No Job, No Worries! Ch. 3

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Tom, now Tammy, signs away his life.
8.6k words
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Part 3 of the 3 part series

Updated 09/22/2022
Created 10/10/2000
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Scotsdude
Scotsdude
134 Followers

Strangely, I woke up in my own bed. I seemed to remember being in Sally's room. I looked across at the clock; eleven a.m. Damn, I'd slept for ages. My body felt silky as I realised I was dressed in scarlet satin French knickers with a frilly edge, and matching baby-doll top. I rubbed myself all over and felt good.

Upon getting out of bed, I went to my cupboard. I opened it to find only women's dresses, sexy dresses. I opened the drawer to find only sexy women's underwear. All my male clothes were gone!

The door opened and dad came in. He was dressed in a black corset with suspenders and sexy black knickers. He had his blonde wig on, and lots of makeup. He didn't look too feminine, but for some reason that made me more turned on; the fact that he looked like my dad dressed in women's clothes and in makeup made me really horny.

"I see you've discovered your new clothes. Like them?" He asked.

"Yeah, I do. But, how am I going to go outside in these?" I replied.

"Oh, easily. You are going to be a permanent transvestite, just like me." He saw the shock on my face. "Don't worry, you won't ever need to work, we'll look after you and your sister. Well, I should say your sister and mother will look after us! They are our new mistresses, and I shall be your master."

"What? I'm going to be the lowest in the order?! Not fair!" He slapped me hard on the arse. It brought tears to my eyes, but at the same time my penis twitched.

"I am your master, you will do what I say. Wait, better yet, call me Mistress instead. Yes, you are now called Tammy, so I shall be mistress Paula."

"Yes mistress."

Dad sat down on the bed and pulled me towards him. I sat on his suspender-covered knees. Here are my rules. Like I said, you will call me mistress, or mistress Paula at all times, even in public. Sometimes, when I'm fucking you, I'll want you to call me either daddy or mummy. Okay?"

"Yes mistress." He put his hand inside my knickers and pushed a finger up my arse, then a second, then a third. He talked while he finger fucked me.

"Next. Your friends are no-longer welcome here unless they are willing to stay and become transvestite sex slaves like you." I nodded. "If any of them do decide to join us, then they will have better privileges than you and they will also be your mistresses until I decide a better name for them. If at any time we decide to put you on hormone tablets, you will agree. You will never lose your penis, but we may decide to give you breasts, understand?"

I found it difficult to breathe. This was really sexy, and my dad was finger fucking my arse! "Yes mistress, I agree to everything."

"Good. Next. If you require punishment, then we shall punish you either by pain or public humiliation. You will no longer have sex with any women. Mistress Ann (mother) and Mistress Sally (sister) have agreed they will only fuck you with a dildo. You will not have your penis in anything but a male arse; you are fully homosexual now. You will wear your wig at all times until your hair grows long enough to shape. Keep yourself smooth skinned, no hair. All your clothes are tarts clothes, you will not wear anything else. I can use you for any sexual treatment I like, when I like, where I like. You are permitted to wank, save your cum, as you'll be drinking it at night. In fact, if I decide to wank I'll mix my cum with yours, and you'll drink mine as well. Sometimes I'll have some of my gay friends round, you'll service them as well. I shall buy a new double bed for each bedroom, and the study will now become a sex room, full of toys etc. Mistresses Ann and Sally will sleep together in the master, or mistress, bedroom, and we'll sleep together here. Any questions?" I shook my head in the negative. "Good. I have a contract for you to sign. A lawyer friend of mine wrote it and he'll be the witness to you signing it, basically handing over your life to us, to do with what we please. Will you sign it?"

"Yes mistress."

He pulled down my knickers to my ankles and had me kneel on the bed. He rammed his penis up me, then pulled me down so I was lying flat with him on top of me. He sensually kissed my back, neck and cheek, while stroking my hair. He spoke softly into my ear, in between kisses.

"Now, my little angel. Tell daddy what you want him to do to you for the rest of your little girl life."

He slowly fucked my arse. "Daddy, I want you to treat me as if I was your little gay sissy-boy. I want you to fuck my little girlie bottom whenever you like. I want to have to eat food from a dog-bowl, on my knees. I want you to use me for the rest of our lives."

He increased the pace and was panting now. "That's a good girl. Can you feel my penis up you?"

"Er-huh. Yes daddy, I can." I smiled.

"Do you like it?"

"I love it more than anything daddy."

He sucked on my neck, making love bites as he fucked my arse. Eventually he came hard. Mistress Paula bent down to suck out his cum from my arse. He turned me over and kissed me, pushing the cum into my mouth.

"Swallow it." He ordered. I swallowed, then licked my lips. "Come on, get dressed. We've got places to go."

He left the room. I took off the nightclothes, and put on some red silk stockings, and a red basque. Over it I put a short red satin dress, which revealed my stocking tops. I put on the black wig, and applied lots of makeup. I really looked a tart. Near my makeup (which had also been left during the night) was a gold ankle bracelet. I put it on my left leg.

I went downstairs where everyone was eating breakfast. I was really nervous. I said, good morning to everyone and was immediately slapped by a leather paddle by my sister. "OW!" I screamed.

"It's good morning mistresses. Understand?" Sally screamed at me.

"Yes mistress Sally; please forgive me."

She nodded. "You have food there." Pointing to the dog-bowl on the floor. It was normal food, but I had to eat it with only my face. I got down on my knees and ate. I tried not to make a mess, but I still had to wash my face and put on fresh makeup after.

Mistress Paula told me that he and I were going to the lawyers and other places. I was really, really nervous about going out dressed as a woman, especially with my dad, who didn't look anything like a girl dress in women's clothing. Dad was wearing a long white dress with a slit up the skirt right up the side. I could see his white stockings underneath. I wanted to make love to him so much.

Whilst we were driving, dad kept rubbing my legs through the satin dress.

"You'll phone you friends when you get home Tammy. Tell them all to come round. We'll tell them what we want of them, those who want to stay, can, those who don't, we'll try to convince."

I stared at him. "Please don't invite them round, Mistress, please."

"I like when you beg. But it's not going to work this time."

We arrived at the lawyer's office. Inside a beautiful secretary was typing something. She looked up.

"Ah, Paula, how are you? So this is Tammy?" She laughed, "He looks so funny, yet so sexy. Shame he's gay."

My head dropped. I loved girls, but I also wanted this life.

A door to an office opened. "Paula, hello." I young man in a suit came out. He was tall, good looking, with slicked back black hair. He came over to dad and kissed him full on the mouth. He lifted dad's skirt to reveal a lovely pair of white silk knickers. The man rubbed dad's penis through the knickers.

"My god, Paula, you look terrible." He started kissing dad all over his face and really pulling a grabbing on his penis. "You look like a man dressed in women's clothes. You stupid tart." He was really insulting him, and my dad was getting off on it. The secretary came over and rammed two fingers up my dad's arse causing him to bend towards the man. The man continued to call my dad names and humiliate him, while the woman finger-fucked dad's arse, at the same time rubbed herself with her left hand. "You are such an ugly bitch. These sexy clothes on you? Huh!"

Then the woman started. "Fucking tart. You want me to finger fuck you, don't you? I'm not going to finger fuck you, I'm gonna fist you bitch."

The woman inserted the remaining fingers then made a fist inside my dad's arse. He looked like he was in real pain, but when I saw his face, I saw he was enjoying it. I saw cum dripping from his knickers.

Suddenly, the man grabbed me, bent me over the desk, pulled down my knickers and rammed his penis up me. He fucked me like a mad man it really hurt. Meanwhile, dad was bent over next to me while the woman tried to force as much of her arm up him as possible.

I had tears in my eyes from the pain. My dad saw this.

"Take it you stupid bitch." He screamed at me. Causing me to cry more.

I felt the man's penis twitch inside me, as if he was about to come. He suddenly pulled out and told me to turn around. I did as I was told. He rammed the penis into my mouth and came hard. I tried to swallow it all but some dribbled down the side of my mouth; I quickly scraped it back inside my mouth and swallowed. I cleaned up the man's dick.

The secretary pulled her arm out of my dad's arse and went to wash her hand. She came back and touched up my makeup.

I turned out that the man was a mate of my dad's, he was the lawyer who had prepared the contract. My dad quickly signed it, I already noticed the lawyer, Mark, had signed it as a witness. I looked at it thoroughly. I basically agreed that I, voluntarily, gave up all my rights, and to serve my parents and sister and anyone else my parents agree on. That I would never wear male clothing again (however, then contract was to be renewed every five years, to fit in with law), to never have sex with a female again, and that any male can have sex with me whenever they felt like it (in other words, if a man wanted to take my arse, then I had to let him). I signed, even though I only read the first of a massive sixteen pages. I was now an official slave. I had given up my body and everything with it.

On the way home, we stopped to get my ears, nose and belly pierced. While we were there, the woman suggested that I have my eyebrow pierced as well. She suggested many other places but my dad said that could wait for now.

When we got home, Mistresses Ann and Sally were out. I did as I was told and called my friends. They said they'd be round in ten minutes. Then I went up to my room with my dad. He told me to get undressed. I did, and he started pulling out things for me to wear. I put on black fishnet stockings. A red with black lace edged, lace up basque, and matching panties that covered my bottom. I looked like something from the Moulin Rouge song. After, I corrected my makeup.

Finally the doorbell went. I opened the door to Michael, James and Phil. They were really shocked, but came in. "My god, Tom, what have you done??"

I looked down at my feet in embarrassment. "I'll explain later. Please go and wait in the lounge." As I looked back up at them, I noticed James' penis had made a tent in his trousers.

Two more guys, and three girls to go, they showed up moments later; same shock, same routine.

My dad came into the room, causing even more shock to my friends. We had already gone over what was to happen; dad was to explain everything to them.

"My wife, daughter and I have made a deal with Tammy here, that he will now become our sex slave. He will only have sex with men, or from dildos. The women of the house, of course, are the main mistresses, and us men the lower. However, I am Tammy's mistress. He has signed a contract that hands over all his rights to his mistresses, he signed out of his own free will. What will happen now is that I will forbid Tammy from seeing any of his old friends." They just had a look of shock as he spoke; eyes occasionally glancing towards me. James still had a tent in his pants, as now did Phil, Stewart, and Kevin. Sarah shuffled occasionally, as if she had an itch to scratch. My dad continued, "Now, I'm offering you the opportunity to join Tammy here, and become our slaves. You will, of course, become Tammy's mistress as well; Tammy is slave to everyone. You girls will become slaves to Mistress Ann and Mistress Sally, but will become our mistress. Those who want to join, have to sign a contract to join us. Those who don't, leave now please."

Michael got up straight away. "You people are weird!" He shouted at us, and left. Kevin also got up, he had a massive stiff dick, but was undecided about whether to stay. My dad walked over to him and rubbed his dick. He shuddered but shook his head and ran. James said he was in, "My parents live miles away anyway."

"Yeah, fuck it, I'm young, and this seems like fun. Who'll know? You're all my friends anyway."

Dad told me to sit on the far sofa. "If you are in then go and feel up your slave." James and Stewart came over to me to feel me up. They rubbed my dick through the soft satin material. Sarah came over, stripped off her clothes and started franticly rubbing her clit.

"Does that mean I can't have sex with a man?" Julie asked.

"Not at all," my dad answered. "You just can't have sex with us. You can use a strap-on dildo on us, but you can't have sex with us. But you will have to obey Mistress Ann and Sally."

"And where are they?"

"Out."

Julie decided that she was in and started kissing Sarah.

Last were Phil and Cheryl. They were brother and sister and both lived with their parents. "We can't just leave and not see them again, they would get angry. But we really want to join you." Cheryl said.

Phil continued. "I fancy Stewart anyway, so this should be fun. But like Cheryl said."

Dad seemed to think about that a moment. He told everyone to wait where they were. Moments later he was back.

"Okay, I'll try to work something out for you two. In the meantime, James, you are now Jenny, Stewart, you are now Stella, and Phil, you are now Pippa. Okay?" They all nodded. "Now, women, please strip and go to the master bedroom and wait from Ann and Sally." They went. "Now, you three, strip, go to the bathroom with slave Tammy, he'll put hair remover on your bodies, and then come up to my and Tammy's room."

In our room, dad took out similar sets of underwear as I was wearing now, only different colours. Jenny wore the green one, Stella, the dark blue, and Pippa wore the pink basque. Each hard the black lacy edges and the lace up front, and all wore black silk stockings. But now we were all wearing black high-healed shoes. Dad had a lot more wigs, brunettes, red-heads etc, so the guys had wigs to wear. Then dad and I showed them how to do their makeup. Soon we all looked like tart transvestites, except Stella, who really did look like a woman. However, we all felt good dressed as women, and Pippa said that's how he wanted to stay. "I love the way Stella looks," he said, "but I also love the fact I'm going to make love to you Jenny and Tammy, because you look so sexy as guys dressed up as women. You don't look anything like women, but you still look sexy."

Dad said, "it's true, I like looking humiliating. I like being humiliated, I feel like I'm being used. Do you know what? I'm going to have this bedroom and the master bedroom turned completely into one big bed. We're all going to sleep together in one bed, and the girls are going to sleep together in one bed. I'll have it done tomorrow. Oh, and by the way, don't forget, you are Tammy's mistresses, and I am your mistress."

They looked at me and smiled. All three of them started to feel me up and rub my dick as dad watched. I felt Jenny start to finger my arsehole. Suddenly the doorbell went. "Don't worry, I'll get it. You carry on." Dad said.

So they did carry on. Stella got a couple of stockings from the drawer and tied my hands and feet up, while Pippa rimmed my hole. Then I saw Jenny's dick come close to my hole, Pippa took it in his mouth to wet it, then Jenny slowly pushed it in my arsehole. It was so big and so warm. It hurt like mad at first, but then got really pleasurable. Pippa put her penis in my mouth as Stella started sucking my dick.

After a while, Pippa's breathing became heavy. Suddenly the door opened, and behind it stood my dad, with Phil's parents. Jenny stopped fucking my arse, and Stella stopped sucking, but Pippa just looked into his dad's eyes and continued to fuck my mouth. The others saw this as a cue to continue. Phil's dad looked on in amazement as I was being taken in this sex orgy.

Pippa just decided to go for broke. If his dad disowned him, then he'd live here, if not, then same outcome. "Daddy, come and fuck my arse." Pippa said between breaths. His dad didn't move. "Come and feel your little satin clad boy. Feel me daddy." Finally his dad came over and started to slowly rub Pippa's chest. Then he became more frantic. Suddenly he whipped out his hard cock and fucked his son.

"Okay," He said between thrusts. "You and your sister can live here, but you must never break the contract, and I'll come round regularly to give you a good fucking, understand?"

Pippa glowed. "Oh yes daddy."

He slapped Pippa's arse hard. "It's yes mistress to you. Whore!"

"Mistress? Does that mean you'll be wearing women's clothes too?"

"Only at home with your mother. Your mother is downstairs with your sister. Now shut up and take me all bitch."

And with that, I came in Stella, Jenny came up my arse, and Pippa came in my mouth; then finally, Mistress Carla came in Pippa's arse.

We all went down to check on the girls, when we realised mum and Sally were home. In the master bedroom, Sarah was eating mum's pussy, while being Sally fucked Sarah's pussy with a strap-on dildo, as Julie did the same to Sarah's arse. Cheryl's mum was fucking Cheryl up the arse.

Suddenly Cheryl noticed us watching. She came over and grabbed Pippa's wrist forcing him to bend over and hold on to the windowsill. She then proceeded to push her strap-on penis up his now sore formerly virgin arsehole.

"Now brother, I'm gonna fuck your arse everyday. You fucking tart." Cheryl screamed.

My mum notice we were watching.

"You lot! I want to see some action. Start fucking each other. Paula, take control of your slaves or I'll beat your behind."

"Yes mistress." Said my dad. He then slapped my panty covered arse really hard and told us all to start kissing, sucking and fucking him and each other.

We did as we were told. I got down on my knees and pulled down his knickers. His rock-hard member fell out, and I sucked on it hard. Meanwhile, Stella started licking my dad's arsehole, and Jenny was French kissing him. Pippa's dad came up behind me and started licking my hole; then all of a sudden I felt his penis start to press in my arse. I was really beginning to love the feeling of having a dick in my arse, I'd never imagined it would feel so good.

I noticed Stella now had his dick in my dad's hole. I sucked like mad on his dick, licking the head, and finally he came into my mouth. It wasn't enough for me, I wanted more so kept on sucking and licking till it was completely clean. Suddenly I felt Carla come up my arse. I felt the warm cum shoot up my bowels, then start to run down slowly. Jenny quickly ran behind me and started lapping at the cum dripping from my arse. When Jenny was done I felt another dick at pushing against my hole. It was Pippa. His sister had just shagged him, now he was shagging me.

Pippa really went at it hard, his massive 9" penis went all the way up me. In front of me all the rest of the guys were stood with their panties around their ankles, wanking their dicks. They all aimed at my face as they came, covering me we cum. Then suddenly they had their hands all over me, rubbing the cum all around any exposed parts of my body, some of it getting on the lovely red and black satin underwear.

Pippa had just cum inside me, when we heard the doorbell go. I was told to go and answer it. When I reached the door, my makeup was smudged, I was covered in crusty dried cum, and I was sporting a massive hard-on, covered only by lovely soft red with black frilly edges satin panties. It was Michael at the door. The person I least expected.

Scotsdude
Scotsdude
134 Followers