Falling Under Mommy's Spell Pt. 04

Disclaimer: The characters appearing in this story are 18+ and fictional.

Thank you all for reading my story. This is a continuation, if you would like the complete tale you can find the previous chapters on my profile. Much love!

Part 4: Matty's Reward

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.