Mike versus Michelle 2: Secret Sissy Summer

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This is a continuation of "Mike versus Michelle: I'm Not A Sissy". Mike who is Michelle in private tells us a little about his likes and dislikes. This is his first summer as a secret sissy.

Mike versus Michelle: Part 2

Secret Sissy Summer

By Sharon Parsons


 
I took the the things mom bought me from Victoria's Secret and put them in my dresser. I did as she suggested and locked my door at night. I was in heaven! Although I'd worn my mother's lingerie many times before, I never had the opportunity to go to sleep in a nightgown and wake up wearing it!

Of course I did more than just sleep in my sexy long nightgown! I pranced in it. I watched TV in it. And obviously I masturbated in it.

Oddly enough, I never masturbated to sexual thoughts. It was more than enough for me to fantasize about wearing pretty clothes in front of my mom and her friends. In my fantasies, I was one of them, even though I was still a boy, but they accepted me as a woman! Did they notice I was only 12? Wasn't it obvious that I was a boy? It didn't matter because it was my fantasy and it felt so good to touch my self through the silk as I pictured myself as one of them.

I had difficulty concentrating during the last two weeks of school. I had never been the best student in the world, so having another distraction didn't help. While I should have been listening to my teachers, I was instead daydreaming about being one of the girls. I was one of the girls in the teacher's lounge. I was one of the girls on the playground. My mind would alternate between being a 12 year old girl and being an adult woman.

I looked at the clothes the girls my age in school were wearing and compared them to my mom's clothes at home and the clothes my teachers wore. The younger clothes were cute, especially the dresses, but the pink tees and girl's jeans didn't do it for me. I liked the real dresses and women's pant suits that populated my mother's closet. I felt the same about purses. The girls in my school carried around little purses capable of holding not much more than a tube of lipstick and a compact. But my mother's purses and the ones my teachers slung across their shoulders were as big as houses. I imagined all the things I could carry if I had a big purse.

My friends were the other things that distracted me from my school work. They all had a case of summer fever. Our community pool had opened up and that's where we spent most of our nights after supper. On the weekends we'd play baseball. My two best friends in the whole world were Frank Rodrigues and Cam Holsteader. Frank lived in another neighborhood but it was close enough to ride my bike too. Cam lived two houses down and had a little brother who was Tony's age.

Given my drithers, I'd rather spend time at Cam's house than Frank's because Cam's mom was hot! Her name was Dana and she was good friends with my mom. Sometimes I thought about what it would be like to kiss Mrs. Holsteader, but when I did think about it, I'd feel guilty because of Mr. Holsteader. Mr. Holsteader was a nice guy. His name was Dave and he and my dad were pretty good friends. The Holsteaders had a second house in the mountains and we'd usually go up with them for a week every summer. Those were my favorite vacations because I got to hang out with Cam and I also got to look at his mom.

Getting back to my mom, she was really cool about the stuff from Victoria's Secret. She knew I was embarrassed about it so she tried not to bring it up. After the first week of summer, she bought me five more pairs of panties because I'd mess them up and she didn't like me sleeping in them when they were dirty. That was almost as embarrassing as having the panties in the first place, but she said she understood and told me not to worry about it.

That summer seemed to fly by. I was a boy by day and a girl in my bedroom. In some ways it was the best of both worlds. And the only two people who knew about both of my worlds were myself and my mom.

Mom did her best to include me whenever her friends came over. By include me, I mean she acknowledged my presence and tried to include me in the conversations. I loved hanging out with her friends- especially Cam's mom, Mrs. Holsteader. But usually if Mrs. Holsteader came over, Cam came with her, so I'd have to break away from the ladies and hang with my friend.

I learned a lot about women by spending time around my mom and her friends. I loved the way they talked with their high pitch voices. They were always moving their hands around, especially while they were smoking. Sometimes I'd hold a pencil between my fingers and try to move my hand around like they did. It made me feel so feminine when I copied them.

My little brother and my father had gotten their hair cut twice before school started back in the fall. My dad badgered me about getting mine cut, but I always found a way to put it off. By the time I entered eight grade in the fall, my hair was touching my shoulders. I loved it.

My friends who hadn't seen me over the summer gave me a little crap about my hair being so long at first. But eventually they got used to it. Dad didn't. He was bothering me about it at least once a week. Mom tried to defend me and my hair by saying a lot of boys were wearing it long. Dad wouldn't give in though until I promised to at least get it trimmed. Mom told him that she'd take me to the place where she gets her hair cut. Dad laughed and said I deserved it to get my hair cut in a beauty parlor.

That was a weird moment for me. I felt bad about my dad laughing at me. The way he said "beauty parlor" was bad enough, but I knew he was thinking sissy parlor when he said it. He knew it and I knew it. Tony laughed too, but I think he was just laughing because our dad was.

I felt bad about my dad laughing at me but I was relieved that I'd get to keep my hair long. And you better believe I was excited by the idea of getting my hair cut in a beauty parlor. So like I said, it was a weird moment for me, but not as weird as actually sitting in the chair next to my mom as two women did our hair.

Not surprisingly, I was the only boy in the salon, although there was one girl there who was about my age, except a little older like fifteen or sixteen. Everyone else in the store was older, like my mother's age. I stuck out like a sore thumb.

Mom told me not to worry about it and asked me if I wasn't just the tiniest bit excited about getting my hair done in a beauty salon.

I was excited but I was also worried. I told her I was afraid they'd make me look like a woman.

She told me not to worry because she'd be right there with me. She assured me that I'd still look like a boy when I was done. She told me it would be fun.

Mom was right about the fun, but she was a little off on the manly forecast. To be fair, some of it was my own fault. The lady who did my hair asked if she could shape my eyebrows a little. I hesitated and turned to my mom for advice. She said a little wouldn't hurt, so I went with her suggestion.

In the end, I thought it was a bit much but my mother assured me that probably no one else would notice the slight feminine arch. Yes, I was worried that my friends would notice but I was also silently delighted with the look!

I have to admit that I loved the entire experience! Going to a beauty salon was nothing like going to Pete the barber. I loved getting getting a shampoo and the manicure felt wonderful on my hands. They didn't use nail polish or anything like that on me, but it felt nice- like a hand massage.

I walked out of the salon with a nice looking haircut. It was still long, hanging close to my shoulders, but it was neat and styled. I didn't look like a girl, but I knew that I could if I tried.

Mom told me that I looked terrific and asked if I liked it. I loved it but I wouldn't say so. I told her it was alright but I thanked her for taking me. I told her I liked the hand massage. I felt kind of guilty about not showing my excitement, but that's what I meant about not wanting her to think of me as a sissy.

I understood there was something different about me. No other boy in his right mind would allow his mother to take him to a beauty salon, much less wear pretty little panties and nightgowns to bed.

My attraction to womanly clothes and feminine things was beyond the scope of my understanding. I just knew that I liked it. I loved it and wanted more of it.

I don't think at that point in my life I ever really wanted to be a woman for real or for keeps. For me it was about being "like" a woman and "like" my mom. Its safe to say I idolized her the way most boys idolize their fathers. She was and is my role model.

Mom needed a cigarette after we finished with the salon, so we went to the food court. It was only 11:00, too early for lunch, so she got us a couple Diet Cokes and we sat at a table so mom could smoke.

I had just turned 13 and was still a year away from smoking my first cigarette, but I thought about it often. I identified smoking as being a feminine habit, even though I knew that just as many men as women smoked. Maybe it was because I grew up with a mom that smoked and a dad that didn't. Regardless, I couldn't imagine seeing my dad with a cigarette and at the same time, I couldn't imagine my mother without one. It just looked right on her.

After she finished her cigarette, mom announced that she'd like to do a little shopping before we went home. We got up from our table and I followed her out of the food court and into Macy's.

School was just a couple of weeks away from starting, so it made sense that I would need some new pants and shirts. We also looked for some that would fit Tony while we were there.

We were spending all of our time in the boy's department and there's nothing remotely feminine about the boy's department. I say this because I want you to know that buying something feminine for myself was the last thing on my mind. Yes, I'd gotten a nice hair cut and even had my eyebrows shaped a little, but it wasn't really that noticeable. I knew I'd get away with it when I went back to school.

My dressing up had always been a private thing. The only time I'd ever let my mother see me dressed was by accident and I had no intentions of ever dressing as a girl in public. That's why the nightgowns, and the bras, and the panties had always been enough for me. Those aren't the kinds of things you wear in public, even if you are a girl, which I certainly wasn't.

We were leaving Macy's with our bags full of boy's clothes when my mother stopped in front of the junior miss department.

My heart immediately went into palpitation mode. I knew darn well thatl my mother didn't have a reason to stop in front of the junior miss department unless...

"I was thinking we could look around a little since we're already here," said my mother.

"Not for me," I said sternly.

"Yes for you," said my mother in her melodious tone that seemed to mock and reassure me at the same time.

"What for? Its not like I go outside when I do what I do. What's the use of paying for something I'm just going to wear in my room?"

"So you're saying that if we buy you something, you'll at least wear it in your room?"

"No. I'm just saying its a waste of money and I don't need anything else."

"Like you didn't need your hair trimmed today?"

"Well I didn't need it. The only reason I did it was because Dad said I had to get it cut."

"But you could have gone to a regular barber like your father does but you didn't."

"Thats because it was your idea to go to the salon."

"And I was right," said my mother. "A barber would have chopped up your hair and since you want to wear it long, I knew best about what would work for you. Just like I know now that you're going to kick yourself if you don't let me help you pick something out. What about this top," she said as she picked a white flowing hippie type shirt from a rack. The label on the collar said it was made by a company called Miss Chievious. "I think this would look nice on you if you had a pair of jeans to go along with it."

"I already have jeans," I said defensively.

"But not like these," she said as she pulled a pair of Baby Phats from another rack while draping the top across her shoulders. "They both look to be about your size, but it would probably be best if you tried them on here so we don't have to take them back."

"I can't change my clothes here," I said adamantly. "This is a girl's store and I'm a boy."

"I hate to break it to you Michael, but with that new haircut and your eyebrows arched, you could pass for a girl if you tried these on."

"What!" I shouted as I looked at a floor length mirror mounted on a column. "You said it it didn't look bad. My friends will kill me if they find out."

"Relax honey. It doesn't look bad and no one can tell by looking at you in the clothes you have on now. What I'm trying to say is that you look kind of ambiguous with your hair long. If you dress like a boy, then people will see a boy. And if you dress like a girl..."

I completed my mother's sentence. "Then people will think I'm a girl?"

Mom smiled at me. "Yes honey. That's what I'm saying. But isn't that what you want? You know, to have it both ways, to see what its like."

"Well yeah. Kind of. But I didn't want to do it for every one to see. Its supposed to be secret. I could get in a lot of trouble if anyone ever found out."

Mom started to look cross and it was clear to me that her patience was wearing thin. "I'm not trying to make you do anything that you don't want to do. I'm not pushing this on you and just so you know, you're certainly not doing this for me. So if that's what you're thinking, then maybe we should forget about the whole thing and just leave. As a matter of fact, if you want, we can stop by the barber on the way home and fix what they did in the salon."

It was then that it dawned on me that my mother was right about kicking myself if left the mall without something like a dress. A dress? Why not the top and jeans that my mom was holding? Because thats not what I like, I thought. I don't want to look like a teenage girl. Mom doesn't wear stuff like that. I want to look like her! I looked at the simple but stylish blue dress she was wearing.

I don't know how much time ticked off the clock while I was preparing my answer but I know I did a lot of thinking, and I though fast- maybe too fast.

What do I have to lose by saying yes, I wondered? Mom knows I like women's clothes. But if I'm going to do it, I don't want to look like a girl from my school. I want to look older and more mature.

I looked at the top and jeans my mom was carrying. They were definitely feminine. I mean no one was going to mistake them for boy's clothes. All I have to say is yes and they're mine. I won't even have to try them on here if I put up a fight.

And then I stumbled on my pride. Just how much of a sissy do I want my mother to think I am? Was it really worth it? I mean I didn't even like the clothes she was holding- not really.

"I don't think so Mom. Lets just go home," I said.

"Does that mean you want to stop by the barber too?"

"No," I whined. "Lets just go."

Mom looked disappointed as she hung the top and jeans back on their racks.

We walked the next fifty feet or so in silence with me kicking my self in the butt as we got closer and closer to the exit. And that's when I saw the skirt and blouse in the Anne Klein section. The skirt was long and flowing and printed with red and yellow flowers. The top was just white and the mannequin wearing it looked so elegant and classy. It was something my mom would wear. I summoned up my courage and stopped in front of the mannequin.

"Its very pretty," said my mother knowingly. "You have good taste. But don't you think its a little old for you. It looks like something I would wear."

My face felt like it was burning so I looked at the floor to hide my shame while shuffling my feet. "I know that Mom. Thats why I like it."

Mom nodded her acknowledgement of my words as she placed a finger to her chin in thought. "I still think its a little old for you. As a matter of fact, I think its very old for you, but if this is what you like, then I suppose it would be less expensive and more private to look through my closet."

"Really? But I thought you said I was too big and that I stretched your clothes."

Mom shook her no. "I just said that because I thought it best that you have your own things. I still do, so whatever you like, if its something I'm willing to part with, we'll call it yours."

"Really?" I didn't know what else to say. I was stunned, not so much that my mom would offer to let me have some of her clothes but because for the first time since she caught me, I was honest about what I wanted, even though I hadn't really explained it to either of us.

"Yes Michelle. I do mean it. If that's what you really want then you're not asking for much. But if you don't mind, I'd still like to buy you the top and the jeans."

I started to argue with her but thought better of it. "Okay Mom. We've got a deal."

"Then its done, but we'll still need to get you some shoes."

"But why? Its not like I'm going to go out or anything."

"Trust me honey. You'll feel better about yourself in a pair of shoes that fits, even if you never leave your room."

********

Dad and Tony were in the front yard playing catch when Mom and I pulled up the driveway. Tony asked us what was in the bags and Dad asked me when I was going to get a hair cut.

"He already did," said my mother as she ran her fingers through my shoulder length hair. "Beth just trimmed off the split ends and gave it a little body. I think it looks nice."

Dad shook his head and threw the ball to Tony who dropped it. He was focused more on what mom and I had in the bags than he was on his game of catch.

"Did you get me anything," asked Tony?

"Just some clothes for school," said Mom. "I got you both some new pants and shirts. You can try them on after dinner."

"Aw mom! Do I have to?" he whined.

Mom told him she wouldn't have said it if she hadn't meant it. She turned and walked inside the house with me following in pursuit. The last thing I wanted was for Tony or Dad to get a look inside my bag.

She described some of the clothes she thought I might like as I followed her up the stairs to her room. "I have some extra purses you might like too. Do you like dresses or pantsuits?"

"Both," I said shyly.

"Well I wish we had the time and privacy for you to try them on, but I'm pretty sure they'll fit." She looked at my flat chest. "But you'll definitely have to fill that bra of yours with some socks or something. I know, maybe I can look into getting you something more realistic than socks."

"What do you mean?"

"You know. Breast forms. They're made from the same material they use in breast implants."

I couldn't hide my excitement. The idea of having real looking breasts was titillating. "Would I be able to sleep in them," I asked?

"I suppose so. As long as you take them off before you go to school."

I laughed at her joke. "I don't think I'd forget something like that."

"Probably not," said my mother as she opened the door to her walk-in closet.


 

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Comments

Who Will Win?

littlerocksilver's picture

I am rooting for Michelle. Go girl! :) Portia

Portia

MIKE VS MICHELLE 2

IT IS GETTING BETTER ... DRAWING ME IN LIKE A LURE ON THE END OF A FISHING LINE ... THANKS FOR THIS WONDERFUL GIFT >>>

LOVE YOUR STORIES and ALL OF YOU ... THANKS FOR THIS WONDERFUL GIFT >>>

WUNDEBAR

I have really enjoyed the first two installments of this story. Please continue with this wonderful tale.
'Sika

Mom is having more fun then Mike

RAMI

I think mom is having more fun with this then Mike and is happy to have her daughter Michelle to shop and do things with. Will mom push Michael further down the road to Michelle, then he ever intended? I think mom has Michelle's life prepared for her.

RAMI

RAMI

Thanks for Continuing

I was hoping that you would do more with this story. I'm enjoying it.

Moms always like to have a

Moms always like to have a daughter that they share things with, someone they can shop with, watch girlie films,talk about makeup, All the sort of stuff you can't do with a son.

It seems to me that with Michelle's mom talking about buying shoes that the shopping trip with her new daughter is on the agenda very soon,

Love the story, And like the way that Michelle is coming to terms with what her heart desires most of all, Thanks for posting it.

Kirri

I agree with Kirri about

nikkiparksy's picture

I agree with Kirri about maybe her mother's desire's Looking foward too the next chapter as this is turning out very good :).

Nice Mum!

I'm pretty sure that a lot of people reading these two chapters are thinking "What a lovely Mum!"

Briar

Briar

I find it rather interesting

I find it rather interesting that Mike has not caused a fuss being called Michelle by his Mother. She has used that name to him several different times and he just lets it "wing" right by him. This gives me a belief that Mike would really and actually wants to Michelle regardless of what he is saying to his Mother about being caught as Michelle. J-Lynn

Michelle Is Here To Stay

How long until only Michelle is here is up in the air.

    Stanman
May Your Light Forever Shine
    Stanman
May Your Light Forever Shine

Michael is being given a long rope

Sharon
Are you writing under another name.

Mom has given Michael a long rope, but she is quiet intentionally seeking to rope in Michelle.

Jessie C

Jessica E. Connors

Jessica Connors