My Summer Penance

by Karen's Wife

 

My name is Terry Sean O'Neil. Let me start at the beginning. It was May 9th, and my 18 year old sister Gale was preparing for college in the fall. A little early I thought, but Gale always had things in order long before they had to be. She was going to be working the summer at a resort as a barmaid-waitress. I told her she was better than the people who worked those kind of jobs, you know, the dropouts. Gale told me the resort was an expensive resort that catered to the wealthy. Waitresses received big tips, and she said that she would make enough money in the summer to last her through spring. This would help her study, as she wouldn't have to work. "Besides" she said, "if Sherry's parents weren't part owners, I'd never stand a chance of getting hired at all. All my expenses will be paid, and the uniforms are included."

This got me thinking about how I had nothing to do this summer, being 16 meant that there wasn't a lot of jobs available. I came up with a plan to get hired at the resort along with Gale. I thought that they must need a boat boy, pool boy, or even someone to cut grass. Maybe I could wash and detail cars for those uppity people, there has to be something I could do. The only thing was that I needed to come up with something that would make them WANT TO hire me instead of anyone else. Then it dawned on me, I just had to get something embarrassing on Sherry, and agree not to tell anyone if I was hired. But what could I get?

The next day I came down to breakfast and Gale and Mom were talking. I came in to the kitchen in the middle of the conversation. I heard that Sherry was going to bring over their uniforms after school, and she and Gale were going to try them on in Gale's room. Gale said that Sherry was going to give her some "pointers" on how to assure big tips. Mom gave a HUMPH and shot a look at Gale. Gale looked back and said, "Oh mommy, I'm a big girl now, and I won't do anything naughty. We're just going to practice swish walking and acting blonde." This might be interesting I thought, and I excused myself saying I forgot a book in my room. I flew up the stairs to my room and got out my little cigar cam I had bought last year. My friend Mike and I were going to put it in the girl's locker room, but after I bought it, I found out the range was only 10 feet. I snuck into Gale's room and placed it under a stuffed animal she had placed on a shelf. I went back to my room and turned on my TV. Rats, the view was too high. I had to sneak back into Gale's room and adjust it. I stuck a pencil under the rear of the camera, and went back to my room. Gale was yelling for me to get my ass down to the car or walk to school. I turned off the TV and cam, and went downstairs.

I was wired all day at school. I had to get into Gale's room when we got home, to turn the cam on.

I also had to load a tape in my VCR so that I had something to trade for the job. The ride home with Gale was kind of quite. The radio wasn't on that loud, but it looked like she was day dreaming about the summer. Maybe she was dreaming about meeting some rich single guy there who would carry her away. Anyway, I had to act fast when we got home. I asked Gale to let me out of the car before she parked. I told her that I needed to get to the bathroom fast. As soon as she stopped the car, I was out the door. I ran up the stairs and into Gale's room and turned the cam on. Then I ran into the bathroom. I stayed in the bathroom for 5 minutes, then I came out and thanked Gale. She looked at me and giggled. I went into my room and set up the VCR, it was all set to record when I wanted. The signal from Gale's room was perfect, and I was getting excited, a little too excited. I decided to go outside for awhile.

Sherry came over to our house at 3:45, carrying some uniforms that looked like short maid 'dresses The dresses were bright red. After the two of them went up to Gale's room, I went to mine. The first thing I did was to hit the button on the VCR to start the recording. I looked at the screen, and couldn't believe it. Both Sherry and Gale were taking off all of their clothes. I felt bad watching my sister strip, but Sherry must have had 38DDs, and my eyes were on her. They then put on low cut red bras, and shiny panties. Next came reddish colored stockings. The stockings looked like nylons, but only went a little ways past their knees. Then they had red shoes. They weren't high heels, but they did have a small heel, and a strap. The dresses turned out to be ruffled with a rear zip and wide shoulder straps. The straps almost looked like sleeves at the top, going out over the shoulders. The front of the dress was low cut, showing the girls' cleavage. The back was not cut low at all. The dresses covered the tops of their stockings, and seemed to flare out from their waists. They looked hot. Then Sherry started to show Gale how to swish her ass and flirt. I couldn't watch anymore. I had to clear my head and settle down, so I asked Mom for the car keys so I could go to Mike's house for a few minutes.

"Be sure you're home in 90 minutes. You're father will be home from his trip, and I'm sure he just wants to eat supper and go to bed." Mom said as she threw me the keys to her car.

"Yeah, I'll be back on time. I know how easy he gets upset after a trip." I answered.

I went to Mike's house and told him of my plan. He didn't think it was a good idea saying," You know how girls are. They tell each other everything. Do something to one of them, and they'll all know about it. They'll get you somehow. I don't even want to see the tape. I'd beat the crap out of anyone who did that to Becky."

"Hey, don't you remember the girl's locker room idea? You wanted in on that one. And that was going to get a lot of girls on tape" I reminded him.

"I was younger and dumber then. Besides that, I got it going with Becky now. I don't want to talk about this anymore Terry, if Becky finds out I knew you were doing this, I could get in trouble with her" said Mike.

It was time to go home and see Dad. He's was only gone three days this time, but he still likes to be brought up to date with the family. When I got home, the table was set, Dad was having a drink before supper, and Gale had changed into a turtleneck and capris. Sherry was not there, so I assumed the lesson was over. Then I thought about the tape. I went to my room, and the VCR had shut off. It had ran out of tape and went to auto rewind, and off. I took the tape out of the VCR, and put it under my bed so that I could watch it that night. I went down for dinner, and everything was fine. Dad told some off color jokes that Mom and Gale didn't like, but hey, that's what men do.

When supper was over, Gale helped Mom clear the table and do the dishes. I sat and talked to Dad in the Living room. He asked if I had any plans for the summer yet. I told him that I was working on making some money this summer, but that I wasn't sure on a few things that I needed to do first. I told him, "As a matter of fact, I was doing some research today. So far I only got to go over a little bit of it, by I plan on spending time tonight going over the rest. I better get going now."

I went to my room and locked the door, put the tape in and hit play. There were Gale and Sherry again taking off their clothes. I watched everything again, right up to where I had left. I loved watching Sherry pretend to be a dumb blonde. She looked even hotter when she pretended. I was getting horny watching. Then I heard the doorbell ring, but my sister yelled that she would get it. Man, this was one hot tape. With a little editing, I would get a job for sure. Then something went wrong. Gale wanted to show Sherry how to seductively use an order pencil. Gale said, "I keep a pencil hidden up on my shelf there by the stuffed animals. I used to pretend that they would write to me when I slept".

"Next thing I see is a large image of Sherry's head on the screen, and I hear, "Ah, Gale. Could you come here for a sec. I hope this isn't what I think it is on top of the pencil."

Then I saw Gale's head and heard. " That little ass hole is mine now. Terry will never see 17, let alone summer. MOM! Can you come here? It's an emergency."

"What's wrong??" my Mom said as she flew into the room, "is someone hurt?"

Gale replied, "Not yet. But I'm going to beat the crap out of Terry when he comes home. Look at this. I think it's a video camera and he's been taping Sherry and I changing."

"Your father will be home soon, dear. We'll let him handle this. You know how protective of you he is, I wouldn't want to be in Terry's shoes" Mom said.

Then there was nothing but a picture of Gale's room on the screen. I stared at it for 1/2 an hour wondering what I should do. Oh MY God!! Dad walks into Gale's room, steps up to the camera and says, " Well Terry, Gale and her parents should be here by the time you see this. I expect you to bring anything you taped, down with you. NOW!"

Shit! Caught. I had to think fast. Dad's real hard to fool, and I can't lie to him. I pulled out the tape and went down to face the music. Everyone was sitting in the Living room. All the chairs were taken, and I had no place to sit. Dad ushered me to the middle of the room, and told me to stand there and answer the questions they had.

Dad," Did you know that you would be taping Gale and Sherry when they would be changing?"

Me, " Not really, I just wanted to find out if there were more jobs at the resort."

Gale, "You mean you didn't hear me tell Mom yesterday that Sherry and I were going to try the uniforms on after school today, in my room?"

Me, "Well, maybe I heard something about the room, but I didn't know you would be changing."

Dad, " What was the purpose of the tape Terry?

Me, " Believe me, I was just looking for information on a job at the resort. That's it. I'm very sorry if I hurt anybody."

Dad, "Well, leave the tape so that us adults can talk about what we should do about this. It's very serious, and illegal. Gale has every right to call the police if she wants, and so does your sister. On your knees and ask each of them for their forgiveness. "

I started to tear up, I was so humiliated, but I did it. I couldn't look them in the eye as I said to each of them, " Oh please forgive me for what I have done to you. Please, please, please. I'll never do anything like this again. Please." They both snickered and pushed me away with their feet, saying nothing.

Just then the phone rang. Dad got up to answer it telling me, "Go to your room until I call you."

I went to my room, my stomach was full of knots. I was restless. I think it went quite well with dad. Everything I said seemed reasonable, but Dad always saw through these things. I heard the doorbell again. God, they must be having a party for catching me. I was in my room for two hours, it seemed like 10. What were they doing down there?

"Terry, get your ass down here" Dad yelled.

I wasted no time getting down the stairs. Again all the seats were taken, and I stood in the center of the room. Dad looked at me and asked, "Terry, was that the truth that you told us before? That you were only trying to find out about any job openings at the resort, and that you didn't know the girls would be changing?"

I was home free now. I might end up grounded, but that's it. "Yes it was" I said, "I never meant to hurt the girls in any way"

Just then, I saw someone walk in from the kitchen. Oh My God! It was Mike. He started off saying, "Sorry Terry, but Becky said that I should call your Dad and let him know what you were doing. I didn't know that they had found out already."

 

Caught red handed. Dad just looked at me and started to speak. "You were planning to blackmail Sherry for a job. Sherry is a very close friend of Gales, which means that you hurt them both. We have discussed your Penance for this dishonorable act. Gale's parents have decided to give you a summer job at the resort. You will accept the job, and not question any part of it. Both Gale and Sherry will be in charge of you at the resort. You will be salaried, and not paid by the hour, but you will have lots of work to do. You will basically be a gopher at the resort, with many duties, and a uniform for each one. The girls will teach you how to dress and act, and most important, how to do your makeup."

"Makeup? What the hell are you talking about Dad? " I quipped.

"You will be working as a girl at the resort. All summer long, you will be learning how to be a perfect young lady. Gale and Sherry will be taking pictures of your progress each week for your scrapbook that you'll keep of the summer. It'll be like a diary with pics. From now on, you will call your Mother, Mommy. You will call me Daddy, like you are our little girl. We will refer to you as Terri Shawna, your new feminine name. If you don't agree to this, we'll call the police now. What's it going to be Terri?"

Wow. I get the job, but I'm forced to be a girl. for the summer. Or I could see what the courts would do to me. Some choice. "I'll do it, I'll take the job"

Gale and Sherry started snickering again, and an evil smile came over their faces. Gale pulled out a measuring tape and said, "Get up to your room Terri, Sherry and I will be right up to measure you for your uniforms. Take off everything but your underwear. You saw us in ours, now it's our turn. Get!"

I went up and stripped, and waited. They finally came up. They decided that Sherry would measure, and Gale would write it down. Sherry was making comments like, "God you're going to be cute in a swimsuit. Dressing up as a desk clerk in heels will be great, I just can't wait. You wearing skorts on the golf course, selling sodas, wearing that cute little visor and tube top. Wearing a maid's uniform in the morning when you change the bedding." She measured everything, even some places I didn't understand, like neck to crotch, and neck to knees. She measured waist to knees, but she was high above my waist. She never measured my inseam. She measured my neck, each wrist, and each ankle. She even slid rings on my fingers and marked them. Then Sherry said, "everything should be done by next week Terri, but we don't have much time to train you, soooo. I want you to remove all your hair, and practice doing your toenails twice a day, 2 coats each time. I want you to get your ears pierced too. Start wearing panties, and learn to sit when you pee, and don't forget to wipe. Your feminization starts tonight. Gale?'

"I want you to put all your underwear in this bag, Gale said, I have 4 pair of panties that I'm going to give you. They're nylon and in bright colors. You start wearing panties now, so take the briefs your wearing off and put them in the bag. You will panties to school, where you will sit to pee also. I want you to wear this pink nylon nightgown to bed tonight, It will help you feel "cute" and girly. Tomorrow's Saturday, and you are going to go shopping for girl's shoes.

 

Next morning Gale was up early getting ready when she knocked on my door. " Are you up yet Terri?" she asked, "we got a lot of places to go and Sherry will be here in an hour , so open the door and let me help you get ready before she gets here."

Get ready? Now what was she planning? Oh well. I better get up before I piss Dad off again. "Ok Gale, the door's open, what do I have to do?" I answered..

""First we have to shave your ankles, well probably your calves on down to your toes. Let's get to the bathtub and get started. You can sit on the edge of the tub and I'll shave you as I have more practice in this." she said with a smile. It only took a few minutes and my feet were hairless. Gale gave me some lotion to rub on my skin and we went back to my bedroom where she informed me that the easy part was over, "Now we have to do your toenails, sit on the bed, and put your feet up on the chair." She wound a rope between my toes, "Now don't move, this is quick drying polish, and you need 2 coats, and a topcoat that'll use up 45 minutes if there are no mistakes." God! I thought, Sherry will be here by then, and I'm still in panties and a see through nightgown.

"Gale, I have to change before Sherry comes here, I don't want her to see me like this, please let me change first." I begged.

"No way Terri, we don't have time, and besides, Sherry will see you in even more humiliating outfits than a nightgown. Now hold your feet still." was all she said as she started to paint my toenails a very bright hot pink. When she was done, Gale looked at the clock and left me sitting there all by myself. Ten minutes later she came back in jeans, tennis shoes with anklets, and a sleeveless top. She gave my nails another coat without saying a word, and left. I heard the doorbell ring, and I heard what sounded to be Sherry's voice. Damn, she had to be early. The laughter coming from downstairs was making me sick. All of a sudden the talking was getting louder, the girls were coming upstairs.

"Well the little girl has 2 coats of pink, but still needs a clear coat, you want to take care of for her?" Gale said as she handed a bottle of clear polish to Sherry.

"I'd love to help our princess get ready. My what a cute feminine nightgown you have on Terri, don't let the boys at the resort see you walking around in that! This is going to be such a fun summer Terri." Sherry said with a wicked grin, "Teaching you how to be so girly and how to attract boys."

I almost hit her right there, but I wanted this Saturday to be over with as fast as it could. Just then Dad walked by my room and stuck his head in, he saw me in my nightgown with my shaved feet and pink nails. He saw Sherry giving me the final touch on the nails, he looked at me saying, "The girls really made your feet look lovely Terri, they did good work didn't they?"

"Yeah Dad, they did."

"Are you forgetting last night already Terri, I told you not to call me Dad." Dad howled at me.

"Oh Daddy, I forgot. Please forgive me Daddy." I said playing it up a little bit. He shook his head and left. Now I was alone again with my tormentors. Gale said they had some clothes for me to wear shoe shopping, and she had Daddy's credit card. The girls made me change in front of them. They gave me a pair of pink cotton hi-cut panties, which I put on fast. Then a pale pink shirt. It was a short sleeve and kind of washed out denim with brass buttons. I put it on and it was a little short on me, it barely came to my waist. The buttons were on the wrong side too. It was a girl's denim shirt jacket, the two chest pockets were too small to carry anything, and appeared to just be there to draw attention to the breast area. Next came the knee-high stockings. They were almost invisible, but Gale said that I would need them to try on shoes. I put them on, and my pink toenails kind of looked sexy, in a way, in them. Finally the pants. They were a match to the shirt. Faded, worn looking pink. They were stretchy for being jeans, and tight in the crotch. They had front pockets, but no rear pockets to put my wallet in. The front pockets were not very deep, and were very tight, making them worthless. I had a hard time bending over with the jeans being so tight. They came down to my ankle, so I showed my shaved ankles when I walked. Gale bent down and placed an ankle bracelet with pink stones around my right ankle. She gave me a pair of old pink mules that looked like bumper tennis shoes to wear, and a pink fanny pack. I was all set. I was all pink.

The trip to the shoe store gave me a lot of time to think about how I looked. I looked liked a teenage boy in girl's clothes. There was no mistaking my outfit for menswear, or my shoes. Men don't wear knee-highs or pink fanny packs. I didn't know what to say if I ran into any of my friends at the stores. God, I wanted this over with. We went to a discount self serve shoe store first, the young lady working there asked if we needed any help. I was going to say no, but Gale spoke up, " Yes, my brother Terri here is in need of different styles of women's shoes, could you help him measure his feet, and help him select some shoes? He needs pink heels, in high and low heels, black in high and low, and a few pair of high heel open toe sandals. We will come back for him in about an hour. Is that all right with you?"

"I think I can handle it if it doesn't get too busy in here. How much can he spend on shoes, and does he need any boots? "the lady asked Gale.

"What ever you think he needs for the summer for work and play, but they must have heels, even the tennis. Pink really is his favorite color, as you can tell. He has to be a perfect young lady all summer long, so make sure his shoes are very feminine. Fashion boots would be cute." replied Gale as she was walking out the door, "Be back in one hour."

"Hi, my name is Judy" said the young lady as she pointed to her name tag, "I heard your sister call you Terri, is that Terri with an I or with a Y. Oh , I suppose it doesn't matter much, it sounds the same. Let's measure your foot honey, and get you some shoes." With that said, she got out that device for measuring feet, the one marked women's sizes and placed it by my feet. "Take your shoes off honey, and stand up, that's right, place your left foot on, heel all the way back. Let me set the width. Now the same with the right. Good. Both feet are a women's size 9M. You'll have a fairly easy time picking out shoes. What do you want to start with first honey, the heels?"

I could feel myself start to blush, but I wanted to get this done before any other customers came in. " Sure" I said, "might as well get the worst done first. Show me what you have in pink and black, high and not so high."

"Alright Terri, but I think you better try a 9 1/2 M or a 9W in the real high ones, just to be sure. Here's some cuties for the lower heel ones. They have peg shaped heels and thin ankle straps to help keep them in place. And for high heels, try those 3" pumps with the tapered chunk heel." Judy said as she got some boxes down off the upper shelf.

Judy was right, I needed a 9 1/2M in the 3" heels. They were a little lose, but the ball of my foot felt better. I had a hard time buckling the thin strap on the lower heels, and walking in them was harder than the high heels. Judy looked over at me and smiled at my predicament, trying to walk in the lower heels. Done with that , I took them off and placed them back in the boxes and brought them up to the counter.

"Place the top of the box underneath it, so I can check the size and price when you check out honey." Judy commanded me, " Look over here in our boot aisle, there's some shiny black high heel boots to die for. They'll go great with a skirt on a date honey. Try them on and get a pair that's tight in the calf, but roomy in the foot."

I went to the aisle and found the boots. They looked like liquid plastic, and were a little stretchy. I tried pair after pair of 9 and 9 1/2 in M and W and none fit. I was relieved that I wouldn't have to buy any of these slutty looking boots. Then Judy yelled to me, " They run a little on the small side, so you'll probably need a 10 wide honey." My happiness disappeared instantly as I saw a pair of 10 wide right in front of me. I reached out and picked them up. I tried them on, and the foot fit well. I zipped them up and they were tight, too tight I thought. Just then Judy came over and stuck her index finger in the top of the boot and said, "Perfect fit honey. Why don't you walk around in them for awhile, they look so cute on you."

I felt so embarrassed, but at least it was only Judy and I in the store. Then three senior girls from school came in, and stared at me. They giggled and one of them pointed at me and said, "Oh look at the little sissy trying on boots. I was going to get a pair just like them, but seeing them on him makes him look like a slut." I wanted to run and hide, but where. The girls followed me around the store, calling friends on their cell phones, and teasing me. Then Gale and Sherry came in.

"Take your new boots off Terri, it's time to see what you've picked out to wear this summer. Show me what you want to buy" Gale ordered. I took Gale and Sherry to the front desk and showed them the heels. "Put each pair on for us Terri, and walk up and down the carpet. Nice and girly now." I unzipped the boots and put the high pink heels on first. I walked up and down the carpet twice. Then the black high heels, and again up and down the carpet. Right about then, I noticed more senior girls coming into the store to watch me. I wanted out of there bad. The ankle strap heels took longer to put on and take off. I also was quite wobbly in them because of the peg like heels. "That's all you got in an hour? What have you been doing, trying on every pair in the store?" Gale barked at me, "Now let's find some high heel sandals and pink high heel tennis shoes for you." The audience was getting bigger and my stomach was getting sick. It took another hour before we left that store. I know that some of those girl's knew Gale and Sherry, and they must have figured out that I was Gale's brother Terry. I didn't want to go to school on Monday. Next stop was a department store.

We parked and went in to the department store and went straight to the lingerie section. Gale told the older sale lady there that I needed 21 pairs of panties. All to be in some color of pink. Nylon, satin, or stretch fabric. No cotton except in crotch. Hi-cut or boy-leg. She also told the woman that I needed 12 bras, also to be in pink, satin preferred. Push up or padded. Gale told her that I would have to be fitted. The sales lady said, "Give me an hour with her er, I mean him, and he should be all set when you get back." Gale and Sherry went to lunch, and all I could hear was the sales lady directing me into the back dressing room, "We don't want any others to know you are here being fitted. Let me see what size panties you have on, ah, size 6.Good. Now take your shirt jacket off so we can measure you for your bras." I removed my shirt, not saying a word. " Place your arms out so I can put this tape around your upper chest, now put your arms down. OK, now we want to measure over your nipples. 36A, we're going to need some padding. I'll get your panties together and we'll have to wait for your friends to get back." So I waited, looking at all the different colors of pink in front of me, realizing that I would be wearing them all summer long. Then Gale came into the room with the sales lady.

"We have a problem Terri, you're a 36A, and that's just not big enough for what we have planned. We are going to buy you some glue on breasts. Either 36B, or 36C, so pick one now." Said Gale.

"36B" I said quickly, not wanting to wait too long to answer, "that's what I pick!"

"36C it is then" Gale said to the lady, "You see Terri, I told the sales lady to give you the one you didn't pick. Don't worry, we're not going to glue them on here, just use them for cup fillers. Here she comes now with your bras, you know you have to try them all on!"

" I'll help you put these on, and adjust the straps for you. Tour sister said that she'd teach you how to put them on and take them off. That's so nice to have a sister who will help you become a girl for the summer. You're so lucky. "was what the sales lady told me as she adjusted my bra straps. I must admit that the bras fit good, and I looked like I really had big breasts. This woman was good at her job. Then she spoke again to me, " Your sister tells me you're going to need several pink swim suits, and that you want matching wrap skirts for when you're not in the pool. I can get you a terrific deal right now if you buy 3 or more. They are one piece. They are very cute, and they are high chest so that they won't give you away. Unfortunately, the bottom is very tight, and you will need to hide your manhood. The wrap skirts will help turn it into an outfit. Let me get one for you to try on. Wear only your bra and panty for now."

She brought one in and I tried it on. Boy was it tight in the groin. But when I put on the wrap skirt, I looked like I had a woman's body. Just then Gale came back into the room and gasped, "Sherry, get in here. You have to see this swimsuit on Terri. You look great Terri."

"Now what?" said Sherry, as she came into the room, "Oh My Gosh! That's great. The boys will be all over her. She can even wear it to drive out refreshments on the Golf Course. You'll need 4 of them Terri."

Finally we were on the way home with all my bounty from shopping. Gale and Sherry had told me that they had bought a lot of baby-doll pajamas for me to wear, as well as some more nightgowns. At least they got me a lot of pajamas. Sunday I was to start my training on how to walk in heels, and how to stand and sit like a girl. Easy day for a change. I put on one of my new matching bra and panty sets, my nightgown, and my pink slide slippers Gale had given me. Then I went downstairs to show Mommy and Daddy that I was ready for bed. I gave them each a little curtsy, just to bug them, then went up to my room. I pulled back the covers to climb into bed, and then I saw that Mom had changed my sheets to that of large pink flowers on a pale pink background. My pillowcases matched. Man, I hate pink already. Good night!

  

  

  

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