Halloween was right around the corner but they had no plans and as they sat in the kitchen after school Tammy's mother suggested that perhaps they could dress up as girls!!!
"With your slim builds and long hair I bet you could pull it off....and your sister has bags and bags of clothes she doesn't wear anymore!!! I'm sure we could find a couple of dresses that would fit you!!! With a little makeup I don't think anyone would know who you were!"
The boys caught each others eye when they spent a moment thinking the offer over!
"No....I don't think so Mom, I would feel too weird!"
Later when they were alone and they had found some pretty dresses to wear they giggled about Tammy's Mom's offer!!! Slowly the giggling turned to kissing and then the kissing turned into so much more as hands found their ways into pretty panties....
My first crossdressing experience was during one holloween. My mom and sister thought it would be fun for me to dress up saying "no one would know it was you." They both helped and I was transformed. Neighbors commented to my mom that they would have never thought. My mom and sister drove me to the town's holloween party, in a firehall, leaving me on my own with many people my age. Two boys kept talking to me as they were trying to figure out who I was. Little did I know they had other plans. Taking me out behind the hall to smoke a joint they started to reach under my dress. Feeling submissive as one stood behind me and the other in front. They pushed me down, without much hesitation, and offered me their hard cocks. That was the first time I swallowed cum. My mom and sister asked how was the party as they picked me up. "OK" I said, both smiling as I later found out that some cum had dripped on my dress just under the chin area. They never said a word.
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