Adam Loses a Bet Ch. 05

I felt defeated and tired. I didn't have the energy to fight back against Bryan. So, I lifted myself up and down on the phallic rubber rod. With each repetition I went deeper. Eventually, I was slapping the chair with my cheeks. The pain subsided and was replaced with arousal. That arousal slowly turned into pleasure, and once I found my most sensitive spot that pleasure grew immensely. So much so that I started to moan every other down stroke. I started sweating and got closer to a finish. My mind lost its ability to think. The repetitions became my entire world and consequently got more intense. I was riding a roller coaster up and was about to fall down the first drop. My anticipation was the driving force for bouncing up and down the entire length. Nothing mattered at that point. Then the doorbell rang.

"Oh, pizza's here, go get it." Bryan interrupted. I would've finished myself off, but he pulled the chair out from under me and I fell onto the floor. Disappointedly, I pulled the dildo out and straightened my skirt. I totally forgot I was in a full sexy get up, so you can imagine my shock when I opened the door and stunned the pizza guy. "Woah, you're hot," he commented.

I blushed, "thank you!"

"Here's your pizza."

"Thank you again."

"Are you doing something later?"

"No, just hanging out with a friend."

"Well here's an invitation to a party I'm throwing. You should totally come."

"I'll check it out." I grabbed the invitation and closed the door without tipping him.

'You're a natural, he couldn't even tell you're a guy." Bryan complimented.

"Thank you," I said with a questionable tone. How are you supposed to take that?

"Now back to business. Go to my room and get changed, we're going out."

"Woah, I've never been outside before, plus didn't we just get pizza? Also, what if someone notices me."

"There's no way that's going to happen. Get changed now slut!" Those last words hit with force. Enough force to will me to the room without further argument.

On the bed I saw something much more conservative then my current ensemble. There was a hot pink crop top that said 'sexy' on the back in white. A new pair of underwear were over a pair of distressed white jeans. I slipped out of my skirt and top, leaving me naked in the middle of the room. Walking over to the vanity, I retouched up my chest concealer and lips. Then I grabbed the new panties and slipped them on. They were black lace with pink trimming and a heart shaped hole in the back. A delicate pink bow on the sides completed the slutty look.

The jeans looked modest initially, but after I struggled to put them on, I was proven wrong. They tightly hugged my legs and had holes all the way up to the top. From the right, you could even see a little slip of my panties. A skinny pink belt held then tight in place. They sat high on my waist, so I used the belt like a corset; I sucked in my gut and pulled it tight. After putting on the tight top I finished the outfit. The result was a hot girl that could pass for a hooker. Rather than stand in shock, I expected it this time. After looking at myself to make sure I remembered everything, I flipped my hair and walked away with Moxy.

Bryan was in the other room waiting. With wide eyes he commented, "Woah, know that's confidence. Let me see that pretty little tush of yours." Without hesitation I turned on my heel and bent over slightly. My bubble butt looked so good in the Jean's; it was like they were made for me. "Hold still, don't you dare move," Bryan commanded. I put my hand on a nearby table for support and froze in place.

Bryan pressed down on my lower back until I was bent lower and my butt stuck out further. He snapped a few photos of me and gave me a spank. "aight, let go," Bryan urged. Before I walked out, I adjusted my shirt to completely cover my bra. It was a high midriff like before, but this one felt different. Tighter maybe?

The second Bryan opened the door all my confidence had left me. The cool, crisp air reminded me of my own immodesty. I tried to pull the pants up higher and the top down lower, but they were skin-tight. I followed Bryan to the car, relieved that we would have some shelter.

We drove for nearly half an hour. We talked about this and that, but I was mainly focusing on my voice. I had gotten into the habit of talking softer and higher pitched when I was dressed like this, but I was really worried someone wouldn't buy it. Every time I seemed worried Bryan would assure me no one would be able to tell.

We pulled up to a mall and parked near a coffee shop. "What are we doing here?" I asked.

"Well, I have plans tomorrow and Drew always spends Saturdays with his dad, so you and David are going to have all day together. David asked me to take you shopping for outfits or anything else you might need"

"what if I want to stay home tomorrow"

"Really, you'd prefer to dress at home? With all your family around?"

"You've got a point... does this mean I get to choose my next outfit?"

"We'll see." Bryan left it at that, and we left the car. Brrrr, it was cold. It had been raining on and off all week, so I guess I shouldn't be surprised. Bryan and I started walking towards the mall where I'm sure someone would recognize me. OH SHOOT! I still had the collar on! I looked like a dog! Hopefully, people would assume it was a choker or something like that, a fashion trend perhaps.

What if a guy tries to flirt with me! What would I do? Should I let him down gently, I think if I'm too harsh he'll suspect I'm a guy? What if he's really pushy?

As if he was reading my thoughts Bryan reached his arm around the small of my back and into my back pocket. "Oh," I said out of surprise. He pulled me closer so that I was pressed against him, I could feel his warmth against my bare skin. I guess this solved a few of my problems. I was no longer cold, and I don't think any guys would try to hit on me. I felt better, maybe even safe.

We walked like that into a coffee shop and then left like that to a bench. Then we shared a steaming cup of hot chocolate while talking about whatever we felt like in the moment. We would laugh and poke fun at each other until hot chocolate nearly came out of my nose.

Finally, we finished our cup and stood up to continue shopping. Bryan hand quickly found its way back into my back pocket and his arm pulled us together. As we crossed the mall, I noticed a guy looking at me weird. I leaned more into Bryan to make it clear who I was with.

I figured Bryan was both swole and over 6 foot, so no one would mess with him. Regardless, another guy was staring at me a few minutes later. I grabbed Bryan's arm and clung to it like a rope. I felt like that was enough to ward off hopeful creeps. Plus, it felt good to be hugging something warm even if it was a bicep. Bryan must've enjoyed it too, the rest of his arm snaked down my exposed back and onto my butt.

Every once and a while he would squeeze my ass and play with it, he acted like he owned it. It was almost like he wanted to embarrass me... or dominate me? It felt more like the latter. I was like putty in his hands, completely dependent on him. I didn't have my wallet or phone on me; No I.D. or way to get home without Bryan. It was kinda exciting being submissive, in an embarrassing type of way.

NOT that I'm submissive, I'm still 100% a man. In 3 days, I would take off this façade and return to being an alpha male who worked out with the strongest kids in the school. For now, I was just playing it safe; I have never been out like this before.

We finally found the clothes shop Bryan was looking for and he led me in. It was huge! Who in the world would need this many clothes? My guide walked me right into the women's section. He would look around with his free hand while I would passively scroll through different tops and bottoms. I wanted to find something modest and gender neutral. But every time I picked up something androgenous Bryan would calmly take it out of my hands and put it back. After one hour of scrolling I had only grabbed two tops that Bryan found suitable, meanwhile he had a stack of clothes for me to try on.

At some point we wandered into the lingerie section, Bryan had a ball there. He spent an eternity comparing each style to every color. He would hold his favorites up to me and ask my opinion, not that my opinion mattered. Eventually he settled on a white nightie set and red lace bra and pantie set.

Bryan then swooped us by the dress section. He picked out a cocktail dress, an A-line, and a few others. Before we made our way to the dressing rooms, he also stopped by the kid's section. He grabbed a pair of heels and pink sneakers. Finally, we let go of each other and I was shewed into a dressing room. I was first given a pair of yoga pants with a sports bra and tank top. I stepped out to show Bryan, but he didn't approve. "What? Look at this," I questioned. I pointed to my butt and gave it a little shake. He had to admit, it definitely brought out my assets. "Maybe, but it's more of a workout outfit. Hey, you could wear it to the gym on Monday."

"Fat chance!" I stepped back into the dressing room to try on something else. I tried on every different kind of jean short and at least 10 different tank tops (none of which covered my bra). Every time Bryan liked an outfit, he would have me take a mirror selfie of it on his phone. After a few skirts and skimpy blouses, we had moved on to dresses.

I had trouble zipping some of them up, so Bryan stepped in to help. "Dang, this one's tight." I complained.

"Yeah but it's sexy though." Bryan commented, as he grabbed my waist and pulled me into a kiss.

"Bryyyyaaaan," I said flirtatiously, "we're in public."

"I can fix that," he closed the door and unzipped my dress. Every part of me said this was wrong, but I let him kiss me. He kissed around my neck before plugging deep into the back of my mouth. We remained in contact as he physically dominated the exchange. He groped me with one hand, pulling me into him, and explored my body with the other. A few minutes later he broke it off.

"Bryan I"

"Shhhhhhhh," He cut me off, "no excuses. I get it." I'm not sure he did, but that didn't stop him from taking off my bra and panties. I thought that was a sign that we were about to get back into it, but then he left the stall with all of my clothes. "Byan! My clothes!"

"oh, here, catch." He threw a small wad of cloth over the door. Having caught it I looked in horror at what was in my hands. It was a red one-piece swimsuit that tied in a bow at the back. "I can't wear this! Throw me something else. ... Hello?... Bryan are you there?"

...

Nothing. Crap! Where'd he go? More importantly, how do I get out of here. I looked at myself in the mirror. With my expensive breast forms and decent makeup job, I guess I could possibly pass as a girl in a swimsuit. The only problem was my flimsy member between my legs, I was rock hard a second ago, but that didn't really amount to much. In addition, there's no pool round here and people don't just walk around in swimsuits. But... it is my only option.

I stepped into the top of the swimsuit and pulled it up. I found the arm holes and slid my skinny limbs through them. I had to stretch it over my boobs, but it fit. I reached for my flaccid cock and tried slipping it between my legs. Given the lack of constriction, I was left with a bulge. Not a big bulge, but enough to give away my secret. "Bryan? Did you come back?" I asked with high hopes. Still nothing. After adjusting the top of the swimsuit to cover as much as possible I poked my head out the door. Bryan was at the cash register paying for his favorite clothes.

I waited for him to finish and watched him come back my way. "Finally, I'm stranded here with nothing to wear!" I said rudely.

"Woah, you better start acting cuter or you're not getting anything"

"... seriously," I said in disbelief.

"Ok, I can just leave. Maybe you could find someone you know and catch a ride with them"

"No, no, no, no, no. fine. Please Bryan can I get some clothes," I said with a little more pep in my voice.

"I don't know. You'd have to convince me" I stood in a stupor of thought before I had an idea. "What if I give you thirty minutes of complete obedience?" I proposed. He thought about it for a second, putting his hand to his chin. "Aaaaannnnd..." he continued. I rolled my eyes. I pouted and looked up at him through my eyelashes, "Aaaaaannnddd I'll be the pwittiest wittle sissy you'll ever owned." I put my arms below my breasts and pushed them up while I played with my hands innocently.

He seemed convinced. "Ok, deal." He held out his hand to shake on it. I reach out and daintily put my hand in his. His grip nearly broke my hand! Anyway, what's important is that he reached into his bag and pulled out a short, pleated, white skirt. I quickly put it on to cover up my junk as he started a timer. "Can I pwease have more?" I begged. He nodded and handed me the pink trainers we had picked up from the kid's section.

"One more thing before we go," Bryan reached into his coat pocket and grabbed a pink leather rope. Before I could figure out what it was, he clipped it around my neck. A LEASH! "Don't you dare fuss about it sissy," Brian warned. I was already regretting my promise.

Brian walked away without me, leaving the leash to pull me along. The second we stepped out into the store I felt like everyone was watching me, like a circus animal. I caught up to David so the leash was less obvious but that did little to save me from embarrassment. We walked up to the front counter and Bryan put me right in front of the Cashier. "I'm sorry for forgetting," Bryan apologized, "but my girl wanted to wear something out. Can you charge this too please?"

"Sure," the cashier girl responded, "Where's the tag?" I looked around. It wasn't on my back, nor was it on my sides. I looked around helplessly until it hit me. "Amy, would you please show the lovely lady the tag," Bryan urged.

With shame I looked down, both for coordination and to avoid eye contact. I grabbed the end of my skirt and pulled it up. There it was the tag was right next to my poorly tucked away secret. My face went red. "Oh," The sales lady said in shock, "well, I certainly wasn't expecting that." She scanned my crotch, I mean the tag, and charged up the sale. I was nearly embarrassed to the verge of tears. "What do we say sissy?" Bryan asked.

"Thank you," I murmured.

"No problem sweetheart," the sales lady said with a wink. With my pride in shreds Bryan walked out of the store, pulling me behind him. I once again clung to Bryan's arm, but this time to hide rather than for comfort. For all I could care, the less of me in vision, the better.

The long walk back to the car was scattered with catcalls and whistles. Bryan required me the say thank you every time that happened, which was the exact opposite thing I wanted to do. One person followed us out of the mall before Bryan gave him a glare and he ran off.

I don't know if my skirt covered my butt or not, but it sure didn't feel like it. At least 99% of my leg was showing and while the swimsuit looked like a tank top, that didn't mean it wasn't revealing. I constantly double checked my chest to make sure as much as possible was covered.

Despite my lack of back pockets, Bryan still fondled with my butt in front of everyone. He asked me to thank him for that too. The entire trek to the car was full of "Thank you sir" and "Thank you for groping me" and even once "thank you for spanking me in front of that group of girls" (they all laughed, one even cheered me on).

Finally, we made it to the car. We both got in and Bryan started driving, but that didn't mean my time of complete obedience had ended. Bryan lowered his waistband and gestured downwards. I knew what he wanted, but that didn't make me want to do it. I mentally prepared myself, I'm still a man and straight, I just need to get through 25-ish minutes more of this and I'll be all good. Yeah, 25 minutes of endurance, easy.

Before he got too impatient, I tied my hair into a quick ponytail and lowered my head into his crotch. I'm glad I kept a hair tie with me. His musky scent took over my sense of smell, while his long shaft took over my vision. He wasn't hard, but that didn't mean he wasn't huge; I kissed the head and started rubbing the base with my hand. I slipped the whole thing in my mouth and used my free hand to play with his ball. Slowly, he inflated in my mouth, till I couldn't hold him no more.

At this point he turned on some music. Nothing intense, but some loud pop with a heavy beat. I started bobbing my head to the music. After finding a rhythm I would focus on my tongue and try my best to stimulate him. "Stick your tongue out," Bryan instructed. I did what I was told and continued bobbing. Bryan put his free hand on my head and pushed me down. My nose hit his pewds and my throat was filled with cock. I couldn't breathe! I choked on him for a minute before he let me up. I took a big breath and inhaled his sweat.

He kept his hand on my head and occasionally forced me to deep throat. I lost track of time, but we were still going at it 5 songs later. Did he have endurance or what. I decided to end this A.S.A.P. so I really got enthusiastic and tried to bring him to a climax, but his response was the last thing I expected. "Hey, could I get double bacon cheeseburger and some fries," Bryan ordered. When did he pull into a drive-thru?

I tried to pull out, but Bryan kept my head down with his right hand. "Bryn Wt hm you ding?" I asked with a mouthful of meat. "Getting a snack, keep your head down or he might recognize you," Bryan suggested. I wasn't in a position to argue. "I didn't say stop!" Bryan corrected

"Bu--"

"No buts girl, no slowing down." I reluctantly resumed bobbing my head while stroking him. He pulled up to the window and nearly broke the dude with his food. Looking up I saw the shocked expression on his face, like a deer looking into headlights. I giggled a bit but kept going. "Get yourself a girl who understands her place," Bryan taunted. The boy quickly nodded and charged his card, Bryan then grabbed his food and drove off.

My heart was pounding. Wasn't that guy from our high school? I hope he didn't recognize me. My life would be over if word of this bet got out.

I continued pleasuring Bryan for a few more songs before he stopped the car in a dark residential area. His cock popped out of my mouth, "What are we doing here?" I asked.

"Get in the back seat now, it's time for that surprise I talked about earlier." Hoping for another cash prize like I had received earlier, I quickly crawled over the center console into the back. Bryan stepped out of the Mercedes and opened the back door. Once he stepped in, he pounced on me and we started making out.

Our tongues were quickly dancing while he took off my shoes. I wonder what was wrong with my shoes. He then started feeling me up and I returned the favor. My hands felt up his chest and traveled around his shoulders. He moved down to my butt and started groping me with one hand. The other hand shot into my mouth. He told me to suck on it, so I did. Then he started kissing me again and brought that hand to butt. He pulled the swimsuit to the side and slipped his hand up my rectum.

I didn't even flinch, I was used to things up there before. He slowly added fingers while I let him explore my mouth. Eventually he had all 5 of his fingers jammed up there, I almost felt proud. He then reached into the seat pocket and pulled out some lube. He probably had a plug or something for me. "turn around," He directed. I turned away from him and stuck out my booty. With his clean hand he grabbed the back of my head and pushed it to the cushion, leaving my butt in the air.