One Condition

I have the best Mum ever. She has just told me that I can go abroad with my friends this summer!

After she married my dad, Amanda became everything; a wife, a mum, a nurse, cleaner, businesswoman and a slave. She hasn't always been the best; she never really liked me to be honest. Like all relationships, I knew to stay my distance and leave her and dad to it when they were together.

"Guy's! I can go. Amanda said that she will talk to my dad for me!" I had to shout it from my window; I was so excited. My first holiday alone with my friends and it was going to be abroad!

The following morning, Amanda told me that she had spoken to my dad and that he had said that what she thinks will be okay. I jumped for joy; as yesterday, she had said that I could.

"I do have conditions." She added.

"Anything, what is it?" I replied, not thinking about what these conditions were. After all, they were paying for the holiday. At eighteen, I couldn't afford it without them.

She looked at me with a look of glory. "Come with me."

I followed her upstairs and we went into hers and dad's bedroom. I wasn't sure what it was, but it smelt wonderful.

"Sit on the end of the bed." Amanda pointed to the bed. I did as she asked; I was eager to know what terms she had and why they were hidden in her bedroom.

She lifted out a bag with something in it from her wardrobe. Has she bought me a gift? Why would it be hidden?

She turned around with it in her arms; "You can go on holiday with your friends, if you wear this for me for half an hour and complete one more task after." She handed me the bag. Eagerly I opened the bag.

"What the fuck? No way! Not a chance." I basically screamed it at her. I threw the bag on the bed and walked out furiously muttering "Fucking sick bitch!"

As I stormed out of the house, Jack came over.

"Well mate, what did your dad say? Can you come?" He was asking too many questions for what was going around in my head. I gave him a glare.

"Oh, sorry I asked." He basically replied to my look.

I had to rant; "That sick bitch wants me to." I stopped. How do I tell anyone what she wanted me to do?

"Go on mate, what is it?" Now, Jack was intrigued.

Jack had been my friend for ten years; ups and downs, but always there for me. When my mum died, he was with me every day and we have been that way ever since. I think I can trust him.

"The bitch wants me to wear a dress for half an hour, then I can go!" I was so angry. She said I could go not a few hours before.

He looked at me half blank and all he said was; "Are you serious?" I just looked at him. "Oh." He continued; "In public or private?"

"Just in front of her." I sat down on the curb and put my head in my hands.

He looked at me as though I was thick. "Well, then. It's in private, for half an hour. Just do it, I would. For fuck's sake mate, it's a holiday. I would wear it in the garden singing the hills are alive for a holiday!"

"You fucking do it then!" I said with a laughing tone.

That evening, as I sat in my bedroom playing my game; a thought of "It's only once, you can go on holiday if you do it once." My brain made sense. It's half an hour and a holiday for two weeks; or no holiday. "Yes, but, No. Yes. No. Erm." My brain was having an argument. I couldn't face dinner tonight. No, I couldn't face HER tonight.

"Hey, champ. Don't you want dinner tonight?" Dad was stood at my door.

I better say something. "No, dad. I ate with Jack, and I am still full."

"Right you are. Goodnight then." I heard his footsteps leave. "Phew, I got out of that one." I thought to myself.

I was up most of the night thinking about what I should do. I went downstairs, into the kitchen and Amanda was there making coffee. She had a white dress on that sculpted her body. Although she was a bitch, she did look good. Long blonde hair, tall with big boobs and a tight arse. I could see why my friends wanted to fuck her.

Dad was drinking his coffee and reading the news on his tablet.

Amanda turned, looked and asked; "Have you thought about your holiday, Thomas?" Not in humour, but as a genuine question. How could she ask in front of dad?

"Of course he has, he is a lucky boy to be off on his travels!" Dad obviously didn't know anything.

I had to tell him; he had a right to know. Maybe he could stop this silliness. "Well, actually dad." I went to continue when Amanda butted in; "Me and Thomas have come to an agreement that if he does a couple of tasks to help me, he can go with his friends. Isn't that right Thomas?"

How dare she! Yet, I knew not to continue. Maybe she would call me a liar? Maybe, she wanted us to argue? Maybe, she wanted, well I'm not sure what she wants.

"Yeah, that's right." I sounded exasperated. Amanda looked at me with a satisfied grin.

"Oh, good. It's nice to see you are finally working together." Dad sounded chuffed.

After dad had left for work, I followed Amanda upstairs.

She left her door open and ordered me to come into her room. Upon the bed there was the bag with the dress in again. I looked at it, walked into the bedroom and asked; "Half an hour, that's it?"

She was stood just in front of the wardrobe, I couldn't see her expression, as she was facing it. "Yes, plus one more task."

"What's the task?" I asked, unsure if it would be another I didn't want to do.

"Put on the dress and I will see if I want to. It's a task for both of us. If I don't like you in the dress; you won't need to do the other task." What does she mean, both of us? Oh, well. Holiday here I come.

As I opened the bag, I was still unsure. Here is a teenage boy sitting on his mum and dads bed opening a bag with a dress to wear. As I lifted it from the bag, it was soft and silky; a short, soft and silky dress. Red and black in colour and if I was to see it on a girl; I would want to fuck her. A thought came to mind of her wearing it; that would be fuckable. Fuck it, I will put it on. As I went to leave the room, Amanda stated; "When I come back in, I want you in that dress, lying on the bed. You have five minutes." She exited the room.

I removed my clothing and put on the dress. It was colder than I thought it would feel. I lay on the bed and waited for her to take the piss or something when she came in.

She opened the door and she looked at me on the bed; "Good boy."

My dick decided to answer her; was it the fact she had just called me a good boy, or the fact she was in a tight, shiny, black suit with a zip down the centre? I could see every curve on her body, and it was hot.

"How does it feel on?" she asked me in a soft, yet sexy tone.

"Why don't you just take the piss, laugh and let me go? That's what you want to do isn't it? See how far I will go for a holiday?" I was slightly annoyed. This dress showed I was horny; it was lifting up!

"I want to see you in that, I want you to tell me how it feels." She was stern with me.

I rolled my eyes; "Soft and cold. And while we are at it, what are you in that for?"

Dominantly she made me jump; "I ask the questions; I give the orders and you will do as I say!" My dick again answered; as though to stand to attention to an army captain. "What the?" Before I could finish what, I was about to say, she climbed onto the bed; pushed one leg open and saw I left my boxers on.

"You can take those off now!" I did as she said and stayed silent.

Amanda ran her hand up my leg and saw that I was standing happy; whether I wanted to or not. "Have you seen yourself in it?" She enquired.

"No." I responded. She looked playful and pointed towards her mirror; "Well, go and have a look." As I stood in front of the mirror, she came behind me, put her arms around my waist and grabbed my dick. I went to flinch and move out of the way; but I have thought about her touching me before, my friends all want to fuck her, and her hands were so soft! Amanda rubbing backwards and forwards on my dick felt amazing, I closed my eyes as to relax into this feeling. "Open your eyes! You will watch me, watch yourself and see yourself cum!" She ordered down my ear. As I was watching in the mirror, there was something highly erotic about this view. I was watching her watching me, I was watching her enjoying playing with me, I watched me enjoying her playing with me, I saw a full view of her and what she looked like, and I saw me. I saw me in a dress, having a great time and I liked the look of me in this dress. For some reason, my dick coming from underneath the dress looked, well, nice.

"Not Yet, you can hold it more." Amanda whispered. How the fuck did she know? I had to ask; "How? How do I hold" and before I could finish what I was going to ask, I came all over her mirror.

All day I could see myself in that dress, in front of the mirror. Over and over again. I couldn't concentrate on my work, my game or my bike. I just thought about this morning. I have had a wank off someone before, so it's not that. Maybe because I was watching myself? Maybe because it was Amanda doing it? Fuck knows. All I know is that I wanted it to happen again.

That evening, I was sat there listening to dad at the dinner table; "The one lad said to the other that he thought he saw a spider run under his desk. This poor kid was screaming. He was dancing all around the office asking where it was. It was hilarious." I really wasn't interested, but I needed to look normal. Amanda came in with dinner and placed it on the table. Tonight was chicken. I looked at her in her white dress and saw the black all in one. I could feel my bulge harden again. For fuck's sake, I hope this doesn't happen every time I see her now! She saw my dilemma and sat opposite to me. Without dad noticing, Amanda was using her foot to rub me off. It felt great; not only because it was at the table or because it was my step- mum, but because she was doing it in front of dad. "Mm." escaped my mouth and she stopped instantly.

"What's that son?" Dad was looking at me now.

"The chicken, it's great. Mm" I looked at him with a smile.

He laughed, a hungry boy today then, hey?"

"Very." I answered with a look at Amanda.

When I got up the following morning, Dad had already set off early. Amanda must have gone shopping as her car wasn't here either. I took it upon myself to go into mum and dad's room. I stood there in front of the mirror and looked at myself. Nothing different about me, I look the same, but I don't feel the same. I started to mooch through Amanda's things. She had different types of toys and gadgets that I presume please her; different sets of dress up clothing and some other things that I didn't know what they were. I had an idea. I went to check that Amanda's car was still out and went back into her room. I took out a schoolgirl outfit and took it to my room. It smelt of her and I could imagine her in it. I dropped my jeans to the floor and started having a wank with her skirt in my hand. Imagining it was on her, I found myself rubbing harder and faster. I lent on the bed as I could feel my climax run through me. "Oh, Wow, yes! Fuck me, I want you." With that, I came all over her skirt.

I heard Amanda in the kitchen, hid the skirt under my bed and went down to her.

"When you have finished with the skirt, I want you to put it on for me." Amanda said while putting away the shopping.

"What? What skirt? I don't know what you mean."

"The one I have just watched you wank into." She looked at me with a devilish look. Was she serious? Did she watch? Hey, did she like watching? I could feel my horror burning my face. "Don't be embarrassed; go and get it on; and the top" She insisted. I want to know what she will do this time; so, I went upstairs and came down in the outfit.

She looked at me in a way of "What to do with you." I could see her thinking. Have I shocked her by just doing it? Have I actually got my own back on her by doing what she asked? YEY!

"Come here boy!" She ordered. I went to where she was standing. She looked surprised as she put her hands under the skirt and felt that I had no boxers on. She smiled, looked and whispered; "Good pet. You have pleased your mummy." There we go again! My dick bouncing for joy in her hand. Did I just cum to her saying that? I never knew that was a thing! Does this mean every time she speaks, I am going to meringue everywhere? Oh, I do hope not!

With a giggle, she looked at me; "It's okay, it's just excitement. Here." She lifted her skirt and grabbed my hand. My hand slid between her legs and rubbed her sex. She was wet and warm; she was rubbing herself using my hand. She let go of my hand and allowed me to carry on. "Mm, yes. Good boy, keep going." Fuck me that sounds hot! I carried on and felt her knees shaking. Was she cold? "Oh, yes. Good, good, OH!" and with that she shook and came all over my hand. She didn't finish there. She sat upon the table, opened her legs; "Fuck me, hard." She directed.

"Wait, what?" I couldn't believe this. Was this happening?

"Get over here and fuck me, now!"

I didn't need to be told twice. I walked over, stood between her legs and she pulled me into her with her legs. As I slid into her, I had a rush of "Wow, why, how."

As if she could read my mind; "Just go with it, fuck me. I will help you. Fuck me." With that, I started moving in and out of her. "Faster!" she screamed. I did as I was told. I could feel myself get excited, I could feel her squeezing me, I could feel her moving with me. I could feel. What on earth? "Oh, my, wow, Oh, yes." We both came at the same time. The rush of her against me at the same time as me into her was amazing. I collapsed on top of her.

"That was fucking amazing!" I couldn't help but say it. Amanda laughed. "It was good for your first time."

"How do you know it's my first?" I was surprised, can she tell? Was I that bad?

"I didn't, but it was your first with me." She said rather pleased with herself.

After a shower, I went out to see Jack.

"You lucky fucking bastard!" he said as I approached him.

Quizzically I asked; "Why? What's happened?"

"You said that you had to wear a dress and that was it. You didn't say you got to fuck her too!" He hit me on the arm.

"What? I, I." I don't know what to say.

"Don't you say you haven't. I just saw you." He said with a bounce. "I would fucking dress up to fuck your mum! I can't believe it how long has it been going on?"

"Just this time." I lied.

"Lucky bastard." He kept repeating. "Hey, if I dressed in a skirt, would she fuck me too?" I hope he was joking. "Nope, not joking." He added; as though he heard what I thought. It's bad when your friend knows what you are thinking.

"I don't know. Maybe I shall ask her." With that, I went inside, I told Amanda that Jack had seen us and that he wanted to know if he could do the same.

"Bring him here." She pointed to the kitchen floor and went upstairs.

Both me and Jack were in the kitchen when Amanda came down. She had two outfits. One for each of us.

"Choose one and put them on." She looked between the both of us. We both looked and chose a set that we wanted to try.

Jack had a Burlesque style skirt and top and I had a wood nymph dress. Looking at Jack in the set actually looked quite cool. He looked at me and then at Amanda.

"Before you kiss me, you will kiss him." She said to Jack. Jack didn't need to be asked; and as I knew it would be worth a kiss for what she would give, I went along.

"Now, worship me!" She exclaimed. "You must call me mummy though."

She took us both upstairs and, in that moment, I realised. It wasn't only the fact of me fucking my mum that was great; I liked the excitement of being someone else. Anyone but me. I liked dressing up as someone that isn't me. We now had a stronger bond; her fantasy, my fantasy and now Jack's; and we can have it all together. I wasn't sure how long it would last, or how we would now think. All I knew is I was fucking my step- mum with my best friend and that I liked being in a dress while doing it. Does this mean that I am not fucking my mum with my best friend; as I am not dressed as me? I don't see me or Jack as gay or cross- dressers; I just like the idea of fucking as someone else. Who knows where this will go, but I like it. A fantasy that I never knew I would have; and its great.