James to Jamie by Lucitta

Jenny was typical as well. She played soft ball, went to dances, and while she enjoyed attention from guys, she never got around to dating them.

I don’t recall everything that lead up to it, but growing up I found myself uncomfortable. I didn’t make many guy friends, and my girl friends would, not on purpose, put me on the outside of the circle. They were friends, and I was the friend of their group, more than anything.

I didn’t know the words for it back then, but I wanted to be better friends with them, or at least feel what it was like to be one of them.

That’s how I found myself in my sisters room. She was babysitting for the evening, and my mother was out on the town.

I had undressed in the bathroom, and leaving all the doors open between myself and there, began to go through my sisters closet.

Going through the items I picked out a baby blue tank top, much softer than anything I would wear, and a frilly, dark pink, skirt.

Setting them aside I went to her dresser. Opening the top drawer I found a ***********ion of bras. Sorting through them I picked the black one, with pinkish red lace flowers around the cups. Going down a drawer I found her panties, bikini on the left, thongs on the right, and assorted in the middle. Pulling out a bright red thong I quickly figured out it wouldn’t work with my assets, and I exchanged it for a black pair of bikini cut, with matching pink and red lace around the trim.

Feeling the panties in my hand, they were soft, smooth. The lace was a little rough, but so light as to tickle more than scratch, if anything.

Sitting on the side of the bed I rub the underwear between my fingers, before bringing them up and nuzzling my cheek in to them. Soft.

Picking up my feet I slide the panties up, tucking my penis back to make them fit. They were snug, but comfortable.

Standing up and walking to my sisters mirror I turn around, looking at my butt. My cock gives a slight twinge, and I see the fabric bulge.

Returning to the bed I begin my fight with the bra. Putting my arms through the loops and reaching behind me I fail to clasp it. Turning it around, backwards, I clasp it in the front before moving it back again, and replacing my arms. Feeling the empty cups protrude from my chest both felt right, and wrong.

Returning to the dresser I pull two sock balls from the bottom drawer, and fill my bra. Much better.

The skirt goes on easy, probably sideways. Without tags, pockets, or a zipper, I have no idea how girls figure it out. Returning to the mirror I look at myself from behind again. Wiggling my butt I love how the fabric dances around. Bending forward, touching my toes, I can barely see the hint of my black panties peak out from the longer than desired skirt. Again, the fabric bumps as my erection is now straining at the panties gusset.

Returning to the bed for the second to last time I slide the soft tank top over my chest. The straps fit comfortably on my shoulders, not putting any weight of the draped garment around my neck. Looking down my bra can faintly be seen through the light weight fabric.

At the mirror I feel my breasts, breasts, not socks. They don’t feel like real breasts, but they feel like mine, giving me the thought that I should have breasts, these aren’t natural, but I should have natural.

Sticking out my butt I run my fingers over the skirt, feeling how it flows off of me. Pushing it in I feel my panty lines, and begin to grope myself. A finger pushes the silk towards my crack, the pressure making me groan.

I crawl on to Jenny’s bed, laying on my stomach, with my knees tucked under me. Reaching under me I feel my penis through the fabric. Flipping the skirt, and pushing the panties aside, I let it free.

With just a few strokes I am already approaching orgasm. Not wanting to leave proof of what I did, not easily found proof anyway, I quickly reset the panties over the tip of my cock, as I reach climax.

The panties don’t do much to contain the mess though, and my panties quickly get saturated through, making my hand sticky. With a few squeezes of the tip I sit back, mind spinning, guilt rising.

In a few moments I undressed, returning the tank top to the hanger, putting the bra back in the drawer, socks two more down, and fold the skirt back to where it belongs.

I slowly pull the panties off, using the crotch to wipe my dick off, before returning to the bathroom, panties in hand.

I shower, wash the panties with me, and sneak them, after ringing out, to the bottom of my sisters clothes hamper, hoping she wouldn’t notice them.

While I wasn’t this bold again for quite a while, I did frequently indulge this side of me. I wasn’t sure what this side was, but I didn’t see the harm in letting it out.

I began doing the laundry more often, for both of us. Before doing a load I would go in to her room, put on a dress, or leggings, or booty shorts, always her panties, and look at myself, feel myself, and make myself cum to the feeling. It would always vanish after, but in the moment it felt right.

Things continued in this manner for a few months, until I get hit by a cold. I was still doing the laundry, and taking care of myself before hand, however I didn’t have the energy that day.

I went in to her room as usual, I found myself in a pair of black and red checkered panties, and a comfortable pair of black leggings.

I tried to satisfy myself, but no matter what I did, how I felt myself, or what thoughts I put through my mind, I could not get myself hard. I just didn’t have the energy.

Not wanting to give up, I took the dirty clothes hamper and kept Jenny’s clothes on.

The laundry was going, I had eaten some crackers, and drank some milk, and I was done. Getting back upstairs I close my curtains and bedroom door, and took a nap.

My phone woke me up about an hour later, telling me to rotate the laundry.

Crawling out of bed I make my way downstairs. Jenny is home and I ask her if she had a good day.

Giving me a confused look she responds “It was good, nothing too eventful, how about you? You look like you’ve had an interesting day?”

“No, I had a snack, started laundry, and took a nap.” I replied. “Now I need to go put the clothes in the dryer, then back to sleep.”

After I finish downstairs and return to my bedroom I check my phone.

Text from Jenny: “You should wear leggings more often, they look good on you.”

At first I was confused, then I looked down. I had never changed out of her clothes.

A knock on the door startled me. “One minute!”

I was too slow, as Jenny peaked around the corner. “So, you’re still wearing my clothes, huh?”

“What? No.” I turn as red as the squares on my underwear. “I was tired, I thought they were pajama bottoms.”

Tilting her head sideways I got the impression that she didn’t believe me. “Okay, whatever. I don’t mind, but I need those leggings, give them back, please.”

“I’ll bring them back to …”

“Now, James.” she came fully in to the room. “I’ll wait.”

“I don’t want you to see…”

“I don’t care, James, just give me my leggings back.”

Looping my thumbs through the waistband I slowly begin to pull them off. Trying, in a split second, to decide if I should keep the panties on, and hope she doesn’t mention them, or try to smoothly hide them in the leggings, pretending they were stuck in the pants leg and I didn’t notice.

Committing to the second plan I quickly realized I made the wrong choice.

“Really?” Jenny asked. “My panties too?” She snatched the leggings and panties from my hand. “That is not cool.” She began storming off.

“Please keep this between the two of us. I won’t do it again, I promise.” I grabbed her arm.

“Why are you wearing my panties, James?” She turned to face me.

“I, I don’t know. They make me feel nice.”

‘Nice?” She questioned. “Like, sexy nice, or what? You’re not being very clear.”

“Well, kind of.” I let go of her arm. “They make me feel comfortable, like I can be me, like when I’m dressed in your clothes I don’t have to wear a mask.”

“So, this isn’t the first time, not even close, is it?”

“No, I’ve done it a few times now.”

“Well, this isn’t cool, dude. I’m okay with you trying on my clothes, but my underwear are off limits.” She put on a stern face. “If you want help with this, I’m here for you, but don’t touch my panties, James. Or my bras come to think of it.”

Wanting to be done with this conversation, so I could go die, I apologized again and told her it wouldn’t happen again.

The next morning it was just the two of us at the breakfast table, mom had left early for work that day.

“So, what have you tried so far?” she asked me. ‘I know you tried on my skirt, a long time ago, and I saw the leggings, but what else? What do you like?”

“How’d you know about the skirt?”

“Dude, you literally came on it and put it back. It was kind of hard to miss. I was hoping it was a one and done deal though, but it looks like I was wrong. So, skirts, dresses, skinny jeans, what’s your fancy?”

Blushing I walk her through what I’ve tried on already. A variety of skirts, ranging from full length heavy fabrics, to her shortest date night skirt, assuming she ever went on one. I tell her about the jeans, and how I have a hard time getting comfortable in them, before talking about leggings.

“Tops?”

I tell her about the blue tank top, and how lovely it made me feel, followed by a variety of patterned T-shirts, a few jackets, and her favorite purple knit cap.

She nodded along, eating her fruit, and listening intently.

After the dishes were washed and put away Jenny told me to give her some time and to meet her in her room.

I clean the table, counter top, and push in our chairs, then go to her room.

“Okay, time for you to get dressed.” with her chin she pointed to the bed. ‘Pick an outfit.”

On the left of the bed was the frilly pink skirt I had worn the first time, under a mint green short sleeve shirt with an outline of a bunny head. To the right was the baby blue tank top I had warn with the skirt, and under it was a pair of peach shorts.

In the middle was a of black mid length skirt, paired with a pale orange tank top and light blue cropped vest. I walk to the bed and pick that outfit.

“Good choice, now get dressed.”

I began gathering the clothes, but Jenny stopped me. “No, here. I already saw you naked, so just do it here.”

Nervously I take off my pajama shirt, before facing away from my sister and removing my pants.

Still facing away from my sister I quickly pull the black skirt up. Turning me around Jenny looked at my crotch.

“What?” I ask while looking down.

My habit had gotten the best of me, and my body assumed that girls clothing meant masturbation time. Without wearing any underwear my erection was pushing against the skirt, bulging out.

“Well, that is a little obvious. Take care of it.”

“What?”

Gently pushing me to the bed, my sister lifted the skirt. “I said, take care of it. Make it go away.. Masturbate.”

“I can’t with you watching.”

“Fine.” She turned around, facing the foot of her bed. “Go ahead.”

“Can I go to the bathroom?”

“No.”

Laying back I gave in to my fate, and began stroking myself. My eyes were closed, I was picturing myself fully dressed, feeling my breasts, rubbing my crotch, and getting in to jacking off.

Opening my eyes for a moment I saw my sisters reflection in the mirror. She was still in her pajamas, hand pinched between her thighs. Was she masturbating too?

The thought of being so close to a masturbating girl thrilled me, and I began rubbing faster, as did she. Letting my hand start gliding over the tip I turned to face my sisters back proper.

Reaching out I grabbed the back of her top and pulled her on to the bed. Letting out a shock of surprise she looked at me, knowing she was caught.

I smiled at her, and she returned the gesture.

I continued pumping, as she continued rubbing herself, hand now down her pants.

In a few moments I heard her squeaking, and felt the bed shake as she bucked her hips up to push her clit in to her fingers.

After she climaxed I rolled to face her, and continued jacking off. “I’m close.” I said.

“Do it, cum.” she cheered me on.

“Where should I cum?” I asked.

“Where do you normally cum when you’re dressed like this?”

“Your panties.” I tell her honestly.

Without hesitating she pulled her pants off, followed by the light blue seamless bikini cut panties she was wearing. Sitting up she held them by the leg hold, open, holding them so I would cum in their crotch.

A smell of sweat filled the air, and if I had been more experienced, or experienced at all, I would have known it to be the smell of her. With a few deep breaths I came, shooting ropes of cum in to her panties, and on to her hands.

“Sorry.” I tell her. “They were too far away, I couldn’t get it all in there.”

“No worries.” she smiled at me, wiping the cum off herself with the panties. “I guess you can use my panties still, sometimes, but let me know so you don’t steel a pair I need, okay?”

I agreed and with my deflating penis I continued to get dressed. Not having any underwear appropriate for the outfit Jenny let me borrow a pair of navy blue boyshorts.

She put on the pink skirt outfit, and we took some time looking at ourselves in the mirror.

“Are you ready?” she asked me..

“For what?”

“Well, while I don’t mind you wearing my clothes, much, I think you should get your own. So today, James, Jamie, we’re going to go shopping.”