Teddy was listening to me whine about my woes with the smug expression of amusement he’ll sometimes give when he thinks he knows something I don’t. It annoyed me, but I really needed to unburden myself, so I plowed on.

“With Tiffany, everything sexual had to be so… delicate,” I griped. “I don’t mean sex with her was strictly vanilla, but anytime we did anything new, she would hem and haw. Even when she’d later tell me we’d done something she’d really wanted to do!”

Teddy nodded.

“It’s was like she was programmed to hold off on everything, so I ended up sounding like a jerk begging to try some position we hadn’t done before.”

“Gotcha.” Teddy was still sporting his wry smirk.

“OK,” I said sharply. “What’s with the attitude? You’re supposed to be my sympathetic friend.”

“I am sympathetic. Up to a point. But didn’t you go through this same stuff with Carole. And with Becky before her?”

It was a truth I’d been trying to avoid. But he was right. There was a string of girlfriends I’d broken up with for similar reasons.

I slumped back on the couch. Teddy went and got two beers from the fridge and said, “Here. We’ll toast your disastrous love life. Then we’ll figure out how to fix it.”

I was annoyed again, but I drank to the toast all the same. I knew deep down Teddy wanted to help.

“I think,” he said, setting his beer on the coffee table, “that you should try a different kind of woman.”

I rolled my eyes and challenged, “What should I do? Interview prospective lovers and make them say whether or not they’d want to do it doggy-style? Come on, Teddy!”

He smiled, more warmly this time, and replied, “I mean a different category of woman. A different age. Try someone older than you. Maybe ten, 15 years older.”

I waited for the punch line. When none came, I asked, “Are you serious? Why would I want to date a middle-aged woman?”

“Oh, lots of reasons, you twit. Set aside the distinct possibility that you’ve been brainwashed into thinking only young chicks are physically attractive. Consider my own field research into the matter. I’ve been fucking older women for years now. I’ve had more fun with them than any woman my age — by a big margin.”

I realized he was serious.

“Uh, like, what do they do?” I asked. I couldn’t help but be curious.

“They do it all, my friend,” he said with a grin. “At least the ones adventurous enough to go out with younger men.” He then listed a pornographic litany of acts he’d engaged in with these seasoned women. He extolled their unbridled enthusiasm. He praised their straightforward devotion to their needs.

“You’re a young fucktoy to them — and believe me, they will use you!”

I was intrigued, despite myself. I acknowledged that my not considering older woman “in play” might have been social indoctrination on my part. We get told all our lives, through commercials and other media, that youth is desirable above all else. Maybe that was just bullshit. Maybe I really needed to try somebody older. Somebody mature. Somebody truly experienced.

I muttered my thoughts out loud, and in response Teddy said, “Experience counts, my friend.”

He spoke like it was gospel.

When I furthered wondered where I might find myself an older woman, Teddy said, “There’s probably one right under your nose. Think about it.”

He was right. I did know an attractive older woman. Janine from work. She was in another department, but when we bumped into each other, she was always flirty. I hadn’t taken her seriously, because, well, she had to be in her 40s. I recalled she’d mentioned sending her daughter away to some big university across the country.

But as I pictured her, I realized she was in gym-perfect shape, with a taut ass and firm tits. In fact, the more I thought about her, the more turned on I got.

The next day at work, we ran into one another. When she gave me a sultry smile, I responded with, “Is this all a game, or do you want to do something?” I was nervous, wondering if I’d overstepped.

But Janine didn’t hesitate. She came closer and laid a hand on my arm as she said, “If it’s a game, I guarantee it’ll be a fun one. You want to come over to my place tonight?”

I was stunned. I’d never had a woman cut so immediately to the chase. I stammered out an affirmative, and she told me where to be that night and when.

Needless to say, I was useless at work for the rest of the day.

I showed up at Janine’s, half expecting all this to be some colossal misunderstanding. But when she opened her door in nothing but a negligee, my jaw dropped and my cock swelled.

She plastered a kiss on my mouth, then led me to her bedroom. With one quick move, she flung off the flimsy negligee. She looked absolutely smoking. I fumbled getting my clothes off, so her steady hands took over. Soon I was naked before her, my cock as stiff as a board.

We got onto the bed and resumed kissing. This time, it was a tongue-slavering affair, hungry and searching. She pushed her body against mine. She was both toned and enticingly soft. I laid a hand on her tit, finding her pert nipple completely stiff.

She pressed her shaved crotch against my cock, rubbing herself on me. She reached around to knead a handful of my ass. All the while our tongues danced. She kissed like a fiend. No hesitations, no apologies.

Her other hand snaked between us, and she grabbed my cock. I gasped at the firmness of her grip. She jerked me at an expert rhythm, unleashing pleasures deep in my body. I tweaked her tits and moaned into her mouth.

I moved my hand between her thighs, and she opened her legs. I stroked her slick pussy lips, marveling at how easy everything was. I wasn’t used to a bedroom environment that wasn’t fraught with vague tensions, with rules I didn’t entirely know.

With Janine, everything was apparently frank and blunt. She was shameless — in the best sense of the word. She was a sexual creature, and she wanted me.

Her mouth moved to my throat. Then she was quickly kissing her way down my chest and stomach. She pushed me onto my back and slid nimbly between my legs. Her hand cradled my balls, and I felt her breath on my swollen cockhead.

I cried out as her mouth closed around me. Her tongue darted across my knob, then I watched the tight ring of her lips slide straight down my throbbing shaft. She sucked my veiny length all the way down without a hitch.

The woman knew how to suck cock, and she obviously enjoyed it. An eager hum filled her throat as her head bobbed up and down, and I felt those vibrations coursing through me.

Suddenly, pleasure surged within me. I tried to warn her that my climax was imminent. But she didn’t let go, sucking me all the harder, and I did indeed shoot my load. I felt a little embarrassed at having come without having done much for her.

She seemed to read my mind. Wiping her mouth with the back of her hand, she said, “Don’t worry, baby. I’ll get you up again. Right now, I want your mouth on my pussy.” With that she lay back, raising her knees and spreading her legs.

Her pussy gleamed invitingly, and I was hungry to taste it. More, though, I was thoroughly aroused by how direct she was continuing to be.

I hunkered down happily as I took to my task. I breathed in her enticing aroma, then took a first lick of her. She grunted gratifyingly as I trailed my tongue up and down her outer lips, feeling how wet her pussy was.

When I probed inside, her hips rocked. I tongued her deeper and deeper, finding the fiery little bud of her clit. It was already swollen. I licked it, lavishing it with attention.

Janine cried out, “Yeah, boy! Eat my cunt!”

Those were unimaginable words from any other woman I’d known. They spurred me on. I softly jabbed her clit, smearing my mouth against her sopping pussy. She seized a handful of my hair and moaned loudly. Her juices flooded over my tongue, and I swallowed them.

But I wasn’t done with my oral endeavors. I put my hands under her ass, lifting and tilting her. Without hesitation, I jammed my tongue against the sweet pearl of her asshole — something I’d never been able to do with another woman.

Janine loved it and wailed, “Yes! Tongue-fuck my ass, you nasty boy!”

I probed her hole as she rubbed her clit, and soon she was writhing on the bed, yanking my hair again and crying out as she came.

By then, my cock was achingly hard once more. When I finally sat up, she grabbed my meat and growled, “Put this fucking thing in my pussy — right now!”

I mounted her, my excitement at a fever pitch. She was like a carnal wonderland. She was a hundred fantasies come true. As I slipped my cock into her waiting pussy, I gazed at her face. Her age was most visible there, but I realized with a kind of awe that there was nothing unattractive about her lovely features.

I really had been brainwashed. If this older woman could be this hot and desirable, so must be many of them. I’d been denying myself a whole category of women without even realizing it!

As I stroked into Janine’s velvety snatch, my pleasure climbed higher and higher and my skin tingled everywhere. The smack of our bodies coming together was sweet music in the sex-humid bedroom. I watched as yet another climax built within her beautiful body and swept over her.

I held back from my own orgasm and let her enjoy hers. She wriggled beneath me, and when she was catching her breath, I told her, “I want to fuck you doggy-style.”

She flipped over onto her hands and knees. I hastily moved in, put my hands on the globes of her ass and plowed her, pounding mercilessly. I looked down at her asshole, still shiny and wet with my spit.

“I want to fuck your ass!” I told her. Janine didn’t have any qualms and handed me a tube of lube. With her enthusiastic cooperation, I buried my cock in her fine fanny and fucked her frantically as she fingered her clit. When I came, so did she, yelling out nasty words of victory the whole time.