[MT] A little bit of reckless, but a lot of hot.

I had seen her a couple of times before.

The first time was pretty awkward for me. Pretty inexperienced in the ways around a transwoman, I just jumped in. Little bit of this, little bit of that. It was an enjoyable experience, but my shyness meant it was a quick experience.

The second time was better. I was a little more at ease, a little more sure of myself. The flow of it all was much better as there was less “figuring” it out. Our bodies flowed together and there was no hesitation or awkwardness from me.

This is the story of the third time. I was at her place, and I brought a bottle of some red wine. She cooked, and fed me until I was absolutely stuffed. Had to beg her to stop feeding me. The night progressed as we sipped on the wine, having a great conversation about life and all the things that go along with that. But wine goes pretty quick if you are not paying attention. We polished off one bottle before we knew it, and had opened another she had sitting around. The conversation was enthralling to me. She felt like a life guru, teaching me how to laugh and love and live life like I had never done it before.

The second bottle was gone in quick order, and we were both feeling tipsy. She made some warm lemon and honey water as it was late, and I sipped on as we started to make googly eyes at each other. Love was in the air as we started to intersperse our conversation with some pretty nice kissing. The kissing was effortless. Lips and tongues were in the perfect position and we didn’t have to fight each other. My hands caressed her face as we subtly moaned over the kisses.

The action moves to the bedroom as I continue to make out with her. I unbuckle her pants and take them off. She’s wearing this tank top bodysuit (think like a one piece swimsuit) that just shows an amazing amount of cleavage that had been driving me wild all night. I unsnap the bottom, only to find her wearing a high-waisted pair of silky smooth panties underneath. I groan a bit in frustration, like a child whose parents wrapped their Christmas present in one too many layers.

She pushes me down to lay on the bed, and maybe it was the wine, but I swear my pants were off before I hit the bed. And already rock hard from the kissing and teasing, my cock bounces to life as she pulls my underwear off. The stroking, the licking, the sucking is as incredibly as I remembered. She eagerly deep throats me, gagging a bit as she goes.

I guide her to lay back as I continue to take her bodysuit and underwear off. She’s laying on her back as I’m draped on her side. Our cocks are touching as I use our precum to stroke and tease us together in one hand. She throws her head back and moans as my hand explores her, our cocks twitching together and making sparks as they touched. No longer able to resist, I get in between her legs as I begin to suck her. I get slobber all over the place as I drool all over her.

She groans in frustration as I stop. I sit up on my knees, and the position I’m in puts the tip of my cock just lightly pressing against her sweet spot. I tease her, pushing just a little to put some pressure on her hole. As I’m stroking her, my saliva begins to dry a bit. I spit on her cock to moisten it up a bit and continue to tease her hole. And here comes the reckless part.

Both previous times, we had been pretty careful to use condoms. Not just for safety reasons, but for cleanliness ones as well. So as she reached for her bag, I expected a condom. But in a flash, she was lubing my bare cock and guiding it to her ass. My brain said, “But what about the condom”, but my dick quickly said, “Bro, don’t ruin this for us.”

And there I was, bareback and deep inside her. She arched her back and let out a sharp moan as I first entered, but she quickly settled into the groove. My pace was quick, but passionate. My thrusts were long and slow. Missionary with her was the most lustful thing I’ve done as I looked into her eyes.

I grabbed her by the back of her neck and pulled her up as I laid back in a swift move. She was now on top of me, all while still being inside her. She flicked her long, black hair out of the way as she began to grind on me. The feeling of my cock filling her ass was getting to her. She started moaning “Ohhhh right there” repeatedly as I began to hit the right spots. She started to slow.

“Oh baby, you are going to make me cum already,” she stated. I told her to give it to me and cum. She pulled a bit of extra lube from my cock and began stroking herself as she grinded me. She closed her eyes, tensed up her ass, and let her cum fly all over my stomach and chest. Rope after rope, and yet she didn’t slow her pace as she came.

I told her to get up and had her lay on her stomach. I climbed on top of her, and slid into her. She tensed a bit again upon the initial shock, but quickly settled. I started slow, but I couldn’t help myself. The sight of her ass as I was fully inside her overwhelmed me, and my pace began to quicken. The angle must have been hitting her the right way, as she was cumming again in short order.

I knew I was close, and I knew I wanted to look her in the eyes. I had her flip on her back again so I could fuck her missionary again. She raised her legs up more to let me in even deeper, and I could tell I was past the point of no return. So could she, as she grabbed my head and kissed me as I came deep inside her in one of the most passionate orgasms I’ve probably had.

Cut scene to us both being cleaned up and lying naked in bed. I started spooning her, but throughout the night, we would flip over so she could spoon me. And let me tell you, it was the most amazing feeling having her pressed against my back. Maybe it’s because she was closer to my size than most people I’ve been with (she’s 5’10” to my 6’0″), but I slept like a baby in her arms. Something I’ve never been able to do with anyone else before. Or since.

So yeah, that was the time I raw-dogged a transwoman. Definitely number one in my spank-bank.

Source: reddit.com/r/gonewildstories/comments/a8pcc3/mt_a_little_bit_of_reckless_but_a_lot_of_hot