She wore a buttplug to our first date [mff]

The first fun surprise of the evening came when Diana took off Kasey’s panties to reveal the pink buttplug she had been wearing the entire night. She said it was to train herself to associate anal stimulation with her erotic experiences and eventually be an “anal goddess”.

We met Kasey on reddit, thanks to our posts here and on /r/dcandbaltimorer4r. She described herself as thin, blonde, and blue-eyed, but she didn’t tell us just how gorgeous she was. We exchanged pictures and found out that way. She told us she was looking for something more than a hookup, but less than a poly relationship. Basically, friends with whom she could explore her sexuality. And that’s pretty much everything Diana and I want, so we made plans with her as soon as we could.

We met her at a bar near Diana’s and Kasey was wearing this olive green dress that she looked amazing in. She said it was one of her colors, and she was right. I (5’10, athletic, tattooed, brown hair/eyes/beard) was wearing black pants and a blue henley and Diana (5’4, busty and petite, hazel eyes, a short brown bob, and a killer smile) had on a tight pair of blue jeans and a black top. We talked about our jobs, dating, and she was very curious about our non-monogamous relationship. That’s pretty much our favorite topic of conversation, so we happily answered all of her questions and eventually went back to Diana’s after a couple rounds.

We got a couple more beers, put on some music, and, while I was in the bathroom, she told Diana she was a little nervous. Diana’s suggestion, of course, was to have me take my shirt off. We talked about my tattoos, then Diana’s tattoo, and Kasey asked about Diana’s pierced nipples. That led to a few giggles as Diana came to where Kasey was sitting on the bed and began kissing her as I watched and stroked Kasey’s back. Diana got Kasey to unbutton and eventually take off her dress to reveal a maroon bra and beige panties. The thigh high boots came next, while I got to squeeze her wonderful ass and watch as Diana removed her top and jeans. The girls got back on the bed and I began kissing Kasey as Diana got between her legs, where she discovered Kasey’s plug.

As Diana tasted our new friend, I continued making out with Kasey and experimenting with holding her arms down, putting my hand on her throat, as well as nibbling on her neck and her ear and sliding a hand under her bra. Diana got up at one point and said something like, “I’m good at this, but he’s truly the master…” inviting me to change positions with her, something I was happy to do. The bras were removed, and Kasey got to play with Diana’s pierced nipples, which they both loved. Meanwhile, I was in my happy place– my face was between a woman’s thighs.

She was already very wet thanks to Diana, but I kissed and lightly bit her inner thighs before dragging my tongue along her swollen lips and moaning at how good she tasted. I kissed her hooded clit and made out with it for a little while before burying my tongue inside of her. I kept hearing her moans and curses, so I revved things up a little bit and slipped two, then three, fingers inside of her. I simply held them there for a while, letting her get used to the sensation of them adjacent to her plug. Gradually, I began using them to stroke her g spot. With my lips applying pressure to her pubic bone and keeping her clit trapped, I was able to give her her first orgasm of the night. I felt her gush a little onto my hands, but she curled up in that adorable way girls do when they’re a little overstimulated. I let her down easy, only taking my fingers out very, very slowly. I crawled up to kiss her and we grinded against each other a little bit, but Diana was already donning her strapon.

Kasey removed her buttplug, content with her Pavlovian progress for the night, she got on her hands and knees on the bed. I removed my pants, leaving just my briefs, and slid beneath her so that her face was above mine. I held her steady and kissed her as Diana penetrated her from behind. Getting to hear her moans and feel the way she’d grip my chest or bury her head into my neck was amazing. We made out while Diana fucked her and slapped her ass, and I reached a hand beneath Kasey to stroke her clit until she couldn’t hold herself up anymore. I told her what a good girl she was and kissed her ear and neck until Diana pulled out, saying, “Now Daddy’s going to fuck you, ok?” She agreed enthusiastically and got on her back as I got a condom.

I held her knees up and apart as my cock dragged along her slit, slipping the head in and sinking in to the hilt. She told me I felt incredible and, between heavy breaths, told her that the feeling was mutual. I got a good rhythm going, from tip to base and back again, getting deep inside of her as Diana was watching us intently. She had taken out her hitachi wand and was using it on herself as Kasey and I changed positions. I let her legs fall on either side of my waist and brought my chest against hers and we kissed as we continued fucking. Burying my head in her neck, I could feel my orgasm coming, and I gritted my teeth as I pounded into her. I listened to the occasional curse or moan of “Daddy” in my ear and came hard as she wrapped her arms around me. Diana later told me she also came at this point, still using the wand as she looked on. After several moments of collecting myself, I pushed myself up to kiss her and then rose to remove the condom. Kasey pointed out that Diana was the only person not to be given an orgasm, so we decided to rectify that.

Kasey volunteered to go down on Diana, but only if I showed her how. Unable to contain the smile of my fortune– having one girl ask my guidance on going down on another girl– I agreed. Diana got on her back and spread her legs, and I told Kasey exactly how Diana likes to be eaten out. I directed her to just make out with Diana’s pussy first, to kiss is softly and romantically. My eyes traveled from one girl to the other, and I had my hand on Kasey’s ass as I guided her further, showing her how to pull back Diana’s hood and give her clit some direct attention. I told Kasey that by pressing her lips around Diana’s clit, she could trap it and lick it to her heart’s content. I then took her hand slipped a finger inside, showing her Diana’s g spot and having her stroke it while she continued sucking on her clit. Growing hard again, I whispered encouragements in Kasey’s ear, telling her what a wonderful job she was doing and calling her a good girl again as Diana came.

Diana then said one of the sexiest things I’ve ever heard come from her mouth, “Your reward for making me cum is getting to watch Daddy fuck me.” Kasey pulled back and I wasted little time in sinking my cock into my partner. Diana gave a guttural moan as I pushed in all the way. I had her legs up against my chest to support me, but I let one drop in favor of holding myself up against the wall as I slammed into her again and again. The bed was shaking and creaking, and Kasey’s face held nothing but pure lust as she watched us. Diana was holding a hand over her mouth as she came, and I followed suit. I got up to clean myself off a bit, and by the time I returned, Kasey had gotten on top of Diana and they were kissing. I helped myself to a sip of beer as I enjoyed the view, but was unable to refrain from joining the fun for too long. I gave Kasey a few slaps to the ass as I parted her cheeks and began licking her from behind. I even let my tongue explore her asshole a little bit, which she seemed to enjoy. Kasey repositioned onto her back and I was eager to make her cum again. With my tongue on her clit and my fingers curling against her g spot, it didn’t take her long to, but this time, she didn’t tense up and get too sensitive. I kept going through her climax and she began squirting on my hand and wrist. Diana asked her if that was the first time she had squirted, and surprise– she didn’t even know she had just done it just then! We showed her the wet spot on the sheets and she said it had never happened before. She was nonplussed until I took her hand and put it above mine as I got her to gush again. With that and having already been fucked by a strapon, that was two things off her bucket list, so she was very happy.

I asked to fuck her again and told her to get on top of Diana as I got a condom. I held her hips and pushed in between her pussy lips as I began fucking her from behind. I went a little bit harder this time, slapping her ass and pulling her hips to meet mine with each thrust as I continued feeling out her limits. Diana was kissing her and masturbating while she grinded against her leg, later telling me she came that way and that Kasey would smile each time I spanked her. I fucked her as long as I could until I came for the third time that night, filling the condom with whatever I had left in me, and holding my cock inside of her for a few delightful moments as I came down from my climax.

As I disposed of the latex, Diana retrieved her wand and began using it with Kasey, holding it between themselves as they kissed and grinded against each other. I fingered Diana from behind, using three fingers to stroke her g spot as the wand did its magic. Diana turned over and I fucked her again, with Kasey right next to Diana and enraptured with our lovemaking. Diana and I kissed as I fucked her as hard as I could, the sounds of our bodies slapping together getting even louder than the music. Diana came, as did I yet again, and we untangled so we could all cuddle side by side. Diana used the bathroom, so Kasey and I continued cuddling and already started talking about how we’d need to do this again. When Diana got back, Kasey surprised both of us with her stamina by asking for the wand. She used it on herself as Diana and I kissed her and stroked her body until she came on last time and turned the wand off. As sexy as that was, things were getting late, so we cuddled only for a few more minutes until Kasey got dressed and Diana walked her out.

We’re already looking forward to next time.

Source: reddit.com/r/gonewildstories/comments/axlqfs/she_wore_a_buttplug_to_our_first_date_mff