tagTranssexuals & CrossdressersMaid The Wrong Bet...

Maid The Wrong Bet...


Part 1

Around the end of my last high school year, my curiosity for crossdressing had just emerged, but I didn't explore the fantasies too much as I thought it was just a phase. The following fantasy is something I have dreamed about for years...

A friend of mine, Peter, was into the same video games as I was, and we made a bet on who would win the next game. We usually played through a network connection, so we each played on our home computer.

That day, he was driving me home. We were talking about the game we played yesterday, and how he thought my win was not really a win, seeing as he was watching a movie at the same time. Arrogantly, Peter proposed we make a bet for the next game.

"What kind of bet?" I asked.

"Depends on how sure you are of winning..." he said.

"Well, I've beaten you a few times and I know your style of playing now, so I'm pretty sure I've got you figured out." I said.

"Well then, if you're *SO SURE*, how about this...if I win, you have to dress up in a French maid costume and clean my room!"

I looked at him in shock... "What? What kind of bet is this?!?"

He looked at me and smiled and said "The kind that you are sure you won't lose!"

I paused and thought about it...why was he asking me to do this? Where did this come from? And most important of all...what kind of outfit was he talking about exactly? Like a sexy outfit or just a plain skirt and shirt kind of thing?

He could see I was hesitant but also considering it. I didn't want to get into this unless I was sure I would win. Then I thought about what I wanted to get if I won. Not if I won...*WHEN* I won.

He then said: "And how about this...if you win, I will give you 500$."

"500$?? Are you serious?" Suddenly, my focus was no longer on what would happen if I lost, but what would happen if I won. That was my first mistake.

"Wow, 500$...I could definitely use the cash...If I win, you pay up 500$, no questions or hesitations?" I asked.

"Yes! Now if you don't think you can win, that's fine, we can just forget about the whole thing..."

"Wait...500$ is a lot...and all I have to do is wear a stupid outfit and clean your room? And if you lose, I make 500$?" I asked, already planning what I was going to do with that 500$.

"That's right, simple as it sounds!" he smiled as he pulled up my driveway. "So do we have a bet?"

Again, my hesitation was obvious. He added: "The game starts at 7pm.."

I looked at him, frowning a bit, then thought of the cash that I could already feel in my wallet...so I muttered "Ok..."

"So it's a deal?" he repeated, wanting to make sure I say a clear yes or no.

"Ok, yes, you have your bet. You're better off stopping at a bank on the way home to take out my 500$..." I said with a smile as I opened the car door.

"Just focus on the game tonight...my room is a mess and it needs a good clean-up..."

"Shut up fool!" I said as I got out of his car. He drove off, and as I walked to my door, I began to feel a nervousness that was slowly overwhelming my insides...I forgot to ask details about the outfit. And that I wanted to specify that no pics or videos were to be taken if I had to be his maid for a few hours. Wow...be his maid for a few hours...suddenly it hit me. I was getting turned on by the idea. My limp cock was slowly developing into a raging hard-on. Did I want this to happen? No, of course not! Why would I? Why would I want to try on a French maid outfit, and why would I want to do that in front of him?? The more I thought about it, the harder my dick got. Once I made my way to my room, I had to jerk off. I was too horny at the thought of having to dress up as a French maid for another man.

It was now 5pm, time for dinner. As I prepared the meal with my parents, I could not stop thinking about dressing up as a maid. The thought of being dressed up was the biggest turn on. This was not good. I had to win. I wanted that cash. Not his cock!

WAIT...why did I just think that?? How did Peter's cock become a part of these thoughts? This was not part of the bet! I'm straight...it just so happens that I have a thing for lingerie, and always thought the French maid costume was so erotic, but never did I think it would be erotic if "I" wore it.

Dinner was boring, and I eventually made my way up to my room to load up the game and connect. My hard-on had faded away during dinner, but now it was back as the connection was established.

Ok, it's do or die now...


Part 2

The game had gone well...at least the first half of it. But then, gradually, I was losing. No, I was being destroyed. I had come-backs and hopes of winning, but the closer we got to the end, my thoughts were drawn away from the game and images of me, dressed in a sexy maid outfit, kept clicking one by one in my mind. I pictured myself on my knees in that outfit, and my dick was as hard as it could get.

The downward spiral of shame, fear and nervousness became stronger and stronger...I had lost the game. Holy shit, I HAD LOST THE GAME. Bye bye 500$...but somehow, the money was no longer important. I had lost, and now I had to pay up. I had to go clean my friend's room dressed in a slutty outfit.

WAIT! No one said anything about a slutty outfit. It'll probably be a makeshift outfit made from various pieces of women's clothing he can get his hands on. He has a hot sister, and she's approximately my height, but she doesn't dress slutty, so she most likely doesn't own a maid's outfit. Maybe all of this is just my imagination playing tricks on me, and all he'll really want is for me to clean his room. Wait...is this disappointment I am feeling? Why oh WHY would I feel disappointed if he doesn't take advantage of me? Why was I thinking about him taking advantage of me? AND WHY did I still have a hard-on???

My cell phone rang...it was Peter. I didn't want to answer, but at the third ring, a part of me guided my hand to the phone and I took the call.

At first, I just clicked to answer and listened...and after a few seconds, I said: "Yes?"

"Sooooo...looks like I'll be sleeping in a clean room tomorrow night!" he gloated, arrogantly. I did not know what to say...what could I say?

A part of me felt shame and humiliation, but another part of me fed blood to my cock and kept reminding me that I was going to be dressing up as a maid. I didn't know which part to listen to, so all I could mutter was "I guess so..."

"That's right you guess so", he said a bit more aggressively, "because if you back out, I'll be telling everyone in class that you had agreed to this bet!!"

More humiliation crept up inside me...no, this I could NOT allow. As I looked down at my rock hard pushing through my jeans, and again with hesitation, I responded: "... a bet is a bet, right?"

"Good, glad to hear it. Tomorrow after school, I'll be driving us to my place, and I'll have everything ready."

What did he mean by "everything ready"? "Ok..." I responded, and he hung up.

Needless to say, my lust was overwhelming me again and I had to jerk off to tame my lust. I went to bed and had trouble sleeping, as images of me in a sexy outfit raced through my mind.


Part 3

For the first time in my life, I wished a school day would not end so fast. I wanted the day to last forever, because my fear of the unknown after school kept my mind paralyzed and filled with shame. Fortunately, I was able to hide the shame and shock, especially since Peter did not have any classes with me during this trimester. I don't know what I would have done or how I would have acted if he had been in one of my classes.

The final bell rang, signaling the end of the day. The shame in me was rolling at maximum level as I walked towards the parking lot and spotted his car. I noticed he was sitting in his car, ready to go. I avoided eye contact and got in on the passenger side.

He asked: "Are you ready?" Ready for what? The most humiliating moment of my life thus far? Of course not!

"Let's just get this over with..." I snapped, feeling anger and frustration. He drove off, and the rest of the ride was dead silent. Again, the feeling of wanting to slow down time came back as I realized he didn't live that far and we were getting close to his place. Still...my cock was getting hard at the thought of being moments away from dressing up. Oh oh...my hard cock...what happens if I get hard while dressed up? Will he notice it? Shit, I had not thought of this until now...

He slowed down and turned into his driveway. I looked at him for the first time since I got in the car, and noticed he had a half-smile. Shit, he was enjoying this. He was enjoying my loss, my humiliation and my shame. Somehow, it reinforced my erection...

As he got out of the car, I realized I also had to get out, so without saying a word, I got out and followed him inside. No one was home. GOOD. That would have made things even more awkward, considering I had not even thought about that aspect of my problem until now. At least this will stay between me and him...

I took off my sneakers and followed him up to his room. He opened the door and I was stunned...his room was a freaking mess! Did he mess it up on purpose, to keep me here longer? As I pondered on this, my gaze was drawn to his bed...my heart stopped for a few seconds and a wave of extreme shame vibrated through me as I noticed what was on the bed.

The maid's outfit. Not just any maid's outfit. A sexy one. The kind of outfit that would turn me on if it were featured in a porn movie. A silky, black dress, cut very short, with a white lace trim around each opening. The white lace apron, laid out on the dress. The black lycra thong. The black stay-up stockings with lace trim. And the black high heels. And a black wig.

At this point, it was like I was on auto-pilot. He walked in to his room, turned around and pointed at the bed. I didn't say a word, and I slowly walked over to the bed and started picking up each item. Why was I just going ahead with this? My hard-on. Why was I not questioning this, not fighting that I didn't have to wear the intimates or the wig or the shoes. I could argue that I had agreed to wearing the dress, but not that I had to take off the rest of my clothes. But I didn't argue. I didn't fight. I didn't resist. I just...accepted. As I picked up each piece of clothing or accessory, I felt a lust build up inside me. I wanted to wear this. I had to.

As I picked up the last piece, the shoes, I made my way to the bathroom. Not once making eye contact. I got in the bathroom, and closed the door. I locked it. Then I double-checked to see if it was really locked.

I dropped everything lightly on the floor. Where did he get this outfit?? Did he buy this?? I guess if he had 500$ to waste on a bet, he must be well off, or at least his parents are well off. Still driven by my lust, I started removing my jeans and shirt. Then my socks, then my underwear. Wow. Here is was, in Peter's bathroom, completely naked, and about to dress up in sexy lingerie. My dick was hard! I wanted to stroke it, but a part of me wanted to get this over as soon as possible, so I picked up the dress.

Not having any experience with women's clothing, I had to figure out how to put it on. I noticed a short zipper in the back, so I pulled it down and realized I could put it on by stepping in it. As I raised the dress higher and higher, the silky fabric caressed softly my skin. I was in heaven. I didn't want to face it, but I was hornier than I had ever been. As the dress made its way to the top, I guided each arm into its respective very short sleeve. I looked down, and the dress was way too short...it barely covered an inch below my ass. The front was tented due to my hard erection, which made me feel both ashamed and horny simultaneously. In fact, the stronger the feelings of shame and humiliation were, the hornier I got. I did not realize this until just now. Does this mean I enjoy sexually to be humiliated?

I was in a trance. I picked up the stockings, and figured out how to put them on. Wow. It was like my mind was changing, morphing into a different point of view. As each stocking eased up my leg, the lust in me was boiling. I had precum drops leaking from the tip of my rod, and the vibrating wave of shame I was feeling in my body was slowly being turning into a vibrating wave of sensuality and lust. I had to get sexual relief. I had to. I needed it. I picked up the wig and put it on, and looked at myself in the mirror. I was hot. I was not only feeling the lust, but I looked hot. I had some curves that made me look ladylike, and it was driving me wild. How come I had not noticed this about me. My butt cheeks were round and looked terrific in the dress. I then grabbed the thong and slipped it on. Oh. My. God. This was turning me on even more. When the thong reached my crotch, I realized that I had to arrange the thong. I covered up my cock and balls, but due to my raging hard-on, the fabric could not cover my balls. So I left the thong as is, and looked at myself in the mirror. My cock was tenting the thong and it barely covered my crotch area. But at this point, I did not care. I felt like I was someone new. Something had changed in me when I put on this outfit, and I was no longer worried about shame and humiliation. I was now worried that I would not get sexual release...

In a hurry, I grabbed the shoes and put them on. Wow, they fit. How did he know my size? In fact, how come everything seems to fit perfectly? Did he plan this ahead of time? Did he cheat at the game?? I thought about these questions, but I didn't care about the answer. I looked at myself in the mirror, and arranged my dress to look proper. I wanted to look proper. My erection was kind of showing, but I still wanted to look proper for Peter. Proper enough to look attractive. To look seductive. To earn his cock... this thought was no longer an issue with me...the thought of his cock was now an objective instead of a feeling to resist. I had accepted it, and now I needed to show I deserve it.

I grabbed the door knob, unlocked the door, and thought... "it's show time..."


Part 4

I opened the door slowly, and with my first step, I tripped and almost twisted my ankle. I held on to the door to catch my fall. Shit, I'm not used to wearing slutty shoes! I stood up again, and focused on my balance as I started walking out of the bathroom. Click. Clack. Click. Clack. The sound of my shoes (yes, they were now MY shoes) resonated across the hall, and I thought that this would surely announce that I was ready to begin. Begin what? I didn't know, and I didn't care. I just wanted to "begin". So I made my way to his room, and pushed open the door.

He was sitting at his computer and slowly turned around. His jaw dropped for a second, but then he immediately put on a straight face and said "Good, you can start with my clothes, put the dirty stuff here and fold the pile that I just dumped on the bed."

"Yes Master." What did I just say? I called him Master? Why would I do that?? His face changed again and his smile was more than obvious. He had me, and he knew it.

"Good. Get on with it!" he said with more authority. I walked over to the bed, slowly to ensure that I kept my balance, and picked up a shirt and started folding it. As I continued my chore, I glanced over at him and he was staring at me. Not just looking here and there while doing something else. He had clearly stopped what he was doing and was directing his full attention to me. I decided to improvise a little. The next shirt I picked up, I dropped it. "oops..." and I bent over to pick it up quickly. I did this to show him my cute little butt. Yes, it wasn't my manly ass anymore, it was my cute little butt. To show him that I had accepted my faith and that I was his to use.

As I continued folding the clothes, he got up and walked by me to go to his dresser and he opened the top drawer. "Come here" he commanded. I walked up next to him.

"This is where my boxers go" and closed the drawer. "Open the next one." I opened it, slightly having to bend to reach it. "This is where my socks go" he said. I nodded and said in almost a whisper "yes Master". I closed it, and opened the one below. This time, I made sure my legs were straight and that my entire upper half was bending over. As I opened it, I backed up and lightly touched my butt against his leg. "That's where my short sleeve shirts go" he indicated, smiling. I nodded, and bent to close it. This time, he had moved closer and as I bent down, I could feel my butt touch between his hip and his crotch. I bent some more to reach for the last drawer, and felt something pressing against my butt. It was hard and vertical. A shiver ran through me as I realized it had to be his hard cock. I let out a tiny moan and pushed back slightly as I raised myself back up to stand behind him.

"That's where my pants go" he said softly behind me, as I felt his erection once more touched lightly my left butt cheek. I whispered "Yes Master" and slowly bent down to close the drawer. As I bent down, I readjusted myself so that his erection would line up with my butt crack and I innocently backed my butt cheeks against his erection as I reached the bottom drawer and slowly closed it. I could feel him push and bump lightly his erection against my asscrack. The feeling was so intense that I stayed in this position for a few extra seconds and closed my eyes and let him grind his cock in my butt crack before I slowly got up.

There was tension in the air now. Lots of it. We both knew where this was going, but no one wanted to admit it or act on it. He then returned to his computer, sat down and said "Ok I gotta check my email and take a shower, I have basketball practice after dinner." Left in limbo, I sadly returned to the bed, and continued folding his clothes. My throbbing erection needed some relief, but there was something else that I needed. Something I needed more than an orgasm. I needed to see his dick. I needed to feel his rock hard erection in my hand. In my mouth. Yes. In my mouth.

As I continued folding his clothes, which I was almost done doing, he got up and walked out to the bathroom. I need him. I need his cock. I want it and I'll get it. Then I noticed his clothes on the floor. It gave me an idea.

I heard the water running in the shower, so I hurried up with the folding. A few minutes and I was done. I quickly put away his clothes and was free to take care of all those clothes on the floor. I walked up to the pile and kneeled down. The moment my knees touched the floor, I felt a squeeze in my loin, and some precum leak out. I was at my place. Dressed in a slutty French maid outfit, on my knees, this was bliss to me. I grabbed my hard cock and started stroking it slowly, and more precum came out. I reached out with my right index finger and caught the tiny glob of cum. I raised my hand to look at it, and out of lust I brought it to my mouth. I licked my finger clean, and tasted the saltiness of the precum. This was my first time tasting cum. I could feel the thickness of the liquid on my tongue. There wasn't enough to swallow, but I still had the reflex to do it.

I heard the shower stop, and slowly came to my senses. Here I was, kneeling in his room, dressed as a slutty maid, and I had just licked off a glob of my cum. I needed more, but I had to make it happen. I repositioned myself on my hands and knees, with my cute butt pointing at the doorway, and pretended to be making separate piles for dark colors and light colors. I began humming very lightly a random tune, to show I was engrossed in my work.

I heard steps approaching the room, and the squeak of the door as the hinges betrayed the opening of the door. From his angle, he would be able to see my hole...no...my boipussy. Yes, he would spot my boipussy because the dress was too short to cover anything.

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byLea1234© 17 comments/ 148171 views/ 168 favorites

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