The Lost Soul

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I said to Jane, "If this is what you want, we can start straight away, I will pay for everything, and you are under no obligation to me."

Jane nodded.

I turned to Debbie and said, "Go for it."

Debbie smiled and raised her glass, "Too Jane."

We clinked glasses, "To Jane."

I did not see much of the girls over the next couple of days, only at meal times. Jane was acting more feminine with each passing day, and she started to show a new found confidence.

The lack of contact had helped me out, as I was truly turned on by the young princess now living in my home. I had to keep reminding myself that it was a young man underneath the sexy exterior. I rationalised my desire to the fact that I had not had any female companionship since Karen left.

The day of my dinner party had arrived. I was busying myself with work, whilst Jane co-ordinated with the caterers, prepare the dining area, all under the watchful eye of her madam.

An hour before my guests were due to arrive, and I had just finished tying my tie, when there was a knock at my door.

"Come in," I announced.

The door opened, and my jaw dropped and my cock stiffened.

Jane was dressed for her duties this evening, and part of me knew Debbie had a hand in the choosing of this outfit, knowing my desire for a girl in a tie.

Jane was wearing a white shirt, buttoned to the collar. A perfectly knotted silver tie, with thin black stripes sat around her neck. She wore a black waistcoat the did nothing to hide her female figure. Below she had on a tight pinstriped pencil skirt, that rested just above her knees. On her smooth legs she wore nearly black stockings, and 3-inch black court heels on her feet. Her long brunette hair styled in to tight bun, that any stewardess would be proud of.

Jane gave me a little twirl, "Will I do sir?"

"Oh yes," I replied, will a little too much desire than I wanted.

Debbie entered the room, she was dressed casually and said, "Right, I'm off out for the evening, she is ready."

Jane looked proud at Debbie's assessment, as she gave a little bow before returning to her duties.

"Are you going out of your way to make her desirable to me?" I quizzed Debbie.

She winked at me, "Is it working?"

"I wish it wasn't," I replied, "I'm too old for her."

"Bullshit!" Debbie exclimated, "There is barely 9 years between you."

"But," I started to say.

"No buts," Debbie cut me over with her harsh Scottish tone, "She wants you, can you not see that, the way she goes all out to please you."

"No?" I protested.

Debbie shook her head at me, "How the hell did you ever find a wife, you are crap at reading signals!"

She turned an left the room, still shaking her head in disbelief at my ignorance.

The dinner party was a resounded success, and Jane ran the event like a pro. After my conversation with Debbie earlier, I was now hyper aware of how attentive Jane was acting towards me.

I knew I was attracted to her, and the fucking tie kept my cock uncomfortably hard most of the evening. But could I love her, she was not a real girl.

After the last guest left, I retreated to my office, leaving Jane to clear up and dismiss the catering staff.

I booted up my PC and accessed my private folder containing Karen's uniform greatest hits.

I picked one of her in an army uniform, the tight collar of her brown shirt, the perfectly knotted tie, over which she wore the brown tunic and skirt, topped off with the officer's peak cap on her head.

I pulled out my cock and started to jack off to the video, I did not notice Jane walking in the door was behind me, as I had neglected to close it.

I started to whimper with pleasure, and without thinking the word, "Jane", escaped my lips.

Jane to the bold step to walk into my line of sight. I jumped as I noticed her, desperate to cover myself up.

She smiled at me, "Allow me Sir."

She pulled my hands from my crotch, I could have fought her off, but I was too stunned to act.

She parted my legs and knelt between them.

She looked up at me and smiled reassuringly, "It is OK, I want this too."

With that, she lowed her mouth on to my cock, I closed my eyes as the feeling overwhelmed me.

I looked down at the sexy sight of the young brunette, prim and proper in her shirt and tie, blowing me. I felt my cock stiffen even more.

The video of my ex-wife, completely forgotten about as Jane went to town on my cock. She alternated between sucking my dick and licking my balls.

I was amazed at how well she was doing; she was blowing me like a pro.

I shuddered, as my cock erupted between her moist plump lips.

"OH GOD!" I screamed has I unloaded into my young housekeeper's mouth,

Jane did not slow down, and gulped down every drop of my seed. When I was spent, Jane let my cock out of her mouth, licking my piss slit clean.

She stood back up and straightened her skirt back down.

"Will there be anything else Sir?" She said, as if she hadn't just swallowed my cum.

"Erm, no Jane thank you, that will be all," Is all I managed to say.

Jane nodded, turned on her heels and left.

I instantly felt guilty, "What had I done!"

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arrow013arrow01317 days ago

excellent story line. The ending lends to a little suspense and hope there will be another chapter.

ColonelinguistColonelinguist3 months ago

The submissions of the first two anonymous commenters below couldn’t have explained it any better.

Like most men; gay, bi or straight, we all enjoy Vicariously fantasizing about being one of the fictional characters in all of these various sissy - dom story situations; top or bottom - which ever one floats your boat. But when the crossdresser in a story decides to mutilate his body with HRT and bottom surgery, my interest in that piece just automatically disappears.

Long ago, there was a period when I publicly hit the clubs in drag. Being a hot young chick with a dick was always loads of fun, but all the preparations that it took, trying to just look passable took hours at first.

Why a guy would want to do that every day is hard for me to even imagine. I like pretending to be a girl when the mood hits me a when I’m at home but I’ve never want to become one full time.

BigT280BigT280over 1 year ago

I really enjoyed the story and I hope you will continue writing more parts .

bluemoves01bluemoves01almost 2 years ago

Thank you. Looking forward to the next part.

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