Adam Loses a Bet Ch. 03

Wednesday morning, I woke up cuddling a pillow. I was feeling a little more at home in my hopelessly pink room. When I walked over to the full-sized mirror, I noticed I still had my lip gloss and blush on. "aaahhh," I gently screamed. I'm glad I didn't see my mom or sister last night, that would have been embarrassing. I quickly wiped it off. Other than that, my day started completely normal, which felt strange. I felt like a different person in a way. My first three classes flew by; one moment I was sitting down for school, the next I was going to my last class. Biology was never my favorite, but the class was mainly girls, so I never complained. There was a cheer meet today, so three girls came to class wearing their uniforms. Amy was one of them.

She sat next to me. She was dressed to the nines; I think every guy was stealing glances her way. I tried to avoid eye contact and just looked for the teacher, but I couldn't see her anywhere. Where was the teacher? Our class was both confused and relieved. We just started talking.

This is when the magic happened; every horrible day in biology was worth it because of the next 20 minutes. Amy turned towards me and started talking. At first, I was thrown off guard by her classic red hair, green eye combo. Not to mention her current ensemble, but I quickly got over that. We had a smooth, awkward moments free conversation about everything and anything. Sometimes when she talked, I would admire her cheerleading makeup. The cute pink eye shadow with thick mascara really brought out her eyes. The rose lipstick she used looked delicious. Everything from her smooth foundation to her contouring was perfect. My train of thought was completely thrown off by a compliment. "I love your hair! How do you get it so smooth? Mine will never be settled." Amy inquired.

"Oh, uh. You know, conditioner and stuff."

"I need your conditioner."

"It's just the generic dollar store kind."

"Noted. I love when guys have longer hair. I think it shows a little femininity... in a good way."

"Oh, thanks."

"Can I braid it?" At this point she could've asked me to jump off a cliff. I quickly agreed and turned around. She started trying out a couple different braid patterns trying to find her favorite while talking about her brothers, and how she wished they had a feminine side. Better yet, she wished she had a sister. After that she paused in thought, giving me an internal panic attack. Everything was going so well; an awkward silence would kill the perfect conversation. Then she said it. The magic words every guy in love wants to hear. "We should totally hang out sometime." Of course, I agreed and we both traded numbers and followed each other on Instagram and Snap Chat. It was probably the most exciting 30 seconds of my life. Shortly after, a substitute teacher walked in and pretended to know biology. Amy and I told each other snide comments and jokes about him the whole time. The bell rung too soon, and I drove home in the rain.

I had forgotten about going straight to David's, and about what I was supposed to do there. I was on an unstoppable high; nothing could ruin this mood. Although that didn't stop the universe from trying. Less than a mile from my house my car stalled, and the check engine light went on. After a few tries to start it up, I determined it was hopeless. I called Bryan for a ride and I did what any man would do, I looked under the hood and pretended to know how a car works. My hair was wet and still braided, however, I was still in too good of mood to stop smiling. 10 minutes later Bryan pulled up. "Hey baby girl! What's a cute thing like you doing out here?"

"Oooh shut up, I'm so happy right now not even you could bring me down."

"Don't you challenge me, I'll win." I rolled my eyes and got in his car. I would talk to my mom tomorrow about what to do about the car. Bryan offered to give me a ride to and from school until it was fixed.

When we pulled up to David's I could only think about Amy. I pulled up her Instagram and mindlessly scrolled until I was shoved in a bathroom. "You know the drill," Drew yelled through the door. I looked down and saw a French maid outfit, complete with feather duster. After stripping I got dressed like it was completely normal. The white lace panties and matching bra gave me a weird tingling feeling. When I looked for water balloons, I was disappointed to find actual breast forms. Was that taking it too far? I don't know. After looking at the instructions carefully, I glued them in place and slipped the bra back on. I saw a tin of concealer next to the instructions. I reached down and applied a generous amount to hide the line between the silicon breasts and my skin. After the glue dried and I finished up my rough make up job I admired my work. Dang. Those looked real. Grabbing and moving them felt real, shaking them moved my chest in consequence. My nipples could feel every light touch to the silicon weights. I played with them for a hot second before I moved on to the dress.

I stepped into the delicate fabric and zipped up the side. It barely covered the bra: it showed off a lot of my new cleavage. The white fabric on the top was silk and was held together by a big bow right in the middle of my chest. The middle was black and looked like the top of a converse; It had white silk ribbon tied like shoelaces across the small of my back.

The skirt barely covered 1/3rd of my thigh and really gave me the illusion of a ballerina body. Noticing long silk gloves, I put those on next. They made my hands look even slimmer and felt amazing. I turned to the white lace stockings and slipped them up my smooth legs. They came halfway up my thigh and had a bow on the top. I tied my hair up again and pulled out two sections of hair to frame my face. Since my hair was braided and wet before this, I had a wavy ponytail with two spirals that delicately fell on either side of my face. I slipped the black and white lace head band over my head. I was in such a good mood that I didn't even care that there was a big white bow on it.

I dug deep into the drawers to apply some lip gloss and a little blush. While searching for that I also found some liquid mascara. I remembered how hot Amy looked today with her makeup and thought, why not? So, I applied a generous coat and finished the look. A black and white lace chocker with the name Amy on it finished the job. Looking back at myself was trippy. I didn't even recognize who was staring back at me. I grinned and licked my lips. Even I had to admit, I'd hit that. Leaning in, I noticed how smooth her skin was. Her ample C-cups and erotic outfit captivated my attention and drew me closer. Her glossy lips looked delicious and her breathe bouncing off the mirror was hot. I leaned in for a kiss. Upon contact I introduced my tongue and got lost in the moment. Gently opening my eyes, I saw a sexy French maid making out with me. I was Frenching a French.

*knock knock* My fantasy was interrupted by a rap on the door. Drew prompted, "You about done Amy?"

"Almost, one sec!" I grabbed a towel and wiped off the mirror. After touching up the lip gloss and concealer I unlocked the door. The door opened and I walked out to a stunned version of Drew. "Dang girl, your convincing as heck."

"Shut up, don't you go gay for me." I walked past him towards the basement. *slap!* Andrew spanked me! Bare hand to my pantied butt. Sure, it was gentle, but still, What the heck! I chose to pretend it never happened. We both walked down to the basement and I was greeted with cat calls and applause. David walked over to me and told me to turn around. When I did, he pulled the silk ribbon on the back. *gasp* I took a quick breath. I didn't know there was a built-in corset, let alone how tight they feel. He continued to pull the ribbon until I had a super small waist and no room to breathe. After finishing with an expertly tied bow David also gave me a light spank under the skirt. "That's a little too much, don't you think?" I objected.

"Not at all, you look hot." I blushed a deep shade of pink. "Don't be gay David, I'm just doing this for the bet."

"I know." He winked before returning to his seat at the table.

Drew couldn't stop staring at my chest. "I can't even tell they're fake," he said in unbelief. He walked over and poked them. Then he squeezed one, then he grabbed both and started kneading, rubbing, and bouncing my chest. I just kind of... awkwardly stood there. What do you do in that position? The breasts weren't even technically mine. I just ignored him and watched David bring in bags and bags of food. Eventually I just walked away, leaving a disappointed drew behind me.

Surprisingly, we weren't in front of a T.V. today. Instead I was urged towards a large table just off to the side. There was a load of random stuff. Half of which was food. David explained, "Since you and Bryan came late, let me catch you up. Andrew and I were eating some unmarked leftovers in the fridge. We were debating what the food was. Either way it was good, but our argument got heated. Andrew bet me that he had better taste. So that's what we're going to do. Y'all can join to.

"That sounds dope, we're in." Chimed Bryan. Funny how he didn't even ask me. So, we figured out the rules and began. Andrew was up first. He closed his eyes and David put a spoon in his mouth. "Oatmeal with brown sugar," answered Andrew.

"Correct," David admitted.

We followed a similar pattern for bananas with sriracha, peanut butter with cranberry, and expired Cheetos and garlic. Once scores were practically tied up, we moved to tasting non-edibles. Andrew licked a shoe, a golf ball, and an old jersey. David had nearly gagged for all three of his while Bryan was both unfazed and always right. I had eaten dried black licorice, pickled jalapenos with grape jelly, and apple juice and milk. I guessed them all wrong... However, every inanimate object I guessed right. My trick was to put a little of the object in my mouth so I could feel the shape. I tasted the bottom of a kitchen chair, the hair from a comb, and an old light bulb.

David was up by one on Andrew. We were laughing so hard each round, I nearly forgot what I was wearing.

We determined a lightning round would determine the winner of the bet. "Hold up. The bets between you and Drew. Why do we have to lick all these horrible things?" Bryan complained.

After a second of thought, David thought of an incentive to keep everything interesting. "If you guess more than Amy, she'll give you 10 minutes of anything with her boobs."

"Whoa, whoa, whoa," I interjected, "What if I don't approve of that.... it just kind of weird."

"And if you beat Drew you can end your crossdressing bet immediately." I thought about that for a second. I mean dressing up wasn't that bad... but they weren't my boobs either.... if they were inanimate objects, I'd destroy for sure. "Only if it's objects, not food."

"Deal," David responded immediately. We set up timers and a chair in the middle of the room. When in the hot seat, we simply closed our eyes, which put more stress on honor code.

Drew and David went at it hard. They both practically swallowed some of their items. It was unbelievably fast and competitive. The 2 minutes flew by so fast, in an instant we were tallying score. Drew won by the skin of his teeth leaving David salty. Next up was Bryan. He got so into it he broke the chair falling back on it after. Seeing him correctly guess 6 objects was intimidating, but I had confidence still. The three took a little more time to gather my items. David even had to go to his car. Since I didn't have a chair, I just kneeled on the ground. My mouth watered in anticipation and my hands were sweaty. When I closed my eyes, I imagined freedom. Everyone said go simultaneously and I stuck out my tongue. The first was papery and dry. "Cardboard! Next." The second item was a water bottle and the third was sunglasses. The fourth was a little tricky. It was plasticky, cylindrical, with a cotton top..... it licked it over and over trying to get any other detail out of it. I didn't get it until I put the whole thing in my mouth. "ewwww, tampon. Next." I instantly knew the next one, it was a tiny soccer ball. I had 5 down and a little less than a minute left. My next item was smooth with an unorthodox texture. Maybe.... rubber or silicon. It was long and cylindrical, but I had no idea what it was. I started getting more desperate because I was just one away from being tied up. I licked the length of it and put it in my mouth. I swirled my tongue around it sucking furiously to keep from drooling on myself and the floor. It was slightly cold and flexible... ahhhhhh, what was it. I felt every bulge and divot and still had no idea. It felt like forever on my knees licking and sucking. But eventually I got it. "Dildo!" I said excitedly. I opened my mouth and waited for the next item. Drew brought me back to reality, "Time was up a minute or two ago... you really went at it."

"Ohhhh...." Bryan put his arms in the air and did a victory lap around the couch. "Let's boot up a game, I'm done tasting stuff," David said simply.

We gathered round the couch, eager to begin. I sat on my legs like I've seen lady's do in movies. Bryan had different plans. "Girl, come sit right here. I'm using my 10 minutes now." He gestured towards his lap. With a relenting sigh I stood up and followed instructions. He grabbed my chest from behind and started fondling them while David, Drew, and I started to play. He started to sway his pelvis side to side. Since the skirt flared out, my pantied butt was directly touching his sweatpants. Which was fine until I felt his rod through them. Hard as a rock and definitely not small. I tried to stand up, but he held me down as his fondling got more and more intense. Bryan whispered in my ear, "start slowly swaying for me." I hesitated and I thought about my situation. I was in a French maid outfit getting groped on the lap of a guy probably twice my weight. I didn't exactly have much pride to hold onto... and the attention was... nice. I mean who doesn't like attention. So, I started to sway my hips back and forth. His member poked up and followed the movement of my bubble butt. It was the size of a zucchini! Probably bigger than my lace covered feet.

He started bouncing his legs and I started really grinding, my mind still half focused on the game. What made me lose the match was Bryan's next move. He stopped playing with my breasts and slipped a hand under the frills of my skirt. He started stroking my tiny package as if I was a girl. The frills hid what he was doing, so I made sure not to make a scene. He continued with gentle rubbing motions. After a while I noticed the harder I grinded the faster and stronger he would rub. So naturally, without thinking, I started giving it my all. With his cock between my cheeks I swayed up and down, left, and right. I think this continued for way to long, but I don't know. I had never touched my own penis in anyway like this and it felt weird... but I think in a good way... idk. Then Bryan stopped. Letting me partially deflate and he just held his hand there. I started gently humping his hand in an attempt to maintain arousal and get him to keep going, without being noticed by the other two. Though I'm pretty confident they saw me swaying my Butt. Bryan got me wanting more. Instead of rubbing me he pulled his phone out of his pocket. He opened google photos and clicked on the first video. As the video loaded, I saw the first image. My heart stopped.

I saw two things. A French maid on her knees giving a very enthusiastic blow job to a realistic cock, and very clear and excited feminine yell at the end, "dildo!". The worst part is it was clearly me. I didn't put on much make up, and my hair wasn't that much different at all. After showing me this Bryan Leaned into my ear, practically licking it, "you'll do what I say this week, won't you?" I slowly nodded in fear. My life could be ruined by the video. This got me dreading tomorrow and even practically ruined my good mood. Just like Bryan said he could.

Bryan rubbed me a little more as he moved me back and forth on his lap. It didn't even occur to me that it had been well over 10 minutes. After a few more rounds he stopped and reached into his pants. He pulled out his finger and told me to lick it. Without even looking I sucked it clean. It was salty and bitter. I learned later that I had just had my first precum. "Hey, this is a hot piece of meat. Y'all want to fight for her?" Bryan egged on.

"You got a deal! Winner of next match gets Amy for a game or two." David countered. Everyone agreed and Bryan took my controller. Funny how they didn't ask me, nor wait for me to respond. I was too deep in a hole to care about digging myself out tonight. I simply played along and waited till the match was over. David won so he walked over, picked me up like a toy, and sat back down with me on his lap. His arms were wrapped around me with his hands on his controller. He whispered in my ear, "spell the alphabet with your butt." Man, I got shivers every time someone whispered in my ear that close. I thought it was strange, but I went along with it. I guess because I was surrounded by the strongest guy in the school. He was also twice my height and three times as heavy. Starting with 'A' I swayed up and down, left, and right. I felt his cucumber slowly inflate to full size. By the time I was on 'G' he was now slowly trusting into me. He must've been at least 9 inches, slightly longer then Bryan. Wait... was I comparing size. Why would I even notice a thing like that? This worried me, so I leaned back and asked Dave, "isn't this gay?"

"Not when your dressed like this." ... I'm not sure how I felt about that. I'm still a guy, right?

Before I got to 'U' Drew won the match and came to pick me up. I found the letter S to be satisfying and easily repetitive. So, I did figure 8s to Drew. He was the smallest, but definitely the widest. Probably... 7 inches. Did I really care? Either way they were all twice if not three times what I had to offer. I was fully aroused but couldn't even peak out of my tight satin cage.

The next hour was me being traded like a trophy around the room. After finding a rhythm, I got a technique. If I put their cocks between my butt cheeks, I could control how it moved. I would interchange between grinding faster and swaying slowly and sensually. I would do figure 8's, bounce up and down, and quickly wiggle in place. I got pretty good at it too. I also learned that I could do a lot more if I turned around. When I did, they could admire my cleavage and I had a whole other range of motion.

I started doing forward facing more often, because I could get off a little on it too. I could gently rub myself into the person I was on. It was gentle enough that they wouldn't notice, but strong enough to give me some satisfaction. Especially on Bryan since he had more of a gut. In fact, I was on Bryan when this all stopped. I was facing him and aggressively bouncing. I had something building up, I didn't know what, but it was something. I got more into it and got the attention of everyone. The game was paused, and all attention was on me.

I felt like I was going to explode. I got lost in the moment and climaxed. It was a glorious feeling I would never forget. "Amy! You made a mess all over me." Bryan said in disgust. Afterglow disabled me from processing a response. I was flipped onto my stomach. Still on Bryan's knees, I was facing the floor. He pulled down my panties and raised his hand. A spank swiftly reminded me of my position. I shot my legs up. Spank after spank made tears swell up in my eyes. "Never do that again!" Bryan yelled. The barrage continued for what felt like an eternity.