Adam Loses a Bet Ch. 05

The next morning, I woke up a little late. I very quickly showered, used the enema, and brushed. I frantically re-inserted my plug and dressed like normal. Without even thinking I slipped on the matching bra I left on the counter. I rushed out the door and found Bryan already waiting. I nearly sprinted into his car and fell face first into his lap. "woah, calm down there girl. You'll get plenty of quality time later, get you head up and put on your seatbelt," Bryan instructed. I obediently sat up and fixed my posture. I'm just glad he didn't leave without me. We made it to school on time with almost no time left to spare.

Bryan seemed excited this morning. He said David was going on a date and Drew was sluffing, but that wasn't why he was excited. The moment I sat down for my first class; I knew why he had so much energy. I saw him across the class pull out what looked like a garage door opener and click it. My butt started humming as my vibrator was turned on. I rolled my eyes and immediately sighed. This was going to be a long day. The vibrator would turn on and off during random intervals leaving me never knowing when to expect it to change. I felt like everyone at school knew what I was hiding. I quickly realized I had absentmindedly put on the bra, but it was too late to take it off now, in front of everyone. So, I just hoped no one would notice. The entire day was torture, constantly in between aroused and nervous. I had adrenaline times 100. I don't think I listened to a single word any of the teachers said.

During lunch I slipped away from people into room 405. Bryan came into the room, probably to tease me. The vibrator started back up and I started shifting uncomfortably. "Having fun yet?" Bryan started.

"What do you think."

"It's just 2k, you can still back out."

"Heck no! I've made it this far, nothing's gonna make me back out."

"Nothing?"

"Nothing."

We ate lunch in the room mainly talking about girls and food. You know, guy stuff. I decided to not go to my last class. If Amy heard the vibrator or saw my underwear, everything would be over. The insert turned off, giving me a second to breath. I casually scrolled through Instagram. 20 minutes passed before I even talked to anyone, but you wouldn't believe who I ran into.

When I heard the door start to creak open, I was startled. I almost fell out of my chair when Amy turned the corner. She looked flawless. A high ponytail, expertly done makeup, perfect skin, the whole package. She even had her cheerleading uniform on, there must've been a meet today. "Hey, what's up?" She said, breaking me out of my trance. "Nothing much, what about you?"

"Well I got a snap chat from Bryan telling me to come to this room. There was a sub in biology, so I thought, why not." Gosh dang Bryan, you went too far this time. Without thinking of the possible ramification, I said, "Oh, I was just kinda sluffing in here. Wanna sluff with me?"

"I'm down." Why did I say that! Sure, it was smooth, but what about the risk of her finding out!

Regardless of my internal screaming she sat down next to me. My stomach felt like a balloon; my palms were sweaty. We started talking about this and that. Really, I was just thankful there was no buzzing right then. She mentioned something about cheerleading. I talked about the fitness club. Eventually our conversation got more intimate as we started talking about family and life at home. I started to calm down a bit.

Moments felt like millenniums but passed like milliseconds. Everything made sense when we talked; we clicked. Her eyes captivated almost the entirety of my conscience. Time slowed down as our deepest versions of ourselves became exposed. The entire conversation became irrelevant as our connection became something so much more. We slowly moved closer together. Her perfume smells like fresh strawberries and Roses. Nothing could ruin this perfect moment. Then it happened.

The vibrator turned on more intense than it had ever been before. Immediately I had a problem. Looking at her helped distract me from it, but it was hard to ignore. A strangely good feeling flew up my spine as the device grew in intensity. What was I going to do! If we had one break in the conversation, she would definitely hear it. Maybe she would assume it was an A.C. unit or a radiator? I stopped listening to what she was saying and started thinking of escape routes. Maybe I could jump out of the window? Tell her I had the plague or had to go to the bathroom. A hundred possibilities flew through until I was saved by the bell. Literally.

As the bell rang Amy turned to me looking disappointed. "This was fun, we should do it again." She stood up and gave me a quick peck on the cheek. It happened in an instant and caught me off guard. She walked out of the room, leaving me in speechless stupor. The vibrator stopped and I sat in silence staring at a wall. Everything felt O.K. in that moment; everything was going to work out. Bryan brought me back to reality, "come on, let's go. It's gonna be a busy day today." I didn't see him walk in. I wonder how long I was in afterglow.

We left the school in Bryan's Mercedes. The whole trip I just stared out the window thinking about Amy. The only thing that took me out of my trance was the car stopping in front of a mansion. "Why are we here?" I asked.

"Oh, well David and Drew are M.I.A. so we're hanging out at my place. You still gotta pay for losing the bet."

"But, but."

"No buts, just yours in a cute outfit." I would've argued longer, but this was the best week of my life. Nothing could get me down from the progress I was making with the hottest cheerleader in the school. She was only an inch shorter at 5'4" but she must've liked me somehow. The kiss was proof of that.

We walked into the house and I was directed into a bedroom. It was huge. The whole bedroom was probably half my home. Looking at the bed I saw a familiar sight. It was our high school's cheerleading uniform. Our colors were red, pink, and white, so the uniform was mostly pink and white with red accents. This was the summer uniform, which showed a lot more skin. There was also a white lace bra with my usual breast forms. I started to get dressed.

After stripping, I grabbed the leggings that matched my skin tone and slowly pulled them up around my legs. Since I was always doing squats my thighs were thick. They had no definition, but I had hips for days. Similarly, I had been working my glutes for the past month, so I had a bumper anyone would be jealous of. Although, all my fat went to my legs, so I was a little jiggly. The skirt barely covered my butt and showed off my legs.

The forms and bra were next. I quickly glued the forms on and used the concealer to make them look like mine. I think the bra was a push up. Since It made my new breast look extremely perky. The top was the icing on the cake. Since these uniforms were exclusively for summer competitions, they had a midriff. I wonder why this was a theme with my outfits. The skirt rested as low as the school could get away with and the sleeveless top just barely covered the bottom of my bra.

Having finished with the clothes I looked around the room. There was a portable vanity on a nearby desk. Opening it, I saw every possible shade of pink and black. Maybe I could match Amy's look, I mean, that is what the boys called me when I was dressed up. I tied my hair in a high ponytail and started with foundation. I was trying to replicate what I had seen my little sister do every morning. After foundation came eyeshadow, eye liner, and mascara. I toned my eyebrows and contoured my cheeks. After sculpting my lips into a pink masterpiece, I was shocked at the result. There was no way the girl in the mirror was me.

The soft jawline was mine and so was the hair. If you already knew it was me, it was obvious. But dang, I was cute. I had managed a pretty great makeup job, I even contoured correctly. There was no hesitation as I walked out the door to show Bryan what I had done. "Check it," I said in a feminine tone.

"Dude, you're sexy. It's like that uniform was made for you."

"It fits perfectly for sure."

"Well I just queued a movie, wanna watch?"

"Yeah, sounds fun"

We walked down two sets of stairs to a theater room. It had a projector and a million different places to sit. Despite the love sacs, moon chairs, recliners, and futons, we both sat on the same small couch. Right in the middle of the room. Bryan seemed really excited about the movie, so I was kinda excited to. I was quickly disappointed as both the movie turned on as well as my vibrator. The movie started with a half-naked girl in yoga pants giving the lap dance of a lifetime to David. As David picked her up and started dry humping her, no one who knew me wouldn't recognize her. Immediately after David came on my back and rear the movie cut to a French maid blowing a dildo. Her enthusiasm and effort were only paralleled by my embarrassment. To be fair, I had no Idea what I was blowing. That one ended with a very happy looking cross-dressed boy. "Pretty great, right?" Bryan teased.

"What's your point? I already know you're blackmailing me. You've used these before."

"Then you already know what today is gonna be like. Put this on," he handed me a delicate pink collar. It read, "Bryan's Sissy."

"Bro. This is taking it too far, right?" I protested.

"You don't get a say in the matter, put it on sissy. Aren't you down for anything?"

"But I'm a man Bryan."

"What kind of a man wears a thong and a vibrator. You're wearing a sexy cheerleading uniform and makeup right now. You're no man, you're a sissy! Put it on." Those last words came out harshly. The vibrator turned off and back on as if in agreement. Without further argument I put on the collar. Seemingly satisfied, Bryan turned on an actual movie.

It was a comedy drama, but I didn't actually watch much of the movie. As it started Bryan picked me up and placed me on his lap facing him. I knew what he expected but didn't move in protest. It was a few minutes before he let out a relenting sigh. Had I won just like that? Just 2-3 minutes of not giving him a lap dance. Nope. He picked me up by the stomach, placing me over his lap facing down. I tried to resist but with seemingly no effort at all he pulled up my skirt and my panties down. 3 swift slaps to my exposed rear put me in my place fast. My plug didn't help much either. This time, when he sat me up, I started grinding without a second thought. Figure 8's, bouncing, the alphabet, I did it all. I felt exhausted as time crept on in the slowest way possible. An hour in the movie and I was still going at it.

Up until this point Bryan was pretending like I wasn't even there, but that changed very suddenly. While I was still exhausting myself, Bryan put his hands on my back and pulled me into him. Our lips met and he turned me into the couch, under him. I was too tired to resist, and frankly I was 1/3rd of his weight. I wouldn't have been able to run away, even though that's all I wanted to do. He started to put my mouth to use. His hands traveled down my back into my skirt. Thankfully, he stopped at my butt, I don't know what I'd do if he touched my hard on while I was mad at him. I didn't even know why it was there. His hands were all over me; there were no boundaries. He shot his tongue into my mouth and started to explore. I had no idea what to do. As we made out, a million thoughts ran through my head.

This was my first time! And it was with a guy! Nothing good could come of this. Unless... if I became really good at this, I could use it with girls. Like, maybe... Amy. Now there was an Idea. All I had to do was pick up all of Bryan's tricks and tips. So, I started mirroring him. My slender hands felt up his chest and shoulders. My tongue started to explore his mouth. I even let out some gentle moans. That really got him going. We established a rhythm and then changed it, constantly getting more aggressive or sensual. I wrapped my legs around him for support. He saw this as a green light to start playing with my butt.

He had been groping some part of me this whole time, but his next move made things interesting. He grabbed my still vibrating plug and started moving it up and down. That felt good. I started pushing back against his hand in approval. I focused on our lips while he focused on my butt. We fell off the couch and I ended up on top. I used this opportunity to start grinding against him.

Nothing made sense, but I guess I was fine with that. My feminine moans got more intense. My grinding got more hot and heavy, he matched the pace with his hand. The vibrating phallic insert started flying in and out of me. It hit a spot that got a reaction from me. Bryan took notice and focused on that area. In and out, the vibrator hit the perfect place every time, and Bryan knew it. My eyes almost rolled to the back of my head as the pleasure built up. I didn't know you could feel this way from your butt. The pleasure built up like a water balloon ready to burst. I couldn't hold on much longer if I tried. Then, nothing.

The vibrator stopped, Bryan let go of me and stopped kissing back. In an effort to push Bryan into a little more fun, I started kissing down his neck. His strong black hands grabbed my waist and he pulled me downward. I continued to kiss him all the way down his body until he planted my face right in front of his tent. "Pull back the waist band." He commanded. My clouded mind couldn't think of a reason not to, so I did. Almost immediately I was slapped in the face with his cock. It was huge! This was my first time seeing one in this position. It was obviously dark and long, but it was also veiny and hard. "Now I expect a good blow job from you Amy," Bryan started, "I've seen you give some good head for practice."

"Isn't this gay? And wrong."

"Not to a sissy."

"Yeah... but still."

"Do it or I know a certain cheerleader who would love to see a certain video of you." That got me scared. Up until this point I had never thought about her seeing it! She was easily the hottest girl in high school, and for some reason, she liked me. Ain't nothing gonna get between my chances with her.

So, I slowly opened up and tasted my first cock. My tongue flicked the tip as I lowered myself. I fit my mouth around it and went as far as I could down. I only made it halfway. It was thick and huge; how could anyone take this monster. I started bobbing up and down and sucking on it while my tongue made circles around it, just like I did with the dildo. Bryan really liked that. Surprisingly, his cock didn't taste bad, probably better than the rubber of the dildo. The tip was a little salty, but that was my fault. Strange how it could be soft and hard at the same time. I found that he really liked it when my tongue worked right under his head.

Bryan grabbed my head in encouragement, so with his aid, I started bobbing more aggressively. Then, without warning, Bryan pushed me all the way down. His tip broke past my barrier and into my throat. I immediately gagged on it. My nose touched his pubes, and my chin slapped his balls. He started using my face as a tool. Up and down his entire length, faster each time. My throat resisted every time, but that didn't stop Bryan. All I could do was suck and lick; Bryan did most of the work. My throat never got used to the constant penetration, and he went faster and faster. Then, he started to tense.

"Open your mouth, close your eyes, and say sissy after me." He instructed as he pulled out. I opened my mouth and stuck out my tongue. Thick streams of cum landed on my face and into my mouth. His load was absolutely massive! Fortunately, I didn't have any previous experience to relate it to, but I would say at least a half a cup. It kept coming out like a fire hose. The strangest part of me worried that it could stain my cheerleading outfit. Bryan finished unloading and asked, "What are you?"

"A sissy!" I responded as instructed.

Bryan stood up, leaving me on the floor, "Eat all the cum on your face and then go re-apply." I did as was instructed. The salty, bitter taste wasn't unpleasant, just new. I went back up into his bedroom to re-apply. In the mirror I saw a hot mess. My hair was all over the place as well as my make-up. Noticing that I had left some cum on my nose I quickly swiped it up and sucked it off my finger.

I re-adjusted the skirt and top and headed to the portable vanity. I fixed my mascara and lip gloss and had to completely redo my contours. This time I used a little pink blush. Looking in the mirror I once again saw the cute cheerleader stare back at me. Except this time, she had a collar around her neck. "Bryan's sissy," I read aloud. I sounded so alien. I let my hair down and brushed it, then I left to find Bryan.

He was in the kitchen holding an envelope. "Here, you earned it." He said while throwing the envelope at me. I caught it and instantly recognized the smell of money. "That's 3k for going above and beyond. You can take 'it' out now." 3k! That's amazing! My mom was going to be so happy. I could maybe even get myself a little something. Additionally, I could finally take out this plug.

I started to leave to take 'it' out. "Where do you think you're going?' David snarled.

"I'm going to the bathroom to take out... you know..."

"Do it right here." He seemed adamant; I didn't dare disobey. So, in the middle of the room I started to strip. I took off my leggings and skirt at the same time. When they hit the floor my pantied butt was left on display. I peeled back my thong and slid it to my ankles. This was the first time I had been so exposed. There was nothing between Bryan's lustful stare and my nude lower 2/3rds. "Bend over," he commanded. Though reluctant, I bent away from him, supporting myself on the kitchen counter. My hand found its way to my plug. I started to slowly pull it out. It stopped vibrating right then. Finally, it was out for good.

Strangely, I felt a little empty without it. "Dang girl, you're still open for business," Bryan pointed out. My anus was still open to his delight. Putting the phallic plug on the counter, I began to re-dress. Once I had my skirt and leggings back on, Bryan pinned me gently against the counter, his crotch meeting my rear. He whispers in my ear, "That was hot sissy, let me see those C-cups you've been hiding." Reluctantly, I pulled up my cheerleader top, letting them bounce out. His hands almost shot to my chest; he was instantly groping them. He pressed me against the counter and started grinding into me. Because the forms were glued on, my nipples moved in consequence. Grinding didn't feel good at all without the plug, so I only half heartedly pushed back. Bryan started nibbling my ear, that sent tingles down my spine. He breathed, "I got a surprise for you Amy."

"I don't like your surprises."

"You'll have to like this; I just need to prepare you for it." He let go of my chest and grabbed my waist. His hand slid down to my skirt and he pulled it below my butt. He ripped my leggings in half and pulled my skirt back up. He walked to the table and pulled out a chair, "take a seat." I immediately saw a huge dildo with a suction cup stuck to the chair. It was slightly smaller than Bryan's, but still huge. "I don't even think it will fit," I argued.

"Doesn't matter. Hike up that skirt and sit that pretty little butt down right here." I was stunned. My mind simply went blank as my body moved in betrayal.

I slightly lifted my skirt to reveal my still gaping hole. As I began to sit down, I felt the tip press against my entrance. It was massive. Fortunately, I think Bryan put lube on it. Once the tip popped in, the veiny shaft slid easily. I fell halfway down, every inch I felt it stretch out my insides. It hurt like heck. I looked at Bryan with pleading eyes, but he returned with an approving nod. "Now start bouncing," He directed.