Sissy Forced Anal Story

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Mistress supervises my first cock suck.
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I am bound spread-eagle to my bed. A hard cock is about to cum in my mouth.
Mistress is teasing my cock thru my panties, keeping me very hard, and fully engaged. The sexual intensity is palpable. My fantasies have been usurped by reality.
"It's happening!" There's no time to think; He's cuming in my mouth! He's pumping in and out, and I'm swallowing, tasting his cum, and swallowing again.
I hear him groaning; I hear Mistress squealing with joy, and I have completed my first suck job. I am officially a sissy cock sucker.
How it began: On our first date, we shared our kinky fantasies. Actually, I shared mine, and we never really got to hers'.
Our next date found me tied to the bed, she straddle-fucked me, and my search was over. I had found the woman of my dreams. We were together every night, and 99% I was bound and straddle-fucked.
We evolved; mostly my fantasies. Number one, Crossdressing and feminization. Number two, Forced cum licking. Number three, Edging; my orgasm came when she allowed it. Number four, Being trained for the above by Mistress.
It made me shutter with sexual excitement; I had a Mistress who would "train" me.
Crossdressing: The first few times I put on her panties, I became so excited, we simply dove into bed and fucked hard and fast and I blew my load in seconds. After a few times, she bound my arms, then teased me with her panties.
It was indescribably sexy. She teased, holding a pair of pink thongs before me, "How about these? Would you like to wear these cute little panties?"
"Oh, yes Mistress," I pant, and she slips them up my legs. I raise my ass I she nestles the panty between my cheeks; I feel the material teasing my rear hole, and then she maneuvers the panty around my hard cock, taking note of the size and type panty that best contains my cock and balls. Then she binds my ankles.
"There we go," she whispers. "Don't you look cute in your little pink panties. Would you like to wear these panties all the time?"
"Oh, yes Mistress," I pant, while she strokes a fingernail up and down my cock, which is leaking pre-cum, creating a wet spot.
Next she squeezes out my precum, onto her finger, and into my mouth. I accept it with no pretense. My training is well underway.
She slides the panties to the side, straddles me, and slips my cock head into her pussy. She loves this part, when my cock head first enters her, she savors it for as long as possible, and then slowly lowers, and her pussy envelopes my cock.
She looks into my eyes. We are connected ethereally. This moment cannot be improved upon.
Then she begins to move. I always need to cum before she is ready. It is understood that I'll tell her, "You're about to make me cum!"
She stops, mounts my face, and I lick her pussy. She whispers as I lick, "That's a good slave. Lick your Mistress." She turns around and I'm licking her ass. "Deeper, work that tongue deeper. That's a good sissy." She's looking down at me, "Your panties are so cute. Good sissy."
Then she remounts my cock. This process is repeated until she decides I can cum. Again, I say, "Mistress, you're going to make me cum." And she does not mount my face. She continues to rock her hips, and I hear myself say, "Make me lick you clean."
Before I cum, I want her to do it, but as soon as I cum, I want it over. The last thing I want is to lick my cum from her pussy.
Then it happens, I blow my cum deep in her beautiful pussy.
For many sessions, she did not make me lick her clean. The sex was over, and we simply went to sleep. But then I gave her the clue as to how she could enforce it. I said, "Keep me tied up. Don't untie me until I've licked you clean."
That did it. She fucked me, grinding her hips until every drop was milked from my cock. Then she was still for a moment. I knew what was coming, and as usual, I did not want to lick my cum, and my cock quickly shrunk to a nub.
And she was upon my face. "Lick!" Her authoritative command asserted her as Mistress.
I licked, submissively acquiescing to her. I loved it. For the first time, I was forced to do something I didn't want to do. It changed our dynamic, and we delved deeper. She became more Dominant, and me more submissive.
I started shaving my legs. She actually gave me the choice, rather that force me. I'd already shaved everything else, and I loved my hairless body, but now I was announcing it to the world. That was my crossing the Rubicon, and no one seemed to notice, or care. Being shaved felt so feminine!
Now, before I was bound to the bed, I dressed in sissy attire. Often, just a bra and panties, which made me rock hard. The idea of ravishing her on the spot was ancient history. I put on whatever sissy clothes she selected, then laid back as she looped my hands and feet, and I was bound to the bed, in sissy slave heaven.
We had acquired sex toys, and almost always, an 1-1/2" plug was worked into my ass. All the while, she teased, "We need to get you stretched, in case I decide to bring a man in here to fuck you. You'd like that wouldn't you? A nice big cock?" Then the gusset of the panties was placed over the plug, and she teased, "This will keep the plug in place. Not that you need it," she smiled.
The plug was a love/hate, but the love quickly dispelled the hate. My sphincter defied my mind, and acquiesced to the plug, and in just moments, I was obscenely moving my hips around. My rear hole, now had a second purpose, it was now my pussy, my sissy pussy. That's what Mistress called it, my pussy. I was trained to always refer it it as my pussy.
Among our toys were dildos, and now I had a plug in my ass, and she fed me a dildo while she fucked me. There was no pretense, she was training me to suck cocks. "That's a good girl. A little deeper. You're such a good cock sucker."
Never had I told her I wanted to suck cocks, but she read deeper into my mind than I could myself. Somewhere inside, it was a natural part of our progression. She teased, "Evie wants to fuck you. I have told him everything, and I'm going to bring him in here one night, and watch him fuck your mouth."
Everett was her gay friend from work. She called him Evie. I'd met him once or twice at her office parties. She told me he thought I was good looking.
Now I wore a bra and panties during sex. Once while she was fucking me, she teased my nipples thru my A cup bra and said, "I want you to sleep in your bra and panties."
"Yes Mistress," I replied. I liked the idea, until of course, after I came, then I did not want to sleep in my bra and panties. Nonetheless, her threat loomed; I remain tied up until I surrender. There was no resistance. From that point, my sissy attire became a bigger player in my sissification.
I wore dainty pink nighties to sleep, and it was understood that in the morning, I remain in my nighty. Mistress walked around the house in frumpy sweats if she wanted, but I was to remain in my sissy nighty.
In the mornings, I continued to refer to her as Mistress. I was not bound to the bed, but I had surrendered to her. Sometimes she'd snap a finger and point, and I'd drop to my knees before her.
One such morning she announced, "I'm inviting Evie here one night soon. You're going to suck him, and if he wants, he's going to fuck you."
It happened that night. Mistress was dressed in thong panties, and a tight, sheer camisole, and I was attired in the same. After I was bound to the bed, she added a new twist, and put makeup on my face. My cock was rock hard in my panties.
Then she sent a text. Moments later, she went to the door, and she and Evie walked into the bedroom. He smiled, "Oh my, doesn't she look enticing!"
He removed his clothes. His body was also shaved, and I was entranced! Most men have hairy, ugly bodies, but not Evie. He was thin and taut. His cock began to harden as he climbed onto the bed.
Mistress gave him her phone. She wanted Evie to video the event. "Smile," he said, as he turned on the video, and his cock approached my mouth.
Mistress lay beside me, stroking my penis, keeping me excited, but not enough to come. She encouraged, "Oh, my little sissy! You look so darling with a cock in your mouth!"
Evie's cock had grown to full size, and he was kind enough to not force it too deep, lest I gag. He handed the phone to Mistress, and began to pump in earnest. I knew it would not be long, and then he groaned, and the first jet of cum filled my mouth.
I swallowed instantaneously. Then the next jets filled my mouth. Swallowing was not so immanent, and I tasted another man's cum for the first time. I continued to work my tongue on his cock, until it began to soften, swallowing all the while.
The Mistress straddled, and pulled my panties aside. She mounted my cock, and Evie laid beside me, and watched her fuck me. Soon I was licking my cum from her pussy, thanking her for the umpteenth time for training me as her sissy slave.
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To prior Anonymous poster: Go look up what a 'No True Scotsman Fallacy" is.
Just because YOU may have a particular idea of what constitutes a 'Sissy' doesn't somehow make your opinion a universal axiom or inviolable truth; get off your arrogant high horse and understand that others may have thoughts, ideas and opinions that, while different from your own, are no less valid.
Quote "Most men have hairy, ugly bodies" ......... Just what kind of sissy are you FFS. A SISSY is a piece of meat that is used by real men. Fat ugly old men usually, the sissy doesn't get a fucking choice. A SISSY doesn't get turned on sucking the "clit" of another sissy. What is the fucking point in that! Shows how little you know about being a sissy.
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