Playing Dress Up with My Cousin

By NAMB

* * * * *
This story is intended for adults only. It contains depictions of forced nudity, spanking, and/or sexual activity of preteen and young teen children. This is fantasy, and the author in no way endorses or practices these things on real life. If you are not of legal age in your community to read or view such material, please leave now.
* * * * *

Playing Dress Up with My Cousin

It started for me when I was about 9 years old. I was at my aunt’s house visiting my girl cousins... Samantha, better known as ‘Sammie’ was 7 at the time, and Madison who was 13. Our moms had decided to go shopping and left Madison in charge to watch us younger kids.

I liked Madison a lot. She was an intelligent, active girl with a positive attitude and very confident. She also is very pretty, a fact that, even as a 9-year old, I could appreciate. She had a starring role in many of my fantasies and dreams. Sammie is very much like her in both attitude and looks, and over the years has become increasingly attractive.

On this particular occasion, the weather was bad and we were forced to play inside the house. This would have been okay except that Madison was a ‘grown-up’ and didn’t have any toys of interest, and Sammie only had ‘girl toys...’ Dolls and princess outfits.

Sammie and I often played ‘house’ and ‘school’ and other role-playing games using her dolls as either family members or students. She liked being the mommy or the teacher and the person in charge. In these games, I was usually the ‘daddy’ of the house, but also sometimes young boy of the house. However, when we played school, she enjoyed the role of strict teacher and found reason to be displeased with my performance and scold or punish me for it. This punishment consisted of a lecture and corner time for me.

Sammie and Madison were playing ‘dress-up’ with Sammie’s dolls. I don’t know if Madison was humouring her younger sister or reliving a girlhood memory. I just couldn’t get into that activity. Changing clothes on a doll didn’t do a lot for me. It amazes me that even pre-school girls can get off on clothes.

After a while, even the girls tired of this activity, so Madison got a new idea, “Let’s use Alex. He can be our doll. We can dress him up.”

“What?” I protested, “I’m not going to do that. It’s crazy!”

“It’s not crazy... There’s nothing wrong with it. Girls and boys do it all the time. Come here, I’ll show you...” She brought up the computer, went to YouTube and queried, ‘makeover’ and ‘brother.’ Dozens of videos came up. Page after page... It seemed that sisters and other female relatives liked to dress boys up as girls. The girls giggled as they watched the videos and although I was uncomfortable with seeing boys treated this way, I sort of got used to it. For one thing, the boys didn’t seem to mind and the girls were having a fun time.

I relented. I wasn’t doing anything else and at least this gave me a chance to participate in some of the play. I only had one condition...

“I’ll play... but I get to keep MY underwear on...”

“Of course, Alex,” Madison agreed. But I noticed that Sammie looked disappointed.

Once the girls got into it, it really wasn’t that bad. Madison got a blond wig she used as part of a Halloween costume and did it up in pig tails as it sat upon my head. She and Sammie spent a lot of time going through Madison’s ‘hand me down’ collection, looking for clothes that might fit me. Shoes were not an issue since I wore the same size as Sammie...

The girls had a great time putting clothes on me and taking them back off. I was ordered to stand still most of the time as they fitted the clothing to me. My role was almost completely passive and I moved only under the girls’ orders when it was necessary to get an article of clothing on or off my body. I did feel like a doll that was being posed by the girls and I decided to go along with it and play my part.

The floor was strewn with Madison’s old clothes by the time they finally settled on an outfit they liked.

Madison and Sammie stood back to admire their work. “Doesn’t he look sweet?” Sammie said.

“Doesn’t *SHE* look sweet,” her older sister corrected. “Come,” she said, taking me by the hand and leading me to her room. “Let’s finish you up.”

When we got to her room, I looked at myself in the full-length mirror on the back of her door. A familiar-looking girl looked back.

Madison gave me only a moment and then sat me in front of her vanity. “No girl is complete without a makeover,” she proclaimed.

Sammie, didn’t have her own makeup and her mom touched her up with the barest amount of lipstick and blush when she was wearing her ‘Sunday Best’ for special occasions.

Madison, on the other hand, looked like she had a complete beauty parlour in her room! She used it well. Unlike many other girls (and some women), she didn’t overdo it with the makeup. I got to see her on many occasions without the makeup on. I don’t know why she bothered, she looked stunning enough without it.

I felt like I was in the laboratory of a mad scientist, surrounded by equipment and chemicals of unknown purpose. I knew girls wore lipstick and nail polish, but I didn’t have a clue what the rest of the stuff was for. I found out as the girls wiped, swiped, painted, smeared, soothed, dusted, patted and did all kinds of other things to my face. Madison seemed to delight in showing Sammie how to use the various implements to apply it all.

When she was done, Madison spun me around in the chair to face the mirror on the vanity. I looked and I was surprised. The family resemblance was there and except for the hair colour, I could have passed for the girls’ sister. I really did look like a girl!

What more could they do to me? Madison had the answer to that. “Now that we ‘put on your face,’ it’s time to give you your manicure and pedicure.”

Sammie was invited to help paint my nails. All 20 of them! I never really took a lot of notice of women’s feet, but I do recall that some have nail polish on their toes. I don’t know why they did that when a lot of times they are covered up by shoes.

This seemed to be a time-consuming process and even I giggled as I looked down at balls of cotton wedged between my toes. The rest of the process, well, have you ever heard the expression, “as exciting as watching paint dry.” Fortunately nail polish does dry fast especially when you have two girls fanning it with makeshift fans.

“Now that we have you looking like a girl, it’s time to teach you how to act like a girl. Let’s see how you walk down the hall.”

The girls giggled at my performance. “You walk like a potato farmer. You’re taking huge striding steps like you’re was stepping over the furrows in the field.

A girl doesn’t walk like that. She takes smaller steps and she swings her hips like this ...” Madison said, as she demonstrated. I looked at her rear end as it moved hypnotically away from me. I found it fascinating and made note to watch girls walk in the future.

“Now you try,” Madison challenged.

I just couldn’t get the hang of it. So, Madison had another idea. She had me stand in front of her. She took a tennis ball, raised my skirt and pressed it between my legs.

“Ummmmmph...” I gasped with shock and some sort of discomfort that somehow piqued my curiosity as she pressed the ball against my real balls.

“Sorry, did I hurt you?”

“No, not really. It’s just sensitive there and you took me by surprise”

“Now walk around with the ball between your legs like that...”

I practiced for a while and it felt uncomfortable. I was glad I was not wearing high-heels. I was wearing a pair of Sammie’s open-toed sandals that showed off my pretty nails.

All this preparation made me wonder how women and girls ever get out of the house. I was glad I was a boy. I take a shower, dry my body, drag a comb through my hair, throw whatever clothes are readily available on my body and I am out the door 5 minutes later.

At my age, I didn’t even have to shave and never whole legs, underarms and wherever else girls grow hair they don’t want.

I was just getting the hang of “shash-saying” as Madison described my feminine walk, just as our moms returned from shopping.

“Guys, we’re home...” my Aunt called up the stairs... “Did you kids have fun? Do you want some lunch?”

“We sure did, mom...” Madison called back with excitement. “We made a new friend, Alexis. Do you want to meet her?”

“Um, of course. But you know you weren’t supposed to have anyone over while we were gone.”

“It’s just Alexis. You’ll see. She’s okay, really...” She turned to me expectantly and said, “Show time!” As she began to usher me towards the door and my big revelation to my Aunt and Mom. Madison cautioned me in a low voice, “And don’t ‘lay an egg’ with that tennis ball.”

We descended the stairs and as soon as our moms caught sight of us, they laughed, but went along with the game...

“Where’s Alex?” my aunt asked.

“Your friend is very pretty,” my mother put in.

“Come, let’s have some tea like proper young ladies.”

I spent the rest of the afternoon dressed like a girl. We discussed ‘girl things’ over tea, and I liked being included in the ‘girl talk.’ I learned a lot about girls as they talked... Boys just didn’t have conversations like this. It was clear to me that girls used vocabulary better than boys... They talked about things with passion and detail and civility... way better than when I talked with my own friends back home. Boys mostly grunted and fist pumped. We acted more like a troop of baboons than civilized humans.

When it was time to leave, I felt remorse as I shed my female clothing, took off the wig and washed my face. I needed the assistance of the girls to remove the nail polish... As we left, my aunt asked,

“Did you have a good time?”

“Yeah, that was fun... I guess,” I replied, sounding neither too keen or disinterested.

It was also educational. I got a little insight into what it is like to be a girl. It made me feel funny to be one even if only for a few hours. I also thought that my alter-ego, Alexis, was an interesting person and I wanted to get to know her better.

-=o=-

From then on, whenever I went over my cousins’ house, I tried to get them to play dress-up with me. Madison had no interest now that the novelty of the event had worn off. For her, it was a one-off: a game to play with her kid sister on a rainy day. She was a teenager and had interests far beyond my comprehension.

I could still interest Sammie, but both of us figured that our moms would not approve if we did it all the time. So we started doing it in secret. Madison caught us a couple of times, but she never told anyone.

As we got older, even Sammie lost interest in playing the game. Her dolls now sat on the shelves, no longer played with, but there for display as a reminder of her childhood.

Sammie was not a child anymore. She was now going into middle school and was a “tween:” more interested in clothes for herself than for her doll collection. It became increasingly difficult to get her to dress me up. Even she was beginning to think that it was just a bit weird.

Then one day, she actually suggested playing dress up, but she changed the rules...

“This time, let’s do it for real. I’m going to put you in my undies and you’ll even get to wear my bra.”

I didn’t have an objection to the bra really... Like the skirts Sammie sometimes dressed me in, they were kind of traditional, ‘real girl clothes.’ Properly girlish and totally different from what I would wear as a boy. It didn’t excite me as much when she put me in her or her sister’s shorts... Boys wear shorts too, even if they’re not pink and don’t have lace on them.

But Sammie’s panties were something else. Panties are uniquely feminine and they touch a girl in her most sacred spot.

“I c-can’t wear your panties.”.

“Why not? Don’t you like them?”

“They’re nice and they’re very pretty... but I’d have to take my underwear off to get them on...”

“So?”

“So...” I mimicked her a little to emphasise my point. I thought it was obvious. “Y-you’ll see me.”

“Well I’ve got news for you!” Sammie scoffed... even giggled. “Those underpants you wear don’t leave a lot to a girl’s imagination you know?! I’ve seen how much bigger you’ve gotten over the past couple of years. It’s about the only thing that kept me still playing with you...”

“And besides...” she continued calmly. “I know what boys look like and I think it’s time ‘to up the stakes’ in his game. If we are going to continue to play it, then we’re going to do it by MY rules... and my first rule is, that you take your underpants off and put mine on!”

I had noticed that Sammie was getting increasingly bold and bossy over the past year, but never had she spoken to me with such a level of authority. Not even when she was the mommy in our games of ‘house’ or the teacher in our games of ‘school.’ I was already down to my underwear in preparation for the game and had removed my top to try on the bra...

I was suddenly aware that I was only one piece of cloth away from total nudity in front of her. I pulled down my underwear and stepped out of them. Sammie looked at me with interest but said nothing. She handed me her panties and I stepped into them.

They felt so silky going up my legs and when I got them to my waist, I felt uncomfortable. They didn’t cover as much as my underwear did and what little room they had was not designed for the male anatomy. My balls were pushed up against my body and there was no place for my penis to go except sideways or up so the head peeked out over the lace on the waistband.

I’ve always liked the feel of girls’ clothes on my body, but the bra and panties were the ultimate in girls’ clothing. My penis was getting hard and there was nothing I could do to stop it. There was also nothing I could do to hide it either. In the past, I did my best to adjust it so it would lay aside my leg and used the skirt or whatever I was wearing to hide it. The skimpiness of the panties didn’t offer any way of concealing it. It was open and it was on display for Sammie’s eyes to see. There was nothing I could do but stand there and blush.

Sammie did not seem too eager to continue the game either as she stood there and took in the sight.

“We better get moving...” Sammie eventually said. “Madison will be back from her job soon.” Sammie dressed me in an outfit I had worn before, but this time I felt more girlish with the proper garments on underneath. I was hard the entire time.

When the game was coming to an end, Sammie helped me undress and put the clothes away. As I lowered the panties in front of her, my penis was standing rigidly out in front of me. The front of the panties were wet with precum.

“Wow!” Sammie giggled, unable to take her eye off my ‘thing.’ “I’ve never seen one that hard before...”

Her response kind of made me wonder... ‘How many boys has she seen and how many of them were hard and why were they hard?’

Her explicit talk and the raw sexuality was getting to me. The urge to masturbate was overwhelming...

“S-Sammie,” I grumbled... “I was wondering if you would mind if... y-you know... If I could do it...”

“Do what?”

“J-jerk off. I can’t stand it anymore...”

“Oh... well... that’s okay...” she replied quickly. “I was going to ask you to do it anyway. Just, don’t make a mess, okay?”

Again, she had me wondering about how she knew about jerking off or that when boys did it, they made a mess...

I only got the first couple of strokes in when we heard the sound of an old car in the driveway.

“Oh shit!” Sammie gasped. “Look at the time. That’s Madison, she’s early today. Get dressed, quick!”

I had just about managed to do that by the time Madison got in the house and was passing by Sammie’s room. She popped her head in and said,

“Hi Alex, what are you doing here?” Turning to her sister, she said, “You two haven’t been playing again, have you? <giggle> I thought you’d be getting too old for that now.” Neither of us said anything, but we sure looked guilty and sheepish... So, Madison continued... “Well, it might be a bit pervy, but I don’t see where it’s hurting anyone. Just be more careful; don’t let mom catch you doing it.”

The whole time she was talking to us, she barely looked at us and was looking at the pile of clothes on the bed. It wasn’t until she left that we both looked back to see that on top of the pile were the cum-stained panties I just wore...

“Wow, that was close,” Sammie said.

“If I don’t cum soon, my balls are going to burst...” I whined.

“I’m sorry, but we can’t do anything about that now. I really want to see you do that, but Madison’s a great sister and I love her. She’s been good about looking the other way all these years and even now, but I think even she has her limits on what she’s willing to let slide.” She quietly laughed at the saddened look I had on my face. “Suppose I can arrange for something tomorrow?”

“How are you going to do that?”

“Let me work out a couple of things. I’ll give you a call.” She gave me a kiss. “Now you better go before mom gets home. Madison might be understanding, but mom is another story.”

I got a call later that night...

“Hello?” I answered quietly to avoid arousing suspicion.

“It’s set,” Sammie’s voice said in response...

“What’s set?”

“I’ve made arrangements for us to play again tomorrow.”

“But h-how?” I asked with curious excitement.

“Just be over here at 1PM... AND I expect you to save yourself for me, if you know what I mean?”

Well of course I knew what she meant... but how did SHE know what she meant?

-=o=-

I spent the night in a restless slumber. Partly it was because of the anticipation of what Sammie had in mind and partly it was because I did not relieve myself and exhausted myself fighting off the urge to masturbate...

I spent the morning around the house doing busywork to keep my mind off my now-overfull testicles. Mom even noticed...

“It’s nice that you are getting ahead on your chores,” she remarked.

“Well, I decided to do them while I had the energy and not wait until you nag me!” I replied smartly with a playful laugh. The irony of what I had just said!

“Well that’s a very sensible thing to do...” my mother replied with a laugh of her own.

One o’clock approached and I was out the door like the house was on fire. I got to Sammie’s house and rang the bell. She met me at the door and didn’t even invite me inside. She grabbed her back pack and eagerly pushed by me and led me by the hand...

“Come with me...” she instructed.

“Wh-where are we going? What’s with the back pack?” I asked.

“You’ll see.”

We walked a couple of blocks and went up to a house. She rang the bell. A girl answered the door. I recognised her. She was one of Sammie’s friends... one of Sammie’s better-looking friends.

“Alex, this is Julie. Julie this is Alex,” she said in the way of introductions.

“What is going on?” I asked.

“Come inside,” Julie beckoned with an excited smile.

“Julie is my bestest friend... ever!” Sammie announced as she began to explain the situation. “We share everything... I told her about how we used to play dress-up. She thinks it’s neat that you are nice enough to play with me that way... I told her about my plan to get you to wear my panties too...”

“What!?” I interrupted. “No way! Don’t tell her that. That’s a secret. Nobody is supposed to know that!”

“I told you... we’re bestest friends,” Sammie replied with some anger in her voice. “I tell her secrets and she tells me secrets. She grew up with an older brother. He’s now in college. So she knows a lot about boys. Listen... what I told her about you is really quite tame compared to some of the things she’s told me... As I said, she already knows about your cross-dressing and is cool with it...”

“Cross-dressing!?” That was the first time either of us has mentioned it. Until now, we preferred to use the much tamer term, ‘Playing dress-up.’ Nonetheless, I felt like a chastised child.

“Sammie and I have been friends for a long time...” Julie said, picking up on my nervousness... and not insignificant shame that my secret seemed to be out. “She’s almost like a sister to me. Don’t feel bad about it. I think it’s neat. I think you’re very nice to play with her this way. Most boys feel that they have to be macho all the time... There’s nothing wrong with being masculine, but real men aren’t afraid of their softer side. Only special boys are strong enough to do that. You’re a really neat and special boy for doing that.”

I blushed. Julie had disarmed me with kind words... and had softened my mood.

“So what do I do?” I relented quietly, turning my attention to look at Sammie.

“We have a couple of hours... and so I brought some clothes in my back pack... Why don’t we go to Julie’s room and slip you into something more comfortable?”

I knew where this was going and I did not resist... I needed it so, Julie or not I had to do it.

Soon I was stripped down in front of the girls... to my underpants. Julie laughed as I blushed. I thought she was laughing at my modest bulge at first, but no, she laughed at how bashful I was in front of her.

“Oh don’t worry about that...” Julie said, trying to bring her giggling under control. “I’ve seen my brother in his underwear more times than I can count. He wasn’t particularly modest about it either.”

Julie’s interest did go up though... staring between my legs as I got naked and stepped into my girl-panties. Sammie had to help me with the bra. I don’t know how girls manage to clasp those things behind them like that.

The girls dressed me in one of Madison’s old school outfits. It made me blush as I thought of the girls in my class wearing the same uniform and how some of them hiked up the skirt to tease the boys. I was taller than Madison, so I didn’t have a lot of hiking up to do.

“Once Madison stopped going to high school,” Sammie began, “she decided to modify her uniform as a costume. She hemmed up the skirt a bit and tightened the blouse. This uniform would never pass inspection at school.”

Not only did the outfit make me feel like a girl, it made me feel like a naughty girl: the kind that boys talk about with excitement.

Once the girls had me dressed, they were ready for the main event...

“Let’s go downstairs...” Julie suggested. “The tile floors down there are easier to clean up.”

I felt funny walking through the house in my schoolgirl outfit, but I remembered how to swing my hips as I was taught as a little boy – or was that as a ‘girl in training?’

When we got downstairs, Julie pointed to a coffee table and instructed me...

“Sit right there... with your legs apart. That’s it... Now pull the skirt behind you.” Nobody had mentioned masturbation, yet she was setting the stage already... In that position, my panties were exposed. “Now... be a good girl... pull it out, and let the waistband cup your balls...” Julie directed. I obeyed... my heart beating fast in my chest, feeding the blush in my cheeks and the erection poking out helplessly from between my legs.

Julie seemed to know exactly what she was doing and I wondered if she had ever done this with a boy before.

“Don’t you like the nice silky touch of the panties on your balls?”

With a dry mouth, all I could do was nod.

“Okay...” Julie continued to direct me. “Us girls will sit here nice and quiet and watch you do it.” Turning to my cousin she asked, “Are you ready Sammie?”

“Ready as I’ll ever be.”

With a nod toward me, Julie just said,

“Go.”

I wrapped my fist around my organ and was surprised at how hard and hot it felt. I hadn’t even taken my first stroke and precum was already dribbling from its tip. I started stroking it and I could already feel the sexual tension building. I should have shot myself off last night, I still would have plenty of cum to impress the girls today.

I tried to slow down but that only postponed the inevitable. I suppose that if I could stop at this point, that I would not cum; ejaculation would be put off. But I could not stop. Only physical restraints could keep me from pumping away. I had no will to do otherwise.

I tried to linger in this neverland between arousal and ejaculation as long as I could, but I reached the point of no return. The fuse had met the powder. Even if I stopped all stimulation immediately, the explosion would still happen.

My already swollen penis tightened, hot blood surged and pulsed in its veins and I could feel the wave of cum gushing through the shaft on its way to its eruption at the tip.

I fired my first salvo at the girls who screeched and giggled with delight. It never even made the floor as it hit the couch between where the girls were sitting.

Shot number two landed at their feet as they continued to giggle and point...

Wave after wave, pulse after pulse of cum surged from my penis. I pumped and I pumped until even the tightest contracts produced no more than a pearly drop at the opening.

I stopped and I felt like I had just sprinted a marathon. I was glad I was sitting and even then had difficulty maintaining my balance. I began to shiver with the exhaustion of my ejaculations. There was a river of cum, starting at the couch where the girls were sitting and pointing back to me.

Sammie was genuinely concerned for me...

“Come here. Lie down. Let us girls do the clean-up. You look wasted.”

“Th-thank you,” I managed to whisper, and with the girls’ assistance, I lay down on the couch.

I never did see them clean up as I swooned into a sleep. I woke up with a warm feeling around my crotch. I startled awake...

“I’m sorry, it’s me Julie... I thought I’d clean you up a little too...” She held up a pink fluffy wash cloth as evidence and then went back to cleaning the cum off my body and my tingling genitals.

I felt so helpless yet so secure... It was almost like I was an infant again and mom was taking care of me while changing my diaper. I felt a bit of a pang that babies don’t really appreciate what it’s like to have everything done for you...

I recovered and got dressed. Sammie packed up the clothes and we had a snack before we departed. It was all so ‘normal.’

As we walked back, Sammie took my arm. She was beaming...

“Thank you,” Sammie said to me warmly. “That was really great. Julie was very impressed with you... She has a lot of ‘home alone time’ in her house. We can play over there several times a week if you want.”

“I want!” I replied with enthusiasm.

“That’s good. Julie and I know some other girls who would like to see you do it too...”

The thought of other girls seeing me was daunting, but with Sammie’s support I could do it. “Well... if they are as pretty as the both of you, I don’t think that will be a problem.”

Sammie just squeezed my arm tighter.

(End of File)