My New Life Ch. 02

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New life for closet sissy.
2.6k words
4.47
40k
30

Part 2 of the 3 part series

Updated 06/08/2023
Created 12/17/2017
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The next thing I remembered was waking up, tied to a chair, in the guest bedroom. I tried to get out but my legs had been tied to the chair legs as well as each arm being tied to the arms of the chair. I couldn't yell for help because a big, ball gag had been tightly placed in my mouth. As my eyes started to adjust, I noticed a letter on the table next to me.

'Dear Stephanie,

I hope you're awake, by now, and realize the predicament you're in. I've decided we both need a real man to make us happy. That's why I'm on a date with Jerome. Don't worry, I still love you with all of my heart but I don't know if I can accept this side of you. After talking with Beth, I've decided, since you like to dress up as a woman, you and Jerome are going to be my new 'sissy maids', and you'll be my 'fucktoy'. Beth will be by later to get you ready for us after we get back from dinner. Relax and enjoy the ride of new life.

Love Veronica'

I started to fight my binds as hard as I could and screamed into the ball gag, hoping someone would hear me. I was crying because I knew my life had come tumbling down. I sat there trying to figure out what to do. I didn't want to be a 'sissy maid' or a 'fucktoy'. I was a man and needed to prove it!

************

As I continued to fight to try to get loose, I heard the front door unlock and heard a voice as the door closed.

"Stephanie, sweetie! Where are you?" Beth said, followed by an evil laugh.

As she opened the guest door, I started squirming and fighting as much as I could but to no avail. She walked in, carrying a big bag, and sat it down next to me.

"Wow! Veronica wasn't lying when she told me she'd caught you like this."

She pulled out her phone and started to take pictures of me all dressed up and tied to the chair.

"You're a perv, aren't you? I'd always suspected there was something fishy going on with you and I never did want you to marry my sister."

After taking the pictures, she walked over to where I was sitting and slapped me, hard, across the face and saw the surprised look on my face.

"That's for what you did to my sister, you faggot! Now, let's get you ready for your evening, Princess."

"Veronica told me to give you the works, tonight, before they get home. We'll start with makeup, followed by hair and nails and, finally, we'll get your outfit ready."

Beth started to work. She grabbed my right hand and started to give me a manicure, attached deep red nails to my fingers and switched to the left hand to do the same. She moved to my toe nails so they'd match my fingers. Moving to my makeup, she removed the makeup I already had on and reapplied it.

"You need to pay attention as you 'will' start to do this every day."

She started with a powder base that matched my skin. Then she added black eye liner, silver eye shadow, false eye lashes and coated them with mascara.

"I'm going to remove your ball gag to add the lip stick. Not one sound or you'll regret it! Understood?"

I nodded my head 'yes' as I knew I was in no position to negotiate. She showed me the color of the lipstick...a bright, almost fire truck, red.

"This will be perfect for wrapping your lips around Jerome's dick!" Beth laughed.

"Eventually, your hair will be long enough to style but, for tonight, we have to stick with a wig."

She went over and pulled out a gorgeous, auburn wig with a slight curl near the bottom. As she started to adjust it to my head, the curls came down past my shoulders. Satisfied, she moved away. I couldn't see myself in the mirror because she'd turned me away from it while giving me the makeover.

"I have one more thing for you before we finish getting you ready for tonight."

She went over to her bag and produced two large, hoop earrings.

"Veronica doesn't want me to do this to you but I can't help myself," Beth said with a wicked smile.

"There's no use fighting. You can't go anywhere and you really don't want me to pierce the wrong spot, do you?" she said as she started to walk over to me.

I shook my head 'no'.

"Good girl. You're learning your place."

She pierced both of my ears. The weight of the earrings was noticeable but there wasn't any discomfort.

"We have one last thing we need to add," Beth said with a sly smile.

She went over to the bag, grabbed something and walked over to me.

"We can't risk ruining your image as a 'woman' by allowing you to get a nasty boner!"

She produced a pink cock cage! I started to struggle but it was no use...I couldn't do anything. She lifted my dress, lowered my panties, attached the cage around my cock and balls and locked it into place.

"There, that'll help keep your cock from getting hard and both Veronica and I have a key to it. We're almost ready for your big night. I'm going to let you go so you can get dressed but don't try anything or there 'will' be consequences."

When she let me go, I slowly stood and started to walk over to her. I was bigger than Beth so I figured I could man handle her and get away. I grabbed her by the arm in order to spin her around and tie her hands when, out of nowhere, I felt a shock that sent me to the floor. Beth was standing over me, smiling, with a Taser in her hands!

"You didn't think I'd come unprepared, did you? I knew you'd try something stupid!" she snarled.

The next thing I knew, she gave me a swift kick to my gut, knocking the wind out of me.

"Are we going to behave, now?" Beth asked.

I couldn't speak, as I was trying to catch my breath, so I nodded 'yes'.

"Great! Now, go get dressed!"

I walked over to the bag to see what I was going to be wearing that evening. Inside, there was a blue-black shimmer, off the shoulder, mini dress; silver, peep-toe, five inch heels; a brand new, dark-blue, 42DD bra with a matching thong and, last but not least, a pair of 42DD breast forms.

"We're going to glue those in place," Beth said.

She grabbed the adhesive, applied it to my chest, applied the breast forms and held them into place. When she let go, I felt the weight of my new 'boobs'. After I'd finished dressing, Beth held up a full-length mirror in front of me as I stood there, staring at 'Stephanie'.

I spun around a few times, admiring my new look. My cock was trying to get hard but the new cage prevented that and it was started to become uncomfortable. I tried to get it under control by turning away from the mirror but it didn't help because I was extremely turned on.

"Alright, let's get you into position for when Veronica and Jerome get here!"

She led me into the master bedroom and told me to kneel. After I knelt, she tied my legs together and used the slack to tie my hands behind my back. The final touch was the big, ball gag and a blindfold.

"I hope you have fun tonight but don't forget...I have pictures! One misstep and they'll go viral to all of your friends and co-workers," Beth whispered into my ear.

Then she walked out of the room and closed the door. I eventually fell over from kneeling for, what seemed like, four hours. I heard the front door open but no voices. As I strained to listen for any voices in the house, the bedroom door opened.

"Aww. The slut fell over," I heard Veronica say.

The door closed, she walked over to where I was lying down and she leaned over.

"How's my little bitch doing?"

The next thing I knew, my blindfold was taken off and my wife, wearing a stunning red evening gown, and Jerome were standing over me.

"Jerome, this is my sissy husband, Stephen, or should I say, Stephanie!"

I saw Jerome smiling and, what looked to be, a huge bulge in his pants.

"Sweetie, why don't you get comfortable on the couch while I talk to Stephanie," Veronica said to Jerome.

Jerome left, leaving me alone with Veronica.

"Here's what's going to happen, tonight. When I told Jerome you'd jacked off to him, he was very interested in meeting you. So, we've come back for you to entertain both of us, tonight. You relax and I'll come get you, shortly."

Veronica left the room...leaving me alone, again. What could I do? I was tied up, dressed as a woman, and not knowing what was going to happen next. About an hour later, Veronica came in and untied my legs.

"Follow me," she said as she led me into the livingroom.

"Kneel," she commanded as she tugged the rope attached to my arms, forcing me to kneel in front of Jerome.

"Well, since you've fantasized about him so much, here's your chance!" she said.

As Jerome started to unbutton his pants, Veronica removed my ball gag, which allowed me to stretch my jaw. As I did, Jerome lowered his boxers and out sprung a huge, nine inch cock!

"Please, don't make me do this!" I begged.

"But this is what you wanted, isn't it?" Veronica laughed.

All I could do was stare at Jerome's cock as he pushed it toward my bright red lips but I turned my head.

"Bitch! You'll do what you're told!" Veronica sternly said.

Jerome started to force his cock into my mouth but, once again, I turned my head. This time Jerome got pissed and slapped my face, nearly knocking me over.

"This is what you wanted, you stupid slut! You 'will' take my cock and be appreciative!"

Jerome motioned Veronica over. She stepped behind me and grabbed my head as Jerome tried, a third time, to make me suck his cock. That time, as I tried to fight, Veronica kept my head straight and Jerome attempted to push his cock between my lips but I kept them closed. He kept pushing and, eventually, they got sore and my mouth opened. Jerome took the opportunity and rammed his cock into my mouth, making me gag.

"That's it slut! Now, start sucking!"

He started to get into a groove, ramming his cock down my throat. My tongue began to drag along the underside of his cock as he thrust it between my lips and Veronica tightened her grip on the back of my head. I could tell Jerome wanted our time together to last. I slowly began to bob up and down on Jerome's raging, hard cock, taking it in nice and slow. My tongue kept wiggling around his monster cock and he was loving it. Veronica loosened her grip but I kept bobbing up and down with the speed and rhythm Jerome had set.

"Damn! This bitch is a natural!" Jerome moaned.

He started to speed up, forcing his cock deeper and making me suck faster. I continued to slurp as drool started to roll down my chin and the sides of my mouth. I felt his cock start to twitch as it exploded and coated my mouth with rope after rope of his cum.

The force of his ejaculation nearly caused me to choke as it rushed down my throat, and filled my mouth, as he slowly started to slide in and out of my mouth, again, coaxing the rest of his cum out. He pulled out and, before I could catch my breath, Veronica shoved the ball gag back into my mouth, leaving it full of Jerome's cum.

"Swallow it, now, slut!" Veronica said as they both stared at me.

It took me a few attempts but I was, eventually, able to get all of it down.

"That's a good girl! You still have a long way to go but that's a good start!" Jerome said.

Veronica helped me get up, as my hands were still tied, and walked me back into the bedroom.

"He was really impressed with you," she smiled.

She sat me on the bed and took the ball gag out.

"I'm extremely tired. Am I done for the evening?"

"Hell, no, you're not done! Stay right there," she replied as she untied my arms.

She walked into the closet and returned with two, matching pink babydolls.

"Here, put this on," she said as she handed me one of the babydolls.

I took it, stripped completely naked and put on the babydoll but left my peep-toe heels on. Veronica told me to put my hands out in front of me and handcuffed them together.

"What are you about to...?" Veronica stopped my sentence as she put the ball gag back into my mouth.

"Jerome. We're ready," Veronica called sweetly.

Jerome walked into the room, started to remove his shirt, walked over, threw me on the bed and Veronica leaned in close to me.

"Jerome wanted to take my anal virginity but I offered him yours, instead," she whispered.

As soon as I heard that, I started to thrash around but, by then, Jerome had me pinned down. I screamed into the ball gag as I felt my asshole, unwillingly, begin to expand as Jerome pushed his thick cock into my ass.

Veronica laughed at my facial expression as the realization hit me that there was a real cock thrusting in and out of me. Tears welled up in my eyes as he gripped my waist, under my babydoll, and pounded my asshole. He pulled out and, again, rammed his rock-hard cock into me as I screamed into the ball gag.

After the pain subsided, somewhat, he started to get into a rhythm and slowly pumped his cock into me. As he did, I started to push back onto his cock as it started to feel good. We got into a nice rhythm, with him fucking my brains out and me moaning into the gag.

"God she has such a tight ass!"

"Let's see if we can get this bitch to cum like a sissy," Veronica suggested.

Jerome gave a deviant smile as he changed positions and laid on his back. Veronica positioned me on top of his cock and lowered me onto it and his cock slid into me much easier that time. Jerome started to buck and told me to raise up and ram my ass onto his cock and start riding it.

As I did, Jerome started to move faster and faster. I kept the rhythm of lifting and lowering myself onto his cock as he continued to pound my ass. Sweat started to run down his face as his grip tightened on my hips and he buried his cock deep inside of me.

Suddenly, as his cock spasmed inside of me and knowing he was depositing his seed deep inside of my ass, a warm pleasure went throughout my body. As he continued to cum, I started to shoot load after load through the cock cage and onto his chest. I was screaming into the ball gag in pure ecstasy as I had never felt this type of orgasm before. Then, everything went black...I'd passed out, still impaled on his cock.

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4 Comments
AnonymousAnonymousalmost 6 years ago
I hope there's more to 'cum'.

For the standard platform of the 'caught & forced cuckold', this is a pretty good start.

It's a bit brief, but all the elements are here.

Thanks, hon.

AnonymousAnonymousabout 6 years ago
Changes

To help Jerome become more feminine are they going make him take hormones to become more feminine if I were like Jerome that is what I would want

AnonymousAnonymousover 6 years ago
Visions

That was so beautiful. I was imagining everything that I read. Good story. x

lingerie65lingerie65over 6 years ago
Jerome's side order

I Was surprised as realization hit me like a fucking freight train ! An when must sister in law shows Up, anda does my Lake Up in preparation for my evenig fuck by Jerome with my wife in high presance ! Why was she doing this shit to me, just because i was fantazising about then guy who was making passes @ her, while I was fully dressed like a woman and stroking Off.

Even to cruelly force me to suck a mans 9 inch thick cock, even though I wound Up finding it so delicouse, It was still wrong & then I'm basically fucking raped while my bitch of a wife not only watches but cheers ir on, at after that horrible pain was replaced by the imense anal pleasure, I felt some what better, also.while at the gym other day a beggar blew me a kiss, was I becoming more feminin by the by the day , since Jeromy now fucked me constantly durring the day & at night when he gives it to me, Inch by meaty inch he does it so gently and does it like my lover, and a true gentleman after my heart (I'm beginning to fall in list with him)

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