It excited me to be wearing boxer shorts.Over the next month I bought a few pairs.Then Trudy started wearing boxer shorts and a teeshirt as pyjamas. ...osuddenly it felt like I had permission to be a boy underneath my normalfeminine attire.But it would be another year before I plucked up the nerve to buy a pairof trousers and, although I told myself they almost looked like boy'strousers, the truth was that the zip ran down the side rather than downthe middle. In short they were obviously Ladies. After a while, Sydnee pulls off my boxers and straddles my hard dick and smiles. “You’re going to cum first.” I laugh. “Sit down. Let’s find out!” Sydnee smiles and slowly lower herself onto my throbbing hard on. She takes my swollen pole into her tight, wet pussy moaning as she sits. “Shit! You just keep getting bigger every time.” I grab her waist as I go deeper into Sydnee’s wet hot box. I tilt my head back moaning loudly as I finally feel every inch being inside of her. She leans. The tight fit seemed almost comforting as Ipulled it past my hips, shimmying a bit for the thong to find its placebetween the cheeks of my ass. The odd lingerie was strangelycomfortable.Next I put on the heels. I could never wear those I thought to myself.There must have been something better in the closet. The discovery mademe cringe at what I saw. The only clothes in the closet where things Ihad purchased for Katrina or had encouraged her to buy. Needless to say,none of clothing was. About 6 weeks after I started working there, four seniors from the local high school were hired for the summer to man the fry station, cook burgers, and work the counter. One, in particular, caught my eye. His name was Matt – he was a senior who played tight end for the local high school football team. He was a good looking guy, with a nice build and big muscles, but he was also a bit shy, which made me think he didn’t have a lot of experience with girls. This kind of intrigued me, and I found.
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