Samantha and the Dare

Literotic asexstories – Samantha and the Dare by Samantha_Sherman,Samantha_Sherman Vincent was coming to town for the weekend so I invited him to stay at my place. We only get to see each other a few times a year since he travels a lot for work. When he gets tired of the rat race and wants to let his hair down, I am his first call. Vincent’s timing couldn’t be more perfect.

Vincent is my big brother. He’s two years older than me and ever since we were kids, we’ve dared each other to do pranks and stunts and other stupid things. Over time, we developed a magnetic animal attraction we could not deny and the dares were mixed with sexual favors. The dares and favors became more elaborate and sometimes even we would cringe just thinking them up. Vincent is my evil twin.

I called my friend Keli to let her know Vincent was in town. She cleared her schedule so she could be available for the weekend. I told her what I had planned for the dare and asked if she was interested. She gave me a big smile and said, “Bet. Text me when you’re ready.” I texted her Vincent’s flight number and she would bring him here.

Keli is a professional driver and former Marine. At six feet tall, Keli is a tall, athletic, muscular girl; fit and toned like a real-life Warrior Princess. She’s a blue-eyed brunette, just like my brother. She provides car service and security. It’s comforting to know she is nearby when Vincent and I take one of our walks on the wild side. This time she would help me get my revenge.

We hadn’t seen Vincent in a few months, so Keli stopped in to visit. I was so happy to see them both. They actually looked like they would make a good couple. We chatted for a while to get caught up until Keli had to go. That left time for me and Vincent to discuss the dare. Last time, it was Vincent’s turn to dare. He took me to a motel next to the truck stop and sold my pussy to truckers all weekend. I had more cum shot into me in those three days than I had the rest of my life combined. This time it was my turn to dare. I figured that turn-about is fair play, so he would be my whore this time.

The standing deal between Vincent and I was that once you accepted the dare, you could not turn back. I will never forget the time he dared me to steal a cop car, 100% sure that I would not do it. He was wrong. We jumped in the car and I drove it like a NASCAR driver at the Daytona 500! What a rush! I drove it out to the woods where nobody would find it. We were on an adrenaline rush and when I stopped the car, I thought we would explode.

We jumped out laughing hysterically! We raced around to the front of the car where I leaped into Vincent’s arms for a passionate kiss. We could no longer contain ourselves. Vincent put me down and bent me over the hood of the cop car, yanked my pants down and fucked my brains out. Oh, God, the adrenaline rush and Vincent’s big dick pounding away at my wet slit brought me to a stunning climax! I laid forward on the hood of the car, my pants and panties pulled down around my ankles as my body convulsed in orgasm. It was incredible!

Vincent called somebody to pick us up and we were long gone when the cops found the car two days later. That remained our benchmark scene for years to come.

I had been working on this new dare since I swallowed the last load of truck driver cum three months ago. I was going to dare him to be my sissy bitch sex slave for the weekend. We ordered in and chatted away over some Chinese food. Our chat finally came around to the dare.

“Well, Sam. It’s your turn.” was all he said.

I stood up and walked around him, hands behind my back.

I said, “I dare you to be my submissive sex slave for the weekend. I will be your mistress and you will be my slave. You will comply with my every command or suffer my wrath. Do you accept the dare?”

I intentionally left out the word “sissy” so as not to tip him off. I was sure he figured he would spend the weekend kissing my feet and getting his ass paddled, but he couldn’t be more wrong.

Vincent said, “Sure, sis. You’re on. I will submit to you, my mistress, and become your slave.”

“Pinky swear.” I said and we shook pinkies, sealing the deal.

I texted Keli and told her we were on. She would get the room ready and pick us up later. Meanwhile, I would dress up my brother as a pathetic sissy and doll him up so he looked good enough to fuck.

“Slave!” I yelled, “Get your ass over here!”

He stood and walked over to stand in front of me.

“Eyes down, slave! You do not look your mistress in the eye. You will address me as mistress do you understand?” “Yes mistress” he said, eyes down.

“Good boy. Get undressed, slave, and make it snappy. Hurry!”

Vincent is a handsome man, tall with dark hair and blue eyes. He has a tall, fit body and a good-sized dick and I can’t get enough of it. He stripped naked.

“On your knees, slave! Your most important reason for existing is to please your mistress and you can start right here.”

He said, “Yes mistress.”

I lifted the hem of my sundress with my right hand and grabbed his hair with my left.

I forced his face into my crotch and said. “Eat it slave!”

He reached around and grabbed my ass cheeks with both hands and held me in place while he ravaged me with his tongue. My brother was very skilled and he had me cumming in minutes.

“Oh! Vince! Fuck yes! Ohhh, yes, eat me! Uhh. Mmm. Oh! Oh! Vince! Mmm…oh…oh…oh.”

I screamed and moaned as I orgasmed, creaming his face with girl juice. I held his face there, my body quivering, until my orgasm subsided.

I pulled him away from my cotch and said, “Well, slave, I suppose that will have to do. Now get your pathetic body in the shower and scrub it. Shave off all that nasty hair off while you’re at it. All of it! Mistress will not take you out with that filthy hairy body. Your outfit is hanging in the closet. You will be dressed and sitting on a pillow on the bed when I come in there. You have one hour.” I slapped him on the ass and yelled. “MOVE IT!”

“Yes, mistress” he said, and off he went.

Vincent wasn’t sure what Sam had planned. She could dream up some bizarre shit, and she had an evil streak too, so he was a little apprehensive. He needed a quick shower anyway. Knowing Sam, he had better hurry or risk getting his ass paddled. He toweled off and looked in the closet. It was completely empty except for one single hanger with an outfit on it and a pair of black pumps on the floor. It was a black dress and crotchless black pantyhose. Vincent put on the clothes and they fit well, kind of comfortable, really. Even the shoes fit. His package was hanging out in plain sight for anyone to see. He sat on the pillow just as his sister walked in. Vincent’s chin dropped. She was wearing a crotchless black leather teddy with fishnet bodysuit and platform boots. She had a long leather riding crop sticking up out of her left boot, and she was wearing make-up. Sam never wore make-up.

Vincent thought ‘Holy shit! Look at little sister!’

I said, “Good boy, or should I say good girl? Sit here, bitch.”

I pulled out a chair for him at the vanity, facing away from the mirror. “Well, if you’re going to dress like a bitch, we need to pretty you up. Now let’s see what we can do with that ugly face of yours.”

I pulled his long hair back into a ponytail and looked at his face.

“Mmm-hmm. I see the problem right here. An ugly bitch like you needs lots of make-up. Sit still.”

I really overdid his make-up and put on enough to make him look like a two-dollar whore. “There we go. Now you are REAL pretty. The guys are going to love you, bitch. Your new name is Sissy. You are my little bitch, Sissy.” She kissed him on the lips and said, “Oopsie, I almost forgot the lipstick! Look here Sissy, look at me.”, and she grabbed his face and held his chin. She got out a gaudy shade of Cocksucker Red and said, “Here we go, Sissy.” And she painted his lips in a Joker-esque style. “Now that is MUCH better. That’s a good color for you, bitch. Cocksucker Red.” She brushed his long hair and turned the chair so he could see himself. “Now that you are a pretty bitch we can go to ladies night. Well, Sissy? What do you think?” Vincent looked in the mirror and Sissy looked back.

Vincent thought, ‘Holy shit! What the fuck did I get myself into?

I said, “Well, Sissy? What do you think? Tell me!”

Sissy said, “Yes, mistress, I am very pretty. Thank you, mistress”

I said, “Well, what are sisters are for Sissy?”

I walked to the bed and said, “Come, Sissy. I have some accessories to go with your outfit.”

I picked up a couple things from the dresser and put one around his neck — a ball-gag, and another one on his head, a blindfold. I put my arms around his neck and looked into his eyes. I held his head and gave him a big kiss on his obscenely red lips, slipping my brother some tongue, lipstick transferring to my lips.

I said, “Just one more thing Sissy and we’ll be ready to go. I put the ball-gag in big brother’s mouth and slipped the blindfold in place, I sat down on the bed and reached under Sissy’s dress to feel up her cock and balls.

“Mmm…Sissy. What a nice package you have! The boys are going to love this!”

Sissy’s cock was hard as a rock and I was slowly stroking it up and down, up and down, over and over. I put my mouth over the head of my brother’s cock and licked the underside of his head, getting lipstick all over it. He moaned against the ball-gag and exploded in my mouth. I caught most of it in my mouth and the rest dripped down my chin and down the front of my new teddy.

I yelled, “God-dammit, Sissy! Look at the mess you made all over my outfit!”

I stood up and grabbed Sissy around the throat and backed her up against the wall. Sissy landed against the wall with an, “Oommf!” and I continued berating her.

“I can see we are going to have to take special measures to make sure your pathetic, tiny dick doesn’t go off again!”

I pulled the riding cop out of my boot and it made a loud “Slap!” as it landed squarely on his freshly shaven nut sack.

“Mmmmmphf!” shouted Sissy, still blindfolded, the ball-gag doing a fantastic job.

Vincent thought, ‘Holy shit! Little sister isn’t fucking around! She is punishing my sissy ass already and we haven’t even left the house yet!’ Just the thought made him cum again, he simply could not stop himself. He shot cum all over my outfit.

This time I pulled off the ball gag, grabbed him by the hair and said, “Lick it off, bitch! Lick your cum off your little sister!”

I dragged his mouth all over the front of my leather outfit making him lick up every drop. I was bitching the whole time but Sissy didn’t hear it, she was in heaven being forced to lick up her own cum by her little sister, the closet psychopath, punisher of men. I was going to have fun with Sissy all weekend if it killed her.

I pulled Sissy’s head up and said, “Stand up, bitch. Be still!”

I slid the riding crop back in my boot and let go of Sissy’s throat and pulled up the blindfold so she could see. I picked something up from the dresser and sat on the bed.

“Come here, Sissy.”

Sissy moved to stand in front of me and said, “Yes mistress.” ”

Well, I figured you wouldn’t be able to control yourself since you are just a pathetic sissy bitch, so I picked up something just for you. Come closer!”

She had a pink cage-looking thing with a lock on it.

Vincent thought ‘Oh God, a cock cage. My little sister is locking up my dick in a cage!’

I turned the lock, showed Sissy the key and threw it in my mouth and swallowed it. Sissy opened her mouth and then shut it. I laughed at her dismay.

“Sit, Sissy. Keli will be here soon.” Clearly Sissy was going to have an interesting weekend!

Keli was happy to have a weekend off, especially since Vincent was in town. She loved getting together with him and Sam whenever she could. Keli thought Vincent was hot, but she was too shy to say anything. He was a big guy, taller than her, and she found that attractive. She was happy to be around him. She never knew when he would be in town and it was always interesting when Sam and Vincent got together.

Keli knew about the last dare; she couldn’t believe Sam actually went through with it, but Sam does not back down from a dare. Sam had been planning this new dare for months and the timing couldn’t have been better. There was a popular annual leather party all weekend at Ramrods. Tonight was Sissy Night.

Ramrods was a popular destination for a diverse and eclectic swinger crowd and this weekend’s event was one of the largest of the year. Keli knew the place and had visited as an escort on numerous occasions. At Sam’s request, she planned with the club for a room for the weekend.

They were high dollar, two-bedroom luxury suites where clients and entertainers would stay. Sam wanted a fully equipped room and Keli made it happen. Keli had just checked the place and it was secure. She chatted with the manager, Frank, about tonight’s event. They had the usual gear on hand, a wide selection of bondage equipment. Since it was Sissy night, they had plenty of glory holes set up. A challenge was set up for midnight, with the top three sissies to suck the most cocks qualifying to compete in the.

Keli had time to run home, get a bath and grab her go-bag. She would be Sam’s escort and she was looking forward to a wild night. They rarely had trouble at these events, so Keli could cut loose a little. The bath was warm and inviting, and Keli stretched out in her long tub and leaned her head back. She was excited about tonight. Going out with Sam and Vince was something different and she needed a break from her hectic routine.

She scrubbed her body from head to toe and felt the day wash away. She ran her hands over her body and a shiver ran down her spine. She hadn’t cum in a week and she was ready. Her hands wandered to her breasts, rubbing them and pulling her stiffening nipples. Her breath caught, and her hands slid over her belly to her aching pussy.

Her vagina was open for pleasure, and her little man was stiff as a rail. She dipped two fingers into her slippery hole and used her other hand to stroke him.

“Ooo…mmm…ohhh…mmm”, she ran her fingers up her slit to the base of her clit and rubbed it while her other hand jacked it off. “Mmm…mmm…ohhh…ohhh…oh!.” she was going to cum quickly with the double stimulation of her rock hard 4-inch clit she called her ‘little man’. Keli moaned and drew her legs up and apart and her abs started spasming as a full-body orgasm rocked her long, tall body.

Her fingers kept stroking as her muscles clenched and relaxed, over and over until she peaked. She grabbed the sides of the tub and sat up, arching her back, head tilted back.

She moaned loudly, “Ohhhhhh…mmmmmmmm…ohhh, YES!” her body trembling until her orgasm subsided.

She laid back. “Oh my God! Mmmmmm.” she said and she relaxed once again. It was time to get dressed.

Keli was wearing a corset with suspenders and stockings, a mini-skirt and thigh-high boots. All black leather, of course. Even though she was six feet, she wore her four-inch platform boots, making her just a little taller than Vincent. She wanted to get his attention tonight, and this outfit would do it.

When Sam became Mistress Samantha, her transformation was stunning, like night and day. Sam immersed herself into the role and became Mistress Samantha, punisher of men. She was a highly regarded domme in the local community and was gifted at extracting the maximum amount of pain from an individual using any number of methods and implements. Tonight was Sissy Night and Vincent was going to be the star. The fact that Sam and Vincent were siblings made their scene especially provocative.

Keli couldn’t wait to see Sam in action again. She could only imagine what poor Vincent was going through and she smiled. Her phone buzzed. It was time to pick up Mistress Samantha. She wanted to get to Ramrods a little early to check the room.

“Sissy! Come here!” Samantha yelled. Sissy was there in an instant, eyes down.

“Yes, Mistress Samantha.” Sissy was starting to get with the program.

Vincent was quite the sight, wearing his little black dress and his crotchless pantyhose and that obscene bright pink cage. His makeup was hideous. It was hard to keep a straight face seeing his predicament.

“There’s my little sissy bitch. You look marvelous, Sissy. You really do.”

Sissy said, “Thank you, Mistress Samantha.” ”

“Now Sissy, I have a little gift for you, and I know you’re going to love it! Just turn around and bend over and little sister will fix you right up.”

Sissy did as she was told. Samantha reached between Sissy’s legs and smeared lube on her ass, fingering Sissy’s anus to make sure it was well lubed. Sissy didn’t move as Sam finger fucked her ass harder and faster.

“You like that don’t you, slut? Don’t you!”

Sissy moaned. “Yes, Mistress Samantha.”

“Well, you’re really going to love this then.” she said, wedging a long fat butt plug deep in Sissy’s ass. Sam pushed it in all the way and strapped it in place. It had a vibrator and light that could be controlled via remote. She couldn’t wait to light his ass up.

“Stand up, bitch.” And Sissy stood, trying to get accustomed to the invader in her ass.

“Yes, I know, right? A bitch like you wouldn’t feel right without her little friend, would you Sissy!”

Sissy moaned again. “Yes, thank you Mistress Samanatha.”

“Sissy, Keli will be here any minute. You’re sweet on her, aren’t you? Well, I think it’s only polite of you to show her in, don’t you?”

“Yes, Mistress Samantha. It’s only polite.”

“Well, that’s good, Sissy. Now you go outside by the curb and watch for her.”

“But Mistress…” Sissy didn’t see it coming. “Slap!” right across her face with my open hand.

“Sissy, are you talking back to me after all I’ve done for you today? You ungrateful bitch! NOW GO!” and Sissy hurried out the door. Sam picked up the remote and put it on a key fob with the spare key to the cage and tucked it down her cleavage. She would give it to Keli later.

Keli came around the corner and saw a hideous street walker hanging out in front of Sam’s place. On duty or not, Keli had Sam’s security in mind. She would have to check this girl out and send her on her way. She stopped the Land Rover at the curb and looked at the girl.

OMG it was fucking Vincent! Holy shit! And he was wearing a cage! Jesus, he would get arrested if the cops saw him! Maybe Sam went overboard this time. Keli remembered what he put Sam through last time, and she smiled, he had it coming. She got out and walked around the car to Vincent.

At 6′-4″ in boots, she was an imposing figure. Towering over him, she said “Excuse me, ma’am. Move along. You’re on private property.”

Vincent looked up at her and said, “Very funny, Keli. She turned me into Sissy. You knew, didn’t you?”

Keli laughed out loud, ignoring the question. “You look positively… breathtaking… Sissy.” And she laughed again. Serves him right, she thought. Suddenly, Sissy started moaning and squirming around.

“What’s wrong?” asked Keli.

“She put a butt plug in my ass. And it vibrates.” Keli laughed again.

Just them Sam came out.

She waved and said, “Hey Keli! I see you’ve met my bitch Sissy. She’s looking forward to going to ladies night with us tonight. Just three girls out looking for a good time. Isn’t that right Sissy?” Sam stepped down off the porch and stood by Sissy.

“Yes, Mistress Samantha.”

Sam slapped her on the ass and said, “Well let’s go, Sissy, get in, we mustn’t keep Keli waiting.”

Keli opened the back door and Sissy got in. Sam rode shotgun and they were on their way.

She handed Keli the key fob and said, “She’s all yours.”

‘It was still early when they got to Ramrod’s. It was in an old industrial building, with the club downstairs and rooms upstairs. Keli parked the Land Rover in the ground level parking lot near the freight elevator. They grabbed their go bags and took the elevator up to their room. It was one of those huge elevators where the entire side opens up for large loads. The room was spacious with an Industrial feel and fully furnished. The kitchen was huge, as were both bathrooms.

Sam ordered it fully equipped, so there was a good selection of gear including various stocks, St. Andrew’s Cross, sex swing, bondage chair and gynecologist’s table on hand. The gyn table was Sam’s favorite.’

I loved it, “This room is perfect! Thank you, Keli!”

I looked at Sissy and said, “Sissy what do you think of our room? There sure are a lot of toys to play with! I bet you want to play with each and every one of them, don’t you?”

“Yes, Mistress Samantha. As you wish.” she said.

Vince still didn’t really know what was going on. It looked to him like he was going to have his ass whipped all weekend. He thought, ‘Well, it could be worse than having these two fine pieces of ass whipping me all weekend.’

Sissy said, “Mistress Samantha, please show me all of the toys.”

I said, “Now that’s my girl, come with me.”

The three of us walked around and checked it out. We chatted about each item as we made our way from one station to the next. I had Sissy try out the swing and we got it adjusted to fit her. The next one was the bondage table. It was a quality table, not one of those cheap wobbly things, this one was heavy.

Keli and I got Sissy in it and all adjusted and when she was comfy, we showed her the fuck machine attachment. We could swing it down into place after she got in and swing it back up when we were done. We got it set up to go straight up her ass with a nice, steady fucking motion. The business end was a firm twelve-inch black silicone dildo. It wasn’t that thick, but from the look in Sissy’s eyes, you’d think it was a monster.

Keli and I laughed and swung the machine up out of the way so Sissy could get down. I said, “What’s wrong Sissy? You look like you’ve seen a ghost.” And we both laughed again.

Next, we fit her into the stirrups on the ob-gyn table and then adjusted the straps on the St. Andrews cross.

“Well, that’s done. Now there will be no waiting in case you need some attention later, Sissy. Come on, lets powder our noses.”

I took Vince into the bathroom where he watched me pee, waiting his turn, dancing around, and I took the opportunity to mess with him. I didn’t realize I had to pee that much. I sat straight up with my knees apart and I knew that Vincent could see. He looked from my pussy to my eyes and I smiled.

“Are you watching your sister pee, or are you staring at your sister’s pussy?” I asked. The leather teddy was crotchless, held in place by two straps. He could clearly see my blonde muff and I knew it.

“Yes, Mistress Samantha. You have a pretty pussy.” said Sissy. I stared at her for a moment and held my pee.

“Come here, Sissy.” I said. Sissy came to stand in front of me.

I said, “Kneel here in front of me Sissy. I’m going to give you your favorite treat — you little sister’s pussy.

I stood up and pressed big brother’s face against my slit, releasing the rest of my piss into his mouth. “Drink it, bitch! Drink my piss.” He drank at least a cup of piss straight out of me and licked me clean.

“Now lick it off. Lick the piss off your little sister’s pussy! What a pathetic little bitch you are!” She licked my slit from top to bottom catching every drop. I pushed her away saying, “Now hurry up, Sissy, it’s time to go.”

Keli took the go bags and put them in the bedrooms. She checked herself in the mirror. You could almost see her dark bush under the tiny skirt. She rarely wore panties, loving the freedom of going commando. She got a black leather G-string out of her bag and pulled it on. That’s better. She would flash Vincent but all he would see was panties. She walked back to the front room and Sam was there waiting for Sissy.

“You should have seen Vince, he was staring at my pussy while I was taking a leak, so I pissed in his mouth and made wipe me with his tongue.”

Keli laughed, “Oh, Sam. You are truly a psychopath.” We both laughed and Sissy came out of the bathroom.

I said, “Well finally, Sissy! Let’s go!”

Keli opened the door to the club and we walked out onto the balcony. The balcony ran around the perimeter of the club overlooking Ramrod’s main floor, connecting the second-floor suites. It afforded the perfect view of the activities below. The dance floor took up most of the club. It was packed with people dancing, many of them sissies.

I nudged Sissy and said, “Look, Sissy! Let’s go say hello.”

We went downstairs and looked around. The orgy rooms were full of people fucking and sucking sissies in every way imaginable, and just as many people were watching. There were sissies getting their asses fucked by leather guys and twinkies sucking off old men. Others were involved with couples having the best of both worlds. Cum was shooting all over the place. The sight and sound or sex filled the air along with the manly scent of cum. It was arousing. I wrapped my arms around Sissie’s neck and gave my big brother a long, sexy French kiss.

I said, “I’m horny, Sissy. What do you think? Are you up for some action?”

She said, “Yes Mistress Samantha. Your wish is my command.”

I said, “Good. Follow me.” We walked to the end of the orgy room and there was another long room. It had rows of glory holes and most of them were in use. Sissies were on their knees sucking random dicks through holes cut in the walls. We stood and watched them suck dicks and gulp down loads of cum.

I looked at Sissy and said, “Well, I found some action for you, slut. Want to join in?”

Sissy looked at me and said, “But Mistress Samantha, the cage.”

Keli and I burst out laughing. I said, “Oh, Sissy! You’re a funny girl! Sissy, there is no cage on your mouth.”

Keli put her mouth close to Sissy’s ear and said, “The thought of you sucking all these dicks turns me on, Vincent. If you suck them all, me and Sam will make it worth your while. Suck them for me, Vince, please?”

I said, “Well, start sucking, Sissy!”

I put my hand on the riding crop in my boot and she started walking towards the glory holes instead of risking another kiss from the crop. I winked at Keli. She smiled and hit the vibrate button on the remote. Sissy jumped a little and moaned but kept walking towards the nearest cock. He was going to do it! Sissy was going to suck some dick! We walked up to the first cock. It was a big one.

I said, “Here, I’ll help you suck the first one.”

The scent of men and cum was driving me wild. I could barely control myself in that sea of cocks. I had Sissy kneel right beside me in front of the largest cock.

I said, “Ooo…that’s a nice one, Sissy! You suck it just the way you like yours sucked. OK? Watch.”

I held the cock with my right hand and gave it a couple strokes. I licked up and down the shaft, the scent of cock was intoxicating.

I pulled away and said, “See? Easy. Now you try.”

I put my left hand on the back of Sissy’s head, pulling her face closer to the cock.

I said, “Open, Sissy. Let little sister feed you some cock.” She moaned again and wrapped her lips tightly around the head and started sucking it.

“Good girl. Now suck the whole thing.”, I said, guiding the cock to Sissy’s mouth and pulling her head closer.

She opened up and took the thick shaft into her mouth. She started sucking the head then plunged her mouth down the entire shaft. She held it there for a few seconds and pulled back. She started bobbing up and down on it. It looked like she was getting into it! I grabbed the hair on the back of her head and pulled her off.

I looked at her and said. “My turn, slut, don’t be a pig.”

I took her hand and placed it on my pussy and smiled. She wasted no time plowing three fingers inside my dripping wet snatch. I continued sucking while Sissy fingered my wet pussy. I was working that cock until it started getting bigger and pulled off.

“There you go, Sissy. Little sister got it ready for you, now suck it, make him cum in your mouth.”

I pushed her slutty face onto it. She bobbed up and down on it for just a few minutes and was rewarded with a big mouthful of hot sperm. She pulled her mouth back but I held it in place on the end of the spurting cock. She choked a little on the huge wad of cum and most of it sprayed on her face and down the front of her dress.

I pulled her head off and sucked out the last of the cum myself. I faced Sissy, taking her face in my hands and swapped a stranger’s cum with my big brother. His fingers in my pussy finished me off and I came all over his hand.

We stood and I said, “See, Sissy? It’s easy. Now it’s your turn. You will suck every dick in this room and swallow every drop of cum. I will tell you when to stop. Do you understand?”

“Yes, Mistress Samantha.”

Keli turned Sissy around to look at her. She took Sissy’s face in her hands and started licking the cum off. When she finished, she leaned in for a cum kiss.

Keli said, “God, that was hot. Now you suck every dick in the room and don’t forget about your prize. Watch this.”

Keli crouched down to the left of the long dick sticking out of the next glory hole. She was looking right at Sissy, her knees apart and her little black panties on display. She grabbed the dick and gave it a lick, still looking at Sissy. Poor Sissy, her hard-on was cooped up inside that cage with no escape in sight.

Sissy walked over and knelt in front of Keli, facing the glory hole. Keli rubbed the dick on Sissy’s face and Sissy started sucking it. She was really getting into it now sucking it like a pro when that cock exploded. Keli pulled Sissy off that cock and pushed her back on the floor. She crawled on top of Sissy, giving her a sexy kiss. Keli loved the taste of cum in Sissy’s mouth and kissed her passionately.

Vincent loved the cum kisses from Keli and his sister. He decided to go all-in on this dare because he figured he owed Samantha. He didn’t realize how much he loved sucking dick and eating cum. It was driving him wild. It didn’t help that Keli would vibrate his prostate periodically with her remote. He was sure he would cum if she left it on. He was hoping Keli and Sam would hold up their end of the deal, but either way, he loved being their bitch.

Keli let her up and Sissy went from cock to cock, sucking each one and swallowing the best she could. The more she sucked, the better she got. We brought Sissy into the orgy room and told her to kneel. I wrote “Cum Slut” on her forehead with lipstick and within minutes a line formed. Me and Keli chatted away, watching as Sissy sucked load after load from every cock that was shoved in her mouth. Sissy was well on her way to winning the blow bang. By all accounts, she had sucked off 47 cocks so far and there was still time before midnight. I had one more thing to do, so while Keli made sure to keep Sissy’s count up, I went to see Master Kevin.

Master Kevin was in charge of events at Ramrod’s. He was much older than me and turned me on to the scene years ago. I found the entire scene fascinating, offering an endless number of possibilities for self-expression. We could be ourselves and nobody judged. The lifestyle was where we belonged. BDSM truly is an art form. I was thrilled to be the person giving Vincent his introduction.

“Mistress Samantha! I heard you were here. How have you been?” It was Kevin with a big hug. Kevin is a tall, big, intimidating looking man. He was my mentor and my big teddy bear.

“Master Kevin! I’m so happy to see you!” I said.

We chatted for a while and I asked him about the sissy challenge. He knew we were here with a sissy and last count showed him at 50, trailing by just a few cocks. They would call it at midnight with the top three moving up to the big event — the Blow Bang Sissy Challenge. Samantha told him about the dare.

Kevin laughed saying, “Oh, Sam! You and your brother are fucking crazy! What are you putting him through next?”

I asked. “What do you have planned for the challenge this year?”

Kevin said, “Well, the finalists will be placed in stocks. They’ll have pleasure up front and punishment in the rear. Last one to tap out wins.”

I said, “Interesting. Who are the other two contenders?”

Kevin said, “Well, there’s one in the jungle room with 65, and another one who’s been in the glory hole room all night at 69.”

“Wow. OK, Kevin. I’ll see you in a few.” I gave him a kiss and went to see how Sissy was doing.

When I found Keli and Sissy, they were still in the orgy room. Sissy had a cock in her mouth and one in each hand and she was in the whore zone. Keli was looking at him like a proud mom at a cheer-leading competition.

“He’s in the top three,” I told Keli “third place.”

Keli said, “Well, these guys have been tag-teaming him like this, maybe he’ll catch up.”

I said, “Maybe so, but he has to go the extra mile to win the challenge.”

The three guys Sissy was working on backed off and shot wads of cum all over her face and hair. She was a mess. She was pulling another cock towards her mouth. I had to give her a break.

I yelled, “Sissy! Put that dick down and get over here.”

She stood up and walked towards us. What a sight! She had cum all over her face, hair, dress — even her shoes had cum on them. Her make-up was smeared giving her a look somewhere between Alice Cooper the Joker. Her caged dick was dripping as if he just shot a load on himself. His taillight was shining out of his ass. The crowd actually applauded when she stood and walked towards us, so she threw her arms up in a V. Keli and I looked at each other and back at Sissy and cheered him on with the crowd. We were impressed!

I said, “Are you OK, Sissy?”

“Yes, Mistress Samantha. What do you think of my newfound talent?” I asked.

I told him, “Wow, Sissy, we are impressed! You are one amazing cock sucker! How long have you known?”

“I guess my whole life. I just didn’t want to admit it. I’m bi like you, Sam. It must run in the family.”

Keli said, “You know, we always suspected. You could have come out to us at any time. I thought you knew us well enough to trust us.”

“It wasn’t that easy, at least not for me. And while we’re digging up bones, here’s another one. I love you Keli and I always have.”

Keli grabbed his face and kissed him deeply, “Vincent, you stupid, stupid man! Why didn’t you tell me? I feel the same way, I was afraid of rejection, so I kept it to myself!”

She hugged and kissed him, lifting Sissy off her feet. She looked like the Warrior Princess hugging her whore girlfriend. The thought made me giggle out loud.

I said, “OK, lovebirds, you can kiss later. We still have to win the challenge! It is not going to be easy. Sissy, are you up for some REAL action?”

‘Vincent was ecstatic! Keli loved him! He would have sucked every cock in the world to hear those words. And now they knew about him, too. He didn’t care about that anymore. He was out. He felt like anything was possible with Keli as his girl. This was the best night ever and he had his little sister and her ridiculous dare to thank.’

Sissy said, “Yes, Mistress Samantha! Anything you want, little sister. You name it and I’ll do it!”

He picked me up and gave me a big hug. I hadn’t seen him happier than he was right now. I kissed him back and he put me down.

“Let’s go! It’s almost midnight!” We headed back over to see Master Kevin.

Kevin took one look at Sissy and lost it. He was laughing his ass off and said, “Holy shit, Sam! What did you do to Vincent?”

I said, “Master Kevin, meet my little bitch, Sissy. He is our entry in the Sissy Challenge.”

Sissy said, “Hey big fella, wanna date?” and we all broke out laughing again.

Oh, it was so good to have Vincent and Keli together again, and now they’re lovers, too! I was almost high with excitement.

We were all feeling the love when Master Kevin said, “It’s showtime, kids!”

The place was standing room only around the dance floor where the challenge would take place, the balcony crowded with onlookers.

Master Kevin laid it out; there were three finalists. They would be locked in stocks nude with their top attending. They would use their mouths to pleasure people orally, and their top would administer pain to their rear ends. Men and women could use their mouths, and a paddle hung on a hook at each stock. The winner would be the last to tap out.

I ordered Sissy to get naked. Keli unstrapped the butt plug and pulled it out. We left the cage in place.

“Come, bitch. Keli, help me rig up your new girlfriend please.”

We got the stocks rigged the way we wanted, with the padded waist beam in place and the ankle stocks on to help hold him still. His face was roughly waist high and he was bent over so his ass was fully accessible.

Kelly walked around to the front. She picked up the butt plug and crouched down in front of Sissy giving her another perfect upskirt shot.

Keli smiled at Sissy and said, “Do you like what you see, Sissy? Well, before you get up my skirt you have some work to do.” She rubbed the butt plug all over Sissy’s face and said.

“Open, Sissy.” Sissy complied immediately and Keli slid the faux penis in and out of her mouth. The bitch was moaning like a true slut.

Keli pulled it out and said, “That’s enough. Save it for the real deal. Are you comfortable? You might be in there for an hour or so, can you handle it?”

Sissy said, “Yes, I think so.”

Keli said, “OK, it’s not about giving head anymore, but who can endure the paddle. Think of the sting as extreme pleasure and it will be. I promise you that your ass will feel the full force of Sam’s kiss. Don’t let her size fool you, your little sister has a mean swing. Try to relax and remember the prize.” She opened her legs again. Sissy looked down and Keli closed them. Keli strapped a mouth gag on his face so he could not bite down. She kissed him on the forehead and walked away.

The others had their sissies ready. We chatted a little, comparing notes. The older guy was Ted. His boy, Roger, had a spanking fantasy and Ted was helping him play it out. I recognized him as one of the guys Sissy sucked off in the orgy room.

The other guy was Frankie, there with his partner, John. They had done some paddling at home and they loved it, they were here to satisfy their paddling and exhibitionism fetishes, and both were naked. I was hoping to catch up with them after the challenge.

They were all speechless when I told them my sissy was my brother and this was his first time. We wished each other good luck and returned to our stations.

Master Kevin got everyone in position, with a line forming in front of each sissy. There were a bunch of men, some of them had a big package, so the sissies’ mouths were in for a workout. People were in all stages of undress and chatting excitedly. My station was at the end so I could see the other stations. Being left-handed has its advantages. I picked up the paddle and walked around front to show my brother. A hardwood paddle with holes cut in it, just like the one I had upstairs.

I smiled and said, “Well, bitch, are you ready to win the challenge?”.

Sissy nodded his head and said, “Uhhnn.”

“Good boy.”

Master Kevin yelled, “Two-minute warning!” He checked the sissies mouth gags to make sure they were on correctly. The last thing he needed was someone getting their cock bitten off. They all checked out and he got the challenge started.

The whistle blew and each sissy immediately had a mouthful of cock. There wasn’t much they could do about a steady line of men stepping up to face fuck them. The gags held their mouth open and the cum they didn’t swallow drained out of their mouths to puddle on the floor. The other two tops were older men with younger sissies. I hoped my brother could hold out longer than them. The rule was, if one of us swung the paddle, the others had to follow immediately or tap out.

I stepped up and rubbed Sissy’s ass with my paddle. She groaned at the feeling of the cold wood on her warm ass. I looked at the other tops and they were watching me. I smiled at them and lined the paddle up with his cheeks. I pulled my arm all the way up and swung it down with all my might. It landed square on Sissy’s ass with a loud “Crack!” and everyone could hear him yell around the penis that was fucking his mouth. The crowd cheered. I looked at the other two guys watching me. They had to follow now or lose. Ted swung the paddle down and it kissed Roger’s ass with a loud “Crack!”. Roger yelled too. Another cheer from the crowd. Last to go was Frankie; another loud “Crack!” followed by a scream from John confirmed contact and earned him a cheer, too.

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I looked at Keli who was watching Sissy. She nodded, so I lined up for another swing. My strategy was to pick up the pace and see if the others could keep up. I raised my arm all the way up and swung the paddle down hard, landing the second kiss with another loud, “Crack!”, echoed by Sissy’s scream.

Frankie was right behind me, landing another one on Roger’s ass. Roger screamed and struggled to get out. Ted stopped and released Roger.

Frankie landed another whack on John’s ass followed by John’s scream. The crowd cheered every whack.

I immediately landed another hard whack on Sissy’s ass, eliciting another scream from her. The line of people continued the train on the sissies’ mouths, filling the two remaining sluts with load after load, their hot, sticky cum puddling on the floor below each slut’s chin.

Frankie was up and he raised his arm for another whack. He brought the paddle down hard on Jon’s ass and John screamed and screamed. Frankie tapped out and released John. We were last and had technically won, but I drew my arm back for one more whack to seal the deal. After all, he owed me.

I swung with all my might. “Crack!” went the paddle and Sissy screamed one last time. I hung up the paddle and released her. We held hands and raised our arms in a V. The crowd cheered; we had won the challenge.

We walked over to Keli, Vince’s ass bright red and stinging like a swarm of wasps had stung it. Keli took off the gag, slipped a collar on Sissy’s neck and hooked on a long leash.

Keli said, “Wow, Vincent, I didn’t know you had it in you. Good job!”

I said, “That was unreal, big brother. I am so proud of you! Now, we have to think up something to help take your mind off the stinging.”

Vincent said, “Thank you Mistress Samantha, but my ass hurts like hell! The stinging is intense!”

“Perfect. Keli?” I said.

Keli said, “On your hands and knees, bitch.”

Vincent dropped to the floor and Keli pointed at the puddles of cum on the floor.

She said, “Lick it.”

Vincent crawled over and licked all three puddles of cum off the dirty floor.

I said, “Why don’t we go upstairs and see if we can take your mind off the sting?” I crouched down and kissed him again, tasting the cum of dozens of men in Vincent’s mouth.” Keli said, “Heel, boy.” and led him like a dog upstairs.