I hooked up with this white boy last summer, a computer programmer, shy and quiet demeanor. He was about 5'8", built the way I like - combination of hardness and softness. Big strong shoulders and round, soft middle. Strong as hell thighs that he'd just wrap around me and drive me crazy. A little bit of hair on his body, which I'm also really into.
He really wanted to fuck me in the ass and said as much my 3rd time at his place. We had started making out after watching porn. My recent T shot was making me extra touchy-feely-grindy. When he put my hand on his crotch, I could feel his hard cock through his jeans. We groped on each other, hastily pulling off each others shirts. He flipped me on my stomach, climbed on my back and dry humped the fuck out of me, roughly pushing his cock into ass. And that's when he said it, "I really want to fuck you in the ass. Do you want me to?" Believe me, right then I wanted nothing more than for him to rip off my pants and fuck me so hard, but I...couldn't let him fuck me there. For some reason, the idea of anal sex terrified the hell out of me. Not only did it seem so taboo, given all that I'd been socialized with in my former life as a middle class, demure black girl, but I'm a survivor of sexual violence and anal sex was one thing that, because of the pain, always seemed to trigger memories I didn't care to relive. The same memories that made me scared of sex for so many years, afraid to admit that I had desires. In my former life, I never felt like I owned my body and could derive pleasure from it. Whenever I fucked nontrans guys, who were most often clueless and didn't know or give two shits about how to pleasure a woman's body, memories of the abuse would always resurface and force me to shut down. Transitioning, being on hormones, increased my libido, which forced me to evaluate the role of sex in my life and work towards accepting myself as a sexual being.
Yet, I wasn't completely comfortable with the idea of getting fucked in the ass and I pondered this on train ride home, after leaving his place that night. A couple things quickly became clear. Firstly, I really wanted to try it. Yes, it's not something I feel compelled to do with most guys I slept with, but every once in a while I'd meet a dude and he'd get me so turned on that I'd want him to fuck me there. Secondly, I was of course afraid of the pain; it'd been a looonngg time since I'd had anything up that hole. Thirdly, I was also afraid of things getting messy. I'd heard about people doing an enema beforehand and I thought that was kind of extreme. I understand why though. I certainly didn't want poop to make an appearance while I was fucking. (I know there are folks who are into that. No judgment if you are one of those folks. It's not my thing.) By the time I got home that night, I realized that my biggest sources of fear where anal was concerned were: pain and poop. Okay, I was making some progress. I sought advice from my roommate and did some googling on the "pain and poop" (P&P) dilemma. Unfortunately, my research did nothing to assuage my fears - P&P are just a regular part of anal fucking. The pain fades after the 1st couple entries, depending on: how often you've been fucked, how relaxed you are during said fucking, your partner's girth, etc.. Poop emergence can be minimized by going to the bathroom beforehand and, if you're ultra paranoid about this (as I was), watch what you eat that day. I would stay away from beans or any high fiber foods.
The next time I went to his place I was ready and nervous as hell. Of course, as is my style, I went overboard on the preparation thing (pre-sex bathroom visits, showered, watched what I ate, etc.) We'd discussed things prior to my coming over. I was going to give up the ass, but it'd been a while and he knew this, so he was going to go slowly and be gentle. Later that night, I'm on my stomach on his bed as he stood over me, condoming and lubing his dick. He stroked himself, eyes trained on my bare ass. I in turn gazed at his hard, reddened cock, getting hornier by the sight of it. He climbed onto the bed, making his way towards me, cock bobbing in the air. "Lay on your stomach like that. It'll be easier..." I nodded. He lubed his finger and slowly entered me. I tensed for a split second. It felt...like I was about to take a dump or something. "Relax," he whispered into my ear and, maybe it was the way he whispered or his breath tickling my ear, somehow I relaxed. He gave me more of his finger, maintaining a slow rhythm. The initial discomfort subsided and it started to feel really good. My ass may have started to move in response. "You like that?" again the seductive whispering. I reached around and grabbed his hand, making him go faster and deeper. Eventually, he was on top of me, cock slowly slipping in and wow! After the head of his cock slipped in all the way, I had to stop him and give my ass time to adapt. "Do you want me to take it out?" he asked and I shook my head. The pain was really something else. However, I could sense a delicious fullness just beneath the pain. I could feel his warm, hard-yet-soft body on mine, his legs on either side of my legs, and his groin mashed into my ass. It was all so erotic and I just wanted him to go buck wild screwing me silly. I knew though, given my somewhat anal virginal status, buck wild ass fucking wasn't in the cards for me just yet. So while we waited for me to grow accustomed to the sensation, he planted soft wet kisses on my shoulder and neck, nibbled on my ear lobe, whispered how much he'd been jerking off imaging this. A mental image flashed in my mind. I saw him lying in bed, hand clasping cock, rubbing furiously. That did it. I moved my ass so he could give me more and he slowly pushed into me.
Much later, I discovered he was a pounder - the kind that gets into a zone, fucking like he's purging himself clean. I also discovered that having someone jerk on my clit while plunging in and out of my ass is easily the most wonderful thing in the world, next to coconut ice cream. More importantly, I learned that I could enjoy taking it as much as giving it, and it didn't have to be laced with bad memories or all around bad vibes. I still don't do anal (as a bottom anyway) with most of the guys I play with. For reasons I haven't analyzed yet, certain dudes just bring it out in me.