Welcome to my Halloween Blog Train Story, if you have not read the story before mine from Mistress Mandy, you can find it here: 

Enjoy my Halloween Blog Train Story!  You can choose to read it or listen to the audio version below.  (The audio is great, take a listen!)

 

 

The Beginning….

As all great halloween stories start, we begin on a dark, cold night, the evening of Hallow’s Eve. They call this the night when the veil between living and dead is almost non existent. For adults this night allows you to be anything you dream of being, from superhero to super sexy, your imagination is set free this night of all nights.

It was on this night that Harold Fishbottom had decided he would be his authentic self and sissy himself up, and wander into the real world, leaving his sanctuary…home.

Harold had been dressing up for years and had a collection of lingerie and women’s clothing that would rival any closet of a female out there. The first time he had put on heels, he knew he was home. He has purchased his collection over time, piece by piece, he had learned the art of make-up from watching countless hours of tutorials on youtube and had sauntered around his own house for years showing off, for no one.

Tonight, he was venturing out to a costume party at a local club that had been around for a very long time. He was going solo, but was comfortable with this, not wanting to have to answer to anyone tonight and to “show off” as he pleased.

The outfit had been chosen carefully. The theme? Sexy vamp of course, how could it not be. Black panties and matching lace bra with silky thigh highs and black garter belt.. A black dress purchased at a second hand store had a boho meets goth feel to it. The fabric was a mix of velvet and lace, giving it a dark, rich texture. The bodice was fitted with a deep neckline trimmed with intricate lace giving it a somewhat sensual and mysterious vibe. Long sleeves made of sheer lace that came down to a point over the top of each hand. The waist cinched with a corset like structure while the skirt flowed freely in layers with boho inspired ruffles and fringe at the edges. The hemline uneven and swayed with every step. It was a one of a kind and Harold knew it the minute he laid eyes on it in the store.

Bright red nails and toes nails matched his red lipstick which was aptly called, “Siren Red.” Harold took his time on his make-up this night, creating, what he hoped was an erotic dramatic look. Cat eyes, long false lashes and shadowed cheekbones trying to create the perfect sexy vampire. He wasn’t into total cliches so opted for a blond wig as opposed to a black one. When he stepped in front of the mirror he saw…..Harold the sissy. But deep down he wanted to see, Betina The Beautiful, a real girl. He was not passable, but his look was stunning.

He picked up a small black handbag with essentials, grabbed his keys and headed for downtown and to the club party.

 

Welcome to The Party…

As he stepped out of the car, he was excited, there would be no hiding tonight. This was the night to show off in all his glory and while most would be wearing costumes, Harold would be his authentic sissy self.

Making his way into the club there were people wall to wall, the dance floor was filled with costumed bodies moving in an erotic frenzy. The four bars in the club had more costumed bodies sitting on stools and dancing in place with drinks in hand. For a mere moment, he felt nervous, he didn’t know what to do next. He was “here,” but now what?

The music was loud and heavy on the base, he felt it right to his core. He was trying to decide what to do next when he felt a strange sensation.

Meeting The Mysterious Green Eyes

It was at that moment he felt his eyes drawn to a figure on the second floor of the club, looking down at him with piercing green eyes. When he looked up he was greeted by a vision of red curls tumbling over her shoulders and down her back. But what made her look so unusual….she was not wearing a costume. A simple red dress that hugged her curves. Hey it takes the right kind of redhead to pull off wearing a red dress and she was doing just that, pulling it off. She gave him a little wave. He waved back.

He didn’t know why but he headed toward the stairs, took his sissy self up and walked towards her. She showed no sign of surprise and that surprised him. “Hello sweet girl” she said in sultry tones. “What is name?” His mouth answered while his brain felt frozen in time. “Betina, my name is Betina.”

“Well Betina, you may call me Domna. Now, you look like someone that is in need of a little adventure, a little excitement on this fateful night, no?”

He nodded his blonde head, unable to speak but wanting to ask a million questions.

“It just so happens, I have my own office of sorts here at Chez La Rage, what do you say we go have a little talk, eh? Far too noisy for most ears here”. She laughed, a laugh that sounded magical, dangerous, and alluring all at the same time. He wished he had a joke at hand, just to hear her laugh again  but his mind was empty.

He followed her heart shaped ass in that tight red dress through the crowd and through a door that went down a long hallway. At the end of the hall was another door. The door looked like it didn’t belong here. It was old, thick and had old fashioned locks, ten of them. Clearly only the very special were allowed to open the door. And the mysterious woman was very special, which dear Betina was about to discover.

Behind the Door

She opened all ten locks with ease, in front of them a dark steep staircase. “Hold tight to the railing on your way down sweet Betina.” She cooed. He followed her without question, not knowing why, he just did. An array of scents filled the nostrils. Damp musty scents from the cold stone walls and a bit of metallic tang from rusted chains with just a touch of mildew. It smelled stale, mysterious and it left him wondering if following her had been the right choice.

Torches on walls were only the illumination. He felt as if he had traveled to a different time, and in many ways he had. A stone bench that looked ancient was at the far end of the room and behind it chains were attached to the stone wall. The atmosphere echoed of past souls who had been at this very spot. They were alone, yet Betina did not feel so alone.

“How is this an office”. Betina blurted out. ”

Well I did say office of sorts.” Domna laughed.

“Why am I here?”

“Well sweet Betina, this is your lucky night. It will be life changing if you want it to be. You see, I know you are not really wearing a costume tonight, you are being who you would love to really be. Feminine, girly…you wish you could dress like this every night…don’t you?

“Yes,” Betina blurted out.

What if I could change your life and you could do so 365 days of the year, would you want that?

“How? What would I have to do? I don’t understand.”

“This is the Dungeon of Nueva Vida, it means new life. It’s been here for centuries, secretly, changing lives of a select few. You don’t just want to be a woman, you want to be a whore. So tonight, you must prove your whoredom. “Do that and I will make your dream come true.”

“What are you?” Betina stuttered.

“Well, I am an ancient Vampire who has many gifts. Not only can I give you eternal life, I can give you the life you want IF you pass the test.”

“Are you ready?” she asked

Betina shaking, nodded her blonde head yes.

The Test Chambers

“Through that door you will face several challenges. Do your best, reach down and find your inner whore. I shall be here waiting at the end.”

Betina took his first step through the door, he felt surrounded by wind, but there were. hands taking off his clothes. He could not see until he was standing naked but with his thigh highs, heels and wig still in place. He felt cold but excited. A dark figure approached him. It was a male in a long black cloak, he could not see his face. The man walked toward him with purpose and without saying a word put two nipple clamps on his very sensitive nipples. BUT, each one had a chain with a weights attached. They hurt, the pain of it shocked him. It literally felt as if his little nips would break off his body. He let out a little cry and the man pushed him to keep walking through the chamber.

As he continued the weights swung with every step, and with ever step pain. He came to yet another door, opened it and inside he heard moans and groans, it was filled with men, also naked and everywhere he looked he saw hard long shafts. He felt hands on his shoulders and was pushed down to his stockinged knees. The man didn’t speak but pushed himself inside Betina’s lips and he knew what to do. This test he would have no problem passing….or so she thought.

Sissy Debauchery at The Dungeon of Nueva Vida : Sucking Cock

He let himself live in the moment pleasing him to completion. Not even a gag out of him and he was proud of that and ready to stand…only the room had other plans. Once he pulled out of his sweet lips, another male took his place and it began again. Surprised but ready to perform again, he used his mouth to please him too until he felt his hot white serum all over her face.  Betina was still sputtering when the next one pushed into his lips. How many would he have to please??

 

He stopped counting after 27, not caring and just trying to achieve his goal, How long had he been there? It felt like hours, his jaw was exhausted, his mouth numb. All of a sudden after spurting, the male satisfied, grabbed him by the shoulders and stood him up on his high heeled feet. Without saying a word, he pushed Betina out the door and off to the next chamber.

The Bed Chamber

 

As he  entered the next room he saw a 4 poster bed, it was beautiful with lace covered pillows and an antique looking bed spread. There was something very romantic about the room and for a moment he felt relaxed. But it was only for a moment. Betina heard a male voice in deep tones tell him to get onto the bed on all 4’s. In this position, the nipple weights shifted to  a new angle of pull on his poor nipples, causing  new pain.

He assumed the position and waited for what felt like an eternity, then felt the weight of the bed shift as a man situated himself between his legs. He felt his hand spread a thick lube between his ass cheeks every so matter of factly before he grabbed his hips and pushed himself inside in one long stroke.

He let out a gasp of surprise expecting his entry to be slow and sensual but it was anything but. He felt the guy’s ball sack hitting the back of his ass as he plunged in over and over again. When he finished, he smacked that ass and was off the bed. Betina knew before it happened that another would take his place. And he did. Male after male took their turn without a word. Again he stopped counting at 27 and had no idea how long she had been on that bed looking at the wall.

He only knew it was over when he didn’t feel the weight of another body onto the bed. Betina collapsed on the bed hoping for a moment’s respite but none was to be had.  He  felt strong arms pulling him off the bed and pushing him out the door.

 

The Reward for The Sissy at The Dungeon of Nueva Vida

Betina found himself back where he had started, and miraculously  back in full vampire dress standing in front of Domna. She had a mischievous smile on her face.

“So, I chose well tonight. Are you ready sweet Betina to become a real woman that will live forever, men had your beck and call. Now, I will give you one last chance to run away and live your current life, OR, run into the shadows with me and be forever changed.”

Betina smiled, walked toward Domna, pushed her hair back, and presented her neck to Domna and waited for the pain that would be fleeting and that would change life forever.

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Dearest Sexy Readers, I hope you enjoyed my story and that it will make it in your top 5 votes.

Next up on the Halloween Blog train is Miss Daphne’s story. You will find it here Tomorrow