After one year in a secret AAIT – short for agency against illegal things – training facility they told me that I was ready to go on my mission. My mission was to infiltrate the NPC – short for no pussy clan – and collect information, evidence to bring the most dangerous, the most influential crime organization to a fall.

My training included everything that a secret agent needs to be trained in and a little bit more. That little bit more was turning me from a man into a woman, into a next to perfect more than just hot and beautiful sissy. The transformation so far was a total success, but there were still things that could be improved.

Those things were minor stuff like my behavior wasn’t one hundred percent female, my voice needed more exercise, in some situations I was still reacting more like a man than a woman and my chastity cage could be a little bit smaller. All in all nothing too dramatic, nothing that could be fixed within my first few months in my new undercover life.

It was in the first week of February when the agency sent me out into the field for the first time. They already had gotten me a job in a bar in one of the bigger cities our country had to over. The NPC was known to be active in that town, and it was far enough away from my old male life so that no one could accidentally walk into me and blowing my cover.

Not that it was very likely that someone from my old life, even my closest family members would recognize me in my new female form, but you can never be too careful with such things. And to be honest, I liked it that way. Because I wasn’t at a point were I wanted my family to get to know my new, my real totally feminine me. The same applied to those few real friends I had.

The bar itself was a half decent shit hole. Not the best place in town, but by far not the worst. It was a working man’s place. So when I was behind the counter, when I was serving them drinks, I often had their full attention. Plenty of them even wanted to stick theirs into mine, but I all the time said no. A good barkeeper doesn’t have sex with his customers.

Beside giving me a new job the agency had found me a eligible place to life in. Luckily they didn’t dumped me into a cockroach infested rats nest. My apartment was in a decent part of town, it was freshly renovated, it was equipped with some new furniture and some more than just decent electronics.

But the place came with one downside. It wasn’t the biggest place on Earth. Not because the agency wasn’t able to afford something bigger, but because it had to be a place that was in theory payable with the money I was earning while serving drinks in a bar.

And nope, there were no fancy secret agent gadgets inside it. Those things should show up later, when I was actually infiltrating the NPC. Because in that phase of the mission, there just was no need for the best spy equipment money can buy.

My working day back then looked about like the following: I got out of bed around noon, I went to the gym, I went to a vocal coach, then I did everything from grocery shopping to buying myself a new set of lingerie, or maybe a nice toy to train my butt hole and then I went to work. Serving hard working men their well earned drinks until past midnight. After some basic cleaning in the bar I headed back into my place to fall into bed.

But not without playing with myself for a little bit. Because being being surrounded by musky, sweaty and more than just flirty men all night long was nothing but a turn on for me. How would I have loved to take one of them home with me each night, but back then, in my early days as a barmaid, I didn’t do such things.

I followed the simple rule the owner of the bar had given me on my first workday: “You don’t fuck customers. Never. You flirt with them, you make them hope that they can fuck you, but you just do it to keep them coming back and drink.”

So I was playing with myself every day I came home from work, because other wise I wasn’t able to fell asleep. I needed the sensation of a more than just decent sized toy sliding in and out of my needy fuck hole.

I mostly took my time playing with my self. I squeezed my nipples, I squeezed my boobs, I fingered my asshole to warm it up, I made myself moaning out loud before the actually self fucking even began.

When I was warmed up enough, when my meanwhile tiny caged dick was spitting out some nasty juices, I took one of my dildos out of my nightstand, I drowned that thing in lube and then the toy went up my ass.

It all the time felt so damn good. It all the time was the highlight of my day back then when I gave myself one slow, hard and deep thrust after the other. My tight fuck hole was all the time needy back then.

It felt better and better every time the toy went out of my ass. To enhance my pleasure I often took another toy to suck on, to shove it down my throat, to make me airtight. To fill all the fuck holes I had.
And it all the time worked. I perfected the art of masturbation back then. I nearly all the time came. Either from anal only, or from anal and something down my throat. It felt so damn good when I was giving me one thrust after the other.

It never took long and my brain was off. It never took long and my moaning was filling my small apartment. I all the time lost myself in the sensation of something going in and out of my but. Sometimes accompanied by a toy going in and out of my throat.

In and out those toys went. Every next time felt better than the previous time. I kept on going until my legs were trembling. Until my caged dick squirted out some filthy sticky, but also tasty juices. It all the time came good. And after the tension was relieved, after the pressure was off, it never took me long to fall asleep.

But those self fucking sessions, they soon weren’t enough to fill my sexual appetite. I needed a real man fucking my brains out. But where to get one? When I was in the gym during day, mostly bored housewives were hanging out there. I spent my days off mostly at home, improving on my feminine side or just relaxing, because as mentioned above, my work days where long. So now men to run into either.

In the end I came to the conclusion to fuck a customer. Not the next best one, not a regular one, but someone that only was in town for a couple of days, maybe on a company trip. Some of those work travelers were actually showing up in the bar I was working in from time to time. And well, a plan was made. I wanted, I needed to get laid.

A couple of weeks went buy until a eligible candidate showed up. It was a not so busy day when a men around thirty entered the bar. His clothes told me that he was a businessman. He looked hot in them, and there was a decent sized bulge between his legs too.

I was a little bit nervous when I served him his first non alcoholic drink. So dragging his drunk body home was no option here. But luckily he was sitting at the bar. That made it a little bit easier for me to work my seduction magic on him.

There was plenty of bending over, plenty of showing off my cleavage happening that night. Not that things like that weren’t happening in other nights, because doing something like that drove the sales numbers, but in that one night, it was directed towards the about thirty year old businessman that was sitting at the bar right in front of me.

And it didn’t took long and I had his attention. I was talking with him, flirting with him while I was pouring drinks for the others. I actually enjoyed the conversation we had up and running, so probably did he, because he wasn’t leaving. He stayed until the last drinks were served. Something that sober people rarely ever do, because being sober beneath drunk people, something I had every night at work back then, is mostly nothing but a big pain in the backside.

In the end he was the last one left inside the bar. Except me. We still were talking, but we were mostly undressing each other with our eyes. We clearly had the hots for each other, so when I went over to the bars entry door and when I locked it I broke the ice. We both knew what would come next.

I went back to him, I sat down on the empty bar stool next to him and then our eyes met each other. There wasn’t love in our eyes, it was lust. Pure horniness. And it all unloaded itself not even a minute later.

Passionate kissing set in and our hands were all over each others bodies. It didn’t took long and our clothes were flying through the air and landed every where. Some of it even spilled over some half full glasses, but we two couldn’t care less. Our inner horny animals had taken over control.

When we both were naked, when he saw the caged dick between my legs, a enormous smile appeared on his face: “Oh, you are one of those. I love your kind. But I think we need some lube.”

I blushed a little bit when he said the words above, then we kept on kissing while our hands were exploring each others bodies. It didn’t took long and my hand was on his rock hard dick, sliding up and down, making him moaning out loud while he began to finger my dirty hole.

We both were moaning out loud, his finger up my ass, it made my mind melt away. And my hand on his hard one, and my other hand on his balls, squeezing them gentle, made his mind melt away.

I worked him closer to an orgasm while he prepared my fuck hole for penetration. My caged dick was already spitting out filthy juices while more and more tension was building up between the two of us. Then I went to get some lube. Luckily I had some of it in my purse, because you never know.

He was playing with himself while he watched me disappear in the back of the bar. I even shook my ass for him while walking into the backroom. Once I was back in the front we shared another set of passionate kisses. My hands were on his ass, and his hands were squeezing mine.

Then he grabbed the lube I just had placed on the bar next to us. He lubed up his rock hard dick, then he bend me over one of the bar stools and poured more than plenty lube over my ass hole. The moment the cold lube touched my butt, a shiver went trough my body.

When we both were lubed up he placed himself behind me. His strong hands grabbed my waist and then I felt something pressing against my needy, already tingling but hole. Then he went inside. His more than decent sized dick went up my ass. It already felt nothing but good. Moaning escaped my body.

He went in gentle, but balls deep. He stretched out my fuck hole. Then he gave me a few gentle thrusts. My mind already began to turn off, my moaning, and his too, were filling the empty and closed bar.

After maybe ten gentle thrusts to warm me up, my eyes were already running in circles, my caged dick was gushing out some filthy sticky pre cum he upped the pace. He fucked me harder, he fucked me deeper and he fucked me faster. It didn’t took long and all that mattered for the two of us was the sensation of his dick sliding out of my ass.

But he still was holding back. He did so until I moaned out a “harder.” Then he finally let go. He fucked me so damn good from that moment on. My brain was off, my eyes were running in circles and I came closer and closer to an anal only orgasm while my caged dick was bouncing back and forth while spilling sticky juices all over the bar stool I was bend over.

The businessman was fucking himself, he was fucking us towards an orgasm. Sweat was running down our bodies. While his hard one went in and out, in and out. Then one last out, and one last in.

He emptied his balls deep inside me. He dumped a enormous load of his sticky juice up my ass. I came a few moments after him. My legs were shaking, my hands stopped holding on to the bar stool and then I collapsed. I was gone, I was in orgasm happy land. But so was he.

It took us some time to catch our breaths and to regain ourselves. Once we were back in our bodies we both had a more than just satisfied post orgasm expression on our faces. I then grabbed some paper napkins and cleaned my ass off his dick.

Then we both went into the bathroom to fix ourselves up as good as anyhow feasible. After collecting the clothes and cursing, laughing a little bit about the fact that some of our clothing went for a swim in a half empty beer glass.

But laughing that was all we did. We weren’t talking and now that horny was cured, the attraction towards each other had left the room. We both knew that this was a one of a kind, we both had enjoyed it, we both got out of it what we wanted and so he said goodbye and left the bar. Well, I had to let him out, because the door was locked.

After the first time fucking a total stranger had met at work was a that big success, I began having sex with men showing up in the bar on a more or less regular base. I enjoyed every load of cum that landed inside or on my body. And what I didn’t knew back then, I was already making contact with some members of the NPC.

The agency itself was very quiet in my first six months undercover. They for sure were keeping a close eye on me, but neither my agency contact contacted me nor the agency itself. I just was living and enjoying as a damn hot sissy bartender back then. But things should change soon.

NSFW: yes