Mistress Eliana’s Sissy Academy Ch. 02

Down the stairs and hallway we went as I continued to sob. How could I be so stupid to let this happen? We were a happy normal couple, and all of it is going down the drain because I wanted to get off. I was such an idiot, HOW could I be such a...worthless pig. Maybe Eliana was right, maybe I needed to learn my lesson.

Victor, er...Victoria lead me past the living room where again I saw the men kneeling beside the women. Who were these men, I wondered, future students at this academy? Were all of us going to be in the same program together? As my mind raced, I didn't even realize Victoria stopped in front of a door and I slammed right into her.

"Someone is distracted" she said with a smirk as she opened the door up. "Welcome to your new home for the next year Alyssa!"

I couldn't believe my eyes. The room was entirely hot pink, from the carpet to the walls to the bedding. In terms of furniture there wasn't much in the room: one twin sized bed, a dresser, a lamp on a nightstand, and a desk.

Perhaps the most shocking element of the room was the wall decor. There were posters all over the room of different girly elements, from Hello Kitty to My Little Pony. Hanging above my bed was a poster of a male model from the backside, showing his muscular back and plump ass. I couldn't look away.

Victoria noticed as my eyes were locked on the poster, and she smiled. "You know" she began "the academy isn't really all that bad. Each class is only about an hour a day, and there's plenty of free time around here as well! You'll have plenty of time to socialize and exercise. All the meals are cooked by me, until your kitchen training begins that is!"

I turned to respond: "Oh Victor, how the hell did you let this happen to yourself!? Kitchen training? Maids outfits? For gods sake, your dick is locked in a cage!"

Calmly, she turned and said "It's Victoria" to correct me. "But since you're asking, let's sit".

I sat down on the bed beside Victoria and she scooted close to me.

"I was a dirty cheater. I abused the relationship I had with Mistress Eliana and this is the consequence I have to pay. When I came home one day from work, she drugged me, locked me in chastity and placed this collar on me, the same type that is on you. This is a shock collar, and it allows Mistress Eliana the power to keep me on this property. I tried to escape a few times, but usually it just ended up with me getting caught and punished. After a while, it was just easier to give in. It isn't always perfect, but it is the relationship I have and cherish, and I would do anything to keep Mistress Eliana in my life!"

I placed my head in my hands and began to cry again. "I don't wanna be a girl. I want to go home!"

"Shh baby" Victoria responded and placed her hand on my thigh "we can't have mistress hearing you make all this fuss. I promise it's not all that bad. Pretty soon, you'll learn to love being a girl. I tell you what, before you get locked in your chastity tomorrow, why don't you and I have a little fun to make you feel better!"

I stopped crying and looked at Victoria. "Wha...what do you mean?"

At that moment Victoria leaned in, closed her eyes, and kissed me square on the lips. I immediately stood up and moved to the far side of the room in disbelief!

"What the hell!" I shouted. "Victor, I'm not gay!"

"Victoria" she firmly corrected me again. "Mistress does not allow our male names to be used in her academy. Also, you say you aren't gay, but you file says otherwise" she smirked. "You are the one who pretended to be a woman to get dick pics from a black guy, right?"

My mouth was open but I had no clue what to say! I knew I wasn't gay, but kissing Victoria made my cock twitch. "Listen, I'm sorry but I don't think..."

"Shh baby. It's not gay if I'm a sissy girl, right?" she chimed in.

In that moment, Victoria stood up and began walking towards me. She was already over 6 feet, so with her heels she looked like a giant. She took the straps to her maids dress and slid them to the side, dropping her uniform to the floor. She looked at me and smiled, and then turned as she slowly peeled off her lacy pink thong. I was completely entranced with her every move, her ass looked amazing in that moment. When she turned back around, I had a perfect view of her chastity. It was so tiny, almost smaller than me, and again was bright pink. The lock was in the shape of a heart, and I could see the initials M.E. engraved on it, standing for Mistress Eliana no doubt.

"Like what you see?" she chuckled as she did a sexy spin. I eyed her up and down, and responded "I... I don't know Victoria. If Eliana finds out she could..."

In that moment, she pinned me up against the wall, and moved in to kiss me again. This time, however, I reciprocated. We started passionately kissing, rubbing our hands over each others bodies. I couldn't remember the last time I felt this good, and my cock began to grow. In the moment, I grabbed Victoria's ass and she gasped. "What a dirty boy" she said as her long pink nails reached down to my belt. "Or should I say, dirty girl".

Within a matter of seconds, my pants hit the floor, followed by my underwear. My dick was at full mast, and she saw it she started to chuckle. "My my, it is small isn't it!"

A wave of humiliation washed over me, my face turned blood red. "It's okay baby" she responded "it's the perfect size for a sissy like me!"

In that moment she dropped to her knees and swallowed my cock in her mouth. I haven't had a blowjob in months, and her warm mouth felt incredible as she bobbed her head up and down. The man I once knew as Victor, a successful handsome man with a prize of a girlfriend, was now on his knees sucking me off.

And I was loving every minute of it.

After a few minutes I felt like I was ready to explode, but she stopped. Victoria rose to her feet, took my hand and said "baby, I want you to fuck me, okay?"

I couldn't believe my ears! I had never had any form of anal sex before, and I certainly didn't imagine my first time being with another man!

Before I could even respond, Victoria pulled me down onto the bed and began kissing me again. Her tongue ran up and down my neck, and then back to my lips. I was mesmerized in the moment and thought, what the hell, this might be the last time I get off for months.

She rolled over to all fours and I stood up behind her. With one deep breath, I slowly slid my cock into her ass.

We started going slow at first, but began increasing the pace with every thrust. "Ooo yes baby" she purred "stick every bit of that tiny cock in my pussy! I want you to fill me up!"

In that moment I looked up again and saw the naked man on the poster. His ass was so firm, I could only imagine what tasting it would be like. I imagined what it would be like to fuck him like I was fucking the sissy maid in front of me. I looked back down at Victoria, her ass was so tight and looked so good, I knew I was going to cum.

I continued to thrust inside of her, over and over again until I couldn't hold it in much longer. She screamed "FILL ME UP LIKE THE SISSY BITCH YOU ARE!" And in that moment, I shot my load inside of her and screamed in pure bliss, the best orgasm I had ever had.

I sunk to the floor and Victoria stood up, and kissed me again. "Mmm baby, you're going to fit right in here" she said with a smirk. She slipped her dress back, and stuck her panties in my mouth before moving to the door. "Get some sleep, you have a busy first day tomorrow!"

To be continued...