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."