Samantha and the Dare

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.