My Initiation

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cdandy
cdandy
197 Followers

"Fuck me now" I said sexily and she got up and lay between my legs. I guided her in to me then put my arms round her as she pushed her cock in and out of my ass. She fucked me. I felt no sexual gratification other than I knew I was pleasing her but it did feel nice. She pumped harder and harder, her large cock sliding in and out while I stroked her hair, neck and body. Finally with a cry she climaxed into my ass. Jerking and lowing down, she lay across me panting and opened her eyes. I took her head in my hands and kissed her deeply. I could feel her softening inside me and pushed her bum towards me trying to stop the inevitable. She slipped out and I lowered my legs into a more comfortable position.

"Oh that was terrific. "she gasped. "Did I hurt you?"

"Only at first " I said, kissing her and grasping her round the neck. "It felt amazing. You can do that again any time you want."

"She laughed. "Oh I'd like to. But you're going to do me as well you know."

"Shower first" I said with a grin. We dashed off for the shower and both stood under the jets kissing. She took the gel and began to soap me all over. And she didn't miss a thing. Starting with my back, massaging my shoulders and working down to my buttocks. Her fingers caressed my anus, even slipping a finger inside as she kissed my neck. I was starting to get hard again. Her hands reached between my legs and gently rubbed my balls between her fingers.

"Turn round" she murmured. " and began to wash my chest, working down to my stomach and finally my erect cock.

"My turn to wash you. " I said after a few moments of her masturbating me. I didn't want to cum just yet. I took the gel and started on her chest then, turning off the water, began to soap her all over. I paid special attention to her cock and balls, keeping up the strokes till I felt it harden. Then I turned her round and started on her back. Working my way down I slid a soaped finger into her ass and started to widen her hole pushing her forward. She gasped as I inserted two fingers but not in pain but in pleasure. As soon as I thought she was wide enough for me to start, I soaped my cock and placed it at the entrance. Very slowly, I pushed backward and forward as she was able to take me inside her. My cock is a smaller than hers and after a few pushes slid inside. I kept very still for a minute until I felt her push back towards me. I new she was ready now and began to push slowly in and out. She was moaning with pleasure. I reached a hand round and started to masturbate her in time with my motions. It felt wonderful. Her ass was so tight and hot, her muscles tightening and contracting adding to the feeling. I lost myself in my ecstasy and went faster and faster. I exploded inside her with a gasp.

My passion spent, I put both my arms round her and held her, kissing her neck until I slipped out of her.

"That was wonderful" I said. She turned round and hugged me.

"That was a fantastic feeling. It didn't hurt at all".

"Probably cos I've not much to boast about" I said laughing.

"Well I think it's the best cock in the world she said taking it in her hand."

We showered off and dressed in our baby doll nightdresses and went to bed. I hadn't realised we'd been at it for three hours. It was late and there was work tomorrow I thought with dismay. Back to the suit and tie.

Chapter 9

Michelle came home from the office next morning looking worried. "I think the cat's out of the bag" he said "I've just overheard someone saying we were living together and were gay."

"Cant be much of a rumour" I said "For once they got it right"

"I'm not sure I can stand being the subject of their gossip." She said. "It's only a matter of time before they find out everything. They wont leave it alone you know."

I nodded. "Come on into the lounge Michelle, I've had a bit of a plan going round in my head these past few weeks. I haven't mentioned it to you because I wanted to get the details sorted in my head." She sat down beside me and I put an arm around her. Her head tilted to one side looking at me closely.

"I've sold my house now and there's a lot of money waiting to be put to good use." I took a deep breath. "I'm sick of changing into a man each Monday morning, then coming back to living the life I really want. It's time for a change. My plan is, if you're agreeable, to start our own accountancy business with the money. We're both fully qualified. We split everything down the middle, both of us equal partners. I live with you, so we really share that side of things. We can probably steal a few clients to get us started and when we get busy, hire a few others to work for us. The thing is, we become women accountants. No more male clothing. We start off as women and work as women. Now here's the catch. Will you marry me?"

She took a deep breath and flung herself on top of me in joyful tears. "Of course I will. Yes. Yes." She cried. "And your plan. It's wonderful." She sat back after a few moments looking at me with an awed expression. "You'd do all that for me?"

"For both of us Michelle. I want to be a woman just as much as you. We share a house and now we can share a business. Unfortunately the marriage wont be legal but In our eyes it will be."

"In my eyes, you'll always be my partner." She said quietly. "I suppose we become lesbians."

"Lesbians are more accepted that transvestites," I said. "Yes, we'll promote ourselves as lesbians."

So we followed the plan. We became quite successful and threw away all our male clothing.

The plan for next year is to complete the transformation medically. But that's for next year.

The End

cdandy
cdandy
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ColonelinguistColonelinguist6 months ago

My crossdressin’ days are over so I love indulging in these kinds of fantasies, plus they tap into some memories I have of being feminized and ultimately fucked.

Unfortunately, my own Michelle was nowhere near as hot as the one in your fantasy so thanks for this re-boot!

AnonymousAnonymous10 months ago

As a lifelong CD I love it.

AnonymousAnonymousabout 1 year ago

Such a beautiful romance.

nelg12nelg12over 1 year ago

Great story I would have like to Steve to have got a female name. This is the third time I have read it and will probably read it again

CybrOtakuCybrOtakuover 1 year ago

A wonderful story! To think it's been over 16 yrs now since this was written... the word "transgender" was not in use by any girl I knew back then, and legal marriage was seen as a damn near impossible dream. It's good to know we have made so much progress as a community, and would love other girls to see from these 2 stories how, and why, crossdressers are our sisters too. As a Trans Female it's Soo awesome to read happy ending stories that have withstood the test of time. Especially both of these that have a T4T flair you almost never see in erotic literature. Amazing work both then and still in 2022!

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