I posted a few weeks back about several experiences I’d had, largely around humiliation, feminization, and cuckoldry. I guess with quarantine and everything I’ve been extremely horny. Someone suggested I try Grindr, and in a moment of particular horniness, I did. The user had some advice for prof info and settings. He suggested I list myself as a twink, and put that I was a sub who enjoyed being humiliated and feminized.
I had never used or even seriously considered Grindr before, and there was a lot of really weird stuff and people, but I had a few really sexy conversations after a bit of experimenting.
One guy, I’ll call him John, was hot and commanding from the beginning, but not in a forceful way. He sent me some pics of himself lying in bed. He’s 36, dirty blond hair, with heavy stubble, and a broad jaw. He was shirtless in his pics, and he casually started telling me about the things I secretly really wanted.
His messages turned me on a lot, and he had my fantasies and desires nailed. We started chatting more, and we both shared more about our experiences and eventually verified ourselves, and moved to text. We continued having this flirtation for several days, when he started giving me orders and assignments. It started small, and escalated. He showed me how to shave my body hair (I have relatively little anyway), and he ordered a bunch of sex toys and lingerie to my apartment. I started playing with my ass, which took a long time to get used to and stretch.
I wasn’t allowed to cum unless he gave me permission. He would have me edge for several days, and then make me cum to something totally humiliating, and always when my ass is being filled. I haven’t cum without my ass being stimulated in weeks. He’s very into conditioning, and there’s a word he uses for when I can cum. Now just thinking about that word makes me horny and a little humiliated. When I finally have an orgasm, it’s so intense.
We got into a rhythm where every morning I’d send him pictures of my body, sometimes in these panties, and sometimes just naked. He likes to be called Sir. He gave me a female name, Lily, and started referring to me as female all the time, and referring to my penis as a clit, etc. I also started confessing more and more of my fantasies and desires to him. Our correspondence became this super intense whirlwind. I was horny and aroused and in need almost all the time. There were moments when I wasn’t horny and I would get a bit freaked out and stop feeling the same arousal. I didn’t feel about John the way I feel about a beautiful woman, and I had never intended to go this deep into these fantasies. I thought about texting him to call it off, but every time I considered it, I chickened out and then got horny the next day and wanted more.
I have always considered myself at least bicurious, and before this, the arousal I felt about other men was always wrapped up in feelings of inadequacy and humiliation, and in the context of their ability to please women. But with John, there was no other woman involved at all. So at least when I was into it, I was definitely experiencing unambiguous attraction to another man.
After a while, we started discussing the possibility of the two of us forming a pod. We’re both living alone, and after discussing it for a bit, and during a moment of intense horniness, I agreed.
On Friday afternoon, he texted me that he wanted me to come over and serve him that night. It’s gotten to the point where just getting a text from him makes my heart race a little. I told him I’d come over. He told me to shave and to wear this one pair of panties he really likes under my clothes. I was so horny and excited I was shaking, so I shaved very slowly. When I was finally all smooth, I rubbed lotion all over my body as he’d taught me, put on the panties, and put on shorts and a t-shirt.
He picked me up, and drove me over.
Tbh, when I first saw him and his car, I totally panicked because I realized how far in I was. At that moment, I lost all interest and wanted to back out. But I was nervous and meek and went along. I got in the passenger seat, and my heart was racing. He was as rugged as his photos suggested, but a little older looking. His arms were muscular, and he had a little bit of a beer belly. So his photos looked maybe 7 years old?
We started making awkward small talk as he drove me to his place. After a few minutes, he placed his hand on my crotch, and started rubbing through my shorts. I got hard pretty quickly, and he started telling me what a good slut girl I am. By the time we got to his place, I was really turned on again. He lives in an apartment building, and he led me to his apartment with his hand on my lower back, slipped under my t-shirt, which was surprisingly humiliating and arousing. I was struggling to cover my erection.
When we got to his apartment, we walked in, and he bent down, put an arm behind my knees, and picked me up. I instinctively wrapped my arms tightly around his neck as he comfortably carried me to his bed, and threw me down. And this point, I was nervous but also incredibly aroused.
“What’s your name, girl?” He growled, as he undressed and took off my clothes. “I’m Lily,” I moaned. At this point, I stopped feeling self-conscious and just got lost in the role.
He climbed on top of me and grabbed both of our dicks, pressed against each other. His was almost twice my length.
“Are you a guy?” He asked. I told him I wasn’t. He asked me what I am.
“I’m just a pathetic little bitch girl,” I moaned.
He told me to kiss him, and I did. It was surprisingly good, and he wasn’t aggressive with tongue. We fell into a rhythm with me grinding against his body and his hands roaming mine. After a few minutes, he got up and put on a condom and started lubing it. I was high on arousal by this point. He offered me poppers, which I accepted. I had never done them before, but I did as he started pressing into me.
It had this dull ache, and then felt so stretched. It felt satisfying as he entered, in a painful way. He pulled out, and slowly entered in again. This went on for a while, and he started slowly speeding up. It still hurt, but started feeling really good, too. He was so strong and so much bigger than me. I felt completely overwhelmed, in every way, just a hole taking this magnificent man’s cock, and enjoying it. He told me after I was moaning loudly, but I didn’t notice. It both felt like my body was breaking in a way that felt wrong, but it also felt like scratching this deep itch that was so satisfying. This went on for what felt like eternity, and he started grunting and came inside the condom. I felt his cock throb inside me, which was so sexy. He pulled out, took off his condom, and lay next to me, recovering. I felt such a deep rush of need, and I started kissing him and rubbing against him. I just wanted to feel him holding and touching me and telling me I’m good. We stayed cuddling like that for a bit and then he started holding and kissing me again. He played with my clit, until I came, looking up into his eyes. It was so intense.
We kissed for a while, and then we got dressed. He ordered us takeout, and afterward I ended up sitting on his lap kissing his neck and feeling his muscles.
Eventually, he drove me home. I was a combination of exhausted, sore, horny, excited, emotional, nervous, a tiny bit regretful, but also incredibly glad and satisfied. I was slightly trembling the entire ride back home.
The next few days, I basically stayed indoors masturbating reliving the experience, and crying. It was further than I had ever planned to go, and it made me nervous that I enjoyed it so much. John and I have chatted a bit since and I’m not sure if I want to hook up again. On one hand, it was the most satisfying and a rousing sexual encounter of my life. On the other hand, I’m scared of how much I’m drawn to him, and of where I’ll go if I keep indulging these fantasies and desires.
Source: reddit.com/r/gonewildstories/comments/kbcg20/my_first_sexual_encounter_with_another_guy_mm
If anal is painful, you’re doing it wrong.