A Night of Firsts

[Guest]

A Night of Firsts

When I got to Jay's, he was already prepared for what he had planned for me. It was straight to his bathroom, undress and then begin a series of seriously, gut-filling enemas. Once the water ran clear, he escorted me into his bedroom. I always felt awkward being in that room. Jay was "married" to his lifelong partner. That was technically their room, and despite constant assurances since the day we met online that his partner was okay with him having a slave, I always felt like I was a homewrecker of sorts—or at least a potential one.

On the bed was a set of thigh-high, fishnet stockings, a short, black, pleated skirt and a black tank-top that had SLUT in rhinestones across the chest. I was understandably confused.

"What's this for?"

"You said you used to pretend being a girl when you and your best friend would fool around."

"Right...and?"

"Tonight, you're going to be a girl. You're lucky you actually look like a fairly passable girl despite being over six-foot thanks to your curly, long hair. Come on...get dressed."

I was still unsure but also excited by a new challenge being presented to me. In a few moments I was standing at the foot of his bed all dressed up. I felt sexy, slutty, confident, vulnerable, confused, embarrassed...all of those feelings all at once as I looked at myself in his dresser mirror. Jay produced a pink chastity cage and told me to lift my skirt. This was something neither of us had ever discussed, and it was the first time that I had ever seen a cage in person. It took some wrangling to suppress my erect cock enough to get it locked away. My meat bulged against it—pressing my shaft's skin through every available open space. It was incredibly uncomfortable and simultaneously reassuring. It felt proper to have my cock locked away in this cute thing. As soon as my visual transformation was complete, his partner walked in and lifted my skirt front and then back. "Very cute," he said. "She's going to have fun tonight." Both men chuckled at the plan only they were privy to.

It didn’t take a lot of convincing to get me to walk into that adult bookstore; not nearly as much as one would expect. Perhaps that was thanks to the giant bottle of pre-opened water he demanded I drink on the way there. At some point, Jay had apparently slipped something into it. By the time we arrived, I was already cozy on cloud nine. While I realized that someone I knew might recognize me dressed as a girl in this tiny skirt that barely covered my ass, it just didn’t seem to bother in that headspace. Jay apparently knew the owner behind the counter, and with a flash of my ID, he waved us on with an impish smile. I was paraded up and down the aisles of the store while Jay feigned interest in the porno DVDs or sex toys for sale. I nearly fainted when a guy in his 50's with gray beard walked up to me and lifted the back of my skirt to grope my ass, and then reached around to wave my caged cock around. I stood silent, but Jay's smile let me know this was going how he had planned. By the third set of hands feeling me up, I was beginning to openly moan being manhandled like a bimbo.

"Come on," Jay said. I thought we were leaving, and I was actually sad. But rather than leaving, he led me through a door into an arcade. We walked silently down a poorly lit, stinky corridor. A series of doors close together were on our right, and we passed a single door on the left that had THETER misspelled on a strip of masking tape. Jay walked me into a room on the right. As I stepped in, I could see three of the guys from the store area coming towards us. It didn't even hit me until I saw the jizz-stained monitor playing porn that he had taken me to a gloryhole. This was something we had talked about in great detail doing. I was obsessed with the fantasy of going to one for the past couple of years. I guess I was so caught up in becoming a girl and being groped that I was blind to what was going to happen until we got into that room.

Jay moved the stool to the center of the room and opened the partition covers on both holes for the room. He lifted my skirt and we both saw the heavy string of precum that was hanging down from the tip of my dick. As soon as my bare bottom hit the stool, a stranger's hard cock was coming through the hole in front of me. Jay took out his phone and began recording as he told me that I knew what to do. I was so turned on and ravenous for this exact experience that I was immediately licking and sucking on my first anon cock. I was surprised and bit disappointed how quickly he came, but I was still happy to be swallowing my first anon load.

Another cock came through a few minutes later, and as I leaned forward to suck a new stranger off, I felt hands grabbing at my ass through the hole behind me. Jay told me to stand up, and he moved the stool to the corner of the narrow room. I kept licking and sucking as the new stranger's hands squeezed my ass, played with my caged cock through my spread legs and then I felt a finger push into my asshole. It was a moment of pure exhilaration and bliss being finger-fucked by one man with another's cock throbbing in my mouth about to explode.

The stranger behind me fingered my asshole rapidly with one and then two fingers. But then it suddenly stopped. As I swallowed strange load number 2, Jay pushed my hips back towards the wall behind me. I felt my little, bubble-butt depress against the rough wood. My mind was racing with a million wicked thoughts of what was about to happen. I just stood there, bent over, savoring the warm, salty aftertaste in my mouth waiting for what I knew was about to happen. A total stranger would be fucking me for real; no fantasy; no pretend roleplay.

I felt Jay sit his phone on my lower back and grab my ass from the sides. He pushed and pulled lining me up for the hole in the wall I assumed. I knew it was about to happen when he forcefully pulled my ass apart and told me to push back hard against the wall. I eagerly complied while Jay grabbed his phone off my back and pointed it right in my face to capture my every expression as my first true stranger penetrated me. I suddenly felt the stranger's cock against my hole. As he started to push into me, I moaned loud enough that I was a little embarrassed, but I couldn't help myself. I felt my eyes just explode open as this guy's cock forced me open. He was way bigger than Jay, and Jay appeared to love the fact this stranger was about to turn me inside out.

"How does your first anon cock feel?"

"It hurts soooo good," I moaned looking into his phone's camera lens.

The anon behind me was mercilessly pounding me. It honesty felt like the wall was going to fall over or shatter. Even our door was rattling and clanging. Then the thought came to me; long after this strange dick had been violating me. I couldn't help myself but to ask though. It was morbid curiosity.

"Is he wearing a condom?" I moaned in sync with his thrusts.

Jay leaned over my back and returned with a smile. "No."

"Uhhhh fuck," I moaned trying to hold my ass steady against the wall from the throttling it was receiving.

Moving the camera from my face to over my ass, Jay captured my very first anonymous seeding. I so desperately wanted to jerk off right as that stranger was flooding my guts, but that clever cage denied me relief. I just dripped and dripped. As the anon cock slipped from my hole, Jay quickly, and much to my shock, inserted a fairly large butt-plug into me. "We don't want that to leak out do we?" Part of me did, but the dirty, slut I was dressed as agreed with Jay.

I was ready for more loads, but Jay drove me back to his house. Together with his partner, we watched my night of taking three, separate, stranger's loads. They each took turns fucking my throat off the edge of their bed while tormenting my aching, caged cock.

[deepfix]

Loving these Jay stories, some of the very best imaginative writing on here, thank you. I hope the one featuring Jay’s own dungeon reappears, please.......

[lj1987]

That’s a brilliant start… 

[Moose143]

I wished I would have fucked at the gloryhole

[aussieamylpig]

damm that was hot, keep writing more