From Bradley to Brendalee43 - Sex Stories

From Bradley to Brendalee43

... any clothing here, with her at size 2, me at 6', and at the time, 230 lbs. But I'd soon get to find out.

Claire had a business trip that would take her away 5 days, including the weekend.

I measured myself and set my own work schedule to accommodate a little shopping and make sure my weekend was empty.

After dropping her off at the airport, I stopped by a couple thrift stores and tried to be quick at what I was shopping for. A couple dresses and how about a night gown with lots of ribbons and lace? I found them. And the night gown was pink. I was excited and nervous at the same time. The shoes that were in my size weren't remarkable so I skipped buying some, that time.

Once home, I put them in the washing machine, and hoped nobody surprised me with a visit as I hung them to dry.

I wasn't going to put them on until after work on Friday but temptation took over.

After dinner, I ironed the dresses and put one on. The look was a fat guy in a dress and panty hose. But the feel was sooo good. Something soft about the fabric. And I got to experience sitting to pee. (that memory would become permanent years later)

The next day, I hurried home, got into my dress, ate dinner then spent time surfing the web about cross-dressing. Which led to many other related things. Petticoat discipline, forced feminization, FLR, and so many more. I was reading more those few days than I had read about my business deals. But it got late, I removed the dress and put on the night ...

... gown. And couldn't sleep. More web time, more thrills and a pesky bulge in the pantyhose. Gotta take care of that, and my hand got a bit of a workout. I took the pantyhose off so I could take my underwear off, then put the pantyhose back on, only to work hard at falling asleep. Not much luck, and I had to service the bulge again. So my weekend would be. It was raining both days, and I was happily in my dresses and hose.

When Monday came, I sadly put the dresses and nightgown in a clothing donation bin and said my good-bye to a fine weekend. But that didn't stop me from finding every web site about those topics every chance I could get. And every time I put my compression pantyhose on, wished they were a little sexier. I found some! These had the compression I needed but also were sheer and very attractive finish, on females anyways. And once again, less expensive to what I was wearing. When I told Claire I would wear them, she said "nobody cares what texture or color they are when they're never seen anyways". She bought it! And I was lucky enough to have a reason to wear them. Wishing a dress could be "prescription", but be careful what you wish for. You might just get it. And I was about to.

It was well into spring, my business required very little attention at the time and I spent much time cleaning up and trimming the yard, the usual things one does to have the yard in shape for the summer to come. And every time I came inside, would browse my favorite sites, longing ...