Contest entry:Change Your Mind, Change Your Pleasure[F][M] | 2016

Change Your Mind, Change Your Pleasure

I dated a woman from the Northern mountains of CA, an inland island of surreal beauty, nestled deep in the Sierra Nevadas, just outside of Lake Tahoe. She was 20 years old Hispanic and Caucasian, with the kind of luscious hip flare you'd expect from a prime-of-her-life latina, combined with the tiny waist and pale complexion of a true small town farm girl. Her hair was long and deeply brunette, the color of corduroy teddy bears spun to silk, and hanging just below her belt line. Myself, so lucky to have pulled this angel from heaven was her perfect type: a lengthy 6'2", 195 lbs, and jet black hair I kept neat and long on top, with the sides short, and a fade all around to blend in naturally. My hazel eyes that turn a bright green whenever I'm in water or making love held her in rapt attention. Physically, we were made for each other.

We immediately fell into each other, fucking at every opportunity, at a Drive-in(there are still some left!), the living room floor after her family had gone to bed, and sometimes in her brother's bed just to be comfortable and crude. She loved making him sleep in our wet spot and never telling him.

As most small-town girls in my experience are prone to, she had some morals, there were lines she just wouldn't cross. A blowjob was a rare occurrence, and maybe to completion three times in our time together. It wasn't all her fault; I have a blessing and curse that it isn't easy to make me climax, and sometimes doesn't happen at all. There was never going to be a threesome. And, for all of the fantastic ass she possessed, it was completely off limits.

This, I had to break.

You see, I'm an ass man, and that's exactly the challenge I like. I'm not so much in to taking my pleasure from her ass, as giving it to a woman there. It's a fetish of mine, giving women orgasms, and doing it with a woman's ass is difficult and rewarding. Convincing a reluctant woman and then showing her how it good it can feel is my ultimate high.

But this one was going to be tough, she loved a good spanking, and sometimes two hand fulls of her ass in my hands got her moaning so deeply she'd explode and drench my cock and thighs within just a moment or two. Now for my size I have extremely big hands and long, slender fingers, so sometimes my reach was an 'accident' and fingertips would slide just into the crack of her ass. Never enough to separate, but enough to give me hope for something, someday.

It all changed when I bought her a vibrator. It was her first, and it wasn't the type you'd think. It was a Homedics, one that had a heat switch and speed adjuster, and had a strap that slid over the top of your hand. One day when she came home from work and she was extremely tired and I was out of mind horny from smoking some fantastic Sativa and thinking about that wonderful ass, it walked through the door. I showed her the massager I'd bought and told her to strip and relax. I'd rolled a blunt just for her, poured a Screwdriver with Jim Beam, and left it all on the night stand in the bedroom. I'd given her plenty of massages before, so it wasn't uncommon but she was still apprehensive.

"Don't get funny with that, she said." I know how you are, and I'm not sure about that thing. It looks crazy." It weighed maybe two pounds, with a thick knob at one end sculpted like a dome and the color of ebony.

I shot back at her, "Yeah I know, you know, now trust me and lay back."

So after stripping her onude,, I had her lay back, produced a bit of oil, and began rubbing it everywhere. I took forever. Possibly an hour, as I had every intention of breaking my vow, and doing as many dirty things to her as possible. I'd dug my thumbs into her thighs and calves, sliding them effortlessly through her strong legs. The Air-Climber she was obsessed with working out on kept me obsessed with her. I worked over her shoulders tenderly until they dropped, and her breath came deep and slowly. Eventually I paused a moment, and put my plan into action: Slipping the massager on to my hand, I turned it low, and settled it into her shoulder blade area.

"Oh..wow.." was all she said as I ran the massager over her back and shoulders, my other hand still busily caressing each leg, and slowly travelling up her thigh. As I made my way down to her waist line, she twitched under my movements, hips slowly pumping forward on the bed. I had to play this slow, too much would ruin this forever. I picked up the massager and moved it down to her calves, stroking each one upwards to where her thigh met the crease of each ass cheek, and rolling it away to her hip, just like an honor-bound gentleman supposedly would. Within minutes, I could taste her arousal in the air. There's nothing like the taste of latin pussy; spicy, warm. As I continued working her thighs, I spread her legs a bit with my hands. To my surprise she eagerly complied, like she was hoping and praying I'd ignore what she'd said and give her the sensation she was craving.

That's when I knew I had her. she was clearly emanating that delicious fluid and had formed a small pool just beneath her lips, and they were cherry red. Swollen. I ran the massager up in progressively larger circles, close to her waiting pussy, and then over each cheek of her ass, increasing the strength of the vibrations with the touch of a dial. She threw away any restraint she had, and began actively driving that wonderfully hot box of hers, it's hard clit at attention and fully visible, towards my hand and it's engine of pleasure. There was more to this than an orgasm for me though: I was setting up many orgasms to come, for the both of us.

I smoothly ran the vibrator just over the crack of her ass, so lightly, that it could have passed for a mistake. I rested the pulsing machine in my hand just the at apex of her cheeks, where they converge together, and gave a little pressure.

"Ohh, damn..." Was the reward I got.

I moved away, playing the game perfectly.

"Don't..."

Yes?" I said It was a rhetorical question; we both knew what she was after. I'd seen her hips lurch at the sensation. The vibrations were strong enough I could feel them through the bed, which means she could definitely feel it in her mound, but she could also feel it in her ass.

"Do that again." I couldn't tell if she was going to fall asleep or come right on the spot, her voice was so deep and relaxed. Hypnosis seemed like a real possibility right then.

I moved up, slowly running the massager head through the crack of her ass, deeper this time, and much more slowly. When I reached the top of her ass, she simply said,

"Down again."

I slid my hand down her cleft, a bit more deeper, and a bit more slowly. This time, the head of the massager parted her lips, and slid through easily. She was soaking. I could see her essence shining on the tip, the goose-bumps break out all over her body, and the sudden pressing back against the shivering engine in my hand. Her pussy swallowed the head, and I slowly began to turn my hand back and forth, moving in small circles, torturing her as I touched every part o fher lips and pussy but not quite giving her the clitoral stimulation I knew she wanted. By now she's given up any resistance, and she's slowly fucking herself on the head, trying to get more inside her, to itch her spots, to be filled up with the hot sensation that has her writhing shamelessly and on the verge of coming.

This whole time I've been staring at her ass. Each time she moves up to fuck herself on the massager, her cheeks open up just a little, and I can see her asshole has dilated a small bit. This massage has obviously relaxed her completely, normally she'd have been shy and never thrust her hips out, knowing that I'd be behind her and staring at what she knew I wanted. She's given up, and I can she NEEDS to come, and soon.

Time for action. I move the rotation of the massager from just between her pussy lips, to directly over her clit, and turn up the heat switch. She jumps at the contact, and her nails dig into the sheets, her mouth wide open. I can see the muscles in her ass and pussy flexing, faster and faster until it comes in uncontrolled spasms and I know she's almost there.

I slide a finger into my mouth, and check her breathing. I see her take a huge breath, and know it's the moment. She's about to bear down and have another one of the huge orgasms I love to drive her through. She presses her hips into my hand, and it spreads her ass for me to see my target perfectly: Her asshole looks like the top of a fresh orange, a slight indent; puckered and delicious. I press the tip of my finger to her ass just as she comes, and she screams her pleasure at me, I can feel it thorugh the mattress separate from the massager's vibrations. Her first time with a vibrator of any sort, and she squirts a stream of her juices covering my thighs and hips, and her ass draws my finger in, deeply.

I hadn't expected that, I'd meant to only rub her around her asshole, not push her boundaries too much this first moment. I'm ecstatic, ready to come myself, and haven't a stroke or touch to my cock since the massage started. That's when she buries her face into the pillow and begins screaming, fucking her hips at me again, causing my finger to slide in out a few delicious times with ease. She's shaking hard, almost crying, and her body is now drenched with sweat. I remove my finger, run the massager along her thighs and ass once again, bringing her slowly down from her new, stupefying high.

I reach over and brush the hair from her neck, kiss her face, and say, "Thank You."

Her only reply before she fell asleep next to me smiling was: "Next time..."