings of deeper submissiveness. Though by my standards I was being terribly gentle, this was still probably a little more than she bargained for... so I chose to give her what she was expecting, although in my own tawdry way.

I gave her a few more sound swats as I wrapped my cock. Stopping to caress her back, I held a hip as I pulled her closer to me, slowly sliding mycockhead into her drenched tunnel until every bit of me was deep inside her. Her gasps were different now, and when I held both hips firmly and started to use her pussy for my own pleasure, her cries stopped including pleas for mercy.

The steel clamps clackled against the D-rings as I fucked her, the bed squeaking as my thrusts urged the mattress forward. I took her deeply, firmly, feeling her tighten around me as I stood behind her and thrust. I pulled her ass against me as I pumped inside her, and my balls slapped noisily on her skin until she screamed and came, shuddering.

I slowed down and withdrew. I sipped my wine. I checked the circulation in her wrists. She was doing fine, fine, more than fine.

But I wasn't done. Still enjoying the sight of her ass so beautifully high in the air, and knowing that I was sparing her more interesting torments that I otherwise would have ushered her through, I decided that I deserved one particular treat.

I returned to my toybag and began lubing my fingers as I riveted my gaze to her oh so vulnerable, oh so available, oh so tender anus. Her hole was faded pink and surrounded with a sunburst of short, little seams. I teased her ring with my wet fingers as she closed her eyes and opened her mouth silently, her face still pressed down, down, down to the bed. Her hole clenched against my fingertip as I wiggled my wet index finger inside her, circling her, only slightly widening her up. Squeezing the bottle, I ran a line of lube down the length of my cock and then slowly stroked myself until I was covered with joyful goo. I tapped my cockhead against her rosebud, held her hip with my free hand again, and gradually pressed forward and watched the head of my cock slither and pop into her nethers. Eventually, I was gripping handfulls of her asscheeks as I tugged her against me, impaling her onto me, taking her.

The Schoolteacher squirmed. The Schoolteacher moaned. The Schoolteacher stayed on her shoulders and knees, locked in restraints by the wrists and ankles against each other, while I fucked her submitting, Lent-observing, should-really-be-grading-papers ass until her entire body was shaking and perspiring and cumming and red and squirming and utterly, completely fucked.

Her cellphone rang. Her car was ready. She blinked her eyes a lot after I released her and held her shaking body under the blankets before we each grabbed a shower. She was still weak in her knees, she said, by the time I was dropping her back to her mechanic's garage.

I smiled as I drove home, tapping my little toybag with my hand.

An apple for teacher.

Irony. As I carefully drove through the falling snow, I laughed to myself about the total irony of it all.

All of my life, I've usually found myself attracted to almost the opposite "type" of woman that advertising media, pop culture, and standard-issue porn insisted I get attracted to. When my high school buddies drooled over Loni Anderson, I was (and remain) weak in the knees for Annie Lennox. The buxom blonde bombshell looked great on the fuselage of a fighter plane or in a classic pin-up calendar, lovely to admire in a centrefold, but for all my appreciation for bodily diversity, my libido usually fell prey to Rosie the Riveter. Punk grrls. Tombois.

And yet here I was, en route to the Schoolteacher's condo. Schoolteacher Karen, with the long blonde hair and huge tits. Part of me feels as though I've crested the definitive peak of male vanilla heterosexuality. My father, tit-man that he was, would undoubtedly be proud. For me, it's a little weird. But I'm still smirking.

After several days of hysterical emails and fun phonesex play during our first conversation together, she won me over. I liked her confidence, her intelligence, and the fact that she seemed to have her life together. Nice. She's making up for lost time following an unsatisfying marriage and dating "nice" guys with passive-aggressive issues. I can handle that.

And how could I resist the opportunity to further corrupt a successful, middle class, parochial school teacher? Oh, the fantasy potential. Schoolgirl uniforms would be redundant.

Her elegant and charmingly spartan pad was already aglow with candles, and lasagna warmed in the kitchen as we opened the shiraz that I brought with me. I hadn't been there for more than fifteen minutes before, as we languished on her leather couch and discussed our lives, that she leaned close to me for a sensual kiss. One became several. The generous cushions on her chest pressed firmly to me as she leaned forward, her mouth slowly exploring mine.

We talked about mutual interests, the swinger's events that former dates of hers had brought her to, my past in phonesex and the leather clubs. We chuckled over the divergence between our respective spiritualities. We discussed sextoys, and it felt completely casual and relaxed when we briefly peeked online to peruse options we could potentially share. She liked the idea that I review them, and apparently her girlfriends had already been teasing her about that fact of me.

I smirked to myself when, following dinner, she simply took my hand and led me into her bedroom. She matter-of-factly showed me her small collection of toys, all cleverly locked in a fishing tackle box. From under her collecton of rabbit vibes, lubes, and the massive Ziploc baggie of condoms, she withdrew a pair of Velcro restraints.

And I thought she needed corrupting. Silly me.

"Put them on me," she asked quietly as we stood next to her bed. "I... just like the feel of them on." I smiled as I undid the Velcro and wrapped the straps snugly to each of her wrists.

But as we made out on her bed, her quaint Catholic girl sensibilities tried in vain to limit her enjoyment. Had a pesky angel truly reared itself on her shoulder and cool the evening down, naturally I would have relaxed; I hadn't any preconceived notions about the evening at all, apart from lasagna and shiraz. Yet watching Schoolteacher push away those prudish anti-sexual spirits elated me. She wasn't listening. She was giving in to her desire. How lovely.

Whilst my nibbles teased the nape of her sensitive neck, my hands explored her almost-intimidating breasts, my fingers sending shockwaves to her clit as I gently rolled her nipples between them from over her sensuous and expensive bra. She lay on her back, wrists dangling above her head and over the edge of the bed, as I gripped both D-rings of the restraints in my right forefinger. Laying beside her, I teased her large breasts while tugging her wrists firmly, and Schoolteacher squirmed her hips in slow gyrations from the slow torture. She moaned how she enjoyed the firmness of my left hand as it caressed her arm, her tummy, her thighs, and her gyrations quickened when my palm cupped her mound from over her bluejeans. Her kisses became insistent. My hand seethed in moist warmth. Feeling the heat from under the denim reminded me of heavy petting during after-school parties. Ironic.

That angel on her shoulder must have huffed and puffed impotently when her bra was removed, those incredible goddessly tits bared before me and my tickling tongue. I'm certain that by the time the jeans were being tugged down her thighs, that angel had departed to seek out some other sinful Catholic girl to aggravate, leaving the one under me to her imminent perdition.

Begone, spirit, begone. Lovers would have their way here.

Schoolteacher lay before me, clad only in white cotton panties and her long, blonde streams. Her bare and bountilful breasts swayed gently as breathed heavily, looking up to me while I stripped off my shirt. I slinked atop of her, gently cupping a breast in each hand, and she groaned aloud as my lips caressed her body. Brief nips at her areolae sent her into spasms, and her hands tussled under the pillows at her head. Kneeling up, I smiled.

"How'd you like me to go down on you?" I asked casually.

Not a pesky angel, but a troublesome imp appeared at her shoulder next, for she paused. In a brief time-out, we cuddled as we talked about some past experiences with less-than-ideal lovers that had left her unsure in that regard. I caressed her leg as she shared some apprehensions, and alleviated her tension that, yes definitely, I do enjoy sucking pussy. Inwardly, I rolled my eyes at the insensitivity of some men.

Schoolteacher decided to trust me. Schoolteacher rolled over when I asked her to. Schoolteacher showed me her generous ass when I lowered her panties.

Raining her bottom with kisses and nips, my hands explored her back and tugged strands of her long, blonde hair. I hoisted her to her knees, and chuckled when she looked at me from over her shoulder.

"Like this?" she asked, perplexed.

My reply was to hold her bum with my hands as lay on my stomach and tilt my mouth to her, swabbing her shaven mound with the full of my wet tongue. Immediately, she bucked forward slightly with a heavy groan, and began faintly shaking as my mouth explored her while she relaxed. With genuine assurances that I was having oodles of fun with her clean and soft folds at my mouth, I could feel her apprehension ease as she gave herself permission to admit her pleasure in my pleasure. Her groans became more intense, her moans deeper. Had this women ever received good head before? I settled my weight on the bed and decided to completely take my time, wanting her to enjoy herself. I teased her slowly, gently, the tip of my tongue flicking at her hardening clit and sending her into shudders. When I moved upward and began swirling the tip around her winking anus, she quaked uncontrollably.

"No one's ever done that to me before!" she ecstatically cried out, her face in the pillow and her ass in the air, between her deep gasps. As I alternated between her backdoor and her pussy, sliding first one and then two fingers inside her quivering body as I teased her clit, she moaned and screamed and whimpered deliciously. Rolling on to her back, she stared into my eyes as I feasted on her until, finally, her legs scissored around me as she crested into a massive, shuddering cum. She kept repeating my name as she came down from her crest. I smiled as I caught my breath.

Catholic girl sensibilities were tossed to the wind by the time my jeans found themselves on the floor. She stroked my shaft slowly as I lay back, her passionate kisses feeding me. Coiling an arm down the length of my body, she kissed her way down my chest to my throbbing cock and hoisted herself on her hip to bring her head above me. I caressed her long hair as it cascaded on my abs while she took me in her mouth, her tongue teasing the crown of my cockhead in slow, wet swirls. There's something very relaxing about getting sucked in this position, a lover beside you and bent to face your legs, watching her head bob slowly from behind. There's more mystery to what she'd doing because I can't see her face, and more surprise when she does the unexpected. Schoolteacher did something nicely unexpected when I felt her mouth suck me deep, the base of me almost to her lips, my cockhead sliding against the roof of her full mouth. Nice.

She adjusted herself, kneeling between my legs to blow me more vigourously, and she looked into my face as she did so. I became thicker and harder as she nursed on my cock, teasing my smooth balls with her tongue as she jacked me. Schoolteacher likes cock, and I gave her as much as she wanted, for as long as she wanted.

"I want you to fuck me," she whimpered past her puffy, wet lips, just slightly and naughtily swollen from pumping up and down my shaft. I thrust my dick into her mouth for a few more strokes, and she slurped me noisily, her face moist with spit. I wanted the scent of me on her face when I took her.

I tugged her up for a slow kiss before leaving the bed. As I wrapped my twitching cock, she assumed the position with her feet on the floor and lay her head down on the bed. Her ass swayed before me saucily, and I rested one foot on the edge of the bed as I gripped her hips and aimed myself for her tightness. She gripped me snugly as her hands pressed into the bed's comforter, and I slid myself slowly inside her until my balls barely met her clit. Pushing that much further in, I stopped when all my length was comfortably burrowed in her pussy, and then I gradually withdrew and started a slow fuck. She groaned and closed her eyes, her face down onto the bed as she gasped quietly. I built up speed and insistence, holding firmly to her hips until I was tugging her back toward me and my balls began slapping noisily against her wet flesh. I was fucking a schoolteacher, and the schoolteacher liked it.

"I love the feel of your cock in me," she panted, begging me to fuck her harder. I moved my hands to her haunches and held her ass against my palms as I thrust deeply. She shook against the bed as I took her, and I watched the falling snow through her bedroom window while her pussy cloyed and gripped around my pumping dick. She started to moan as her orgasm built inside her. She cried out my name.

"Fuck me! Please fuck me!"

Pushing her down to the bed, I held her ass as I mounted her from behind, biting the nape of her neck. When she came, she spasmed deliciously.

We took a breather, enjoying the wine. She laughed at how furiously she had cum as I went down on her, and it was clear that any apprehensions she had were gone. I enjoyed that. She made serious I'm-having-fun eyes to me, and I enjoyed that more.

As we cuddled, I playfully spanked her ass and she shrieked satisfyingly. Teasing her rosebud with a lubed fingertip, she went into her own world of bliss as I happily discovered how she enjoyed attention there. Gradually, one, and then two of lubed fingers began exploring her backdoor, and she met my strokes with an upraised ass and a quiet sigh or two.

Now how could I resist this? Palming some lubricant, I stroked my reawakened cock until I was slick and glossy. I shifted on the bed to mount her from behind again, slowly sliding my cockhead between her pert asscheeks until the tip of me found the crinkled doorway I was seeking.

"Are you ok?" I asked. She nodded. And slowly, I slid the tip of me into her until pausing after the fateful breach with my glans. Caressing her hair, I took a deep breath and steadied myself as I slowly, purposefully fucked the Schoolteacher in her pretty ass. Her face contorted beautifully as she felt me take her, my thickness filling her up as she panted under me. I raised myself up, fists near her forearms, my ass pumping downwards and upwards as I thrust my cock deeply. She was tight and took me readily.

It was a long night.

The following morning, she almost made herself late for school (!) because she wanted a little more cock for breakfast. I snuzzled into the warm sheets as I gently thrust my morning wood into her slurping mouth before she darted into the shower. Later, as we approached her car, she fumbled for her keys while her hands were full of assorted stuff. Frustrated, she passed to a handful of things into my hands as she reached into her pockets.

I found myself holding a handsome granny smith apple, and I burst out laughing.

Teacher likes bad boys.

When there are decent dating sites out there, sometimes I wonder why I still bother with Craigslist. Maybe its because the anarchic nature of it appeals to my sexual politics. Maybe its because, while there are definitely some lunatics on there and one's screening process really needs to be acute, there are also Morgans and Stacys who can make the winnowing worthwhile.

Moving forward from my more recent misdventures in dating (have you seen that new reference in the updated header?), I cast a net for the helluvit recently, wondering if an option other than one-night stands might actually be out there. I really didn't expect any replies. I received eight. Of them, it's been with Karen that I've enjoyed some hysterically fun and funny emails over the last few days.

An early50s blue-eyed, longhaired blonde, happily divorced schoolteacher, Karen may be a wee bit older than I, but we seem to have empowered singledom in common and she's intelligent, outspoken, and wellness-positive. Despite the charming pictures she's sent me however, I know precious little about her physically other than her hair and... that she's "proudly endowed" with 34G breasts. Good God.

Being a man who's usually attracted to more modestly adorned ladies, the light dinner we're planning for this evening should be interesting. But, hey, if the attraction turns out to be mutual, I'm all for diversity, because her smarts and attitude already have me smirking. Which, frankly, considering the kind of women I've been meeting lately, would be a plus.

That, and the confessed fact that she loves to suck cock.

I had told her about my past as a phonesex worker, and she responded to say that during a recent "wild women's weekend" with her "accountant friends" (oh, how that got my sarcasm going...) she and her buds had been discussing setting up that very thing. Must be the economy. So, upon hearing about my former semi-sexworker status there, her interest was piqued.

"I am one of those girls attracted to the bad boys!!" she had emailed me. "And the phone sex... now THAT makes me curious, hungry, and... well.. HOT. Sex is all about having fun, and driving your partner WILD, and it's a neverending adventure. Well, I really do want to hear a PROFESSIONAL in action... so, how much do you charge, mister? Could I afford the very best?"

We spoke for the first time last night, and the truth is that I really wasn't planning on pursuing anything randy. We talked about her kids, our exes, Jonathan Kozol's work about race and funding in American schools, what we like about being single and what we'd like to see in possible future partners. We laughed about "wild women accountants." We flirted casually. And then I asked a fateful question. Honestly, I was just curious.

"So, what are you wearing?"

A deep chuckle came from her throat. "Um... I'm naked. On the bed."

Relaxing on my futon, I smiled silently and nodded. "Oh, really? Did something inspire you?"

"Uh huh. And I have a little toybox here. Do you wanna play?"

I blinked. Ooo. Ok...

I had been working out earlier, and was clad only in a pair of my alma mater sweatpants. I smirked, lay back on the futon, and felt the slight twitch through my awakening dick under the white cotton. I hadn't enjoyed a phonesex session since a chat late last summer with Carly, I've missed it with Shayne, and it felt overdue.

"Tell me about your toy," I asked, smirking.

"Is it ok with you? It's not too kinky for you if I use one, is it?" she asked, sounding defensively concerned.

If she only knew. I tried to stifle a laugh. "Um... no, it's not weird for me... at all." Already, I was asking myself when I was due for my next shipment from VibeReview, what she might like if we actually did hit it off well (am I generous, or what?), and whether or not I would share this blog with her. "Uh, relax, no, you go right ahead." She sounded relieved, as if I taken an old burden off of her shoulders. I liked that.

I reached into my sweats and gently tugged my growing cock as I listened to Karen, this delighfully randy blonde-blue-eyed schoolteacher, play with herself. Really, what a privilege it is to enjoy listening, watching, a woman explore herself. I smiled as I listened to her sighs and how her breathing became softly ragged.

"I'd like to tell you that I'm really wet," she breathed. I thought about our emails over the last few days. Nothing explicit, but funny and flirty.

"Mmm. Have you been fantasizing about me, schoolteacher?"

"... Yes."

"I see," I smiled, holding the cordless close to my ear. "So tell me then, what have you been thinking about? ... My cock?"

There was a pregnant pause before the deep inward breath. "...Yes... ... I want... ... ... Can I have it in my mouth?"

Well, my. I lowered the sweatpants to around my ankles as I lay back and relaxed, stroking myself now for true.

"You'd like that, wouldn't you, schoolteacher? My cock gets really warm and nicely thick..."

A moan.

"... and you'd like to feel it sliding between your pretty lips, wouldn't you? To feel it throb and pulse on your tongue, feel it twitch, to taste it, know the scent of me is starting to seethe along your wet mouth. Yeah, I think you'd like that."

I could her her breathing quicken. Her staccato rasps told me of the movement of her body as her jilling became faster, hungrier. She was fucking herself with a dildo, likely on her back, her legs spread wide and her long hair scattered across the pillows. I pictured her knees up, her thighs splayed, the blonde racing stripe she had told me of gradually dampening with her desire. It was fun.

"I love sucking cock... I do..."

"I'd want to feel your tongue swirl around the head, feel your wet and sucking mouth..."

A deeper moan. "... I'll suck it deep..."

"I know you will. And I'll gently hold your pretty head in place and fuck that sweet mouth of yours. Suck that cock..."

The groans became more intense. My cock swelled in my first, the spongy head thoroughly enjoying the sensation of my closed fingers as I pumped my fist. We stopped speaking for a while, simply listening to one another. I closed my eyes and enjoyed the wicked sensuality of going in this direction with a friendly, but really total, stranger. My own thoughts started drifting into wayside tangents, memories of lovers, memories of phonesex, as I listened to the schoolteacher thrust her dildo deeply into her drenched academic pussy and daydream about blowing my bad boy phallus. I enjoyed her whimpers. She listened to me stroke.

"Would you cum on my face?" she panted, slightly out of breath. "I like... I like..."

And then I heard her cry out, gasp, and shake. When she did, I felt my balls tighten and the happy tubes of my body fill with me as I burst across my abdomen in two or three streams. I growled, panted, and gasped too. She continued to moan quietly as she came down from her crest. Soon after, we were chuckling.

"Goddammit," I said to her in a playful, feigned anger. My fist and abs were soaked with me. "You made a mess. Look at this."

"I love safe sex," she whispered appreciatively, "and it doesn't get any safer than this."

Dating weirdness.

I've heard it said that "even bad sex is still pretty good."

I have my doubts.

Things have been very bizarre since the holidaze. Still adjusting to the changes between Shayne and me, still supportive but nevertheless aware of the paradigm shift with Morgan, January has left me scratching my head a lot. Crazy Stacy and I haven't reconnected (yet?), and even if we did, I have no delusions that it would develop into anything regular or dependable. Kinky Hannah is away in Europe, and I'm unsure yet if we'd have a second date or not. Glamorous Lauren and I have always been Just Friends. I've decided that I'm a little uncomfortable about the recent surprise experience with Bubbly Lee.

Whenever writing about my lovers, I always endeavor to be as positive and nurturing as possible while still remaining truthful to the events at hand. I prefer to treat women with respect and appreciation in virtually every circumstance... but sometimes I find I have to face some simple man-truths, cock-truths, heart-truths.

Fairly recent experiences with Biting Tina and Lee have shown me that sometimes I'm prone to entertaining sexual options that I already know aren't going to completely satisfy me. Maybe its because of that maxim, that "even bad sex is still pretty good," or because not-dating can sometimes suck even more than less-than-ideal-dating. Maybe its simply because I really enjoy a woman's company, whether its something sexual or not. Maybe I want to distract myself from missing Shayne.

Enter Redhead Carla. A late30s insurance cubefarm worker and single mother to an adorable wee urchin, Carla responded to a listing that, completely on a lark, I posted to Craigslist. A few emails and conversations later, we met for coffee that didn't remain just for coffee. This sounds strangely familiar.

I'm learning to listen to my gut more. My gut didn't respond with starfire when I saw her picture, pretty though she is, and maybe even then I sensed that there could be gulfs between us. But, in the spirit of openmindedness, I decided to give it a chance anyway.

I really wasn't expecting anything to happen that night. I even more really wasn't expecting anything to happen while Carla's three year-old was goofily crawling around on the couch we were on too. But, no, there she was, hoisting her jeans-covered legs over mine to share some peckish smootches while I tried to suggest that maybe, if this was going to go down, it might be better after some tiny person was fast in Lalaland.

And that's how we ended up in her bedroom, her tiny pad pitch black in darkness, as these tactics were viewed as the best possible way for some tiny person to actually drift off to sleep. She did.

It felt totally weird to be undressing and preparing for unexpected sex in pitch darkness. The wee one would sense and respond to any light, I was told, so I smiled and tried to enjoy it, ignoring the thought that maybe I was with someone who simply didn't want to be seen naked. Turns out I was mistaken, but what did I know?

Her kisses seemed innocent, shy, reserved. I began to wonder how comfortable she was, but was well assured. Deciding to relax in the moment, I slowly brought myself down her nude body with kisses and teases before parting her open for a sensual session of head. I felt, rather than saw, that her mound was shaven and smooth, her clit small and responsive, her inner labia taut and finely sculpted. Gently sliding my fingers inside as I licked and sucked her, her G-spot was small and surprisingly smooth, difficult to tease. I enjoyed listening to her quiet gasps and sighs... and then it was over. She had had her cum, and sought to cuddle and drift to sleep. I was amiable. The pillow was too hard.

"Plans" seemed to happen quickly from there. We talked about what we were seeking in longterm relationships, Valentine's Day, that there's a musical happening in town that she'd enjoy seeing on her coming 40th birthday. Some of the yellow lights in my head started blinking.

Still, I'm openminded guy, and remained willing to give it a chance.

I made an excellent turchia scallopini for our second date, where we had already planned for her to spend the night. We were going to fuck, and frankly, as I hadn't enjoyed reasonably good sex since my last visit with Shayne and was very frustrated by the almost-theres through the past few weeks, it's safe to say that this time I had expectations. I deserved a solid, passionate night of getting properly laid, I told myself. My broken heart be damned.

After, it turned out, she could tear herself away from my PlayStation. After, it turned out, she matter-of-factly undressed beside the bed; no tender kissing, few caresses, no verbal teasing, no sensual play. Was she nervous? No, she said. Was she comfortable? Yes, she said. Yellow lights, yellow lights.

The nude snuggling was nice. Now actually seeing her, my cock hardened at the sight of delightfully round, small breasts teased with tiny eraser nipples, the pattern of sexy red freckles along her shoulders and forearms. She passively asked me to give her head again, and again I did with relish and tenderness, and again she came with sighs and gasps. When I drew myself upward again, she rolled me over, announced that the "cougar in her" was going to come out and mounted me. I bit my lower lip as I enjoyed her tight wetness and caressed her back, but too soon she was asking for a change in position and wanted me from behind.

Her narrow hips felt fabulous in my grip as I started fucking her deeply, earnestly, enjoying the sight of her pale behind ripple as my cock drove inside her. I shifted into one nuance of the position after another, and in time tugged her on her back and raised her ankles above my shoulders for deeper fucking. Carla gasped loudly as she felt me.

I tried not to think about the fact that this was a position that I really enjoyed sharing with Shayne.

And, again, then it was over. Perhaps because it had been more than seven months since she last had a man, but Carla had had her fill. Her pussy was done. And it became clear that she just wasn't the sort of lover who had demonstrable interest or experience in seeing her partner have a fulfilling time as well.

For all my openmindedness, I have to say it for what it is: that's a sexual selfishness. No, I don't need to cum every time I have sex to have fun, but as I know I try my best to ensure the best possible time with my lover, I really would like to see the same pleasurable excitement and sharing to have that sentiment returned. Call me crazy.

Other differences are apparent. Carla, for all her apparent sexual availability (if not skill), is a woman who seeks monogamy and expects The Man to open his wallet for all evenings out. She's not kinky. She doesn't carry a conversation. She doesn't express firm opinions. When I shared with her that its strong, confident women who have their own goals and know what they desire from life, from sex, from the future that attract me, and that women who wait to be rescued from their lives will almost always bore me to death... she seemed eerily silent.

It's a shame, really. And the selfish part of me wants to bitch that it's just fucking unfair.

She loves to camp and ski. We seem to have similar taste in film. Part of me enjoys the idea of corrupting her innocence. But the truth is that there are wide gaps between us, and that tells me that there really aren't any strong possibilities for LTRs. Make a friendship out of it? Sure, easy. Enjoy her company for so-called "maintenance sex"? Maybe. Not if she's going to expect anything more... I wouldn't want to be unfair.

But, no, bad sex isn't always still pretty good.

Morgan's birthday spankings.

She was perfectly relaxed and enjoying it. Prone on the futon, her breathing was just slightly staccato as my lubricated index finger very slowly penetrated her to the full and then slowly withdrew, pumping over and over and over again. I comfortably sat on the floor. I smiled to myself as I felt her sphincter grip me, and languished in the intimacy of the moment. As I casually probed her in the ass, I was reminded of childhood games of Doctor with my babysitter, those first moments in my not-so-total innocence when I discovered a passion for behinds, for lowering a girl's panties, and for the taking control of them as a partner lay on her stomach before me. I caressed Morgan's long, dark hair as my finger disappeared downward into her body.

"Hi. Well that was indeed an articulate and intriguing posting," she had emailed. Several days earlier, I had placed a Craigslist ad seeking a spanking partner and Morgan had pleasantly responded. "With my curiousity piqued and my poor neglected bottom tingling, I am taking a chance here and responding to you. I truly enjoy a proper over-the-knee spanking. It's my kink, what can I say."

"You can say, 'Please, Sir,'" was part of my reply. She liked that.

Morgan is a lovely, trim, intelligent, late30s brunette with the most charming freckles and sultry green eyes. She's both amusingly coy and passionately hungry. She possesses a balance between elegance and rawness that both intrigues me and keeps me guessing. She's new to dominant/submissive play, having had only one major partner in that territory that I know of, but that partner was not her spouse. Morgan is being a little extracurricular with her pleasures, and I'm respecting her choices as well as her need for discretion. She introduced me to a bohemian little bistro in my area that serves excellent tea. I introduced her to her g-spot.

My ad, originally placed before things with Shayne had begun to rekindle, had specified that I wasn't looking for sex. I wanted it clear that my priority was to find an intelligent, self-aware, sexually-sophisiticated bottom partner with whom I could indulge my Topspace and OTK fantasies. But it wasn't long before Morgan's emails elicited more from me.

"There's nothing quite like having made a bottom putty in my hands after giving her a sound spanking," I shared with her, "and watching her beet-red ass slink to the floor so she might service me and demonstrate her appreciation for having received her necessary correction."

"I happen to be a big fan of cocksucking," she replied. "I'm thinking some very salacious things... imagining the taste and feel of your cock for one..."

We met in the bistro for fruity sandwiches and Earl Grey. She was cautious when we spoke on the phone the day before, reminding us both that we might not clik after all, and that either one of us might not be attracted. As I strolled into the bistro and saw her smiling to me from her table, I sensed from her expression that she did not dislike what she saw. I liked her smile, and the hippie way her straight, dark hair flowed across her shoulders.

"Please share with me some of the fantasies that you have about being spanked," I had emailed.

"I fantasize being ordered to bend over and the various ways a proper spanking can be metered out, though not necessarily because I've 'misbehaved.' I like the idea of being taken over a man's knee and his firm hands kneading my flesh and various degrees of spanking. It's a pain/pleasure thing. I love the afterglow as well. The sensation lasts hours later."

Those sensations began in my parlor when she leaned in close for a kiss. She relaxed in my arms, her eyes half-closed, her breathing rapid as she held me and parted her mouth open passionately. I bent down, raised her shirt a little, and bit her tummy. I showed her around my place and we found ourselves in the den, enjoying my snake. We relaxed on the futon, and from our kisses, I soon slithered an arm around her and tugged her across my lap. The moment had come.

We were breathless, me feeling her weight on my thighs and knees, she still dressed in her black top and snug bluejeans. Her bottom was nicely shaped and perfectly framed in denim, showing strong lines and a sensual delve between her thighs. I paused to enjoy the moment, firmly wrapped my left arm around her waist, and made the first strike with my other hand. She wiggled as strikes followed, and squirmed when I would pause to simply squeeze her cheeks and caress her covered ass. It was fun, and my heart was beating faster. Reaching between her thighs to cup her mound, I could feel her warmth and excitement through her pants.

I tugged her by the belt and reached under her to undo it, the button, and the zipper to her jeans. I tugged them down over her thighs, revealing her pert behind covered in sheer black panties with cute black polkadots. She picked those undies especially for me, she said. How sweet. Sweeter still was my view when these were lowered as well, and the spanking continued as I throughly enjoyed the sight and feel of her delicious ass. Morgan's quiet gasps enriched me, reminding me of why spanking a partner turns me on, and her ass was gradually reddening darker and darker as I indulged myself at her tender expense. Her skin rippled just slightly, the occasional view of her winking rosebud heated me, but as she squirmed more and more readily, my cock hardened in my jeans and strained agonizingly.

I stood, peeling her pants and panties off. Kneeling on the floor beside her, I grasped her bottom in my hands and parted her open, revealing all of her secrets to me. She responded coyly, her eyes a little wider, just shameful enough to spur me on in possessing consensual control of her form. She went limp and gasped as she felt my tongue between her thighs and sliding deeper to probe and explore her.

Her ass was raised sexily in the air as I knelt above and behind her, gently feasting on her, pressing her lovely ass to my face, and tickling her rosebud with my tongue. This, I learned, was a first for her, but not the only one she would have that afternoon.

Morgan was panting and sitting upright as I sat on the floor before her, soaking my hands with Astroglide. She seemed nonplussed at my wanting to use lubricant at all.

"If I'm going to do to you what I'm going to do to you without this," I assured her, "I'm going to hurt you." She blinked and nodded. I smiled as I began to enjoy this privilege.

It's like being the man to take a lover's virginity. It's a privilege, sometimes an honour, and something that will always be remembered. As a man, I'm especially touched when I realize that I'm about to enter uncharted territory with a lover, and most especially when it's about a part of her own body that life hasn't given her previous opportunity to explore. Few other things could be so intimate.

I looked into Morgan's eyes as my dripping fingers began to part her orchid open. She had the cutest little dark racing stripe, barely wider than a lock of hair, her pussy otherwise completely bare and punctuated with a dark, adorable rose-bullet anus. Biting my lower lip in appreciation, I slowly entered her and gradually twisted first one, and then two, fingers inside her depths. Morgan panted and gasped, crying out when I'd surprise her with a few licks to her tiny button, but when I started to curl my fingers upward she completely melted before me.

Morgan's g-spot felt lovely against my fingertips, spongy and firm, and I held my hand in place as she got used to the sensation. Slow curling of my fingers followed, spreading them and closing them, wiggling them and stroking them, probing them and pumping them inside her tight and wet tunnel. Her eyes screwed tightly closed and she contained her screams as her chest heaved in her deep pants and gasps. I marveled at her sensual yielding, this woman who had been trying so hard to maintain some composure so far during our encounter. I twisted and pumped my fingers inside her as she rode the waves and sailed on currents she had not known before. She came in my hands and was in languid ruin when I finally withdrew from her quivering pussy.

We took a break. We talked. She lay along the length of the futon, nude before me as I sat, still dressed, on the floor. Her pretty ass was directly in front of me, and soon I was caressing and giving it light spanks again. Yet my fingers were still soaked with lube and her cum, and so what to do next only seemed obvious.

In the most relaxed, casual way, I touched her anus with a fingertip and slowly pressed to wiggle it there in slow circles. She rested her head on her hands and yielded to my touch, originally (and unecessarily) self-conscious about herself. Her eyes closed, her mouth parted, just as I began to feel her sphincter wink open and clutch the very tip of my index finger. Her warmth and the strength of her muscle moved me to probe further, and soon I was sliding into her tightness.

Very gradually, very slowly, but with more lube and eventually faster and faster, I soon had three fingers halfway inside her bum and was fucking her firmly with them pressed together in a cone. I twisted them and pumped them into her ass as she gasped and squealed before me now, but only for a brief while before withdrawing two of them and then slowing down once more.

"Well," she laughed after I withdrew two fingers, "I can safely say that never before have I been fucked in the ass like that!"

Morgan's body was relaxed enough, lubed enough, and had been opened enough, that my index finger alone was easily sliding fully deep into her now, and I enjoyed this little pleasure for some time. Her asshole felt heavenly.

Another break, and then we found ourselves in the bedroom. It was time I undressed, and still my attention was riveted to her bum. Things were stop-and-go for a while as we learned one another, and soon it became apparent to me that Morgan simply loves to be taken, no muss no fuss, no discourse no idle chitchat. She enjoyed my thickness in her mouth, and I enjoyed raising her ass in the air as I briefly fucked her there. But soon I had other ideas.

There's only one time when its perfectly reasonable to ask a woman her age.

"You told me it's going to be your birthday soon. How old are you going to be?" I asked.

She looked at the cieling and tried to stifle a laugh. "Um... thirty-two," she lied. I looked at her. She smirked.

"Um... twenty-seven?"

I looked harder.

She looked down and demurely whispered. "Forty."

I smiled wide as I yanked her across my lap again. I locked her ankles in a pair of leather restraints. It was time for Morgan's birthday spankings, and she squirmed petulantly as I held her fast in the crook of my right arm. Her lovely, bare ass was framed just under my shoulder, and my left hand rained smack after smack after smack as I counted off the previous years. Yet, unfortunately for Morgan, this was a moment when my gradeschool education failed me (seventeen does come after thirty-one, right?), so the poor, crying, whimpering dear likely received forty strikes with plenty of accrued interest.

She laughed when I took and showed her pictures. We relaxed for a while, and soon it was time for her to go. I've made a new friend.

Her spouse, the man who does not indulge Morgan in her wanton desire to be taken and spanked, forgot her birthday.



images George Nick, personal collection

The Law of Attraction.

In Western metaphysics, the Law of Attraction suggests that energy devoted into one particular direction will yield a returning energy based on the desire that's projected outward. Could this explain why, since enjoying a loving phonesex session with Shayne last week, writing about it, and then seeing it reposted on Fleshbot, I've suddenly been surfing on a phonesex wave? Not since the days since I did it for money have I enjoyed so many sessions in a given week.

My beloved Shayne in Illinois. The cockhungry Kay from Delaware (twice!). Haughty and naughty Carly in Ontario. What's going on?

Kay: off work early today, lucky me!
Me: Cool. :) Didja wanna play later?
Kay: Depends on timing. Stuff to do.
Me: :) (laughs) I have tasks too, but if'n ya get randy and wanna pencil me in, lemme know. *wink*
Kay: i'm always randy! ;)

I've made a new friend.

I encountered both Kay and Carly through the internet. I had begun this post to write about Carly, and the totally unexpected and serendipidous fun we had just last night, but once more the Laws of Attraction caught me in its swirling snare. Even as I began typing about Carly (and her penchant for getting rimmed... stay tuned), my new internet friend Kay suddenly texted me to say that she's taking time out of her day to jill herself.

Damn, I like that in a woman.

"I love that you call it jilling," she said to me once.

Kay: Speaking of randy, I believe I may indulge myself right now.
Me: [Pulling my attention away from the puter to read my phone] :) Oh really? Want some help?
Kay: sure but its gotta be fast. Have to leave in 15

Kay is a sexy, hot-to-fuck mid30s milf with a voice like a naughty teen who was just caught with her fingers dibbling in her pink La Senza's for the first time. She's active in her local swinging scene with her big-cocked partner, and we found ourselves networking almost by accident. We're getting friendly. She's already seen images of my cock, demanding that I send her some, and she's voiced her primal appreciation as well as her deliciously backdoor fantasies involving it.

Damn, I really like that in a woman.

We made small talk, caught up. "So... whatcha doin'?"

"I'm laying here on my bed... my jeans and panties are bunched down around my ankles, and I have my toy, and I'm slowly moving it in and out of my pussy."

This is the second time we've had phonesex. The first, just a few days ago, was a milestone for Kay: only once before, ever, had she had phonesex, and she was shocked when she came. She hadn't expected to, she said. She loved the sound of my voice, she said. I loved the sound of her surprise as she panted into my ear, I said. We've haven't met.

"I see... taking a moment out of your day for a little jilling, are we?"

She laughed. "Uh huh. I do that a lot on days I'm home alone, actually." She shared how wet she already was, talking to me calmly as she stroked herself.

This had to be a quickie. I began to tell her how I'd enjoy being on my knees before her, being the one to remove those jeans from her as I cupped her ass in my warm hands. I detailed how I'd like to be slowly lowering her boyshorts, watching intently as the cleft of her delicious pussy would reveal itself to me. How I'd kiss her inner thigh, slide the flat of my tongue to rest, unmoving, at her folds, just before beginning a slow swirl. As I spoke, I relaxed on my futon and casually stroked myself, sharing with Kay how my cock was slowly swelling in my fist, growing warmer and thicker, my palm softly brushing the spongy head.

Kay was sighing deeply. In my mind's eye, I saw her stroking herself with her dildo, craving for touch. I kept at her, detailing the ministrations of my mouth until, I said, I would stand up and whisper "the million dollar question" into her ear. My face would be wet with her excitement, I told her, as I bit her ear and asked.

"What do you want? Tell me what you want..."

She didn't pause. "Fuck me.... fuck me!" she hissed into the phone, her voice hungry and desperate for cock. For my cock. For my cock that's she's spent the last few days looking at pictures of. Looking at and masturbating her lovely, puffy pussy over.

"Then I'm going to spin you around, Kay, hoist your back, set your head to rest on the dresser, and pull your beautiful ass closer to me. I'll hold the base of my thick cock against you, swabbing my soft tip along the length of your wet seam, lubing myself with your sweet pussy. I'm going to spread you open, my hands on your ass and my thumbs hoisting your cheeks up while I give one long, slow, deep thrust into you, my cock filling you completely."

Her breathing quickened into sharp gasps, muffled moans, and throaty swallows as I heard her fuck herself with her toy. I sensed it sliding into her deeply, her hips thrusting upward to meet it, to meet me, as she got nicely fucked. Shortly after, her moans shifted into cries as she crested, shook, and came hard into my ear.


I'm still casually dating Connie, although circumstances lately have kept us away from each other. It's nice, but it's not going to get serious. Shayne and I are talking; we may even see each other again, may even be lovers again (she suggests), but it's also clear that she's trying to 'get over' Us. This new sparkly internet-friend-with-benefits thang with Kay has become an unexpected and welcome treat.

Interesting times.



images Bell Canada, Naughty Nati, Discretesex