I’ll never forget my first time.

It was phenomenal. Not my first time having sex with a guy — because let’s be honest, that particular experience for most of us falls somewhere on a spectrum between mediocre and awkward. I mean the first time I got to fuck someone with a strap-on. The first time I got to feel the addictive rush of bending someone over and hearing her moan as I pressed deep inside her.

While working at the dungeon, I began to discover some of my own fetishes by getting to explore what my clients were into. Sometimes something unexpected would turn out to be my obsession for months to come, but I rarely got to fulfill my own favorite fetish since it was against the rules.

I may not have gotten to unleash my strongest desire with my clients, but in my coworkers I found a tribe of unapologetically sexually adventurous women who were always up to no good once they were off the clock. When I revealed that I had penis envy but had never used a strap-on, my coworker Raven vowed to rectify the situation. She announced she would be hosting an impromptu strap-on party at her place after work and began to spread the word within the scene. Game on.

The party was immediate enough that I didn’t have time to get nervous and overthink it. I’m such a planner that I probably would have been watching strap-on porn and taking notes to prepare and then been terrified to make a mistake when it came time to do the deed.

Despite being employed at a dungeon, I was still an innocent compared to the rest of the partygoers, but I tried to play it cool and act like I had seen it all before. I thought I was doing a pretty good job of blending in until Raven turned down the music and told everyone to gather round for the main event.

I shifted toward the center of the apartment and peered over at Raven, excited to see someone get fucked, only to find Raven looking directly at me, waving a strap-on harness with a knowing smirk.

“Scarlett has never fucked anyone before and desperately wants to stick her dick in someone. Any volunteers?”

I was blushing so intensely that people must have thought that’s where my name had come from. When most of the room volunteered, I had no idea how I was going to pick. Did I want my first time to be with a man or a woman?

A soft voice from behind me said, “I’m a strap-on virgin, too. Why don’t we pop our cherries together?”

I turned to find Lily, a fellow submissive from the dungeon, smiling at me eagerly. She was a petite but curvy blonde whom I had only worked with a few times.

“Perfect,” I said, returning her smile and feigning confidence. “Let’s do it.”

I could feel the anticipation of the crowd build as we both stripped down. I was delighted to discover that Raven’s harness had suspenders built in, another one of my strange fetishes. Raven helped me step into the harness and get the straps adjusted correctly around my hips and thighs. As I looked down to see a massive, rock-hard dick sticking out, I was amused to be reminded of the first time I’d carried a gun. I felt powerful and masculine.

By the time I was ready, Lily was completely naked on all fours, peering over her shoulder at me as she arched her back in invitation. I stepped forward and could almost hear the people around me holding their breath as my dick brushed against her plump ass. There was so much expectation that I felt like I should just go for it and thrust into her right away, but that wouldn’t be fulfilling for either of us. We may have had an audience, but I didn’t want our first time to just be for show.

I grabbed my cock and ran it softly along her slick folds until I found her clit. I ground against that bundle of nerves until she was panting and pushing back against me. Instead of giving her what she was begging for, I slid my middle finger into her pussy, reveling in the wet heat and the way she moaned as I stroked her G spot and her clit together. From the way she eventually began to writhe and clench, I thought I could make her come, but didn’t want that to happen until my dick was buried inside her.

I pulled my finger out and replaced it with the head of my cock, rocking forward an inch at a time. I was pacing myself, savoring the visual of slowly driving into her, but Lily was finished with being teased. She slammed back against me, pushing my dick in all the way to the base. I wanted her to get off, but didn’t want to block my view by leaning over her to access her clit. Raven seemed to anticipate my conundrum and reached under Lily with a vibrator. The moment it made contact, she began to ride my cock so hard that all I had to do was brace myself and enjoy the view.

She didn’t last long before she tensed and came with a guttural groan. She was no longer on all fours, but lying with her chest on the ground and her ass in the air. She was panting and tossing her head from side to side in delight. I gave her a minute to catch her breath, but when she started to rise, I pushed her shoulders firmly back onto the floor. It was my turn now.

Raven turned the vibrator back up, and I started to thrust into Lily in powerful, punishing strokes. It was a foreign motion at first, but I quickly found a rhythm and got caught up in the moment. As I watched her come again and again while I hammered into her, I knew I would never forget my first time.

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