Military School Crossdresser
by: Kresha Matay

 

Tim was a sensitive young boy, bright and intelligent, but lacking many of the physical characteristics of Joe, his father. His father had wanted a son who was interested in sports, hunting and fishing just like himself. Unfortunately, through no fault of his own, young Tim couldn’t measure up to the desired image. Joe had expected his son to grow up to "be a chip off the old block" and when he didn’t, his father felt "cheated".

Tim might have grown up the way his father wanted if he hadn’t contracted Polio at the age of eight. The youth was paralyzed from the waist down. Though he did completely recover the use of his legs through a long series of operations and physical therapy, the doctors felt his growth had been impaired. He would never be as big or as strong as he might have been. Due to his illness, Tim also missed a lot of school and was two years behind his age group. These shortfalls caused the father to ridicule his son whenever he failed to satisfy the man’s absurd notion of what his child should be like.

When this occurred, Tim sought consolation in the loving arms of Rita, his mother. Here he found the love and emotional warmth he so badly desired. This only added to his father’s frustration and reinforced his resentment against both his "sissy" son and his "coddling" wife. This hostility was augmented by the "darts" Joe received from his macho chums at work whose sons all played Baseball and Football. His constant bitterness manifest itself in a pattern of physical, mental and emotional abuse against both the mother and son. As most often happens, the mother, protecting her only child, transferred her love from the husband to the son and vice-versa.

Tim, now in the initial confusion of puberty, misunderstood his mother’s attention and developed a strong personal attachment to Rita, her belongings and more specifically...her clothing. Any personal item of his mother’s became a symbol of the good things in life to the confused youth. Everything that belonged to her was pretty or beautiful or made him feel safe, "warm and fuzzy". Everything that belonged to his father was rough, ugly, caused him pain and got him into trouble. He rationalized, if he had been born a girl, he wouldn’t have been expected to be knowledgeable about cars, guns, sports equipment or tools, all the things he hated.

This eventually led him to secretly playing with his mother’s personal items. One day, he took his mother’s underwear from the clothes hamper. Dressing up as a girl, he fantasized he was Rita’s daughter instead of her son. He so thoroughly enjoyed the fantasy that he repeated his actions every time he was alone. With each new incident of crossdressing his fantasies evolved till he developed a second persona as Sarah...his mother’s daughter. As he grew older, Tim found he enjoyed the crossdressing more and more along with the emotional excitement he derived from it.

One day while performing a surprise cleaning of his bedroom Rita discovered an assortment of her recently "misplaced" lingerie hidden inside her son’s pillowcase and between his mattress and the box springs. Realizing how they must have gotten there, she suspected that Tim used the lingerie for purposes of arousal and masturbation. Amused and concerned at the same time, she decided to confront him. That afternoon, upon his arrival from school, she called Tim into her room.

Rita, holding up the confiscated lingerie in her hand, said, "Young man, would you explain why I found my lingerie hidden in your pillowcase and under your mattress? I’d certainly like to hear what possible justification you might have that would explain how it got there, why you’ve hidden it there, and what you wanted it for in the first place!"

Confronted with the evidence, the youth broke down in tears, admitted his crossdressing and explained the fulfillment he derived from wearing her clothes. Holding nothing back, he declared how badly he wished he were her daughter instead of her son.

The intensity of his desire to be her daughter surprised Rita. His confession projected not a simple fondness for her clothes as she might have expected, but a sincere desire to change his gender. Rita, in an effort to discover how deep his desire ran, began asking a series of disguised questions. The answers ultimately convincing her of Tim’s sincerity and more critically...his desire to be female. Assuming he would continue to borrow her clothes and crossdress no matter what punishment or corrective action she enacted, Rita decided that the best course of action was to allow him to pursue his crossdressing, but under her protective guidance. Afterall, she mused, "The remedy is more likely worse than the actual problem." She secretly "felt" he might eventually outgrow his fetish as the novelty of wearing her clothing with her consent wore off.

Rita’s decision was partially influenced by her absolute certainty as to what her husband’s ugly reaction to Tim’s crossdressing would be. She promised Tim she would keep his secret from his father, but warned him to be more careful in the future. Rita demanded his absolute promise that he would crossdress only when his father was away from home and only in her presence. Tim enthusiastically agreed to her demand when Rita offered to teach him how to dress-up and also offered part of her wardrobe to him as his own.

Over the next three years, she kept her promise by presenting him with various feminine attire including dresses, skirts, blouses, high heels, a panty-girdle, nightgowns, breast inserts, panties, slips, nylons, bras, pantyhose, garterbelts, costume jewelry, make-up and even a long tressed blonde wig. These were kept in her clothes-closet (by this time Rita and Joe were sleeping in separate rooms), with the understanding that they were really Sarah’s to enjoy. As his secret crossdressing became a larger part of his life, his mother’s involvement also increased.

Rita came to realize how much happier both she and her child were when he dressed as her daughter. Deciding his life, as a boy was miserable enough, she began to encourage Tim to become feminine more often.

The next level in her son’s transformation was natural and easier...she assisted Tim in his attempts to mimic the gender differences. Now she used all their free time teaching him feminine mannerisms. She trained him in the art of applying makeup, coached him to speak with a higher, yet softer, and gentler voice. In essence, becoming his gender tutor. By the time he graduated junior high (at the late age of eighteen), he could comfortably pass as her lovely young daughter. Tim could easily mimic the way a young woman walked, talked and presented herself. He had mastered all the subtle mannerisms that differentiated the genders. When dressed in his feminine raiment, he truly became his alter ego Sarah. All this occurred without the slightest knowledge of his abusive father.

His mother, who had always wanted a daughter, now found an answer to her lack of one. Whenever her husband left for an extended fishing, hunting or business trip, which was quite often, Tim would spend the entire time-frame dressed as Sarah. As soon as her husband’s car pulled out of the driveway, Rita would call Tim to her bedroom and transform him into her lovely daughter. They would pass the whole time just as any other mother and daughter.

As Tim grew within the role, they ventured out-of-doors, taking short trips into the real world. At first, these were car rides late at night, with little chance of discovery. As they both became more confident with his ability to pass, they added short stops at McDonald’s and other fast food restaurants.

The next logical progression was running errands as mother and daughter. With each new success came more daring adventures. One momentous day Sarah and Rita decided to go to the mall for some shopping. The day was a total success! They shopped all the women’s stores, taking great pleasure in Sarah’s ability to "fool" the saleswomen. They tried on dresses, bought new lingerie, bought high heels, bought cosmetics, had lunch in the food court and took in a movie as they thoroughly enjoyed Sarah’s newfound freedom. After this successful outing, they went everywhere as mother and daughter. No fears, no concerns, truly comfortable within their characters. Two females going to museums, art galleries, restaurants and theaters like so many other mother’s and daughter’s. If there was a good play being performed, that’s where they would be found, dressed in their finest feminine attire, reveling in their joint womanhood.

At home, in the evenings, adorned in their silky negligees, Rita spent hours talking about her life as a young girl. She told Sarah stories about her girlhood, her dates, her first kiss, her first love and the first time she made love. They sat for hours like other mothers and daughters, talking about clothes, hairstyles, make-up and how marvelous it was to be female. They would nervously giggle and laugh at the idea of Tim’s father finding out about "Sarah". Their conversations included such topics as how his mother felt as a woman. What her dreams and fantasies were and had been. How she viewed men and how she felt about her marriage to Joe. Each time they chatted was another learning experience for Sarah. The information Sarah’s mother related provided her with a superior understanding of the feminine gender, i.e., how the female mind worked, what were the "precepts" of womanly conduct and how his mother viewed her status in society.

One evening, when Tim asked a question about female sex organs and how they functioned, Rita went to Joe’s bedroom, opened her husband’s dresser drawer and extracted a few of his "hidden" girlie magazines. Then using the most explicit pictures of the absurdly posed models she described all the erogenous areas of the female body and the passion women derived from love-play. Having gone this far, it was a small step for her to describe the various techniques that excited a woman. She explained how most men expected their own sexual satisfaction without concern for their partner. This occurred because men felt superior to women and how stupid an idea this was in reality.

"Women should always be treated with the greatest respect and should never be used as a sex toy! All the courtesies and culture that make up human civilization are the results of female efforts to make our lives more beautiful and more satisfying. I want you to always remember, almost any male can father a child, it takes a woman to give the embryo life, to nurture and carry the child in her womb as it develops and then when she gives birth the future of our civilization is guaranteed. That’s why I expect you to always regard women with honor, reverence and esteem."

While Rita felt totally comfortable discussing any topic with her daughter, she remained guarded in her dress. Though she assisted him in his transformation and at times they helped each other get dressed, she never allowed either herself or Tim to be totally nude in front of the other. They did, at times, walk around the house in panties and bras, but that was as risqué as they got. Theirs was not a sexual situation, but one of love and understanding.

This closeness between the two and Tim’s expanding girlish traits didn’t altogether escape the notice of his father. While their secret remained hidden from him, he now thought his son was turning gay. Joe decided that Tim needed discipline and physical training to "make him into a man". When Tim was eighteen, he was sent to a military boarding school to finish his last two years of high school. Rita protested most vehemently but to no avail.

Now Tim’s life changed dramatically. He was still the subject of daily ridicule, but now it was the other male students, not his father who mocked the well-bred boy. The other cadets instantly recognized and made fun of his gentle voice, mannerisms and polite attitude. In addition, he no longer was able to escape into his other persona...Sarah. As the days went by, he withdrew from all contact with the other boys at school.

One Saturday morning, when most of the other students were home on weekend leave, he stayed rather than go home to his father (Rita was away). He decided to walk over to the main building to get change for the Coke machine. This was his first time inside the offices of the school. He had, of course, noticed the female secretaries when they walked to the cafeteria (all the boys had, since they were the only women around), but had never spoken to any of them. As he opened the office door, he was run into and knocked over by the two small sons of one of the secretaries. The woman ran over to see if he was hurt at the same time yelling for her kids to, "Stop!"

"Are you hurt? No! Good! Please excuse my children, I brought them with me because I couldn’t get a sitter and I have all this paper work to finish by Monday. I don’t know how I’m going to get it done and watch them at the same time. Oh, I’m sorry, I’m Mrs. Kinzie and these two rascals are my son’s Jeff and John."

Tim introduced himself, then said.

"It’s a pleasure to meet you Mrs. Kinzie. If you need someone to watch the boys, I’ll do it. I’ll take them to the gym where they can run and chase as much as they want and won’t be in your way, so you can get your work done."

This offer was met with cheers from the boys and after a slight hesitation, grateful acceptance from their mother. In the course of further conversation, Mrs. Kinzie suggested he call her Jean, at least when none of the school officials or other cadets were around. When Jean offered to pay him, he graciously refused her offer. After Tim and the boys left, Jean returned to her desk, but instead of resuming her work, she thought out loud.

"He’s not like the other students in this school. They wouldn’t have offered help to one of us secretaries. They’re so stuck up and "macho" they only stare as we walk by while making indecent gestures behind our backs. He’s different, more sensitive and much more responsible than the other students. I wonder how he manages to cope in this milieu? If he stays that way, he’ll make some girl a wonderful husband and probably a great lover. Not like that insensitive bastard I married! I hope his new wife gives him what he deserves, a whip across his ass. That’s just what he needs to teach him respect for all women!"

Jean was a strikingly beautiful and sensuous woman of twenty-two. Her classically molded features, crowned by a mass of auburn hair, were complimented by the firm fullness of her breasts, flat stomach and carried by two lovely defined legs with finely turned ankles. While some of the other secretaries might have appeared sexier (they wore more revealing clothes), she was the one who constantly received requests for dates, but refused them all. Being a working mother, a surrogate father and raising the boys left her little time for a social life. Also, being "used" by another male was not a goal she desired. When sexual frustrations reached a peak she could no longer control, she shamefully fingered herself to an orgasm. Of late, it was getting more and more difficult to reach fulfillment, also her needs seemed to return quicker.

Thinking of her EX and how unsatisfying they’re past sex life had been, caused desire to intrude into her consciousness and a warmth began to build between her legs. Without realizing it, her hand crept to her rising breast, where she was surprised to find her hardened nipple protruding against the bodice of her peasant blouse. As she brushed her fingers against the cloth, she moaned in pleasure. Her conscience told her she should stop, but her fingers refused to obey. Leaning back in the chair with her legs splayed, she pinched the pouting nipple of her left breast. Almost out of control, the shock of passion that drove through her body caused her high heels to "rat-ta-tat-tat" against the floor tiles. Jean felt the wetness building in the crotch of her panties. The fire in her pussy sent her last inhibition up in smoke. Raising her buttcheeks, she drew her tight skirt to her waist and slipped her hand inside her panties. Using her middle finger she found the source of her passion. With her eyes closed, she fantasized a faceless young lover teasing her hardened clitoris. Each flick of her fingertip equaled the flick of her lover’s probing tongue. She installed in her fantasy lover all the special qualities of sensitivity and lovemaking she most wanted from a man. As her emotions rushed towards orgasm, her fantasy lover raised his head. The shock of recognition brought her to a screaming, leg-trashing climax. The most powerful climax of her twenty-two years. The face in her fantasy was Tim’s! As her passions subsided, her shame and confusion grew. Her mind raced to find an explanation. None being available, she began to cry softly.

"How could I play with myself, here of all places and why would that sweet boy’s face be the one in my fantasy. Am I so horny I’m going to start seducing tender young schoolboys? Have I no shame?"

In an effort to compose herself, Jean straightened her clothing and proceeded to the ladies room. On the way back to her desk, she heard the laughing voices of her two sons emerging from behind the closed doors of the gym. Deciding to see how they were getting along, she reached for the door handle when she was struck with a concern.

Checking on the boys might be construed, by as sensitive a youth as Tim, as questioning his ability. Not wishing to hurt his feelings, she turned and took the stairs up to the second floor. A four-foot wide landing ran along three sides of the gym. Stepping quietly through the swinging doors, Jean found she was positioned directly over where the three boys were playing. They were obviously having a good time wrestling with each other on some foam mats left just for that purpose. In a moment it became obvious that it was her two sons paired against Tim and he was holding back, allowing them to "pin" him to the mat. Just then, they pushed him over on his back, one pinning his arms while the other sat on his legs.

Tim’s eyes momentarily met hers...she was discovered. In the same instant she realized he was no longer looking at her face, but was instead, staring up her skirt. As quick as she realized what was happening, that’s how quick another fire grew in her womb. Grasping the open railing for support, she closed her eyes and again imagined young Tim’s head positioned between her splayed thighs, stroking his tongue against her pussy lips, munching gently on her clit. A soft passion-filled groan escaped from between her clenched teeth. Jean, lost in her fantasy, didn’t understand her next action. She found herself spreading her thighs even farther apart thereby exposing herself completely to Tim’s view.

Tim enjoyed playing with the two boys. He knew he could beat them because of his weight and size, but decided to let them win. When they pushed him to the mat he found their mother looking down on them. His eyes were quickly drawn between her legs and up her skirt. His position enabled him to see the exposed welts of her nylons and the whiteness of her naked thighs before they merged into darkness. He fully expected Jean, based upon his understanding of how a woman should protect herself from exposure, to immediately step back or at least tightly close her legs. When instead, her thighs spread even wider apart, he rationalized that Jean didn’t know what she was "showing". His eyes ran up past the welt of her nylons and were only stopped by the thin strip of white lacy nylon covering her womanhood. Not able to tear his eyes away, he felt the dick in his shorts thickens and then push its way down his leg.

Jean "felt" Tim’s eyes on the center of her passion. With her eyes still closed, she immersed herself back into her earlier fantasy, "sensed" his trusting tongue against her trobbing clitoris and without touching herself, orgasmed profusely. Her legs violently shook as her pussy drenched her panties, her womanly juices running down her naked thighs. It was as strong and satisfying an orgasm as the last, all without any physical contact!

Tim, unaware that Jean was in the grip of an orgasm and spurred by his fear of discovery, quickly admitted defeat to the two boys. Using the excuse of having to pee, he rushed off to the john, but not before Jean looked down and was pleasantly shocked to see the large hard-on he unsuccessfully tried to hide. Not wanting to be discovered by her sons, she returned to the ladies room to repair the damage to her clothes, while Tim used his visit to the locker-room to bring himself to orgasm, all the time remembering what he had seen.

Jean returned to her desk and spent the next two hours in the office trying to concentrate on her work. Eventually, she was forced to accept the fact that she wasn’t accomplishing anything. Her mind kept wandering back to what had occurred earlier. Locking the office, she entered the gym where she was met by the enthusiastic reports of how much fun her children were having. Both Tim and she acted as if neither had been aware of the other. Since it was almost lunchtime, Jean suggested Tim join them in the cafeteria and he willingly accepted.

During lunch, she questioned him in such a manner, that he revealed personal information about himself without being aware of how much he was openly divulging. She grasped his problems with his father, inferred his emotional attachment to his mother and now understood why he was so sensitive towards women. Halfway through lunch, they were joined by her boss, the Commandant of the Military Academy. In the conversation, she explained how they had met and how Tim was graciously watching her two boys while she worked. Jean explained her on-going problem of finding a qualified sitter and asked her boss if she could avail herself of Tim’s services on a semi-regular basis. That is, whenever she couldn’t find a sitter, could Tim watch the boys at her house?

After further discussion, his complete approval was given. He even approved Tim, if necessary, being allowed to sleep over if she had a late date. Lying, she explained that this was the exact case tonight and her boss directed Tim to pack a bag and sign out into Jean’s care. After lunch, Jean returned to work, while Tim went back to watching the kids. She "buzzed" through the mound of paper in record time.

Making sure she was alone, she called her older sister Susan and asked if she would "take" her nephews to a movie that night. After Susan agreed, Jean hinted that she might have a male visitor at which point her sister offered to keep the boys overnight. Jean then went into a thorough explanation about Tim. She told her sister she had been so happy to get her boss’s permission for Tim to baby-sit that she hadn’t realized the complication his being there might cause. If he spoke out of turn, about her male visitor, back at the school, her job might be in jeopardy. She suggested that Susan not bring up her keeping the boys overnight and later, act as if the idea was a last minute decision based upon the lateness of the movie. Susan readily agreed.

With her plans set in motion, she locked the office, found the three boys, waited for Tim to pack and then drove to her house. During the drive, she allowed her skirt to rise above the tops of her nylons and felt rewarded by the bulge that grew in Tim’s uniform pants. After dinner, Susan showed up, asked to take Jeff and John to a movie saying nothing about their staying over. When Susan, on the side, asked her sister about Tim, Jean said she would return him to the school when she left for her date, explaining to The Commandant she wouldn’t be out as late as she had originally anticipated. Susan wished her well, kissed her cheek and left with her nephews. Jean asked Tim if he minded being left alone until the boys came home while she was out.

Tim, realized he would be alone in the woman’s house for hours and as it had been a long time since he had the chance to play in panties, nylons or a slip, seized upon the opportunity and readily agreed to stay and wait for the boy’s return. Jean cautioned him not to say anything to her boss about the change of plans, as he might not understand. Tim noted her concern and promised he wouldn’t say a word about the change. Jean suggested he watch TV while she went and prepared for her date, which is precisely what he did.

Leaving him alone Jean went to her room and changed into the sexiest outfit she owned. The dress was backless, made of polyester wool crepe, dyed black and did nothing to hide her charms. Under it she wore a black garterbelt, black sheer nylons and French cut, black sheer panties and no bra. Finishing off the effect she wore 3" black patent leather heels. Looking at herself in the mirror, she knew the reaction she would get from the young boy.

When Jean entered the den, supposedly to give Tim some final instructions, she was rewarded by the look of desire in the youth’s eyes. He could barely mumble his understanding as he riveted his attention to the exposed roundness and the tanned cleavage of her breasts.

When she spun around to leave, a low gasp of youthful appreciation escaped from between Tim’s lips. Jean’s low-cut dress had exposed her nude back and the obvious fact she had no tan lines. It had not escaped Tim’s attention that Jean must sunbathe in the nude.

"Why thank you for that reaction. Now I hope I get the same from my date. Do you really like the way I’m dressed? It’s not too revealing is it? Maybe I should change? You don’t think I’m too old to run around dressed like this?" She coyishly asked.

Assuring her she looked fantastic, Tim unsuccessfully attempted to hide the growing bulge in his pants.

Pointing at his erection, Jean exclaimed. "Oh, I must really look good if I can cause that much of a reaction from a young boy!

Tim lowered his head, truly embarrassed and began to apologize.

Jean grasped his hand and said, "Tim, let’s sit down on the couch for a minute and talk."

As they sat down, she stated. "There’s no need to be embarrassed, women dress this way on purpose. We do it to get men’s attention and excite them. Why should you expect to be immune, afterall you’re not that much younger than I am! If I didn’t obtain a reaction from you I’d be disappointed. A woman likes to know that men think she’s sexy, or we wouldn’t go through all the trouble to look this way. The type of clothes we wear causes women to accidentally expose their bodies to men’s perusal everyday of our lives. Think about it, every time we sit down on a chair and cross our legs, we expose at least our thighs. Getting up, if we’re not especially careful, allows men to see up our skirts all the way to our panties. Women have become accustomed to daily exposures of their bodies so we use it to our best advantage. Most men don’t realize we do it on purpose! We dress to tease men! A man’s vivid imagination is a woman’s greatest weapon in the war between the sexes. It gives us power over men. Almost every man I’ve ever met will ‘break his neck’ to see up my skirt. Sometimes I purposely let someone I really like look up my legs...like I let you this morning."

Tim exclaimed. "You knew that I was looking up your skirt? Does that mean you really like me?"

"Of course I like you, I like you a lot! I think you’re very sweet! What happened today, started out as an accident. I was checking on the boys, but didn’t want you to think I was checking up on you. When I stepped out on the landing I had no intention of even being seen. When you looked up and discovered me, I felt I might have hurt your feelings. Then, when I realized where your eyes were looking, it pleased me that you weren’t upset with me and that you liked what you saw. I want to be honest with you, if you’ll be honest with me? How about it?"

Tim, afraid his voice would crack, nodded his agreement and Jean continued.

"Having you look up my skirt excited me! That’s why I spread my thighs so you could see even better. I wanted you to see more of me! I knew the effect I was having on you. It didn’t matter how much you saw. We certainly weren’t hurting anyone. What started out as just another accidental exposure, turned into two people enjoying the situation. I got just as excited as you did. Tim, as you grow older, you’ll find most women enjoy being teases. A woman who’s comfortable with her body isn’t afraid to expose herself when the situation suits her. Maybe I shouldn’t be telling you all our female secrets or maybe it’s time you told me a few of yours. I know you got hard and then ran off to the john. Did you play with yourself? Did you come?"

"Yes. I couldn’t help it. I almost didn’t make it! When I got there I couldn’t believe how hard my dick was. Oh! I’m sorry, I shouldn’t have said that word."

"Tim, it’s OK. You don’t shock me, I’m an adult woman who has two kids. Honey, I definitely know what a dick is. How do you think I had those kids? Did you think of me and my panties when you played with your dick?"

"Yes!" Smiling sheepishly as he answered.

"Good, I’m glad, that makes me feel even better that my accidental exposure wasn’t wasted."

Kissing him on the cheek and then rising, she said. "Well, I’ve got to get going. If you get hungry, help yourself. I’ll probably be late, so don’t think you have to wait up."

Tim, hoping to get another look up her short dress, walked Jean to the car and held her hand as she climbed behind the wheel of her Camaro. He was rewarded, with another "accidental" exposure, as Jean dropped onto the low seat, pausing with one leg in the car and the other still on the ground. Her short skirt sliding back past the tops of her nylons thereby again exposing her panty covered crotch to the youth’s eyes.

Thanking him for the helping hand, she commented. "That nice new bulge in your pants tells me I must have had another accidental exposure." Giggling, with a twinkle in her eye she smiled up at him and said. "I really must learn to be more careful! If I keep having these ‘accidents’ you might start thinking I’m doing it on purpose and you know I wouldn’t ever do that!" she giggled.

Then lifting her other leg in such an exaggerated motion that she totally exposed her panty covered crotch, while at the same time running her tongue across her moist lips, she closed the door, and drove off.

Watching her drive away, all he could think was "WOW, what a sexy woman!"

He returned to the family room, tensely waited about 15 minutes and then headed for Jean’s bedroom. He stood in the doorway and peeked inside. The clothes Jean had worn earlier were strewn about the floor and bed. So were several outfits that had apparently failed to make the cut. Stepping into the room, he immediately detected a hint of make-up, perfume and hair spray in the air. The room smelled so sexy, so sweet, and so delightfully feminine he felt his cock rising!

Tim moved to the pile of clothes Jean had worn earlier that day and now lay discarded on the floor. Using the tip of his shoe to push aside the skirt, he uncovered her lingerie, including the tiny bikini panties he had seen earlier that day covering her pussy and ass. Bending over, he picked them up, brought them to his nose and inhaled deeply. The musky woman’s scent permeated his senses. Placing them on the bed, he went to Jean’s open dresser drawer. Inside were three neatly folded piles of panties. The styles ranged from tiny, sexy bikinis, more conservative hip-huggers and finally even more conservative brief style panties, the kind he and his mother usually wore.

He carefully pulled a second drawer open and looked down at an array of bras, slips and camisoles. The third drawer displayed hose, both panty style and nylons along with the garterbelts to hold them up. The belts were much more feminine than those of his mother’s. These had lacy little straps of elastic with bows on them and came in assorted pastels and rich colored reds and blacks. He pulled the last drawer open and found Jean’s nightgowns. Running his hand through the silky material he tried to imagine Jean in the more revealing ones.

Meanwhile, Jean had driven around the block, parked her car in a secluded spot and smoked a cigarette. Wanting to rush back home, she forced herself to wait, knowing any young boy as sensitive as Tim would hesitate before he began to snoop. Not really knowing what he would do, but guessing he would at least go through her lingerie drawers, she wanted to catch him "red-handed". Holding the threat of exposure over him would guarantee the youth’s total obedience. When she could no longer wait, she crossed through a neighbor’s yard and snuck up on her bedroom window. Before leaving for her supposed date, she had left the window slightly open. Using a long handled comb she quietly pushed the shade aside and saw Tim standing before the opened drawers of her dresser. Mentally congratulating herself on the success of her plot, she began to turn away to sneak into the house to confront the youth. At the last moment she changed her mind. Out of the corner of her eye she had observed Tim beginning to undress. Not wanting to miss this, she again positioned herself under the window.

Inside, Tim quickly removed all his clothing. Standing before the full-size mirror he stroked his cock and balls with Jean’s discarded slip while inhaling the scent from her panties. His hand pounded his male organ as he furiously jacked-off. He was ready to spurt his hot cum across the bedroom carpet when he realized the mess that would be caused by the blobs of sticky cum. Rushing to the adjacent bathroom, out of Jean’s sight...he climaxed into the toilet. Then using some tissues, he cleaned himself, making sure he squeezed every last drop out of his now softening organ.

Jean, who felt cheated, rushed to the back door, quietly let herself in, snuck into the bedroom and hid in her walk-in closet. All this occurred while Tim was cleaning himself. Her intention was to surprise Tim as he returned from the bathroom. She again changed her mind when he returned carrying additional articles of her clothing, obviously taken from the hamper. She didn’t know what purpose they would serve, but hoped another demonstration would be forthcoming. Afterall he was a young boy and was probably ready to come again. What she couldn’t understand was why he was carrying her strawberry blond wig in one hand. She decided to take a wait and see attitude.

Tim lovingly laid out all the finery across Jean’s bed, then picking up an emerald green garterbelt, he put it around his boyish waist, connected the clip, spun it around so the fastener was in back with the garters dangling against his thighs. Then sitting on the bed he carefully rolled a pair of sheer, black nylons up his legs and expertly attached them to the garters. Lifting one leg, he provocatively ran his fingertips over the sleek nylon, removing any looseness or sags. Doing the same to the other leg, she heard him say.

"Boy, I sure wish I could wear these every day!"

Rising, he carefully straightened the hose and expertly adjusted the straps for a better fit. Stepping into the matching emerald green satin-like panties, he slithered them up his legs, past the garters and shimmied his ass into the delightfully cool material. Pausing to accommodate his semi-turgid penis back between his legs, he reached for the bra lying on the bed.

By this time, Jean realized Tim was a crossdresser and a very adept one at that. He even exhibited the mannerisms of the feminine gender. Obviously, she mused, he had been coached, probably by his mother or some other woman!

Jean, as she watched, used her free hand to stroke her nipples through her dress. This was even better than she could have hoped. Now, with this knowledge, he would have to obey her every whim. As she observed Tim feminize himself she became more and more interested, more and more excited and less and less concerned with the power she originally wanted over him. Now she desired him as a lover and not as a "plaything". Jean had always had a hidden desire to lie with another woman, but had been afraid to take the first step. In fact, it was rumored one of the secretaries at the office was gay and Jean had pictured the woman in her fantasies. However, not being brave enough to approach her, she now found herself with a solution to her craving.

Raising her skirt, she slid the crotch of her panties aside, exposing her womanhood and began to gently stroke her tunnel of lust. Inserting two fingers deep inside herself, she used her other hand to masturbate the blood-engorged bud of her clit. Mentally she warned herself against losing control or emitting any sound of passion that might cause her to be discovered. Her mind reeling from the sensuousness of what was being enacted before her eyes she decided she preferred the direction towards which the bedroom scene was moving versus her initial plan of control over the youth.

Tim, unaware of Jean’s presence, had finished crossdressing. He had chosen an off-white blouse with ruffles running down the front and a black straight skirt that zippered and buttoned on the side. The skirt was a bit long, as the hemline fell past his knees, but he had chosen it because it highlighted the round globes of his ass and the slit up the side displayed his nylon clad thighs to their fullest. Standing before the mirror he bent forward and placed the blonde wig upon his head. Adjusting it by running his fingers through the strands he stood there satisfied with his appearance. Oh, he knew he needed make-up, jewelry and heels but he wasn’t sure if he had the time for make-up and the rest could be obtained easily enough. He relished the titillating feelings racing through his body. This was the first time since leaving home he felt gender correct. He realized, Jean’s lingerie was even more satisfying than his mom’s was. Also, dressing in the clothes of a woman who was a stranger increased the sensuousness he felt.

Turning, he noticed Jean’s jewelry box sitting on the dresser. He walked over to it, reveling in the feel and sound as his nylon covered thighs rubbed against each other. Tim opened the box and found a perfectly wonderful pair of gold and red enamel clip-on earrings. After attaching them to his earlobes, he decided he really needed heels and proceeded towards the closet.

Jean, seeing where he was headed and realizing the probable reason why, pulled her fingers from inside her pussy, dropped her skirt, grasped a pair of heels and pulled the door open just as Tim reached for the handle.

"Are these what your looking for, Tammi?"

Tim was stunned. The shock caused an immediate reaction in his panties. The blood rushed from his dick to his face, causing his member to shrink and his cheeks to blush. He was caught! Now his mind raced from one consequence to the next. Not only would he be thrown out of school, but also his crossdressing would be exposed to his father. Knowing his father’s punishment would certainly be painful, he also realized his mother’s involvement might be exposed. He couldn’t let that happen, he loved her too much! Maybe he could convince Jean not to say anything. Before he could beg, she spoke.

"Tammi, why don’t we sit on the bed and have another little talk. Just us two ‘girls’. How about it, sweetie, would you like that?"

Confused by Jean’s attitude, but afraid to refuse the woman, Tim nodded his head as he fought to hold back the tears. Jean took his hand and led him to the bed where she directed him to sit on the edge. Sitting next to him at an angle, she slid her right ankle under her left knee. He immediately noticed the space this opened between her thighs, again exposing the welt of her nylons. Even though he was scared, he still couldn’t help himself and openly stared at the woman’s firm fleshy thighs.

"Do you like what you see? Good, you’re supposed to! I told you women use the way they sit to tease men, its a way of getting power over them. Can you feel the power I have over you? If I opened my legs just a bit wider, wouldn’t you do almost anything I asked? Of course, you’re going to agree to anything I want anyway, aren’t you? Otherwise I’ll be forced to call the school and tell them about all this. I can just imagine what the Commandant and the other boys would say about you wearing my panties and my bra. I can also guess what your father would say about nylons and a garterbelt. Is that what you want me to do?"

The look on his face told her the answers to her questions without any verbal response. He definitely desired her silence and would do anything to earn her cooperation.

"Tammi, that’s going to be your new name whenever you’re dressed this way, but before we go any further, you’ll have to tell me everything you know about girls and/or women. I also want to know everything about your crossdressing. I want to know how you got started, how often you dress-up and who taught you feminine mannerisms? I know you couldn’t become so adept at wearing women’s clothes without some expert help. I must have your total obedience and you must be totally truthful. If I catch you lying or hiding the smallest bit of information from me...we’ll stop and I’ll take you back to the school dressed in my clothes and tell the Commandant what occurred here tonight. I’m sure you don’t want that, do you?"

"No, please don’t do that!" He begged.

"Good! Now that you thoroughly understand the control I have over you we can continue our "girl-talk". If you accept my terms and I don’t see that you have any choice, I’ll let you continue to come to my house, dress in my clothes and I’ll even teach you more about being a girl. There will be other exciting things we can do together dressed as girls, things I’m sure you’ll enjoy. All I’ve said can be yours if you agree to my terms. Well?"

"Yes, I’ll obey your every request and tell you everything."

Now guaranteed of his complete obedience she told him to begin.

As the story of his crossdressing, his desire to have been born a female and his emotional attraction to his mother unfolded, Jean found herself becoming aroused. The sexual heat she had experience earlier began to build again. Asking questions, she determined he was a virgin, but definitely knowledgeable about the ways of sex. It was obvious his mother had explained quite a lot. He admitted he had never seen a woman naked, not even his mother. Girlie magazines, his mother purchased for him were his only knowledge of nudes.

When he was all finished, he asked. "What are you going to do to me? Should I start taking off these clothes? What about your date and when will the boys be back?"

"Oh, those are my other surprises. I don’t have a date and the boys are going to sleep over at my sister’s. When I saw you staring up my skirt today, I knew there was something special about you and made up the whole story about a date. I also called my sister and made all the arrangements for us to be alone the entire night. As for the clothes, wouldn’t you rather leave them on for now?"

"Yes, the only time I’m really happy is when I’m a female!"

"Maybe I shouldn’t be telling you this. I like the way you look in my clothes. Of course you need make-up but even so you make a very sweet young lady."

"Jean, if you keep my secret, I promise I’ll do anything you ask!"

Taking him in her arms, she kissed him. Then forcing his lips apart with her tongue, she taught him the nuances of "French" kissing.

When they separated, he asked her in his best Tammi voice. "Are you going to introduce me to lesbian love?"

"Yes," she answered. "Before the night is over I plan to teach you all there is to know about two women making love. I don’t want you to hold back or be afraid to touch me, but you will listen to my guidance."

Reaching out to each other, they began to kiss in earnest. As their emotions rose, Jean moved her fingers to Tammi’s ruffled blouse. Unbuttoning it, she reached inside the cups of his bra, smiling to herself as she discovered the bunched nylons he had used to simulate female breasts. Slipping the straps off Tammi’s shoulders she reached behind his back to release the catches. Cupping her right hand, she stroked his hairless chest as if he had real tits. Both were amazed at the puffiness that rose from his chest muscles to fill her cupped hand. The nipples elongated, actually reaching the size she remembered when her own breasts began to bloom. In addition, they exhibited the sensitivity of female nipples. Jean thought to herself. "Maybe he should have been born a female, he certainly reacts like I did when I was his age!"

Using her tongue, she licked, nipped and sucked each ridged nubbin of flesh. Tammi’s reaction was a series of soft mewing moans as he twisted his chest to obtain the greatest pleasure from Jean’s playful teasing. Realizing he was getting too excited, much too soon, she broke away and said.

"Use what you’ve just learned to please me. Always remember, a woman’s body is to be adored, there is no place for roughness, at least until she’s ready to orgasm."

Tim began his seduction by licking and kissing her neck and ears. Gently, he stroked her bare shoulders and back. Tim slid his hand to her breast and as gentle as a soft whisper stroked the rising nipple through the dress material. Gaining confidence, he gently laid her down across the bed, untied the neck of the dress behind her head and slowly dragged the material down to her waist, leaving her upper torso bare.

Jean looked into her young lover’s eyes, saw the amazement reflected within them and smiled up to him. A warm tender glow began to build within her soul. This was no longer just sex, she realized, this was a budding love affair. Cupping one of her tender breasts, she raised it to his lips, moaning as his warm breath fell across the pouting nipple. Tim took her offering and lovingly licked and suckled as he had been shown. Using his hands, he stroked and fondled her neck, shoulders, back, stomach and especially Jean’s other breast. He learned what pleased her and that’s where he concentrated his efforts. Every boy dreams of learning the act of love from an experienced older woman and he was one of the lucky few whose dream was coming true. When Jean pulled the nipple away, he knew to concentrate on the other breast.

Jean lay back and basked in the pleasure her youthful lover was providing her. For a first timer, he was more than adequate, he was actually adept. As his confidence rose, her need to be in control lessened. This scared her.

"That’s enough of that for now! Stand up and undress me!" she roughly ordered.

Tim obeyed immediately. He rose and then in a surprise and gallant move, offered his hand to assist Jean in rising. This attention was not lost on her. Where a moment before she had been concerned, no actually scared about controlling his level of obedience, this sensitive gesture quickly erased all fear. Now she could let herself go and if the need to take charge ever arose, she knew it was only for the taking. Tim was too tractable to ever cross her.

Meanwhile, Tim had continued to tease her tits with both his fingers and his wet tongue. Turning her back and leaning against him, she said.

"You did that very well! Now show me how you think two women would make love. Don’t worry, I’ll help you when you need it."

Tim’s fantasies about lesbian love-play had prepared him well. Reaching up, he lifted the hair from her neck and "nuzzled" and kissed the short hair he found there. This caused Jean instant pleasure and subsequent "goosebumps". As she shuddered in delight, she felt his kisses move across her bare shoulders, down her spine and only stop when he reached the last exposed inch of skin at her waist. Grasping the zipper, Tim slowly pulled, enjoying the view as the dress parted before his lusting eyes.

Jean’s panty covered cheeks displayed their fullness. Then when she "shimmied" her hips, the dress gently floated to her ankles. The sound of his surprised gasp of appreciation brought a glow of pride to the woman’s features. There the sexy young woman stood, naked to the waist, her garterbelt and nylons framing her panty-covered ass and her smooth, sleek thighs. Bending forward at the waist to teasingly straighten her hose, she was again surprised when Tim knelt down behind her, hugged her around the middle and ran his face across her asscheeks. Remaining in the position she spread her thighs even wider, thereby encouraging him to continue his sensual adoration. Tim used his stiff tongue to run the crevice between her cheeks. When he discovered the exact location of her pucker hole, he jabbed his tongue hard up against it. The moan of pleasure from Jean encouraged him to continue.

Sliding and twisting backwards through her legs, Tim licked and kissed her panty-covered crotch. Looking upward between her soft thighs, he noticed how her swollen pussy lips had spread open inside her sheer panties, their outline in the now damp almost see-through material plainly evident. Jean, realizing what his next move would be and not yet emotionally ready to have her pussy licked...stepped away from the youth. Turning and sitting down at the bed’s edge, she said.

"Tammi, why don’t you slip out of that skirt and show me what else two girls in love can do with each other!"

Quickly stepping out of the skirt, he caught Jean looking at the bulge in his panties. Not wishing to destroy the image of two lesbians making love, he adjusted his dick back between his legs, then knelt down before his lover’s knees. Gently grasping her left ankle he planted a firm kiss on the exposed upper arch. As he kissed and licked his way up her nylon clad legs his eyes never wandered from the slit of black, sheer, silk covering her musky scented womanhood. Upon reaching her naked thighs he continued his kisses, sliding his hands up under her tush. Squeezing the firm muscles, he inched his lips ever forward.

Jean’s mounting passion finally manifest itself by her grasping his ears and pulling his face against her panty covered pussy. She knew her need was now too demanding to curtail. Twisting his head, back and forth against her panty covered clitoris caused enough pressure to set her off...and she doused her panties with her juices. Jean’s strong orgasm excited the youth and he dove forward, causing a second series of sensual shockwaves to course through the young woman’s throbbing lips of lust. As her vibrations slowed, Tim licked and sucked the sweet emissions through the material as moans of sexual satisfaction slipped from between the woman’s lips.

Jean lay back basking in the warm afterglow of her two orgasms. Tim knew that Jean had come and suspected it had been a multiple climax. Realizing she needed to rest, he slid next to her on the bed. Ever so gently, he ran his fingertips up and over every sensuous curve of her delightfully luscious body, being extra careful not to arouse the woman’s passions any further.

Snuggling up to her ear and in his best Tammi voice, he made verbal love to her. Recalling to his lover how excited Tammi had gotten from their mutual girl-play. Telling her about the flood of erotic sensations that had assailed Tammi’s breasts and sopping wet "cunni". This whispered fantasy re-creation brought joy to Jean’s face and an understanding of their new relationship. Jean’s initial desires had been brought about by pure lust, now that lust was replaced by feelings of tenderness for the young boy/girl resting his body beside her. Obviously some of her initial plans needed reconsideration. Maybe she should "talk" to his mother.

"Tammi, remember your promise to tell me everything?"

"Yes," he answered.

"How would your mother feel about you spending some of your weekends at my house?" she asked.

Tim, not knowing where she was headed with the question, asked. "What do you mean?"

Jean spent the next half hour discussing her ideas with him. When she finished it was agreed that she would write a letter, on school letterhead, inviting "mom" to attend a Mother’s Tea and weekend visit. The invitation would explain that those invited women who lived far away were being offered lodging at the homes of female employees of the school. Jean had selected Tim’s mother since her son was familiar to her. In the letter, Jean would explain how she had met Tim and how he was "sitting" for her kids.

Tim encouraged her to hint there was more to their relationship. He suggested Jean comment on how much help Tim was in selecting outfits for her to wear and how they had gone clothes shopping together. He felt these hints would insure his mother’s attendance. Tim was also to telephone his mother and if necessary also drop small hints. Tim felt sure she would accept, if only to get a weekend away from her abusive husband. After his "mom" arrived, they would explain the real reason...his need to crossdress. Depending how well "mom" reacted, they would explain everything. If his mother received this in a positive manner, the three "women" could come up with a plausible scheme that would satisfy both the administration and "mom’s" husband. Their plans complete, they resumed their love-play.

Jean now decided that it was time he lost his female virginity. Removing her panties and gently cleaning her pussy lips with a warm washcloth, she proceeded to explain the inner workings of the female sex organs. Spreading the puffy outer lips of her pussy she tutored him as to how women satisfy each other with their flicking tongues and fingers. Stroking the bright red bud of her still swollen clitoris she explained it was as sensitive as the crown of his penis and must be approached with gentleness.

"I’ll show you what I mean!" she said.

Reaching between Tammi’s legs, she gently massaged Tim’s cock and balls still encased in their satin pouch. Within seconds he was ready. Slipping the panties over his hard-on, Jean stretched the elastic behind and under Tim’s balls. This caused his male organ to stand straight out from Tammi’s sparsely haired pubic bone. Cupping the sack, she teased the sensitive area behind it with her nails. Licking her lips, Jean lowered them to the purple tip of Tammi’s pulsing penis. Parting her moist lips she engulfed his entire crown. With a slow, twisting motion and a swirling tongue, she sucked her way back to the tip.

Tim couldn’t believe the sensations Jean’s mouth was causing. He had never gotten this excited, this quickly. He knew he couldn’t take much more of her licking and sucking. When he felt his balls "tighten up" and the jism rise he tried to pull away, afraid he would upset Jean by shooting off in her mouth. Jean’s lips however wouldn’t let go. Her jaw muscles held him tightly as she pulled the cheeks of his ass forward with her hands. As she increased her strokes, she felt his organ momentarily swell and then spasm in her mouth. Using her cheek muscles to suck out every drop, she swallowed every last spurt. Using her tongue, she then licked the excess that had run down his shaft, hoarding it in her mouth she "French-kissed" him. Tim tasted his own salty warm fluid and was shocked to find out he enjoyed the experience.

Rising, Jean left the bed area and went to the linen closet in the master bath. Fishing behind some sheets, on the top shelf, she found the large strap-on dildo she had hidden there. She had purchased it, just recently, in the hope that the dildoe’s size would resolve her masturbation problem. While she hadn’t really needed the strap-on device, that’s the way it came. Slipping it on, she inserted the rubber cock through the opening from behind and positioned it so it "rode" against her clit. Grabbing a jar of Vaseline jelly from her vanity, she returned to the bedroom.

Tim had assumed Jean had left to use the john. He had spent the time she was absent, basking in his own afterglow. When he saw Jean emerge from the bathroom, with the huge swinging dildo at her crotch, he was scared and confused. He hopefully asked. "Are you going to teach me how to suck a cock? It’s not necessary, I’m only turned on by women!"

"No!" she leered down at the youth. "Tammi, I’m going to make you a real woman, I’m going to take your virginity. You can’t be a real girl until you’ve felt a cock inside your ‘pussy’!"

Immediately guessing what Jean had in mind and in fear of the dildoes size, he began to object. Then remembering his promise to completely obey the woman, he resigned himself to being "fucked".

Jean had him assume the subservient position of leaning on his elbows and knees. His firm cheeks naturally spread for easy penetration. Then lathering both the dildo and two fingers of her hand she worked the lubricant around the squinting eye of his tush. Using first one finger and then a second, she coated the inner walls of his anal tract.

Tim for his part, found he was enjoying Jean’s fingers slithering up his ass. Surprised by the sensations that coursed through his genitals, he was getting semi-hard. Jean told him to relax his sphincter muscle and he found the finger fucking even more pleasant. When Jean felt he was fully primed she positioned the dildoes bulbous head at the pouting entrance and surprising him, pushed the crown portion into his surrogate pussy. Tim let out a loud piercing scream of abject pain and tried to pull away. Jean, anticipating his reaction, fell forward, using her weight and position to overpower his attempts to escape. Firmly holding him down, she seductively whispered in his ear.

"Tammi, all women suffer pain the first time their cunnies are violated. It’s part of being a woman. Just relax and the pain will go away. Be thankful I care for you, most girls are less lubricated their first time and suffer more than you."

As the pain was already beginning to subside, Tammi relaxed even more and was reassured when the pain was replaced by a pleasant full feeling. Jean, aware of his condition, slowly began to inch more and more of the rubber phallus inside him. When she had all eight inches up his "pussy" she began fucking him in earnest.

"Reach under yourself and stroke your "clitty", sweetie. When you get ready to come, stop and let me know."

Tammi felt the passions building in his groin. Closing his eyes, she imagined she was on a date in the back seat of a car. She had allowed the boy to get her overly excited, had lost total control of the situation and was now being penetrated for the first time. The fact he still wore the garterbelt and hose helped his imagination "picture" the scene. Reacting to the fantasy, she began to push her "pussy" back to meet her male lover. Tim had always wondered what it felt like to be penetrated like a woman. Now he knew...it was wonderful! Aware he was quickly approaching orgasm, he opened his eyes and informed Jean.

"I’m about ready to come!"

Jean gave one more inward stroke, then pulled the dildo out with a loud sucking sound. Flipping Tammi on her back, she raised his nylon-clad legs high into the air and re-inserted the dildo in Tammi’s "cunt". Spitting into her hand, she reached forward and grasped Tammi’s swinging cock, encircling the crown between her middle finger and thumb. Then matching the thrusts of her hips to the twisting motion of her hand, she pounded Tammi’s pussy with her false cock while she jerked him off.

The sensations "rolled" between Tammi’s cock and "pussy". She felt the inner muscles of her "cunt" grasping at the dildo with each outward stroke, trying to keep it from leaving and then spreading wide to meet the "boy’s" hardness as it again forced entrance into the channel of her womanhood. No longer wishing to hold back...Tammi came. Her cum exploding in graceful arcs landing on both their bodies. Some even splattered their faces.

Jean also achieved orgasm brought about by the direct pressure of trusting the dildo into her "lesbian" lover’s "pussy". Exhausted, she pulled out and fell across her newfound lover. Reaching their moist lips to each other, they gently kissed and licked the spent juices from each other’s features, giggling as young girls are prone to do when they have a secret.

"Now you know how it feels to be a woman! Did you like it?"

"Oh, it was wonderful, everything I fantasized it would be! But it was only ‘good’ because it was you taking my ‘cherry’! Jean, I love you! I wish I could be your lesbian lover and live with you all the time!"

Jean thought a moment, then said. "After we see how it goes when your mother visits, maybe we can work something like that out between us. I’d love to have a girlfriend like you. Let me think about it. Now I think it’s time we removed these clothes, cleaned ourselves up, got into some sexy nighties and went to sleep. We need some rest before my sons come home tomorrow."

They did exactly that, giggling and playing with each other as they cleaned up. Cuddling up next to each other, like two spoons in a drawer, they fell asleep.

Somewhere in the middle of the night, Tim awoke to the warm realization he was being fondled. Pretending he was still asleep, he peeped between his lashes and found Jean was slowly moving her hand across his panty covered ass. Deciding to "see" what Jean was up to, he continued to feign sleep.

Jean had awakened, from a sensual dream and looked over at her young lover’s body. Remembering what had transpired earlier, she felt desire again building within her. Realizing she still hadn’t "taken" his male virginity, nor had she been "fucked", she slid her hand to his satin covered ass. Not knowing if he could perform yet, she rationalized he could at least satisfy her again with his tongue. Moving her hand under Tammi’s baby dolls, teasingly up his stomach, she encountered his nipple. Stroking the tip, she was again amazed how hard it became. Lightly pinching it brought mewing sounds from the youth’s lips. Assuming he was still asleep, Jean pulled her hand from under the nighty and gently slipped it under the elastic of his panties. Finding his penis fully erect, Jean surmised Tim was faking. Delighted to find him restored, she however, was not going to let Tim get away with his deceit. Cupping her hand around his sack, she began to gently but firmly squeeze his balls. She laughed as she spoke.

"When you decide to stop faking, beg me to release your jewels and offer me something ‘nice’, I’ll stop, but not before I get your promise."

Not in any real pain, yet, he answered. "If you let go of my nuts I’ll promise to eat your pussy."

"Without my panties on?" She asked, exerting more pressure.

"Yes! Yes! Only stop your squeezing!"

Releasing him, Jean ordered him to remove his nighty and panties. As he complied, she removed hers and stretched out across the bed with her arms above her head. Bending her knees and letting them fall naturally open, she exposed her total womanhood.

Tim lay down and positioned his head above her pussy. Placing his hands under her tush he raised her pelvic area to his moist lips. Gently kissing and licking her outer lips he used his tongue to open the inner ones. Now darting his tongue into her cunt, he "flicked" the inner walls.

"Oh! Oh! Yes! Fuck my pussy. Stick that hard tongue all the way inside. Oh, that feels good! Don’t stop!"

Tim "bounced" his head between her open lips, mashing his nose against her clit. When he felt her thighs quivering against his ears...he did stop. Letting Jean’s desires coast to where she could catch her breath, he again moved his face up to her oozing cunni. Using his fingers to hold her open, he teased the blood-engorged bud of her clitoris with his tongue. Kissing and licking, in teasing circles, he felt the muscles of her legs again tighten. Increasing the flicks caused Jean to throw her legs up over his shoulders, locking her ankles behind his head and thrusting her hips upward to meet him.

"Yes! There! Yes, there! Faster, oh yes, there and there! Now harder. Harder! Yes! Yes! Oh! I’m coming! AAAAAAIIIIEEEEEE!"

Jean came and came and came. The burning sensation raced through every erogenous nerve ending. Her arms flailed the bed as her head trashed from side to side. She squeezed her thighs so hard, Tim almost passed out. When the pain-like throbs finally stopped running amok, she collapsed. Tim watched as she slithered and rubbed herself against the sheets in an effort to "milk" every last tactile sensation from her body. Lying beside her, he gently "munched" and kissed her lips, cheek and the tip of her nose until she was able to speak.

"I’ve never experienced an orgasm so strong. It’s never been that good for me! I’m a little embarrassed by my performance. Oh, but thank you, it was wonderful."

Tim, leaning on one elbow, smiled, then bending down, he kissed her. A kiss of love...not passion. Jean recognized the kiss for what it was, threw her arms around his neck and returned his love.

"I woke up with the intention of making love to you. Instead you satisfied me. I should spank your ass for feigning sleep, but the way I feel, I just don’t have the energy"

"Does that mean you’re too tired to make love?" He asked forlornly.

"Aha! I got you. How does it feel to be tricked by your lover?" She laughingly asked.

"You mean we can?" His voice rising.

"Yes, of course we can. Women don’t need to regenerate like men do. All we need is a few moments to let our emotions return to normal. Let’s go get something to drink and a cigarette and then we’ll see what happens."

Each slipped on their nightgowns and a pair of fuzzy high-heeled mules and then Tim followed Jean downstairs to the kitchen. Opening two cans of diet coke, Jean put them on the table and sat down on Tim’s lap. Squirming her bottom against his limp penis and throwing one arm around him she teased his earlobe between her lips.

"Aren’t you glad you offered to be my kids baby-sitter?" She laughed.

Tim slipped his hand under her top and cupped her heavy breasts. Jean warned him not to play too seriously or she would never make it up the stairs. She realized the unique attraction her breasts were to the youth. When she felt he had played enough, she slipped off his lap and sat on one of the kitchen chairs. Lighting a cigarette, she spent the next 30 minutes asking him additional questions about himself and his mother.

Putting out her second cigarette, she stood up, took his hands in hers and pulled him up against her lush body.

"Tim, darling, why don’t you take me to your room and fuck me! I want to feel that huge cock of yours pounding inside my cunt."

Realizing the tack she wanted him to take, he said. "Not before you suck my dick!"

Squealing in false terror, she broke out of his grasp and ran up the stairs, with Tim close behind. He caught her halfway up, raised her nighty and playfully "smacked" her across her panty-clad bottom. Her false scream of protest earned her a second swat, this one just a bit harder. Running to get away from a third, she stopped at the doorway to her room, paused, pulled down her panties and "flounced" her naked ass. Before he could react, she ran and jumped onto the still warm bed. Stripping naked as he climbed the remaining stairs, Tim entered the room...as a male.

Jean took one look at the dick in his hand, scooted over to the edge of the bed and began to draw it into her warm, wet mouth. She could tell it wouldn’t take very long to get the youth primed. His legs were already shaking with desire as she swirled her tongue over and around his male organ. When he began to thrust forward as if fucking her mouth, she stopped and fell spread-eagled across the bed.

"You need to calm down a bit. Eat me again. It will get me slippery and wet. That way you’ll be able to enter me easier and last longer."

Within three minutes Jean was herself too aroused from his cunt-lapping to wait. Pulling his face from between her outstretched thighs, she dragged him on top and guided his dick inside her demanding cunt.

The warm, wet walls of her womanhood enveloped his young manhood. Nothing he had ever experienced before this moment had prepared him for the sensation of being inside a woman. Not wanting the feelings coursing through his groin to ever stop, he lay there without movement.

Jean, surprisingly ready again, understood his lack of movement, but would not be denied and took matters into her "hands". She ever so slowly backed her pelvis away from Tim, drawing his cock almost all the way out of her tunnel of desire. A strong shudder racked her lover’s body. She whispered.

"Don’t hold back, I’m as ready as you are, go for it."

Tim thrust forward with the power of a piston. Slamming his balls against her ass, crying out in a mixture of sensual pain and abject pleasure. Pulling back, then thrusting again, he was met by Jean’s upward stroke. No longer in control, they both went into a frenzy of stroke and counterstroke. Tim, his need that much greater, came first! Flooding her womb with cannonades of hot cum. As the first shot exploded against the slick walls of her pussy and his throbbing penis "fired" a second shot, she also climaxed. Muffling her screams of ecstasy into his shoulder, she continued her pelvic thrusts and using her inner muscles...drained him.

Afterwards, turning her back to him, she drew his arms around her shoulders. Cuddling into his warmth, she told him how she had felt, what sensations she had experienced and asked what and how he had felt. After some mutual "love words", they fell asleep, cradled in each other’s loving arms.

The next three weeks went quickly. They made an effort to see each other during the school day, but, in order not to raise suspicions, he "baby-sat" only one time. On that one occasion, after Jean’s sons went to sleep, she and Tim retired to her bedroom where they changed Tim into Tammi. Jean surprised her lover with a complete new outfit in better fitting sizes. She spent the entire night, dressing Tammi, teaching him advanced make-up concepts, practicing his feminine traits and mannerism and making "girl-love".

During this time, Tim called his mother. He found out she was definitely interested in attending the "Tea" and looked forward to meeting his newfound friend, Jean. Over the phone, "mom" sounded different. When he questioned her, she hinted she had a surprise for him, but wouldn’t tell what it was until they got together.

Jean explained to the administration that Tim had told his mother about his "baby-sitting". His mother had called and wanted to meet her. Jean had invited her to spend the weekend at her house and asked if Tim could also stay over. The Commandant thought it was an excellent idea and gave his permission for Tim to "check out" after classes. That Friday, Tim hung around till Jean got off work and the two drove to the train station to pick-up "mom".

The beautiful woman who got off the train looked very little like his mother. Even when she dressed up, she had looked average. That’s not to say she wasn’t basically pretty. Mom had always been slightly overweight, seldom wore make-up, always pulled her hair into a conservative bun, and wore thick glasses and clothes long out of style.

The "new" mom was a major improvement. Immediately Tim noticed the change. Rita had cut and frosted her hair. Her new style was much shorter and swept around over her ears, making her look younger. The glasses had been replaced with contacts. She was wearing make-up! This highlighted her features, thereby helping her appearance. She had lost weight and no longer looked "puffy". Another change was her clothing. Mom had always "dressed down". The "new" mom striding towards them was wearing the height of fashion.

Rita wore a navy, double-breasted coat-dress with six large white buttons across the front. The white lapels crossed just below the upper "swell" of her breasts. The hem was actually above her knees. Her hose were matching navy and very sheer. She wore 3 inch, navy and white spectator heels. The most startling change, however, was her carriage! She had always walked with her shoulders slumped, seldom wore a smile and always looked a little bit lost. Now, her head held high, her shoulders back, her face lit by a flirting smile and with a mischievous twinkle in her eyes, she strode toward them with purpose in her step. The effect was wonderful to watch, she was stunning...and she knew it.

Tim ran to her arms and kissed her, all the while noting the jealous looks he received from the other male onlookers.

"Wow, mom, You look great!"

"Well thank you, dear. I hoped you’d like the new me. Now don’t forget your manners, please introduce me to the lovely young woman standing behind you."

"Mom, this is my friend Mrs. Jean Kinzie. Jean, this is my mother, Mrs. Rita Wayne."

The introductions were made, hugs exchanged, both women agreeing to be called by their first names. Tim retrieved Rita’s baggage and the three headed for the car. When he assisted Jean into the car, she purposely allowed him to see up her skirt. This was not lost on his mother. When Tim came around the car and assisted his mother’s entry, she allowed her skirt to flare open so both Jean and her son caught more than "a glimpse of stocking". As Tim climbed in back, both women turned to the other and smiled knowingly at each other.

On the way, as they waited at a stoplight Jean, turned to Rita. Running her eyes over the woman’s lush body and licking her lips, she informed Rita that her two sons would be staying at her sister’s for the weekend and they would be able to "enjoy" their weekend without any other responsibilities. Upon hearing Jeans statement, Tim’s mother stretched her hand to Jean’s exposed thigh, squeezed the inner flesh and winked her understanding. Both women spent the drive time in disguised female conversation. Using feminine chit-chat to hide their true questions and responses from the unsuspecting youth. Tim sat quietly in back, offering responses only when asked a direct question. Not being as worldly, he nervously wondered what his mother’s reaction would be to Jean and he being lovers. Unbeknownst to him, the women had already communicated and reached an understanding. As the car pulled into the garage, Jean asked.

"Rita, would you like to ‘freshen up’ a bit or would a drink be in order?"

Rita answered, "Why don’t we relax over a drink or two. We have ‘so’ much to talk about, I’m sure."

Entering the house, Jean gave Rita the "two dollar" tour, with the usual pleasantries exchanging between them. As they entered the den, Jean suggested that Tim take his mother’s bag to the master bedroom and hang out Rita’s clothes. As he moved to comply, Jean momentarily guided Tim out of his mother’s hearing and told him to change into Tammi.

"Everything is going as planned. Wait upstairs for my call."

Fixing two drinks, she re-entered the den and sat at the opposite end of the couch from Rita. Before she could say a word, Rita spoke.

"You’re a very attractive young woman, I can certainly see why my son is infatuated with you. I assume, there is no "Mother’s Tea" and you sent the invitation so I would be your houseguest for the weekend. After meeting you, I’m truly glad you did. I’m guessing, but I’d be willing to bet that your aware of Tim’s "special" needs where it concerns clothing. Jean, why don’t we both speak openly and see where it takes us. As you probably know quite a bit about me, why don’t you start, afterall, this was your idea."

Jean held back nothing. She explained how she had foolishly gotten pregnant at sixteen, married, had a second son eighteen months later, her divorce, how she met Tim and the feelings he stirred in her. She detailed the trap she set for Tim and how she caught him dressed in her clothes. She explained how her initial plan had changed and how she then had introduced him to both hetero and lesbian sex. Jean admitted the "tea" was only an excuse to get Rita to visit, just as Rita had surmised.

Rita listened attentively and asked questions when she desired further details. When the story was finished, she slid over to Jean, took her in her arms and kissed Jean...thanking her for helping her son. Then parting Jean’s lips with her tongue, she kissed her again this time with a lover’s passion. Surprised, at the second kiss, Jean returned it with equal fervor. Finally, they broke apart and Rita spoke.

"I think, before you and I go any further, we should bring Tim down, I have some "news" that will be of interest to both of you."

Walking to the stairs, Jean called out.

"Oh, Tammi, would you please come downstairs and join us."

Tim had taken the suitcase upstairs to Jean’s room as he had been directed. Placing it on the bed, he snapped the latches and lifted the lid. His eyes were immediately drawn to the dildo lying atop a beautiful peignoir set.

"What’s happened to mom? If I didn’t know better, I’d say she’s an impostor. She’s never wears clothes like those she wearing today and she’s never had a dildo. I can’t wait to find out what caused the change. I also can’t wait to hear about her surprise."

Taking each succeeding garment from the bag, he hung Rita’s clothes as he had been directed. As he lifted the last dress he discovered his mother’s lingerie. Where he had been surprised before, now he was amazed. The panties, bras, teddies, nylons and garterbelts were of the type he had seen advertised in the girlie magazines she use to give him. The bras and panties all matched, were almost see-through, ranged through the color spectrum and many still had price tags attached. One pair of panties, he noticed, were even "crotchless". What had changed his mother so drastically, he wondered? Realizing he might be called downstairs at any moment, he hurriedly finished emptying the suitcase and began his transformation into Tammi. He had just finished when he heard Jean’s call. Taking a last look in the mirror and pleased with the reflection, he went to join the women. Entering the den, he immediately saw the surprised look of approval in Rita’s eyes.

"Oh Tammi, you look lovely!" She exclaimed.

Turning to Jean, she said. "Jean, you’ve done wonderful things with her make-up and hairstyle. I can’t believe how much more feminine she looks. This is going to make my surprise even more exciting!"

Jean interrupted, "Tammi, come sit between us so your mother may tell you her surprise."

Rita waited till all three adjusted their skirts and then began. "Jean and I have just had a wonderful conversation, explaining all that has occurred between you two. First of all, let me tell you I’m very happy for you both. If I had "picked" a woman to teach him, I couldn’t have made a better choice! Jean, I sense the love between you and I understand your BI-sexuality. I, myself, have always had a yearning to make love to another woman. As you did, I’ve kept it hidden, but after meeting you, I think that’s about to change!"

Jean spoke as she squeezed Rita’s hand in acknowledgment. "That’s one of the desires we can remedy together! The desire I can’t change is I’m sorry I’ve never had a daughter. I love both my sons, but wish I had a young daughter who could share my joy of being female."

"Well, maybe my surprise can help you rectify that situation. Actually, I have a whole bunch of surprises! The first of which is: Tim, I’m in the process of divorcing your father. I know you have questions, but let me explain everything and then I’ll answer any questions either of you have."

Both Jean and Tim nodded their heads in agreement.

"As I said, I’m divorcing my husband. I came home early from work one afternoon and found him in bed with another woman. I was smart enough to take pictures of the two of them. He, nor she, is in a position to contest the divorce proceedings. He’s moved out and I suppose she’ll marry him when the divorce is final."

Tim interrupted. "Mom, he’s no loss!"

Nodding her head in agreement, Rita continued.

"The second surprise is I’ve inherited a large mansion, an equally large sum of money and an import company in the San Francisco area from my uncle, John. Tim, you’ve never met Uncle John, he left Ohio when I was very young. The rumors were he was gay and the family didn’t want anything to do with him. As I understand it, he went to California and made a fortune. The will states that the only member of the family he ever liked was his little niece...me. I barely remember him, but he obviously remembered me. The third surprise is, I’m taking you out of school and we’re moving to California where I’m going to run the company with the help of Uncle John’s lawyer. The surprise is that you’ll be moving out there as Tammi! I’ve discussed your situation with him and he has assured me that you’ll have no problems. The lifestyles of San Francisco are better suited for your needs. Now before you two start crying over losing each other, let me finish."

Again, both Tammi and Jean nodded their acceptance and Rita continued.

"Jean, I’ve done some checking and find that you’re most definitely over-qualified for your current job. I’ll be needing a female secretary/companion who would live and work at the mansion. That person will share my new lifestyle because of my need to work closely with her. I’d like that to be you. I imagine you and I would enjoy working "very" close with each other, both ‘day and night’. I’m sure you understand my meaning. You’d have your own set of rooms, an excellent salary and a nanny to watch over your boys when you were at work or possibly involved in "social interaction" with me. That would obviously leave you the time to further "train" Tammi. Speaking of sons, as yours are so young, I’m sure their memory of Tim will quickly fade and in time, be replaced by their adopted sister, Sarah. Well that’s it, any questions?"

Both Jean and Tammi had questions. Many of them the same. Concerns were voiced, alternatives were discussed and plans made. However, within a relatively short time they where all in agreement and Jean accepted the position as Rita’s live-in secretary/companion, Tammi’s tutor and anything else that might develop between the three women.

Rita and her son’s fantasies had both been fulfilled. She threw her arms around her son, still dressed in his feminine attire and hugged him to her breasts. Kissing and cuddling him in her arms, she told him how much she loved him. All three "women" began to cry, tears of joy. Rita, reaching an arm out, coaxed Jean into joining their hug. There they remained, locked in each other’s arms, the three "women" dreaming of their future lives together.

The End.

 

 

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© 2001 by Kresha Matay. 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.