Two Conditions

I am here with my best friend Jack; both of us with a secret not to be told. She has made sure that we don't tell it. You see, my mother has told us that we can both fuck her; if we are dressed as someone else. She says that it isn't wrong if we aren't fucking her as us.

I am eighteen and Jack is nineteen; we have been taught tricks that you could only imagine.

"Thomas, get in here, she is waiting for us!" Shouts Jack through the hallway.

I walk out of my room, down the hallway and into her bedroom. Jack is already on the floor with his collar around his neck and in his leather pants. I drop my gown and kneel beside him.

"Nice of you to join us!" Amanda governed. "For this unsuitable behaviour, you will be punished!"

Although some of her punishments are nice, I in protest decided to try and explain myself; "I-"

"Shut up and stand! Both of you!" She demanded. "Turn and look at me."

Me and Jack turn immediately; Amanda doesn't like to wait.

She was dressed in a leather look dress, crop in hand and a leather glove in the other. What the fuck is the glove for? I never asked; I was in enough trouble.

"Kneel." She looked at Jack. He did as he was told.

"You will stand and watch." She was looking at me.

She stood in front of Jack and pulled his head in-between her legs. We now knew what that meant. As jack was working his tongue in and out, up and down, round and round; mum was throwing he head back. She looked fit as fuck when she did that. I loved watching her cum.

"Stop." Jack continued. "Stop, you greedy boy. Stop, or I will punish you." As she hit his ass with the crop. Jack came up with a "Ah!" as he rubbed his ass. I started chuckling. She looked at me, sat at the edge of the bed.

"Finish what he started. NOW!" She demanded.

I did no more than tease her with my tongue. She started to stiffen and tighten; I knew she was close. I entered my finger and started to rub; just above the entrance to her perfect vagina; while still teasing her clit. "Oh." she moaned. She hit me with the crop to make me stop.

As she stood up; "You will stand and watch." She ordered me to move back. My dick was as hard as iron; and it was showing through my leather pants. "You, come forward." She looked at Jack.

She bent over the edge of the chair and Jack stood behind her, awaiting instruction. Mum pushed backwards and Jack slid straight into her. He grabbed her ass and started pounding into her; just how she liked it. "Fuck me boy!" She shouted and Jack got quicker and harder. Just as his legs started to shake, she pushed him backwards and threw him on the bed. She sat on top of him; this time with his dick in her ass. "Lucky bastard" I thought. As she was riding Jack, she turned and looked at me and smirked a sexy and tormenting grin. Jack couldn't hold it anymore and came with a scream. Amanda carried on regardless, started to stiffen and then came with her head thrown back and a satisfied smile.

She got off Jack, walked up to me and put on the glove. She stared to cover the glove in her juices and then grabbed my dick in the hand with the glove on. Rubbing gently and slowly; I was covered in her juices. I don't know why, but with the glove on; a hand job felt fucking brilliant! As I started to move with her; she stopped, took off the glove and handed it to me. "Sit, play. This is your punishment."

I put on the glove and started to masturbate; she and Jack were watching. This glove felt like I was fucking her; but not at the same time. As my thoughts came to her and Jack fucking not moments before, I came. I took off the glove and looked at her for her next instruction. She stood in front of me and started to play with herself.

"Both of you, watch." She went to her draw and pulled out a dildo. Rubbing it up and down her sex, she started to moan. She inserted the tip and started to slowly push it inside her. Me and Jack were both hard again!

As she got faster with the dildo; she stopped and looked at Jack. "Come here; fill this hole." She bent over the chair; looking at me. Jack was fucking her, and she looked at the glove again. I picked up the glove and started to rub myself again. Mum started to rub her clit as Jack was fucking her. "Oh, yes. Fuck." She was going to cum again. As I thought that; mum and Jack came together.

"You, boy will continue to masturbate until I say you can stop!" She and Jack left the room.

"What the fuck? Where's mine? She has never not let me ride her. She loves my dick!" I am furious. "Fuck this, she can't see. I will sit here until she comes back.

Ten minutes later I heard Jack leave and Amanda was coming up the stairs. I started to play again. SLAM went the door. "You are a very naughty boy! I told you to carry on until I told you too."

"Wait, what? How do you-?" I tried.

"See that up there" I looked up. "That is a camera, and I can see that you have not done as you were told." She sounded angry rather than dominant.

"Sorry, mum. I won't do it again." I didn't know what to say.

She stood me up, turned me around and smacked my ass three times in the same place. No rub in-between each one!

"Ah! Fuck!" I cried. "What on earth?" I screamed.

She was furious; "You are my favourite dick, and you can't play the rules. Your father will be back any minute and I haven't had you deep inside me!" She dragged me out of the bedroom and threw out my robe along with me. I still had the glove.

Later that night, I heard mum and dad at it. I rolled my eyes; knowing that one; she wished it was me and two; that I hadn't had any! Since me and Jack started fucking her, we never missed a day. Mine and Jacks holiday was coming up; that would be long enough without her!

I laughed to myself; after all, this wouldn't have happened at all if it wasn't for the holiday. Ironic that for the holiday; I dressed up as a girl and fucked my mum for the first time. Now, I would ditch the holiday to stay and fuck her.

I felt a hand run up my leg; I woke instantly. I knew her touch on any part of my body and my dick stiffened without needing any prompt.

"Good girl." I heard her say. So, now I am back to playing she-boy.

She came up the sheets from the bottom, sucking the tip of my dick as she came up. She put a finger over my lips before I could say anything and sat down on my wood.

"Mm." escaped her mouth. "I have wanted this all day." She started grinding on me and I started moving in and out. She liked the two motions together, and I was good at it. As she was about to cum, I tuned her over and took charge. I pulled her up slightly and made her look at me as I entered her ass. I started pounding into her and she started to rub her clit at the same time. "Finally!" I thought. "Oh, yes. Good girl, keep going." She cried. I got quicker, harder and more excited. As we came together; I saw mum had left the door a jar; she got up and left.

The following morning, Dad left for work and Amanda had made pancakes. I gave Jack the morning missed call to tell him Dad had left, and he came straight round.

As me and Jack ate our pancakes, we heard mum tell us to come on upstairs. We did as we were asked, and as usual; there were outfits to wear on the bed for us.

For Jack, there was a cowgirl outfit and for me there was a native Indian dress. These were a new fetish; I liked it when we tried new things; no matter what they are.

"I want you both to fuck me. One at the front and one behind." She exclaimed. "Come on!" she ordered.

We needed to use our imagination here. "You lick her, Thomas, and I will play." Jack took charge of the turn on. I nodded.

As we felt her get wetter and wetter, Jack inserted himself into her tight pussy; I was still liking and teasing her clit; catching Jack on occasion. Jack pulled out and went for her ass. "Oh, fuck." Amanda moaned. I let Jack settle before I entered her wet and ready to pound pussy. We nodded to each other and started to move in sync; me inside her, Jack out; Jack in, me out and we continued this until we could all feel a build of pure pleasure. With Jack inside mum's ass and me in her pussy; it felt like we were all fucking each other; it felt tighter and more personal. As we were about to cum; me and Jack pulled each other in, so mum was completely full. The feel was unreal and all three of us came together. "Ah, fucking hell!" Me and Jack exclaimed together. Mum looked very sated as she looked at us both, smiled, pinched our ass' and went to shower.

That evening, Dad didn't look to impressed and told me that he wanted an early night with mum.

"Have you had a bad day dad?" I asked him.

"You could say that son, you could say that." He answered.

That night I couldn't sleep; all I could here is mum and dad at it louder and longer than usual.

"What the fuck is going on? Dad never lasted that long." I whispered to myself. Mum was moaning and screaming, and my dick got harder and harder. I loved the sound of her. With her sound and the picture of what she looks like when she is enjoying herself; I used to glove to have a play; after all, it's a waste otherwise!

The next morning, mum was in her nightgown and dad left with a smile. Lucky bastard; I hope she still has some energy left for me.

I went upstairs to phone Jack and on my bed was a memory card with a note; "Watch this, dad."

I inserted it into my computer and went white. I feel sick. I feel-. "MUM!" I shouted and she came running up the stairs.

"What's the matter? Are you okay?" She was flustered.

She looked at the screen and her face dropped. I handed her the note and she sat on the edge of the bed.

"Makes sense why he fucked me the way he did now." She admitted.

"Hey, guys, why no call? I just saw your dad leave." Jack was stood at my door. We both pointed to the computer screen.

"Isn't that us yesterday?" He questioned.

Me and mum both said "yes" at the same time.

The video was showing me, Jack and mum fucking in our cowgirl and Indian dresses. The film stopped and then we saw dad. Dad said; "This is how it's done boys." It then showed dad banging mum in many different positions and making her orgasm many times. Fuck me; she was hot.

"I have to learn how to do that!" I exclaimed. Mum and Jack were not impressed.

"Now, boys. I have two conditions to propose. You can confront me, or; you can go on holiday and fucking stay there. Your choice." The video went blank.

"How did he?" Amanda went to say.

"The night you came to my room, and you left the door open a bit. He could have seen then?" I looked at her with questioning eyes.

She replied; "I never left your door open; I'm not that stupid."

"We are off on holiday tonight, Thomas." Jack stated. "Will you be, okay?" He was looking at my mum.

She nodded. "He wouldn't have fucked me if he was in a mood about it." She continued; "You boys get ready for your holiday; we can talk about it when you get back."