Undercover Sissy Pt. 01

All characters are 18 or old. Enjoy.

I have been an XBI agent, or more like a trainee, for three years. I'm still waiting for my first real mission. What they are giving me now is mostly paperwork. My colleagues are happy that I'm working on the desk because they think I'm not ready for field missions. I know I wasn't the best in my training, but I was not asking for a one-man army mission. However, I never ceased asking my supervisor to assign me a real task so that I could show my ability to prove them wrong.

One day, I was busy at my desk trying to find the perfect mission that would look silly, but at the end of the day, would be a hell of a mission. After hours of searching, when I lost my faith in being a real agent, my boss called me to meet him at the office.

"May I come in, sir?"

"There's my favorite agent! Come here, boy," Boss responded. "I have a real mission for you this time, and I think you're the only man for the job."

Finally, my luck has turned for the better. "I'm listening. What's the job, boss?"

"OK, it'll sound strange, but it's the only way to get inside and find their real shit with evidence," Boss explained. "And it's pretty tough."

"Now I'm more interested."

"That's the spirit, boy!" Boss replied. "Don't freak out!"

"We are professionals, Boss."

"All right, when you're undercover in this gang, you have to dress and act like a girl," Boss said quickly as he handed me the case files. "You'll find all the details in there."

"What! If I have to dress like a girl? Then why don't we assign a real girl?"

"Well, they already have plenty of girls and men inside," Boss responded. "We tried that already, but it didn't work."

"So, what's the difference now?"

"This time, we found a new way," Boss replied. "They also love having sissies as their gang members."

"What, as a sissy? Are you sure I'm the man for this mission? I'm straight."

"So?" Boss said.

"Aaa, I'm..."

"You want it or not?" Boss barked a little.

"Yes, but..."

"You don't have to," Boss explained calmly. "I'll find another trainee. Now get out of my office."

I was leaving, but he called out to me from behind my back.

"If you change your mind, talk to Agent M," Boss said. "This case is so important. If you can solve this, I'll personally talk about your promotion with the higher-ups."

"What if I fail?"

"Still, you are having a real mission," Boss responded. "It's your call now."

"I know. Do you have any..."

"This is your chance to prove yourself," Boss replied. "Don't ask me later for another chance."

"Can I think about it?"

"You leave the building without accepting the mission," Boss paused. "I'm handing it over to someone else who wants to be a real agent."

After lunch, I was thinking about the offer. If I take this job, I will have to be a faggot, but the reward will change my life. I'd always dreamed of becoming an agent. Fuck, my boss is right. I should take the opportunity. I'm about 5'10 with little body hair naturally anyway, with blue eyes and what I've always been told is a classically attractive face that I can fairly easily feminize and be passable. Let's give agent M a visit.

"Hey M, how are you doing?"

"Good," Agent M replied.

"Do you really love to spend all day in the lab?"

"Don't try to get familiar. I know why you are here," Agent M responded. "Strip naked and stand on that disk."

"Hey, easy. I was just... bla...bla... bla."

"Are you done?" M replied. "I have lots of work to do."

"Alright, alright. Just don't bite me."

Then, I stripped naked and stood on the disk as she told me. It was not the first time I got naked in front of a colleague. It's totally normal here, but this time it seemed different. She started inspecting me and taking notes on her tab. After a while, she finished taking notes and told me to get dressed.

"Let me run the program with your data," M said. "I updated the last program; now it's super fast and efficient."

"So, your computer will decide what I need?"

"You want me to decide?" M responded. "It's the same thing, me or the computer. Don't forget, I built this program."

"Looks like it's done."

"Yeap, let's see what we have here," M said. "Boss wasn't wrong about you. You are perfect for this job."

"Are you guys stopping this play? Just spit it out."

"Well, your body is close enough to look like a female body," M said. "And less hassle for me to turn you into one."

"What's that supposed to mean?"

"I mean, you are skinny with a small penis," M chuckled. "Which is the perfect combination for our mission."

"Hey, it's not that small."

"Not that small, but small enough to get fucked in the ass," M murmured.

"What was that?"

"Nothing," M replied.

"It's my flaccid dick size."

"Yea, 2 inches," she replied.

"Hey, I'm a grower, not a shower."

"Ok, then grow it and prove me wrong," She chuckled. "You need a hand!"

"You know what, I have nothing to prove to you. Let's get back to work."

"Yes, you have noo... So, first things first, we'll turn you into a girl," she said. "We'll try our best to give you a feminine face. Fortunately, you have no beard; hormones will take less time to change you."

"Hormones? Have you gone nuts?"

"Don't worry, she replied. "I can reverse it."

"You sure?"

"If you want, my treatment will help you grow a beard and muscles," she replied. "I can give you your dream body."

"So what exactly are you going to do with my body?"

"For this mission, I'll just make you look like a girl. Here are your prescription and medicines. Follow the instructions exactly as written and do those exercises regularly," she said. "Don't panic if you notice changes in your body. I can reverse everything. I'll make you a man again, or a real one for the first time, with lots of muscles. Maybe I'll try to grow your baby penis too."

"Seriously, you can make my penis big after the mission. I'm having trouble with girls in bed; you know what I'm talking about."

"I promise if you solve this case, I'll give you whatever you want," she replied. "Now start acting like a good girl. We don't have that much time."

Agent M's treatment was like magic; within three months, she changed me into a girl with B-cup natural boobs. But the real challenge was pretending to be a girl, and not just any girl, but a cheap prostitute. Agent M had stated that her medicine would change my gender identity, but I still doubted that I could have sex with a man. That was the reason they gave me a test drive mission before the real one.

On my first field mission, I was standing on a dimmed street corner in stiletto pumps, fishnet stockings, a black miniskirt, a see-through mesh top, with a black bra, pink panties, and Parisian Red lipstick.

"You're not acting slutty enough," Agent M scolded. "Walk back and forth down the street, and make sure you wiggle your butt."

"I think I'm doing well."

"Do what I say or all of our efforts will be meaningless," M barked a little. "Keep smiling. Soon you'll find a cock."

In my head, I thought I was still attracted to pussy! But over the past three months, I'd learned a lot of things, like how to suck and ride a cock like a pro. I'd still never done it with a real cock; it had always been a big dildo. However, we were trained to adapt to any kind of situation, both physically and mentally. The best way to keep my mind straight was to think about my future.

Suddenly, a car stopped behind me. "Hey, you! get in."

I looked back and saw a middle-aged man called me to get in his car. "Finally a customer." I got close to the car, and the guy lowered the window glass. "$50 for a blowjob!"

"$10, I want a quickie," the guy replied.

"$30. I'll let you cum inside my mouth." Fuck! I was bargaining with this piece of shit for blowing his cock.

"You're doing great. Make it appear as if you're a cheap whore," Agent M warned me. "Otherwise, you know what's going to happen."

"$20, you have to take me deep inside your throat, deal," the guy replied.

"Deal."

It was better than tasting his cum. I hopped in his car and started to unzip his jeans. I have enjoyed getting many blowjobs, and now I'm the one who will perform one. His cock was just in front of my lips. It was time to suck a real cock! I leaned forward and took his throbbing cock in my mouth. It was warm, silky, and exquisite in my mouth; it was better than a dildo. On the first suck, I went as deep as I could. I discovered that I was having fun with it! I was sure he was having a good time too because the sounds he was making were very familiar to me.

"You're good, whore," the guy groaned.

Its taste and smell weren't as bad as I thought. Honestly, it was far better than tasting silicone. I'm losing my working time. I have to take him into my throat. I pushed hard to get his nearly 7-inch long, possibly 5-inch girth cock in my throat.

"Mmmmm...Mmm...slurrr...rrrpppp...mmmm." Fuck, I was acting and thinking like a whore.

I widened my mouth, relaxed my throat, and swallowed him whole. I even licked his balls while sticking my tongue out. I took him in and out, further and deeper, till his glans were on my throat and his shaft felt comfortable. I was having as much fun as he was. He was getting close and ready to cum, but he wanted to make sure I was as well.

He moved his hands toward my crotch, but I wasn't ready for that area. I pushed back his hands. Then, I got so focused on the incredible sensation in my mouth that my cock began to tickle.

"Mmmm, mmhmm."

I felt he was about to blow. I grabbed his thighs and held them strong. Then he blew shot after shot inside my throat, which went directly into my stomach. He pulled my head a little bit up and then pushed it back where it was to extract more cum.

He was fucking my throat as if it was a pussy. This guy was cumming like a bull. He had filled up my stomach and was now filling my mouth. By the time he stopped cumming, his thick, hot sperm was all over my tongue.

"Fuck, you're damn good, whore," the guy moaned. "Give me your number. My friends would love to dump their load into your throat."

At first, it felt disgusting that someone else's cum was inside my mouth, but the taste made it different. It was so good. I loved it. I even cleaned his cock.

"You have a big thick cock, sir. Here is my number, you can call me anytime."

"Here's your $15," the guy said as he threw the cash toward me.

"What the..."

"Get out of my car, bitch. Don't make me hit you in the face," he yelled.

"You cheap dog. If you don't have money, then don't expect to get blown by someone. And delete my number, asshole."

I should have given him a punch. Fucking shit. "Hey, M, are you there?"

"Yes, I'm here," Agent M replied. "You have done a great job."

"Should we teach him a lesson?

"Now chill the F out, M replied. "We already get paid for this shit. Go home."

"Okay, but I'm still mad at that guy."

"First thing tomorrow morning, you come to my lab," M responded. "I have a real task for you."

"Bye."

"See you later, whore, hehehe," M laughed.

"Haha, so funny." I'll have my payback, bitches, just waiting for my promotion. The next day, the first thing I did was go to M's lab.

"Get naked," she said immediately after I stepped inside her lab and then stripped down.

"Okay, let me take a look at you. Wow, it looks unusually small today," she said, reaching down to hold my limp manhood between her thumb and forefinger.

"Yeah, I noticed it too. It shrank a little bit."

"Don't worry, it was supposed to happen," she replied. "Like your nuts get shrunken."

"Is it healthy?"

"Totally," she replied. "There's still a little work to be done, but we can start our mission now."

"You want to shrink it more?"

"A little bit more," she responded. "So tonight you'll visit a nightclub and try to get some attention."

"That's it?"

"Yes, nothing, more or less, just like yesterday," she replied. "I already sent the files to your desk."

After that, I was reading the files when my boss stood in front of me and started checking me out from top to bottom. I was wearing a women's secretarial outfit that was quite slutty, but what could I do? Agent M was in charge of everything, from what I wore to whom I sucked. I was a little uncomfortable because my boss's crotch was a few inches from my face.

"You're doing a great job," Boss said. "I watched the footage of you sucking a cock."

"Thanks, boss. I tried my best."

"Honestly, that was awesome," Boss exclaimed. "I wish I'd been the guy that you were sucking!"

I was shocked and looked at my boss like he had just snatched candy from a kid. I could see his tent was moving and pulsing.

"Hahaha. Boy, I was joking!" Boss laughed. "Look at that face, but you have to be prepared."

"Haha," I smiled.

"Good luck with today's mission," Boss said. "Most of the guys in that party are criminals, so be careful."

"I'll be."

"Remember, one wrong move and you may get killed before our team..." Boss raised his eyebrows. "It'll be a waste of money and time if I can't feel your lip..."

"What the fuck was that? I know my character well, but I'm in the office right now. Horry bitch, I could feel your cock's warmth on my face and that disgusting bulge." I murmured.

In the evening, I went to the nightclub. It was easy to get inside because of my slutty dress, Antopmen Women Sexy Spaghetti Strap Crop Top Side Lace Up Skirt Outfit Two Piece Bodycon Bandage Dress. But the real challenge was to get into the private party, which was my actual mission.

The guard was a large, muscular black man who wore a suit and dark glasses. As he opened the door, his eyes were rolling over my sexy outfit and body. "Mam, your id."

I handed over my pass, stepping inside the door.

The guard hesitated a moment and said something to the control room. "Turn around and face the wall. I need to check you for weapons or bugs," he ordered.

I complied, and he immediately ran his hands down my sides, his probing fingertips searching for any hidden weapons or bugs. He slid his hands down the outsides of my long, bare legs, even though there was obviously nothing there. To my surprise, on the return trip, his hands ran up the inside of my thighs, under my short dress, where he cupped my tiny penis and balls through my panties.

He looked right into my eyes and then got back to his work. I gasped as his fingers pushed my panties aside and briefly probed up into my ass before withdrawing quickly from under my dress and moving up to my hips. His hands' cup and squeeze my perky B-cup tits as they move up and around my sides. I heard the guard groan a little as his hands worked my tits over, mauling and fondling them vigorously.

I kept my mouth shut. Actually, what was happening was supposed to.

After a full five minutes, he finally released my boobs. "Hmmm," he murmured, "I can't tell if you're carrying anything or not," the guard said. "I need you to take off your dress, ma'am."

As he said, I slowly pulled up my top. He kept staring at me lecherously while I was pulling the skirt off my hip and letting it drop to the ground. Beneath my ensemble, there was a black lace bra and matching panties.

"Hmmm," the guard groaned, eyeing me up, "Let me check." With that, he moved forward and reached out, cupping my big tits through my bra and squeezing them. He stretched his fingers out, but his hands weren't quite large enough to cover my bosom before he mashed them against his palms. The guard then pinched my nipples through the lace and shook my tits by them, his eyes taking in the sight of my flesh wobbling and jiggling beneath my bra.

"I think you've got something in there," he said. "Take off your bra as well."

I sighed, deciding it was probably better to let him have his fun than cause any trouble. I should keep obeying them because my face wasn't familiar to them and all the girls were fucktoys for them anyway. Then I reached behind my back, unhooked the bra, and pulled it off.

"Oh yes," the guard smirked, "You have definitely got something there," and he again reached for my tits. The guard moaned loudly as his hands closed roughly over my bare breasts. For what seemed like an hour, I stood there as the horny guard manhandled me before he finally released me.

"OK, you can go," he finally said, waving me inside.

I didn't need to be told twice. I quickly got dressed again and hurried into the house. I was thankful that the guard hadn't demanded to check what was inside my ass or boypussy before letting me pass.

To be continued.