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Not only am I more aware of physical mechanics, but I feel more connected with the people I am intimate with. It’s made me a better lover and a better boyfriend to men, women, and genderqueer individuals. It’s naughty.īottoming has now become something that is not only important to my sex life, but to my sense of well-being. It’s a whole different thing when women play with my anus: It’s kinky. But bottoming with a woman, I’ve discovered, is not at all like bottoming with a man. In the years since, I’ve bottomed for plenty of men and women. Oh, boy, did we use toys.Īlthough my relationship with Jenny didn’t last, my love of bottoming did. From then on, we used fingers, she used her mouth, and we used toys. It didn’t take long before I became a big ol’ bottom. When I managed to stop clenching, I finally understood what all the fuss was about. Later, at Jenny’s place, she started fingering me while jerking me off: “Relax,” she whispered. In hindsight, I realized the problem with my little experiment was that I wasn’t turned on. So, I cut my nails the shortest I’ve ever cut them, lubed up my index finger with conditioner, and slowly worked my way up in there while I took a shower - it was, OK-ish. You have to prepare! You can’t immediately expect to take a whole penis inside you without a warmup or knowhow. I realized that’s where I went wrong the first time. I agreed to give it another try, and she told me I needed to practice on myself with fingers and toys. Regardless, I loved Jenny and I would do anything for her, including taking it up my ass. I remember her saying something like, “Honestly, I thought one of the best things about you being bi would be that you liked to bottom.” Honestly, I tend to laugh when people start calling me dirty names, so at first, I had no desire to bottom for her. But unlike me, she was a dominatrix who liked being verbally abusive to straight guys while she pegged them. Besides, lying on my stomach didn’t feed into the powerful, dominant, or masculine persona I had cultivated in the boudoir.īut that all changed when I started dating Jenny.* Like me, Jenny is bisexual. I didn’t let go, but I did decide bottoming was not for me. He kept saying, “Relax,” but I was simply too terrified to really try. I was terrified of making a “mess,” given that was the only sensation I’d previously felt come from my rear end. I was on my stomach the entire time because for whatever reason, I thought it would be the easiest way to start out - FYI, it’s not! So I went through with it, making all the classic first-time bottoming mistakes: I didn’t “clean” prior because I had no idea how, and the whole time he was inside me, I clenched for dear life. He asked early in the relationship if I would bottom, and when I told him I didn’t want to, he never asked again. I also respected him for never being pushy. I felt like a crummy partner for not returning the favor. After a few months, I decided I wanted to bottom for him. That was until I started dating this guy who mostly topped. I didn’t want to deal with any of that awkwardness, so I didn’t bottom for years, even though there were guys begging me to try. Even though I often act more feminine in my everyday life, I liked knowing that I was the “man” in bed.Īnd then (can I be frank here?) I’d heard horror stories from friends about accidentally “letting loose” on a guy they liked. I felt empowered being the one thrusting. I had also begun to embrace my identity as a “top.” Inherent to how I perceived this identity - though I didn’t realize it at the time - was the notion that top equates masculine. I know it might sound absurd - given that I’d seen firsthand the immense pleasure my partners experienced from anal penetration. Even though I had topped a number of guys, I was convinced that bottoming was going to be pure torture. I was terrified of bottoming before I tried it.