Trixie's Chastity 01

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Trixie's lessons begin hardcore.
3.3k words
4.4
133.6k
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Part 1 of the 3 part series

Updated 10/21/2022
Created 12/30/2012
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Part 2: Trixie learns his new role.

Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town.

After I made the choice of submitting to her feminization training, there really was no going back for me.

Today my new cock cage arrived, and Goddess let me put it on right away.

It's wonderful. It's smaller and tighter than the last one, but so much more comfortable. Its nickel plated steel. Much less rough than the leather harnesses. She also ordered a very slim, heavily veined 12 inch dildo for me. And I was told to put it in myself and hold it in with a gaff while I finished up the day's housework. Every now and then she will key the remote control on the dildo, and my asspussy will quiver to whatever level of vibration she wants me to receive, and for as long as she wants.

Goddess has had my sissy cock locked up for 2 weeks now and I've been more attentive to details as I learn to please her better and she hasn't had to punish me for almost 3 days, so today I am allowed to wear whichever breast forms I choose as a reward. I went with the big size 11 forms and my black lacy longline bra with the sheer bouncy 38DD cups. I love this feeling, too. The weight and sag of the heavy silicone forms move along with me and make me feel so feminine. Goddess knows this turns me on, and ridicules my cock trying to get hard in its prison of the day. And that only feeds on itself as my cock refuses to behave itself.

As my attempts at erection finally end and I begin to soften, the feeling is more of pleasure than relief. I have somehow have learned to wait patiently for Goddess to reward me with an orgasm.

I hope that as I please her more, she will take mercy on me and let me earn my sexual release.

This morning when she got home from her date, she tied me spread-eagle to the bedposts, then straddled my face and allowed me to clean her pussy of all the cum she'd gotten at their party.

I brought Goddess to what I hope were several good orgasms, and concentrated on her pleasure, rather than dwelling on my bulging sissy cock straining against the steel chastity cage I have been wearing during my sissy maid training.

Although I'd eaten every one of my own sperm loads I've been allowed to release since Goddess caught me dressed in sexy lace, this was my first taste of another man's sperm, and I wondered how many men she had last night. Not that it mattered to me. I had to do what she wanted, or face complete personal and professional humiliation if Goddess exposed me to the world.

So far the only people I knew of that had knowledge of my submission to her were her girlfriends, and her sister. But this afternoon while I was kneeling before her lapping pussy again, she was on the phone to someone telling them every detail of my frilly maid outfit and what I was doing for her. It sounded like they were planning something, but most of the conversation was from the other end, so it was hard for me to follow.

I bathed her after dinner, and she told me to shave and shower. Then I was to put on what she was laying out for me on my bed. I was given 30 minutes to get dressed and then report back so she could do my makeup. I said, "Yes Goddess. Thank you for allowing me to wear makeup tonight and feel more feminine. Thank you for allowing me to wear my big breasts today, too."

She laughed and went to her room to dress.

I found the same breasts and bra from today, a black lacy garter and sheer black stockings. They felt so good sliding onto my smooth legs. I quickly got into these, and then had to squeeze into a tight pink ballerina outfit with frilly tutu. My garters and cock cage were in full view, as was most of my ass. Goddess spent several minutes on my face, and when I looked in the mirror, I saw a different face than mine. I was a whore with dark blue heavy eye shadow, exaggerated lip liner and crimson lipstick. Thick mascara and then she gave me a real reward. A short curly reddish blond wig made me actually look like a female. I was really starting to feel like one, too.

I was given a pair of white open toed stiletto 4 inch heels to wear. This was another treat for me. I hadn't had nylons & shoes or a wig on since my wife caught me and became my Goddess.

When she was ready, she clipped a chrome chain dog leash onto my new metal cock cage, and led me to the door.

She was taking me outside dressed like this? When I started to protest, she slapped my face, hard.

"Shut up, slut boy. You wanted to serve me and please me so I won't tell everyone you used to know that you love wearing women's underwear and jerking off all day. Well, it will please me if you shut your fucking sissy mouth and do what I tell you. We're going to meet some people. You have already earned another week of chastity, just for questioning my orders. Well, Trixie girl, are you ready to go with me and do as you're told? Or would you like to have your little useless thingie caged up for the rest of the month?"

My face still stinging, I said, "Yes, Goddess. I'm sorry. Please take me with you and let me serve you."

"That's better, slut-boy. You're going to have a lot of fun tonight, slut. At least I will," she said as we left the house and got in the car. I was carrying a large gym bag she'd had waiting by the front door.

She drove. I was glad because I could barely stand in these high heels, let alone drive in them. Driving across town, she told me coldly, "You are going to experience several new things tonight, my little sissy slut. And I want you to pay attention and learn. Don't be so stupid as to argue with me in front of people. The punishments you get for Doing it at home will seem like fun compared to what I'll do to you if you fail me even once tonight. I've told them you are broken and subservient. Do what I tell you, and do it cheerfully and the very best you can."

"Yes Goddess, I will. I want to please you, and I won't let you down," I said, as we turned into the driveway of a big estate.

She parked the car, and we walked to the door. Of course I was worried about what was happening, wondering who she knew at this place, and what they had planned for me. She pulled the car up to the front portico, and a valet opened her door and helped her out before doing the same for me. We went up the steps to the big house, Goddess in a tight fitting black spandex dress showing off her womanly curves. I tottered along behind her on my spiked heels on my leash.

The door was opened by a beautiful and very tall uniformed maid, who curtsied and asked us inside. There were several couples and a few singles scattered about the large room we were in, and I could hear more activity around the house. The maid asked my Goddess if she would care for anything to drink while looking me up and down.

She asked for a glass of red wine and handed my leash to a statuesque brunette seated on a couch with 2 gorgeous blondes, whispered something to them, and told me to behave myself. Then she left the room and me standing before the women like a slave at auction. I realized I was standing, and awkwardly sank to my knees before the beautiful women on the sofa. Every now and then the plug in my asspussy would randomly vibrate for a while, making me squirm and fidget.

The women were chatting about their work, and mostly ignored me as I waited for whatever was going on here to be revealed to me. I was in no hurry. Whatever was on the agenda for me was probably going to be uncomfortable. But I had to be patient and follow whatever Goddess told me. I'd been warned not to embarrass her tonight and she had all those pictures and DVDs of me at home over the past 2 months. My former life was over, and I was accepting that.

Goddess finally returned with a very large black man and an evil grin on her face. She took my leash from the brunette and handed it to him while introducing me.

"Lance, this is my sissy toy Trixie. Will you take him and get him ready, please? He's very eager to begin further training." She asked, giving him a sloppy kiss and rubbing her chest against his big broad one.

Lance snapped his fingers and the maid reappeared. He said, Tammy, take Trixie downstairs and set him up on table number 3. We may be a while, so not too tightly, like you did last time."

"Yes Master, as you wish." The maid said, taking my cock leash from him and leading me out of the room and down a long flight of stairs.

The heels were giving me some trouble on the staircase, but I gasped when a door at the bottom was opened. The room was large and dimly lit by several large candles, with rough stone walls and every sort of kinky bondage device and toy I'd ever heard of and more hanging from racks. There were several benches, chairs with restraints, chains hanging from the ceiling. A large wooden X with straps was on another wall. In a dim corner I could see a metal cage that had someone inside wearing head to toe red latex. Arms bound in a latex straightjacket, hood with the mouth zippered shut, and eyes covered. This poor creature followed the sound of us moving about the room but made no sound. I was terrified. What the fuck was this?

There were several sofas and easy chairs scattered around, and racks of dildoes, vibrators, clamps, and much more in all sizes.

The maid motioned me to a heavy wooden bench and told me to kneel on it. She put black leather wrist and ankle restraints on me and padlocked them to iron rings on the corners. This left me on my knees with my chin resting on a lightly padded vinyl rest and my tits hanging down. Then she left without a word. All I could see was the creature in the cage, and wondered what he or she had done to be punished like this. My cock was bulging in its cage as I waited for my fate.

After an hour or so, Goddess came into the room with Lance, another black man, and the maid.

The maid removed the plug and put in a larger one as Goddess told me "Tonight you take another step in your training, whore. Since you like the taste of your own cum and the creampies I let you eat out of me, tonight you will see how much better it is right from the tap. So thick, warm and gooey. You're going to love it, slut, and I'm going to enjoy watching you suck off every man that wants your sissy mouth. I've also set up a rate chart for the men to pay me each time they use you. Since you are unskilled, it's only ten dollars for a blowjob, and fifty dollars to fuck you. Of course, the first man to take each hole will pay double for the privilege of taking your virginity." She had a wicked smile on her face and a hand was stroking Lance's bulging crotch.

The other man said "I get that mouth first, right?" He handed Goddess a twenty, then pulled out his cock as bright lights came on and I saw there were several cameras in the room. Most were aimed at me tied and helpless as I stared at the thick black cock hanging before my face. It looked like a dark brown beer can, and it wasn't hard yet. He moved closer till it was touching my lips.

Goddess moved behind me and said "Kiss it Trixie. Lick that big cock and make him believe you want to suck it. Ask permission to suck that cock."

"Please sir. May I suck your cock?" I whimpered. This got me a sharp blow across my ass with a paddle as Goddess said, "You worthless cunt. Why did you ask HIM? You belong to ME. Remember?" WHACK. And a few more spanks before I came to my senses and begged her. "I'm sorry Goddess. May I please suck his cock?" She whacked me once more, and told me to go ahead.

I licked the sagging foreskin of the huge dick until the purplish head poked out. The whole thing was growing impossibly big before my eyes. I wanted to touch it, but my hands were tied, so I had to accept it into my mouth at his pace. Apparently the new plug in my ass was also inflatable. Goddess was pumping it up and the pressure was getting unbearable. When I groaned around the stiffening meat in my mouth, everyone laughed. The guy grabbed my head and pulled me onto his cock as he just held his hips firm. His cock was still growing and gagging my throat. Goddess had allowed me to suck her strapon cocks, but she didn't have one as big as this. It was much softer than even her big jelly one, and I could feel it was alive. The guy let go of my head and told me to just bob on it. "Yeah, that's it. Oh yeah. Just like that, sissy boy. Suck my cock you faggot slut. Take all of it. In and out, yeah, just like that. Don't stop till I tell you to. He said to the others, "This whore is a natural."

His cock was still expanding in my mouth. Goddess was releasing some of the air in my butt plug, and teasing me with pumping it back up, larger each time. I was scared to find out just how big it would go.

I had no idea how big the cock I was gagging on would get, either. But the guy was breathing hard and tensing up as he grabbed my ears and held me down on his shaft. Most of it was stuck down my throat as his balls convulsed and shot his seed into me. His shaft was pulsing, and although I couldn't taste the first few blasts, he kept spurting as he pulled me away from it. My mouth was filling up, so I had to swallow a lot of it before he pulled out completely. A few more squirts landed on my face before he finally stopped cumming. Sperm was drooling from my chin and eyebrow as Goddess told me to lick him clean.

Then the guy zipped up. Goddess pumped up my plug another impossible notch, and set it to vibrate before they left me. The camera lights dimmed when they closed the door.

I'd just sucked a man's huge cock and swallowed most of his semen. And my cock was so hard I started to cry. My ass and prostate were so sensitive my balls tried to ejaculate, but I didn't believe I could. And knew Goddess would be furious if I was able to without her permission.

Then I remembered what Goddess had said about the men upstairs. I tried to recall how many I'd seen up there. It probably didn't matter. But there had to have been at least eight more, unless more arrived. I was going to be used by as many of them as Goddess wished.

Perhaps an hour later, the door to this dungeon opened and the bright camera lights snapped on again. I couldn't see much, but I could hear several voices and felt someone finally remove the plug from my asspussy. Someone climbed onto the bench behind me and Goddess sat before me, watching my face as something large pushed against my rear opening. Her face was a mixture of curiosity, amusement, and disgust as whoever was behind me put the first real penis into me. He slowly pushed it in and I thought I was being split apart until I felt his thighs rest against my butt cheeks. Goddess laughed, looking into my eyes she asked, "Do you like being fucked Trixie? Do you just love being a slutty fuck toy for my real man friends?"

The guy behind me was sawing his hard dick in and out of me now, and I DID like it.

"Yes, Goddess. Yes I do love it. Thank you for letting your friends take my virginity."

I was actually enjoying getting buttfucked while my wife watched these men use me, dressed and made up as a slutty whore. She looked around the room, and satisfied the cameras would catch all the action, she moved off to the side, allowing a very fat stocky man to stand before me. He dropped his pants and put his short fat cock against my lips. With no real choice, I kissed and licked it hard while the guy fucking me picked up the pace. His hips slamming against mine as he bottomed out with each deep thrust into my rectum. The fat guy grabbed my head, and held me as he shot thick wads of jizz into my sucking mouth, then pulled away, making room for a tall skinny dude. This guy's cock was very long, but not much thicker than a hotdog. As soon as it was pushing into my throat, I felt the guy behind me tense up. A few more deep strokes into me, and I felt him hold it inside me balls-deep as his cock pulsed over and over, filling me with his load. I loved this feeling almost as much as I used to enjoy cumming inside my wife.

Another cock pushed into me before I could moan about the empty feeling back there. I felt like such a slut. If Goddess was trying to punish me, I doubted it was working. I loved it. The skinny guy pulled out and emptied his nuts all over my face as the new invader pumped my butt. Another cock appeared before me, and I greedily sucked it into my mouth...

This went on for what seemed like hours. But after I watched my wife straddle a huge black cock while sucking another, and they both came all over her, Goddess stood before me as the last cock pulled out of my stretched, gooey cunthole. My cock was raging hard in its cage as I followed her command and licked all the sperm from her body after someone unshackled me.

Goddess told me to get a quick shower, since it was only midnight, and a few of the boys wanted to take me to the local adult video arcade for a few hours.

"Good thing I brought you another outfit, Trixie. Everyone is just going to LOVE this one..."

2

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jennifurzoejennifurzoealmost 4 years ago
Be careful what you wish for(even subconsciously).

Trixie sounds like she's about ready to turn trix and bring Mistress money for her own feminization.

devilspy2001devilspy2001over 10 years ago
Yes

Now this is how you break in a new sissy cuckold chastity boy. The writer did not say, but that boy had to be dripping out of his cage a lot. I love breaking in a virgin pussy on a sexy ass cuckold. Making him moan and beg for more fucking. Then make him beg to be bred like I breed his wife. Sissy training is so good. Cannot wait to read the next chapter.

AnonymousAnonymousover 10 years ago
Really really dumb

So what if he's masturbating? When she takes pictures, just take them back and divorce the bitch. Who would put up with a woman that wanted to blackmail you? Totally unbelievable baloney.

ElizabethOliverfieldsElizabethOliverfieldsabout 11 years ago

Hey sally_spandexcd, if you are going to join Trixie don't forget me. This sissy bitch also wants - or should I say needs - to be made a sissy slutty slave by a real man.

AnonymousAnonymousabout 11 years ago

wish I was going to the glory hole to suck all kinds of cock.

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