Becoming the Sissy Slut

Story 5

"You are going to have to go, I don't see a choice here." My boss said to me.

I didn't want to go on this trip. It was a routine check of one of our automated sites. That meant about 10 days of living in a hotel and checking in to the control room once a day just to see how the automated diagnostics were going. Normally, we send Gary, the junior staff member, but he had just gotten married and was away on his honeymoon for the next 3 weeks.

"I understand," I replied, "but it seems like such a waste to fly all the way out to Oklahoma just to check a console once a day". I was doing what I could to causally get my boss to see the money the company was wasting by sending me.

"Sorry Neil. Upper management has eyes on this since we've had 3 sites go offline this month. I need my best man on this. No screw ups." He said as he hung up the phone.

Damn, I thought to myself. What am I going to do for 10 days in the middle of nowhere? It's not like this tiny town will have any entertainment. I'd be surprised if there is even a bar. I picked up my phone and started to look for a hotel. The nearest one was over 100 miles away. I didn't want to spend 4 hours a day driving through the back country of Oklahoma, so I expanded my search to include room rentals and AirBnB sites. Bingo! There is an AirBnB just 5 miles away. This was the description:

AirBnB: Single bedroom, private entrance 1 bathroom. 850 sq ft. Kitchenette with microwave and sink. Special accommodations available.

Ok, perfect! I booked it on the spot and began to make all of the accommodations for my trip including airfare and car rental. I downloaded a few movies to my iPad to watch in case there was no wifi service and bought a few books. From my search it looked like the nearest "town" if you can call it that was about 20 minutes away, so not terrible if there is a restaurant there.

The trip

The flight and the car rental were uneventful, and I arrived at the AirBnB by 10PM on Saturday. As I pulled up to the address, I noted it didn't look anything like the pictures. This seemed like an average house. I couldn't see the "private entrance". It was late and after about 2 minutes of confirming the address, I went to the door. The guy who answered the door was big. Probably 2" taller than me, and fairly muscular.

Just to set the stage, I'm not gay, but I have had a few experiences with guys throughout the years, and really enjoyed them. The closest thing to a relationship with a guy was a friends with benefits situation a few years back with a neighbor who was regularly coming by. His wife thought he was coming over to help me with something, or to borrow or return something. In reality, I was blowing him, or he was stroking me. I always imagined going further with him, but it never happened.

Jeff, the owner was a handsome man, in his late 40s with a military cut hairstyle. He was wearing tight T-shirt and grey sweatpants.

"Hello," said Jeff, "You must be Neil. I expected you earlier than this."

I replied "Hi Jeff, yes, I'm Neil. I'm sorry to arrive so late. There were delays at the airport. I tried to call you, but my phone service was non-existent driving out here."

"That's ok. Let me show you to your room." And with that he stepped back into the house.

I followed him in and said "Ok, thanks. I thought the room had a private entrance?"

"It does, but it is easier to go through, if that doesn't bother you" Jeff said over his shoulder.

I followed him in, closing the door behind me. It was a nice home, decorated stylishly. Whatever Jeff does for a living, he must be doing pretty well for himself. After a walk down the main hallway, he opened a door to the basement and started down. I've seen enough horror movies in my life to hesitate here, but it seemed well lit and furnished. I conceded that it is possible that the AirBnB is in the basement apartment with a walk-out. I followed him down, leaving the door open behind me in case I needed to make a speedy exit. We walked into a lavishly furnished apartment. He showed me around, pointing out the kitchen, bathroom and bedroom. Everything was clearly in a girl's taste though. The bedspread was pink and frilly, and there were female touches on the furniture and a makeup case and perfume on the dresser.

"I'll let you get settled in." He said as he started back towards the stairs. "If you need anything, just ring the bell down here and I will hear it upstairs and come down."

I dropped my suitcase and my equipment bag in the corner of the bedroom and went to put my stuff away. Opening the closet, it was filled with women's clothing such as dresses, skirts, and some skimpy outfits that anyone over the age of 20 would be ashamed to be seen in. I made some room and hung up my pants and shirts at the end. I then opened the dresser and found it too was filled with women's clothing, such as g-strings, lace panties, bras, stockings and lingerie. I pulled some of it out and looked at it. It was good quality, and clean. Clearly this is his daughter's apartment. She must be away or have moved out. I left the rest of my clothes in the suitcase for now and flopped down on the bed.

As soon as my head hit the soft pillow, I was fast asleep. It was a long day. My night was filled with dreams of trying on the clothing and looking at myself in the mirror. I woke up a little disturbed from these as that isn't something I've ever done. I got up, and went to take a shower, and as I have come to expect, all of the soaps and shampoos are scented and intended for a woman. I used it for lack of a better choice, dried off and stepped out to get dressed.

As I reached into my suitcase, I realized my clothes were gone. Did I put them away? I checked the drawers and found only the women's clothing. I opened the closet and found those were gone too. What the hell is going on? I tied my towel a little tighter and rang the bell for Jeff.

After a few minutes, he came downstairs and said "Hey Neil. Everything ok?" I noticed he was eying my towel and my body. I felt like he was undressing me with his eyes, imagining what was under the towel. I said "Um, not really. All of my clothes are missing. I put some of them away last night, and now everything is gone."

He took a step closer to me, now less than a foot away, and it was clear what was going on here. This guy is a predator! I debated what I could do, naked with only a towel against this muscular guy and realized my chances of escape were slim. He must have seen the panic on my face, because he said "Don't worry, you aren't in danger. I was hoping you might... well... see things my way."

"W..w..what does that mean?" I stammered trying not to sound afraid.

"Here's the deal," he said as he put his hand on my shoulder. "I knew the moment I saw you, that you would be perfect, and I am willing to be very discrete. I was hoping that if you were into it, maybe you could put on the clothes in here, and we could have some fun. If you are willing, I will not only let you stay here for free, but I also promise it will change you in ways you couldn't imagine." And with that last sentence, his hand slid down my chest towards the towel. I have to admit, part of me was turned on, feeling so vulnerable in this moment, and that made me want to please him. In a way, I felt like this could be a fun experiment while I was wasting time here in town each day.

"Ok..." I gulped, nervously "but I will want my clothes back."

"Yes, I thought you might. And for now, indulge me and you can have them back." He said. He turned around and started to walk upstairs. He said from the top of the stairs "I'll give you 10 minutes to get ready, and I will come back"

My first venture

Not knowing what else to do and being a little turned on by this taboo act, I pulled open the drawer and started looking at the underwear. I chose a pair of cotton panties instead of the lacy panties and stuffed my cock into them. They felt pretty good, and now my hardening cock is poking through the top. I opened the closet and chose a dress that came down to my thighs and slipped it on. It fit perfectly. I looked at myself in the mirror and I looked ridiculous. A man in a dress. But maybe this was enough to get things going, and eventually I can get my clothes back.

In a few minutes Jeff came back downstairs and saw me sitting on the bed. He smirked a bit and said "I can see it all fits, but we will have to do better. Can you stand up and turn for me?"

I stood up and turned in a slow circle, the dress swishing around my legs. Jeff walked over to me and stood right in front of me. He slid his hands down my back, and squeezed my ass a bit, which made my cock jump a little. I put my hands on his sides, and he brought his back up to my shoulders, apply a gentle but firm pressure. He wanted me to go down on him while I was dressed this way! Clearly my cock thought this was a good idea, and I was turned on, so I complied and went to my knees in front of him. I unzipped his pants, and started to pull out his cock, but he caught my wrist before I could and said "No... Not yet. I want to make sure you really want it."

"I do....." I replied, looking up at him and then I added "...sir" Was I hopeful? Did I really want this? I did. I wanted to see his cock. What was happening to me?

He took a step backwards from me and said "Then let's do it right. I want you to shave yourself smooth before tonight. Everything. Arms, legs, armpits, cock and balls, and ass. You can wear that dress today, but we can talk about your clothes tomorrow." He zipped up his pants and said "And... you are forbidden from jerking off. I want you desperate for it." He left and went upstairs again.

I considered taking off the dress but then since I had no other clothes, I would be totally nude, or just wearing panties. I sat on the bed and watched some TV for a while, my mind wandering over what transpired and what might still transpire. I got up and looked myself again in the mirror and conceded that I would be "improved" if I did what Jeff asked, so I got in the shower and started shaving.

After a good 45 minutes of grooming, I was finally hair free. I had a few nicks on my ankle from the razer and some razor burn above my cock, but I felt a little freer. I could feel a lot of the cool air moving across my body. When I put on the panties again and the dress, it was a totally different feeling. I started to feel more girly and this was exciting. I looked at myself again from different angles and my bulge was very noticeable under the dress. I started to rub and stroke it through the panties, running my hand across the fabric. It felt so good, I felt like I was going to cum. I tried to stop, but I was past the point of no return and I accidentally ruined my own orgasm, my cock shooting cum into the inside of the dress and leaking all over the panties.

I changed into a different dress and panties leaving the soiled ones to the side. Jeff might be upset, but he will understand. A few hours later, Jeff came back down with lunch for us and noticed two things immediately. One, I had changed, and two, the dress and panties in the corner had cum stains on them.

"I told you not to touch yourself" he said, choking back a little frustration.

"I know, and I'm sorry. I was just admiring myself and I got carried away. Don't be mad though, there will be more than enough toni..." I was saying.

"Oh, I know." He interrupted me walking to the cabinet in the bathroom. "But to be sure you don't have any more accidents; I want you to wear this." He pulled out a chastity cage.

"I don't need that, really." I lied. I knew if given a chance I would probably touch myself again.

"You do. Both for your 'accidents', and to make you look more feminine. We can't have a bulge in your dress if you are a proper sissy." That last word hung in the air between us. This was more than I signed up for. I wanted to back out, but this man had my clothes, and there was something inside me wanting this.

I pulled down my panties at his request, and almost clinically, he placed the cage around my cock and balls and closed it with a small padlock. With the sound of the lock closing, it dawned on me that I was going to let this man fuck my ass. I hadn't been a bottom before in my other encounters, but I have played with my own ass with toys plenty of times.

He stepped back to take a look at me and said "That's better. Let's have some lunch." We sat down in the kitchenette and ate the sandwiches he brought down. I felt like he was studying me while I ate. Was I eating too 'manly'? A part of me wanted to play the part. I tried to act more feminine to please him, to make this more real. What was happening to me?

After lunch, he cleaned up the plates, and said he would be back this evening and I should be "ready", and that I still had a long way to go.

After he left, I examined the cage on my cock, trying to slip it off, but it wouldn't budge. I thought about what he said and wondered if he was going to fuck me. I knelt on the bed, looking back over my shoulder at the mirror, looking at my ass in the dress. I pulled up the dress, and then pulled aside my panties to look at my cute ass, spreading my cheeks to look at my pink hole. I ran my finger over it, exciting myself, and at the same time causing excruciating pain at my restrained cock. Trying to forget it, I pulled my panties back up and sat down to watch TV.

Bored with sitcom reruns, I started looking at the DVDs that were stacked under the TV cart and noticed some that didn't have labels. Curious, I put one in the player and sat back while it started. It was a sissy hypo video. Images and music of girls and sissies sucking cocks, eating cum, getting fucked, while the words subliminally had messages like "You want to suck", or "Your place is to please". After about 3 minutes or so, I dozed off with it playing. When I woke up, it was already 5PM. I realized I had to hurry to be ready, and I wanted to be ready!

I looked at myself in the mirror over the dresser, and realized I still look like a guy wearing a dress. I looked through the makeup and found eye liner, lipstick, blush, eye shadow, and mascara. I wanted to see how I looked, so I started putting it on. Since I haven't done it before, it took several tries to get it looking decent. Finally, I put on the red lipstick and looked at myself again. Better. Not passable, but definitely better. I polished my fingernails, last and let them dry. Why was I doing all of this? I was basically dressed up in drag? At the same time, I was secretly hoping he liked it.

At around 7:00PM, Jeff came back down, dressed very nicely, smelling like old spice and he brought some dinner with him. He put it on the table and looked at me expectantly. I didn't know what he was waiting for. Did I look ok? Did I do something wrong? I realized he was waiting for me to set the table. I moved to the kitchenette, and pulled out two dishes, silverware and napkins. After I set the table, he opened a beer for himself, and a bottle of white wine for me, and then he lit a candle and put it on the table. Was I on a date? With a guy? While I am dressed as a woman? An almost passable woman at this point, with a few exceptions.

"I'm glad you decided to go the extra mile for me." he started

I replied "Yes, well, if we are doing this, we might as well do it right. Do I look ok?" I wanted to choke on the words after they left my mouth. Did I really just ask that? Like some teenage girl?

He grunted as a reply as he started to eat his food. It was delicious, and I was careful to use my fork and knife and take small bites. I was too nervous to really be hungry. What I was hungry for was across the table from me.

After dinner, I told him "Before we go too far with this, I will need my clothes back tomorrow. I have to drive to the site and do some work."

"Oh? Where?" he asked

I realized my mistake in that moment. The site was automated. I didn't have a good reason to get my clothes back. As I was thinking it, he said "Maybe you should go as a woman. You said you've never been here before, so no one knows you."

"Everyone who looks at me will see a freak in a dress, not a woman." I said.

"We can fix that, but we will see if you earn back your clothes tonight." He replied.

We moved to the bedroom as the bed was the only place to sit other than the kitchen. He noticed the DVD case for the movie I had in and didn't say anything, he just smiled. He stood up right in front of me, his crotch 6" from my face and asked, "What is your name?"

I was confused. He knew my name.

"Um... Neil?" I said.

He raised his hand as to slap me but stopped. "WRONG. This is your only warning young woman!" and then it clicked.

"VICKY! My name is Vicky, sir" I said quickly coming up with a name.

He lowered his hand and ran his fingers through my hair. I wondered if my hair was too short? Would I be more attractive if I had a wig? I placed my hands on his thighs, licked my lips, and looked up at him and asked, "May I ....may I please play with your cock?"

"You may..." He said, and I began to unzip his pants. This time, I took my time, undoing the button and his belt to pull his pants down a bit. He was wearing boxer briefs, and for some reason, I wanted to smell him. I leaned in, burying my nose near his cock, inhaling it. It smelled so manly. I kissed around his semi hard cock through his underwear, before pulling them down. His cock flopped out, and it was big. Big enough to scare me. Immediately I thought I would have a hard time sucking it and dismissed the idea of letting him fuck me. I stroked it gently, feeling the soft skin get firm in my hand, and then I kissed and licked it from the balls up to the tip. I could tell his breathing was getting faster, and my own cock was straining in the cage, causing me discomfort. With my free hand, I tried to adjust it, and he slapped my face.

"Don't do that!" he said firmly.

"I'm sorry, it's just that my dick is uncomfortable" I said meekly, not trying to lose the mood.

"It's not a dick anymore, VICKY. It is your clitty. You can only refer to it that way. Do we understand each other?"

I didn't want to answer. I tried to go back to licking and sucking his cock, but he pulled me away by my hair, looking at me in the eyes, and said "DO.WE.UNDERSTAND.EACH.OTHER.SISSY?"

I wanted to get up, to leave. I wanted to fight back, but how? Where would I go? I'm dressed as a woman, I have no other clothes, and Jeff can easily overpower me. I said, "Yes sir." Meekly. "I won't touch my ... citty." The words were hard to get out.

He gently pulled my head back towards his cock again. As I started to suck it again, he said softly "...good girl..." I wanted to smile a little. Was I being a good girl? What's happening? Why am I happy about being called a girl? But I wanted to please him, so I did my best to suck him. I made it wet and took as much into my throat as I could, coughing up a little extra spit and saliva. I used my hand on the base of his shaft, stroking it with how wet I made it, while sucking and licking. He was groaning now, forcing my head further and further on to it, and I knew he was going to cum. I pulled back a little and looked up at him, stroking his cock faster and he began to growl/scream and he shot load after load of hot cum all over my face. I opened my mouth to catch as much as I could, swirling it on my tongue while milking this fat cock on my face. After it was over, I gently sucked his deflating cock to clean it, and tucked it back in to his pants. His cum was delicious. I felt so naughty, but so right. I used my fingers to scoop globs of cum on my face into my mouth, sucking on my fingers.

"Vicky, that was very good. I hope you sleep well." And then he turned around and walked back upstairs. I wanted to ask, "What about me?" but clearly it wasn't my place anymore.