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Sissy Training

Sissy sessions with Mistress Nicole after university lectures. 

Every afternoon after university, I slip away from my friends and run with delight to Miss Nicole’s. It was always the same excuse – I was feeling unusually too tired for soccer practice. As I run away from the group, I would feel their questioning gaze burn my back with so much intensity. But their collective heat could never match the one I got everyday from Miss Nicole. She was the only who really made me feel like a woman. I could wear my favourite wigs, trying as many as possible until I found the one that matched my skin colour. Nothing ever beats that feeling. It is the same today as I approach her door. It takes only one knock before she opens it.
The pink lingerie on Miss Nicole’s curvy body is so silky and hugs her tight body so much I can feel my dick already raising its head in appreciation. I cannot wait to wear my own, too. Suddenly, she greets me with a backhand slap that is almost sending me down her steps before she pulls me with force into the house and shuts the door behind her. I am flat on the floor. She walks towards me and stands over my frame.
“Why are you fucking late?” She scowls. She bends over me and grabs my dick, as if wanting to yank it off my body. I moan loudly, more out of pleasure than pain. Her lips which are thick with lipstick part in a satisfying smile.
“The fucking History lecturer won’t end his class in time.” I say, my head already pushed backwards. “You know I love cumming for you. I won’t miss that for the world.” Her lips part again in another satisfying smile. Fuck, I think to myself, her lips are so damn sensuous.
“Nice try, Jake.” She says in a whisper, bringing her mouth to my ear. “But I can’t let you off so easy. I am going to punish you for your offence.”
“Punish me, mistress. I expect nothing less.”
“Good boy. But you know what that means, Jake?”
“Yeah. No safe words.”
“You’re smart. It’ll be pleasing to punish your smart ass.”
She goes into the room and comes back with a familiar whip and red heels. The heels are unfamiliar as I haven’t worn it in any of our sessions before. She throws the pair at where I am lying on the floor.
“Remove your clothes. Only the heels.” I do so quickly. Then, with the move of her whip, she points in the direction of her dining table. “You’re going to be fucking the dining table.”
She comes closer and drags me by my dick towards our stage. She brings a bottle of oil from one of the cabinets and pours the content on the table.
“Let the fucking begin,” she announces with a smirk on her face.
I climb the table, slowly and sensually, trying to please my mistress in the art of seduction. If she’s impressed, she does not show it. Then, I begin to thrust. Slowly, at first, minding the hardness of the table against my dick.
Mistress Nicole circles the table like a tiger roaming its prey. Soon, the first whip kisses my oily skin. “Faster, harder” she commands. I yelp from first thrust, which injects bitter-sweet currents into my brain. I know it is only a matter of time before my dick becomes sore from table-fucking.