A Sissy's Journey Ch. 03

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"Jesse baby, stop for a sec and look at me," Amanda wanted more...no, she needed more!

"You're beautiful with a cock Amanda," Jesse blurted out.

"Thank you sweetie, but I have another favor to ask. This cock is designed for fucking, not sucking. I've used it on other girls and the part up in me gives me the experience of having a real cock. I really need to fuck you right now, do you think you can take it?"

He hadn't told her about his own collection of toys. And he hadn't told her what he did with them. But the desire to feel her inside him was overwhelming and he could only answer with a simple, "I want it too."

Staring at one another, everything before this moment seemed to recede. All that had been games and explorations and more like getting to know each other compared to this. The unspoken truth was that this moment would change things for ever. He had been unable to fuck her only a few days ago, but now she would mount him!

Finally, in a voice tinged with humiliation but pushed by desire, Jesse surrendered, "I have used dildos for awhile now. I know how it feels. And I want it if you do." Amanda liked those words. She also liked that he didn't even try to hide his cock that was now standing up straight again like a little toy soldier standing guard.

Amanda felt a little light headed. This had all unfolded so quickly and unexpectedly. She usually was the calm one who directed the show, but now a new lust filled her. She let the images of fucking a man roll around in her mind, and the new discovery was one she had never even known to search for. But now, her lust for mounting a man had been ignited and there was no quenching this flame.

"Okay, let's get these panties out of the way," she said while ripping away the silky fabric now bunched around his ankles. "Now, just one more thing," she mumbled as she walked to the night table again. Jesse loved the way she was so confident with her nudity, her breasts and the fake cock gently moving with her steps.

He already knew what she would bring out of the toy drawer this time.

"Roll over on your tummy sweetie," she said, giving his cock a playful tug.

"Don't just lay there on your stomach and play dumb, stick your butt up here," she ordered with a smack on the ass to make the point.

"Jesse, you have to spread it open," she said once he had is ass in the air and his face on the pillow. "I'm not your servant, you know. If you want your butthole lubed up before I fuck you, then you better behave!"

It embarrassed him to pull his butt cheeks apart, but he couldn't find any strength to resist. The shame of being so exposed seemed to get all mixed in with his hard cock and he felt his thoughts shrink down to only this moment. Whatever he was experiencing, it melted away any manly pride that might have stopped him from obeying her.

The cool gel was a shock. But soon the shock was replaced by pleasure as she lovingly massaged around his puckered hole. "Open wide," she said just before slipping one slick finger inside. Around and around she swirled her finger, slowly stretching him wider. Then two fingers...and finally three. He was ready as he would ever be, and she sensed it was time.

"I want you on your back for your first time. I want you to see me when I fuck you. I want you to look into my eyes when I open you and make you mine." Oh yes, this was indeed a new Amanda he had never known, and oddly he felt very safe and small.

"Yes, please show me how," he said meekly rolling onto his back, his legs spread without conscious thought.

Amanda knelt between those open legs, and lifting them just under the knees pushed him up and open in the same move. She had fucked more than one girl like this, but Jesse would be her first man and she needed his legs a little higher so his butt hole lined up. With his knees braced wide on her shoulders, Amanda slowly and expertly worked the full size cock into her friend. She loved the thought of his surrender and let him know it with one hand pressing her weight down into his chest and the other guiding her cock into his body. "After today, you will have a pussy. I hope you know that," she whispered as the hard girth filled him for the first time.

Jesse was too entranced to reply, even though he heard and mentally told her he wanted a pussy. And with each thrust, each one going deeper, and each one coming faster and faster, both of them were thinking the same thing; "This is wonderful!" But it was only Jesse that said it out loud as he tensed and splashed another orgasm onto his smooth flat belly.

Seeing him loosing all control so quickly was all it took, as she tried in vain to postpone her own building explosion. The waves soon overwhelmed her and Amanda too experienced a release like no other before it. The confused reversal of roles left her feeling more emotionally and physically satisfied than ever before in her life. In that moment, she knew that fucking men was going to play a big part in her future.

Collapsed in a heap, no sound but hard breathing, the two lovers tried to collect the scattered fragments of their minds. Without any real reference to time, the two slowly regained some sanity. Still on top of him, Amanda pushed herself up enough to look into Jesse's eyes. No words were spoken, but at the same moment theirs eyes slowly closed and their lips met in a silent conversation.

Laying in a cozy cuddle, after the passion had dissolved into quiet bliss, the two talked quietly of feelings and emotions. It was so very easy to be open and sincere, as if they had been doing these wild things together forever. The things Jesse was saying reassured her that she had done the right thing in forcing him to get real about himself. What went unsaid, but was obvious, is that both knew this was just a beginning. What might lie ahead was a mystery, but it would never be the same as what was behind for either of them.

*****

To be continued...

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diane92374diane92374over 2 years ago

Absolutely love this story so far. I found myself wanting to be Jesse wearing pink lace panties and nighty in bed with a beautiful woman encouraging me.

GrrrreatImaginationGrrrreatImaginationalmost 3 years ago

Nicely done. Boundaries expanded and friendships maintained. Now, how conventional and how kinky will their courses wander? On to the next chapter.

And thank you verrrry much.

roveroneroveronealmost 4 years ago

I think very first Lit story that mentions/uses a Feeldoe....

I like Amanda.

npanxxnpanxxover 5 years ago
Nicely done

I enjoyed the awakening that both parties experienced here.

I fantasize about being feminized and sissified; being taken by a dominant woman.

Hopefully this series goes where my own fantasies want it to go.

JSF79JSF79about 6 years ago
Brilliant!

It's as if you reached into my mind and took out my thoughts. Sometimes when I read your work I find myself wondering if I wrote it. That's not conceit, it's just your thoughts and us of words so closely match my own. You are a truly talented writer that creates believable and loveable characters that then go on and do very sexy things. Great work!

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