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  Putting Him in Panties

  By Allison Heart

  Published by Allison Heart at Smashwords

  Copyright 2015 Amor Publications

  Putting him in Panties

  Copyright © April 2015 by Amor Publications

  Chapter 1

  Milo was younger than her, which is why he was so prone to suggestion. Sabrina realized that the first night they were together. He was eager to please and gladly took orders if it meant that she was happy, which is why she found it weird when he took off his pants to reveal the skin tight boxer briefs he wore.

  They looked incongruous on his trim, lithe frame. Save for the plump roundness of his ass, she couldn’t imagine what his underwear choice was supposed to show off. After all, he wasn’t that well hung to begin with.

  “I think you should take those off. Give them to me so I can throw them away.”

  “But what will I wear home?” Another trait that comes with being young; he had a tendency to whine. She already had them in her hand and held them with thumb and forefinger distastefully, like something she picked off the bottom of her shoe.

  “Go commando. I’ll find some new undies for you tomorrow.” She already had them in mind; all she had to do was run to the store and find the right pair to fit him. After that, she knew there would be no turning back.

  When he returned the next day she had a nice, fresh pair of pink hiphugger panties that were guaranteed to give a snug fit. Kneeling in front of him with his pants at his knees, she was disappointed to see another pair of boxer briefs, worse than the last. She yanked them down with a fury.

  As expected, he was erect and with a dumbly happy look on his face. She had taken him in her mouth often and most likely he expected the same treatment. From her position she was certainly in the right position for it.

  Which is why his face crumbled when she held the panties up in front of him. “Step out of your pants and step into these.”

  Putting a man in women’s underwear has a significant effect on him. Sabrina wanted to test the theory and no one was better suited to the task than he.

  “What?” Again, more resistance. It irritated her, even if the sight of his penis slowly shrinking brought a slight jolt of confidence.

  “I said step into these. You’re going to be wearing panties from now on.”

  “But…but I’m a boy.”

  Interesting that he didn’t call himself a man, she thought. “Just do as I tell you. Remember, I know best.” Long ago he had agreed with this and it became an inside joke with them. Whenever they disagreed, repeating the phrase would put an end to any disagreements.

  Unable to look at her, he took the panties and stepped into them. Watching him carefully maneuver the thin, pink material up his long, smooth legs sent a surge through Sabrina’s body. They looked so much better on him. Boxer briefs looked too frumpy and out of place. He needed something softer and more delicate.

  When they went out together she took pride in the secret he wore under his pants. She was much more affectionate, something that surprised him. An encouraging hand on his ass got him moving quicker than usual.

  Something else she noticed; he was quieter with panties on. Before he was just like every other boy- loud and overbearing without realizing it. Now, with a thin layer of panties against his skin, he became docile. She liked the change and rewarded him with surprise kisses whenever she could.

  Milo was also nervous, often getting tongue tied when he tried to speak. When the server came to take his order she thought he would overheat from nervousness. All the while she beamed at him happily. Yes, panties suited him well.

  Unable to order, she chose what he would eat and had the waitress bring him a salad and a glass of water, winking at the woman with a shared knowledge of what was best for him.

  “Just a salad? But I’m hungry!”

  She shushed him. “You don’t need anything more than that. I want you to keep your figure sweet and pretty.”

  The compliment was so flattering and so genuine that he didn’t argue. Suddenly randy, Sabrina found herself taking off her shoes to run a stocking clad foot up the inside of his legs. When she reached his crotch she found him hard just as she suspected.

  Across the table from him, chin resting on her fingers, she watched him grow more and more uncomfortable. “Too tight?”

  He almost choked on the water he was sipping. “Excuse me?”

  “Are your panties too tight?”

  Frantically he looked around the room. “Sab, don’t. Please.”

  She liked the tone in his voice. “Why? You don’t think people actually think you’re wearing panties, do you? Not a grown boy like you.” God, how wet this was making her.

  He flushed scarlet and tried to manage a weak smile. “Ok ok, just please keep it down, would you?”

  She returned with a slight smile as the waitress brought their food. “Hamburger well done with sweet potato fries.” She said, placing it in front of Sabrina. “And a light salad.” She patted him on the head, winking at his girlfriend. “Is there anything else I can get you?”

  “I’m fine. Do you need anything, dear?”

  Milo seemed to be frozen in place, eyes wide and pleading at her from across the table.

  “Would you like a Shirley Temple?”

  He shook his head then remembered. “Could I maybe have some lemon for my water?”

  The waitress promised to get him the best lemon she could find then turned and skipped away. Milo found the strength to raise his head and give his girlfriend an accusing look.

  As they drove back she stroked the juncture of his thigh, tracing the hidden ridge of panty beneath his pants. “You really took to them.”

  He was looking out the window absently, probably hoping the night would pass as quickly as possible. “What?”

  “Your panties. They fit you well.” She noticed him twitch as she said it. Your panties. That’s what they were. She got them for him to wear and they fit him perfectly. “Come on, admit it. You like them.”

  He couldn’t resist a shy grin. “Ok, they do feel pretty good.”

  That caused her to swell with excitement, almost running them off the road. She jumped and gave him a quick kiss. “Good, sweetie!”

  When they arrived home, she held the door for him and ushered him inside with a playful pat on the butt. “It’s late. Get upstairs to the bedroom and wait for me. Don’t dawdle.”

  Eagerly he ran upstairs, looking forward to any sexual attention she would offer. Their sex life had always been rampant. Unpredictable when it came to love, she often left him guessing then exhausted and sapped of energy by the time she was finished.

  When she arrived he was naked, reclining on the pillows like the cat that ate the cream. His cock was firm and angling toward her.

  “You look like you’re ready, don’t you?” She asked and he nodded, his eyes wild with desire. Rather than strip for his pleasure, she made her way to the bedroom where she undressed nonchalantly. From his position he could only see her reflected in the mirror.

  Her body wasn’t as pretty as his. Rounder in the hips than she’d like, she had a wide butt. Her breasts hung farther than she’d like, her areolas dark and wide as coasters. One thing she was always proud of were her nipples. Perfectly formed, they jutted from her chest in thick nubs that none of her lovers could resist.

  “Honey?” he called from the bedroom.

  “Just stay there, girl. I’ll be there in a second.” Brushing her teeth, she let her hair down before walking to her dresser. He watched each step she took, marveling in the naked body of his girlfriend. She always seemed so in control, so sure of himself, especially when naked. It made his own self doubt that much more obvio
us.

  She pulled out a pair of flannel pajama pants with an elastic waist. “Put these on.”

  He balked. Anything but his underwear was too much to wear to bed and some nights, especially after sex, anything was too much. “Why?” He felt the fabric between his thumb and forefinger. It was soft and gentle; against his body it would feel lovely.

  “Because I want you to.” Staring him down, she added “And I think you’d look cute in it. Isn’t that enough?”

  His cock hung in midair, oblivious to the power struggle going on between them. Squatting down once more, she held them open for him as he stepped into them carefully. Rising, she pulled them over his legs before tucking his slender cock beneath. With his erection secure, the bottoms tented around him and she felt a wave of heat from his compliance.

  “Come on boy,” she urged. “Get on your knees.”

  He went willingly, still afraid to look her in the eyes. He took to his knees like a knight about to be honored as she spread her legs. A hand on the back of his head slowly pulled him against her.

  Weeks ago she had shaved her pubic bush to surprise him during their sex play. Though she had kept it trimmed since, much of it had grown back. Soft hairs tickled his nostrils and made him wrinkle his nose as she pulled him forward. When the flat of his tongue licked against her slit, however, she groaned with pleasure. All that evening she had steadily begun to moisten and now, seeing her cute, young boyfriend wearing a girl’s pj bottoms, she couldn’t hold back her excitement.

  She grinded against him, rotating her hips against his mouth until he choked from the force. When she peaked a flood of woman juices filled his mouth and splashed against his face. Sabrina was in a frenzy of shaking and trembling.

  Any other time she’d be unable to control herself against him and greedily mount his cock to finish her pleasure the best way she could. Now, as his pink pajama bottoms showed a slowly growing spot of moisture in the crotch, she didn’t want to ruin the image.

  Instead she reached back, clutching his hardness under the soft flannel. “How does that feel, princess?”

  He nodded, eyes closed, expecting her to go farther. When she stretched and moved off him, he stayed in position, unable to believe she left him untouched.

  It was a couple minutes before she turned to face him. Too timid to say anything, he hoped the expectant stare he gave her said enough.

  She knew exactly what he wanted but tonight he wasn’t getting it. “Wonderful date night wasn’t it?” Her voice was already declining as she faded into sleep.

  Unphased, he reached under his bottoms to stroke himself. The sudden movement roused her and she slapped his hands away. “None of that now. Go to bed like a good girl.”

  Any other time he’d have taken offense to her words. In every way, he believed, he was a man. All the times they’d had sex, all the orgasms he’d given her, there should be no doubt. Sure, she may tease him now and again but she couldn’t actually confuse him for a girl.

  Sabrina knew exactly what she was doing and smiled to herself at her boyfriend’s reluctance to say a word. Her plan was working perfectly.

  Chapter 2

  Milo woke before her, carefully tiptoeing around the room to search every drawer. When that didn’t work, he looked under the bed. Still unsuccessful, he checked the closet. She couldn’t have hid it anywhere else. Last he saw them they were in her hands in this room.

  The sound of him rummaging through the closet caused her to open her eyes. Immediately she knew what he was doing but she schlepped out of bed half awake to watch the search.

  She found him bent over, shirtless and wearing only the pink bottoms she insisted he wear the night before. Standing behind him, she could see them pull against the cute cleft of his ass and his firm, round bottom.

  The last time they went out she chose a white silk thong because, she told him, “it shows off the parts that you need to show off.” The bloom in his cheeks and reluctance to look at her after hearing that told her that she’d chosen well. Only when he had slipped into them and was reaching for his pants did she stop him.

  Nervous and still, he relented when she rested a caring hand on his bare shoulder. “Milo dear, look at me.” Slowly he turned until he was looking into the loving eyes of the woman that dressed him. “You know you’re cute, don’t you?”

  Another explosion of red erupted in his cheeks, causing a burst of wetness between Sabrina’s legs. Reaching to hold his chin between her thumb and forefinger, she held him so he couldn’t look away. “You know that, don’t you? Tell me.”

  He nodded quickly. “Yes, I guess so. Ok.” His nervousness was palatable and Sabrina reveled in it. She slapped a playful pat against the full cheeks held in place by the thin thong. “Good girl. Now finish getting dressed. I want to get dinner.”

  Each time she used the term she expected him to fight it, to get upset and correct her, but he did none of those things. He accepted the change that happened between them, even if he wasn’t sure what happened.

  When they were out, if he noticed her driving and opening the door for him he said nothing about it. She chose where they went to eat and even ordered for him. Tonight it was a fancy French restaurant he couldn’t even pronounce.

  “Le Bouchon” she helped him. “It’s a type of restaurant in France.”

  “You’re not going to make me eat snails, are you?” He grinned, though she knew the question was genuine and she couldn’t help but laugh.

  “Not if you behave yourself. Mind your manners and we can have a wonderful dinner.”

  He sat respectfully, hands in his lap, napkin over his knees while she conversed with the server. “I didn’t know you knew French.”

  Another thing she had managed to keep from him. They were learning a lot about each other. “I don’t have a need to use it much but it’s a beautiful language.”

  His eyes were dreamy, gazing at her like he was lost. When the food came she helped him decide where to begin. While she sipped from her Chablis, he began cutting into his quenelles. “Mmm!” He said, surprised. “What made you choose this place?”

  “We have been stuck going to the same places and eating the same things. I think you needed some changes in your life. This restaurant was getting a lot of good reviews and I wanted to try it.”

  That was good enough for him and she watched as he enjoyed each bite. Thinking of him sitting so daintily in his white thong set her off and she began planning for that evening when they returned home.

  Another change she was happy to notice was his passive behavior in conversations. When they were talking he stayed quiet and listened unless he was spoken to directly. If she wanted to speak he would stop and allow her to say what she had to say before he continued. It was a refreshing change from what they used to have.

  That’s how it was on the trip home. Pleasantly full and very happy with the dinner, she rested a hand on his knee, something that was becoming routine for the both of them. He didn’t say a word, but sat compliantly next to her and waited as she went to open the door so he could get out.

  With a hand on his elbow she led him to the front door. She kissed him, pulling him close and forcefully pulling his head to her. This close together he didn’t seem that taller. Though he was two inches taller, now he appeared smaller than he once was.

  “Get up to the bedroom. Don’t take off your panties.” She had to remind him or she worried that he’d forget his place.

  Sabrina took her time following. It felt good, knowing that her sweet boyfriend was taking to his new role so quickly. When he got there he was dressed in just the thong, a thin silk band separating his crack.

  He was facing away, looking out the window, caught in thought. His arms were wrapped around himself and, when she entered, didn’t make a move to greet her. Making the most of the opportunity, she walked behind him and gripped a handful of boymeat hungrily. “There you are, my little princess…”

  He sighed dramatically. “Sab, stop it. I’
m not a girl. I’m not a princess.”

  Her first instinct was to slap him and make him reel from her hand. That would snap him back into place quick. “Did you have a bad night?” She asked, reaching out to stroke one tempting nipple.

  “No but…”

  “And you liked the attention?”

  “Of course I did, but I wanted to say that…”

  Her voice grew over his. “Then why don’t you admit it? Why fight it?”

  “Because, honey.” His voice had grown soft, pleading. “That’s not how things are. You’re the woman and I’m the man and what you’re doing is wrong.”

  She came closer until their lips almost touched. “Because you’re the man you think you get to decide things?” She almost spat out the words.

  “No, that’s not what I meant…”

  It was too late. Sabrina grabbed his wrist and pulled him across her lap. He fell clumsily, finally realizing the situation when he was eye to eye with the bedroom carpet.

  She looked at the cute round bottom in front of her. So often she had gazed at it and grabbed it as they made love. Sure, sometimes she imagined spanking him (who wouldn’t want to spank a butt like this?) but she never really had the chance until now. She soaked it in.

  “Please honey, I’m sorry. Can we talk about this?” His voice was shaky, uncertain.

  She was having not of it. “I’ve let this go for too long. You’ve forgotten your place and I’ve got to teach you what it means to obey. You need to learn respect like a good girl.” She spoke without thinking, the words affecting him just how she’d hoped. She was right; he was a good boy, though she thought he had a long way to go to being the type of person she wanted to date. Things needed to change and this was the way to do it.

  Her fingers smoothed over the soft skin and she wondered how she could have neglected his ass for so long. Round and firm yet soft and so pretty to look at, it reminded her so much of a girl’s ass. It really suited him.

  She expected him to resist more and try to wiggle out of place but he remained subdued, his body hanging limply over her knees. One hand raised, she paused for a second to remember the moment. Then, before he could realize it, she brought it down hard on his backside.