Adam Loses a Bet Ch. 04

The next morning, I woke up a little early, although it only took 1 hour to get ready and eat breakfast. As I was walking out the door to wait for Bryan, I remembered the black box. I took it to my bathroom and took out the contents. I saw the underwear, a black bag, and a pink plastic object that looked a little phallic. I looked at the instructions and dropped my jaw. It was a butt plug. At the bottom of the black box was an enema. No no no, this was wrong. I wouldn't do this for a fortune. I put the content back in the box and headed towards the door. On my way I passed my mom crying at the table. She was counting the money I had left her last night from Bryan. She stood up and gave me a huge hug. She said, "I don't know how you got this, but this solves so much! Thank you." I embraced the moment and let a single tear of joy fall from my face. I would never forget how happy I had made my mom. She then left for work and I was left alone in the house.

I let out a sigh and headed back to the bathroom. I would do anything to make my mom that happy again. I took out the enema and cleaned myself out 3 times. The water ran clear and I put lotion on the plastic mock penis. It wasn't big, but small wasn't a word I would use either. I put it on the toilet seat and positioned myself above it. Biting my lip, I slowly fell onto it. I felt my own resistance to the tip as it pressed at my entrance. In an excruciating moment it slipped in, tearing me apart. Feeling the smooth plastic inside me was foreign. The lotion made it a smooth process, but it still hurt a ton. I felt like it was ripping me in two. The instructions left for me told me the pain would pass shortly, so I soldered up and took it.

As I bent down to pick up my underwear for the day I had to stop. Man did it hurt to move with this thing in me. I slipped the thong on. It barely fit and slipped snugly between my cheeks. The elasticity hid my member, leaving a flat space between my legs. The lace looked expensive and probably was. How did Bryan get these so quickly? The bet started just last Tuesday! I wore joggers so there was no visible underwear line or lack thereof.

Having completed the weirdest start to my day, I opened the door and waited for Bryan. I could feel the insert move inside of me. I sat on my pouch and thought about how I was going to do this all day. He pulled up a moment or two later. While walking to the car, I could feel the length of the plug move with my legs. Sitting down just pushed it deeper. The first thing Bryan said when I sat down was expected, "you're wearing it, right?"

"Yeah."

"Bend over, let me see." I leaned against the car dash and stuck out my butt. He pulled at the waistband of my joggers like he was checking a diaper. "Dang that looks hot," he admired. Continuing his inspection, he reached in and touched the base of the plug. Once checking if it was there, he grabbed the base and pulled it slightly in and out. It didn't feel bad, but the plug still hurt in general. "You'll get used to it fast. Heck you might end up enjoying it," comforted Bryan.

"This is just for the money, don't get any ideas."

"Sure," Bryan winked. After changing the subject to a more masculine topic, we drove to school and headed to class.

During every class, I was constantly shifting my position, trying to find a comfortable way to sit. The way I most commonly came back to was perfect posture. If I sat up straight and stuck my rear out, most of my weight would be on my thighs. Sure, it wasn't the manliest way to sit, but it was comfortable for today. Besides that, school zipped by. All I really recall was always being reminded of my little invader every time I moved.

During lunch Bryan texted me and asked for a photo, to prove I was still wearing it. I didn't argue, 2k is a lot for me. I went to the bathroom and used the handicap stall. I simply pulled my waistband just below my butt and bent over. I took one picture of just me in the thong, and another of me holding my butt apart so you could see the plug. He really approved of that one.

By the time my last class started I had gotten used to the new feeling. I still shifted in my seat, but it had stopped hurting. Today, the last half hour of class we had homework time. Amy and I used this to talk. We would talk fashion, hair colors and dyes, best outlet stores for clothes, and best fast-food places. The last one segued really nicely into my favorite topic of the day, dating spots. When the moment was right and it seemed natural, I casually asked, "Where are your favorite places to go on dates."

"Oh, I don't know."

"Not just places, what do you like to do?"

After thinking for a sec, she responded, "I like seeing the weird side of people. Something no one else knows or a special hobby they're passionate about. Something interesting, I guess." Before I could respond the bell rang and we packed up to leave. Dang. What a poorly timed bell.

I met Bryan outside and we went to David's. The entire drive I dreaded what kind of cruel and unusual punishment waited for me. Upon arrival I was escorted to the bathroom where I knew what to do. Essentially, I was going to be put in an embarrassing outfit and get awkward attention all day. Then I would attempt to diffuse the situation by embarrassing myself even more.

However, after looking down I was shocked, but this time in a good way. Both the pants and sweater were long sleeved. I picked up the black lululemon's and tried to put them on just like any other pants. Not going to lie, it was a little tough getting them on; they were a tight fit. It didn't help that my butt plug moved every time I did anything. After putting them on, it felt like I wasn't wearing anything. It took a moment to admire my rear and how the pants really clung to my curves. Dang. I kind of had an impressive butt, I guess the squats have been paying off. A quick little spank resulted in a satisfying ripple effect.

Fortunately, you couldn't see any bulge. I found this odd because I was aroused and should be tenting, that's what guys do right? Thinking about it, my tiny tent was probably held back by my panties. Yeah, that was it. I'm a man regardless of my undergarments.

I resituated myself and looked around for the next item. Under the thick sweater were the breast forms and a black lace bra. I had done the breast forms yesterday, so I knew what I was doing. Regardless I still struggled a bit. The realistic nipples caught me a little off guard. I didn't really look at them last time. I used the glue and concealer to fasten them to my chest and hide the line between the forms and my skin.

Moments later I had realistic breasts and had moved on to the bra. It was tricky to put on; it took a few tries before I think I did it right. I didn't even bother putting on the matching bottoms. I wanted that 2k, so my tight pink thong would suffice. The sweater was pink and loose. It showed 1 bra strap and a small midriff. The sleeve covered the palms of my hands, making my fingers look small. For the first time this week, I didn't tie my hair up. I let it fall on my shoulders. After searching the drawers, I pulled out a brush and a little makeup. Brushing my hair made it look smoother.

Similar to the days previous I added one more element to my makeup routine. A little eye shadow was easy and made me look 100% better. Together, the mascara, lip gloss, and eye shadow made me look nothing like a guy. My soft jawline was the selling point.

Having finished getting dressed I took a moment to admire myself in the mirror. The yoga pants felt amazing and looked even better. It was a good look and I actually was a little excited to show to boys Although, it was a little disconcerting how passible I looked. I'm still a man, right? A boy maybe? Perhaps a little feminine, but in a metro kinda way, yeah. A metro kinda way.

When I opened the door, I was disappointed to see no one there to gawk. I walked downstairs to find all three invested in a match. "I'm done," I informed them. No one even turned around. What happened to all the interest they had yesterday?

I tried to hide my dismay and sat down in my normal spot. I was still a little sore, and the plug made sitting a little uncomfortable. So, I laid down on my stomach with my butt facing the guys as consequence. It felt like an offering, so I felt like I deserved a little attention. Even a little bit. I even would wiggle it a bit to get a little reaction. Nothing. They would talk to each other like I wasn't even there. It felt bad, not gonna lie.

Was it something I did or say, or did I just not look good today? These were the things I thought about for the next hour. Eventually David stood up, picked me up and sat down with me on his lap. Finally, some attention. I immediately started to sway my hips gently. I noticed that I was also moving my plug around inside of me, but it didn't hurt. I picked up pace. I wonder when the plug stopped hurting, now it felt almost... good... I think. What I'm talking about, I should just focus on getting a reaction out of David.

I continued to put on a show for him. For the first time in a while, I noticed how thick his thighs were; they were the size of logs but looked chiseled like stone. His quads were easily the size of my forearm, and his calves more closely resembled full grown bulls. Since he was wearing shorts, his bare skin was touching my lulu's. without thinking too much about it, I slid my hands down and moved them up and down his leg. I could feel his muscle, his power. His tight, thick, strong, masculine, impres... WOAH! He is definitely aroused. I could now feel his cock struggle against my butt.

I think I knew how to get him to notice me. I slid his cock, so it was positioned between my cheeks and started twerking side to side, fast. This would get him.

He didn't even make a comment or grind back, what the heck. I did all the work and got no attention. I got more intense with my grinding, but nothing worked. Bryan won a match and came to pick me up. If I'm being honest, I was a little disappointed, but I wasn't having much luck with David anyway. I raised my arms up to make it easier to be picked up. It still impressed me how easily the guys would pick me up, it was like I was a toy.

I was placed facing him this time. I started with figure 8's and moved on to bouncing. Bouncing really moved around my insert. All he did was put his hand on my shoulder and tell me to calm down. His excuse was that he was trying to play a game. WHAT! I was doing this for them! No part of me wanted to be in this situation. I resumed gently swaying while giving a defiant glare to Bryan. He probably just saw two big brown puppy eyes looking up at him through painted eyelashes.

After doing this for a while I just gave up. I rested my hands and the side of my face on Bryan's chest and casually watched him win match after match.

Eventually, I excused myself to the bathroom to rethink my day. Almost instinctively when I closed the door, I took off my sweater. I touched up the concealer on my chest and applied more mascara and eyeshadow. If I was doing this for them, I was going to do it right. I was so sold on this idea, I repeated to myself in the mirror. I felt an increasing amount of motivation as an attractive girl told me, "If you are doing this for them, do it right." So, I turned to the internet. I had heard the term lap dance tossed around in gym locker rooms, but never knew what it was. I figured it sounded relevant and looked up techniques on my phone. I found that most recommended things to do I was already doing. But one thing stood out.

When I returned to the room, I found the same dull faces showing no interest in anything but the game. I walked in front of the match facing the screen and took off my sweater. Leaving nothing but the bra between my chest and the guys. I turned to face them and walked over to David. The game was paused, and all attention was on me. I sat down on David's lap, but this time I gripped his thighs like a vice. Using the additional stability and control I now had, I grinded like there was no tomorrow. I leaned forward with my chest and back with my head, this put my cleavage as close as I could get to his face. He grabbed my loaned boobs and started to squeeze and toss them. It was a lap dance and a half.

After only a minute of this he let go of me and grabbed his own pants. He reached in and pulled out all 9 inches of his cock. The second I saw it I protested, "woah, woah, woah. I can't touch that. That's gay."

"Not dressed like that. You're Amy not Adam"

"No, I just look like..." I was cut off by David pulling my back onto his lap and grinding into my butt. His hot dog fit in between my buns and I was physically forced to get into it. Still holding me into him, David stood up and flipped us around. With my head now on the arm of the coach he started dry humping me. "Stop! This isn't right!" I pled, but he kept at it. Bryan and Drew watched like it was a movie. Every repetition filled the room with a different sound of slap. I felt helpless, used, and... kind of aroused.

He started getting more and more intense until I was using all my energy just to hold on to the couch. He would force my butt to do circles and shakes before returning to humping. Eventually I resigned to his herculean strength and stopped resisting. As I just took it, I felt an exciting feeling coming from the dildo shoved up my ass. Focusing on that helped distract me from the feel of my boobs bouncing back and forth while my bra struggled to contain them. Without thinking I started responding to David with occasional twerks and gently pushing back. I stopped supporting my arms, so the top half of my body fell into the couch, presenting my ass like a trophy.

After a few minutes David picked up his pace. My head was pushed into the cushion as he let a load out on my spandex covered butt and exposed back. I was in shock. David gave me a spank, causing a ripple effect under the lulus. He high-fived Bryan and Drew before sitting back down and starting the game again.

What was I supposed to think? I was just dry humped until another man came on my butt. I guess I should clean myself up. So, I went to the bathroom to clean up the sticky mess. I maintained the same dumbfounded face the whole time. My mind was both racing and frozen; I didn't know what to do or what just happened. Upon opening the basement bathroom door, I fell to the ground and curled up into a ball. Thoughts bounced back and forth in my head like a tennis game in an empty cavern. That's it, that's how I felt. I felt empty. I had put back on the sweater on my way here. It was a good comforter at this time; it was warm and felt like a hug. A single tear swelled up in my eye before I calmed down. I wiped up David's seed and stared at it. I'll admit curiosity got the best me. I tried a small taste before opening the door. Salty, but not unpleasant

I sat down in my usual spot and we talked like nothing had ever happened. It kinda helped me relax. We had decided to finish the night with a movie. My mood was drastically improving as we continued making jokes about this and that. We settled on Battleship (the movie). Bryan got up from the couch to make popcorn, so I stole his spot for the movie. I didn't mind sitting on the floor for games, but you were supposed to relax during movies. Plus, Bryan typically brought down a folding chair for movies. We started the previews while Bryan came down the stairs.

He handed two popcorn bowls to Drew and David and turned to me. Rather than take the L and sit on a folding chair, he decided on a better plan. Bryan picked me up and sat me down next to him on the couch. It was a small couch, so I was squished between him and the side cushion. I couldn't get up. There wasn't enough room for me to wiggle free without Bryan moving. I wasn't uncomfortable, in fact this wasn't too bad. I had fully relaxed as the movie started.

I'm not sure when, but sometime near the beginning Bryan lifted his arm up and around me. My head fell just below his shoulder and my arms onto his chest. We cuddled like that for a while. It was comforting, like the sweater. I wasn't opposed to being comfortable during a movie. He started to slowly rub my midriff with the arm that was around me. My stomach was getting chilly, so it was a welcome advancement.

What I wasn't prepared for was Bryan's next move. He pulled his phone and a little remote out of his pocket. "Psst, check this out." He whispered in my ear. His hot breath and the feel of his lips on my ear definitely got my attention. I looked at his phone as he unlocked in. He opened a video on YouTube and pressed play. My eyes went wide as I saw a half-naked female version of me giving David a lap dance. We watched until David came on my back and butt.

"Don't worry, it's a private video right now, no one can watch it but me," David soothed. He grabbed my small hand and placed it over his very hard member. "Just do as I show you," he whispered. Guiding my hand, he squeezed and massaged his not so little trojan. He let go and let me continue the work. I felt that same helplessness I did with David earlier. But this time was different. I felt comforted, loved, warm, or even cared for. He then showed me his tiny remote. "Click it," he suggested. I did what I was told to do without hesitation. When I did, the last thing I expected happened.

I felt my insides and rectum start to vibrate. He swiftly put the remote back into his pocket and turned his attention to the movie. EXCUSE ME! He tricked me into inserting a vibrator into my ass! Any feeling of warmth I felt earlier was replaced with betrayal. He whispered absentmindedly, "$500 if you can stay quiet during the whole movie." Easy. I was still mad, but I was never one to talk during movies anyway. Though my thoughts were on anything but the movie. I continued to message Bryan's cock while he stroked my exposed side stomach. Additionally, there was a vibrator inside me gently sending a new sensation up my spine. It felt good if I'm being honest. The vibrations were somehow soothing and exciting at the same time. I found a rhythm with Bryan's hand and my own. My other hand went between my legs. I tried to rub myself a little without being noticed. This whole situation left me really horny, and I don't know why.

Bryan grabbed my hand and shoved it under the waistband if his sweats. He wasn't wearing underwear. I continued my work as he got more handsy with his. The arm around me pulled me closer into him as his hand worked its way lower and lower. Reaching under my yoga pants Bryan grabbed the back of my thong. He pulled up, consequently pushing my vibrator further into me. This drove me wild. He began groping me and I started pushing into his hand in an attempt to go deeper. The vibrator picked up in speed and I started rubbing myself harder. I let out a subtle moan inadvertently.

Then nothing. Bryan stopped groping, the vibrator stopped moving, and the movie was coming to an end. I leaned over to Bryan, still massaging him. "What the heck, why'd you stop?" I asked in a high-pitched hushed voice.

"Oh. I decide when you climax, plus you just lost the $500 with that moan. You're lucky I was the only one who heard it over the movie." Great. I was horny as heck and didn't know what to do about it. Plus, I lost $500!

The movie ended and I went into the bathroom to change. I was practically a pro by now. I had to use the bathroom, so I removed the plug and washed it. By this point, it was a relief not to have it stretching me out. I did my business and changed back into my boy clothes. Of course, with the exception of the thong and plug. I re-inserted and went out the door. Bryan was already in the car. I hopped in and noticed that his center console had been folded down to create a bench-like look. It looked kinda dope; expensive leather and walnut really did go together. "You gonna keep going?" He said gesturing to his crotch.