tagTranssexuals & CrossdressersHow I Became Sissy Willow Ch. 02

How I Became Sissy Willow Ch. 02


"Now the preliminaries are over, and it's time for the entertainment part of our evening!"

That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation.

Fern had found a magazine I'd left on the bedroom floor, showing a transvestite being tortured and humiliated by a couple. Although she had always known I liked to crossdress, she had never paid any attention to that side of me. Now she had had me dress up, and her lover of the last year had fucked my face and ass.

Now, I was not sure what she meant by "entertainment, " and it scared me. My fears turned out to be justified. Fern picked up my magazine she'd found earlier ("Sissy in Peril" was its title). It showed a transvestite being humiliated and tortured by a couple, and Fern had used it as a springboard from which to begin my own humiliation, and my forced acceptance of Jason as her (and my) lover.

"Did you know that there is no video of this magazine?" Fern asked. "That seems a shame! I think we should remedy that! What do you think?"

I hesitated with my reply, and was rewarded with a slap across my face by Fern. She then pulled me off the bed and I lay on the floor on my back. "Your only response to my questions is to be yes. Is that clear?"

"Yes, Mistress," I replied.

"Oh, there is no need to call me Mistress. Just call me Fern. I think that way your humiliation will be clearer. Not by a truly dominant woman will you be put down, but by the woman to whom you were once betrothed, married, and equal. You have fallen, willow, dear, and I don't think you can get up again!"

Fern ordered me up onto my knees and I obeyed. Jason got up from the bed, where he had been laying on his side watching Fern and me with an amused grin on his face. He reached into a gym bag I had not noticed before. He brought out a set of cloth﷓lined cuffs, about two inches wide, and connected by a chain. He cuffed my ankles together. I instinctively placed my hands behind me, waiting for their bonds. But Fern ordered me to place my hands down at my side.

Fern then picked up the "Sissy in Peril" magazine, and opened it to a page she'd marked with a post﷓it note. "Ah, yes. I see that the woman gets her ass licked by her sissy slave. I think

that should be the next act in our video."

I hadn't forgotten the earlier scenes Fern had captured on our video camera, and I wasn=t certain I was ready for the next scenes.

Fern bent over a chair, and lifted her beautiful ass up. Jason placed his hands under my arms and pulled me up till my face met Ferns ass. He then returned to activate the video camera pointed at my face.

"Lick it, sissy willow," she ordered. Of course, I did as I was commanded. Licking Fern's ass was one of my favorite activities, one I never got enough of. I put my tongue deep into her ass, and wiggled it in there for a half minute. Then I slowly drew it back, and lapped around her hole. Up and down her crack I went, over and over. Then I licked circles around her hole, clockwise and back again. As she thrust her ass back I began to put my tongue into her hole, in and out, deeper and deeper.

After 15 minutes or so Fern tightened up her thigh muscles and closed her butt cheeks. She screamed with an orgasm.

She turned around, so she was facing forward in the chair. Instinctively I placed my face into her pussy hair, hoping to bring her to another orgasm.

Instead of gaining access, I was pushed away. Fern pushed so hard I was on my back with my cuffed legs bent back under me. Before I could move I felt Fern's foot on my balls. Through my panties her foot threatened to crush my privates.

"Cunt!" she cried, leaning forward and increasing the pressure on my balls. "I did not tell you to lick my pussy. For that you will be punished!"

Fern snapped her fingers, and Jason lifted me to my knees and brought my hands behind my back and cuffed them there. I now knelt on my knees. My ankles were cuffed together, and my hands were cuffed behind me. Then Fern put her hand behind my head and pushed me down,

so my forehead touched the carpet while my ass pointed up.

"In your magazine the sissy gets spanked by a hairbrush over his mistress's knee. I will not place you over my knee. God knows what your little penis would do in contact with my beautiful thighs. But we will apply the hairbrush my sissy willow."

With my head still down I waited in anticipation of the first swat from my wife. When it came it was so hard I instinctively lifted my head up.

"Oh, no, dear willow" my wife said. "You will not lift up during your training. Will you please hold her down, Jason?"

Jason came over and placed his hand on my neck. Roughly, with no affection, he pushed my face down to the floor. He leaned down and whispered : AThis turns me on, dear willow. Take this training, and I might give you more of what you need."

Fern began smacking me with the hair brush. Aided by Jason's grip on my neck and his promise of rewards to come, I accepted 50 strokes with the back of the brush (I counted to myself) with only minor screams, though I was sobbing uncontrollably by the time Fern finished.

To my surprise B and horror B Fern laughed when she was done. "That was not only for your unauthorized lunge at my pussy, dear willow. That was also generally for being a sissy. I love you, dear, but I hate the sissy in you. Yet the sissy is so much a part of you that it will only be that side of you I will see from now on. If it was only hate I felt, you would be my ex﷓husband, exposed to his family and friends as a sissy. But because I love you, I am willing to use these punishments to exorcize the hate I feel and find a new venue for us to express our love."

I opened my mouth to respond to this curious contradiction, but hesitated because I did not know what to say. Fern simply laughed. She uncuffed my hands and ankles, and pushed me back so I lay flat on the floor. She picked up my magazine, and opened to another page she'd marked with a note. She bent over me, showing me the page she's picked, she laughed and said "I had trouble finding these pages, willow. They were stuck together by your cum!"

The pages showed the transvestite with her cuffed hands behind her, attached to a door knob. But the part of the picture which made me cum so often was that her nipples had clips attached to them, with the clips tied to a chair in front of her. In a succession of pictures the woman in the magazine moved the chair back, stretching the nipples of the poor transvestite.

I opened my mouth again, but this time Fern simply slapped my face. I started to cry with the pain. Fern grabbed my chin and lifted it up. "Yes, my dear, cry now. Soon you will find a reason to cry, but with nobody to hear you."

She looked at Jason and turned her palm upward. Jason seized me, and turned me over on my back. Fern lifted my legs, then brought my hands behind my thighs and recuffed them. I was on my back, with my knees up and my hands cuffed behind them.

Fern then went to Jason. Kissing him, stroking him, rubbing her cunt against his thighs. I looked stunned, I guess. Fern looked at me and laughed. "Poor willow. Are you jealous that I am getting Jason hard?" And hard he was. That huge cock was sticking straight out. Fern reached over and stroked the cock, then Jason started rubbing Fern=s body, with his hands and cock. Ferns purred in pleasure. She again started fingering herself, and I could see her panties were soaked.

She removed her panties, and held them to my nose. I tried to turn my head, but Fern took my chin and turned me to her. "Open up, dear willow! I opened my mouth. Ferns panties were shoved in. The smell was wonderful, but the stretching of my jaw was uncomfortable.

"That should keep you quiet, dear willow. And hard, I guess."Fern reached down to my panties, and, of course, my small cock was hard again.

"Jason, please set up the bucket and hose," Fern said. Jason went into the bathroom connected to our bedroom, and picked up a bucket from the floor.

He tied a clothesline﷓type rope to the handle and threw it over the door between the two rooms. He walked the rope over to Fern. Fern pointed to her dresser, and Jason brought her a hanger, I recognized it as a skirt hanger, with two clamps on the cross bar. Fern tied the rope from the bucket to the hanger. My eyes must have doubled in size.

Fern noticed my eyes and laughed. "Oh yes, dear willow. I imagine that, as a sissy, you've always wanted real tits with huge nipples. Am I right?" I nodded in silence. "In fact, I bet you've used this hanger on your nipples yourself, haven't you?" I nodded yes. "Well, let us see if we can take that a bit further," Fern laughed.

Fern pulled down my dress and bra so she could reach my nipples. She attached the two clamps on the hanger to my nipples. I screamed into her panties from the pain. Fern simply tugged on the hanger, making the pain worse.

The pain in my nipples was almost unbearable, and my tears flowed freely. Fern ignored them.

"Jason, test the line, please." Jason pushed down on the bucket, and the line over the door pulled mercilessly on the hanger attached so tightly to my nipples. I was sobbing into the panties stuffed in my mouth.

"Now, dear willow," said Fern, "we are going to place a hose into the bucket. The hose will be connected to the faucet in the bathroom sink. As the water slowly goes into the bucket the weight on your nipples will increase. We will see how big your tits can grow."

I shook my head back and forth quickly, hoping Fern wold take my "no" for an answer.

"Oh, don't worry willow. I have allowed for a release before your nipples are ripped off your tits. Maybe."

"I will stop the water the second you cum in your panties. And to help you do so I have a movie for you to watch. Also, I will be stroking your little cock. Up. Then 10 seconds later down. Then 10 seconds later up. I hope that the movie turns you on enough so that you cum soon, for your own sake! Jason please start the movie."

Jason pushed the play button on our DVD player. A movie called "Sissy Self Fuck" started. On the TV was a transvestite dressed in nothing but hose and bra. She had long red hair and enough makeup for a 15 year old girls's pajama party. Her good﷓sized cock was hard, and bounced as she moved. She was sitting on an easy chair, and in her hand was a huge dildo, a good 15 inches long, and very thick. She took the dildo into her mouth, sucking it like it was a real cock. Then she lowered it to her ass, and started exploring her ass with it.

At that point Jason turned on the water into the bucket. Thankfully, he only turned it on to a slow stream. Still, my nipples started to stretch out, and the pain began. Fern stroked my little cock. Up.

The girl in the video pushed the dildo up her ass. She and I both tightened. My nipples stretched further. Fern stroked me down.

The girl in the video started going up and down on the dildo. The pain in my nipples was burning, and my tits stuck out quite far. Fern stroked me up.

In the video the girl was going up and down, up and down on the dildo, tossing her hair in ecstasy. Fern stroked me down, and I thought my nipples were about to come off.

The girl in the video sat down hard. The dildo B all 15 inches B disappeared into her ass. I couldn't believe she could take it. Fern stroked me up and I came like I'd never cum before.

Fern pulled the rope coming from the direction of the bucket, loosening the pull on the hanger. She untied the rope from the hanger, and Jason let the bucket down to the floor. I sighed in relief.

But rather than gently release the clamps from my nipples, Fern simply pulled the hanger as hard as she could, ripping it from my nipples. I sat up with the pain, but Fern pushed me back down. She pointed to the camera, and Jason turned it off Fern then uncuffed my hands. I lay on my back on the floor, feeling the pain in my nipples, on my ass, and in my jaw, where Fern=s panties still gagged me. I wondered what would be my next humiliation.

Fern motioned to Jason, then to the bed. Jason lifted me onto the bed. He kissed my ear, and started licking my neck. Despite my pain, humiliation, and earlier orgasms, I quickly got hard again.

"Excellent," said Fern. She had started the camera again, and was focused on the tent in my panties. She then moved the focus to my face.

Jason straddled my chest, and started stroking his cock. He took the panties out of my mouth. I tried to reach his cock with my mouth, but with him on my chest I could not.

"Please, please Jason," I pleaded. "Let me suck it."

Jason ignored me. Fern then came over, and kissed Jason deeply. She stroked his chest all over, chewed on his ear gently, and grabbed his ass hard. Jason stiffened, and came. His sperm landed on my face. Jason laughed, and said "See, I told you I would give what you needed."

Fern came around to my side, facing the camera. She used her fingers to gather Jason's cum. She told me to look at the camera and beg for it. I looked at the camera and pleaded. "Please, please Fern. Let me lick Jason's cum from your fingers."

"Are you my sissy husband?"

"Yes, dear Fern."

"Will you do whatever I want if I give you Jason's cum?"

"Yes, dear Fern."

"Then so be it, willow. Once you were my husband, now you are a sissy slave who will do anything I dictate. And I mean ANYTHING! Is that right, my dear little pantied slave?"

I looked at the camera, knowing that another border had been crossed, but said "Yes, Fern. I am your pantied sissy husband, and I will do anything you ask."

Fern let me lick Jason's cum from her fingers. "Make "yummie" noises for the camera, dear willow!" I did.

Only later did I realize what Fern's definition of "anything" entailed.

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by Anonymous

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by Anonymous03/03/18

I just came

This is so hot. I am not good at eating ass as I cum the second my nose or tongue makes contact. I need it so much but my balls drain out and I am so embarrassed for my partner to know what I am. more...

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