Jeff stood at the front window looking out as the car pulled up in front of his house. His mom had already gone out to meet the visitor and he saw the girl get out of the car. Just as he thought, she was very pretty. His heart started pounding in his chest just like it always did when he was faced with being around a cute girl. He didn't understand his shyness. He wasn't a nerd or anything, it was just very difficult for him to feel comfortable around good-looking girls. He saw her pull a large suitcase out of the trunk of her mom's car and he knew he should go help with it. So with all the courage he could muster, he marched out the front door to where they were struggling with the heavy bag.
As he got closer he found himself staring at one of the cutest girls he had ever seen. She had big blue eyes that were looking right at him. Long curly blonde hair fell in waves down her back and she had some of it pulled over her shoulder in front. Big luscious lips that had just a faint outline of pale pink lipstick on them. She was wearing a red sweatshirt that said "cheerleaders lead the way" on the front with a picture of a cheerleader jumping up in the air, holding her pom-poms up above her head and her legs wide apart. It was so cute. She also had on pants that were like warm-ups that had the word "cheerleader" spelled out in big letters running down the outside of both of her legs. He felt his face get redder and redder. He hated that happening to him in these situations.
Jeff's high school was hosting the Regional Cheerleading Championship that week-end for 20 high schools in the area and some of the cheerleaders were coming from places far enough away that they needed places to stay overnight. This girl was from Springfield which was about 75 miles from there, so she was spending Saturday night with Jeff and his mom. The schedule called for practice during the morning, competition in the afternoon and a banquet that night. His mom had told him they would attend the competition since one of the girls would be staying with them and they could go and watch her perform with her squad.
As he approached them his mom introduced the girl to him. "Honey, this is Cindy Harris. She's a senior at Springfield High School and is 18 years old. Cindy, this is my son, Jeff, who's 15 and a freshman at Lincoln High School here in town." Cindy looked at him with those big blue eyes and he almost melted right there on the spot. "Hi Jeff, I'm really glad I'm staying with you this week-end. I think we'll have a lot of fun." And she gave him this big hug that sort of took away all his inhibitions. It was almost like they were already good friends. He couldn't believe how relaxed Cindy was making him feel already. Maybe the week-end wouldn't be so bad after all. He picked up her suitcase and they all walked in the house together and he felt his heart beating a little differently than it had been just a few minutes earlier.
"Jeff, why don't you show Cindy to the guest room and make sure she has everything she needs," his mom said. So they climbed the stairs, Jeff following Cindy, and he was mesmerized by the cute figure walking ahead of him. As they got upstairs he momentarily forgot what he was doing and they just stood there. "Well, sweetie, do I have to sleep out here in the hall or are one of these rooms for me?" Cindy giggled. "Oh my, I'm sorry. I don't know what got into me," he said as she was grinning at him. She couldn't help but notice how flushed Jeff's face had been ever since she met him. She thought it was kind of sweet that she was having this effect on this cute boy. She liked being around a guy who had a shy side. They always seemed to treat her with so much more respect than most guys did.
As they entered the guest room Cindy noticed the clock on the nightstand, "Wow, our practice starts in just half an hour. I'd better get over to the school and get with the other girls on my squad so I don't miss anything. But I'll be back around noon and we can talk more over lunch. Oh, and would you be a real sweetie, Jeff, and unpack my things and put them away for me? I don't have time to do that right now and I have some things that will get wrinkled if they aren't out of that suitcase soon. Hope you don't mind." And with that she hugged him again and gave him a quick kiss on the cheek and bounded out of the room. He could hear her and his mom talking and his mom yelled to him that she would be back as soon as she dropped Cindy off at school. Jeff rubbed his cheek where she had kissed him. He looked in the mirror and saw she had left just a slight smudge of her lipstick on his cheek. He smiled as he thought about such a cute girl being so nice to him.
Then he remembered he was supposed to unpack her things. A little chill ran up his back as he lifted her suitcase onto the bed and opened it. Her fragrance wafted out of there as soon as he opened it. He loved the perfume she wore and everything in the suitcase was permeated with it. There was a pretty pink dress on top that he lifted out and headed towards the closet. As he placed it on a hanger he saw it was very short and pretty, like a party dress but not quite so fancy. He figured that was what she was going to wear to the banquet that night. He tried to picture how she would look in it and then went back to the suitcase.
Next he saw her cheerleader uniform. Her school's colors must have been red and white because the uniform was in those colors. He pulled out a very bulky-knit longsleeved sweater that had a turtleneck. Gosh, he had never seen such a pretty sweater. He held it up and saw it was all red except for two thin white stripes around the turtleneck, a wide white stripe that went the full length on the outside of both arms and over the shoulders, and a white stripe that kind of zig-zagged around the chest and back. Embroidered on the front was "Hornets" and an emblem of a hornet. On the back her name was spelled out in big, fancy letters "Cindy". On one sleeve there was "98" and on the other was four stripes, kind of like you see on Army guys shirts. Jeff held the sweater up in front of him and stood before the mirror. He had a sudden urge to pull it over his head because it was just such a beautiful thing, but he didn't.
He placed the sweater on a hanger and then saw the skirt that went with it. It was like a mini-skirt and was a red polyester knit that had several pleats along the bottom and when the pleats were spread, they were white along the inside. He imagined her twirling around wearing this and seeing the pleats rise and fall around her thighs. He held the skirt up against himself as he had those thoughts and started spinning around the room. After he had hung the skirt up he returned to the suitase and saw the cute little socks that she must wear with the outfit. They were white cotton with short cuffs and embroidered along the cuffs was the word "Hornets". Jeff wondered if she had pretty pink toenails hidden by those socks when she wore them. He placed the socks in one of the empty dresser drawers.
Then he saw the red spandex panties that went with the outfit. He started blushing again as he handled them even though there was no one in the room with him. They were very stretchy and he imagined they hugged the curves of her hips and butt very tightly. He placed them in the drawer too. Then he felt his face get very hot as he saw some very dainty lingerie towards the bottom of the suitcase. There were a couple of pairs of panties, a couple of bras, a very silky lace teddy and a couple of pairs of pantyhose. And towards the side was her cheerleader sneakers and a pair of pink high heeled pumps with about a 3 inch heel. He was trembling as he approached those delicate items of her most intimate and personal clothing. He thought he should get out of there for awhile and would come back to put those things away in a little while.
As he went back downstairs his mom had just returned and noticed he was a little flushed. "Are you OK, Jeff? You are a little flushed. Oh, I know, it's because of Cindy, isn't it? Well don't worry, she is a very sweet girl and she really likes you." "Mom, how do you know she likes me. She just got here. She doesn't even know me yet. What did she say?" "Calm down, honey. You must have made a very good first impression on her because she said she can't wait to have some time to be with you and talk to you. She even said you are VERY cute," mom kind of giggled. Jeff couldn't believe what she was saying. How could a pretty, sweet girl like Cindy care anything about a guy like him? But as the morning passed he couldn't get those words out of his mind, or stop thinking about those big blue eyes of hers looking at him, or remembering her kissing him.
Before he knew it, it was 11:30 and he hadn't finished putting Cindy's things away. So he rushed back up to her room and again was stopped by those sexy and intimate underthings of hers. He examined her panties and saw there was lace on the front panel of both pairs. One was pink and the other was yellow. Her bras were made of a very stretchy lace fabric and there were little bows sewn between the cups. There also seemed to be some kind of thin wire under each of the cups that sort of went all around the bottom of the cups. He shuddered as he read the tag inside of one of the bras. It said "34-A". He somehow felt very naughty spending this much time handling things that she wore on the most intimate parts of her body. But he couldn' help but wonder what she must look like in these dainty things. He bet the panties with all the satin and lace must feel good on her skin. And the bras must be tight around her breasts. And as he picked up her pantyhose, he couldn't believe how delicate and sheer they were. He tried to imagine how they would feel on his legs. As he was holding them in front of himself he heard somebody say, "I'll just bet they will fit you. You and I seem to be about the same size."
He turned to see Cindy standing there looking at him. He tried to make some excuse as to why he was holding her things up against him but she wouldn't let him finish. "Jeff, let's go have some lunch. Your mom's down in the kitchen fixing something right now. But after we get done eating, you and I are going to come back up here and have some fun. OK? My squad competes at 2pm so that will give us a little time. And you can help me to get dressed in my uniform. Would you like that?" She knew exactly what was running through his mind and she was so glad she had caught him the way she did. She had him pegged as a lonely, sweet guy who didn't know a lot about girls. But she was going to show him plenty before she left for home. As they ate lunch Jeff became totally relaxed with Cindy. She seemed to have a way about her that made him feel like she was his best friend. And she really seemed to like him. His mom was surprised, but delighted, to see her son having such a good time with a girl. She often wondered if he'd ever be able to get along with them, but it seemed Cindy was bringing him out of his shell.
When they finished lunch they went back up to Cindy's room and she asked Jeff why he was holding her pantyhose up against himself when she came back. "I'm not sure, it's just that as I was putting all your pretty clothes away I couldn't help but imagine what it must feel like to be able to wear such nice, pretty things. And I thought about how cute you are and how great you must look wearing this stuff. I guess I was trying to imagine what it must be like to be you," he confessed to her. She thought that was the sweetest thing anybody had ever said to her. She ran over to him and hugged him and said, "Well, thanks for saying I'm cute. And as far as feeling what it's like to be me, well, you'll never really know, but you can at least know what it feels like to wear my clothes. Wanna play dress-up?" Jeff wasn't sure what she meant by that, but he also knew he would do anything this pretty girl wanted him to do. "First, I want to make sure I can trust you. I'm already pretty sure I can, but you've got to promise me that you'll be good. OK?" He told her she had nothing to worry about with him and she knew he was telling the truth.
"OK. While I get dressed in my uniform we can get you dressed too. All I need out of the suitcase is that pair of very shiney pantyhose and those sneakers." Jeff then noticed that the pair of pantyhose she took were a little heavier nylon/spandex blend than the remaining pair. "Now I'm going to take all my clothes off and I want you to do the same thing. You pick out whichever pair of those panties you want to put on, the other pair of pantyhose and one of my bras. But be careful with those pantyhose because those are the ones I'm going to wear to the banquet tonight. Just don't get any runs in them." She was saying all those things as casually as if it were her best girlfriend there with her rather than a 15 year old boy that she had just met.
As she removed the clothes she was wearing Jeff was surprised when she took everything off. She was completely naked. "Well, what are you waiting for, little girl, let's get those ugly boys things off of you," she said teasing him a little. He had never seen a girl's breasts before and he thought Cindy's must have been about perfect. No sag to them at all. They pointed straight out and had very large pink nipples. He could hardly bring himself to look between her legs, but he sensed she wanted him to and he saw she had a very light covering of curly blonde hair at the top of her crotch. He couldn't see much else and was sure he wasn't going to get to. She walked over to him and helped him take off his clothes. He was a little embarrassed to be standing before her totally naked but she said, "Don't worry, I've got 3 brothers and you haven't got anything I haven't seen before." As she looked at his trim, almost hairless body she couldn't help but think he could have easily passed for a girl, except for that thing between his legs. She slipped into the red spandex panties and handed him the pink pair from the suitcase. She watched, fascinated, as he stepped into his very first pair of panties. She had a feeling this wouldn't be the last either, not by a long shot.
She then slipped into the pantyhose and he saw her legs take on a very noticeable sheen as the light caught them. She told him to put "his" pantyhose on too, and he carefully slid them over his toes, heels and up his legs as he had seen his mom do. When they finally rested around his waist he thought he had died and gone to heaven. His legs felt like they were encased in a wonderfully tight, silky trap. He never wanted to take them off. Cindy wasn't missing any of his reactions and she thought if the situation were just a little different she would probably make sure the sensations he was feeling were heightened by some sexual flirting. But she knew that would be improper right then. He kept watching her as she went to the closet to get the sweater and skirt and put them on. He thought she looked like the sweetest sight he had ever feasted his eyes on. She was the PERFECT cheerleader. He also noticed that she did have her toenails painted pink as she slipped the cute socks over her toes and feet and adjusted the cuff. And finally she slid her feet into her sneakers and she was finished. Except for touching up her make-up.
As she fastened her bra around him and had him slip his arms through the delicate straps she noticed a slight bulge starting to form in the front of his panties. She knew then that he was hooked. And she was envious that someday some other girl would get to be his girlfriend and dress him up this way. She felt a little sad that it wouldn't be her. But as she fastened the two bra clasps behind his back she smiled knowing it was she who first brought this side of his personality to life. Maybe she could meet another guy like him some day and do even more for him. "I have an idea. Why don't you wear those things under your regular clothes when you come see me this afternoon. It'll be our little secret. And if you wear a sweatshirt I'm sure no one will know you are wearing my bra. What do you say? It will be fun for us to have this secret in front of all those people." Jeff agreed and that afternoon, sitting in the stands of the gym next to his mother, he couldn't have been happier. A day that had started out with nothing but his normal feelings of insecurity had turned out to be a new beginning in his life. And here he was watching the sweet, pretty girl that had made it all happen. As she was on the gym floor with her teammates going through their routines, she flashed that big smile and winked at him knowing he was feeling a little bit of what it was like to be her.
As Cindy was leaving Sunday morning, she pulled Jeff aside and gave him the biggest kiss he had ever had. He tasted her lipstick as her lips met his and he savored the feeling of her tongue as it made contact with his own. She hoped she had given him more confidence in himself as she walked away from him. The last thing he saw were those big blue eyes looking at him and he thought he saw tears forming in them as she got into her mom's car. He was so sad for the rest of the day knowing he would probably never see her again. He might have felt a little better had he known she was feeling the same thing. As he went to his room, he noticed there was something on his desk. He went over to it and saw a note from Cindy that said: "Dear Jeff, I loved what we did together this week-end. I'll never forget it, or you. Here's some things to remember me by so you will always know how it feels to be me. I love you. Cindy" Under the note were the bra, panties and pantyhose she had put on him. Tears welled up in his eyes as he stood there.
Jeff did continue savoring what it felt like to be a girl. Because of Cindy he was even able to start dating girls but he never did find one who would share the joys of his feminine self. So he had to keep it to himself. At least until the day he started college at the U of I and as he was walking into the student center that very first day, he was met by these big blue eyes of the senior girl assigned to be his student-buddy for orientation. They both started crying and hugged so tightly and they knew they would never be separated again.
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