When I Take A Chance, It Pays Off
By: Date: 2021.09.02. Categories: Sex Stories Tags: , , ,

I sat down at a table in the food court of the convention. I was dressed as Emma Frost this particular day. It wasn’t my first cross play. I made a cool $300 of a friend of mine the first time, one who wasn’t convinced that I would do it at a con. My salad in front of me was somewhat unappealing, although I was really only eating it to keep up appearances. Many men had complimented me on the costume, and a few even asked me out that evening. I had denied them, since I wasn’t really interested in going out beyond the convention.

A man in a Goku cosplay asked to sit across from me. I didn’t think much of it and pointed at the chair. I, then, noticed the sheer size of him. He had to be 6’ 6” and weigh 250 pounds of muscle. I wasn’t small by any means, at 6’ 3” in my heels and 200 pounds. I took a bite from my salad, watching as he ate a burger. We talked for a bit, and I found out his name was Hugh. I gave him my feminine name of Mary. He smirked and asked me out that night. I told him that I wasn’t really interested. He grinned again and handed me a business care, just in case I changed my mind. He left me sitting there, really debating what my plans were that evening. I shrugged it off, finishing my salad and enjoying the rest of my day at the convention.

I eventually made my way back to my hotel room. I started to get out of my costume, when I thought of Hugh. I put back on my costume and called him. He picked up and acted to give me a lift over to his hotel. I stood outside, when a limo pulled up and Hugh stepped out. He motioned me into the limo, which I stepped into. He followed suit, and we rode to his hotel. It was a five star spot right by the ocean. We stepped through the lobby into the elevator, where he looked the button for the penthouse.

“I must come clean about one thing,” I said, during our ride up.

“I know you aren’t really a woman under there,” Hugh said, turning to look at me. “You are just so sexy that I couldn’t help trying to fuck you.”

I blushed and closed the distance. He took me in his strong arms and kissed me. My cock stayed put in the tether, but I knew that he was going to succeed in fucking me that night. He pulled back as the elevator dinged at the top floor. It opened to a massive bedroom with a king sized bed in the center. We stepped into the room. He closed the distance again and kissed me with increasing passion.

I felt myself being into his arms when he pulled away. He slowly stripped off his shirt and pants, leaving only his boxers on. There was an obvious bulge there. I took my time, stripping off the gloves, shirt, heels, and pants. This left only my corset and panties on my body. We crossed the gap again and kissed. I felt his arms go around me and loosen the corset. He stepped back to take it off, redistributing my little bit of fat back to my stomach, rather than the breasts the corset help simulate.

Both of us in the absolute littlest amount of clothes we could be, caused me to close the distance. I opened my mouth and accepted his tongue kiss. We wrestled tongues for a few minutes, when I broke from him. I dropped to my knees and took off his boxers. His cock was at full erection. It had to be 2 inches thick and nearly ten long. I kissed the head, then slowly worked it into my mouth. I got about half way down, when I felt my gag reflex hit. I powered through and started swallowing down his massive dick.

I felt him put his hands on the back of my head and slowly work on thrusting slightly deeper each time. He bottomed out, and I started working my throat muscles to milk him. Hugh pulled out after a few seconds though, saying that there was somewhere else he’d rather cum. I felt the same way, so I stood and removed my panties. My dick, finally free, sprang to attention. Hugh and I shared another passionate kiss, before he lay me front first on the bed. I pushed a pillow beneath my hips, as I felt something cold and wet greet my anus.

Hugh slowly worked in a finger. I moaned at the pleasure of it. I may have been a virgin, but I had experimented with some toys in the past, and his one finger was smaller than what I knew I could take easily. He seemed to realize this and placed in a second. He, then, vacated my anus with his fingers. I felt something long and stiff, but flexible and somewhat cold, work it’s way in. It had to be a dildo. This one was larger than what I was used to taking, but not to an extreme. He fucked me with the dildo for a few minutes, loosening me up with his cock to be the final entrant.

Hugh took out the toy and lined up his cock. I groaned as it penetrated me. He moved slowly, taking his time to enjoy himself. I adjusted fully to his size, and I started to feel great pleasure in his small smooth thrusts. He pulled out and rolled me over. Our eyes meet for the first time in a good five minutes. I didn’t think, only moved forward and kissed him again. I wrapped my legs around his hips. He took a second to make sure he was aligned with my ass, then thrust fully in. I moaned and reached forward with my arms, pulling myself up just enough to kiss him.

My cock ended up forgotten at this point. I was becoming his woman. He moved in precise right inch thrusts, causing my naturally large ass to ripple everytime he thrust. He picked up the pace, moving with shorter, more rapid strokes. My cock bounced along his abs. Without warning, I came between us. He thrust one more time and flooded my ass with his sperm. We came down from our euphoric highs, sticky, but satisfied. I clamped my asshole shut, while he pulled out. Hugh smiled and kissed me on the lips before heading to the bathroom.

I followed him into the equally large room. He started the shower, something I knew we both could use. Before he stepped in, I felt the desire to have his dick in my mouth again. I shook my head at the prospect and followed him in. I followed him into the shower where we took our time getting clean.

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