The New Top
In the early days of pandemic dating, across hazy Discord videos joining separate rooms miles apart, a woman I had only met once asked me a question while hiding behind a disarming, unsure smile:
“What about…pegging?”
The floodgates were opened. We had talked openly and honestly about sexuality, desire, and what worked for us before over cascading texts, but this was the first time we were talking about specific fantasies. Her fantasies. Something she had never asked any boy before, let alone one she had just met.
As we deepened our friendship over the course of the next few weeks and months, kept chaste by the pandemic that insisted we spend hours talking about what we wanted instead of rushing to act them out, pegging had become something of a goal for us. We purchased a harness and dildo, knowing full well that it would take some time before we could use them. As fun as it would be, the reality was I had only ever received anal with a strapon once at a workshop.
I remembered it as a fine experience, but it didn’t really feel like I imagined. I couldn’t shake the urge to defecate. My body was doing what it did best – rejecting any new foreign insertions. I couldn’t relax enough to let it in comfortably. Yet, I got a sense for what it could be like if I kept working at it. Doing some research told me this feeling was normal, and eventually I’d be able to relax and enjoy it.
Armed with this information, and now able to be with each other in safe, intimate ways, we took our time. We started with a single finger, slow, well lubed. I tried to breathe and relax as she entered me. It was intense, and once she had found out how to stimulate the prostate, I could hardly catch my breath. The sensations were overwhelming, new, immensely pleasurable, and my body was rejecting it. The head of my penis somehow felt like it was throbbing from being touched on the inside while I struggled with the feeling that I was about to shit.
She had a blast.
I was determined to make it work. We tried again over the course of a few days and weeks. One finger, slow, well lubed. We introduced a butt plug to try and loosen me up during foreplay, then when she entered me with her finger pointed out how much looser I was. This was progress.
60-40
Eventually, I asked her if we could try the strapon.
“Are you sure you’re ready for that?” she asked. I said yes, knowing that although I suspected I wouldn’t wholly enjoy it, I knew I’d have to try it eventually to make progress. Besides, I had taken a strapon once before, so I knew my ass was capable of receiving it.
“I’d say 60-40,” I told her after we were done. I enjoyed it 60 percent of the time, I was uncomfortable 40 percent of the time. I wasn’t in pain, mind you. It was just that damned feeling that I needed to get the strapon out of my ass in order to relax and be comfortable. On top of it all was the intense prostate stimulation. Was there such a thing as too much pleasure?
Time moved on, and we continued to practice as we deepened our love for each other. We talked about how being with each other made us immensely happy. We talked about how we could do anything together. We talked about never truly being in love before.
The numbers began to move. 70-30.
We had difficult conversations about what it meant to let another person into your life. How sharing this deep of a relationship with someone was new. How sometimes you need space, and sometimes you don’t. How I’d never done this before, how I was working out how to let someone into my life, how for twenty-seven years, I hadn’t had to share myself with anyone, and that was new and foreign to me.
80-20
Realizing that in being with each other, we hadn’t lost an inch of our former selves. Realizing that the time apart let us regather ourselves and be more present when we’re together. Realizing that we were two whole people that enhanced each other. Realizing that we loved each other deeply, and wouldn’t change a thing even if we never had sex again. Realizing that we’re better off together.
The Completed Circuit
A single finger, well lubed, slowly.
“Is it in?” I asked, on all fours, my ass wet with lube.
“Yeah, it’s all the way in.”
I had barely noticed. I took her finger without flinching. She began working my ass, her ass, slowly. I felt naked and vulnerable and good. My body didn’t reject it, it wanted her inside me. She moved to two fingers, and that intensity came back, like how one finger felt way at the beginning. Another goal to work towards.
Feeling I was warmed up enough, I heard her snap a condom onto her dildo, the sound of lube dribbling out of the bottle, then fresh coolness dripping down the crack of my ass as I took a deep breath and settled in. Crouched behind me, she found my hole and pushed. The silicone slid inside me with ease and without protest from my anus. Deep, solid, and entirely hers – it felt like it belonged there. She began thrusting.
The strapon slid in and out smoothly and I moaned. She increased the intensity. I couldn’t believe how completely fine I felt, how comfortable and relaxed I was. I was getting fucked. Well and truly fucked. I took a sideways glance at the mirror.
“Do you like looking at me fucking you?” she asked.
I did. Oh, how I did. Poised above me, hips thrusting with confidence and authority, her hair wild and free, fucking her boy in her bed with her dick. She was awe inspiring. I felt happy, I felt owned, I felt loved.
She reached down and grabbed my dick. Feeling it throb and pulse in her hand reminded me it was even there. An electric shock went through me. She had completed a circuit. Suddenly, I wasn’t just getting fucked in the ass. It was a complete feeling of wholeness I had never experienced before. This is what I imagined getting fucked in the ass felt like. Vulnerability, and ownership, and completion. I slipped into sub space, gave in, and submitted myself to her, sliding onto my belly so she could envelop me, drilling me into the bed, grabbing my collar, my hair, telling me how good I looked as her well fucked boy.
Satisfied with one position, she flipped me on my back. The strapon was reinserted with a fresh cool wave of lube and it went in again, with ease, swallowing it up. She thrusted against me, looking down at me, hair splayed across her face, teasing her deep brown eyes that drank me in. I shifted position so she could get to me easier, wrapping my legs around her, wanting her closer, in me, over me, kissing me, warm wet lips to close the circuit of our bodies. Two wholes, made better together.
She grabbed my dick again and began jerking me off. The wires were live. I could have stayed there forever, under her, owned by her. I asked if I could come, and she granted permission.
An earthquake in my body. Shuddering underneath her as she continued to fuck me. I didn’t even feel the usual orgasmic pleasure at my dick. I didn’t even know I had a dick anymore. My legs convulsed, my body heaved, come appeared on my chest. Like a receding tide still crashing in waves, the orgasm subsided.
She slid out and smiled at me and laughed as I looked up at her in disbelief at what we had done together.
“95-5,” I told her, and we collapsed into a messy puddle, drunk on our shared love for each other.
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