A Lost Bet Leads To Sissification

A bit of a back story to start. Ethan and I had been friends since we were young. We were always really competitive in everything we did, whether it was sports or video games. We'd often get ultra competitive and make the loser do humiliating things. We'd call them "humiliation bets". I remember on one occasion I had to get a wedgie and another when I had to kiss Ethan's bare ass. For whatever reason, I always secretly enjoyed being the one humiliated, but Ethan never knew. We were always really close, and often watched porn together. He had a more athletic build than me, and I was more a petite feminine frame.

Fast forward to our Sophomore year of college during the Summer. We were hanging out at his parent's place alone. His parents were away on vacation, and his sister had just left for a girls trip.

We were up playing Halo and talking the normal trash, when suddenly Ethan turned to me. "Let's make this interesting, loser of the next game gets a huge wedgie."

I was always up for a humiliation bet, so I figured what the hell? "You've got a deal. But let's make this a little more interesting. Loser strips down and puts on your sister's underwear for the wedgie. Bra, thong, and tights with the garter belt I know she hides from your parents." I smirked slyly, implying his sister was a slut.

I knew I was the better player, so I figured Ethan was going to end up in women's underwear wincing while a thong string was splitting his ass cheeks. Despite me being the better player, Ethan agreed. He was playing better that night, but I knew my luck was about to change.

A few minutes go by and somehow I manage to lose; I suddenly felt very sheepish. I was sweating, "Am I really going to have to strip down and put panties on?"

"That's right loser," Ethan replied, "strip naked and throw those underwear on, and don't forget the bra and tights. I can't wait to see those bare butt cheeks in a thong!"

I was better than him at Halo, I knew I could win if we played again. I begged him to compromise "What if we played again for double or nothing? I'll do something really humiliating if you beat me, and we can call it even if I win?"

Ethan quickly fired back ,"You've got a deal, but instead of just the bra and panties I want you to completely shave your body and put makeup and a wig on - I want you to look like a woman. Oh, and instead of a wedgie, if you lose you have to suck my dick."

Oh my god, I thought to myself, this would be so humiliating if I lost. This was way more than we ever risked in a bet! As I was thinking about what would happen if I lost, I started getting aroused! I couldn't believe it, but I was getting turned on by the thought of having to blow Ethan. As blood was rushing to my cock, I noticed Ethan glanced down. I quickly repositioned myself, and agreed to the new bet, knowing I was the better player and the first match was a fluke. Despite my arousal, I was still nervous to play. I hesitantly picked up the controller, my confidence was gone thinking about where my mouth would be if I lost.

And it wasn't even close... Ethan dominated the match. Now it was time for me to pay up... I can't believe this was happening, how could I lose?! But did I secretly want to? My cock continued to stiffen and Ethan definitely noticed.

"I'll go pick out the panties that I want you to put on, meet me in the bathroom," Ethan ordered. I went into the bathroom like I was told, and there was a razor and shaving cream waiting for me. Ethan met me in there and dropped off a black lace thong, black lace bra, and the thigh high tights with the garter belt.

I spent a while shaving my whole body including my ass and cock and balls. By the time I was done, I felt feminized being completely hairless. Ethan then helped me put makeup on, and he found a blonde costume wig in his sister's closet. It was a short bob wig that just touched my shoulders. For makeup, he chose bright red lipstick to put on my lips. After watching his sister all those years he knew what he was doing, he even used heavy eye shadow and bronzer on my cheeks. I sat there in amazement as I was being transformed into a girl by Ethan, the victor in our little bet. After he finished, I turned to the mirror and was amazed at how much I looked like a girl. I hardly recognized myself!

I must have been staring for too long because Ethan suddenly said, "Come on, let's go to the living room. And you're my sissy bitch now, so make sure you crawl in here on all fours."

'I'm his bitch now?' I thought to myself ' This wasn't part of the bet!' But for some reason it excited me to be ordered around all dressed up as a woman. I felt myself starting to get erect in my panties as I got down on all fours. I would never have admitted it to Ethan, but I was excited to be dressed as a woman and ordered around.

I finished crawling on all fours into the living room, when Ethan started taking off his shirt and pants. I crawled in front of him and anxiously waited, staring at the bulge in his pants. As his pants slipped off, I could see his big erect cock through his underwear. It must have been 7 inches and girthy. He slowly slipped his underwear off and his cocked popped out right in from of my face; oh my God it was huge! I was pleasantly surprised as he was completely shaven as well. I had a feeling I was going to have his nuts in my mouth, so at least I wouldn't have to swallow any hairs, I thought to myself.

"Alright, you ready to know what losing tastes like?" Ethan taunted. "I want you to gag on that cock. Don't forget to worship those balls too."

"Yes sir," I said without even thinking. Oh my god, I thought to myself, did I just say 'yes sir' to his command?

"That's right bitch," he quickly replied, "you're going to do exactly what you're told, and you're going to like it." He could clearly tell how turned on and submissive I was as I was 6 inches away from his dick.

As I looked down, my penis was fully erect in my panties as I turned to face the big bulging head of his cock. He knew what he was doing, probably from seeing my erect cock earlier. He knew he was going to get to degrade and humiliate me with his cock, and I would beg on my hands and knees for him to do it to me.

"Start sucking, no hands either"

I opened my mouth and started sucking his cock. It was so huge in my mouth as it went back and forth past my red lips. After about a minute of me sucking, Ethan took his cock out and placed his hands on the side of my head. "Hold still, and stick your tongue out. I want to hear you gag on it."

"Yes sir," I responded, completely ok with my submissive position.

He started shoving his fat cock into the back of my throat. I couldn't help it, my mouth and throat started making gagging noises "glug glug glug glug".

"That's right, suck that cock bitch. I want you to taste my big alpha cock. This is what happens to losers." Ethan said as he face fucked me like a bitch. I couldn't believe I was on my knees worshipping his big cock like a complete sissy beta bitch. My small penis was so hard from being used by his big juicy cock.

"glug glug glug", I gagged some more. He then pulled his big cock out of my mouth and I instinctively start licking and drooling all over both sides of his large veiny penis with my tongue out like a cock hungry slave. I stop at the top of his cock and he orders me to swirl my tongue around the tip of it.

"Lick that tip like a lollipop, bitch."

"yes sir" is all I reply before I lick his pulsating head. I think I taste some precum as I slurp down the head.

"Open back up"

"glug glug glug glug glug glug glug"

"Keep that fucking tongue out slut" He said, degrading me further as I continue to worship his amazing dick.

He interrupts my response " yes s-glug glug glug glug glug"

I gasp for air as he pulls his cock out. "Oh my god!" I instinctively moan. Lines of my spit were still connected from my tongue to his hard shaft. Why do I love being humiliated so much by his big cock I think to myself. My mouth stays open awaiting my next chance to gag on Ethan while he uses my throat.

"Break's over cock slave" he says seconds later.

"yes s-glug glug glug glug glug".

He quickly pulled his meat out from my mouth. I thought he was giving me a reprieve from my degradation, but he then smacked his saliva soaked cock all over my face.

"Stick that tongue out" he orders commandingly as he slapped his dick on my red lipstick covered lips.

"Back in bitch, open that mouth wider and stick that tongue out!"

I do as I'm told and open my mouth wide, sticking my tongue out ready to taste more of his fat, juicy cock, "glug glug glug glug glug glug"

So much spit was dripping down my chin and onto my panties and penis from having my face used like a fuck doll. My penis was much smaller than Ethan's, but it was so erect as I was being made into a cock sucking bitch. Oh my God, I couldn't believe that I loved being dominated so much by Ethan! My thoughts were interrupted as he pulled his cock out of my mouth.

"I want you to admit you love being my sissy cock sucking slave."

My hard dick pulsated as I uttered the words, "I'm you're cock sucking sissy bitch Ethan, I love being dominated by your cock! Own me, degrade me, Ethan! I'm you're fucking bitch and I'll do anything you say Ethan!" I couldn't believe I was on my knees worshipping Ethan's big throbbing cock, and I couldn't believe how much I loved being humiliated by him!

"Good," he replied, "now suck on my balls. Before you do, I want you to admit I've got the alpha cock and balls between us."

I looked down at my small package and then back up to Ethan's big throbbing cock a large ballsack, and I quickly uttered, "You've got the alpha cock and balls, Ethan. Thank you for letting me worship it. Oh God make me your bitch!"

I then did as I was told and got lower on my hands and knees and starting licking his balls. He grabbed both his nuts and told me to open wide as he slipped both of them into my waiting mouth. As I was cleaning them with my tongue, saliva covering them completely, his spit covered dick rubbed all over my face.

To assert his dominance more, he then grabbed my panties and pulled them tighter into my ass crack as I let out a faint moan.

"You like that bitch? You're humiliation hasn't even begun." He then pulled his spit covered balls out of my lipstick covered mouth and proceeded to rub them all over my face. "Keep your tongue out and keep those eyes open, I want you to see these balls rubbed on your face. And don't worry, I'm not going to ruin your makeup."

"thank you, sir," I replied as I watched his nut sack smear spit all over my face.

"Now, it's time for some nostalgia. Remember when I made you kiss my ass, well I think you need to get reacquainted. Lay flat on you back."

I did what I was told as I saw Ethan rubbing oil all over his smooth, shaved bare ass. I was so turned on at what was about to happen. My cock continued to throb thinking about how he was going to humiliate me with his butt cheeks. He held my arms down and placed his ass crack right near my face, then sat down. My nose and mouth split his butt cheeks apart. He then started sliding his cheeks back and forth, using my face like toilet paper.

"Now, stick your tongue out, I want you to lick my asshole and balls from down there." I stuck out my tongue and started licking up and down his ass crack all the way down to his balls as he slid up and down my face.

"Good, now eat my butthole out like the sissy bitch you are." Ethan commanded.

I tongued his asshole feverishly as I wanted to be obedient. I could taste that it was freshly cleaned as I continued to lick and tongue it. He suddenly pushed my head into his cheeks,

"Take a big whiff, I want to hear you breath in deeply." He ordered.

Oh my god, I couldn't believe he was making me smell his ass. I continued to be humiliated and breathed in deeply to show him I'm his bitch. This was another move to assert dominance, which I complied to, making my cock somehow even harder. His ass smelled clean, but I still felt embarrassed at having to smell it. I then continued licking his butthole in subservience.

Suddenly he stopped and dropped his balls into my mouth, teabagging me as I stared at his butthole. I was so turned on by how he was using me. He kept bringing his balls out of my mouth and commanding me to keep it open as he dropped them back in.

"Lick those ass cheeks too, sissy" Ethan remarked.

"Yes sir" is all I replied as I tongued up and down his cheeks and into his ass crack between my teabaggings. Finally, he told me to open my mouth wide as he plunged his cock back down the into my throat. With his dick deep inside me mouth, his soaking wet balls rested right on my nose.

"You want to smell that nutsack too bitch?" He taunted. As I started to gag, he pulled his dick out and rubbed his balls on my face once more. I kept my tongue stuck out in anticipation of him wanting me to have to taste his balls and asshole more.

"That's enough ass licking and ball sucking for now. Are you ready to really become my bitch?" Ethan asked.

I knew what he was going to say next, he was about to tell me that he was going to butt fuck me. Spit and cock juice drenched all over my face, I was ready to get in any position he told me. He fucking owned me, I was his cock slave ready to worship.

"Get on your knees with your ass stuck up in the air, and lock your hands behind your knees. I'm about to fuck your ass and make you into my sissy bitch for good."

I did what I was told, got on my knees and anxiously awaiting my fate. I must have looked like such a sissy bitch; my legs in tights with a bra and panties on, waiting to take a cock in my ass on the living room floor.

He briefly left the room and came back with another bottle of oil. He immediately pulled my thong to the side and started lubing my ass cheeks up as well as rubbing the oil on his cock. "Are you ready to get that tight butt hole stretched out?" He asked.

"Yes sir, I'm ready for the ultimate humiliation. I'm ready to have my tight butthole stretched and dominated by your big alpha cock." My penis was so erect as I prepared for what was next.

He stood over me and squatted down to begin his next act of domination. I was on my knees with my face on the ground and ass in the air as the head of his cock started to push against my tight asshole. I let out a slight girly moan as his dick entered into my ass. It was so big I couldn't help moaning as it stretched out my ass. Once he got it in, he started to pump a little faster,

"You like that sissy bitch? You like getting your butt hole stretched out by my big alpha cock? Tell me you're my bitch and you like it!" Ethan said.

I did whatever he told me, I was his complete bitch now and he owned me with his big cock pumping my ass. "I love it sir, stretch my asshole out with your big alpha cock! I'm your sissy bitch Ethan! I'm you're sissy bitch! Oh my God!"

I was being completed dominated, he was standing over me fucking my ass while I had my face in the carpet and ass straight in the air taking it's pumping. It was so humiliating but I loved being his sissy bitch! I'm being butt fucked and dominated while dressed as a woman!

As I was in ecstasy about my new sissification, he suddenly commanded me, "Spread those butt cheeks bitch!"

I quickly grabbed my ass and spread it wide with my painted nails digging into my cheeks. I was ready to continue being owned and having my oiled ass taken. I continued to spread my butt cheeks wide and get pumped.

"I'll spread my butt cheeks wider for you, daddy!" I admitted like a sissified and owned slut, "Please stretch my ass out with your huge alpha cock!"

After about 30 seconds of him butt fucking me, I couldn't stand it any longer "Ethan, I'm about to cum from being butt fucked like a bitch!"

"Not yet you aren't," Ethan remarked. "Crawl to the couch and put your head on the floor and your back on the couch, so your feet are on the floor over your head."

I did as I was told and he grabbed my legs to get me into position. My head was on the floor and I was looking up directly at my own dangling erect cock, and my ass was pointed up in the air exposed, ready to submit to his girthy cock again. He stepped over my feet and head, and got into position to continue my ass pounding. All I saw were his ass cheeks and big cock as I felt him enter my ass again.

"Oh my God, Ethan!" I gasped as I watched him pumping away and felt him stretching my ass out more.

I told him again, "Ethan, I can't hold it in much longer!"

"I know," he said, "when you're cumming, I'm going to point your little sissy cock at your face, and you're going to give yourself a facial."

I couldn't hold it any longer after thinking about how degrading being forced to facialize yourself is. He plunged his thick cock further into my ass and kept it deep as I moaned in ecstasy.

He grabbed my sissy dick and I shot a huge load onto my face. I couldn't stop shooting cum as it landed all over my forehead, eyes, mouth, and cheeks. I had never cum that much before! Even more surprising, my cock stayed erect after shooting cum all over my face!

He slowly pulled his cock from asshole as cum ran down the side of my face and some into my mouth. "You're not done yet. I want you to come clean off my cock. Stick your tongue out too, because I want you to taste your own ass."

My cock began to stiffen more at the thought of ass to mouth, something I'd only seen in degrading porn movies. I opened my mouth wide, with my tongue sticking out as I was told.

He suddenly grabbed the sides of my head and started face fucking me like before "glug, glug, glug, glug, glug, glug" I gagged. He suddenly pulled his big juicy cock out of my mouth, and said without thinking, "I'm your ass to mouth bitch, Ethan! I'm your cock sucking slave!" My cock was already completely hard again even after spewing cum all over my own face.

He quickly responded, "Good, now time for me to finish up. Get on your knees and elbows. You're getting butt fucked again, and then I'm making you swallow my big load."

With my face still dripping with cum, I get in position right away. Before he enters me, he grabs my panties from earlier and rubs them down my ass and all over my balls, collecting some of the oil from earlier. He then proceeds to tell me to open my mouth as he jams them in. He continues to stand over me as he squats down and enters my ass again.

After two minutes of fucking me while I'm gagged with ass oil panties, he finally pulls the panties out of my mouth. He then pushes my head onto the floor, and I get into the same submissive position I was in before by grabbing behind my knees. He then puts his foot on my face in a final show of dominance and humiliation.

"Who's my sissy bitch?" he asks.

"I'm your sissy bitch Ethan, please butt fuck me and cum in my mouth! I want to swallow your big alpha load!" I exclaimed. I couldn't believe the words that were coming out of my mouth. I wanted Ethan to degrade and humiliate me in every way imaginable.

After a few more pumps, he pulls out and has me get up onto my knees. "Alright bitch, open wide for my load! And keep that fucking tongue in your mouth because I want you to gargle it before you swallow!"

'Oh my God', I thought to myself, 'He's going to make me gargle his load before I have to swallow it!' Without thinking more, I open my mouth as wide as I can, and he starts shooting a huge creamy load into my mouth. As he's moaning, it seems like he's draining all of his balls into my waiting mouth.

I start to tilt my head back as his huge load is filling into my mouth. He finally stops, and commands me to gargle it before swallowing it all down. I couldn't believe it. I was staring up at him as I was gargling a load of his semen. It started to bubble over, but he didn't tell me to swallow yet. I continue gargling for another minute, taking breaks to swish his load in my mouth as my own cock continued to pulsate from the humiliation.