Honestly I'm jealous of how good you look in your underwear. Most girls would die to be that thin." I insisted that Catherine looked amazing in her underwear, and she just laughed. I couldn't believe this curvy little angel didn't realize what an image of beauty she was. We were already in her bedroom by the time I realized I had agreed to a makeover. What did that even mean for a boy? Wait, was she going to dress me up as a girl?"Okay" she chimed in "We can use my makeup, and I have a wig from halloween haha. We can borrow one of my sister's training bras, aaaaand probably one of her skirts too. I think my shirts will fit those narrow shoulders of yours." She scurried around her room gathering items while I sat on the bed. My heart was racing a bit. This was a big step up from wearing panties under my boy clothes. And even though I trusted my friend and felt comfortable with her, the thought of being dressed as a girl in front of someone else felt... wrong. But also exciting. I was. . Ashish hugged me and said “Time to give you the surprises that I promised before”They both smiled smirkly and Saurabh went on to get a bag from the cupboard. I didn’t know what was happening around.. To break my surprise ,ashish said “jab maine enter kiya tha maine yeh bag saurabh ko diya tha and it has something for you for your upcoming days and Saurabh also took some photos when you were sucking my dick on the doorstep”Saurabh passed on the bag to me and I opened. To my surprise, it had a butt plug around 4 inches long and wide, a vibrator and some nice and expensive bra and panties. I had no clue what and why this was for. Hence I asked Ashish about the purpose of it and what he said was just blown my mind away.Ashish “ Listen, these are for you. I know you can’t take my dick in your ass because of my girth. So this buttplug will help your asshole to get loosen. From tomorrow onwards you are going to do this for entire day in office or at home –1. If you are at home, your dress.
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