[M]y recent Craigslist hookup with a Submissive [F] wanting to explore her kinky side

She was average to good-looking, white, well-dressed and rather stylish, young-looking for her age, capable of intelligent conversation. She said she was 40ish, and looking to explore her submissive side. Her boyfriend wasn't into that kind of thing, and he had agreed to let her play with another guy…suggested it, even. She'd answered my ad which offered a safe and friendly introduction to Dom/Sub play, and things flowed smoothly. I enjoy helping a woman explore her sexuality, especially when it involves submitting to me.

She showed up to the hourly-rate motel between our locations right on time in her cute new-looking car. She walked in, and, as I'd told her I would, I greeted her at the door, shook her hand, and then pulled her in for a deep kiss, which turned into extended making out and me groping her. She'd told me she had only kissed a handful of guys in her life, and 2 in the last 15 years (ex-husband and boyfriend), so she wasn't sure how good a kisser she was. Turns out she was good. My hands sought out her sizable breasts over her colorful blouse and squeezed them hard. She mentioned she wanted them to be played with roughly, and that light pain was a huge turn-on, though she'd never really had that turn-on explored to her satisfaction. She moaned into my mouth in her breathy, high-pitched voice. It was a young voice, not quite "little girl," but definitely not especially mature. She sounded submissive, if a voice could do so on its own.

I then began to pull up, then reach up under her long skirt. I spanked her ass twice, hard, while our tongues were entwined, then grabbed it hard in both hands, spreading the cheeks. She pulled away and asked if she could use the bathroom. I obliged, and when she came out cleaned up a minute later, I said, "You are a much better kisser than you must have thought." "Thank you," she quietly replied, smiling, looking away. She was meek in the most submissive, but real way, and it was incredibly sexy. She was obviously nervous. "Undress for me, slowly," I said. I was already in boxers and t-shirt, and she dutifully took off her clothes slowly, bending over for me as she pulled her skirt down, as instructed. When down to her bra and panties, she apologized breathlessly and profusely for not wearing sexier underwear, but it was sort of a spur-of-the-moment decision to meet me, and she wasn't prepared. I cut her off. "Now take off your bra." She did, and shyly looked away as her tits were exposed to me. I grabbed them both, then sucked her nipples…right one first, pulling with my lips to test what she wanted. When I made my way to the left one, I sucked harder, and bit down on her rather large nipple. She yelped, but not in a bad way, so I sucked harder, and my right hand pinched her right nipple rather hard as I bit down on the left. She yelped/moaned at this. I slapped her right breast as I continued biting and sucking on the left on and around her nipple. She winced and moaned louder.

I reached my right hand between her legs, and, as expected, her panties were soaking wet. I pulled away from her breasts. "Are you enjoying this?" "Yes," she breathed. "Yes what?" "Yes, Sir," she corrected. "Good girl. Pull your panties down for me. I want to see how wet your cunt is." She quickly did as instructed. "Good girl. Now lay down on the bed." She laid down, and I spread her legs with my hands. Her pussy had a decent amount of hair on it, but it was groomed and clean. By now the hair had beads of wetness forming. "Rub your pussy for me. So you said you only cum from your toy? Your fingers don't do it for you?" "Yes, Sir, unfortunately my fingers frustrate me, I can never fully get off with them. It's my toy, and sometimes a real cock or mouth, that get me off, but the toy is the only sure thing." "Well, when's the last time you tried using your fingers while sucking a nice thick cock?" "I…guess…never? Or maybe in college with my husband…" "Hang your had over the edge of the bed, and rub your wet pussy for me." "Yes, Sir."

She wriggled herself so that her head was dangling over the bed. I stripped off my boxers and shirt and straddled my legs, lowering my mostly hard cock down to her lips. "Now suck my cock while you rub that pussy." She lifted her head up, opening her mouth, and taking the head of my cock eagerly into her. She sucked and worked it, gradually taking more. I lowered myself more, thrusting forward to see if she could take it all down her throat. "Tap my thigh twice if it's too much," I said in an even, warmer tone, without the demanding tone of my Dominant command voice. And with that I proceeded to fuck her throat. She couldn't quite take all of me, which made it more fun. She gagged and became very turned on when I pushed too far in. I rubbed her tits, slapped her tits, and then pulled my cock out of her throat, wiped some of her spit off with my right middle finger, and inserted it into her pussy while she rubbed her clit. She moaned, and I promptly stuffed my cock back in her mouth to feel the vibrations of her moan.

One finger felt tight, but she loosened up quickly, so I added another. Soon her hand stopped rubbing her clit. "Don't stop rubbing, be a good sub and cum for me. Don't think about it, don't pressure yourself. Stop thinking, and just do what feels good." With my words of encouragement, her hand went back to her clit and her mouth eagerly went to my cock. I started finger-fucking her harder, more deliberately. She was enjoying it, but there was little change. So I pulled my fingers out, and boldly spanked her pussy as she rubbed her clit. She moaned deeply and loudly into my cock. I struck gold. "You like that, huh?" "Mmmmmmm," was her reply. I spanked her pussy harder. "MMMMMMMMM." I buried my cock all the way down the back of her throat and spanked her pussy hard twice in a row, then kept my hand there, putting pressure over her hand on her clit. The moaning got more intense and her writhing began. I got so turned on, I started to feel my own eruption. I pulled out and shot huge spurts of cum all over her tits, then her mouth as the shots got weaker. Her orgasm continued as I came. The ice was broken. I was unbelievably turned on, and still hard.

"You like having your pussy spanked, huh?" "I guess I do, " she replied, averting her eyes. We both giggled a bit about it. "Was that a good orgasm?" I asked. "Yes, it was better than I get with my toy. Very different. Much more intense." "Good. Let's see how it feels when you cum from my tongue." And with that I spread her legs, lifting one in the air, kissing my way from her toes up to her thigh, then diving into her pussy with my mouth open and tongue out. She was so incredibly wet. I lapped at her dripping cunt for a few moments before getting my lips and tongue fully wet with her sex and coming up to kiss her with it. "Taste yourself." I kissed her deeply. She licked my lips and sucked my tongue, moaning. She tasted better than I'd expected, and she enjoyed it as much as I did. I kissed down her tits, biting each before diving back down between her legs. I quickly found the amount of pressure and speed she liked, and how rigid she enjoyed my tongue being by studying her moans and movements. Within 3 or 4 minutes I could tell she was close to cumming. "You must ask permission this time," I said into her thigh. "May I cum now, Sir?" "Ready to cum again so soon?" "Yes," she blurted out between moans. "Not yet."

I went right back to exactly what was working, a stiff tongue moving across her clit with some force, felt her wetness increase, felt her shuddering, holding back. "Good girl. You may cum on my tongue now." And she did. Hard. And I held her down, wrapping my arms under her thighs and curling them back towards me, not letting her get away. I kept licking fervently and she kept cumming, squealing at times, squirming uncontrollably, trying to get away as the sensitivity went through the roof. I then buried my tongue in her cunt and held it still, feeling it pulse and quiver. I moved it lightly to tease her, and with each gentle movement she gasped and twitched.

I was rock hard, and I had to feel her pussy wrapped around my cock. "Good girl. Now it's my turn." I put her legs over my shoulders and slipped the Magnum on. I teased her with the tip of my cock. "Ask me nicely for the whole thing." "Sir, may I please get all of your cock?" "Now beg me like a slut." "Sir, please fuck me with your whole cock." And as she said the words I slid into her quickly, fully. She moaned, and I put a hand around her throat to feel the vibrations in her voice. "Since you've been a good sub for me today, you get to be properly fucked." I began thrusting more quickly, then backed off, pulling my cock out, and then re-inserting it sharply. I did this maybe 10-15 times. I rested her legs on my shoulders, took my hand off of her throat and placed them both on the bed on either side of her shoulders. She was bent nearly in half, and I began thrusting with all of my weight, slowly. Then I'd do a fast and extremely hard thrust, our skin slapping together. She came again within 3 or 4 minutes.

I flipped her over, laid her flat on the bed, spanked her ass hard several times, and entered her this way, grinding my cock into her. I grabbed a fistful of her hair, pulling it, and rubbed and spanked her ass with my other hand. "You came 3 times today, didn't you?" "Yes, Sir." "And I've only cum once. Tell me what a bad girl you've been, and how badly you want me to cum inside you right now." "I'm sorry, Sir, I've been a bad slut today for only making you cum once, please cum deep in my pussy now." "You want me to fill you up with that cum, the same cum you still have on your chest?" "Yes, Sir. Fill my pussy, please?" These words get me every time. My orgasm came within seconds, and I made sure she felt every twitch and spurt as the condom filled up. I always cum a lot, but today both of these orgasms were just insanely huge. I moaned loudly at first, then less intensely with each subsequent thrust. Finally, spent, my cock slid out of her. "Good girl," I said with a wide smile.

We cleaned up, she took a quick shower to get the cum off of her. We had some small talk, she expressed how great it felt to cum so much, how different it was from how she'd been cumming recently, the politics of Dom/Sub relationships, and the origins of her submissive tendencies. She said she has having boyfriend trouble, and he thought opening up the relationship sexually might help, so she took him up on it with me. I was so glad she did!

Source: reddit.com/r/gonewildstories/comments/3f14zf/my_recent_craigslist_hookup_with_a_submissive_f