And Then It Happened...

In (very) late 2016, "M" found "James" and began an online dialog with him. She told me about him right from the start, and seemed very excited. He seemed a lot different than the first guy she met. Her back-and-forth with James progressed pretty quickly as they got to know one another online. Fortunately we live in the same area, with a metro transit system that ran pretty close to where he lived and where we live.

In our nighttime fantasy building and gurl-girl lovemaking, I began building a picture for M in which she was making love with James. Honestly? She loved it! As did I. Christmas and the new year came, and right after that, M spent a week with her mother a couple of states over. While she was at her mother's, we talked every night as normal when we're apart, and she told me that she had masturbated several times and made herself cum while thinking about "James." As soon as she got back, she agreed to meet him for a date, which she told me about right away.

Talk about excited!

I was just about bursting out of my sissy skin!

I couldn't concentrate. I couldn't stand still or sit still. And all the time, "M" was walking around with this enigmatic smile on her face.

The big day arrived, and (of course), I helped her prepare - dressed as I was in my sissiest things. I remember the beautiful, lacy bra and panty set she wore that evening - something I had never seen before. She tried to temper my imagination by saying "We're just going to a restaurant... And we'll see if we like each other... And we'll see if anything develops from there."

I dropped her off at the metro train station early in the evening with a kiss and watched as she disappeared to catch her train before driving home.

Knowing that she would be on the train for about 45 minutes to get to his place, and then the same to get home, I waited at home and tried to settle myself.

I read.

I watched some TV.

I read some more.

My clitty was locked up as always, and I was wearing my sissiest white lingerie, thinking it appropriate to the event. While the lingerie is a bit different, the color is right, and here is exactly how I was feeling...

And also while I waited - knowing that she might check her mail on the train when she was coming home - I wrote her an eMail and attached a bunch of pictures to (hopefully) convey to her what I hoped she was doing and what she might say to me on her return...

Jan 14

I can hardly wait to pick you up in a few hours...
I hope you are able to look at these pictures on your way home...

I love you,

Sissy L

Here are some of the pictures I sent her with that eMail...

It was several hours later that I got a text message from her telling me that she was on the train and on her way home. Nothing more than that... I left soon thereafter to pick her up, and I was on pins and needles the whole time.

It didn't exactly work out the way the pictures suggested, but instead of me telling you what happened, I'll let my wife's words speak for themselves - extracted from the eMail exchange she had with James the following day when she got home from work (the names and a couple bits of information - shown in < > have been changed to "protect the innocent"). She got a kick out of the eMail exchange and shared it with me...

From "M" Jan 15, 2017

Hi "James".  I'm home, fed, and tired after work so its a good thing we didn't try to meet tonight.

Is tomorrow morning still good for you?  I think it'll work out very well for me and I love morning sex. How about 10?  I'm going to drive this time so can you tell me where to park and give me an address for my GPS?  I guess I could just aim for <the restaurant> where we met before.

So... when <Lauren> picked me up at <the train station> last night the first thing he said was "I love you" and I responded "I really hope so because I just fucked another man and liked it." He was very happy about finally being a cuckold. I thought you were very handsome, sexy, nice, and I like you.

I told him that we talked in the restaurant for a short time then walked hand in hand to your apartment.  You kissed me almost right away and we continued kissing then touching.  I could feel your hard cock through your jeans and I could already tell that you were bigger than him.  Then we moved into the bedroom and started peeling off clothes and I discovered that your cock is definitely bigger than his "little clitty" and that's why his tiny dick is locked up - it's just too small to be of use to me.  I told him that we laid down on the bed and touched some more and I got very wet for you. Then you said " tell me what you want" and  I said I want you to fuck me and you slid into me and you fit so much better than he does. You felt so good. Really good. (It's been a long time since I've been fucked, so it really was good). He asked if I tasted your cock and if you came inside me.  He insisted on licking my pussy clean.

I was happy with our date. I know <Lauren> was.  What were your feelings about the evening.  Did it meet your expectations?  I hope you really are excited about our next rendezvous.

It started out feeling a little weird to me but I moved past that about the time you took my bra off.

Looking forward to tomorrow.

M
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From "James" 15 Jan 2017

M

I'm happy to hear you shared with your husband our experience together. Your hubby sounds like the perfect cuckold. I enjoy hearing that you like the way I feel inside you. The more expressive you are the better. I like pleasing more than being pleased and it would seem that you've had to accept less than you desire or deserve. I like being in a position to fill this void.

You are very sexy. Beautiful full lips, lovely kisser, and luscious full breasts that I can't see myself ever getting enough of. I loved watching you suck my cock mostly because it appeared that you enjoyed it as much as I did. Entering you was pure bliss, so warm, wet, and inviting. I love hearing you tell me to fuck you. So hot hearing you express yourself...

My mind is running wild with images of not only what future pleasures you and I may have together but how and when we may invite your hubby. Having him watch in certainly likely. But I think you and I would like more. We can talk and discuss what ideas you may have.

Tomorrow at 10 sounds perfect. I'd like to have you come to my apartment door so I can great you with nothing but a bath robe on. But, I'll wait till you are more familiar. Tomorrow, you can park in the first floor garage as if you are visiting the retail area. If you forget where it is - on the back of the building - email me. The garage door will be open. Email me when you arrive, stay in the garage area and I'll come down to escort you the rest of the way.

Can't wait to taste you...

James
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I'll state here for the record that I was an insatiable sissy on the 15th. I couldn't keep my head out from between "M"'s legs that day, knowing that she was going to see James again the following day. She had more orgasms in that one day than she had ever had before in any single day (BIG smile)...

And yes, she DID meet him again the following morning at 10 o'clock. And yes, she DID come home after that with a huge smile on her face. And yes, I did immediately lick her pussy. It was an uncontrollable urge!

More proof that I really, truly am a sissy gurl! And LUVIN IT!

GOD I LOVE THAT WOMAN SO MUCH!