Summer to Remember

My Friend's Older Sister

Growing up in a family of all boys meant, quite simply, that there was no older sister. Even worse, there were no sisters at all. In my family, there weren't even any older female cousins that I ever saw that much either. So, except for my mom's white lingerie, my only exposure to any exciting intimate clothing was from sneaking around my various friends' houses and trying on their sisters' stuff.

And that's where this story begins. One of my best friends, Michael, had this amazing older sister, Linda, who was tall and pretty. She was just a couple of years older than me, had dropped out of college and was living at home with her family. She wasn't very bright but she did dress extremely well. She was your classic party girl.

She always carried that "older sister" attitude and she acted like she was just plain fantastic. Linda treated everyone else like a jerk. As I look back, I now realize that growing up, slightly older people did that...a lot.

And like in many households, Linda hung her lingerie in the bathroom to dry after washing them. I can still remember that one day, as a late teen, using their bathroom one day and seeing her matching powder blue bra and panties hanging up for the first time.

Blue? I never even knew they came in blue. I had seen black ones in catalogs, but blue? Never. And these panties had this cute, tiny pink rose on the front waistband. I can still see them as if they were yesterday.

Knowing that I did not have a lot of time I took off my clothes and slipped on her panties. I got a huge erection within seconds. These were wonderful.

I then fumbled with the bra...and finally got it hooked in back. What a pain that was! But the shock of seeing myself dressed in something other than my mom's white bra and panties, was a feeling that was almost overwhelming.

I was hooked and I loved it!

While admiring myself in the mirror, my hands were trembling and I felt funny in my stomach...not a sick feeling...but maybe one of butterflies. For this moment in time I could pretend I was this beautiful older girl.

I watched myself as I ran my hands all over the bra and felt my nipples get hard and my cock get even harder. I loved this feeling.

Girls were so lucky to be able to wear these every day! The more I pretended to be her, the more excited I got.

Carefully, I removed my cock from the panties and began to slowly masturbate into the bathroom sink. Oh, if I could only be Linda for the day. I loved pretending I was her.

This was amazing. My legs could barely support me and my pulse was now racing. I then exploded all over the sink and closed my eyes as the final drop came out. Nothing had ever been this good. Linda's clothes were the best!

With each visit to my friend's house, I would visit that bathroom. Sometimes just even walking into that bathroom and seeing any of her clothes hanging there, would give me a hard-on. Never knowing what I would find on my next trip made it even more exciting. She had matching black bras and panties, some thongs, cute babydoll nighties...and they were all for the taking. It was my little playground.

I vividly remember the times I slept over his house and I would go into the bathroom several times in the evening, quickly change into her clothes, pull out my raging cock, jerk off, and go back to bed. How I could cum that many times in an evening was beyond me, but it was all I could think about. I loved her clothes. She was the favorite of all my friends' sisters.

And if I could ever put together a whole outfit in there...that was the jackpot. Sometimes there was a pair of her jeans, or a skirt with a top lying about in the bathroom. Putting them all on starting with the bra and panties was my dream come true.

I got real good at stuffing the bra with small wash cloths to give myself little boobs. And I was always extra careful to put everything back exactly where I found them and never once were there ever any questions raised.

But over time I got either careless or maybe just more daring. I was over his house late one afternoon and I was in the bathroom...again. I had just changed into Linda's light blue bra and panties (my absolute favorites) stuffed the bra a bit and then slid on one of her tops and skirts. Oh, I loved this look! I was pretending to be her going out for an evening.

I had only been in the bathroom playing for about 10 minutes and checking myself out in the mirror when I heard a knock on the door.

"Are you going to be out soon, I need to use the bathroom," It was Linda. Apparently she had just come home and needed to get in the bathroom. Her room was right done the hall.

"I'll be right out. Just a couple more minutes" I replied...trembling. I knew my nervousness showed in my voice.

A minute passed and she knocked again. I only had time to remove her top and skirt, and was trying to fold them up like they were when I heard the child safety lock pin pop the door open.

There I was, standing in her bra and panties with her skirt in my hands.

"I thought so, you pervert. I knew someone was wearing my lingerie and now I know who."

Bam, she had her cell phone out and took pictures of me in rapid fire as I tried to cover up.

"You weasel, put the skirt and top back on and pose for me or I'll go over your house right now and show these pictures to your mom." Trembling I did exactly as she said and she took several more pictures of me. I was so scared.

She then said to me sternly, "Now change out of my clothes right now." She closed the door and left.

And that was it.

For another hour I hung out with my friend downstairs in the basement where we were playing pool. He knew nothing about what just transpired upstairs, and then I left. I was scared to death of what Linda was going to do with the pictures.

My whole week was a wreck. I kept thinking she would tell my mom. Every time the phone rang, or every time my mom said my name, I was expecting some kind of confrontation. But nothing...it was torture.

It wasn't until that Friday night that my mom asked me if anything I should know happened over Michael's house last weekend. She had gotten a call from Linda who asked if I could come over on Saturday to help her out with some projects.

Mom said it was a strange request, but I said, "Nothing out of the usual."

Mom said, "She said you would know what she meant so be there promptly at 9AM."

I barely slept that night. In the morning I was up and started the walk over to my friend's house. When I knocked on the door, Linda was there to meet me and said, "Well, I see my little slave girl arrived right on time." She held the door open for me and I walked in. I had no idea what to expect, but I didn't like the sound of slave girl and now I dreaded the idea of being there.

She walked me into the living room and lying out of the sofa was a white cotton bra and panties with a blue and simple plaid sundress.

Sternly she said, "My family is away for the day and won't be back until tonight. My mom said that because I was out too late the other night, I have to clean all three bathrooms today as punishment."

She continued, "There is no way I'm doing that, but you are. Since you want to be a girl so badly and secretly wear my clothes in the bathroom, then you might as well be useful and clean in them."

She pointed to the clothes and said, "Go put these on and meet me in the kitchen."

As I looked more closely at the white cotton bra and panties, I was so bummed out. I actually liked the idea of being dressed, but in cotton? My mom had better stuff than this. And the plaid sundress was anything but sexy.

As I slowly changed, I didn't even get excited. I folded my clothes on the sofa and met her in the kitchen. "Well, my little maid looks quite stunning in that outfit. Here are your tools for the day."

In a plastic bucket she had all the cleaning supplies, including tile cleaner, mold remover, window cleaner, rags, even a tooth brush for cracks and crevasses. Everything.

"There are three bathrooms to clean so let's begin with the one you like to play in the most. Do you like to clean? Well, do you? Speak up."

"Yes Linda," I murmured.

"And today, you will call me Mistress because I am the mistress of the house...understood?"

"Yes Mistress,"

"Say it again and mean it."

"Yes Mistress," I said louder.

"That's better."

She led me to the first bath and instructed me on how well she wanted it cleaned, and then said she would be checking in on me all day, so no funny stuff.

I really tried my best to clean the tiles, but they were gross with mildew stuck in the grout and that took much longer to clean.

Linda came back after I thought I was done. Looking around she pointed out all the areas that needed to be done better and I started all over again. She stood there watching and even took pictures of me kneeling down scrubbing out the toilet.

She checked again on me a bit later and said it was better, but I still had streaks here and there. After the third time she finally gave her approval and now one bathroom was done. What a pain. This one took well over an hour.

Whatever minor thrill I had about wearing her bra, panties and dress was over long ago. When I thought about all the great clothes she had and what I was stuck wearing, this sucked. I tried to make the most of it, but could not muster much of a fantasy.

The next bath was downstairs but had no shower or tub so it went better overall. "So, my little maid is getting the hang of it, is she?"

"Yes Mistress," I replied.

Her parent's master bath was much bigger but was in better shape overall. Plus, I had a better idea of what to do. I was now enjoying seeing myself in their large mirrors and tried to be as feminine as possible. Maybe this wasn't that bad after all if I just changed my attitude.

At noontime I was done. I found Linda in her room and politely knocked. "Would you like to inspect the last bathroom Mistress?"

"Yes, and it better be the best one." As we walked in she examined everything and said, "You did well my little maid."

"Now, let me ask you. Did you get excited wearing my white cotton bra and panties?"

"No Mistress, I did not."

"And why do you suppose that was?

"Maybe because they are not as exciting as some of the other bras and panties I have seen of yours?

"Seen or worn?"

"Maybe both."

"I see. Do you have any favorites?"

"I've always liked the powder blue ones. They fit the best and I like the color and feel of them."

She paused for a minute and said,

"I thought so. The ones I caught you in. Come here for a minute."

I walked over with my head down and hands folded in front of me. She reached behind her and handed me the light blue bra and panties.

"Please go into the bathroom and change, and then return. Place the clothes you were wearing in the hamper."

"Yes Mistress."

Finally I was taking these boring clothes off and slipping on her soft bra and panties. These felt so good on and finally I got a little excited, but not much. I was too nervous.

When I walked back into her room, I was a bit embarrassed and walked in with my head down.

"Do not slouch when you are wearing my clothes," she barked. "Stand up straight with your shoulders back. And don't stand with your legs apart. You look like an old man."

I did exactly as I was told and then she said, "Now, look at yourself in the mirror." Seeing myself in a full length mirror head to toe in her pretty bra and panties was awesome.

"Now, let me see that little cock of yours."

I looked at her in disbelief. "I said, let me see that little cock."

I was so nervous it actually was little. It was as if it shrunk when hearing her voice.

"No wonder you want to be a girl. If I had a cock that small I would too. Can't you make it any bigger?"

"No Mistress, I'm too nervous right now."

Linda picked up some hand lotion, placed it on her hand and told me to come over to her. She then reached over and lightly touched my penis underneath the panties with her warm hand and lotion. "Does this help my little maid?"

Instantly my cock sprang to life. "Oh, so you can be a big girl."

She stood back and looked at me. "I think you need some lipstick."

Standing there with a hard-on as she was applying red lipstick was getting me even more excited. I loved the soft feel of the creamy lipstick on my lips.

"There. Now you look like the slut you really are." She then placed a towel on the floor in front on me and the mirror.

"Now, my little maid, cum for me."

I tried my best to focus on my image in the mirror. I had to block her out of my mind and just see me. Stroking my cock with the soft lotion on it made it easier and I could feel myself getting closer and closer to the magic point.

I forgot all about Linda being in the room. I slid my other hand up under the bra and began squeezing my nipples.

"Now cum for your mistress, my little maid."

And with that I exploded all over the towel.

"Well that didn't take very long," she said almost disgustedly, "Is that all you could do after wearing my clothes all day long? You are pathetic."

I was so embarrassed I felt like crying.

"Now, go wash up and meet me downstairs. And keep the bra and panties on when you come down."

When I finally got downstairs, I still had on her light blue bra and panties as she asked. I stood there in front of her just wondering had I had to do next.

She passed me my clothes and on top were three pair of panties, black, red and flowered. I looked at her with this look and she said,

"This is your reward for the day. You were the perfect maid and I want to make sure my maid thinks about me every day when she is not with me. Please put the black pair on right now and wear these every day. No more boy panties for you. If I ever see you over here without them on, you will be punished. Understood?"

"Yes Mistress."

"Now, please put my blue bra and panties in the hamper as you change."

Sure enough, my own underpants were not to be found in my stack of clothes, and I really did like her panties she gave me. It was the only positive of the day.

As I was about to leave she said,

"And remember, you only call me mistress when we are together like this, otherwise it's Linda."

"Yes Mistress. What about the pictures? Are you going to show my parents?"

"I still have not decided. And there may be other times I need to call on my maid."

++++++++++++++++++++++++

It only took a few days for my embarrassment to fade away and I started wearing Linda's panties in secret. Despite my humiliating time with her, I got aroused even thinking about the wearing the panties she gave me to take home. My time in my own bathroom increased as I just had to watch myself as I jerked off almost every day in them. This reward thing was good.

About a week later my friend Michael called and asked me if we wanted to get together on Friday. His family was having a cookout and some of his cousins were coming over. It could be fun. But his place was the last place I wanted to go with his sister Linda around.

He finally talked me into it and I decided I better wear Linda's panties in case she checked me out. But with my luck, the guys would give me a wedgie and find out I was wearing her panties. I was in a no win situation, but I decided on the black pair.

The cookout was actually terrific except for the fact that Linda showed up there later with several of her stupid friends. I tried to avoid them but it was hard since we were there for several hours. I could tell by the way they were looking at me and giggling that Linda had shared with them what had transpired.

Once when I went inside, Linda followed me in. There was no one inside but us. With her arms folded she said, "Drop your pants my little slave."

I looked at her like, "Really? Right here?"

"Yes. Right here and now, or everyone will know about you."

As I did, I knew she was pleased that I was wearing her black panties as she nodded her head up and down. "I see you remembered. Good, my little slave girl." In my mind there was nothing good about this. It was like she owned me.

"Let me see your poor excuse for a cock."

I looked over my shoulder, saw it was safe, and quickly slid my cock out of the panties. "Still little I see...put it back before someone else comes in and sees it and starts laughing." With that she walked out back to the party.

The late afternoon turned into early evening and then one of her friends, a tall cute redhead came over while I was alone and said, "Hi Alex, I heard you clean a mean bathroom."

I instantly turned as red as her hair and did not know what to say. She then quietly said, "It's OK, I think it's cute...and sexy."

I was still embarrassed and tried to look away..."Aww...you're bashful too."

About an hour later she returned and said, "Linda says you still owe her big time. So, I could use some help over at my place tomorrow. I have my own apartment and it needs a good cleaning. What would be a good time for you to come over?"

I was stammering out, "I'm not sure I can," when Linda walked up with her cell phone..."Should I show your friends these pictures?"

"I can be there at 10AM."

"Great, here's my address and my name is Samantha."

Some party. I was a wreck. I dreaded the next day, thinking that my whole life is ruined. I slept in as late as I could, showered, and slid on Linda's flowered panties, just in case. That actually helped and surprisingly settled my nerves. I took my car over to Samantha's place and when I got to the second floor of the apartment building, I quietly knocked.

I could hear movement inside and then the door slowly opened. Samantha was wearing a black corset top with hip hugging jeans and heels. She looked spectacular, especially compared to her casual look of last night's cookout.

"Please, come on in," she said in a cheery voice.

I entered slowly, not knowing what surprise she may have had around the corner, but what I found was a real nice apartment.

"Wow, your place is really nice."

"Thank you, I love it too. I'm glad you could make it."

She gave me a brief tour and nicely told me all the things she wanted me to do as her maid for the day. There were kitchen duties, bathroom duties and laundry.

"Now, please take off all your clothes right down to your panties."

"Right here?"

"Yes, right here." She sat down right in front of me. Great, here we go again.

I slowly removed my shirt and then lowered my pants, exposing the flowered panties with the cute lace waistband Linda gave me. "Oh, I love those...where did you buy them?"

"Actually Linda gave them to me as a thank you for doing a good job last week. She instructed me to wear these and two other pair every day or I would be punished."

"Well, today you are mine so please take them off and put these on." She placed a pink lacy bra and a matching pair of pink panties on the edge of the sofa and continued to watch.

These were real nice. I carefully removed the flowered panties and then slid on the pink ones. They were so soft, but I was so nervous standing naked that my penis just stayed there...small and limp. She never said a word.

I then adjusted the bra straps a bit and started to put on the bra.

As I reached behind myself to attach it, Samantha said, "I'm impressed. You did that with such ease. Did Linda teach you that?"

"Not really. I learned by myself. But I would practice when I would wear her clothes."

"I see. Then you look like you've had a lot of practice." That got me a little embarrassed.

I was now standing in front of her in just her bra and panties, which was better than being naked. After standing up and walking around me, and looking me up and down, she asked me to sit. I tried to be as ladylike as possible and folded my hands.