tagTranssexuals & CrossdressersHow I Became Sissy Willow Ch. 03

How I Became Sissy Willow Ch. 03

bywillow619©

I slept on the floor next to the bed that night, still in the lingerie and sundress I'd worn the day before. Fern and Jason, of course, slept together in the bed. As I drifted off to sleep I kept thinking about the events of the evening.

I had been put in women's clothes by my wife, Fern after she found a magazine I forgot to hide. The magazine showed a transvestite being tortured and humiliated by a couple. Fern, who had never shown any interest in my crossdressing had now made it her goal to turn my life into something approaching the pictures in the magazine.

Of course, she also chose that opportunity to introduce me to Jason, her lover of a year. Jason quickly became my lover, and then my tormenter in partnership with Fern.

What bothered me most was that I had promised Fern I would do anything she demanded. And the emphasis she placed on the word Aanything" made me truly worry about what lay ahead in my future. Unfortunately, my worries proved well﷓founded the next day.

We all woke about the same time in the morning. Fern looked over at me and laughed."What a sight you are today, willow!"

I'm sure I was. My blond wig had fallen off. There was still cum on my face from Jason, and my own cum had soaked through the clothes.

Fern jumped out of bed, and gently kicked me in the rear. Into the bathroom, sissy willow!"

I went to the bathroom, and Fern followed me. I stripped, and Fern handed me a bottle of lotion. "This is a depilatory. Rub it all over your body below your neck, wait 15 minutes, then shower it off. And that includes your dick and balls, too!"


I did as she said. Heck, I'd come this far there was no point in fighting this latest development. I rubbed the lotion on my body. As I did so the unmistakable sound of our bed creaking came from the bedroom. It was clear from the rhythm that Jason and Fern were making love, and rather strenuously at that.

I waited what I thought was 15 minutes before getting on the shower. I must have guessed right, because the shower washed all my body hair away. Here I was, getting my body ready for further feminization, and my wife was fucking her lover in our bed. I still couldn't answer the question in my head; was this what I had wanted in my fantasies? It had already gone much further than I'd ever dreamed, and yet ...

Well, I had no choice now, anyway. The video Jason and Fern had shot thus far ensured my continued cooperation. I washed the hair on my head, turned off the shower, and stepped out to dry off. The bed was still creaking as I dried myself.

I wondered whether I should stay in the bathroom till they were done when I heard Fern yell "Willow ... get ... out ... here!"

I went into the bedroom, and there was Fern, astride Jason, who was on his back thrusting up into her pussy, lifting her entire body as he did. Fern held her palm up to Jason, and he stopped.
Fern pointed to the chair, and said "Put those things on, willow." There was a black longline bra and black panties. The bra came down halfway to my hips. The cups were medium sized, but very well padded. Lace trimmed the top of the cups. Though the panels on the bra were of a lacy material with stemmed flowers raised up from the material, the wide ribs between the lace panels were stiff and strong. Again I put the bra on backwards, but it was so tight I had trouble turning it around.

When the cups rubbed against my nipples I realized how really sore they still were from the last night's torture.

The panties were of very high quality. Heavy material, but very smooth and soft. Lace trimmed the leg holes and waistband.

As I was dressing Fern had moved onto her back on the bed, and Jason was about to mount her in the traditional position. Fern pointed to the dresser. "There on the dresser is a bottle of nail polish I chose just for you. While Jason shows you how a real man fucks a woman, I want you to paint your toe nails."

I went to sit in the chair, but Fern pointed to the floor next to the bed. "I want your face to be at just the same level as we are, so you can get a good look." Of course, she didn't have to add that it was more humiliating to be on the floor than on the chair. The polish was red. A guy would call it fire engine red, but the cosmetics company called in "Fantasy in Red." It was very bright and shiny.

As I sat on the floor Jason started to really pound into Fern. She was thrashing around in pleasure; a sight I had never seen during our lovemaking. It took me 15 minutes to paint my toe nails, and Jason was still going hard. I waited another 10 or so while the polish fully dried, and still he was going strong. Despite my position, I was quite impressed. Then he drove deep into her with one final thrust, and both screamed in unison as they enjoyed a joint orgasm.

Jason gently lowered himself onto his back on the bed. He looked over at me and chuckled. "I guess she liked what she saw, Fern." He pointed to my panties, where my little cock was clearly quite hard. I started to rub it through the panties, and Fern leaped out of the bed and slapped me across the face, knocking me over sideways.

"From now on, willow, you will not touch yourself in that manner unless I say you can. It will not be that often, I assure you. And there will generally be some interesting things going on when it happens. But it only happens when I say so. Is that clear?"

"Yes, Fern." My face stung, and my erection had shrunk from the shock and pain of the slap.

"Now Jason and I are going to shower. While we do so you will change the sheets. Put on the good satin ones. When you are done that, you will squeeze fresh orange juice for us. Is that clear, willow?" Fern asked.

"Yes, dear," I said.

'Hmmm. Should I let you call me dear?" Fern mused aloud."Yes, I think I will. I still love you, after all. And do you still love me, willow?"

I responded that, of course I did, and for some reason added "I would do anything for you."

Fern's smile reminded me of the promise she extracted from me last night. "I think you probably will, but we shall see if you really mean it."

Fern turned to Jason. "Should willow call you dear, as well?"

Jason thought for a few seconds. "No. Not yet. I don't think one fucking and a blow job quite add up to her calling me dear. We'll see what the future brings." Jason and Fern smiled at each other. I did not like those smiles.


As Fern and Jason showered - giggling and gasping all the time - I removed the old sheets and took them to the laundry room, placing them in the washer and starting it. I then made the bed with the satin sheets. These were our special sheets, reserved for (what I had thought) were our special nights in bed. Now I was setting them on the bed for my wife to enjoy with her lover.

I then went downstairs to squeeze the orange juice. When I returned, Jason was wearing jeans and a rugby shirt. Fern was similarly dressed, with a slightly different shirt. Seeing them dressed like a couple drove home my new position in this relationship.


Fern pointed to the bed, and told me to dress in the clothes that were there. There was a black leather skirt, white blouse, and black pantyhose, which I put on first. My red toe nails showed clearly through the hose.

The skirt was nearly straight, but at least it came to a relatively modest length. Like the lingerie, it was high quality. The leather was soft and supple. Still, the narrow cut would keep me from taking long strides as I walked. It was pleated, with a waist band that buttoned in front, giving the illusion of a belt.

The blouse was also pleated, in the front, with shiny black stud buttons showing. The sleeves were full length, sheer, and a bit billowing. It was an interesting contrast to the tight, short skirt. Neither Jason nor Fern made any comment about my facility with buttoning a blouse with its buttons opposite from a man's shirt.

Of course, my black bra was easily visible through the material of the blouse.

After I put on these clothes I was handed a pair of open toed white shoes. The contrast with the black hose would catch people's eyes, so they would look and see my red toe nails. At least the shoes had moderate heels, about one inch tall.


Fern picked up her keys off the night table and threw them to Jason. "Would you please drive?"

I looked up in panic. "I can't go out like this! At least give me a wig, so I have a chance of not being noticed."

"What a sissy! Always worried about how you look. Just comb your own hair forward, and you should pass. At least from a half mile away, that is." Fern laughed a rather nasty laugh as she said this. "Besides, dear willow, you really have no choice." As she said this she picked up the video camera, and her threat was clear.

Jason took my elbow and guided me down the stairs, out the front door, and to the garage. Though I saw no neighbors, I was sure they were all watching me from behind their windows.

We got into the car (I was in the backseat, of course). We drove for half an hour, finally pulling into a strip mall I was unfamiliar with. At least, I thought, there doesn't seem any chance we'll run into anyone we knew.

It was still early, and there were no other customers walking around the parking lot. Jason pulled up in front of a store called "The Piercing Place." He and Fern got out of the car. Jason came around and opened my door and offered his hand, in an exaggerated show of gallantry.

He put his arm in mine, and we started walking to the store. "You walk well on heels, willow. Have you had much practice?" He chuckled. I did not answer.

Suddenly, he stopped, grabbed both my shoulders in a very tight grip, spun me to face him, and held me tight in front of him. "I asked you a question, young lady" he said quietly but firmly. Between his grip and the serious look on his face I found myself feeling very small and helpless at that moment.


In a soft voice I said "Yes, I do have a lot of practice walking in heels."

Jason's grip eased, the smile returned to his face, and he once again put his arm in mine and guided me to The Piercing Place.

We walked in. I was thankful that we were the only customers in the place. Behind the counter was a very bored﷓looking young lady. She couldn't have been more than 18. Her name tag said "Gina."

She was about five feet, six inches tall. She had long black hair, and her face spoke of an Italian heritage. She was wearing yellow stretch capri pants, red canvas sneakers, and a rainbow striped tube top. She had large breasts that stood nearly straight out, with prominent nipples. A very lovely young lady, and here I was, an obvious sissy, about to have her pierce my ears.

She looked up at us, then focused on me. A wry smile came to her face. She came up to me and said, "Can I help you, Miss?"

Jason answered for me. "This young lady would like a large gold hoop in each ear. On her left ear, at the top, she wants two flowers. Do you have any pansies?" Gina giggled at that. "On the side of her right ear she will have one of your special earrings." I wondered what he meant by a "special" earring. "Oh, and do you mind if my friend videotapes this?" Jason said, pointing to Fern.

Gina agreed to the taping, and led me to a chair. Within minutes I had the hoops and the flowers. Gina then ducked behind the counter and brought out a black velvet jewelry box, about a foot square and flat. She opened the lid and showed it to Jason. I saw him pick up an earring that was shaped like a very realistic penis, and was about an inch﷓and﷓a﷓half long.

"It's almost as big as yours, willow!" Jason said. Everybody laughed but me.


"This has two posts because of its size. Do you want it pointing up or down?" asked Gina.

Everybody looked at me. I know I was blushing, even after all I'd been through. "Well, willow, do you want your penis up or down?" Fern asked. :Up," I whispered. In a very short time it was done, and the penis, pointing up, was in my right ear.

Gina asked "Is there anything else you want pierced for her? Tongue, eyebrow, navel? I'm a specialist with nipples."

Fern put her hand to her chin. "Hmm. Do you think his nipples are good candidates for it?"

Gina came up to me, and grabbed my nipples between her thumbs and forefingers. She rubbed them hard through my blouse and bra. Even though still sore from the night before, my nipples grew hard under her touch. I nearly melted under the touch of this beautiful young girl.

"Oh, they'd be fine. I could do rings, posts, crossed posts, whatever you want."

Fern thought for a second, and said that perhaps the nipples would be done in the future but that that was enough for today. .

Gina pointed to my skirt and said "Oh, by the way, she was right. She did want her penis up." Under Gina's treatment of my nipples my cock had again gotten quite hard, and was making a bulge in my skirt.

Fern smiled broadly and said "Maybe we could pierce that?" My eyes must have grown twice their size. Fern giggled and said "No willow, we won't do that. Not if you behave, that is."


Jason paid Gina and we started to walk out of the store. Gina spoke up and said AI'm just curious. Could I ask what the story is here?"

Fern pointed the video camera at my face, and said "Tell her your story, willow!"

I looked at Gina. Those beautiful dark eyes looked right into mine. "I am willow. I am the pantied sissy husband of Fern. I do anything Fern or her lover Jason tell me to."

"So have you sucked his cock?" asked Gina.

"Yes."

"And has he, umm..."

"Yes," I said.

Fern kicked me in the rear, keeping the camera focused on my face. "Yes what?"she said.

I looked at Gina's beautiful eyes again, and softly said "yes, Jason has fucked me in my ass."

Gina said "Cool. Well come back anytime." Her smile would have melted the coldest heart of any man.

As we left the store Jason again took my arm. There was more foot traffic than there had been earlier. Many people looked our way and stared or laughed. I was amazed that Jason had the confidence in his own manhood to escort me - obviously a man in woman's clothing - and ignore the people around us. My only wish at that point was to get in the car and go home. I got half my wish.


Jason again opened the car door for me. We drove away, but it soon became clear that we were not going home. We drove to an area with a lot of warehouses and used car lots. I was afraid I recognized the area, and when we pulled into a parking lot my fears were realized. We'd driven to the adult book store where I bought my TV magazines.

"I believe you recognize this establishment, willow?" asked Fern. Without waiting for me to answer she got out of the car with the video camera. "Wait here," she told me. Jason and I waited in the car together as she went into the store.

After about five minutes Fern stuck her head out of the shop's door and waved to us, signaling that we should come in. Jason again escorted me to the door. Speaking to Jason, Fern said "All the arrangements are made."

We all walked in. Of course, Nick was there. Nick was almost always at the check﷓out counter. He knew me by sight, but probably never knew my name.

"Hello, willow," he said to me. "Good to see you again." He smiled one of the dirtiest smiles I'd ever seen.

Jason grabbed me by the elbow and led me to the rear of the store, past the books, to the video booth area. "Ever been in here before, willow?" he asked me. I nodded. "But not dressed like that, I suppose, eh?" I shook my head. Where the hell was this going?

Jason released my arm, and began walking back to the front of the store. Fern then took my elbow and led me back into the video booth area. There was nobody else visible, though several of the booths were occupied.

Fern got in front of me and talked quietly, her face close to mine. "As I suspected, Nick remembered you when I showed him some of the early part of the video. He told me that, in addition to buying magazines you often would come back to the booths. He was nice enough to make a deal with me."


AI told him about our little video. He's quite interested in seeing it, and maybe showing it. In fact, he agreed to let me shoot some of it here. This is the plan, sissy, and you WILL follow it, or Nick won't be the only one getting a copy of the video. You are going to go into the third booth on the left. That is one of the booths with a hole to the next booth. What do you call them?"

"Glory holes," I said quietly. I knew the booth well. Though I was always too scared to actually do something there, it always excited me to watch or be watched through the hole. And when another man would stick his cock through I would quickly cum while looking at it, even though I never touched one.

"Well, willow, I am going to film you in all your glory. You and I are going into that booth. I am going to pick a video for you to watch, then leave. I will close the door. Do not lock it. I am going to find a man with a large cock for you to suck and put him in the next booth. When his cock comes through I want you on your knees with that cock in your mouth. I will then open the door and film this. Is this clear?"

I was about to protest when Fern put a finger to my lips. "Shh, dear. You said anything, and I meant anything." I nodded, meekly.

Fern led me to the booth. We both fit in comfortably. She had obviously reviewed the titles earlier. She put a ten dollar bill in the machine and quickly pushed the channel button to the video she'd chosen.

It was not a TV or shemale video. Instead, it was an all male film. There was one young man tied over a locker room bench. Four men in leather pants and jackets were with him. One was fucking his ass, another was fucking his mouth. The other two waited their turns, stroking their large cocks.

Fern closed the door. Less than a minute later a large cock came through the glory hole. I hesitated for a second, and Fern opened the door. "Now, bitch!" she said.

I got on my knees and wrapped this strange cock with my tongue. Fern started filming, and I could tell by her angle she got both me and the gay film she'd picked in the view.

I licked the cock up and down, up and down. I took it all in my mouth, and held it deep in my throat. Then I started taking it in and out, in and out. I lost myself in the delight of pleasing this strange cock, until Fern spoke to me.

"Now, sissy. Now you may play with yourself. But do not cum until I tell you to." I started to rub myself through my clothes. But Fern was not satisfied. "No, willow, take that little cock out of your panties, lift your skirt, and let the camera see you jerking off."

I did as she ordered, though it was a miracle I did not cum immediately. I continued to make love to this strange cock, and after five minutes or so it erupted in my mouth. I started to swallow, and heard Fern urge me to swallow every drop. I did so, and the cock withdrew. I tried to see who my unknown lover was, but he did not walk by my booth. Fern then told me to stand up and put my back to the wall the hole was in. This put the video screen to my left.

"Now, willow, I want you to watch the video and finish jerking off. When you cum, make sure you catch every drop in your hand. I will, of course, keep filming."

She now was shooting me jerking off watching the man on the bench getting fucked in both ends. It took almost no time for me to cum, though, to be honest, the video was really not the reason. I caught it all in my hand.

"Turn this way, and lick your hand clean, willow." I looked into the camera and did as ordered. When I was done she turned off the camera. Suddenly Jason appeared at the booth door. Fern asked him what he thought.

"Great," he said. "Best blow job I've had all day." I was surprised - and thankful - to learn that it was Jason's cock I had sucked. I'd always worried about catching a disease if I handled a strange cock in here, and was relieved that that worry was gone on this occasion.

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