When I was a freshman in college, my grandmother passed away. My grandfather had passed away a few years earlier, and Grandma still lived in the family house. My school was in the same city, and I lived in a dorm, so I was able to visit her occasionally.
She had been sick for a few months, and while my parents and other aunts and uncles lived a few hours away, my Aunt Peg lived in the same city and helped take care of her.
Now that school was done for the summer, I packed up my things and got a lift to my Grandma's house, where I was going to wait for my dad to pick me up. My Aunt Peg and cousin Jenny had been staying at the house, going through Grandma's things and organizing them to eventually sell the house.
I knocked on the back door and found it unlocked, so I entered the kitchen.
"Hello? Anyone home?"
I heard some noise upstairs, then someone answered "Coming!" and my cousin Jenny walked into the kitchen.
"Hey Greg! Great to see you!" Jenny hugged me tightly.
Jenny was my age and we had been very close all during childhood. Her mom was my dad's older sister, and they were close as kids, and continued to see each other. Jenny had grown from a tomboy into a striking young woman, and today was no exception in her shorts, t-shirt and pony tale.
"Is Aunt Peg here too?" I asked.
"She was, but she had to meet a client, so she left me to sort through the upstairs sewing room for a few hours.
"Ugh, that sounds like fun," I added sarcastically.
"Tell me about it!" She gestured for me to follow her. "Come on, I'll show you."
I set my backpack and stuff on the floor, kicked off my shoes, and followed Jenny to the stairway to the second floor.
My grandma was a seamstress for a living, and when she retired, she converted the two upstairs bedrooms into a sewing room and storage area. As kids, Jenny and I used to play up there among the piles of fabric and dress models. We had fun recognizing fabric that belonged to clothes my Grandma made for the family. "Hey, I have a shirt from this" or "My dad has boxer shorts from this." The rooms were stuffed with clothes on racks or in drawers, and we loved exploring.
Walking up the narrow steep stairs brought back a lot of memories. I hadn't been upstairs in quite a few years, and it seemed much smaller and more cluttered than I remembered.
"Wow! Look at all of this stuff!" I exclaimed. I walked around, pointing to items and taking it all in.
"What is the family going to do with all of this?"
"Since Mom lives closest, she volunteered to do most of the organizing and sorting. Then the family will go through everything and decide who gets to keep what. I've been helping, and we barely made a dent!" she laughed.
I walked over to one of the piles of fabric, and noticed some familiar patterns. "Hey, this is the boxer short pile!" I saw some white fabric with thin red stripes, some more with colorful geometric shapes, and pastels of all colors.
My grandmother sewed a pair of matching boxer shorts for each of the men in the family each Christmas. As I got older, I noticed that there seemed to be some sort of rite of passage that added you to the boxer shorts club. I asked my dad when I could get some, and he told me I needed to be a little older. That didn't make sense, because some of the guys in school were already wearing boxers, and my mom would only buy me white briefs. It seemed like being eighteen was one part of the rule, but there was something else.
"Look what I found here." Jenny walked over to a large dresser with deep drawers and pulled out a white piece of fabric and tossed it to me. I caught it, and saw that it was a bra. I held it up, feeling the stiff lace, and checking out the pointy cups.
"Quite a retro fashion statement! Look at these cones!"
I tried putting it on, but never having worn a bra before, I was having some difficulty with getting it over my t-shirt.
"Here let me help," Jenny offered, and came up close behind me. She slid the bra straps off my arms, then grabbed my shirt at the waist and lifted it over my head. "It needs to go on under your clothes, dummy!"
I was a bit surprised that she had taken my shirt off, but then she slid the bra straps over my arms, and fastened the hooks in the back, adjusting the fit. Jenny reached around the front, and cupped the cones, making sure it was on right.
I turned around, modeling it for her.
"Nice! Let me find something else for you to try on." Jenny went over to one of the closets and looked through some clothes on the hangers, and pulled out a sleeveless dress with big flowers. "This says you all over," she laughed.
Jenny came up to me and held the dress open near my head. I put both of my hands in, and she helped pull the dress down over my head. Not knowing what I was doing, I got all caught up with my head inside and arms peeking out the top. Jenny tried getting the dress down over my waist, but it was snug fitting and hanging up on my jeans.
I was surprised to feel Jenny come behind me and reach around to undo my jeans and unzip them, then pull them down to the floor. I was standing there in my white briefs, with the dress over my head and arms reaching up. My briefs had been pulled down a few inches with the jeans, and Jenny took the waistband and pulled them back up, adjusting them. Then she was able to get the dress down and over my hips and in place.
Jenny put a hand on my butt and zipped up the dress in the back, smoothing the material. Then she crouched down and said "Lift your leg" as she took the jeans off my feet, tossing them aside with my shirt.
"Um, you took off my pants!"
"Well, yeah! You're welcome. You couldn't wear the dress over your pants. It looks nice on you. Go look at yourself in the hall mirror."
I turned for the door to the hall when I heard, "Wait. You should have the whole outfit first."
Jenny came up to me, holding a pair of full size pink panties. I noticed the shiny material, and the lace waistband. "I'm not going to wear those."
"It goes with the outfit. Come on! You need to wear these too." Before I could react, Jenny crouched in front of me again, and slid her hands up the dress to take hold of the sides of my briefs, and pulled them down to the floor. I was shocked, but I lifted each foot so she could take them off. Jenny held my briefs up and said, "How cute! I love these underpants!" and tossed them over by my jeans and shirt.
Then Jenny held up the pink panties and motioned for me to step into them. I seemed hypnotized by her commands and manner with me, and I followed her words as I stepped into the panties. She pulled them up under my dress, then carefully pulled them out and around my cock and up to my waist, taking extra care to not touch my cock.
"You might have to adjust them a bit. It seems that your penis is getting larger. Do you like being dressed up like this?"
I had another flashback to a time when we were kids. We were at Jenny's house, playing in her room and the rest of the family was outside in the yard. Jenny wanted to show me the new panties she was wearing, in exchange for me showing her my briefs. She made me take down my shorts first, and then dropped her shorts as well. As we stood there in our underwear, Aunt Peg came in and caught us. I had forgotten all about that. We thought we were going to get in trouble, but Aunt Peg was very calm and asked what we were doing. I told her Jenny wanted to show me her new panties, and Aunt Peg asked if I wanted to see them up close. I did, so she got a new pair out of Jenny's dresser, and gave them to me to put on over my briefs. She said other boys would tease me if they saw me wearing panties, but I could whenever I was at Aunt Peg's house. I hadn't thought about that in years.
"I said, do you like being dressed up like this? Your penis seems to like it."
I looked down and saw a tent forming in the front of the dress. Hearing Jenny say "penis" was also arousing, but she was my cousin and this seemed dirty.
"Um, yeah, it's fun, but I think I want to put my own clothes back on."
"Just go out in the hall and check yourself out in the mirror."
I turned and went out to the hall, and saw myself in the full-length mirror. It was actually nice seeing myself in the dress. The tent in the front distracted from the look, and I tried to adjust my cock in the panties to not be so noticeable.
I went back to the sewing room and looked for my clothes, but they were not there. "Where's my clothes?"
"I just put them aside to give us more room. You'll get them back when we're done."
"Done? I want them now!"
"Don't use that tone with me. You do what I say, or I keep your clothes, and you can explain to my mom when she gets back, why you're wearing women's clothes and underwear."
I was caught off guard, and clearly Jenny was taking control of our situation. In a way I liked being told what to do, but it was also a little humiliating.
"So, are you going to do what I say? I have some more outfits for you to try on."
I hesitated. "Sure"
"What did you say? Did you mean 'yes'?"
"Yes! I'll go along."
"Yes, what?"
"Yes, ma'am."
"Ok, that's better. Now let's take that dress off and try the next outfit. Jenny came behind me and unzipped the dress, then helped raise it over my head and off. Now I was standing there in just the pointy white bra and pink panties. My cock started tenting the panties again.
"How cute! Your little penis really likes this. Let's try on this outfit next."
Jenny brought over a white full slip and helped get it over my head and smoothed down my body. I ran my hands over the silky slip and enjoyed the slippery feel. I felt very sexy, even though I was wearing women's clothes. I was so confused.
Digging around in the closet area, she brought over a silky cream-colored blouse, and helped put it on me. Jenny buttoned up the blouse, a surprisingly intimate act. She held up a woolen skirt and helped me step into it, sliding it up against the slip and zippering up the back opening.
"You look great in that too. Check it out in the mirror."
I obeyed, and walked into the hall to look at myself in the mirror. It was so strange, seeing myself again looking like a woman, well, except for the hair and no makeup, but even then I could imagine a feminine side of myself.
Like in a trance, I walked back into the sewing room, and Jenny was waiting for me with a new dress, a knit short-sleeve dress in dark blue with small black flowers. "Look at what else I found for you!" she exclaimed. "Let's try it on you."
I followed Jenny's lead as she unzipped the skirt and helped me step out of it. Then she came up close to me and unbuttoned the silky blouse. I felt her warm breath on my neck and must have shivered a bit, as Jenny looked into my eyes and smiled. She leaned in and kissed me on the cheek. "You're being such a good boy! Are you having fun?"
I hesitated and stammered, "Uh...I guess so...yeah, I am."
Jenny grinned. "Good! This is really fun for me, and I like being so close with you. Now, lift your arms."
