I believe I met this guy off of..doublelist? I don’t have it anymore because I wasn’t slick with it 😝
Anyway, pegging had been interesting me for a while. I think it’s the power exchange, the flip of tables. I’m not exactly a top and don’t consider myself one but every now and then I wouldn’t mind pulling a tight ass against my strap.
He was a couple years older than me but I liked that he was caring and respectful even without knowing me. He worked two jobs to pay for his Uni classes but found the time to tell me about how he’d be honored to be first pick as it would be his first time too. We exchanged pics and I discovered he was a slimmer guy. A thin and pale nerd with a totally doable dirty fantasy.
Within the first week he’d been calling me Mistress. He’d let me tell him what to do, when to do it. I got many appreciated cumtributes and left him without release multiple other times, wanting him to be the most desperate for when I met up with him. Poor boy was so needy he gave me his address and let me come in and blind fold him. Yes, exactly. The idiot’s never seen my face, as he wanted to wait until he deserved to see me. But he let me in his place with his back to the door and I had him slip on a cover alike a black eye mask.
We made small conversation while I stripped down. He had bought me a strap on set kit and I nervously struggled through the straps tightening wherever it needed to be tightened while he talked with me. I then gave him a pat on his thighs and told him on all fours. He did what I said and let me lube up his ass with a couple fingers. At the same time I let my hand repeatedly graze over his member from underneath and watched it react to my touch.
I played with him there a bit more but eventually had the tip of my dildo in his ass slowly easing it into him. At a later point his head had started banging not so lightly against the wall with each thrust as we were on his couch, but he didn’t seem to mind and I would readjust him when I could. I kinda felt for his neighbors cause he was loud, enjoying himself.
Unfortunately I didn’t have all the time I wanted and had to cut it short. I don’t know if he came but the good boy was panting, seemingly happy when I called him a good boy and rubbed his cheeks. He was basically vibrating. While I was pulling my clothes back on rushing out the door, he called out pretty loudly, his voice still unsteady “Will you be coming back Mistress??”
We haven’t met up after that time again yet, but we’re still in contact and I hope he’s still being a good boy ^^
Source: reddit.com/r/gonewildstories/comments/11l73gz/first_time_pegging_a_good_boy