Since Roid Douche, anal sex was off the table. I couldn’t bring myself to be comfortable with the idea of letting any guy penetrate my ass again. It took a lot of time and trust for me to even allow any light anal play from my next serious boyfriend, The Man Child (who I dated for six years). In those six years, he asked about anal from time to time because it was something he wanted to try with me, and I kept turning him down. He’d ask why I didn’t want to try it, I explained I’ve tried it before with Roid Douche, but didn’t like it. I didn’t inform him of the rape at that time.
Over the first few years of dating, as The Man Child tried to ease me into the idea by incorporating light anal play from time to time into our sex, he brought it up again, asking if anal sex would ever be on the table. I then explained what had happened with Roid Douche. We had a lengthy conversation that involved me crying about it, him consoling me, and him saying that he’d kick Roid Douche’s ass if he ever came across him. He also threw out there that if anal sex was ever something I would want to try again, he’d obviously be down, but understood why I haven’t wanted to all these years so far.
The Man Child stopped asking about anal since I told him about what happened with Roid Douche, but he still tried to incorporate anal play in our sex. I knew he was secretly hoping he could get me interested in anal. I enjoyed a finger and some ass eating every once in a while, but I was unsure if I was capable of enjoying a cock. I was conflicted. I felt some sort of pleasure from the stimulation of anal play, but I got anxiety thinking about anal sex. I wanted to try it again, but I also didn’t want to relive my experience.
Eventually, probably about four years into dating The Man Child, almost five years after the Roid Douche incident, I told The Man Child I wanted to try anal. He was ecstatic. He did everything right. He incorporated lots of foreplay and oral and warmed me up for anal with some analingus and fingering my ass. He got the lube out and prepped my ass and his dick. He told me he’d go extra slow and all I needed to do was relax.
He got his dick in about an inch and my anxiety kicked in, I started to clench my ass and it started to hurt, and I freaked out, and told him to stop. I teared up and shut down. The Man Child was a bit frustrated, but understanding of the circumstances. He held me, and comforted me, and tried to ease my anxieties. We tried one more time since then, but same thing happened. I couldn’t go through with it and he was ok with not trying anal ever again.
After I broke up with The Man Child, almost three years ago now, I have slept with a lot of guys. Many guys have asked about anal, I tell them it’s not happening because I’ve tried and don’t like it. Every once in a while, a guy will slip a finger in or try to lick my ass and if I show any amount of enjoyment, they push for anal sex. I refrained from telling them what had happened with Roid Douche, but I explain to them that licking and fingering an ass is completely different than having a dick fuck your ass. I say something like, “A finger is much smaller than your dick, I’m ok with and enjoy a finger from time to time, but a dick is a no go. I’ve tried it and don’t like it.” And some of them push it and some of them let it go, but I stayed consistent with my word and wasn’t trying it again.
About a year ago, there was a moment of pure bliss I felt when a guy was eating my pussy and fingering my ass and vagina at the same time. The orgasm was intense and I wanted to recreate that feeling. I bought a small vibe for my ass, not much thicker than a finger, and began incorporating that into my masturbation. Shortly after that, I bought some gradual anal beads, the largest bead was about two fingers thick, and played with those by myself and introduced them with some guys to add to our toy fun.
And then Neighbor Boy came along. He had a good amount of persistence when discussing what is okay under our terms of sexual agreement. He’d push for cumming in my mouth and no condom use, both no goes. He pushed for photos and video, shot down. He pushed for anal, I turned him down. I explained to him that a lot of those things are not for guys I’m just fucking. I have to trust someone before I allow for them to cum in my mouth or go condomless, get photos or video, or before we could even put anal on the table. He then asked how he could build that trust with me. I told him it would take time, communication, and also an eagerness to please me extra in the bedroom.
In those early months of our arrangement, we talked most days and had lengthy conversations about sex, our likes and dislikes, our experiences, our desires, and we communicated when we’re sleeping with other people. We were 100% honest and upfront to one another. He made it a point every time we fucked to try to make sure I was pleased with our sex and we would have discussions usually the day after about it, he’d ask what I enjoyed about it and if there was anything he could have done differently. He took my directions and our sex kept getting better and better.
Over those months, he worked for it. He was eager to build that trust with me so he could get to cum in my mouth, get photos and video, and get anal sex. He was doing a pretty damn good job at it too. The more eager he was to please me and the more effort he put in, the more eager I was to please back. I let him cum in my mouth; something very few guys get to do because I have an aversion to cum. I sent him photos from time to time; I don’t send nudes to most guys, another Roid Douche story behind that one. And then anal… well he still wasn’t getting anal.
We discussed anal sex time and time again, and I told him I’ve tried forever ago but wasn’t into it, but I didn’t tell him about Roid Douche. He then brought up the anal beads and how I like those, and I explained that those are still smaller than a cock, so it wasn’t quite the same still. He kept telling me how he’d make sure I was enjoying it, and I wanted to try, but I still had this intense hesitation.
That’s when I decided to order a large Njoy butt plug. Larger circumference than the anal beads, but still smaller than his dick girth, it would be a good stepping stone to add to our sex to get me more at ease with anal. When it arrived, I kind of got giddy. It was a new toy to play with and I was excited to try it out. Neighbor Boy and I were already planning on hanging out that evening, so I told him I had a surprise for him. When he came up that evening, I unboxed the shiny new toy. I was turned on just by the idea of trying it out.
Keeping it bed side, he got me warmed up. We made out, he worked his way down my neck to my nipples, to my clit with his tongue. He ate me a good while and got my vibe out, getting me extra worked up, and when I was nice and soaking wet, he grabbed the plug. Lubing it up, he inserted it slowly into my ass. A slight tinge of pain hit me, but after the head was inserted, it was all pleasure. He went back to eating me and playing with the butt plug.
I was really enjoying the feeling of the butt plug, but at the same time, I kept getting in my head too much. The pleasure was great, but it was difficult to fully let loose. I repositioned myself and he presented me with his throbbing cock. I took it in my mouth and blew him while I held a vibe to my clit and he played with the butt plug. The vibe and plug sensation while simultaneously blowing him got me extra hot. Soon enough, I was cumming from the combination and trying to keep his dick in my mouth as my body unleashed an intense simultaneous anal/clit orgasm.
Shortly after I came, he grabbed a condom and began to fuck me, butt plug still in. I was double filled and loving it, but it was almost too much. I was still fresh from the recent orgasm and now the butt plug was becoming uncomfortable. Not long of this and I had him stop so I could remove the plug, and got back to fucking.
The next morning, he asked about my thoughts on the butt plug and what I liked and disliked about it. He wanted to know what was working and not working so he could take that into consideration moving forward. I like that about him, he actually asks questions and makes sure what he’s doing is good for me. He doesn’t assume that everything he’s doing works, he wants to learn about what gets me going and wants to make sure I’m enjoying myself.
Since then, Neighbor Boy, although he has been insistent on using the butt plug from time to time to warm me up to anal, didn’t push anal sex any more. He knew that in time, if I wanted anal, I would make it happen. As I told him, baby steps to ease me into it and to build trust and eventually anal might be possible.
Trust, communication, and an eagerness to please are all important elements in any relationship.
*** Note: in case you’re wondering timeline, I got the Njoy butt plug about 10 days before I got my Triangle Piercing, so sex and oral were still ok.