The Path to Happiness

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He shut the butt plug of and ordered me to stand and bend over the desk again. I was worried he was going to cane me once more. He pulled the plug from my arse and replaced it with his cock. I was well lubed and stretched and he started to bugger me. As he thrust into me, he called me a dirty little cock whore. Though he did not have the biggest cock I'd seen, it sure beat the cucumber.

He started to fuck me with some force and I was actually loving the submissive role. If this was what getting fucked felt like I would defiantly be adding it to my price list. I was fully immersed in my role as a sissy girl slut and called for him to fuck me hard. He slapped my arse cheeks, this brought back the pain, but he did increase his pace. My own cock had again swelled to full hardness, and I thought it would explode it was so hard.

With a large cry he emptied his balls into my bowls, this sent me over the edge and I came too. With a couple of last thrusts, he collapsed on top of me. He whispered in my ear that I was worth every penny. His cock softened and slipped out of my cock and he gotten of me, and released my ankles from the spreader bar.

His demeanor changed in an instant as he held out his hand and introduced himself as Chris, I shook his hand.

I looked a right state after the royal fucking I just got and Chris offered me the use of his bathroom. As we entered the living room Chris handed me a couple of boxes and asked me to wear the contents. I stripped off my school clothes and examined the packages. There was some sexy underwear, a gaff with a fake vagina molded into the front of it, a set of real looking breast forms, and wig that was clearly more expensive than my fancy dress shop wig and a crimson dress complete with matching shoes.

I showered and redid my make-up, this time to reflect my elegant outfit. The gaff was uncomfortable at first as it bent my cock and balls away, but when I slipped on the red lacy panties there was no bulge to be seen. The breast forms took a little time to figure out, but once I had them stuck in place and slipped the matching red bra on there was no trace of my male body. The wig had instructions, it was a lace front wig and I had to glue it into place. Like the other items it blended perfectly.

I slipped into the gown and shoes and checked myself out in the mirror. I had only just met Brenda but I like what I saw, I would defiantly be exploring this side of my new personality in the future.

As I left the bathroom Chris was waiting for me, he too had changed into a 3-piece suit. His tie and handkerchief match my dress. He then laid a diamond neckless around my neck and clipped on matching ear rings. I heard how girls swooned when a man treated them right, and I knew I liked it.

Chris picked up his car keys and lead me out the door with my arm in his. He was taking me out for dinner.

I felt like Julia Roberts from Pretty Woman.

Comment if you would like the next chapter.

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AnonymousAnonymousover 1 year ago

Nice story so far.

AnonymousAnonymousalmost 2 years ago

Nice story, I enjoyed.

As far as the writing goes...a lot of spelling errors. A good editor would go a long way in helping to polish it.

AnonymousAnonymousalmost 2 years ago

Intriguing story in the beginning jot sure which way it was going to go!

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