Rose and I had hooked up a few times, but this was easily the most fun we’d ever had.
Rose, a 26 year old, is 5’6, very skinny, with auburn hair, big brown eyes, A cups above a taut stomach, and a goofy grin that never fails to make me smile in return. Also one of those lovely asses that isn’t *phat* but is round and perfectly grabbable. I’m 5’10, 155 lbs and athletic. Covered in tattoos and chest hair, olive skin, thick beard, and hazel eyes.
Like I said, we had been together a few times, and then I got busy with vacation, some live shows, and friends in town. We made plans to see each other again, but it wouldn’t be for another five days or something, so I wanted to make sure the excitement she exhibited in making the plans held until we actually met up. Sp I started sexting her. Not too lewd, too fast, but the broad kind of “I can’t wait to make you feel good,” “I’ve been thinking about those cute little moans you make,” that sort of thing. She’s not very kinky or experienced with anything other than vanilla sex, so I didn’t want to push it, but she seemed pretty receptive to this (brief side note related to her lack of experience in dirty talk– she told me that she once had a guy say “Roll Tide” as he was cumming fucken lol what a chud). I pushed things a little further, reminding her of some of the other dates we’ve had, how well she rides me (the only position she’s ever cum from penetration in), how good she tastes, even including a bulge pic or two (after asking her consent, of course). I got pretty detailed, and she was eating it up. She told me how wet she was getting, how much she was blushing at work, how “hungry” she was getting– her preferred euphemism for horny… I kept it up all weekend. I told her how I’d tease her, how I’d drive her nuts, how I’d wear her out before I even took my pants off. I broached the subject of getting a little kinkier– using restraints, of having her pose for me, of some extended teasing– and after going over her limits and what she was interested in exploring, she was on board to experiment.. By the time she left work the day of our date, she told me she was a mess.
I waited for her at my house and she brought a bottle of wine. We drank in my loft, occasionally kissing and letting hands wander, but I was always quick to cut things off and keep her arousal simmering without bubbling over. I could feel how wet she was through her yoga pants by the time we decided to go to my room. I had her pose on my bed, while I sipped my wine and circled her, examining her slender curves closely. Occasionally I’d give her a spank or a stroke, and I eventually had her undress to her underwear for me (a white and black zebra pattern thong). I continued the torture until she was literally shivering with anticipation.
I then took out my under-mattress restraints and used them to secure her arms to the edges of the bed while I kept up the teasing. I blindfolded her with a necktie of mine and kissed nearly every inch of her– her neck, her collar bone, her breasts, her stomach. I skipped over her panties for now, peppering her thighs and even her calves and ankles with kisses. I began rubbing her down, too, massaging her legs and occasionally brushing my fingers over the wet spot in her thong, telling her how sexy she was the entire time. I started kissing her very lightly through her panties, hooking my arms around her hips and keeping her from bucking into my face too hard. I peeled her thong off, relishing how soaked it was with my fingers and admiring her freshly shaved pussy. I didn’t go straight for it, though, much to her chagrin. I danced around it, able to detect the delicious scent of her arousal in the air as I spread her legs a little farther and planted my first kiss on her lips.
She shivered and groaned loudly, and I blew on it, eliciting a giggle and a frustrated whimper. I began eating her out in earnest, simply making out with her engorged lips and enjoying her taste. I buried my tongue as deep inside of her as I could, making her squirm until I replaced it with a pair of fingers. I held them there and massaged her inner walls, finally zeroing in on her g spot. With my tongue licking her clit firmly, once I began curling my fingers, she started cumming. Howling her orgasm and bucking her hips, she even squirted a little bit (a first for her) and convulsed until I let up. Quickly reaching for a condom, I unceremoniously took my shorts and boxer briefs off. She was lying there almost catatonic until she felt my fat tip against her. I bent her legs and held them up as I sank in, resulting in a deeply satisfied groan from the both of us. “Just fucking wreck me,” she said, the most vulgar thing I’ve ever heard from her mouth. And so I did. No gentle build up, just straight pounding. Like I said, she had never cum from this position, so I wanted to undo her restraints so she could ride me, but it felt so good. I pounded away, getting close to my own climax. I was leaning over her, my arms wrapped around her as her face was in the crook of my neck. Unexpectedly, I heard her say, “Oh holy fuck I’m gonna cum.” I immediately tensed up, as hearing that usually makes me cum, but I managed to bite my inner cheek and keep at it until, a few moments later, “Alexxxxx oh god yessssss,” and I finally let go, cumming with her.
We caught our breath and I finally undid her restraints, and when she had the energy, she started raving about how good she felt. She said it was the first time she had ever squirted, as well as the first time she had ever cum from that position. I was in heaven hearing that of course, and it actually got me a little hard again. She noticed and went to go down on me. I almost pushed her away, as I’m not a big fan of blowjobs, but she seemed so enthusiastic, I just couldn’t. She got me hard enough for me to grab another condom and have her ride me. I simply laid back and let her do her thing. She likes the riding that’s more of a back and forth than an up and down, and that’s fine with me. It felt so good to let her grab my chest and go at it, while I grabbed her waist, kissed her breasts, occasionally smacked her ass. She came a couple more time and collapsed on me, apologizing that she couldn’t finish me off again, but I told her not to worry as I started gripping her hips tightly and thrusting up into her from the bottom. Lifting my ass from the bed with almost every thrust, I eventually was able to cum again. I held her tight and was too wiped to even take the condom off as we cuddled up and threw on an episode of Mad Men to doze off to.
Source: reddit.com/r/gonewildstories/comments/dbxisv/helping_a_vanilla_friend_get_a_little_more_kinky