I've been interested in pegging for a long time. It started with watching pegging porn, then experimenting with toys and plugs on my own. I always wanted to get pegged, but being that it's somewhat of a taboo topic, I've just been way too nervous to ask a partner. I decided I didn't want to go through my life without having tried it, so I found a sex worker that specialized in pegging. Her name is Emma.

Her whole career has focused on specifically pegging and prostate massage—that's all she does! When I found her profile on Tryst, I decided that the next time I visited her city, I'd see if I could schedule something. Of course, an opportunity arose, so I sent her an email and got things set up.

The day came and I arrived in the city. I hit the gym, then got checked into my hotel to get cleaned up—both inside and out. I was an absolute nervous wreck! Not only was this about to be my first time with a provider, but also my first time being pegged. Emma sent me a text and we confirmed our meet time. I made a quick trip to grab a bottle of wine (mostly to calm my nerves), then waited for her text that she had arrived.

Once she was at my hotel, I met her downstairs, then led her back to my room. Emma is blonde, about 5'5", and slightly curvy but in all the right places. Once we got to my room, we sat on the couch and chatted for a bit. She asked about why I was interested, what my expectations were, what my boundaries were, and told me a little about how she generally likes to do things for first timers. After chatting and drinking a glass of wine, it was time to begin. I got completely naked, and she stripped down to a nice pair of black panties and bra. Her breasts we at least D cups, held perfectly in her bra. She told me to lay face down on the bed.

She started with a massage. Taking oil and rubbing my back, shoulders, arms, and slowly moving down. Once she started massaging my ass cheeks, she paused and put on gloves—that's when I knew it was time. She slowly started moving closer and closer to my asshole, gently probing it with her finger. She slowly slid one finger all the way in, which made my cock twitch and me let out a moan. She gently moved her finger in and out, then added a second finger, which made me let out another moan. She moved two fingers in and out of my ass, using the other hand to caress my ass and back. I was surprised a bit when she moved to three fingers. It didn't hurt, but I could definitely feel my ass stretching to accommodate. After a few minutes, she told me to turn over on my back.

She stood up and put on her strap-on. It was the smallest dildo she brought, which seemed like a good place to start. I raised my legs up and she guided her cock toward my ass, gently entering me. After an initial adjustment, she got into the rhythm of fucking me. It felt absolutely amazing. Her breasts hung in my face as she moved faster and faster. After about 10 minutes, she asked if I'd like to try something a little larger—which sounded amazing.

She swapped to a slightly longer and thicker dildo, and removed her bra, revealing a perfect pair of breasts. She also reminded me that if I wanted to touch them, I could. From there, she placed the tip of her cock at my asshole and started to press it in. It didn't look that much larger, but I could absolutely feel the size difference. I had to ask her to pause to let me adjust to the increase in size. Once I felt comfortable she got into another rhythm, this time deeper and slower.

After some time, she reminded me that our time was almost up, and if I wanted to cum, I should do so soon. I placed one hand on her breast and used the other to stroke my cock as she fucked me. Eventually, I let out a loud moan as I shot a huge load on my stomach as she fucked me, my body shaking with one of the most intense orgasms I've ever had.

I'm glad I got to experience being pegged and I'm definitely going to bring it up with a partner in the future.