The Tomboy, or my relationship bootcamp.

I recently shared a photo essay with you where I featured a series of black&white images of past partners and their lovely bums. For fun, I later added a wee poll to collect your thoughts on which images you liked the most. Most of you responded (with an honourable mention for Shayne and the Grrl) to the Tomboy.

Her name is Reese. A soldier in her mid30s, she was the first playmate to message me through (wait for it...) a dating site. I was still in post-Grrl angst at the time, and apart from a five-star-hotel two-night stand with a computer technician from Vancouver, she was the first woman I had sex with since that breakup. It was therapy.

She was literally hanging in a tree when I picked her up on our first date. Clad in jeans and a diving Tshirt, she made no bones about the fact that she was a casual presence, and if I expected heels and garters, I'd be sorely disappointed. Little did she know that most of my women friends were of the punk, dyke, bohemian variety, so we got along just fine. In fact, we were inseparable for the next four days.

Like the Grrl (and me), the Tomboy was polyamorous. Unlike the Grrl however, she was very physically active in a wide variety of esoteric sports, possessed the energy of a caffeinated dynamo, and had the build befitting her training as an infantrywoman.

Among my favourite memories of her include the time we went to the annual carnival. As we stood before a game of shoot-the-pop-cans-with-the-pellet-gun, Tomboy ignored the sexist tauntings of the hawker. "Give it a try... if you can, little lady." A crack markswoman, Tomboy readjusted the sights on her popgun and downed can after can after can after can to the hawker's silent disappointment. She got the giant green froggie.

I wish I could say that sex with the Tomboy was as great. Sadly, for me, her repetoire was severely limited. While she felt comfortable enough to expand her horizons with me, including her first anal experience (which she was amazed by but never quite got over her anxiety to try again), there was a laundry list of activities she simply had a boundary over. Further, her sexual energy worried me, as sometimes she seemed to behave as though she were used to only being sexual with men who didn't give a crap about her at all.

"Ok, I came, I'm done," she said from under me during one night. I had been fucking her as she lay on her stomach, her legs pressed together so that her cute ass was high and tight against my pelvis. "You can finish now," she added, and turned her head to the side as if to wait for me to do just that.

I was so shocked that I almost got up and left the bed. I did stop, actually, but I didn't leave. It was one of the unsexiest things I had ever heard, and it prompted some deep conversations later. With the Tomboy, her zeal for sex never quite seemed reconciled to her distant, aloof energy during it. In a few months, I grew tired of feeling unfulfilled by my partner. While the Tomboy was gradually making "improvements" (in my view), that didn't stop me from playing the poly card and eventually begin seeing someone else as well.

Stef, about whom I'll write in the future, was sexually the complete opposite to the Tomboy. What frustrated me then was that while the Tomboy seemed to have her life together except for the sexual compatibility, Stef was very sexually compatible but had no life. It was a very annoying dynamic for me at the time.

Eventually, exit Stef. I started to withdraw from Tomboy. Codependence. High maintenance. Distant, fragmented sex. The writing was on the wall. I would soon discover Shayne through the same dating site, and I would learn what loving happiness would feel like again.

But not before one sexual evening with Tomboy that actually does stand out in my memory. A friend, fellow soldier, and fuckbuddy of hers, Ethan, was visiting. Tomboy was torn because Ethan had expressed interest in some play, but it was a night she and I had reserved for ourselves. When I casually suggested that Ethan could "join us if you desired it," the look on Tomboy's face was precious.

It hadn't been since days (and nights) with Diva that I had been in a male-male-female threesome. Gentleman that I am, I yielded a lot to the guest as Ethan and Tomboy coiled on her large bed. A well-built guy with short dark hair, Tomboy was bobbing her head on his long cock (something she learned to enjoy after all while we were together) as I took her from behind. Ethan and I traded places every so often, and she squealed with squeezed-shut eyes as he slid his dick into her. The highlight of that evening for Tomboy was when Ethan revealed his bisexuality to me, and I indulged in a very very rare escapade of sucking cock myself. (Surprise!) Taking his girth in my fist, Tomboy was gasping as she jilled herself, wide-eyed and open-mouthed, her hand a blur between her thighs, as she became totally engrossed in watching me blow him for a while.

(Oh, get over yourselves, guys.)

If dating the Tomboy was a rebound for me, somehow I managed to keep my heart on the steady. The disparity between our emotions become more and more apparent, with me never quite going past the friendship, friend-with-benefits stage, despite dating her for almost a year, and Tomboy secretly hoping for a matrimonial proposal.

The bottom line was that, over time, I saw how there simply was no daily-life compatibility for us. Had the sex been great, had she not possessed certain elements that estranged me, maybe I could have considered things longer. But in the end, I simply had to accept that as far as primary partnership was concerned, there wasn't a future. I learned a lot about what I did, and didn't want, by dating her. That's not entirely a bad thing.

I tried to wean her gently. Soon, the poly card came into play on her end, and she met an unemployed yoga instructor who caught her fancy. Once she started beaming with new-relationship-energy again, I made the break. She didn't take it well. Her LiveJournal became interesting. But time has passed since then, and we remain friends. She's good people; she's just too whacked for me as more than a friend.

The irony in submitting this post about her right now is that not long after I strike the key, I'll be biking down to her regiment's mess hall to have a few beers with her, her still-unemployed yoga instructor, and other buds of ours. I haven't been there in months. It'll amuse me to enjoy my pint in the knowledge that I've shared about her here.

She does have a cute butt though, no?

images personal collection

She's an unresisting puddle of pink flesh. Oh my.

"I'm a Rogue groupie!" emails the deliciously breathtaking Coy Pink (or as some Urban Roguery readers know her, the artist formerly known as Jill). "Your words are enough to melt us (ladies) into unresisting puddles of flesh. Keep it up!"

For me, corrupting innocence is a vocation. Could it be that the tawdry musings of the sexual blogosphere have slowly caressed their unspeakable ways into the libido of this elegant and articulate woman? Could it be that her pulse quickens to the oysters splayed before her as she embarks on a (pink) tide of sensual awareness? And most importantly, people: will she kiss and tell?

Let's hope so!

HNT with snake.

Roane, or how my cordiality got some exercise.

Roane messaged me through a dating site. We enjoyed a few phone conversations, nothing greatly sexual, and developed a nice rapport. She gushed to me. It was nice. Fresh out of an unhappy 9-year marriage with a cold fish, Roane had given me every impression that she was a woman who was eager to make up for lost time. She seemed eternally grateful that I wasn't potentially seeking to pin her down into another primary relationship, and that I was encouraging her to make the world her oyster. She laughed when I suggested she get a male stripper with her friends to celebrate her now-bachelorette status in the burbs. Very quickly, I got the sense that she and I would get along well.

We made plans to get together. I made it clear that I didn't have preconceived notions. She made it clear that she did, and asked me what she could include in her overnight bag.

Previously, we chatted over MSN. Roane: So you really did phone sex?

Me: *smile* Uh huh.

Roane: Was it hard?

Me: The work? No, not really. I enjoyed it. My cock? Sometimes, but not always. *wink*

Roane: So... can I unzip that jacket you're wearing?

Me: Just watch me lean against the wall, raise hands over my head, and smile at you while you do so.

Roane: I'd like to lick up your chest to your lips and spend some time lingering there, sliding my hands on your chest.

Me: My deep babybrowns will laugh as I enjoy you. A tongue on my chest. Nice. I have very sensitive nipples for a man.

Roane: Open your shirt. I'll nibble my way to your nipples. To lick them, suck them.

Me: Mm. Please.

Roane: I bet you smell good.

Me: I'll enjoy caressing your hair, small kisses on your head as you tease me. I wear natural oils. Sandalwood and patchouli mostly.

Roane: I'll run my hands around to your back and massage you there for a bit. Kisses intensifying. Lick all the way to your navel. Down the dusting of hair.

Me: You'll be seeing a happy bulge in the khakis before you.

Roane: I can see that you boldly want to come out...

Me: Can you see how your attentions make me swell? Can you see the outline of the crown of my manhood covered in green?

Roane: I run my hands down to the front of your khakis. Yes, I see!

Me: It's been a while since you enjoyed a man in your lovely mouth, isn't it? Take your time. Enjoy it.

Roane: I want to lick you. Can I lick you?

Me: I like it that you ask me that. Please do.

Roane: I'll unzip your fly at first. Lick your shaft. Then I'll take you in my hot mouth and devour you right down to the base of your throbbing cock. I'll stroke your balls and gently squeeze them... Mmmm, you taste so good. I love the taste of a man.

Me: And I enjoy being squeezed gently. Especially as your lips nurse on me. I am earthy, and just slightly salty, like sea spray.

Roane: God. You are making me wet... I'm just wanting u inside me.

Me: I like knowing that.

Roane: I remove the last of your clothes and drag u over to the bed.

Me: My cock is warm and thick. I'm cut, and I shave my sack nicely smooth.

Roane: I LOVE that. I'm the same: neat and tidy. I push you down and impale myself on your swollen shaft...

Me: *bites his lower lip as he watches you with a glinting eye*

Roane: I ride you slow at first and then gradually pick up speed... Then slower again as I lower my lips to yours again and lick and suck your lips. I want u to be fucked by my wetness.

Me: My arms will coil around your waist, pulling you on top of me, holding you to my chest. My hips thrust upward and I can feel your warmth, your silk, your wetness seething down the length of my cock.

Roane: Mmmmmm. Yea. And we move like a well-oiled machine. Up and down, up and down, pressing together.

Me: One hand at your shoulder, gripping you as I return your kiss, the other holding you by your lovely ass, parting you open as I fuck you.

Roane: I love you holding my ass.

Me: I'd love to feel you shake on top of me when you cum.

Roane: I want to feel u come for me. I want you to scream my name while I kiss you madly.

Me: Then rest your weight on your hands, above my shoulders, so I can hold your ass with both of mine. Feel me caress and squeeze your bottom while I thrust hard and deeply into you. Let me pull you down to impale you on my thick, twitching cock.

Roane: Mmmm yes... That feels awesome.

Me: My balls are soaked with you. My girth parts you open and gives you fullness.

Roane: I'm dripping with sex for u...

Me: Let me look into your eyes, feel your head fall to my chest, hear your gasps right into my ear while I take my turn in taking you now, even from under you. Listen to my deep voice call your name as my cock thickens.

Roane: Mmmmmmmm that is what I need. I want your cock.

Me: Feel my gifts fill you with pulsing warmth and heat, a man's richness and power thrusting into your lovely body and filling you.

Roane: Our bodies are slick with sweat. I feel throbbing, mmmmmm....

Me: Take my cum. Milk me. Feel me explode inside your depths.

Roane: So pure, your gift...

Me: I will shake, growl, and strain. I'll be left panting and used under you. You've taken me.

Roane: I guess I win! :)


Swingerwife asks how the date went, so here's the scoop: I picked her up at the train station. With her blonde hair, tats, and demeanor, she reminded me of Diva. We went to one of my favourite bistros and talked over salads and juice. We discussed her salon business, my hair, her dragonfly tattoos, her dogs, and decided to do some shopping and get her some shorts to wear on a very hot day. First, we figured, back to my pad to drop off her bag.

And that's when I got a fresh lesson about others who could have preconceived notions. I already knew that Roane was embarking on a new world for herself, but after all her yeah-baby-I-wanna-do-this-with-you talk (and there was a lot of it), I hadn't at all expected that this was only her means to build up her own confidence. Zing came the 180-degree turn.

The one sexual experience she had since her very recent separation? She forced herself. Meeting me and deciding already that she was going to stay over? She was biting off more than she felt she could chew. She wasn't ready, and blushingly, stammeringly told me so. Or maybe she didn't feel a spark (I was attracted, but it wasn't fireworks). Or maybe the planets were out of alignment. Or maybe she didn't want to miss Lost. Whatever.

I made light of it. No big deal. Why be ungenerous?


Oh. And my inspiration for the cybersex? Yeah, fine, ok, I'll admit it. It was all Shayne who was on top of me.


thumbs FetishPornPics, Sweet Fresh Tails, Pepe's Adventures

Milf and nookies.

For reasons that I don't fully understand, it seems that Aphrodite is being generous. Have I finally traversed an important obstacle? It would nice to believe that I'm overcoming a significant karmic hurdle.

Like contrasting sisters, Connie and Roane seem to be coming into my world. Both are 40+ independent women, dog-lovers, business-owners. Both have experience under their belts. Both also just happen to be HSV2-positive.

Connie, as I recently mentioned, is an Italian paralegal and financial planner with a downtown condo and a slobbering English bulldog. Roane is a Canadian salon owner, a bikerchick from a quaint little Ontario burg with two gigantic, black poodles. Connie is Versace, Godiva, and cappucino. Roane is bluejeans, tattoos, and Harley Davidson. Connie is kidless. Roane has two punker boys. Connie picked me up through work. Roane messaged me through an STD-aware dating site.

Suddenly, having HSV feels like being a part of some unseelie elite, some sexually outlawed club with secret coded handshakes and wink-wink-nudge-nudge-hey-it's-ok-we're-in-this-together cred. This seems totally bizarre and yet, totally liberating.

And how is it that my dating curve has suddenly swung from mid20s artist to mid40s milf? It's been years and years since I've known a lover (not that anything has happened yet) who was older than I. So strange. I wonder how this will all turn out.

Before stepping forward, one kiss to Shayne.

Hello, baby.

I want you to know that I love you.

You come here from time to time. I'm glad. There's something I wanted to say, and I wanted to do it before these hot and randy people (like us) who've enjoyed reading about the pleasures we had shared. I wanted to say this here because you have a unique position (two, really) in that you alone, to date, are a lover who reads this blog.

When I started this three years ago, it was a way for me for rekindle my Top headspace when The Grrl and I were together, when she was encouraging that in me after my ruined marriage had tempered it. This blog began as a way to enhance what she and I had, and that's why after she and I broke up, this blog became silent for more than a year.

My life went on, and eventually I encountered you. I still remember how you took my breath away when I saw your "fancy" picture. Do you remember our first posts through that dating site? Do you remember the delicious way the energy in them shifted when I scolded you, daring you, threatening you with a spanking? Even from afar I thought I could feel the sudden tightness in your chest as you read those words. I think that was when my heart really began to sing out toward you.

And then, to my surprise, I told you about this. We had been enjoying intense and imaginative phonesex then, and I was delighted as I learned more about your sexuality, your openness, your womanhood. Your openness was so great that I sensed you would enjoy reading this, and so I shared. It thrilled me when you said how this blog enticed you, turned you on. After letting it go dormant, you became an inspiration for me continue it. In time, and for a while, I almost felt that we were a team as I shared some of our exploits and you would remark "anonymously."

"You are my favorite rogue. You walk lightly on heavy boots. You tread delicately over sacred, yet unfamiliar earth. You embrace it all, from irritance to complexity. You fear only conformity and betrayal. You are a smart one. You try to learn from every moment and succeed in learning. You give me the benefit of your lessons learned freely and patiently. You whisper beauty."

You told me once that, having read through the archives, you were jealous of the love my posts had demonstrated for The Grrl. I listened, smiling to myself because I loved you now. So, with things having since altered between us, I want you to know that now you and she have that in common. Further, in your own ways, both of you can rightly be called my Muses because both of you are Her daughters who have brought me to this place. Any regular reader who enjoys this blog has you to thank. I know I do, and for so many gifts.

Perhaps, in some way, I've returned the favour to you as you begin sharing your pleasurable Strawberry exploits on your own blog. You write well. I would have enjoyed collaborating with you.

I do miss giving your body, and your spirit, pleasure. It's been six weeks since we were last together, since we last felt and loved one another, since we ended. Rather than the textmessages that came later, I prefer to remember the parting we shared as we stood on the corner of Ontario and St. Clair, just before I kissed and hugged you, turning aside for a cab. We both have had some dates since then. I haven't known a lover since; perhaps you have.

But things are moving forward for me, as I expect they are with you, and it's looking possible that I'll know a new lover's arms in the near future. Before I proceed, I wanted to take a moment to acknowledge all of this, you, and what you have done for me. It feels a little weird, and that can only be because, for me, you had stopped being "just" a lover and had started to become a partner.

I would have liked to nurture that chance for partnership between us, the blessing in that seed. You remain in my heart, my mind, in my passions, and I know you already know that given the opportunity, I could still enjoy that pursuit with you.

What higher praise could I offer someone who has known me so intimately?

This blog will eventually reflect what directions I may move forward into. Since our break, posts have focused on past events, playful entries, photo essays and the like. Eventually, I'll write about experiences in the "present tense" again. Though I'm moving forward, and though this blog will eventually reflect that, I'm writing this now because I want you to also know how special you are to me and will remain.

I want you to be shamelessly happy, baby. I will envy those who will come to possess your touch, for I miss it and remember how you craved my own. I want you to drink deeply from love and passion's cup, and to have a beautiful, fulfilling life. You know how deeply, dearly I hope to still be a part of your life, but no matter what happens by will or Fate or passage of Time, please know that you have touched me as richly as you have told me I have touched you, and that the thought of you will come to me with every future caress I may receive. At the very worst, I still regard you as my Friend, and one of my best.

I could have seen myself betrothed to you, Pixie.

I want you to know that I love you. There is, still, birdsong inside the egg. Namaste.

Re: The Talk

I was fully prepared to be told that it couldn't work. I was fully prepared to accept the worst possible consequences. I even brought chocolates to soften the blow when I opened up the conversation.

And then she blew me away.

Connie has it too.

Everything could be just fine. And there's more to tell...

The Talk.

It destroyed my love affair with Shayne. It changed things with Veronica.

Lately, I've been casually dating Connie, a 40-something Italian paralegal and financial planner, who's perhaps one of the most elegant women I've ever come to know. She picked me up while I was at work, and we've been enjoying dinners and coffee for the last little while. Connie has made it abundantly clear that she's after my bod.

Tonight, I plan to share The Talk with her. I'll let you know how it goes.

She's hooked.

Now that she's foolishly told me how hooked she is on Urban Roguery, I'm thinking that it's just a matter of time when Swingerwife's spouse is in an adjoining room with my PlayStation, and she and I are all alone.

That's right, baby: some chilled wine, soft jazz, you in a teddy on a sumptuous bed, and me on your lap. I can just picture the glow of the monitor screen on you right now. Yeah.

Local girl makes it good... sort of.

After posting about my teen experience while working in a Brooklyn deli, I found myself reminiscing of home. Google and I had some fun.

It turns out that 90s skin starlet Bianca Trump and I are from the same neighbourhood. That amuses me, even if it's true that the former self-styled "Italian Princess of Porn" (or "Latin Princess of Porn," depending on what boxcover you're reading) became just a little confused later in life.

A pack of Marlboros, half a pound'a provolone, and some thick, juicy cock.

Floozy. Tramp. Hoo-ah. These are words that my grandmother would have used to describe her.

I grew up in an old Italian/Irish neighbourhood in Brooklyn. Long after the Koreans, the Poles, and then the Lebanese started to come, its older roots continues to show itself on the Hudson shore landscape through the success of two specific businesses: churches and bars. Churches and bars, bars and churches, churches and bars. On some streetcorners of my childhood domain, you can spit in almost any direction and be confident to strike one or both. Churches and bars.

And delis. There's nothing quite like a New York bagel.

I was eighteen and fresh out of high school. When I wasn't wasting time getting hammered with friends or contemplating a career in the US Navy, I was earning graveyard-shift minimum wage at a 24-hour delicatessen. With shatteringly bright flourescents and massive windowpanes, the place was a beacon to the three bars within walking distance to it.

Coffee regular. Pack a'smokes. Coffee. Smokes. Gimme a roast beef with lettuce and mayo. Smokes. Six o'Bud. Regular. Is the baloney fresh? What, no knishes? Coffee. Wanna buy some weed? Six o'Coors. Regular. Got a buttered roll? Smokes. Smokes. Coffee. Plain with cream cheese. Smokes. Smokes. Got matches? Smokes.

The bars closed at 4am. After the Drunk Rush, I could usually expect some quiet until around 5:30, when the first wave of the Worker Rush would wander in. This was my break time, when I'd fix myself a killer sandwich and sneak a beer (or two) from the cooler. I had settled down behind the counter and was burying my nose in a book when the little bell above the door jangled.

She staggered in, trying to keep a little balance. Her long and kinky bleach-blonde hair tossed itself in almost every direction, partially hiding her face from my view as I looked over my Stephen King novel. She did the I'm-just-beginning-to-sober-up-I-think waver as she stood in front of the beer fridge for what seemed like a long while, occasionally chuckling to herself.

"Hey," I said.

She turned to look, smiled. "Hey." Her head bobbled just a little while she continued to look at me, her smile widening before she turned back to the cooler.

"Hey, uh, hey, can I get a pack of Marlboros?"

She closed the cooler without having taken anything and walked toward the register. As I took her money, she smiled and brushed some hair out of her half-closed eyes. Just under 5-foot, she was about ten years my senior and wore a white buttoned shirt open just below the neckline with white striped running shorts. She gently kicked at the counter and floor with her matching pair of gym shoes as she watched me. Her lips were curled in a smirky way, and I noticed that her pale pink lipstick was smeared just a little.

Kinda makes you wonder what she had been up to.

The scene broke when a few stoners came and left. I filled a few orders. She hung around.

I had started filling and stacking coffee filters in preparation of the morning rush. She wandered toward the back counter where I was and rested her arms there. In the corner of my eye, I noticed her trailing small circles on the counter with her finger, tapping it with a polished fingernail, her face lost in 4am post-drinking thought. She quietly said something, but I didn't hear and asked her to repeat herself. Her eyes darted over her shoulder, and when she saw that we were alone, she looked to the floor and faintly whispered.

"You want a blowjob?"

I spilled coffee grounds on the floor. I blinked a lot. My mouth was open.

"What?" I whispered back.

She was looking into my face now, smirking, her eyes still half-closed but alert. "Yeah..."

I didn't believe what I had heard, but that didn't stop me from locking the front door and affixing a quickly-scribbled sign. "Be right back!" She waited for me at the rear of the store, and I lifted the hinged countertop to let her past. Space was tight behind the counter, so I led us through another door and into a rear storeroom. My heart was beating like a drum in my chest.

Stacked boxes of paper coffee cups, coffee filters, grounds, and the like filled a corner. A pallet of soda cases, beer cases, Snapple cases stood nearby. Unused candy racks. Cleaning equipment. Clean rags in plastic garbage bags. One lone white, plastic, deck chair. The flourescent lighting buzzed and beamed mercilessly bright. The room smelled like coffee grinds and bleach.

She was faintly shaking, and returned my kiss gently as I leaned against a stack of cardboard boxes. Her hands roamed over my wide chest and down my legs, and I squeezed her ass as she pressed her breasts to me. She tasted like cigarettes and booze. She gripped my package in her hand, kneading my crotch and bringing me to fullness. I couldn't believe what was going on, and was terrified that my boss, the night-owl that he was, might make a surprise entrance at any moment. Sex was still reasonably new to me and I felt completely out of my league, but I wasn't going to pass this up. I was awkwardly squeezing her tits when she started tugging at my belt and undoing my jeans.

"Yeah, get these off," she said as she undid the zipper. Tugging at the waistline, she pulled me toward the plastic chair and pushed denim around my ankles before beckoning me to sit. Rough edges from slots in the chair bit into my skin. I widened my knees apart and slouched slightly, bringing my cock and balls over the edge.

There were no preliminaries. Kicking some flattened cardboard in front of me, she knelt down and immediately started to suck. She took half of my length in her mouth with her first stroke, and her lips felt dry. One or two strokes later and her saliva started to coat me, her lips encircled me smoothly, and she started to feel really good. I leaned my head back and gently held her head. I was a kid getting blown by a half-drunk woman in the back storeroom of a Brooklyn deli at 4:30 in the morning. Holy fuck.

Her hair was brittle, chaotic, and smelled like cigarettes and Aqua-net. Her head moved like a rotary piston as she drew her neck back on the upstroke and foward on the down, taking me deeper each time she sucked me in, only occasionally bobbing her head vertically. Her hands stayed at her legs, and mine held the chair as I felt and watched her. Soon, she was picking up speed and her saliva started to seethe down the length of me. She breathed quickly through her nose, and I felt heat and moisture building between her face and my crotch as she worked me.

mmm mmf mmph mmmmm mmf mmph mmf sslrp mmm yeah that's nice you've got a nice dick sslrp i like it baby mmf mmph mmmf tastes good mmf nice mff

Her spit was coating my balls now. I was gripping to the armrests of the plastic chair, holding myself up as the slots starting to cut into my skin uncomfortably. This also let me thrust upward, and she started to suck me harder and faster while I jabbed my cockhead into her mouth.

I heard knocking on the glass door out front. I ignored it. I lost track of time. She sucked me, and her sloppy wet mouth started to feel more and more intense. Her temples and the nape of her neck were moist with sweat, but she kept going.

And then I felt the back of her throat against my cockhead when she opened up for a long and deep slurp down the length of me. Pumping into her mouth, listening to her hard breathing through her nose, feeling her perspiration on her head and face, I burst my cum into her deliciously slutty, wonderfully skanky mouth. She stopped bobbing her head rapidly but continued to suck, squeezing her lips around my cockhead and feeding off of me. I collapsed in the chair. She knelt up, dazed, breathing hard, eyes closed, mouth agape, her nipples stiff in her shirt. Her lips looked swollen and wet.

She used the bathroom. Thank God, but no one was at the door when I peeked back into the deli. I was exhausted from the hour and her servicing me, and regained my composure. The sun had started to come up. It was almost 6am. I furiously started to make coffee and get my act together, and had already served one or two annoyed-looking customers when she emerged from the back room. I had completely missed the first wave of the Worker Rush and my shift would be over soon.

She left happy. I had given her a bag full of goodies: cold cuts, bagels, this and that. Sipping a coffee, I watched her teeter on a bicycle as she pedaled away with the plastic bag of delicatessen goodness in her hand.

We never exchanged names.

I got fired shortly after. I wasn't worried about it. I would later meet Diva after I essentially joined the circus.


You know, it's really hard to get a decent deli sandwich in this town.

thumb Tempting Gals, Wikipedia, Flickr

She's such a sweetheart.

I'm pleased to share that Sweethart is among the loyal readers here at Urban Roguery. I always enjoy it when another shameless vixen rubs elbows (or, in this case, impressively magnificent breasts) with me.

thumb Top Notch Titties

Photo Essay: Behinds loved, loves behind.

"...How beautiful are your sandalled feet, O prince's daughter! The curves of your thighs are like jewels..."
- the Song of Songs

Diva

Janelle

the Grrl

the Tomboy

Veronica

Shayne

Blowjobs, basements, brotherhood, and Fleshbot.

This summary is not available. Please click here to view the post.

Sunday mornings were made for lovemaking.

My cock is hard, thick and warm between my thigh and the silk sheet. I am surrounded in comfort, dozing as I wake from slumber. A purring feline snuggles beside me.

I catch myself smiling as my mind drifts, and the pillow cradled under my arm reminds me of the Grrl's waist, its softness in my palm the softness of her tummy. The arch of her generous hip, the warm seam of her womanly behind meeting my leg, stirs in my memory. My hand would caress her tummy in restfulness, smooth itself upward to gently cup and hold her right breast, and a soft pat on her bum as I would waken and leave the bed.

Or of Shayne, sweet Shayne who continues to haunt my mind and heart and bring me to tears with her absence. In the bed of her charming one-room flat, I'd snuggle against her and rain kisses on her sleepy, scrunchy face. The morning light would glint against her sexy nosering. 'Showering my love on her,' she'd slowly waken and start to giggle, and she would feel warm and delicious and sensual as she clung to me. Her belly made me smile. She would mumble an 'I love you' into my chest as she buried her face in me, my arms tight around her. Her thighs resting against my shoulders as I would later taste her, the feel of her round bum on my lips as I kissed her there, her morning groans shifting to morning gasps as she felt that first slip of my hardness into her as the cool breeze drifted across the bed.

I miss these ladies. I love these ladies. Dancing with a crowd of anonymous women during a salsa festival yesterday, I almost came to weeping as I thought of how strongly I love, appreciate, and adore women. I live for women like Shayne and the Grrl, and my heart is filled with fullness when I remember joyful, sensual moments with them.

Remembering them and their wonderful bodies beside me in the morning sustains me when it's a cat snuggling at my side. I smile to myself, my chest swells, and I think of them.

Namedropping.

I thoroughly enjoy networking and sharing with others of like mind. Today, I enjoyed the serendipity of meeting two unique women whom I'll enjoy mentioning.

Miss Mitzy Cream and I met on the street today, me having recognized her from some past burlesque performances in my city. What a complete delight, and totally gregarious with her current plans to produce a set involving a 6-foot gramophone. She kindly reminded me that the Toronto Burlesque Festival is happening this weekend, so perhaps I'll have more tales to tell of some of the deliciously empowered women in this area who breathe new life into this sensual craft.

On a fetish-oriented networking site, I've also come in contact with Canadian fetish performer Maxine X. We met recently during a fetish social party, and now I'm enjoying some correspondence with her as we talk shop. Perhaps I should make an effort to see one of her DVDs now, mm?

thumb Miss Mitzy Cream

A kiss for a muse.

On a personal note, I'd like to share an open thank-you.

In addition to the lusty summer season, I must admit that in telling you about Jenny, I was also inspired by the exquisite little behind of a delicious partner-in-crime out here in the blogosphere. Really, boys and girls, you owe it to yourselves to equally enjoy Ms. Inconspicuous as much as I.

You make me salivate, beautiful one.

thumb The Seduction of Infidelity

What I did on my summer vacation (2).

At a sensual, clothing-optional gathering in the southern US some summers ago, I met Jenny. Jenny was deliciously cute, and while our respective partners were (consensually) elsewhere at the time, she had already given me a great blowjob in the basement of a turn-of-the-century mansion on the campgrounds.

Jenny was lithe, sweet, and charming, with thin shoulder-length blonde hair that clung to her face in the summer heat. I could easily wrap my entire arm around her torso, and I adored her cute little butt. The sight of it, two melon-like semicircles seen from above her as she had knelt before me while servicing my cock, was what sent me bursting across her drawling tongue.

We didn't get to know one another enough for her to open up to me about her furry fantasies, but the idea of her fantasizing about it as we enjoed each other kinda amused me. I wish I knew what anthropomorphic stuff was going on inside her pretty head as I fucked her.

And I did fuck her, twice, after our fun encounter in the basement that year. She approached me the next day as I was working in the registration booth for the gathering. I beamed when I saw her, and my girlfriend at the time gave me the most sarcastic, sexy smirk as she witnessed it.

Jenny and I still had the problem of finding privacy, but I settled that as she and I hung around the Mansion again. as much of an escape from the heat it was, I wanted to avoid the basement again if I could, and my salvation came when I borrowed a room key from another friend. My friend, a buxom blonde with as scandalous a reputation as my own, also smirked sarcastically as she handed me the key with a nod and a wink.

"Just don't use the bunk," she said. No problem.

Ok, I cheated a tiny bit. Taking Jenny by the hand and leading her through a crowd of other staffpeople, Jenny giggled as I brought us inside the small first-floor room. Sunlight peeked through the drawn, heavy drapes in bright shafts that pierced the otherwise dark and cluttered room. Personal camp gear, backpacks, clothing and the like were scattered on the rough floor of dark hardwood timbers. The bunk was small and unmade, but I sat on its edge for a few moments as Jenny removed her Tshirt while we necked.

Her small breasts were pressed firmly against my chest, her nipples taut and at attention, while I caressed her bare back. She undid my shorts after I removed my boots. She lowered the shorts to the floor, dropped to her knees, and took me in her mouth. I closed my eyes and rested my weight on both hands as her lovely head bobbed slowly. The sound of her suckling made my blood race and my cock thicken in her mouth, and she gasped when she withdrew me to get some air and lick her lips some more.

But by now I desperately needed to see her ass. Standing, she adjusted and kept sucking me until I bent over, kissed her head, and lowered myself to the rough floor between her and the bunk. I kissed her, tasting some of my own salt on her sweet lips. I reached for her button-fly jeans and undid them.

She smiled and knelt up, giving me room to lower her pants, but gasped when she then suddently found herself across my legs and my arm coiled around her tiny waist. Her pants were in a bundle around her ankles, and as she steadied herself, I slowly lowered her cotton panties and revealed her beautiful butt to me. It was a perfect, small behind, with high cheeks like split melons covered with just a hint of light blonde peachfuzz. My cock stiffened against her belly as I caressed her ass and started giving her a light spanking.

We knew our time would be short, since we were borrowing someone else's space, so it wasn't much longer after that before I shifted her as I pulled my legs from underneath. She found herself on her hands and knees now, facing some backpacks and a shaft of light from the covered window. She licked her lips, swayed slightly, and peered at me from over her shoulder as I marvelled at the sight of her bottom and perfectly bare mound. I reached into my shorts, retrieved a condom, and slipped it on. She watched, eyes wide, and returned her gaze to meet mine silently. Her mouth was open in anticipation as she looked at my cock, and she swallowed hard.

With one hand at each cheek, fingers spread and palms warm, I parted her sweet little ass open gently. I bent over to tease her tiny dimples with the tip of my tongue. I bit her. I eased back and straightened myself, guided the tip of my cock to her folds, and slowly started to push the head of my cock inside her.

"Oh my God," she said, but we hardly spoke. Building up from slow, shallow, and steady strokes, soon she was bucking herself back against me as I fucked her deeply. I was amazed at how tight she was, and her grip on my cock had me gasping loudly. My hands held her hips and I pulled her away and back toward me easily. Her body was such a contrast to the Grrl's, whose womanly hips were wider and her thighs stronger, but I revelled in the diversity I found in Jenny's teeny form.

The floor, perhaps more than a hundred years old, was rough and demanding on our knees, and soon we were simply ignoring the pain while I bucked against her, taking her, making her voice shake as she tried to stifle her cries. She was so easy to manhandle that her pert ass smacked against me loudly and wetly as I thrust, swirled, poked, and fucked her full of dick.

A loud knocking at the door happened just as we both were straining to cum, and I laughed as I begged for just a few moments longer. Both Jenny and the female voice on the other side giggled as my friend walked away. A moment or two to regain some focus, and Jenny and I came in a rush, my cock swelling to a bursting point as I let go.

We quickly dressed and rejoined our friends, sweaty and exhausted. I grabbed us both some beers from my private stash, and we enjoyed the teasing of other staff members for the rest of the afternoon. Jenny's boyfriend later picked her up, and she blushed as she waved bye to me. Her knees looked ruined.

The gathering was almost over when we saw one another one last time that year. Most nights, the majority of the event's guests could be found around the main bonfire, itself adjacent to a wide river. Djembe and ashiko drummers would entrance all as people danced, swayed, and enjoyed the fire, the drums, the starlight. A few bottles of this or that would cheerfully pass between friends. Lovers would kiss in the glow. Poi dancers would spin their small torches in a mystic cyclone of delight. It was, in its own way, a delicious way to find the divine.

On one of these bonfire nights, Jenny ran into me and took my hand. We found a spot in the darkened wood where the brush surrounded us, but we ourselves enjoyed a small clearing at the base of a tree and against the riverbank. There, we settled on the wet grass in the darkness, the glow and thrum of the bonfire and its dancers faintly heard through the foliage. We talked, enjoyed ourselves, and soon fell to the earth in a casual embrace.

Jenny nursed on my cock slowly this time, enjoying me, before climbing on top and riding me deeply. I caressed her tummy, her tiny hips, and parted her beautiful little ass when she fell against my chest in ecstacy. We spooned in the grass. Swans coasted in the river beside us. Despite the condition of our knees, she wanted me to finish by taking her from behind again, and I gladly did. Our orgasm was casual, relaxed, and comforting.

I never saw Jenny again after that. We corresponded for a short while over email, but soon that faded too.

I haven't had opportunity to go to a similar event this year. I had hoped to take Shayne to one, and to introduce her to the sight of a bonfire through the darkened trees while enjoying me inside her. Alas.




thumbs Cat Dancing With Omaha, personal collection

What I did on my summer vacation (1).

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The little sex party that could.

It had been years since I last attended a sex party, and even longer since I attended an event with such a diversity of interests and people.

I've enjoyed some time off in these last two weeks, and so I took opportunity to turn Pride this year into a personal adventure of sensual debauch and revelry. I needed it. After a burlesque show, a fetish social, a barbecue at a leatherbar, enjoying the Dyke March, and other assorted events throughout the city, I was ready for a nice conclusion. Late last week, it seemed fitting then to end my carnal cabaret with a sex party at one of the city's more bohemian clubs. For me, Pride this year was about straightfoward, sensual fun.

There's an unwritten law somewhere in the annals of sexual adventure that when word gets out that an open sex party is happening, single men will flock there in droves. You can smell it in the air.

I settled somewhere comfortable and began scanning the club, finding myself receiving a sexy smile from a brunette at the bar. It took me a moment before I realized that it was one of the evening's t-girls who was checking me out, and I smiled back while smirking to myself.

Now, for all the experiences I've enjoyed in my life, I've only been with one transgendered person, and that was early in my sexuality. It came as a serious shock to me actually, because it wasn't until after the fact that I had been informed. (Another story for another time.) Still, while not my typical scene, I'm open enough to acknowledge attractiveness when I see it, and must admit to the occasional fantasy or j/o session there. Transgendered partners remain largely uncharted waters for this particular slut, although FTMs intrigue me.

Apart from dancing and drinking, precious little was happening for the first two or three hours of the party. Bisexual porn played on a few monitors. A large blonde woman in a black corset and a charming bare behind socialized with friends. A deliciously boiish lesbian couple came, found their place at a table, and snuggled casually. A cluster here or there of seminude gay men chitchatted. Several transvestites of all ages did their best to appear bored. Individual, and presumably single, men milled around.

The brunette t-girl eventually strolled onto the dance floor and find a partner there to neck with. Their play soon developed into the first scene of the evening.

As dancers moved around them, she kissed her male friend passionately. The club was clothing-optional tonight, and it wasn't long before Guy had stripped and they were making themselves cozy on a small mat at one end of the dance floor. Pressing close, Brunette removed her top to reveal a very firm pair of breasts with tiny dark nipples. She dropped to her knees, her back to the rest of the club, and he steadied his breathing as he looked down to her head bobbing slowly.

A small circle formed around them as others watched. A second male and t-girl couple settled right next to the first pair as Second Guy lay on his back and found himself cradled and caressed by his partner. The two couples played side-by-side while several males started stroking their cocks as they stood or sat nearby. Others continued to dance. Still others mingled elsewhere. In the rafters overhead, along a catwalk that led to some private booths, even more watched from on high.

In time, both of the males found themselves on their backs, next to one another, on the mat. Their trans lovers, both striking in appearance and demanding in their sex, mounted the men in unison to get fucked. As the music thumped and the crowd watched intently, each t-girl brazenly returned the gazes focused upon them as they took their lovers in their ass, pumping and grinding themselves unabashedly.

I leaned against the DJ booth and enjoyed my drink as I casually watched this little escapade. I noticed that a heavyset Asian woman, dressed casually, was trying to peer over my shoulder to enjoy the scene. Politely, I invited her to stand in front of me, which she gratefully accepted. We made small talk as we watched the trannies fucking some fifteen feet before us.

To our left and below a small flight of stairs was a wooden restraining stanchion, a single beam set at an upward angle and bearing steel rungs for leather restraints. A blonde milf in a red dress was soon brought there by her gentlemanly companion, whereupon she leaned her torso against the beam. He slowly raised her dress over her hips, revealing her bare ass. He produced a riding crop from his belt and began administering some gentle discipline with it as two other men stood to enjoy her breasts. She rested her head and chest against the polished wooden beam, eyes closed, experiencing the sensation with tiny gasps.

My voyeuristic companion and I smiled to each other as we enjoyed them. We introduced ourselves. Yvette was married and there with her husband, who shook my hand between his long bouts of being elsewhere in the club as he abandoned his friendly spouse to the wolves.

Bad form.

Sex parties, especially good ones, are very tricky to organize. Even among a pre-screened group of like-minded people, it's always possible that someone, somewhere, will misbehave or otherwise act like an ass. At the very least (and apologies to my gender for saying this), its unfortunately true that when single, individual men are permitted to attend, the odds are that one or more of them will be the first to fuck up. Why? That's another topic.

But I wasn't too surprised when one guy, standing near Yvette and me, began poking into her personal space like a penis without conscience. Not wanting to assume any authority over this woman's experience, I quietly stood by, though directly behind her. After all, I wasn't one of the staff at this club; it wasn't my place to assume he was overstepping himself as he touched and groped and pursued upon Yvette's person.

Her body language was clear however, even if she barely opened her mouth to set boundaries apart from an "I'm fine, thank you" to Mr. Dick. Why isn't she speaking up more, I asked myself. Where was her fucking husband? And why aren't the staffpeople here paying closer attention to the scenes happening around them instead of picking up empties? My feminist awarenesses started to wreak havoc on my Top headspace.

"Are you ok? Is this guy making you uncomfortable?" He saw the look on my face and started to back off from Yvette. I felt like I was working the clubs again, but this time I didn't like it.

Yvette wasn't visibly distressed by Mr. Dick, but she wasn't having fun either. Realizing that she was new to all this and that I had done the right thing, I pointed out the posted rules-of-behaviour signage (in oneplace and with very small print) and explained that she could always go to a staffperson if she felt uncomfortable.

Still, I felt ridiculous in that I essentially ended up filling in the roles both her husband and the staff should have quick-booted themselves to. This party, I quickly realized, needed some serious help with its infrastructure, else a major incident could be likely. Despite the opportunity for genuine pansexual play, I was left unimpressed.

Me, I carried on however. Yvette's husband eventually showed himself. By then, the trannies had moved on to other men and the blonde milf was giving her partner head at one the tables near the dance floor. Other t-girls, singles, couples of various orientations had arrived and were either dancing, playing, or drinking. It was getting late, and soon my newfound friends were getting ready to go. Husband, however, couldn't resist texting Yvette when he momentarily vanished again. A friendly black fellow, he struck me as a bizarre cross between Urkel and PeeWee Herman.

Husband: I think u shld show him ur tits

"He wants me to show you my tits," Yvette laughed to me.

"Do you want to?" I smiled. She smiled back as hubby returned again, then lowered the top of her dress. He invited me to touch them. I asked her. She blinked, smiled, and said yes.

That was when I found myself holding my first pair of breasts in a little while. For me, the tunes and the dancing and the chatter all suddenly stopped as I beheld her.

I've been craving to touch Shayne again, it's true. This moment with Yvette, these few seconds of simple touch, were a small salve for me. All of my Prideweek playfulness came down to this small, tender moment.

Yvette's tanned skin glowed under the strobe lights as she revealed a large set of firm globes, capped with soft dark nipples. She wavered a little when my hands gently cupped them from the sides, squeezing lightly, and then caressing underneath and over them in a slow, tender stroke. I bit my lower lip as I enjoyed them for perhaps a hint of a moment longer than she expected. Her eyes were glazed as I moved back with a grin.

They left, smiling.

Me: That was yummy. :)
Yvette: Thank u! I had a great time speaking with u. Hope to see u again! :o)

The night was about over me too. I drifted to an upstairs area where I explored the various privacy booths that had been arranged. More bi porn showed itself on monitors, and I relaxed with another beer as I watched one on a long red leather couch. Some of the transvestites made themselves available for passers-by in the nearby booths, but by then it seemed the evening was drawing late for everyone.

A larger play area at another end of the club began drawing a crowd of onlookers. Trust those wayward single guys to sniff out the one interesting scene in a playparty, boy. Mr. Dick practically went running in that direction once it appeared to be a place of interest. I laughed to myself as I waved adieu to the disappointed TVs.

And so my evening ended as I, shoulder-to-shoulder with a crowd of desperate males, watched a blonde BBW in a red teddy with matching stockings take on three black males as she knelt over a spanking bench. One husky dude fucked her slow. Two stood near her head as she tooks turns between sucking their cocks, much to the silent pleasure of the crowd that had gathered around them.

Mr. Dick, clearly frustrated with his total lack of success with the ladies, biological or otherwise, pushed his way through the crowd to stand directly next to the woman. Quietly focused on her own cocksucking and the fucking she was receiving, she hardly seemed to notice when Dick suddenly, characteristically, groped at her swaying breast like a grocer trying to date a mango. I rolled my eyes. The dude to my immediate left, one of the guys whose cock was getting casually sucked, didn't miss a beat as he simply pushed Dick right out of the way.

It was almost 4am. I smirked about that as I finished my last beer and headed home.


thumbs Tranny Surprise, Pain Vixens, Wild Rhino, Dacahard