It started as a joke. Me and my girlfriend, Holly, were joking around while watching a movie and it all somehow went to the talk about anal sex. We started to discuss how it’s many men’s fantasies and that it’s something that’s not pleasurable for women and that was when Holly said the words that got stuck with me.
“You know, men are actually the ones that should love it,” she said smiling and looking at me.
“You are the one with a thing in your ass that should make it feel good”
I thought about it for a moment, staying silent.
“We can try it if you want. Don’t be shy,” she nudged me, seeing how distant I became.
We laughed it out, but the truth was, I kept thinking about it. I don’t know what it was, I never even imagined something like that before. It seemed like something weird and something that I didn’t have to want, but still, it stuck with me.
I started to do some research. Of course, I started with the videos. I didn’t expect to see so many of them with the men being humiliated before they got pegged and enjoying it. I wondered if Holly could do something like that with me but instantly got that thought out of my head.
Every so often I would get back to my research. I still didn’t feel comfortable enough to share my fantasies with Holly, but I knew that she would be open about it. We tried many things together and I knew she was waiting for the opportunity to have more experiences.
“So, about that thing,” I started one evening. “Do you actually think men enjoy the butt stuff?”
Holly laughed, knowing where this was going.
“You want to try it, don’t you?” she asked, looking at me with a wide smile.
“Maybe I do,” I said, still feeling nervous. “But I don’t even know where to start”
“I know. And I have a few things on my mind you might want to try first”
At that moment I knew that we would be having a long way to me actually getting pegged. Holly knew that there was no way for me to take the strap-on without any training beforehand and so we slowly started exploring.
On the first night of my training, we started as we usually did, with us kissing and messing around with each other, until Holly ordered me to take my pants off and get on my fours. I felt vulnerable but excited.
“Someone is really happy that we’re going to play with your asshole,” she smiled at me, as she put her hands on my ass and caressed me lightly. “Let’s see how much you can take”
She got lube from the nightstand. She opened it and dropped some on my asshole, making me uncomfortable with how cold it felt. Holly smiled.
“Don’t worry, I’ll make it feel good”
She took my cock in her hands and started stroking me lightly, with her finger started probing my asshole. I groaned, feeling how tight it was, barely accepting the tip of her finger inside, while she moved it around, giving me a funny feeling that I couldn’t describe.
“Can you take more?” Holly asked gently, stroking me a little faster. “I bet you’d look even better with two of my fingers inside”
I groaned again, feeling my asshole taking more. It felt even tighter around her digits and I couldn’t even imagine how someone could take a whole strap inside. Holly decided that it was enough for a first try, so instead of giving me more of her fingers, she kept stroking my cock, while fucking me with her fingers.
“You like it when I take your asshole?” Holly asked, clearly enjoying the picture.
“Yes,” I said, my voice shaking.
“Then let me finish you off”
Holly went faster and faster, making me feel as good as I had never done before. I couldn’t imagine that it would be like that, but now, with her fingers deep inside me, it only took a few moments for me to cum right on her hands.
We kept doing it more and more often, with me getting more and more enthusiastic. I still wasn’t ready for more, but taking four of Holly’s fingers in was an easy task now. I thought that we will keep going like that, until one evening, instead of just lube, Holly pulled out anal beads too.
I looked at her with my eyes wide, not sure how to feel.
“You think I can take it?” I asked, feeling nervous.
“Yes, you can,” Holly smiled, putting the beads close to my face. “Take one in”
I accepted it in my mouth, sucking on one of the beads lightly and making it wet. Holly clearly enjoyed it and soon she pulled it out.
“Now get your ass ready”
Once again, my asshole was lubed and ready for Holly. She put the beads against my asshole and I felt that amazing sensation of it being spread out and filled. I moaned, as one of the balls was going through my hole and stayed inside, just for Holly to push another one in.
“You can take it,” she said, stroking my cock lightly, to make it all feel better. “You trained enough to make it happen”
I just grabbed the sheets, allowing her to do it, while I was moaning from an unfamiliar sensation. Her fingers didn’t go as deep as the beads did and they weren’t spreading me so deep inside before. My cock was rock hard from that stimulation and I was starting to understand why other men like it.
I thought it felt good when Holly filled my ass with the beads, but it started to feel even better once she was pulling them out, leaving me wanting them again. With her hand on my cock, I finished quickly again, feeling like I would give up anything for her to do it again.
She kept training me, not leaving my asshole for even one day. If she wasn’t stretching me herself she was telling me to wear a butt plug. It was unfamiliar too, having to go all day with that thing in my ass, but with time I learned that it can feel good too.
Finally, the day had come. Tonight I was going to get a strap in my ass. Holly was excited and playful, so before we did it she got on her knees and sucked me off, telling me how amazing it would be to finally fuck my asshole. I didn’t feel embarrassed now, I knew that she wanted it and was willing to give it.
I presented Holly my nicely lubed asshole that wasn’t as tight as it was when we started. She put the harness on, showing me a silicone dick that was about to go inside me. She looked amazing and I wished I could see her doing it.
She got behind me, letting me feel the toy spreading me like never before. I moaned, instantly loving the way the strap was going deep inside me while hitting some spot that was making me absolutely lose my mind.
“I love owning your asshole,” Holly said, slapping my ass and fucking me even faster.
I could only whimper as she did it, enjoying it all maybe a little bit too much. She didn’t even need to use her hands, I still spilled on the sheets, while she kept moving deep inside my ass. In the end, she pulled out, leaving my asshole gaping.
It started as an experiment, and I wasn’t sure about it at first, but now I don’t know if I’ll ever be able to live without it.
