My Professor's Sissy

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After dinner, I was led upstairs, legs shaking in my heels. Stripped out of my dress, knowing smiles around me, I couldn't help but softly whimper, brimming with excitement. My tights were replaced with pink stockings, held by a matching garter. A tightened corset around my waist was the only other clothing I was given, led to the bed by Professor Amber. On my hands and knees, facing Felicia sitting in front of me, I stared with wide eyes as she giggled, playing with my face.

"Are you excited, sweetie?" I nodded, tiny noises escaping my lips, a physical manifestation of the eagerness I felt. She smiled, cupping my chin as she stared into my eyes, drinking in the moment. I moaned as I felt the bed shift behind me, Professor Amber's hands running over my exposed ass, playfully spanking my clit.

"Are you ready, indeed. Two months of being our good girl, trapped in this cute pink cage for us. Such a lovely sight." I blushed hard from her words, pinned between both women, unable to speak. Her spanks turned to rubbing, feeling the straining in my clit, the desire to escape, to be free, to cum.

"I do feel bad, however, in misleading you." Professor Amber continued, removing my plug carefully, adding more lube. I moaned, my mind not working well from being rubbed and toyed with, confused by her words.Misled? I didn't have to wait long for my answer.

Feeling a cock rubbing up and down on my ass, teasing my now exposed hole, my moan turned into a gasp. Felicia giggled, staring at her wife as she held me, hands running through my hair. "Yes, my beautiful sissy. My good girl. I promised at the end of the semester, being the ideal student and toy for me, that you would cum." Emphasising her point, she slid the cock strapped to her all the way inside of me, my eyes rolling back in my head. "But I didn't tell you how..."

I couldn't speak, couldn't think. The cock evenly pushing inside of me, stretching and rubbing in the most wonderful ways, had robbed me of my mind. I didn't protest not being unlocked, didn't whine at being deceived. I simply held my position, ass pushed out behind me, back arched, staring at Felicia while I was fucked. This was heaven. This is exactly what I had wanted. What I needed.

My moans filled the room, unable to contain them as Professor's Amber cock owned me. "Oh Syl," Felicia smiled, staring past me, "she is so cute! You have to see the expression on her face!"

Her wife smiled, "Well after I am through with her you can take a turn and show me." My body quivered at that, Professor Amber's thrusts picking up speed. "I am having far too much fun right now to swap."

I knew I was close to cumming, that familiar confusing feeling inside of me. Anal orgasms were similar but oh so different to 'regular' ones, seeming to ride the edge of cumming infinitely. The build up seemed to always be there, always ready to release, and yet seeming impossibly far away. Until it wasn't. Until you realised what it truly felt like, where that line truly was. Until the feeling coursed through every part of your body, clit tingling, your entire body threatening to explode.

I whimpered excitedly, barely able to voice my desperate plea. For months I had restrained myself asking permission to cum. Each time I felt as if I couldn't hold out any longer, I remembered the excitement in Professor Amber, the way her eyes sparkled keeping me on edge. Each long frustrating night, straining moment in my cage, teasing session where I felt I couldn't hold out any longer, that joy pushed me through. But none of it compared to her cock, vigorously thrusting in and out of me, the feeling I had been missing all these long months. The need.

Smiling behind me, sweat glistening on her forehead, hands on either side of my waist, Professor Amber picked up speed hearing I was close, hearing my tiny plea of desperation. She nodded to Felicia, who smiled, leaning in to whisper in my ear.

"Come for us sweetie, come for us my good girl." I squealed hearing those words, those beautiful intoxicating words.

And I came.

Oh my fuck did I cum. My entire body tensed, quivering as I released, months of denial exploding out of me. I felt my caged clitty leaking and spurting cum, leaning into Felicia for any support she could give. Professor Amber's cock never slowed, fucking me hard through my orgasm, those eyes dancing with excitement as she saw me shiver and squirm. My ass pulsed around her cock, desperately wanting more as I felt waves course through me, each time pushing cum out of my clit.

Remembering to breathe, nearly in tears, I gasped, head collapsing into Felicia's lap. Her trademark giggle comforted me, hand still brushing back my hair, softly calling me a good girl. Professor Amber, also out of breath, pushed deep inside of me, gently patting my ass, seeing I was spent. I stayed in that position for a long time, quietly whining as I felt her cock pull out of me. When I regained myself, they both cuddled in each others arms giggling, watching as I cleaned up my orgasm with my tongue, licking the bed clean as best I could.

I came three more times that night. None quite as powerful as the first one, but by the end of the evening I had been drained of cum, most of which was fed right back into me. Both Professor Amber and Felicia took turns making me moan, noticing that Felicia had her own cock as well, which was exactly the same. Her wife simply rolled her eyes, still not sure why they couldn't just share (because I want my own!). I giggled through it all, floating euphorically between them.

Cleaned and showered, they slipped me into a pink onesie for bed. Snuggled into the guest room, I mumbled thank you over and over to my keyholder, how happy I was. Professor Amber simply smiled, gently brushing my hair with her fingers. "I know, sweetie. I know."

The next morning I sat at the table, feeling awkward as Felicia served breakfast. After all, that had been my job for the last two months. I looked across the table at Professor Amber, that familiar mischievous look in her eyes as she stared at me, a blush coming across my face.

"So," she said, leaning on the table, "What are your plans for next semester?"

I couldn't help but smile.

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8 Comments
pristina47pristina477 months ago

This is so excellent. Maybe my favorite story on the site

Royse69Royse6911 months ago

loved the story, I hope more to cum

RoryRougeRoryRougeover 1 year agoAuthor

Rory is the feminine name I go by, and sort of defaulted as a pen name as well :P. But certainly I constantly ride the ebb and flow of being masculine and feminine, as well as submissive and dominant. A lot of my writing is an escapism of sorts at the moment, so it is often catered to my more feminine desires. But from time to time my other half tends to slip in :P. Glad you liked it!

AnonymousAnonymousover 1 year ago

Lovely story! Well-written, very hot and with a relatable main character. Especially this passage perfeccaptures how one can feel at times:

"A part of me wanted to be under her desk, worshipping those legs, spending days doing whatever she willed. A part of me simply wanted to be her, feeling so confident in those clothes, teaching about a topic I knew like the back of my hand. And a small part of me, the more dominant masculine part, wanted to bend her over that desk in the middle of a lecture, fucking all the frustration I had accrued at her hands back into her"

I was slightly surprised by the name Rory, for me that is rather masc., but it seems a name that means a lot to you so I can understand why you use it

AnonymousAnonymousalmost 2 years ago

Amazing. i came twice reading it! and a few more times the next day... more please.

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