Matt has always been a bit awkward. His slender physique has not attracted any girls or done him any favors. There have been times where he was caught staring for too long, or listening when he shouldn't be. The girls at his school think he can be a little creepy or just don't even know he exists.
When Matt goes to school he often daydreams of being with a girl. What it would be like to hold her hand, to feel her hair brush against him, or just to have someone beautiful to admire. Lately it has become even more of an obsession, evolving from being with a girl to everything a girl does.
Matt assures himself that it's only curiosity. It is normal for a boy to be interested in how girls work right? His mind wanders to how girls feel, what they must think of, what their clothes feel like...
Matt breaks from his daydream at the last thought. He is a bit perplexed at where he was drifting. It must be because he desperately needs some sexual relief. Why else would he be thinking so drastically? He pulls himself together to trudge through the rest of the day.
When Matt gets home he is excited to be alone so he can relieve himself of all this sexual tension. Although he just can't seem to shake off this notion of what girls' clothes feel like. Feeling adventurous he wanders into mothers room, she will not be home for another 2 hours and his curiosity is steadily growing. He feels a little guilty rummaging through her drawers but is overcome by desire while holding and feeling her delicate panties. For some reason just holding them was not enough, he felt so naughty and turned on that he whisked a pair back to his room.
Suddenly second thoughts filled his mind. Why am I acting so perverted? Shouldn't it be gross to go through my mothers panties? It was too erotic for him to overcome these thoughts. Like a gentle whisper, a dirty thought emerged. He wondered how great it would be to pleasure himself while wearing the cute little panties. It was helpless at this point, he knew that it was what he wanted and he needed that relief so bad. Gently he slipped the panties over his feet. He noticed how the silky material rubbed against his leg hair. It was wrong, but it felt so good. He nestled the panties over his penis and felt himself grow much harder. He had never felt this excited before. With reckless determination, he grabbed onto himself. He pulled back and forth on the panties. The smooth fabric felt devine sliding over his shaft. The build up began quickly and grew. He began to moan softly as he had no willpower to stop himself. Suddenly the pleasure cascaded over and he burst violently into the panties.
Shame. This is what immediately followed. He had just dropped a full load right into his mothers panties. How could he have been so depraved? The panic began to set in about what he should do. His first thought was to pull them off and run into the bathroom as quickly as he could. He rinsed the panties in the sink and tried to wipe himself clean. He threw the panties into the dryer hoping they would be normal before mother was home. Once they were dry he was set to go put them back just where he found them, but he began to wander again. If it felt so good, why am I in a hurry to put everything back? A new plan was formed. He would ruffle the panty drawer to look like before but with one pair removed. Surely she would not notice 1 missing pair. He devised to place them in a hiding place in his room with access. Matt would be able to have time to think about what he wanted, after all he could just slip them in the washer next time mother does laundry and she would never know.
However, as the days went on Matt would never return those panties to his mothers drawer. When he would go to school he would continue to daydream but would always find himself going back home desperate to put on the panties and show himself a good time. At times when he thought about panties he would grow a stiff erection and could hardly contain himself. He knew it was a problem, but he couldn't tear himself away.
As with all secrets, the more he got away with it, the sloppier he was at covering his tracks. Mother was a smart woman who could overlook a detail or 2 but some things were not adding up. Some strange smells were forming that she knew Matt was doing something dirty in his room. There were also some interesting stains forming in the bathroom that Matt didn't think about. She began to wonder what might be happening when she is still working and Matt is home alone.
Then suddenly all of Matt's carelessness his his inability to control himself caught up to him. He rushed home one day after sulking about not having any girls paying him any attention, eager to fulfill his lust with his favorite panties. He didn't even lock his door because his mother was never home at this time and he was so horny. His mother has planned to come home shortly after Matt was home, determined to get more evidence of his doings. When she quietly came inside and heard moaning in his room she knew it was perfect timing.
When she threw his door open to find him laying on the bed wearing HER panties, the ones she had half heartedly been looking for, she became enraged. Furiously she yelled out his name, "Matt, what the fuck do you think you are doing?" Matt was stunned, he had never imagined he would be caught let alone have to explain what he was doing. "Mom, I was..." WHACK. She slapped him across the face. "I can see exactly what you are doing, it is disgusting. You stay right here, you better not move, and you better not finish what you started. I am going to take a breath, and then I am going to tell you what I am going to do."
Mother stepped outside Matt's door and sat down to collect her thoughts. She knew Matt was going nowhere, he has no ambition, and all he seems to care about is getting off. Maybe this is an opportunity, a gross one, but an opportunity nonetheless. She was resolved to turn this embarrassment into something she thought would be productive. Maybe Matt needed mommy to put him on a new path?
When mother returned to Matt's room she sat beside him on the bed. He had not moved and he had not removed the panties. She commanded him to sit up next to her. "Matt, I have decided to take this unfortunate situation in my own hands, things are going to be a little different." As she finished, she took her hand and placed it on his still hard penis. Matts eyes burst wide, he was about to speak when Mother placed her other hand on his mouth. "Matty look at me and listen closely. Mommy knows best. When you are with mommy you feel calm and relaxed."
Matt knew that she was about to do something she promised to never do, use her knowledge of psychology to influence their home life. As she spoke he could not muster a fight, the embarrassment and disgust took hold of him and he drifted into his mothers words.
"Matty you will always be able to tell mommy everything." She began to bring her hand back and forth along his penis. "Listen to my words and know I am doing this because you need me. When you ejaculate into this pair of panties you will suddenly fall asleep. When you wake up you will no longer be able to form an erection unless you are wearing panties. You will be able to focus better at school and you will wait for me to come home. When you have thoughts of self pleasure you will be reminded of how you were caught. I will control when you are allowed to wear panties and when you are able to cum. Our relationship will become stronger because you will need me for what you desire most." she began to increase her hands tempo until Matt had the biggest ejaculation of his life. He fell backwards into the bed fast asleep.
Mother removed the panties, washed them and herself, installed some locks where necessary and went to bed. As she drifted she was surprised about how she felt fully in control over Matt. It was a surprise that controlling him in such a way made her wet. She pleased herself to the feeling of being so dominant and had found a hunger for more.
When Matt woke he remembered all that his mother had said. He concentrated, thinking of breasts, panties, pussy, anything he could to muster an erection. Alas he was as limp as ever. He gulped when he realized that he would have to play by mothers rules.
He was now under her spell...
Matt was horrified as he realized the consequences of last night. Not only did Mother know his embarrassing secret but she had total control over his penis. He didn't even know someone could be hypnotized like that. He knew that Mother was a very skilled therapist, but this was some next level voodoo.
As Matt attempted to collect his thoughts, Mother called for him. It was a school day and they both had to get ready. Matt would have to face a day in which his mind would not be permitted to wander as he was accustomed.
Matt got dressed and sheepishly made his way over to Mother in the kitchen. "So... umm last night..." Matt didn't quite know how to ask her about his obvious questions. Mother looked bright and lovely like she had just slept her best night's rest. She only shushed him gently. "Shhhhh, Not right now. You need to be focused for your day. Remember what I told you? After school you are to come home and wait for mommy. Understood?" Matt could only manage to slightly nod, fearing that and dispute would escalate the situation. Mother gathered her things and left for work, leaving Matt to wonder what was in store for him after school.
As Matt went through his classes he noticed things were different. He paid better attention, he didn't stare at all the girls, and he was more efficient at his schoolwork. Was sex such a distractor that just not being able to form an erection became a game changer? Matt couldn't help but wonder if Mother had done this on purpose to get him to shape up or if he was just being punished. It really felt like more of a punishment since all he wanted to do was run his fingers around his cock, but all he had was a useless baby carrot sized excuse of a penis in his underwear. This didn't stop him from continually trying to get stiff. He thought maybe it'll wear off. She can't possibly keep this going forever! To no avail, every attempt left him in futile disappointment. Even the prettiest girls did nothing.
When Matt got home his curiosity gave him an idea. If I can just find a pair of panties then I should be able to get hard again, thats what mother had said anyway. When he looked around, everything was locked. Mother had anticipated he would go looking of course. Something strange began to set in. All of a sudden Matt felt very fatigued like he had a need to sit down and rest. He found his was to the living room couch and plopped down. Oddly he felt better but no matter what he tried to do he couldn't get back up. Thinking back on last night he remembered that mother had commanded that he wait for her. She couldn't have so much control that she could make me do nothing for 2 hours, could she? As the time slipped by, Matt became more nervous that he was not at all in control of what was happening to him. He was basically neutered and made to wait on his mother. What kind of world is that for a teenage boy? He messed up, sure, but did he really deserve this?
As Matt was lost in his thoughts, he heard the familiar sound of keys unlocking the door. His mother was home and he would learn why all of this is happening and what Mother wanted from him.
When Mother had left for work she had the biggest smile. She knew that Matt would be behaving himself today. She couldn't help but reminisce on last night. She felt so powerful to take control over a man. It excited her just thinking of it. All day long she wondered what it would be like for Matt, to be constantly reminded that his mother controlled his penis. It became so much at one point that she had to release some tension between patients. She knew that when she came home that Matt would be anxiously awaiting her with a helpless look on his face.
As Mother walken inside she had to contain her excitement to see exactly what she was expecting. Matt had a pained expression thay screamed Please! Let me go! She very cooly said "Thank you for waiting Matty, you may be excused." Suddenly the fatigue that Matt felt was lifted allowing him to stand again. He was positively perplexed. He had a million questions but he just went to his room and sat down. There was no good way to ask his mother what he wanted to know so he decided to wait until she started the conversation.
They had a nice dinner. Matt made small talk about school and mother made small talk about work. Neither would budge. They watched TV and awkwardly quiet spells filled the air. Matt was becoming confused and desperate for something. No matter what came up Mother simply did not address any of it. Eventually Matt resigned to his bedroom where he thought he would just give up trying for another day.
Mother came in a few minutes later. "So Matty, I guess you didn't want to ask mommy for some panties today?" Matt was shocked that at the last minute she would bring this up, and in almost a teasing manner. "Mom, why are you doing this to me?" Matt just blurted it out. He didn't want it to happen like that, but he couldn't contain himself. Mother looked upset. "Matty I told you that things would be different, you're just not used to having to ask permission is all. All I have done is give you some proper motivation to behave after you embarrassed yourself in front of me" It was true. She had Matt right where she wanted and all he could muster was a whimpy "sorry".
"Now Matty, if you want any form of release you are going to have to learn to ask for it". Matt knew what she wanted and he fumbled to get the world out. "Can I... Would it be ok to... do you have a pair of panties to umm... be able to cum in?" Mother softened her expression. "Its ok baby, I know you had a hard day. But let's be honest nothing in this world is free. If you want to cum tonight you are going to have to earn it." Mother started to unbutton her pants, take off her shoes, and pulled off her pants. Matts eyes widened when she revealed she was wearing the pair of panties he had just ejaculated into last night.
"Matty I know that you have taken an affinity to womens underwear and I feel that your objectification of women has led you here. You need to understand that a woman's body is unique and special. You are going to be seeing more of mommy as you learn this lesson. You are permitted only to look and not to touch unless you are instructed to do so. Understand?" Matt nodded again and gulped as he was unable to stop staring at mother. "Now what I want you to do is to come over here and very carefully remove my panties. Then take them over to the bed. Ok?"
Matt got up and very slowly and very carefully pulled down his mothers panties. He revealed a path of nearly trimmed hair leading toward her pussy. He began to admire how meticulous she was at keeping it neat. He fully removed her panties and sat down only to stare at her exposed pubic region. "Matty can you please look mommy in the eyes? This is how a woman looks and you need to get more comfortable being around it. Now take those panties and put them over your head." Matt does so transfixed on what is happening. "Take a big breath. This is what a woman smells like. I want you to savor the smell. It may be a long time before another woman besides your mommy lets you inhale their scent. Not take them off and notice the change of texture in the center. This is where the panties cradle my pussy. I want you to lick it."
Matt hesitates. Mother claps her hands. "I SAID LICK IT" He sticks his tongue out and just barely touches it. "No, I want you to get it soaking wet. Lick it like its the best ice cream you ever had '' Matt repeatedly runs his tongue over the fabric. "This is what a woman tastes like. You may not ever get to taste a real one unless you learn to respect them. Are you ready to put them on?" Matt is immediately ready, he responds "yes" without even thinking about it. "You may put them on but you may not touch yourself".
As Matt slides the soaking wet panties over his legs he is reminded once again about the intoxicating feeling. As they cup over his testacles and penis he begins to become hard before he can even get them on fully. It becomes an intense erection as if all the tension he would have had throughout the day has suddenly come on all at once. An involuntary moan escapes his mouth as he finally has them in place.
Mother comes forward and places her hand over his penis and grips firmly. "Matty, look at me and listen closely. Mommy knows best. When you are with mommy you feel calm and relaxed." Matt becomes anxious at first. She said this last time and some things happened that he couldn't explain. As she completes this phrase, Matt's mind gives way to the sound of her voice and he is involuntary relaxed.
"Matty you will always be able to tell mommy everything." She began to bring her hand back and forth along his penis. "Listen to my words and know I am doing this because you need me. When you look at women you will no longer be able to see them as sex objects. Unlike your deadbeat father you will see women as unique and wonderful. When you think of women you will be curious about how they chose their clothes. You will notice how they all do their makeup. You will admire all the effort they do to make themselves look good. In fact you will be envious that they are prettier than you. It is time for you to be immersed in a world you are unfamiliar with. When you think of women you will not be trapped in the desperate desires of your penis but you will truly ponder what it means to be a woman and what it takes to be one." As she finished Matt blew a violent load into the panties and fell back fast asleep.
Mother couldn't wait any longer. Dominating her son had made her fully aroused. She quickly removed the panties from Matt and went back to her room. She rubbed her breasts with one hand and fingered herself with the other as she replayed her message to Matt. He would learn what it's like to be a woman. She was in complete control and herself had a violent orgasm. She was too deep to stop now, while she didn't know where this was going it was too good to stop anytime soon.
Matty!" Matt awoke to his mother calling him from her room. The door was open and she was standing in only a towel after having just taken a shower. When he managed to get himself over to her she dropped the towel on the floor. Instead of ogling his mother like he normally would have, Matt could only admire her. He thought she was so fit for a woman of her age. She must take pride in taking care of herself. Matt felt a bit of shame, realizing he didn't take care of himself in the same way. Suddenly he noticed all the times he ate junk while his mother settled for a salad. She was so strong willed and determined.
It was strange, Matt finally had a beautiful naked woman in front of him but because of his mothers "lessons" he couldn't enjoy it at all. His penis was completely flaccid and all he could think about was how he had such an empowered mother to be thankful for. In fact he envied that she was so pretty.
"Matty I called you in here because as part of our new relationship I want you to help me get ready for work in the mornings. This will better help you understand all that a woman has to do to be presentable in our society. The first thing I want to go is to put on a pair of panties. I have unlocked the drawer for you, you should be familiar with the offerings in there. Try to think of what you should pick based on my needs. Ok?" Matt moved over to the dresser and began to search for the pair he thought she would like. Normally he would be overcome by wanting to put them on himself and jerk off but things were different. He thought about what they would feel like to be on all day long, if they were practical for a work environment, and lastly about how cute his mother would look wearing them.
After all a strong woman like her deserved to look her best. He chose a light pink pair of cotton bikini style panties since they would both feel good and look on him mothers physique. "Umm... I think these would be a... umm good choice." Matt was kind of embarrassed to be picking out his Mothers panties but he also really liked it. He would have to be careful to not be too obvious of his enjoyment. "Thats a good choice Matty. These will feel good against my body accentuating my body and will not be evident underneath my clothes. Since you did good, why don,t you help mommy put them on. Come kneel in front of me and lets get started."
Mother was very turned on at this point. She took her son from a little panty thief, to learning about womens clothes and being a little helper. At this rate Matty will soon do whatever she tells him too. It felt so good to be exerting her power over him by putting him in such a weak state. She would never have to worry about him talking back, sexualizing her, or making himself into a degenerate. It felt good to usurp all of the power.
Matt knelt down and held out the panties. Mother stepped into them and signaled for him to pull them up. He lifted them until he came face to face with her pussy again. He was mere inches from something he only dreamed about. He couldn't think of anything sexual though, only how well trimmed her pubes were and how some man would be very lucky if she ever game one a chance. Matt became worried, was he just thinking of his mother presenting her pussy to some guy? This was definitely a weird way to think of mother. He finished pulling the panties up, making sure to smooth out the front and back. He took care to make sure there were no wrinkles or creases. He wanted his mother to look just perfect.
"Did you like that Matty?" Mother knew he would, and she knew he would confess if asked. "Yes." Matt just blurted out. He knew he would not be able to be dishonest but was taken back from how involuntary his response was. He didn't even have a chance to consider his answer. "Well I am not surprised Matty. Since you already had experience in panties I figured that actually having to do it proper would be a thrill as well. Do you still want to wear mommy's panties?" She was actually curious how it would affect Matt. "Yes. Actually more than ever. I want to learn how to do it proper so one day I can do it for myself." Matt cusped his hands over his mouth. That was a thought he had never admitted to anyone. Now she would know that we wanted to wear more than just panties. He was sure that now his path would lead to even more of these "lessons".
"That's good to know Matty. Now let's get going, I don't want to be late for work. Next go fish out a good bra for me out of the drawer above the panties. Ok?" Matt rushed over to the dresser anxious to put some distance between him and his last embarassing comment. He was still red faced from spilling his secret. Focused, he picked a bra that he thought would deliver support, one he checked would not poke or have scratchy fabric, and that would easily be covered by work appropriate attire. Mother had Matt place the bra over her breasts, slip the straps over her shoulders, and choose the clasp that would be firm but not too tight.
"That was good work today Matty. I know you do not yet have a sense for clothes and make-up, so I am going to choose some. Make sure to pay attention and think about why I want to do things." Matt's mind was flooded with various new thoughts: How something would look on her body, how the colors contrasted her complexion, how her features were highlighted or dulled. There were so many complexities that he had never cared to notice before. It felt as if a new world was suddenly opened before his eyes, a new girlier world. He thought he would be repulsed by all of these feminine practices, but he found himself continually more intrigued. He wished his morning routine was more like his mothers. He felt plain when he saw how much prettier she was. As she applied her make-up, he noticed how all the layers elevated each other. She was transforming into a beautiful butterfly ready for whatever challenges awaited. He had never realized before how much a woman went through just to be able to go outside. Matt was sad that he had tried to rush her before and commented how she had made them late. Mother's instruction was playing out perfect as Matt was beginning to understand what he had chosen to not care about.
Mother dismissed Matt to go about getting ready afterward. He lazily got ready as he was disheartened that it was so much duller than his Mothers routine. He couldn't believe that he was actually looking forward to helping her tomorrow morning. At breakfast Mother prodded Matt to confess all that he had observed and learned. It was refreshing to hear him seeing things from her perspective. He was beginning to talk to her like one of the girls. It wouldn't be long before he would be begging to look like one of the girls too. After all he had confessed that to be his desire earlier. She had a devious smile as she sat and listened. Mother would find a way to make Matt into his best self. even if that meant making him into a her.
Mother went to work, when she got there she pleasured herself to all the pent up energy from the morning. At this rate she would need to find a man to help her take care of these emerging needs. She wondered how Matt might react to having a man around the house more often.
Matt went to school and it was quite an overwhelming day. Instead of daydreaming about girls in a sexual way, he constantly thought of all of their morning routines. How every girl there had to choose their clothes, do their make-up, and consider how their choices would make themselves appear. All day he felt like an ugly duckling. Forced to appreciate all of the beauty around him but be stuck as an impotent boring excuse of a boy.
Interestingly a girl sat with Matt at lunch. He normally sat alone ostracized by both the boys and the girls. This girl was Sarah, she wasn't the most attractive and didn't have too many friends but she had noticed Matt acting differently and was curious to talk to him. Matt actually found himself complimenting Sarah instead of fantasizing. She was a bit timid like him but they found each other friendly enough. Matt worried that she would discover things about him so he tried to keep the conversation school focused. As much as he tried he couldn't stop himself from talking about her clothes, or her look, or her hair typically in a compliment form. Sarah figured this must mean that Matt is gay. A normal guy wouldn't think twice about any of this. Maybe if they got to know each other he would reveal this to her. As lunch passed Sarah let Matt know she would sit with him again. This made him very nervous as he couldn't contain his "lessons" as it is. What if mother kicks it up a notch? It wouldn't be long before he loses all control.
The rest of the day seemed to fly past him. Just like the day before Matt came home and felt compelled to wait for mother. It was stronger than yesterday. He was being conditioned to wait for her and there was nothing he could do other than wait.
Mother got home and told Matt she would be going on a date. There was a man in the office across the building that she had her eye on but never had enough confidence to talk to. Feeling empowered by domination of Matt, she struck up a conversation which led to him asking her out.
"Matty, let's see what you learned today. I want you to help mommy look sexy for her date. Mommy is not a slut so this is a balance in choosing clothes that will make him want to see more without revealing too much" Matt asked her "Isn't it weird for me to help you get ready for a date?" He knew it was a mistake when it came out. Mother calmly replied "Not as weird as my son wearing my panties, now let's go". His face turned red again. He knew better than to question her at this point. He quietly marched to her bedroom. "Alright matty. Help me get undressed and I want you to pick a panty set on the bottom drawer. I unlocked it for you, those are my sets for when I have a date." He helped mother slip out of her blouse and skirt. He unclasped her bra and slid her panties off. Carefully he placed the clothes in the hamper and went to her designated drawer. He picked out a red thong and bra set. They were sexy should she decide to reveal herself tonight. Together she was dressed and put on a high slit red dress to compliment her figure. She helped Matt to pick out some jewelry and shoes to match.
"Matty, I have some instructions for you while I am on my date. I want you to take the clothes I wore today from my hamper and put them on. Get yourself dolled up the exact way we did it this morning. Make-up, shoes, and clothes all neat and pristine. You are not allowed to cum. If I come home and find cum stains or cum in my clothes, I will make it so you never cum again. You are to make yourself dinner and watch romance movies on TV until I come home. If you are dressed like a woman you should behave like one. I want you to write descriptions of what all the women are wearing in the movies and how they compliment their features. Lastly, I want you to tell me who the cutest boy in the movies is. No arguments, if you behave I will have a reward for you when I come home."
Mother headed out the door. Would Matt be able to behave tonight or would he be doomed to be erectionless forever?
Matt watched his mother walk out the door to go on her date. The last couple days swirled around in his mind. While he knew that things were escalating quickly, he was actually enjoying all of the "perks'' mother had given him. Before all this he was a sexless loser who had a weird panty fetish that no self respecting woman would ever give a second glance. However in the last few days he had received some weird but very enjoyable handjobs, seen a woman naked (his mother but a woman nonetheless), and has been able to exercise his fetish of wearing panties. Things were not going the way he intended but the temptation of another reward was tantalizing.
Matt was giddy about getting to wear his mothers panties around the house tonight. While unsure about fully dressing as a woman, the panties were enough to excite him. He found the light pink pair of panties in his mothers hamper and without hesitating he brought them up and buried his face in them. He took long breaths relishing her scent and feeling her smooth delicatates on his skin. After a few moments he pulled himself away eager to put them on. He pulled the panties on and gently nestled his penis and balls so they were confined. He fished out the bra she had worn to work along with the blouse, skirt, and heels. It was so much more difficult to put the bra on himself than it was on his mother. He yanked on the straps and nearly threw himself down trying to get it clasped. He felt sympathetic on how mothers and girls everywhere had to do this everyday. The blouse didn't feel much different than some button down shirts he had but it was tighter on the sleeves and at the waist. This and the bra felt incomplete without breasts so on a whim without prompt he decided to stuff the bra with toilet paper as to have a complete look. Afterward he slid the skirt up his legs and over his panties, he sat down to put on the heels as well.
Walking around was a brand new feeling for Matt. The skirt rubbed against his thighs and he could feel the panties also rubbing his penis underneath. He wobbled in the heels as they made him stick out his butt and lean forward when he walked. It felt almost impossible to keep his balance and he wondered how mother did that all the time. After strutting around the house dressed like his mother, Matt went to the bathroom to see if he could try and replicate his mothers makeup routine. Some things felt simple like putting on blush and lipstick, while the eyeliner and blending the tones was difficult. He looked like a man had tried to do his makeup. Mother would surely scold him for not remembering as much as he could have but he figured the attempt was what mattered.
Matt waltzed down to the kitchen. He was going to make himself some ramen for dinner. While he was bending over and grabbing things he felt just like he imagined his mother did while she was cooking. It was a weird feeling to be imitating his mother but he was intoxicated with the pretty clothes and of course the happy endings in mother's panties. All the moving around was causing Matt's penis to keep rubbing the panties. He had been stiff ever since he had put them on. All he wanted to do was stop making the ramen and rub himself the way mother does. If he did that she would probably make it so he could never cum again. He softly moaned in frustration at the thought of not being able to get off until Mother says so. It was different when it was not possible, now it was cruel to give him the panties but no relief.
When the ramen was done, he went to the couch to watch TV. When he sat down if felt weird having his legs open, he could feel air coming up the skirt and brushing against the panties. Girls usually sit with their legs crossed when they wear a skirt, he thought. It was a bit surprising to him how that information came up so quickly. Mothers command to notice how women behave was working overtime. He crossed his legs which felt more feminine but also pressed his penis against himself to help him deal with the constant erection. Matt grabbed the nearby notebook, pen, and remote to turn something on. Matt thought he was going to watch the notebook since it was the only one he knew but he couldn't find it. He did find dirty dancing which was just starting and he had never seen it. He started writing down the outfits for baby, penny, lisa, and the rest of the girls while eating ramen between notes. He tried to find someone other than Johnny to put down as the cutest. Patrick Swayze is just too good to not pick. His shirtless scenes and muscles looked great and he had a kissable face. It was concerning that he was thinking about a kissable face while being a man wearing mothers panties but this was his life now. He kept squirming in his panties while thinking about Patrick hoping mother would be home soon.
Mother drove herself to the restaurant. She met Bill at a table as he was waiting for her. He commented how she looked sexy and was happy that she agreed to go out with him. It was apparent Bill was drooling over how the dress complimented her figure. Mother sat down and the two made small talk while they ordered. Bill worked as a clerk in the local records department. He chatted a bit about it but it was a bit boring for mother. She talked to him about the craziness of being in psychology. Bill hung on her every word fully captivated by both her beauty and her stories. The two ate dinner and drank wine. While Bill was very much falling smitten, Mother had other things on her mind. She thought the date would help her with all this lust that she had been feeling throughout Matty's 'treatment'. All of this normal date stuff felt so trivial and boring when she knew that at home there would be feelings of dominance and power that had felt so very good. It was a mix of guilt and taboo that drove her wild when she squeezed Matty under her thumb or when she instituted his 'corrections'. She was getting hot just thinking about it.
As dinner wrapped up Bill tried to make his move but Mother smoothly let him down. She asked him to allow them to take it slow and since they work near each other that they could chat soon. She considered that she may want a second date but Bill was just kind of plain and the sex would probably be vanilla. As mother drove home she wondered if Matty would be obedient. If he reverted back to his old self, all of this work would be for nothing and she didn't know if she could bring herself to start over. The thought of Matty all dressed up in her clothes and thinking about boys was just such a treat. There would be no way for him to be able to resist further changes. She was wet at the thought. While driving she rubbed her clit and planned for what else the evening would entail. Since her date fizzled she was coming home horny and frustrated.
When she opened the door, all of her fantasies were realized. She laid eyes on a feminized Matty wearing her clothes and scribbling in a notebook about all the girly clothes and cute boys. "Hi Matty! I'm home. Come over and let me get a look at my little angel." She squealed in delight as she realized he had followed all of her instructions. He had assembled the outfit. It appeared dry, and he was sporting an erection held up by the panties indicating he had not had an orgasam. His makeup was about what she expected, he was not a very quick learner and she anticipated it would take some practice. "Very good Matty. Go grab your book and let's talk about what you watched tonight." Matt talked to mother about how he watched dirty dancing and all the outfits all the girls wore. He blushed when he talked about Patrick and his shirtlessness and kissable face. Mother smiled, "You know, I used to have a big crush on him when I was younger too. Like mother like daughter I guess." She referred to him with a female title for the first time and wondered if he would react. Matt just turned red and nodded. He felt alarmed to be referred to as her daughter but he did look the part. He was going to get a reward and that was really all that was on his mind anyway.
"Matty since you were good tonight I have a big reward for you. I want you to go to my room tonight. When you get there I want you to take off your heels, your blouse, and your skirt. Neatly place them in the hamper and look in the little box on top of the dressor. These is a blindfold in there, put in on and wait for me on my bed." This was new. Mother had always done her handjobs for Matt in his bedroom and the blindfold was absolutely kinky. Matt wasted no time rushing into her bedroom and following instructions. Mother went to the closet to grab a few items for tonight. She had planned out this "special reward" for some time now. This would take her over the edge with Matty. She knew after tonight things were going to be weird, they were going to be awkward, but she had never felt so alive and so horny.
When mother got to the bedroom she found Matty patiently waiting as instructed. She told him to lay down while she pulled the items from her bag. The first items were a pair of handcuffs. She took Mattys arms and handcuffed them to the front bed posts. When he tried to protest she took her finger and placed it on his lips to shush him. "It's ok Matty you are going to have some fun tonight." Then Mother undressed herself to be completely naked. Matt was still blindfolded and couldn't tell what she was doing. The next two items in the bag were a double sided strapon and lubricant. Mother was planning to pop Mattys cherry tonight. She lubed up both ends and worked the harness up to her body. Carefully she inserted the interior dildo into her still wet pussy. It had been too long since she had something or someone inside her. She lightly moaned in anticipation for what was to come.
"Matty. You were such a good girl tonight. Mommy was worried that you would not be able to follow instructions. Since you have shown such great improvement it is time for your reward. Tonight I am going to teach you one of the great joys of womanhood and that is being fucked. Congratulations Matty you are going to lose your virginity" Mother was sensual and direct. Matt squirmed. He was not sure that meant he was going to have sex with his own mother or if something else was going to happen. "Mother I don't understand?" Matt questioned. She shushed him again. "Matty you should relax and just try to enjoy it ok?" She responded right away. Now on the bed she grabbed both of Mattys ankles and lifted his feet into the air. As she did she pulled him towards her, lining him up. "No wait. Mom, I don't want to do this. This is wrong" He squeaked and squirmed trying to resist what he now knew was going to happen.
Mother slid the panties to the side exposing Mattys butt and his little hole. She pressed the head of the dildo against the opening until Matt whimpered while still protesting. "I will be gentle Matty but this is a very special feeling and intimate act so I need you to be quiet now" Since he had no way to resist her, Matt just waited for the inevitable. He always dreamed of losing his virginity but he never dreamed it would be to his mother or that she would be the one doing the fucking. Mother pressed forward slowly inserting the lubed dildo into Matt's asshole. He yelped with the burning and pain of being stretched. Little by little the dildo creeped forward until it was completely inserted.
"Matty, feel how full your new pussy is and listen closely. Mommy knows best. When you are with mommy you feel calm and relaxed." He wanted to scream but suddenly he started to relax as her words seeped into his mind. "Matty you will always be able to tell mommy everything." She began to bring her dildo out slowly and then push it back in. Matty softly moans. "Listen to my words and know I am doing this because you need me. Right now you are being fucked like a girl. You have spent the evening dressing like a girl and trying to think like a girl. You did not resist me when I called you my daughter. From now on you will only refer to yourself and be referred to as a girl. Your new name is Madeline. Your pronouns are she and her. You will no longer be able to use the words Matt, boy, man, or associated words when referring to yourself. Girls like yourself have orgasms when they are fucked in their pussy like we are going right now. You will always refer to this as your pussy from now on. In addition to you not being able to be erect without panties, you will also not be able to cum unless you are being fucked in your pussy."
Mother picked up the pace. Both ends of the strapon were gliding back and forth. Maddy began to moan loudly and her penis looked like it was about to explode. Mother twisted her own nipples as she focused on giving the both of them the pleasure they needed. She was so turned on by being the one in charge. She started moaning in unison with Maddy. "Oh Maddy. Mommy is going to cum. Mommy feels so good right now. Maddy lets cum together. 3... 2... 1... cum!" As she shouted Mother convulsed in the biggest orgasm she ever had. The combination of the dildo and the wild thoughts had driven her crazy with lust. Simultaneously Maddy's penis bursted a load of cum into her panties. Maddy lay breathless on the bed from the moaning and the powerful orgasm.
Mother slipped out the dildo from Maddy's pussy. "Good girl" she cooed. She removed and cleaned up the harness before putting it away. When she came back, Maddy was fast asleep on the bed. Mother changed into a nightgown and adjusted Maddy's panties back to normal. She cuddled up to her daughter on the bed and whispered "We will have to do that again" as she drifted unconscious, content with how well the night had gone.
Mother spooned Maddy all night long. She had missed the intimacy of sharing her bed with someone. She must have smiled for hours after her orgasm. She never had imagined she could do this to her son and she never thought she could fuck someone like that. Mother was intoxicated by all the power and she felt so alive for the first time in a long time.
Maddy woke to find her mother was spooning her. Her mind raced as she remembered all of the details from the night before. Mother had taken it too far. It was just a silly little panty fetish, she never thought that it could lead to this. Maddy turned over to see her mother waking up.
Mother patted Maddy's head. "Good morning daughter. How's my little girl?"
Maddy struggled to find her words. "Mom... I think this has gone too far. I'm a... I'm a... I don't want to be your..." As much as she tried she was not able to complete her thoughts.
Mother smiled and reassured her new daughter. "That's OK Maddy. You take your time. What are you?"
Maddy kept struggling but she just couldn't break free. "I'm a... I'm a... girl." She was frustrated and hung her head in defeat.
"That's a good girl. You must have a pretty name too. Do you remember your name baby?" Mother teased her knowing the answer.
"My name is Ma... Ma... Mad..." Maddy cleared her throat and tried again. My name is Ma... Madeline.
"That's right Maddy!" Mother praised her. Now she would put her spell to the test. "Did you enjoy your surprise last night?"
Maddy squirmed on the bed as she attempted to resist blurting out her true feelings but she failed just as before. "I didn't want you to do that... at first." She gasped and tried to stop but kept talking anyway. "After a while, it felt really good and it was the best orgasm I have ever had".
Mother was thrilled at how this was all coming together. "That's wonderful dear. I just don't think you are being clear enough. What was it that was so good?"
Maddy couldn't even think before she automatically responded. "I liked it when you fucked my pussy". Her eyes went wide. She had not meant to say any of that but it just burst out of her uncontrollably.
Mother snuggled close to Maddy and whispered into her ear. "I liked fucking your pussy too".
The two girls lay on the bed in an awkward silence. Maddy was digesting what her mother had just told her and her mother had that look in her eye. While they were deep in thought, Mother reached down and started to touch Maddy's penis over her panties. Maddy was getting hard and Mother seemed to be enjoying it.
Mother looked at Maddy in the eyes and saw how badly she wanted to cum. She knew that Maddy would do anything she asked now, she was putty in her hands.
"Kiss me Maddy" Mother purred.
Maddy got close and gave her mother a quick peck of a kiss on the lips.
"Not like that baby. Like you mean it. I want you to kiss me the way you would want to. You need to convince me to fuck you."
Maddy hesitated but she was so horny now with her mother constantly rubbing her little penis. She lunged forward and passionately kissed her mother. She worried it was wrong but her body was in total control.
Mother pulled Maddy in close and wrapped her legs around her. She put one hand on the back of her head and one hand on her ass. They made out for several minutes both allowing their tongues to explore the other's mouth. Mother moaned in delight as her new daughter-turned-lover made her wet with excitement.
Mother finally broke off and ripped the covers off. She started kissing Maddy all over her body but focused on kissing her all over her panties and her penis.
Maddy moaned and panted and squirmed all over the bed. No matter how much Mother teased her penis she would not be able to come. Thanks to last night there would be only one way. "Mother. That feels so good. Please. I need to cum. I'm so hard but I can't. Help me."
Mother started to gently kiss Maddy's neck. She whispered in her ear "How do you want me to help you, baby?"
Maddy blushed as she thought the words in her mind. "Can you please fuck my uh... my um... pussy?"
"Oh, you naughty girl. You naughty girl. Are mommy's little slut now?"
"YES. I'll be whatever you want. Just please fuck me!"
"Oh, Maddy. You have lots to learn about being a girl. You see girls like to be intimate and when their bodies are ready it becomes electric. Plus it's not just you in this bed dear. Why don't you let me help you with your mental block? I want you to consent for me to make you a better lover. I will help you to be able to eat pussy and make me orgasm. Do you want to be mommy's little pussy licker?"
Maddy thought about it. Her penis was throbbing under her panties and she was becoming desperate for release. Thanks to Mother the only way she could release was if Mother or *gulp* someone else fucked her pussy. Truth be told she kinda wanted to eat Mother's pussy anyway.
Maddy was face to face with Mother's most bold desires. If she consented, Mother would take her even further into this wild nightmare. "Ok, Mother. I want to be your pussy licker."
"Maddy you will always be able to tell mommy everything." She began to bring her hand back and forth along Maddy's penis. "Listen to my words and know I am doing this because you need me."
Mother grinned as she carefully planned out her instructions. "When I stop rubbing you will be a passionate lover. When you make love to me you will worship my body. You will explore every inch with your hands and your mouth. You will be driven to please me and bring me to orgasm as many times as I want. When you eat my pussy you will taste the most delicious things you can imagine, it will be greater than anything you have ever had. You will be obsessed for more. No other woman can give you these feelings. Only a man can make you feel the way you do when you are with me."
Mother stopped rubbing Maddy's penis and she looked lost far away. Suddenly she snapped back to reality and embraced Mother, kissing her tenderly. Maddy spent what felt like hours exploring and teasing every part of Mother's body.
Mother screamed in delight as Maddy brought her to countless orgasms each more powerful than the last. Maddy's tongue had a mind of its own. It flicked and flailed as Mother arched her back and panted loudly.
When fully satisfied Mother told Maddy that she had fulfilled her duty as a lover. Maddy was still needing release and pleaded for their mother to finally grant her request. Mother obliged. This time she took a standard dildo out of the drawer and helped Maddy to position her ass to be fucked.
Gently Mother pressed the dildo into Maddy's pussy. Maddy moaned in pleasure sensing that release would be near. The dildo kept pushing deeper and deeper intensifying the pleasure with every inch. Maddy screamed out in bliss with every thrust. Finally, a humungous burst of cum shot into her panties and both women lay on the bed marinating in the pleasures of the morning.
Mother confessed "Maddy, when all of this started I was just hoping that I could help you avoid becoming a degenerate. I hope you are happier as a woman. I had given up on finding a lover after your father. I never imagined a sissy could make me feel this way. I love you, Maddy. You're not just my daughter anymore. I think you should be my girlfriend too."
Maddy and Mother kissed passionately after her confession. Maddy was going along with the show like she had any choice otherwise. Mother explained she still thought they should seek out boys for love but would always have each other no matter what.
Mother encouraged Maddy to take a shower and get ready for school. The mother also supervised her while she got ready for school. Mother insisted that Maddy wear full makeup, a dress, and some low heels for her first day as a woman.
Maddy expressed how she was afraid to face school again this way. She held back tears as she imagined how cruel some kids can be. Mother held her and comforted her and promised she would be there for her. Mother even joked that perhaps some guy would stand up for her, a big strong man who needs a girlfriend. Mother winked.