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The Boys Who Wore Panties

by Dennis

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 14 Apr 2009

The Boy Who Wore Panties


Dennis was at his 12th birthday party when he first thought about what it would feel like to wear girl's panties. He was over his mom's knee getting a birthday spanking when he saw one of his sisters friends panties. His head was low to floor because of the spanking he was getting and he could see up her dress. She had on pink satin panties with white lacy trim. He thought they were so cute and even with the spanking his mom was giving him; kinda hard, he couldn't take his eyes off her panties. He thought how soft they looked and wished he could try them on.

“11 (spank) 12(spank) and one for good luck (spank) and a pinch to grow an inch. Ok Dennis I'm done who wants to spank the birthday boy next?” His mother asked.

“I do I do,” said his beast friends mom.

“Dennis, go over to Mrs. Jones and get your birthday spanking young man” his mom pushed him towards her. All the kids giggled getting to see Dennis get spankings even if they weren't real ones.

Dennis ended up getting five birthday spankings by the time the party was over and his bottom was a little sore. When he went to the bathroom he was rubbing his bottom remembering the panties he had seen and thinking how nice it would be to have on some nice soft panties right now.

In the bathroom was the dirty clothes hamper and Dennis got an idea he pulled out the dirty clothes until he found just what he was looking for. What he found was a pair of his sisters panties. She was thirteen and about the same size as him. The panties were light blue nylon with lace trim. They were the softest thing Dennis had every felt and tiny compared to the Jockey shorts he was wearing. He pulled down his jeans and undies and slipped on the panties. They felt so good as he pulled them up his legs till at last they covered his sore bottom. Almost as soon as he felt them on his penis it started to get hard. It felt so good in the panties he couldn't believe how nice it felt.

“Dennis are you in there?” His mother asked from the other side of the door.

“Yea I'll be right out,” Dennis hurried to pull his jeans back on and hid his undies in the dirty clothes hamper. He was amazed how the panties felt barely covering his bottom and penis. He was lucky that his long tee shirt covered the budge in his pants. When he walked out of the bathroom his mom took him outside so they could eat cake. Just walking with his dick rubbing against the panties and the warm tingling feeling from the spanking was turning him on with each step. He no sooner sat down at the table when he felt his dick cum. He almost couldn't move from the feeling spreading all through his body. His panties were very wet in the front now and he hoped it wouldn't show on his jeans.

Dennis lucked out by the time he stood up the wet spot blended in with his jeans and no one knew his secret. When the party was over and everyone had gone home he was helping his mom clean up when she asked him, “Does your bottom hurt? You got about sixty spanks.”

Rubbing his bottom and feeling the soft panties under his jeans he answered, “Sixty-five spanks mom you forgot about the ones for luck.”

“That's right, so does it hurt?”

“Well it hurt a little but not that bad.”

She gave him a smile and said, “Let's see how red you got pull your pants down.”

“MOOOMM no way I'm not gonna show you my butt!” He felt his heart jump to his mouth fearing what would happen if she caught him in his sister's panties.

But his mom was in a playful mood and took him by the arm dragging him to the sofa and playfully pulling down his jeans. She really wasn't looking at his pants as she pulled them down but at his face as he yell, “DON”T MOMMY PLEASE.“Then she felt for his underpants and the look on her face changed and Dennis knew he was gonna get it. She felt soft nylon panties under her hand she look down to see girl panties on her boy's bottom.

“WHAT ARE YOU WEARING YOUNG MAN?!” She yelled standing him up in front of her. He stood there his jeans on the floor and the blue girl panties covering his boy parts. “WHY ARE YOU WEARING YOUR SISTER”S PANTIES?“

Dennis was speechless, “I, ah, well I, they, a, I made a mess in my underpants when I went to the bathroom and I, ah , well I found them in the dirty clothes and put them on. I, ah didn't want to say I had an accident during the party cause my friends were here and a...”

“Is that so well lets just go look at your underpants?” She stood up and dragged him to the bathroom. When they got there she looked in the dirty cloths hamper and found the only pair of boys underpants and they were as dry as a bone.

“I don't see any mess in your underpants Dennis so you're already in trouble for lying do you want to add to the punishment? Now why are you wearing you sister's panties?”

Dennis knew he better fess up or he'd get it worse, “I just wanted to see what they felt like to wear mommy.”

“Take them off right now!” She stood while her son removed his jeans then pulled down and handed her the panties, it was then that she saw the stain in the front of the panties. “Oh my God what have you done in your sisters Panties! You naughty bad boy!” She reached around him and spanked his bottom once hard.

“OOOWWW! THAT HURT!” He rubbed his bottom then said,“I didn't mean to they were so soft that just walking in them made it happen really.”

“Dennis you just wait till your father gets home he is going to give you a spanking you'll not forget for sometime. You go to the garage and get the clippers and go cut a switch and it better be a thick one you know how he likes them.” He started to put on his jeans when his mom said, “Leave them on the floor and go out without any pants young man! No wait.” She took him by the arm and went to his sister's room. She went through one of the drawers in his sister's chest of drawers looking for something. His sister sitting on her bed had heard her mother yelling so she sat there not wanting to get into any trouble herself just watching. At last his mom found what he she was looking for an old pair of panties that were very frilly and pink and would make him look like a real sissy. “Here put these on!” She tossed the panties to him.

“Please mom don't make me go outside in them,” He was almost crying.

“You wanted to wear panties so now your going to wear panties now put them on and get outside and cut a switch and do it in the front yard! Now MOVE!”

He pulled on the panties that fit so tight he thought they would rip. He was so embarrassed but he knew he better do what his mom said or the punishment would be a lot worse. It was bad enough that his dad would spank him for real on his birthday he didn't want one from his mom as well. Just before he was ready to leave the room his mom pulled off his tee shirt and gave him a hard spank to send him on his way.

His sister asked her mom, “What are you going to do to him mom?”

“Father will spank him when he gets home but first the two of us are going to dress him up to be the girl he seems to want to be.” His sister giggled.

Dennis headed out to the garage and on the way the tight soft panties started to work their magic on his penis again. By the time he got to the garage his dick was peeking out the top of his panties. He wanted to play with it but knew he better get the switch cut so out to the front yard he headed.

He went straight to the willow tree to cut his switch as fast as he could hoping no one would see him but then he saw Jack watching him from next door. Jack 13 but not much taller than Dennis said, “Hey Dennis why you running around in girl's panties?”

Dennis had cut a good switch and went over to the fence to talk to Jack; “Well I was naughty and my dad is going to spank me when he gets home and well she made me cut a switch and just to make it worst she made me wear panties.”

“Really you're getting a spanking on your birthday? What did you do to deserve that!”

“Ah..I,” Dennis didn't want to tell him but then Jack saw his boner.“

“Wow I see you like your panties! I get real hard when I wear my sisters panties,” Jack said.

Dennis was shocked when he heard what Jack said, “You wear your sisters panties?”

“Yea I really like the way they feel,” he look at Dennis's boner, “apparently so do you.” What Dennis didn't know was that Jack was getting a boner just seeing Dennis in panties.

Dennis decided to tell Jack the truth, “I got caught wearing my sisters panties and when I took them off my mom saw that I had cum in them that's why I gonna get a switching also I lied to her.”

“Oh, too bad man, well sometime we'll have to put on panties together.”

While they were talking Dennis's mom had come out to see what he was doing, she saw the two boys talking and they didn't see her as she walked up to them just in time to here the last thing Jack had said.

“So you like to wear girl's panties as well!” She stood with her arms crossed glaring at the boys. “Both of you come in the house now!” She stood and waited till both boys had walked past her then she gave her son a spank to move him along.

When both boys were inside the house mom said, “Dennis go to the garage and clean up your switch then get back in here and make it fast!” Dennis ran out to the garage. Turning to Jack she said, “So you like to wear girl's panties like my son, pull your jeans down young man!” Jack knew better than to hesitate he'd been spanked by her before he un-buckled his belt, un-buttoned and un-zipped his jeans and pulled them down. What was reveled was a pair of lovely power blue with lacy trimming panties. They fit very tight so his bottom was very clearly defined.

“Well, well, well they are very pretty and make you look like a big old sissy boy I think I will give your mother a call you take off your shoes and jeans and tee-shirt and go stand it that corner. He did as he was told while mom went to call his mom. Jack knew he was in for it he was sure as soon as his mom found out she'd search his room and find all the other panties he had, he was screwed.

Meanwhile Dennis was cleaning off the willow switch and making it nice and smooth he knew it was going to sting like hell when his dad used it on his bottom. He could already feel the welts it was bound to leave on his bottom. He wondered if Jack would get it too he had seen his mother spank Jack before with a hairbrush when she babysat him and had enjoyed the view of his bare butt getting spanked but today he wasn't so sure he'd be enjoying anything about the up coming spankings.

Talking on the phone to Jack's mom, “ then I told him to take down his jeans and do you know what he has on? Blue panties with lace trim...ya power blue....really! Well I plan to put Dennis in a dress and blouse and stockings and makeup for the rest of the day, and when his father gets home he'll get a spanking...sure we can do up Jack as well,...I'll dress him and Jim can spank he as well when we send him home you can keep the clothes for the next time he needs to be made into a sissy,.. right I'll talk to you later bye now.”

Outside Dennis was just finishing up the switch getting it nice and smooth, he knew this one was gonna hurt a lot he maybe should have pick a thinner one.

“Jack I just talked to your mom and she wants me punish you as well.” She left the room and went to her daughter's to let her know there would be two for dress up.

At last Dennis came in with the switch he placed it on the coffee table then went to the corner to wait for his punishment. Both he and Jack knew not to talk while in the corner as that brings extra spanking.

“Well at last two pantie-boys standing in corners waiting for punishment. Boys it's time for the start of your punishment come with me please.” She led the boys to her daughter's room and there on the bed were two sets of girl clothes.

“Dennis, Jack since you too seem to like girl panties so much we are going to dress you up like two cute little girls for you spanking. Dennis you come here and I will help you get dressed, Jack Diana will help you.”

The boys were not at all happy but they both knew better than to disobey so soon they were getting to look more like cute little girls. Mom and Diana dressed the boys up to look like the cutest sissy boys on the street. They were fitted with training bras stuffed with tissue paper. Both boys were quite embarrassed but turned on at the same time. Jack the most having Diana who he thought was hot being the one dressing him. Next they were helped into tights, Pink for Jack and power blue for Dennis. Then a pretty blouse and jumpers then mom put makeup on both of the boys, lipstick and some color on their cheeks and eyeliner. Lucky for both boys they had nice long hair that was easy to put into girl styles dos' with bows.

“My,my,my look at my new daughter and his girlfriend from next door, they are just adorable!”

“Oh yes Mommy they are so cute can I play tea party with them?” Diana asked with a big smile.

“Well Diana maybe another day they still need to be spanked, remember? Now girls, talking to the boys, go stand in the corner in the living room and wait for father.” The boys went to the corners they hnd stood in before and waited for the spanking to come. Both boy's faces were flushed pink from embarrassed but they were both very turned on as well. As they stood in the corners they both had boners in their panties. Jack just couldn't stand it and started to rub his boner against the soft panties planning to stop before he came but before he knew it he felt his panties getting all wet and sticky. He looked over and Dennis and saw he to had the same problem.


Not long after they both messed their panties the front door opened and father came in, “What the hell is going on!”

“Oh hello Jim,” she kissed her husband, “Don't Denise and Jackie look cute?”

Father looked perplexed his wife gave him a wink and explained, “Well I caught Denise in a pair of Diana's panties after his birthday party and when I asked him about it he lied.”

“He lied?, Young man you know lying is an automatic spanking, did you forget?”

“I'm sorry daddy please don't spank me please.”

“Too late for that young man, or should I say lady?” Turning to his wife, “why the dress?”

“Well when I made him take off the panties I found he had masturbated in them...”


“Yes so I put him in clean panties and sent him outside to cut a switch for you to use on him and while he was there I overheard him talking to Jack and about wearing panties. It turns out that Jack was wearing panties under his jeans and when his mother found out that he was wearing the very panties she had been looking for she ask us to punish him with Dennis I mean Denise. So I decided that since they both like girl's clothes they should get dressed up completely.”

Now that father was up to date it was time to warm a couple of bottoms, “Both of you, ah, girls get over here!”

The boys slowly walked over to where father was standing waiting for them. “Since you two seem to what to be girls I guess I'll have to spank you like girls, Denise go get your mother's hairbrush.” Denise walked slowly towards the stairs, “RUN YOUNG LADY!” He took off at a full run up the stairs and back with the hairbrush in hand.

Father sat on the big wooden chair he used mostly for giving spankings he patted his lap and said, “Get over here Denise.” Denise walked to his dad still holding the hairbrush when he offered it to his dad father said, “Just hold on to it and think about how it will feel when I spank your naughty bottom with it young lady!” Then he pulled Denise over his knee and moved the dress out of the way, rubbing his son/daughter's pantied bottom he said, “What nice pretty panties too bad they are so thin.”

SPANK SPANK SPANK SPANK “OOWWW AAAHHAHAH OOOUUUCCCHHH!” The spanking had begun. Denise felt his bottom getting spanked hard one cheek then the other top to bottom soon his whole bottom was stinging and burning.


The spanking went on till Denise was crying good then the panties were pulled down and father said, “Give me the hairbrush!” Denise had barely held onto it but knew he'd get extra if he had dropped it, he handed it to his dad.

SMACK “OOOUUUCCCCHHH!!!!!” SMACK “AAAWWWWWWWWWW!” SMACK the hairbrush paddling went on for about 100 smacks Denise was crying so hard he had gone a bit limp. His bottom was as red as an apple and the panties had flown across the room from his kicking legs early in the paddling.

“Get up Denise and go get you panties!” Denise got them and handed them to father, it was then that he saw they were wet with cum. “WHAT THE HELL! Did this happen when you were over my knee?”

“No daddy it happened when I was in the corner I'm sorry.”

“Oh you will be! Put them in your mouth and get back over my knee!” SO Denise put the panties in his month and got back into position for another spanking.

SMACK SMACK “OOOWWWWWWWWW!” The hairbrush smacked hid bottom another 100 spanks! More tears and muffled crying came for the well spanked Denise. His dad let him up saying, “Now go stand in the corner, Jackie your next come here!”

As Denise went to the corner Jackie started to move towards the spanking he feared so much that he stopped half way there. He had watch Denise get it and even got a hard on watching but now that it was his turn he got real scared.

“Jackie don't make me