tagTransgender & CrossdressersA Tale of Two Sissies Pt. 01

A Tale of Two Sissies Pt. 01


She had forced me to open the door dressed as I was, and now I stood before my boss, head bowed in shame...The shock on his face echoed that which had frozen me to the spot. "Well don't just stand there, ask the nice man in!" barked Mistress Andromeda, and I nearly died. I did as my mistress had instructed, and invited a now bemused Mr. Craven inside. "What a stroke of luck, just what you needed, eh Stephanie? A real man to play with... aren't you going to introduce us?" said Andromeda. As she approached, I heard muffled groans from the room beyond, my wife unable to express her panic due to the gag she wore.

I had wanted for some time to dress as a girl, and had worn items of female apparel from time to time...I found women fascinating, and adored the way they looked and the way their clothes felt on. My wife tolerated this in me, and had intimated that she enjoyed being spanked and dominated, so we had contacted Mistress Andromeda to expand our horizons. We had dressed as agreed, my wife and I both in school-girl attire, and my wife helped me apply make-up and a wig. I was amazed how girly I looked. Andromeda arrived and took control. My wife was trussed up and gagged, and I had been instructed to watch whilst she was taken from behind with a strap-on dildo.

I introduced Mistress Andromeda to my boss, Ian, and she shook his hand firmly, I must have looked quite a sight in my girly shoes, knee high socks, school skirt and blouse. Andromeda still wore her strap-on, and Ian smiled as he gazed down at this..."Stephanie here was next up for this, Ian, but now you're here, maybe she can try the real thing?" Andromeda reached down and placed her hand on his member, and, feeling it palpably stiffen, smiled. He laughed, and she began to unfasten his trousers and turned to me, pushing me to my knees. "Perhaps you should show Ian how much you appreciate him dropping by."

I knelt before my boss, as instructed by Andromeda. "I think it's time to have what you've always desired, a real man's essence in your mouth, Stephanie. You have chosen this path because, deep down, you want a real man inside you." I fumbled with his belt, my own member already hard from her words, and lowered his trousers. His boxers tented outwards towards me, and as I pulled them downwards, his member sprang upwards filling my field of vision. I opened my mouth and leaned forward, engulfing the end of his penis. As I savoured the taste and throbbing warmth, he placed his hands on the back of my head and began to moan as he began to push gently further into my mouth.

Mistress Andromeda laughed..."I can see I'm not needed here..." she said as I started to gag on my boss's member. "I think your wife needs some more attention now." and with that, walked out of the hallway and back into the adjoining room. My wife was where Andromeda had left her waiting, tethered to the dining table. Andromeda positioned herself behind Karen, and entered her, resuming her assault from the rear...I could hear her moans of pleasure, somewhat stifled by the gag, as Andromeda informed her that she had a surprise in store. My wife's struggles intensified as she approached orgasm, and I could hear the table scraping across the floor, accompanied by muffled shrieks as Mistress Andromeda assaulted her from the rear. Stealing a sideways glance, I was shocked to see that the kitchen table had been moved, affording my wife a good view of me as I sucked Ian's meat. Karen stared with wide eyes, transfixed, her expression difficult to read with her gag in situ.

I returned to the task at hand, noting that Ian's pace and breathing were picking up. "Stroke my balls, 'Stephanie', I'm going to fill your mouth, you dirty girl" he gasped. Ian continued to thrust his member halfway down my throat as he held the back of my head, and as he reached his crescendo, withdrew a little. "I'm coming, girl, and you'll take it all, if you know what's good for you." With that, he erupted within my mouth...I felt spurt upon spurt of his juice trace paths across my tongue as cum backed up in my throat. As he withdrew, I hesitated, unsure as to whether I could swallow this bitter-sweet slime, another man's cum? I had crossed a line, willingly, yet doubts assailed me. I raised my eyes to meet his gaze.

"Swallow it, Stephanie." he said, slowly and deliberately, his eyes and tone said it all...I would submit to his will, abdicating responsibility for my actions.

Fear, guilt and inhibition abandoned me and I obeyed, swallowing a portion. "I'll have to get used to the taste." I thought, toying with the gooey mess in my mouth. I licked my lips.

"All of it!" he barked, and swung his erect prick around in an arc, catching my cheek with a wet slap. Ian began wiping it over my face, spreading slick trails across my cheeks. I swallowed, relishing the act. "Now lick me clean." he instructed. I took him again into my mouth and ran my tongue over his meat, eager to please. I had wasted many years waiting, buried feelings for so long, and now I was free! Never had I felt so aroused: reaching down, I caressed myself through wet knickers as I licked him clean.

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