Wednesday, September 17, 2014

So, where were we? Oh yes, she embraced me, told me hot this was, whispered in my ear she loved me. I moved my arms up to hug her back, felt the thin fabric of her dress, knew how he felt. "We're good," she asked softly.

"Yes," I half moaned. 

"Tonight, I'm his whore," she said, moved her mouth to mine, kissed me as deeply as she kissed him.

Matthew cleared his throat after a few moments. "Bring your wife to me, John," he said.


How does one pass the time? Thinking about it? Trying not to? At first I didn't want to think about it, but that's all I could do; after some time, it faded and I read, watched tv, not really into it. I carried my phone with me everywhere, waiting for a text, but for the first half hour, nothing. Then a short text from Emily. "Top drawer of the desk in the study."

"What," I responded. "You having fun. Everything good?"

She didn't respond.


"Top drawer of the desk in the study!"

I quickly went to the study, opened the top drawer to the walnut desk; there was an envelope with her handwriting, "Sara."

I opened it, a card, on the front, simple printing: You're the best thing in the world.

Inside, her handwriting:


Today I'm getting two of the best things in the world: a strong, masculine man and my soft, feminine sissy. And I'm getting them only because of you.

I can't wait to be alone with Matthew, I can't wait to lick him, taste him, and feel him inside me. I want it, I need it, you understand, I know. A man, Sara, I need a man. Sometimes a girl needs a man. And I do.

But that's not enough, that's not all I want, there's so much more. It's not just a man, it's you, too. I need my sweet sissy, I need her more than I need a man, for without her, without you, a man means nothing. You. You come first. You. Always.

So as much as I want Matthew tonight, as much as I look forward to our date, as much as I yearn to feel him inside me, to fill me (really feel him inside me, really fill me), even more I yearn to come home and share it all with you!

I know it's not fair, I get what I want all night while you have to wait till later, but I'll make it worth the wait, I promise. I promise.

I know waiting's hard-no pun intended-but I hope waiting is part of what makes it exciting for you.

Love always and forever,


P.S. I don't know what time I'll be home, so you don't have to wait up, but wear something pretty to bed because I'm definitely waking you up when I get back!

Waiting was hard, since all I could do was think about it, wait, wait.

I wasn't awake when she got home, but not asleep, either. I was in bed, candles lit, wearing something pretty, dozing. I heard the alarm chime when the door opened, waited still, waited.

She came into the room, slowly, quietly. "Sara," she whispered.

I sat up, looked at her. Her hair and makeup were disheveled, her hose gone. "Em," I whispered back.

She walked up to the bed, saying my name, Sara, Sara, Sara, as she reached around her back, undid, took off her dress and dropped it to the ground, standing there only in her black panties, heels.

"Em," I said again, staring at her panties.

"I want to share with you," she said, "I need's important."

"Em," I said again, "did...did he..."

She nodded. "Twice."

"Did he...did you...use..."

"No," she shook her head. "No." She moved to the bed, next to me, touched my face, kissed me. "He started here," she said between kisses. "And it was...powerful."


"Powerful," she kissed. "Different," she kissed. "You beg and I almost always say no. He didn't ask, he didn't beg, he word...kneel."

"You knelt."

"I knelt, of course I knelt. I felt him grown in my mouth, I felt him take charge, I felt myself surrender, I was so wet, so wet. I always good it feels to do a man."

He was inside her, his cock, in her mouth, the mouth kissing me. "Did he..."

"No...I wanted to...but no...another time, he said."

"Fuck, Em."

"He did, I told you, he did. The first time was good...the second time...I got dizzy...I got confused. He was on top of me...I was on my stomach...he was on top of me, holding me down...fucking deep..."


"I'm sore," she said softly.

"Did he hurt you?"

"No...yes...I'm just sore."


"What do you want, Sara?"


"What do you want?"

" know," I mumbled.

"Share, I want to share..."

I don't know what was left, the mesh front of her panties were damp and crusty at the same time, from him, from her. The smell was...powerful...musk...masculine...but she was there, too, soft, feminine.

I licked her body, licked her breasts, licked her stomach, lower, flicked my tongue once, twice, three times against her panties. "I want to share," she said again.

"I know," I said.

"It's important."

"I know," I told her, "I know."

I licked, panties first, her swollen lips second, inside her last. I licked...everything that was there, shared, participated. I tasted her, tasted him. Feminine, masculine, both. Emily. Matthew.

I licked, tasted, tender, gently; she orgasmed again, then again, then again.

"I want to unlock you," she said at one point, "I want to see...if you're excited."

"I am," I promised.

"I want to see," she said. "It's important."

I was. How could I be otherwise.

Free, I didn't last a minute, gentle as she was, it had been too long, was too much.

"Shhhh, that's it," she said lovingly when I shook, "that's it, that's it."

We fell asleep like that, her taste and his on my mouth. My mess on the sheets. Proper places. A man cums inside a woman, a sissy does not. Proper places.

The text came sometime after we fell asleep, to both our phones. "Sweet dreams to both of you."


We've had several interactions since.

She went to dinner with him the following week, no sex, though, no time that night. I think Emily and I were both disappointed.

I met with him for lunch last week, we talked about Emily. Me. How important she was. How important I was to her. He reassured me then, before, and after, he knew that, respected that.

I was afraid to ask about Sara...I wanted to...was afraid.

But Emily isn't...she wants him to meet me...the real me...knows it's important to me. "He will," she said, "trust me."


  1. Wow, thank you so much for the update. Cant wait for more details. More meetings! And progress in all the different relationships1

  2. Thanks for the update, Sara. Mathew seems like one in a million - he 'gets it'. And he's so manly and so very thoughtful- "Sweet dreams to both of you.". I'd be thinking of inviting him for a home cooked meal. It would be so great serving Mathew and Emily in a very full pinafore apron. But before that, maybe a little shopping trip is in order - something 'hot' for Emily - something white and virginal for you - and a very masculine set of PJ's for Mathew. Thanks again!

  3. A most cherished update. What a coming home moment! I hope it was all you were envisioning and salivating over :)
    Can't wait until you experience your first time actually seeing Emily give herself to him. For many, that is the ultimate cuckold moment. Of course, for you, I think there are other individual events that may be seminal, and most are connected to Matthews cock ...

    Thanks for the update Sara, and your beautiful writing.


  4. So powerful Sara - thanks for sharing.
    Huge respect for Emily for way she has reassured you of her love and commitment to you.

    Love Tanya xxxxx

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  6. Oh, Sara...

    Thank you so much for the update. It's lovely, absolutely lovely. Emily is lucky to have you, too.

    I loved reading your update, absolutely loved it. And yet...

    In contrast to some of the other commenters, I am not as optimistic as some of them are. I see Matthew as someone who is commitment-phobic, which is why he wants to have sex with a married woman. He sees her as not looking for a relationship with him. And she's not, which is why everything seems lovely right now.

    But he clearly has an issue with transgender issues. He's made it very clear that he not only isn't ready to meet you as Sara, but he does not want to meet you as Sara AT ALL. Emily has committed herself to making that happen. Matthew is going to go along with it, because she'll make it clear to him that he has to if he wants to keep fucking her. But he'll hate it. He'll hate the idea of being in the same room with you while you're dressed as Sara. Even though he will express genuine surprise for how good you look. And the thought that you might want to please him sexually will turn his stomach. Which is absolutely tragic.

    They will both want to keep seeing each other. But eventually Em's commitment to you, and her need for you in her life as Sara will win out, I have no doubt about that. But I fear that there will be some serious bumps along the way.

    It's great that he seems to want to bond with you as two guys. But you and I both know that's a fantasy. It's not who you really are. It won't work for you, and after he meets you as Sara, it probably won't work for him as much as he would like it to right now.

    I hope that I am wrong, because I truly want the best for you, and also for Emily of course, too.

    xoxoxo xoxoxo

  7. Congrats to all three of you for finding a way forward that gives you each an adventure on terms you wanted. I don't agree with Christine B, and I am sure that with Emily's clever management of the situation, you can all have a wonderful time together. But that's for the future ... enjoy the now ... and thanks as ever for sharing your journey ;-)

    sara e

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