Andrea's Story

by Christy Lake and Misty Dawn

 

Andrew Winslowe is two years younger than his sister Sharla Winslowe. Strange things happen around Sharla and Strange Forces are at play. Andrew Continues his Quality time with Sylvia, but he got nosey and maybe a little rough on the wrong day. This is his story.

 

Chapter 2 Curiosity Zapped the Andrew

Thursday, the day school let out for the summer, Sylvia suggested that the next morning he should dress in that silky new shirt and those dreamy cream de menthe slacks--she had urged he buy them because they fairly displayed his sleek swimmer's form, so well that she nearly creamed her own whenever he wore them for her--and that Andrew and she should drop in at the office so he could be introduced to the rest of the staff. Though a little unsure of himself in such a role, she assured him that if he acted as polite and soft spoken as he did around the swim team, that he would do just fine. In the end, after hearing her promise of an enjoyable afternoon he would not soon forget, he agreed.

Actually the visit proved quite enjoyable. He was being introduced by the boss's daughter, after all and soon found he was being fully accepted, even though he was being treated more like "one of the girls" than the boy he was. He thought perhaps the silk shirt, slacks, penny loafers and his hair in a pony tail could lead one to think he might be a girl.

"Andy," she said, firmly setting the name he would be known as by all the staff. "I have to go see Daddy now," Sylvia excused herself. "Mary will take you and introduce you around."

Mary, Sylvia's dad's secretary, did not seem to notice he was not a girl and they were soon getting along fine. While he stood there talking with Mary, one of the men from the plant came into the office and when he saw Andrew, he smiled and told him "Good morning." This made the effeminate boy blush furiously as it was obvious the man was trying to flirt with him. Mary chuckled and told him not to mind the guys hitting on him; they did it to all the girls all the time. "They'll hit on any girl that comes in here, and when she's as pretty as you Andy, they try even harder." She laughed; mistaking his consternation, then went on. "They're not a bad bunch though, and at least we'll have some fun at the Halloween and Christmas office parties." Mary showed him the Ladies rest room, the only one connecting to the office, and then said; "I think it's great that Mister MacFarland is employing you for the summer. Every girl needs a summer job to make enough money to buy really sharp looking clothes for school in the fall."

Though it seemed unnecessary--surely she could see he was a boy--he told her again, "Mary, I'm a guy."

She merely smiled condescendingly at him and said, "That's okay honey, you'll get used to it, and be some one for me to talk to, girl to girl." Then she took his hand and began taking him from desk to desk, introducing him to the rest of the office. When they had made the rounds, she said it was time for lunch.

"Now, let's go have some lunch, shall we Andy?" Mary then took him to the employee's cafeteria and treated him to a delicious Chef's salad and tea.

Over lunch, she asked him if he had a boyfriend.

Finally giving up trying to convince her he was a guy, Andrew replied in exasperated tones, "No, Mary, I do not have a boyfriend at the moment."

Mary smiled and suggested, "In that case, you might take a fancy to one of the younger guys working in the plant." Her words reminded him of the guy who had tried to flirt with him a bit earlier and he blushed furiously. "Oh Andy, you do have such a cute blush! The guys will tease you all the time! Just to see you turn pink, girl!"

After they had finished lunch and returned to the office, Mary had him fill out some paperwork and told him "Andy luv, you might as well start Monday morning. That's the same day Sylvia is coming to work, so I can train you both at the same time."

Surprisingly, Andrew returned home confident that he would fit in perfectly when he started work the following week. In fact, he was quite enjoying the idea of flirting with the women in the office and was certain the boys coming into the office from the plant would be jealous. That the girls in the office seemed determined to treat him as a girl surprised him, but somehow did not overly concern him. The rest of the weekend--though it went quickly enough--he surprised himself, when he realized he was experimenting with different "looks" to wear at work.

After work, three days a week, he would accompany Sylvia to her house, change and go to the Municipal Pool. Together they would work on his physical therapy drills for at least a half hour. Then normally, he and Silvia and sometimes some of her friends would work together on some of the drills used by the precision team. And for at least a half hour, he and Sylvia would work on endurance and form. Sometimes she would take him home. Other times they would hit one of the "hang out" spots for a snack or check out the mall.

**********

Many of the Girls Speed Swimming Team girls knew Andrew from the spring before, and they stood in a group surrounding him. Most of them had day jobs and would congregate at the mall after work. When Andrew decided to wander the mall after work on Thursday, it was not at all surprising that he ran into some of the "Ghosts" hanging out with the "Gypsies." They knew he was an avid swimmer and that he was fun to be with. They also all knew that he had gone through something traumatic, but they didn't know anything else about him.

"We're going to the University pool on Saturday Andy. You just have to come! That's where we meet the guys!" It was the voice of Kelly, the bubbly one.

"Shouldn't I be objecting? I don't want to meet GUYS! Do I?" Thought Andrew as he listened with a strange, mounting excitement. "I'm not interested in meeting guys," he explained softly.

Claire and Cheryl said, "Oh, Andrew, come on! Don't be such a wuss! School's been out for two weeks! It'll be fun!"

"Heck Andy, you don't need to swim, just lie out there on the loungers and let the Dream Boats flock to you. That's what we do!" Urged Kelly.

"Why doesn't it bother me that they are treating me like just one of the girls?" The question flicked through his mind, but he had no answer. It really didn't seem to matter, what did matter was that the girls liked and accepted him and he reveled in it.

"I don't even have a decent swimsuit!" Even Andrew knew this was not an objection, but an utterly GIRLISH, 'Come on, convince me just a little' speech.

"You still have that sexy trunk suit, don't you?" When Andrew nodded, Chelle went on, "Wear that! It looked great on you." He wanted to have these girls as friends badly, so he gave in and said he would go with them. "And none of the guys will even notice the difference!"

"But, I want the boys to notice the difference! Don't I?"

"I'll have to ask Mom, but it'll probably be okay." Andrew couldn't believe he was even considering such things as asking his mother's permission to go swimming, much less actually ask permission to go anywhere. "Huh? I'm gonna ask mom if I can go swimming?"

That Saturday, still trying to put his worries aside, following their lead, Andrew sat on the side bench in a tank top and shorts, leaning back against the wall, waiting, and thinking as the girls went to their lockers to repair the damages their swimming had wrought. Suddenly he realized that while he had been admiring the girls partially clad bodies for hours, he wasn't sexually aroused. He hadn't realized before then that his normal interest in girls had undergone a subtle change. It seemed his interests were more like the interests he had in his sisters. Even then, now sitting there intentionally thinking of them, in terms and images that should fly the flag of his manhood boldly, didn't seem to do anything to raise Little Andrew.

**********

Shopping was Sylvia's all time favorite activity. On Tuesday afternoon, when she told Andy that she was leaving early with her dad, but would like him to come to her house after work to go looking for a good buy, he agreed. Sylvia was a fun person, and he would do just about anything, even carry bags in and out of Women's Clothing Stores, to be with her. He called the answering machine at home and left a message that he would not be home until late. He was going hunting the Good Buy with Sylvia. Momma seemed to appreciate the fact he had recently been letting them know where he was, who he was with, and when he would be home, just like his sisters had always done.

He had to take the bus to Sylvia's. When he arrived, she took him up to her bedroom where she got really embarrassed and serious. After a bit of beating about the bush, she took a breath and told him she wanted him to try something for her, to help her fulfill a fantasy, and then she promised to make it really worth his while. When she explained she wanted him to wear a pair of her panties, he balked. Then Sylvia kissed him. Andrew thought he knew something about kissing, but the kiss she gave him, made him change his mind. When he agreed to her wild suggestion, she kissed him again and once more he knew he would do anything she wanted, any time, any place.

A few moments later he had pulled on the shiny blue stretch briefs. He had not even gotten the elastic settled around his crotch when Sylvia was stroking and running her fingers around the openings. Little Andrew responded, "thankfully," Andrew thought. It did not take very long before the combination of her gentle fingers stroking his very rigid tool through the smooth fabric of the panties and her teeth nibbling and pinching at his nipples had the expected result. Just before he exploded, Sylvia moved behind him, slipped the panties down, and caught all of the ejaculation in her left hand while her right hand continued to stroke his body and tease his nipples. She continued to hug him from behind until he had completely softened and she had teased the last bit of male essence onto her fingers.

Then she guided him to a seat on the vanity bench and then very deliberately licked the glistening cum off one finger, and then, just as deliberately, slipped the finger into her mouth and sucked meaningfully. When she offered the next finger to his mouth, he never hesitated, licking and sucking just as deliberately and meaningfully as she had. As soon as they had thoroughly cleaned her left hand, she had him stretch his hands over his head.

Without warning, she slipped a bra, the same shiny blue stretch materiel of the panties on to him. The boy was not about to argue, he was too busy dueling tongues. When he saw what was coming next and started to object, she put one finger over his lips to shush him, then slid a matching slip over his head and again upraised arms.

When he stood, Little Andrew, still free of the scrunched down panties, was strongly demonstrating approval of the situation. "Ghad," he sighed silently. "If wearing girl's undies makes me come like that, I never want to take them off!"

"Here, Andy, try these on." Sylvia had placed several pairs of shoes next to the vanity. She slid to her knees and tried to fit a simple oxford onto his foot. It would not even go over his heel. "Drat! Okay, here, try these." The second shoe she tried was a conservative pump with a two-inch heel. His bare feet slid around in them. "These killers will probably be the ones to fit." With an apologetic glance she tried the remaining pair, light blue and white sandals with a slender three-inch heel. They fit. "yeh, I thought so." She buckled both shoes and then, still kneeling, helped him to his feet. "But, damn, they do look good on you, girl."

"Oh, my goodness! Looks like you're enjoying this, Andy, she giggled as she stroked the almost knee length full slip straight. Little Andrew was very noticeable. "Ghad, I just gotta check this out!

The slip bunched around her gold streaked brown hair as she slipped her head under the satin sheath and closely inspected this throbbing protuberance. A flick of her tongue had Andrew grabbing for the vanity mirror frame. His concentration was diverted to her fingers tracing the straps on the sandals when suddenly her warm mouth engulfed him. Time stopped for Andrew. In the vanity mirror he could see the lacy black fabric of Sylvia's bikini briefs stretched taut over lightly tanned, firm buttocks. He could also see the slender black of the bra straps going across her back and over her shoulders. "When did she undress?" Her gentle hands stroking his butt and thighs through the sensuous slip materiel as she bobbed back and forth, consuming him, amplified the flood of sensations produced by her active tongue.

All too soon, from his viewpoint, he lost control and exploded in her mouth. She kept a vacuum lock on him swallowing until Little Andrew softened. As soon as she released him, Andrew slumped to his knees also and gave her a gentle but heartfelt hug of thanks. Her gentle kiss gave him a taste of himself. Without being prompted, Andrew pressed Sylvia to her back on the floor before him, and drawing her panties off, tasted her as she had tasted him. Long, languid moments later, they knelt there in the middle of the floor sharing a hug and gentle kisses until they had partially recovered.

Sylvia was the first to her feet. She slid her feet into transparent mules with a two-inch spike heel and then slithered into a black slip, almost exactly like the one Andrew was wearing. She helped him to his feet, tucked Li'l Andrew away, and tugged his panties up, then smoothed his slip down before inviting him to the kitchen for something to eat.

Sylvia suggested a Chicken Breast Chef's Salad for dinner. Andrew quickly agreed and was put to chopping while Sylvia found the chicken, peppers, eggs, lettuce, and dressing. While they worked, he found the click of their heels on the ceramic floor of the kitchen mildly erotic and felt a resurgence in Li'l Andrew, who was beginning to strain against the front of his panties. When Sylvia snuggled up against his back, he realized that she had somehow shed her bra. Reaching around him to show him how she wanted something chopped or cut was definitely erotic.

It wasn't long before substantial bowls of salad had been prepared and tossed. Two places were set at the table in the breakfast nook, and Sylvia had poured two big glasses of milk. When they finished their meal, Sylvia explained that she wanted his help with four more of her fantasies. She explained that she wanted a man to take her through the back door, but both of them to be wearing a dress and heels. Her second fantasy was to make passionate love to a man, but this time with both of them completely dressed to go out on the town or to some upscale event. The third fantasy was to make slow passionate love with the same man, but this time in bed, with both of them wearing sexy nightgowns. The fourth and most difficult fantasy was to do this over and over, every week if possible.

Andrew glanced down at his blue nylon clad form and then at the beautiful, vulnerable woman across the small table from him and offered to do all he could to help fulfill all her fantasies..

Sylvia explained that her parents were avid golfers, gone every Saturday from noon until late and devout bowlers, bowling in two leagues every Tuesday night.

A very tired Andrew left at 10:30 to catch the last bus to his home. He had a pair of shiny black panties in his pocket that he had promised to wear to work tomorrow.

The next morning, he was worried. Sylvia was keeping away from him. She would not even join the group for lunch but disappeared. Shortly after lunch, he was working in the stock supply room when he heard the heavy thump of the door closing and the snap of the lock being set. A quick rattle of heels on the mosaic tile floor and Sylvia was wrapping her arms around him from behind and dropping a plain white plastic shopping bag on the floor. In just moments her nimble fingers had opened his slacks. In seconds her hands were inside his panties and had him quickly shooting a load into her hand. Awhile later, she told him again how much she enjoyed devouring his flesh and swallowing his seed.

While sharing his seed with him she explained that the first time she had seen him that morning; he had been polishing the conference table. Because she knew what to look for, she could tell that he was wearing the panties she had given him. It excited her so much that she could not control herself and had to stay away. After her great experience last night, she had gone out at lunch and purchased eight pairs of Lycra panties in pastel colors for him. Now she was worried about him being able to clean them without problems at home.

Giggling in a positively girlish manner, Andrew explained that in the Winslowe household, when they entered the fourth grade they were declared able to change bed and bathroom linens. When they entered the sixth grade, they were responsible for care and cleaning of their own underwear. When they entered the eighth grade, they were in charge of cleaning all their own clothes for them selves. Wearing and cleaning the panties would not be any problem for him. "Not only that," he had told her, "Mom and my sisters have trained me well in the art hand washing my own underwear."

After they had licked her hand clean, she refastened his pants. Between light kisses, she confirmed that he would indeed be willing to dress up with her every Tuesday evening. Then she offered to help him with some of the isometric swimming exercises, if he was willing to come over to her house on Saturday afternoon. "I want you to come in the backdoor, Saturday, Andy."

Saturday was bright and sunny. Andrew arrived a little after one and Sylvia met him at the door. She was wrapped in a "shorty" beach wrap. Without hesitation, she invited him to the big pool deck out back. The back yard with tall dense hedges around the perimeter was very private. Sylvia had run off some mimeographed sheets of some old exercises and after quickly explaining them, began going over the stretching and bending exercises with him. The young "tutor" suggested he shed his sweatshirt and jeans so he could really get into the exercise. They could critique each other. When Andrew was hesitant to shed his jeans because he was wearing panties, Sylvia whipped off her wrap, exposing her magnificent body clad only in lace front, ivory bikini briefs and a sheer lace, ivory front closing demi bra.

Following that sinfully scintillating Saturday, whenever Andrew was home alone, he would look at the various women's magazines his mother and sister's left lying about and imagine himself using the feminine products, whether the ads were for makeup or feminine hygiene products. A special treat was looking at all of the women's dresses, sportswear, lingerie, sleepwear and shoes in the big store catalogs the family received every spring and fall and left laying about the living room and family room. Even more titillating was the fact that lately he'd begun dreaming of being a girl and wearing such pretty girlish things. Without his realizing just when, items such as panty and bra, shorts and tops, skirts and blouses, dresses and heels became the focal point of his interest. The snug, really short shorts that seemed to enhance and display the butt were his favorite, and since boys could wear shorts…

*************

It was a couple of weeks after summer school started. Sharla had left for an early class. Mom had gone somewhere and said that she would not be home for lunch. Dad was at work. Andrew had the day off. Andy wondered what was so special about the heavy, beat-up, hand-tooled, ratty old box Sharla had bought and dragged home with her. Finding himself alone in the house, piqued with his driving curiosity, he easily slipped the useless, to his way of thinking, lock she had had installed on her bedroom's door.

He moved into Sharla's room and cautiously opened the intriguing La Caisse, as she had called it. Carefully he looked through each of the fifteen shabby-looking, rotting leather bound books of blank paper. Nothing! Blank books! No, maybe something was hidden under the cover! He carefully examined the binding of the Green book he was holding. Not very carefully he twisted the cover to see if there was something hidden in the spine of the book. He felt a little shock and a bit dizzy and then decided he had been sitting on the floor too long. He rather carefully put the old book back in its box.

Andrew looked around a bit then wondered if Sharla would let him borrow that sharp-looking red silk blouse he had seen hanging in her closet. Finally, he slipped out of her room, making certain the lock he found so ineffectual was properly secured.

As he strolled through the kitchen, the radio was announcing, "Today, June 21st is the longest day of the year. Solstice, the turning of the seasons officially happened last night at 9:01 P.M."

"Huummm," he thought gazing out the rear window. "Wonder what the other girls are doing down at the pool today?" He shook his head, trying to clear it of the idea he was a girl. "Where's that silly idea come from anyway?"

It was just a few hours later, Andrew sat at the kitchen table, considering Sylvia's tardiness sipping a Dew and watched the debacle of his sister's hurried departure for work with detached interest. "Mom!" Sharla urged in a voice just short of being mistaken for a hog caller's. "Hurry every chance you get, will you? I don't want to be late again!" She stood waiting with some impatience just inside the back door leading out to the detached garage.

Damn, those shorts sure look good on her. I wonder what I'd look like in a pair? The boy tried not to show the sudden concern on his face as he wondered again where all these strange thoughts were coming from? And more than ever the past few days!

"Andrew, be a dear and do up those few dishes left from lunch while I'm gone," his mother suggested on her way out the door following Sharla.

"Sure, Momma, I be glad to," he replied to her retreating figure. Momma? I've never called Mom, Momma in my life! Then, without giving a thought to what he was doing, the teenaged boy took another sip of the soda, went to the pantry door, took an apron off the hook and dropped it lightly over his head and tied it about his waist before beginning the dishes he had been asked to do.

Doing dishes was nothing strange to Andrew. In this family, everyone, including dad, washed dishes and cooked. No, the strange thing about it was that Andrew used an apron, and not just any apron, it was one of the frilly, ruffles and lace bib aprons women loved, today. Now what the blazes possessed me to wear that thing? He asked silently when he finally realized what he had done. Guys don't wear frilly aprons!

Not too many minutes after hanging up the apron, the teen, unable to fathom why, found he was again inside his sister's room, staring unabashedly at her closet. "Wow, she's got nearly as many clothes as Sylvia!"

Sharla had many pretty things that she had hardly ever worn. Just looking at them in all of the pretty colors and lovely fabrics as they hung in the closets caused Andrew's head to spin. He began just looking at these lovely clothes. Oooh, I just can't imagine having so many pretty things to wear! The thought flashing through his mind stunned him! What the hell am I doing here? And then he moved slowly forward, quivering with unaccountable excitement, started sorting through the closet and finally looking through bureau drawers picking out different things he'd like to wear.

He could imagine what they might feel like against his skin, then forced himself to quit thinking like that. "Dammit! Boys don't think, or do things like this! Do they? But why don't they? I would love to feel such softness, to feel sexy inside and pretty outside!" He nearly shouted this at the reflection of himself in the mirror above her dresser. But the stern voice did not change the tug at his mind. He still WANTED to feel these soft, slinky items against his skin. "Dammit, I KNOW that I like wearing Sylvia's underclothes, just wish I knew WHYit feels so right!"

Several items looked like they still had the original price tags on them. With mixed feelings, compulsions and urges, he started getting undressed. Then he suddenly paused to consider what he was about to do, and he almost died of embarrassment. It was bad enough to be a sixteen-year-old boy standing naked in front of his sister's dresser and closet in her room but to be there about to get dressed in her clothes was unthinkable. "For God's sake! I AM a boy! And boys do not dress in their sister's clothes!" He snarled, slamming the drawer shut and literally forcing himself to get dressed and out of the room. "I know why I wear Sylvia's panties and stuff! But why would I want to wear my sister's?"

**********************

Having a real, full time, office job had given him a lot of status. Being seen three nights a week at the big city pool with Sylvia and the other girls had not hurt his image either. Then, just last week, he had spent the entire week, from seven in the morning to ten at night prowling the fair grounds with Sylvia. It was surprising how many private little cul de sacs an enterprising, and horny, young couple can find in the midst of the crowds inundating the fairground during State Fair week. They had been the mobile gophers for the Fair Grounds Management on loan, with pay, from her father's company and had made the most of their time together. Once Sylvia left for University, their time together would be rare.

Summer had passed a lot faster than he thought it would. He had landed the job and had been working a full 40 hours a week. True, Office Assistant, his official title, had meant he was gofer for everybody, but it was still great fun. At first he had been pretty hesitant, a young guy, the only guy, in an office of twenty-eight women. They had taken it as shyness and pulled him into the conversations. But by the time the Fourth of July office party had rolled around he had loosened up and was used to being considered one of the office girls. Even most of the guys in the plant had called him "Miss" Winslowe when they saw him. He'd never gotten used to it and blushed often.

Near the end of summer, he realized he was in pretty good shape if a bit on the feminine side. That could be explained easily enough. During the entire summer, he had hung out quite a bit with Sylvia and her crowd, and they had also treated him as one of the girls. The one thing Sylvia loved more than anything else was shopping. And Andy had discovered that he loved shopping with Sylvia; of course he'd had a very special motivation. And he now had a complete new wardrobe, if a bit on the feminine side, and almost everything had been purchased at just a fraction of the normal retail cost.

And by the time the end of the fair came, Andrew, more often Andy by then, was moving naturally like a girl, talking like a girl, and as Dad said, even beginning to exhibit feminine wiles, just like his mom and sisters. Dad said this after Andy, using the very girlish technique of serving fresh-baked cookies and fresh made coffee and a hug, had persuaded him to lend him some money to buy a "pretty" new shirt he had seen in one of the mall's boutique shops.

Just a few days later, Momma said that Andy looked prettier with a little make up. What was a real surprise to him was that Dad agreed with her. Later, just after the fair closed, Momma helped him put on clear nail extensions, and one weekend just before school registration, Janine was home and styled his hair for him. Through out the month of August, Andy did wonder, once or twice, why his parents didn't object to his becoming so effeminate? The sad part was when Sylvia said good bye to her "Backdoor Bandit" and had left for University the next day. During registration, he saw Frank for the first time since school let out for the summer.

********************

Frank had been out of town most of the summer, working with his grandparents on their farm. Ever since he had gotten back yesterday, he'd been catching up on the gossip and learned of the three times a week swimming pool "Dates" that Andrew had been having all summer with Sylvia MacFarland and the past week when Andrew and Sylvia were seen together all week at the fair grounds all day, every day. He put two and two together, read between a few lines, and now felt he had a pretty good picture of how Andy had spent his summer. That twit had better not have been mistreating my little buddy!

The conversation that was taking place during the lunch hour while they were at School registration was animated and punctuated with agitated remarks and gestures. Questions like, "With Sylvia leaving for University, who are you going to do for entertainment?" and "What you going to do about all those soft flowing, girlie clothes and all that "so lovely" long hair that Sylvia's talked you into wearing?" were easily overheard. "…gotta admit it though, those girlie looking clothes do look sorta right on you, Andy."

Strangely, even though Frank was really curious, if he were to be truthful, he admired this new look of his little buddy, and really didn't want to see Andy drop any of it. He was a bit surprised that beautiful girls even now surrounded Andy and that they had been there all summer. "And in those tight shorts he's wearing…" He thought, trying hard not to be caught looking at Andy's sorta girlish butt almost as blatantly on display as the girl's crowding around him.

Intriguingly, Frank finally had to admit that he, too, was drawn to his little buddy's sleek new aura—so damned girlish it was actually "sexy"--in ways boys are not supposed to be drawn to other boys. Even so, as the days grew into weeks, he could not deny the tightening of his groin almost every time he looked at those long sleek swimmer's legs and that round girlish bottom he seemed to display in snug slacks or shorts most of the time now.

"Damn," Frank told himself silently, "It is gonna be one helluva year!"

 

 

 

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© 2002 by Christy Lake. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.