Crime Doesn't Pay

::A note for the readers. I came upon the idea for this story some time ago. Most forced feminization stories are told from the POV of the subject being forced. I decided to change the format a little and tell a story from the other side. Special thanks to Anelle for help in editing.::

I had originally intended to move straight from one apartment to the next after my lease expired. Sadly, the previous tenants in my new apartment decided it was easier to abandon the place, leaving it absolutely filthy instead of cleaning up. Since the landlord needed extra time to make the apartment livable, I found myself looking at two weeks of homelessness. The landlord was apologetic about the situation and gave me free month's rent as an apology; So instead of bumming on the streets, I decided to indulge myself. I found a decent hotel in my limited price range via Priceline and decided to relax a bit and enjoy my mini staycation.

I had never stayed in anything above a Motel 6 off the interstate, but I got a great deal on a four star hotel in a wealthy part of town. Although the business had a great reputation, it had been in the news lately, and not in a good way. The hotel had recently suffered a string of robberies that left police baffled and guests furious. I wasn't too worried. I figured that aside from my tablet, a thief could steal everything I owned and I would be out less than $200. Besides, I was used to staying in sketchy motels, so I packed a few clothes into my small rolling suitcase, grabbed my phone and tablet and headed across town to check in.

You can always tell a super swank hotel by entering the lobby and this one was no exception. There were several expensive-looking armchairs and couches for guests to sit on. I scanned around quickly and saw a number of hip, trendy young adults sipping lattes from the attached coffee shop and staring intently at their laptops. One young man with shoulder-length hair looked up and nodded a hello as I came by, but most of the others ignored me completely.

I approached the front desk and got everything squared away. The clerk was openly eyeing me and I was certain he was going to deny me a room for violating their dress code, but his tone and mood seemed to improve significantly when I pulled out a roll of hundred dollar bills to pay him. In reality, that cash was the security deposit from the apartment I just left and I don't think I'd ever had that much money before in my life, but I wasn't in a hurry to tell him that. The clerk gave me a sly smile and offered to call a bellboy to take my bags up to the room.

"Oh, don't trouble a bell boy." I said, "I only have this one bag."

"Nonsense, Sir. We take good care of our guests here." The clerk gave me a sly smile and called across the lobby. "Andre, please take this gentlemen's bags up to room 408." The bellboy came up, grabbed my small bag and looked around expectantly for more.

"Nothing else," I said apologetically. "I can take it myself if you like."

"No, it's fine, Sir. Right this way." I felt like a complete jackass, but I followed the bellboy to the elevator. When we got to the door, I thanked the bellboy for his time, gave a more than generous tip and opened the door.

I was instantly blown away by the quality of the room. I'd never been in anything so luxurious in my life. Seeing a wonderful opportunity to impress a girl, I grabbed my phone and started scanning through contact to find a willing young lady to share this wonderful experience. After a few rejections, I finally got an affirmative answer from an attractive ex-girlfriend, on the condition I drive out to pick her up. I agreed instantly, and with some less-than-saintly thoughts about the evening ahead, I got ready to head out. Before leaving, I threw my bag in a chair and took advantage of an old travel trip and spread a few pennies over the top of my suitcase. Finally, I sent a quick text to let the ex know I was on the way and headed down to the lobby. I was surprised to see that the chairs and couches were mostly empty, excepting the one guy who acknowledged me earlier. I nodded to the desk clerk, got in the car and started out of the drive.

I had traveled about fifteen minutes or so when I got a call from that evening's companion. "I'm sorry" she said, "but something's come up and I can't make our date tonight."

"Come on," I said, "I can't let this wonderful room go to waste." Sadly, she wasn't to be convinced and with a sigh, I turned my car around and turned back towards the hotel.

I stormed through an empty lobby and made a bee line for the elevator, ignoring the calls of the desk clerk and went back to my room. I instantly realized something was wrong when I saw the "do not disturb" sign had been hung on the door, something I certainly hadn't done before leaving. As quietly as I could, I slipped my card key into the slot and opened the door. Without warning, I threw on the light and loudly asked "All right, who's in here?" I was amazed to see a prone figure lying on the bed.

"Yo!" I barked, "What are you doing in my room?" After a bit of shaking, the figure stirred and looked around, disoriented. I instantly had the feeling I had met him before, but I couldn't quite place him.

"What? What do you mean your room?" He sat up and looked around before coming to his senses. He apologized and explained with slurred speech that he had been drinking all day and stumbled back. Thinking he was in his room, he just crashed on the bed. He grabbed his backpack off the floor and moved towards the door before I yelled at him to stop.

"That's a nice try" I said, "you might have fooled me, but you screwed up... big time."

He turned pale for a second, but then responded

"What... What do you mean?"

"The bag" I said, pointing towards the chair. "I left five pennies on that bag. They're now lying on the floor, just where'd they'd be if someone opened it up not knowing they were there."

My visitor looked like he was going to faint, but instead made a fast move for the door. Sadly for him, I was faster and got my body in the way, blocking his exit.

"All right, you should start talking and start talking quick or I call the police." For just a moment, the stranger looked defiant, but a quick step towards the phone broke his façade.

"Please man," he said pathetically, "don't call the cops. I didn't steal anything anyway. There was nothing in the bag but clothes."

"Don't you think I know what's in my own bag? What type of idiot leaves valuables sitting around in a hotel that's always getting robbed?"

"You don't know these rich folks" he said, inadvertently confessing to the crime, "They leave all kinds of things lying around. I mean, it was just last week that I....." He trailed off, finally sensing that he'd given away far too much information. After an awkward silence, I continued the conversation.

"So it's you. You're the one behind all these thefts. How have you been getting away with it? You don't have the most original approach." I looked at him for an answer, but he averted his eyes. "I can make a phone call if you want, I'm sure the police will get an answer."

"No, please. Look, the desk clerk is a friend of mine. It was his idea. Whenever he thinks somebody has a good haul, he lets me know and I wait till they leave and clean out the room. He stonewalls the police and helps cover up the thefts. With his help, I never needed a complex plan. He called me and warned me you were on your way up, and I jumped in the bed. We've pulled off the 'I'm drunk' excuse before."

As I looked over the thief, I suddenly remembered where I had seen him before. It was the same guy I saw working on a laptop in the lobby, the guy who nodded at me as I entered. Seeing him up close, I saw that he had a very soft look to him, no facial hair and a slender build. I was confident that I could take him in a physical fight, and he hadn't pulled a weapon yet, so I felt secure. I also understood why the clerk yelled the room number across the lobby and why he tried to call me over when I came back in. It really was a good theft plan. With a confidant on the inside, he had plenty of warning. Seeing an opportunity to administer a little justice, I started making demands.

"Open the bag," I said. "I want to see what else you've stolen." He slowly opened it up and dumped the contents on the bed. He had a nice pile of jewelry, a couple of portable electronics and some expensive looking ties. "A nice little haul" I continued. "What's in the front pocket?"

"I don't know" he said, "This is all from this afternoon. I just stole the backpack from the room next door before I came here." I told him to open it and we both a great surprise as he pulled out a full set of women's clothes, complete with bra and panties. He started laughing and made a small comment about how he'd love to see a girl in that outfit. I don't know what made me think of this, but suddenly thought of a great plan for teaching this thief a lesson.

"Put it on" I said firmly. The guy almost choked.

"What?" he said, "you can't be serious."

"Do I look like I'm joking? Put it on. All of it, or I make a phone call."

Slowly, the guy resigned himself to his humiliation. He grabbed the women's clothes and headed towards the bathroom. I stopped him and forced him to change out there in the room. With a lot of eye rolling and a few muttered curses, he dropped his track pants, revealing a basic pair of jockey shorts underneath. Slowly, he put on the first piece of clothing: a pleated grey and black plaid mini-skirt, something like a school girl would wear. Unfortunately for him, he was a little bigger than whoever he stole it from, so the effect was more of a slutty Halloween costume. Next he took off his shirt and put on the top, a midriff bearing red crop top.

I suddenly found myself getting excited by this little display. I had never been with a guy before, and normally I wouldn't even look at another male this way, but seeing him humiliated and feminized like this was a real turn on. I decided to take advantage of this opportunity and prolong my fun. As he sighed one last time and started to take off the top, I stopped him.

"Freeze. I said "all of it" I motioned toward the underwear still sitting on the bed.

"Oh come on, man." He said, "How far is this gonna go?"

I fought the urge to throw out a devilish smile and made my move: "I'll make you a deal. I'm thinking of four things. None of them will harm you or require that you leave this hotel room, and if you do them all, and I mean all of them, I'll let you out of here without a call to the police and forget I ever caught you in here. First up: You need to put on all of the clothes, bra panties included. You can go into the bathroom to get changed."

For a moment I was sure he'd rather have me call the police. The fear of jail must have been heavy though, because he simply sighed again, grabbed the remaining garments and went into the bathroom. While he was gone, I quickly pulled out my tablet and set it on the nightstand to record everything for prosperity. Then I threw my phone into my pocket and sat back down to enjoy the coming show. I didn't have to wait too long, as a few moments later the door opened and my new companion stepped out. I could see the bra outline under his top and the short skirt length left revealed a pair of sexy black panties with a sheer back, exposing his entire ass. I stood up and casually walked around him, taking in the view from all angles. The entire time, just stood there motionless, hanging his head.

I was a little turned on earlier, but now I was out-of-my-mind horny. I had never felt anything close to the thrill I felt feminizing this guy. Every humiliating moment was like a new experience for me in pleasure. I could actually feel my dick throbbing in my boxers. With the new clothing, he was even passable as a girl. I had never even considered doing something sexual with another guy; I'm not gay, but he was so sexy I decided to enjoy myself and take it as far as I could. "So baby," I said, "You're my date for the night. You look so damn sexy."

He started to reply "Very funny...", but I cut him off before he could continue.

"Stop!" I said. "Such a beautiful girl should have a voice to match. Light and airy, you know, not so harsh."

"I'm not a girl" he started to object.

"You are for now. Everything about you is feminine. I don't know your real name, but I'm gonna give you a new one anyway. For the rest of your time here, your name is Amelia. Now..." I continued, "You will speak the way I want you to or I'll send you to jail dressed like you are now and you really won't like the popularity you command in jail.

"OK. Ok." He answered me, trying to keep his voice high and light. He didn't really succeed, he sounded like a bad phone sex girl, but I didn't even care anymore, I was getting off on his humiliation. I felt like I was gonna explode, so I ramped it up to the extreme. I took a seat in the chair and pulled out my cell phone. I started recording a video and gave Amelia the second order for the night.

"All right honey." I said with a mischievous smile, "Number 2: dance. And make it sexy. Take off the top, but leave the skirt and the panties on. I just want to see that sexy bra of yours."

I put on some light jazz music, expecting another round of protests, but Amelia didn't even fight. He immediately started gyrating and moving slowly to the beat. He wasn't very good, but his inexperience and innocence was sexy in its own way. Finally, the top came off and I got a full view of the bra he was wearing. Before I could stop myself, I reached out and groped his ass, enjoying the sensual feel of the sheer material. To my surprise, he reacted with a moan. It was low and barely perceptible, but it was a definite moan. At that point, I motioned for him to come towards me. When he was right in front, I just pointed down and he submissively dropped to his knees in front of me. Fighting to contain the massive orgasm building, I put his hand on my knee and looked down into his eyes.

"Do you know why I named you Amelia?" He shook his head and broke eye contact. "You remind me of a girl I knew in high school. She was the biggest slut in the school. Are you a slut Amelia?"

"N..... No, of course not. I've never done anything like this before."

"Don't lie to me girl. Look at you, you're on your knees in a bra and panties. I can feel your need from here. You're dying to taste my cock aren't you?"

"No. Please don't make me." Amelia looked like he was gonna cry, which of course just made me hornier and ready to go.

"I won't 'make' you do anything. It would be easy to force your mouth down, but I'm not a rapist. No, I'm just trying to bring out your inner sissy. All you have to do is admit that you want it. We both know it's true. Deep down in your heart, you can't wait to wrap those pretty little lips around my cock and you know it. You could have run out this room anytime. I can't follow you; I don't even know your real name. You would be home free, but here you are, on your knees wearing your pretty little bra and panties. I bet they make you feel sexy don't they? They make you feel sexy and turn you on. I know what's going through your mind. You're imagining how it would be. How this cock would feel in your mouth. You want to try it. You want to savor it. I know you do Amelia, so just give in to your inner slut and indulge yourself.

I could feel the hesitation as conflicting feelings fought against each other in this guy's mind. For just a minute, I thought he was gonna end this, but his lack of retreat made me think I still had a shot. Gently, I cupped his face in my hands and pulled him up so we made eye contact.

"Come on Amelia," I said, pulling down my jeans and pulling my manhood out of my underwear, "Just be a good little girl and suck my cock."

That last little bit finally put him over the edge. Without warning, Amelia took my cock into his mouth. No words can describe the ecstasy I was in at that moment. Not only was the physical pleasure off the chart, but the emotional pleasure of knowing that I had broken the last hint of resistance had me about to explode. I started another video on my phone, making sure I was getting a full shot of Amelia sucking me off.

"Do you like that Amelia? Do you like sucking my cock?" I asked

"Mmm-hmmm" was the only answer I got as Amelia didn't even stop sucking long enough to answer. I continued to hold out for as long as I could, but it couldn't have been more than a few minutes before I felt my orgasm building.

"Ooooo yeah, baby. That feels so good. You're so sexy. Do you know what I'm gonna do next?" Amelia didn't reply, I just got a nod of the head and a deep moan.

"Good girl. You're gonna get a nice load of cum now. I want you to swallow every little drop, Do you want that?" A vigorous head nod sent me over the edge and I released, sending one pump of cum after another into my newly christened sissy's hungry mouth. Amelia kept sucking until long after I stopped cumming and then opened up and let it slide out.

Amelia's head rested on my thigh as we made eye contact again. Barely above a whisper, I asked "Did you like it?"

"No...." Amelia said, blushing bright red and dropping refusing to look me in the eyes, "I..... I loved it."

"I knew you would. But stand up; you have one more event before you can leave." Amelia looked confused, but stood up, smoothing the wrinkles out of the dress in the process. I smiled at the feminine behavior.

"Turn around."

"No.... I'm not ready for...." I cut him off before he could get any further.

"Are you kidding? After that blowjob I may need a month before I'd be ready for something like that. I'm not a machine" Amelia blushed again at the implied compliment, but I continued. "No, I don't ever want to be accused of being selfish. I want to make sure you get some pleasure tonight."

With a quick move, I pressed up directly behind and grabbed his cock through the silky panties. The evening's events had obviously worked him up. His own equipment was rock hard and there was a massive wet spot on his dainty underwear.

"Amelia, you're a naughty girl. You enjoyed this humiliation didn't you?" The moan I received back only confirmed my suspicions. After a few moments of intense stroking, I felt Amelia's orgasm begin and savored the trembles and intense moaning accompanying it. Suddenly, Amelia turned to face me and I found myself embraced in the most passionate kiss I had ever received. Amelia broke and looked away, embarrassed, but when we regained eye contact, I gave her a soft kiss on her forehead and let the silence continue. Looking into each other's eyes, I finally spoke, quietly whispering "Thank you for a wonderful date."

::User comments are always appreciated::