My Son In My Clothes Ch. 02

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Mum takes charge of a dressing up session.
6.5k words
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Part 2 of the 3 part series

Updated 10/30/2022
Created 11/25/2012
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"Right, here goes," I mumbled to myself.

We stood face to face on the landing.

"You've nicked your leg," I said.

He looked down at the little trickle of blood. He went back into the bathroom wrapped in one of my fluffy pink towels.

"Well, I guess you need to find some underwear. Go ahead, and put something on, I don't want to see your, thing. I'm just going to put the car away and lock the front door."

I gave him 15 minutes to find something to wear.

I stood looking at Kevin, and slowly my face dropped. I shook my head a little, and then looked up to his face. He looked a little apprehensive, and his grin seemed almost apologetic. I looked back down to his chest, and saw my pale blue bra. I gulped a little at the matching blue panties, and the tan coloured tights he was wearing.

"Kevin, where did you get those from?" I asked faintly.

"From, the chair, over there," he replied quietly, as he pointed in the corner.

"Oh, yes, what I mean is, well, I wore that to work yesterday, they are dirt, dirty," I stammered.

"Well, you did say I could choose?" he said softly.

I nodded and coughed clearing my throat.

"Yes, but, I thought, no I meant something clean, from my underwear drawer."

I moved forward and went to the dressing table just to get away from his eyes. Now, somehow, this didn't seem a very good idea. But I was going to persevere.

"Okay, what dress do you want to wear?" I said, pulling open my wardrobe doors.

There was a silence that felt incredibly awkward. I waited with my back to him. Eventually I turned round. He stood with my white blouse and short black skirt in his hands. I gulped again, and so did he.

"Mum, can I?"

"Darling, I wore to work, I've got a clean blouse and skirt if you want to be a.....waitress?" I said, finally digging the last word through my mind.

"I want to wear this mum, please?"

I turned back and closed my wardrobe.

"Fine, put them on," I said, managing not to choke on my faint words.

Well this was a lot bloody harder than I thought it was going to be. I mean with all the clothes in my wardrobe, sexy, pretty clothes, why did he want to wear the uniform that I had sweated in for 5 hours? I took a deep breath just before I turned round. There he was wriggling into my skirt! Right, time to compose myself. I had told myself earlier that if this was going to work then I would let him have freedom to choose. Besides I was going to make this day unforgettable for him, in a way that I thought would stop all this.

"Wait, something is missing," I said.

I emerged from the bottom of my wardrobe with two tennis balls. Kevin's face looked a little shocked as I walked towards him. I pushed them into the cups of my bra that my son was wearing!

"Not as big as mine, but they will do," I said smiling at him.

He nodded and looked down. When he looked up he gave me a little embarrassed smile. He pulled on the blouse as I stood watching.

"Tuck the blouse into the skirt, like I do," I instructed.

When he had finished I moved forward and opened a button on his, sorry, my blouse.

"It is good for the customers. They tip better if you show a little cleavage and a lot of leg."

His face was a little red now. I guess my plan was starting to work. I stood back and looked him over slowly. Again this was part of my plan to humiliate him. Even so, he had quite a good figure for a boy pretending to be a girl. He was the same size as me, apart from the hips, and my god, he did have quite good legs.

"Now, shoes, well I don't think you'll fit into mine. I guess I'll have to phone my sister, she has slightly bigger feet than me. Well what do you think?"

I turned my back to close the wardrobe. I know I shouldn't laugh, but I had to force myself to stop. Still, my plan had worked, and he had rushed out of my room. Now perhaps this would stop. I took a deep breath and gave Kevin a moment to himself. I went to tap on his bedroom door to explain that it was okay, and he shouldn't feel ashamed. My hand dropped slowly and so did my expression. Kevin stood there in a pair of black court shoes with a 4 inch heel!

"I bought them the other day, what do you think?" he asked as he twirled round with a big grin on his face.

He walked past me and back to my bedroom before I had a chance to close my mouth, let alone come out with something. Okay, this wasn't going to plan straightaway, but soon he would be grovelling, and begging me to stop. I pointed to the stool in front of my dressing table. He had a little triumphant grin on his face. Okay, this was a battle of wills, and I was one determined woman when I wanted to be. I started to make his face up while he sat there with his bloody legs crossed. Still I wasn't going to be beaten, and he could have his little victory, for the few minutes it would take to do his makeup.

"Do you pluck your eyebrows?" I asked, genuinely shocked at not noticing before how well shaped they were.

"No, I just shave them a little, getting rid of stray hairs, and keeping them under control around the edges."

Again he had that quite chuffed look on his face. Mummy hadn't noticed how clever he was, god if he was a real girl I don't think we would be friends for very long, conceited little bitch! I gave him just a light coating of light blue eye shadow, and then two nice coats of black mascara. No foundation, he didn't bloody need it!

"I use cream most nights on my face," he said smugly.

I put the spot stick down after not finding a single spot. So that was why he spent nearly 20 minutes in the bathroom every bloody night!

I put a light brown colour on his lips and even they seemed to be too full to be true. I watched him grinning at himself in the mirror. He couldn't even hide the fact that he was enjoying this now. I must admit after a few minutes, I had done a good job on his face, and perhaps that was my downfall here. God you stupid bitch I thought to myself.

"Thanks mum, I look really good," he said, with a little wrinkle of his nose.

I brushed his long blonde hair out, not a bloody split end anywhere! Right, let us see what you think of my next move then I said in my head. I reached over and hit the button on my heated rollers! His eyes shot to mine in the mirror, and then he had to turn round and look at me.

"Mum, you can't be serious?" he asked, with a little shocked face.

I waved my hand in a dismissive gesture like it was no big deal.

"Just a few soft bouncing curls, just to make you look really pretty when you serve me lunch, sweetheart," I said sweetly.

"But, how will I get them out?" he said in a panic filled voice.

"Oh silly, I expect your hair will only look a little kinky for a few days."

"A, a few days, but, I'll be back at school," he mumbled.

"Well some of the girls might notice, but I doubt if the boys will. Just tell them you slept funny or something, I'm sure you'll think of something, won't you?"

I gave him a big confident grin that he couldn't quite return in the same manner.

"Now, while the rollers are heating up pick some earrings to wear," I said with another smile.

He rooted around in the box and finally he looked up, again a little worried.

"Mum, um, you don't have any clip on earrings," he mumbled.

It was then he saw the pin in my hand.

"God, mum no!"

"Oh don't be silly, your aunt and I did each others ears when we were teenagers. I'll get some ice from the freezer, it won't hurt that much."

His eyes were all over the place.

"I can't, I just can't," he whimpered.

He ran off to his room again. Well it seems I didn't have to take this as far as I thought. That was until he sat down and put two large gold hoops on the dressing table. He picked one up and pushed the flat pad. The thin part of the hoop went up into the gold part, and when he let go it sprang out again.

"See, this is how they work. You just pull that back and it springs forward trapping your ear."

"Yes, well I know that, okay, but first I want to do your hair. We'll give you a few loose bouncing curls. Here seeing as how you are such an expert, you can do your own nails. I'll be back in 10 minutes."

I went to the kitchen and had a cigarette. This wasn't going quite as I planned. Kevin didn't seem as embarrassed as I thought he would. In fact he was enjoying it a little too much for my liking. Surely he realised I was doing all these things to put him off? Still he had a stubborn streak like me, and maybe he was trying his best not to be beaten. Okay I could live with that, I still had a few aces up my sleeve. When I went back to the bedroom, he was holding up his fingers, letting the air dry the pink nail varnish. He smiled at me in the mirror. I grinned back but not too much. I put the rollers in his hair, and started to tidy up my makeup.

"Oh, have you got some nail varnish remover? I'm totally out, I forgot to get some."

I could see his face drop a little, and then he shook his head.

"Never mind, you'll just have to go and buy some later," I said.

I didn't give him time to protest, I went into the bathroom with his stunned face still firmly in my mind. The rollers came out and I fluffed his hair up. I know I could have made him look ridiculous, with loads of makeup, and a big hair do, but I didn't, he had to believe I was doing this for him, well for the time being. Even so, I was still stunned with my creation. The part about me wanting a little girl was true. With Nick in the navy I thought with a daughter we would have more in common. My sister had two girls, and they sort of became the daughters I never had. But now it seems I had Kevin to take that part, not that I wanted that. Kevin did have quite a pretty face for a boy, and now it was made up, and had soft curls of blonde hair framing it, I had to look hard to find the boy under there.

"Right, what do you think?"

He smiled into the mirror. A tentative hand touched a soft curl of hair. He seemed quite shocked by what looked back at him.

"I look, amazing," he mumbled, in a far off way, "Mum, you've made me really pretty."

I took a deep breath and turned away. I had done what he said I suppose. What a stupid bloody cow!

"I know why you are doing this. But now can you see what it means to me?" he asked.

I couldn't speak. I just looked away and went downstairs. I sat on the couch watching telly, not that I knew what program I was watching, because my head wouldn't stop thinking about what I had done. Kevin walked slowly into the lounge. I looked up at him. He really was quite stunning, all long legs and blonde locks. He gave me a little shy smile that seemed to say so much. Yes, I really had fucked up! I watched him sit on the couch. Even that was done in such a feminine manner that I wanted to scream. He crossed his long legs and sat quietly watching the telly. I felt like I was on a train with other passengers. You notice them when they first sit down, and then you hope they don't talk to you. You know the rest of the carriage will be listening, and you might get asked something embarrassing. But this was my son sat there. I couldn't ignore him even if I wanted to.

"Will you make me a drink?" I asked just to say something really.

He was up on his feet and in the kitchen before I knew it. That was a shock in itself, in boy mode he would huff, and I would have to ask a few times. I watched from the chair as he moved about in the kitchen. From the back he looked just like a real girl. Even his ass looked good! When he came back in with a cup of tea, his tennis ball tits jiggled a little. I even caught him watching them.

"So, what do we call you then?" I asked as I searched my handbag for my lighter.

"Um, huh, I don't know," he replied, with a little embarrassed chuckle.

"I know we could still use Kevin, but you aren't my son when you are dressed up like that," I snapped a little.

I said it to hurt him, and to make him think. I think it did but he tried to ignore it.

My fingers found the lighter and something else. The devil in my head smiled a little as I pulled out the name badge. One of the girls had left the restaurant where I worked. She had given the badge to me outside, she told me to shove it up the ass of my Greek boss. She was one of the girls who wouldn't let him get away with groping her.

"Lean forward, so I can pin this to your blouse," I said.

He watched me pin the square gold badge to the blouse. I sat back as he looked down at it. He looked at the black letters.

"Isn't it a little too...."

"No it suits you, Veronica," I said looking deep into his eyes.

His face was a little red, but he nodded slowly. Again he sat on the couch and looked down at the name badge. I didn't have a clue what thoughts were going through his head at this time. But just looking him over with his little feminine looks, the earrings, the shoes and the tights, got my mind working on my next plan. I puffed on the cigarette.

"So, who do you fancy at school then?" I asked.

He struggled with the question a little. I could see his mind running around trying to find what I was getting at.

"Well, um, Jess is really hot, and Marline her friend is nice, but she is a little chubby. I think they are too hot for me though, Wendy is pretty also."

"Oh, and what do you think they would make of you dressed like that?"

His mouth opened but he just couldn't answer. So I continued with my questions sensing I could really get him thinking a little deeper, and maybe putting him off thinking about buying those bloody hormone pills.

"No Veronica, I mean, what boys do you fancy?"

He gasped a little and his face went red again. The tennis balls started rising and falling a little more sharply.

"Well, it isn't a difficult question is it?" I snapped.

"Mum, I just want to say I don't feel, I mean I'm not gay. It is just when I'm dressed up, I feel like a, a girl," he mumbled and then swallowed.

"So, in that case the question isn't a difficult one is it? If you feel like a girl now you must know who you fancy? Go on, which of your friends would you like to have a kiss and a cuddle with?"

His fingers were tying themselves in knots, and his tongue seemed to spend a lot of time licking his lips.

"Okay, I guess Martin is nice."

He stopped and looked at me. I think he was beyond nervous now, worried about what I thought.

"Come on, a hot girl like you must have more than one fantasy guy. I did when I was young. Who would you like to bring home to meet your father?"

He shifted uncomfortably now.

"I reckon you look like Jessica, she is pretty hot. I bet she would have a few boys going crazy over her. Veronica, I bet with those legs sticking out of miniskirt at school you'll have hands all over you."

"God, don't say things like that," he gasped.

"Well tell me then, who else would you like to go on a date with?" I hissed.

"I know what you are trying to do. You are trying to put me off, I won't mum, I like it," he snapped back.

His chest was rising and falling then even quicker now, and he was panting hard.

"Look at you I can see the control tops of your tights. I bet you would flash your legs and maybe your knickers to any boy at school!"

"Oh alright, if you must know, I fancy, Derek, William, and Bryan Alders," he yelled, "and I fancy Mr Driver the English teacher, Mr Harris from next door, and your Greek boss," he yelled.

I sat in shock as he raced up the stairs. I hoped he was just saying that to get at me. I went through all the names he had said, trying not to imagine my son, or rather Veronica with each of them in turn. One name stood out above all the rest. It was quite a shock for me. I took a deep breath and went up to see Kevin. I felt sorry for him now, he was still my son and I felt for him. I sat next to him on the bed.

"Sorry. Kevin, why don't you come back down?"

"Because of what you think, because of what I said," he mumbled as he sat on his bed.

"Look, I'm sorry, I really am, and I shouldn't have pushed you like that. This whole thing has been a shock for me. Come downstairs and you can make me something to eat. Please, Veronica?"

He got up and stood in front of me. I reached out and stroked his nylon clad leg in a friendly gesture. I went to take my hand away but Kevin grabbed it. He held it on his leg. I looked up into his eyes with a questioning look. Slowly he started pulling my hand upwards. I watched my hand gliding over the nylon of his tights. Until Kevin took his hand away, my hand kept going up, ever so slowly under his skirt. His legs were trembling and it gave a big judder as I felt his cock and balls through my tights and panties! For the first time my head was accepting what my hand was doing. Kevin was looking out of the window staring at something. At first I thought he had turned to a statue just because of what was happening. I stood up keeping hold of his cock, and there through the net curtains I saw Mr Harris washing his car. After what Kevin had said about him I looked at Mr Harris a little differently. He was going bald, in his late 40's, but quite good looking apart from his stupid moustache. Never once had he figured in any of my many fantasies, but now I could see there was something about him.

"Well, what do you reckon, Veronica? Do you think he could take on mother and daughter?"

I started jerking the hard cock that was in my hand.

"Have you seen the way, he looks, at, at the girls when they walk past?" Kevin stammered.

"Darling, he looks at me like that," I whispered.

I carried on jerking a little faster. Kevin's legs were barely able to hold him up. No I didn't know why the fuck I was doing this either!

"I bet if I wasn't here, Veronica would go down and help him wash his car. I bet you would love bending over the bonnet, knowing he was stood back with a dirty grin, watching your ass and your long sexy legs," I whispered.

I felt the wet soaking through again. Veronica was clinging to the window ledge. I couldn't quite believe that those same panties and tights I had worn to work, now had spunk in them from my son!

"I guess I should get changed," he mumbled.

"So, all this dressing as a girl is just about getting off is it?"

He looked at me not really understanding what I had asked.

"What I mean is it is just about sex. Do you think you can grow boobs just for a turn on? Once you have them you are stuck with them for life. They won't go down like an erection you know."

He gulped and looked at me.

"Mum, I told you I haven't really decided on that yet."

"I know that is why you are just going to change my underwear and stay like that. Just because you came off doesn't make any difference. It didn't to me when I was young."

His eyes opened wide and he shuffled a little.

"When I was young, before I met your father, I had group sex once. I sort of got off as the first guy fucked me. I couldn't stop the other 3 just because I had an orgasm. Even though I didn't want it, I knew they wouldn't let me go until they had their fun."

"Yeah, right, but what is that got to do with this, with me?"

"You are Veronica, and you are going to shoot at least twice more before I let you get changed."

"But, I'm quite happy with what happened just now. Do you really want me dressed like this all day?" he mumbled.

I put my hands on my hips.

"I spent ages doing you up. This way you will have an idea what it would be like to grow tits and not be able to get rid of them. Okay, I'll make it easier for you this time. Go and clean yourself up and then come to my bedroom."

I watched him shuffle away. This was part of my plan from the beginning, even though it meant I would jerk him off. I did sway one way then the other on this part, but with what he said about the boys and my next door neighbour, I just sort of got carried away. The main aim of this was to see just how much he was into this, and as I first suspected, I could see it was just about sex, and getting off. My main worry was that he wanted to go the whole way and change sex. I just hoped this would put him off, or make him realise dressing as a girl was as far as he wanted to go. When he came back to my bedroom he looked a little uneasy. For the first time this morning he looked more than a little uncomfortable with this. I'm not counting any chickens here, but I think my plan was on the right track. Hopefully he would be positively disgusted with my next move. I knew he obliviously liked wearing my worn underwear when he got excited, but now after he had come, he might find it a little too much to take.

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