Tommy's Wonderful Holidays


When I was a kid, I had two female cousins who were my age, and I regularly celebrated major holidays (e.g., Christmas and Easter), as well as birthdays with them.  I like them both and they were always nice to me.  My parents were immigrants, and we lived in a small apartment, so we were always the visitors.  One of the girls lived fairly close to me, but the other lived in a neighboring state.  A few times a year, I actually stayed at the house of the one who lived out of state.  She had a younger sister, but no brother.  Anyway, the family get-togethers, where presents were exchanged, always involved the girls getting pretty clothing, dresses, skirts, petticoats, “day of the week” nylon panties, etc.  There would be “oohs and aahs” at all the pretty stuff and they would hold them up and show them to everybody, often passing them around.  I was the only boy there and would get slightly embarrassed when, for example, I was handed a box of nylon panties or a slip, but I did like the feel of those clothes and was slightly jealous that I never got anything as nice.  Anyway, one year, when I was about twelve, we went out of state to my cousin’s for Christmas, and I stayed over for a few days. 

As usual, this cousin and her sister got pretty dresses, skirts, slips, petticoats and panties for Christmas, which I got to see and touch on the day.  A day or so later, I was in the living room and saw one of the petticoats sort of standing up in front of the tree.  I walked over to it and felt the silky top.  I hadn’t noticed, but my aunt had come in behind me and said, “Pretty, isn’t it?” with a big smile on her face.  I must have blushed, because she said, “Don’t be embarrassed.  I feel sorry for boys who never get anything pretty to wear.”  Now, this aunt was very pretty and was my mother’s sister.  I knew that she really liked me.  My uncle was at work and her two daughters had gone ice skating with friends (I didn’t know how to skate).   She went on, “I have an idea.  Since there’s nobody else here, why don’t you once feel how nice that stuff is to wear?  It will be our little secret.” 

I didn’t know what to say.  Without waiting for a response, she took my hand and led me upstairs to my cousin’s bedroom.  After fumbling around in the closet and the dresser, she assembled a pile of clothes.  “Take off all your clothes and start by putting on these pretty pink nylon panties.  Then, put on this dress,” as she held up a very pretty pink party dress with ruffled sleeves and a full skirt.  “Put it on over your head, but I will have to button it up.  I’ll wait outside until you’ve gotten the dress on.” 

I pretty quickly got out of my clothes, and got the panties and dress on, so I called, “Aunt Helen, I’m ready.” 

She came in with a big grin on her face.  “Wow, you look terrific already.  Now, it’s time for me to put your stockings on.”  As instructed, I sat on the edge of the bed as she pulled the stocking up my leg, way up under my skirt.  It felt great and I started to get hard and I was hoping she wouldn’t notice. 

She handed me two frilly garters, saying, “Here, use these to hold the stockings up.  Normally, my daughters wear a garter belt like this,” holding one up for me to see.  “They fasten it around their waist on top of their panties and they then fasten the stocking to these things,” showing the fasteners.  “It’s a little complicated for you to do it yourself and I don’t want to invade your privacy more than necessary, particularly when you may be reacting to all this pretty feminine stuff.”  I could hardly believe it, but she obviously knew that I was getting aroused and didn’t chastise me.  In fact, with the smile on her face, I think she knew exactly what she was doing. 

She buttoned up the back of my dress and then handed me the most gorgeous petticoat I had ever seen.  “This is chiffon and you’re going to love it.  Just step into it and pull it up under your skirt.  I won’t look.”  She turned her back and I pulled the petticoat into position. 

“Okay,” I said. 

She turned around and broke into the most beautiful smile.  “You look precious,” she said.  “I’ve often watched you as the girls opened their pretty presents and handed them around.  You really seemed to appreciate how lovely those clothes are and I wondered what it would be like to dress you up in them.  You look lovelier than I ever imagined, and you still look like a boy.”  She gave me a big hug and rustled my skirt and petticoat as she adjusted the to her liking.  “Okay, now walk around a bit and feel the chiffon petticoat caress your legs through the nylon stockings.  Then sit down and wriggle a little to feel all the silky layers slide against your panties.”  I did as she said and it was out of this world.  She hugged me again and said, “I can tell by the expression on your face that you’re getting the full experience, and I couldn’t be happier for you.  Now stand up and spin and feel how your skirt and petticoat billow out.”  I did as she said, and it was heavenly as the chiffon petticoats gently resettled around my legs.”  We spent about two hours together, and I think she enjoyed it almost as much as I did.  Finally, she said, “Unfortunately, all good things have to come to an end.  The girls will be home in a few minutes and I think we should keep this our secret.  Just go up and change and leave all the stuff on the bed.  I’ll put it away.” 

I ran up the stairs and changed.  She came in after I had changed and started putting the clothes away, but she stopped and handed me the panties, saying,  “Why don’t you keep this to remember the experience?” 

I put them in my pocket, unable to speak.  When she had finished, I went to her, put my arms around her and hugged her with tears in my eyes, saying,  “Aunt Helen, that’s the nicest present I ever got.”   

“Tommy, I am so happy you enjoyed it.  I enjoyed it.  Unfortunately, many girls don’t know how lucky they are to be able to wear such beautiful clothes.  I could tell by the look on your face at family gatherings that you were taken by the prettiest girls’ stuff.  You’re still a real boy and I love you very much.”

Unfortunately, we never did it again, but I really loved her for it and did many favors for her in later years.


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