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”Gingerly, Sandy boarded the boat. She was slightly wary of Caleb, and the way he looked at her left her in no doubt that she might have to deal with advances from him. Sandy liked bigger and older men, but Caleb was just a little larger and scruffier that she would normally tolerate. Sandy, however, liked having a bit of fun and was not stuck-up in any way. She also enjoyed being a cock-tease and figured that the excursion might be an interesting titillation, for them both.As she observed the two loungers at the front of the boat as they got underway, Sandy bemoaned the fact that she had not brought a bathing suit along.“Are you wearing a bra and panties?” Caleb asked.“Sure, why do ask?” she answered, with a look of surprise.“Well, all the homes along the river are well recessed from the river bank, and so, anyone watching the boat will simply think that you are wearing a bathing suit.” Then, after removing the shirt he was wearing, he continued, “I’ll also go topless if it makes you. “Maybe you should start. If you’re going to do this, you better go all out. Once you can pass, you could get the opportunity. Take advantage of it. Maybe I can find someone who would be happy to give you the practice. Trust me, it’ll be fun!”Jan’s comment stuck in my head for days afterward. The idea began to appeal to me.The next few months found me dressed as a female most of the time. Mom and Jan gave me pointers to improve my appearance. I wore guys' clothes only when the circumstances required it. With some practice, my voice was able to emulate that of a real female.Many women say they can’t wait to come home and take off their bras. But when I had to wear guys’ clothes, I couldn’t wait to return home and put on a bra. Now, my mom and sister were happy to let me do that.After a while, Mom felt I was ready for the new me to go public. Jan and I went out to the store one day. No one seemed to notice anything different about me.Then Jan suggested something more. She said she’d fix.
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