My first time alone with Wing [MF]

After a few weeks, May and I had been together a few times, and I’d had another threesome with Wing and May. Typically I’d be with May twice a week, normally Thursdays and Saturdays depending on her schedule.

One Tuesday evening I was again in my room, this time working, and Wing just walked right in and locked the door. She’d been in the shower and was wearing a fluffy dressing gown and had half dried hair. In her hands were a dildo and a tub of vaseline. She was a woman on a mission. My first thought was, you’re not sticking that thing up my ass! Almost right away she opened and dropped her gown to reveal her complete nakedness. I of course stood up to greet her, and she came right over and started to remove my shorts. She was freshly shaven, normally Wing and May were quite naturally hairy, but Wing had really gone to town with the wax and was looking trim.

I was getting hard now with excitement, this was my first time alone with Wing, and she was sexy as hell, aggressive and knew what she wanted. We were now both naked and on the bed making out. After a short while, she worked her ass up to my face and her head down to my cock. When she straddled my head I caught a flash of bright pink and saw my first ever butt plug. Being the innocent I was, anal play was very new to me, and I wasn’t 100% sure what it was, but it looked fucking good. I started to eat her out, my nose pressing against her plug. I played with it a little, twisting, just getting a feel for it, which she really seemed to enjoy. She had quite large, dark labia, which I just loved to munch on.

She was sucking me off so well, her head bobbing up and down, and using her hand expertly. Once again, too quickly for my liking, I was about to come. Without warning I exploded into her mouth, at which point, really quickly, she flipped herself round and just sat on my twitching dick, taking my full length up her sopping pussy. It felt sooo good to plunge deep inside her while ending my ejaculation.

But Wing wasn’t done. She started to grind on me, softly at first, but then got into her rhythm. Her big tits were swinging in circles above me, and I lifted my hands to allow her nipples to glide over my palms. After a little while I just pulled her in and buried my face in her tits. Overcome with lust, and the sensation of her pussy, I began to reach peak hardness again, and it would take a while for me to cum this time, which was nice for a change. It was like Wing knew how to keep me hard for round two.

Once Wing felt my hardness return, she got off me, picked up the Vaseline and dildo, took a huge glob of it and worked it into my dick, she then took me off the bed and got onto all fours, working her butt plug out and planting her face on the bed. She said in a commanding way, “fuck me in ass”.

I had not done this before and wasn’t 100% how to go about it, so I just went for it. I knew enough that it would be tight, and I should be gentle, but her asshole was fairly wide from the plug, and she seemed to know what she wanted. I slowly pressed my tip into her, and allowed her to control the speed and depth, she very slowly worked me in, taking her time and letting out almost painful moans and squeals. God it was so tight, and I seemed so big compared to her! Once I was up to my hilt she looked so spread out, I was massaging her bum, so soft and gorgeous. She started to work up a rhythm that increased with speed and depth. At this point she got out her dildo and just rammed it up her pussy and started working that too.

She was timing it so when I pulled out she would pull out with her dildo, and when I went deep, she went deep, I think she liked the feeling of being stuffed, and we worked up a good system. I know I liked the feeling of being up her bum. It was such a different sensation, much much tighter, and having just cum, I could really just be in the moment of penetration, and it was magnificent.

She definitely had at least one orgasm, and just kept pounding herself and getting pounded by me. Her moans and the pornographic sight before me started to push me over the edge, and I could feel my dick beginning to build to orgasm. I grabbed tight hold of her hips and started to do big, deep, methodical thrusts, wanting to really feel this orgasm fully. After a few of these I told her as best as I could I was going to cum, and she started to writhe around on my dick, at which point I exploded inside her.

I was just looking at my twitching cock, deep inside this woman’s bum hole, and loved the dirtiness and the sluttiness of it all. Once I’d cum, I went flaccid fairly quickly, and pulled slowly out of her, which was a really nice sensation. Honestly, my dick was a little dirty, but what do you expect. Wing was completely spent and just fell on my bed with her dildo still up her. She had a tired smile on her and gave me a cheeky wink.

After a minute or two, I wasn’t sure what to do now. May and I would normally cuddle, but I got the vibe from Wing that she had got what she wanted and was done, as she was getting her things together and pulling her robe on. Looking back I’m pretty sure her plan the whole time was to get me to cum early, then get me hard again so I could be her second, but human, dildo. Fair enough. She did kiss me and thank me, but made no future promises. Although we did hook up alone a couple more times after that.

It would have felt like I was cheating on May, but because of the threesomes, and the relationship the two girls had, I knew it was fine with May and me.

I needed to clean my dick, so I walked out with her, towel round my waist, to get a shower.

Source: reddit.com/r/gonewildstories/comments/iqol5n/my_first_time_alone_with_wing_mf