An Incredible Weekend!

While I was on my trip, M had two additional dates with James, and during our daily calls she told me that she masturbated several times while thinking about James fucking her. When she told me those things, it definitely brightened my otherwise dreary day!

I got home on a Friday after a full day of work followed by 22 hours of traveling... Needless to say, I took a shower, put on my clitty cage, and took an early afternoon nap for a couple of hours. M saw James on Thursday, so she was very perky when I got home the next day. The most memorable thing about Friday was that I spent a loooong time between M's legs worshiping her pussy and bringing her to a raucous orgasm. Of course I was wearing my my clitty cage and some of my frilliest sissy lingerie. M told me that I was to wear my Jailbird. I think she prefers the look of the steel... After her orgasm, and while we were cuddling in our bliss, she looked over at me and told me that she and James had set up a rendezvous for Sunday and that they wanted me there! She told me that James had sent her an eMail after their first tryst with a couple of Tumblr pictures and told her that the pictures showed things that he wanted me to do. She told me that during their second tryst (on Thursday), he then had her practice telling me to suck his cock. She added that it made her feel "weird" at first, but that after saying it a couple times, she "got into it" and actually got aroused at the thought... As for me, when she told me this, I got very excited... Thinking to myself that I would finally cross another "true sissy milestone."

On Saturday, during the day, I couldn't sit still thinking about what was going to happen on Sunday. I've always found it easier to put my thoughts into words so I can think of them more - it seems to "slow down" my communication so I can say what I really want to. So I often eMail M with my thoughts, and often attach pictures to the eMails to illustrate what I'm thinking about. So early on Saturday morning, while everyone else in the house was still asleep, I sat in the living room as I normally do - in the quiet calmness of the early morning hours - and composed the following:

Feb 11

It's so incredible being home... I feel so fantastic. So relieved. So much more comfortable. It seems that a huge amount of stress has been removed from me.

I was so happy when you told me to put on my clitty cage yesterday when I told you that I was going upstairs to take a shower. It makes me feel so submissive and so much better when you TELL me to do things.

You told me last night that you and James practiced ordering me to come over and suck James's cock. Hearing you say that last might was incredible for me. I can hardly wait to hear your voice as you say it for real tomorrow! I'm constantly picturing it in my head. I hope you'll order me to lick your pussy both before and after James fills your pussy with his cum. I hope that when James is fucking you that you'll tell him how good he is... How big he is... How much better he is than your sissy husband. I hope you'll tell me to watch carefully and see how a real man fucks a woman.

It really seems to me that you've become more confident with yourself, and that makes me feel fantastic. To see you like that. I hope I'm correct in seeing that, and that your confidence will continue to grow. I HOPE you'll be comfortable with me there while James plays with your breasts... While James plays with your pussy... While you suck James' cock... While James fucks you in every conceivable position... While you tell him to fuck you harder... While you tell him to fill your pussy with his cum...

I hope tomorrow you'll tell me not just to suck James' cock while he's making out with you, and that you'll not just tell me to put James's cock in you like a good cuckold should, but that you'll also tell me to clean your pussy after he cums in you. That you'll tell me to suck his cock after he cums in you to clean his cock and to maybe even get him hard again so he can fuck you again.

I really, really want to be your TRUE sissy cuckold tomorrow. Tomorrow is what I've been dreaming about for so long I can't even remember.

I love you

Sissy Lauren

Along with the note, I sent M a bunch of pictures... Some of them are below because they really, really captured what I was thinking.

Later on Saturday, M modeled the lingerie she was going to wear for her date. All I can say is WOW! Things she never, ever wore for me! Her ensemble was brand new and very HOT!

And then the big day arrived...

On Sunday morning, as I did on Saturday, I got up early and spent some time in quiet solitude in our living room, contemplating the events to come later that day. I was excited beyond belief, and felt I had to share that feeling with M...

Feb 12

Today I become a real, true sissy.

And I'm so incredibly excited about it!

I hope you and James will take complete charge, while at the same time remembering that it's all about YOUR pleasure.

Your lingerie is so incredible... So sexy!

And I'll bet that as soon as James sees you taking control of me - from the instant that the door to his apartment closes - that he'll get completely into it as well.

I love you so incredibly much!

Sissy Lauren

M's date with James was supposed to be on Sunday afternoon. She told me that we would meet him at a restaurant close to his apartment at about 2, then see where things went from there. She told me that we would only go to his apartment if we were all comfortable. It was a bit later that morning when she gave me the special panties she bought for me for the occasion. I was in absolute BLISS when I saw them. Incredibly pretty and lacy. Beautiful red with black trim..

M showered, lingering much longer than she normally does, while I got myself ready in some "big boy" clothes. She told me that she hadn't told James that I was a sissy, so she only wanted me to wear my panties and clitty cage as the tokens of my sissyhood. When she got done in the shower, M got dressed and packed her lingerie in a small bag. She and James had decided that when we arrived, and while I was kneeling in the corner, she would "disappear" into the bathroom, put on her lingerie, then make her "grand entrance." I found it incredibly arousing that she would choose to wear sexy lingerie and stockings for him without him even asking. It was a telling message to me that she wanted to look very sexy for him... To arouse him...

Long story short, we drove to James' apartment and parked. As we were walking to the restaurant where we were going to meet James, she looked over at me and told me that there was a guy up ahead who looked like James. I scanned ahead of us but couldn't tell who she was looking at. It was a simple thing, but she spotted him right away and I could hear the excitement in her voice when she said it. The anticipation...

When we stepped into the restaurant, she saw him sitting at the bar and immediately went over to him. She introduced us, and we left the bar area to get a booth. Another telling observation - without saying or doing anything special, she sat on his side of the booth with him. In doing so, she made it look completely natural - to be sitting next to him in a booth at the restaurant with me as the "guest" on the other side of the booth.

After a drink and some small talk, perhaps half an hour, we left the restaurant and walked to his apartment. Having been there before, M immediately went in while James put on some music and went to the bathroom. As soon as he came out and walked over to her, she looked over at me and told me to take off my clothes and kneel on the floor on the other side of the room where I could watch them on the sofa. I was in a bit of a daze as I stripped off my clothes down to my new panties and my clitty cage, then knelt down as she had directed me to. James took her into his arms and kissed her deeply, then they both sat down on the sofa and continued "making out" across the room from me. So incredible watching them! So natural... so "right."

It was only a short while before I saw her hand slip down and begin stroking his cock through his pants while he was kissing her. It was pretty obvious to me that his cock was already hard in his pants. Soon after that, he began fondling her breasts through her shirt. After a few more minutes in his living room, during which she undid his pants and began stroking his erect cock, she told him that she wanted to get changed. They separated and she picked up her small bag and went into his bathroom. While she was in the bathroom, he sat on his sofa stroking his cock and occasionally looking over at me as I knelt passively on the floor across the room from his sofa.

When M came out of the bathroom, she was breathtaking in her beauty. Heels, stockings, and incredible red teddy, and a matching red thong. Just remembering how she looked makes my clitty drip in its cage, even now. It was pretty obvious that he was impressed by what he saw, because he immediately got up from his sofa and walked over to her, taking her into his arms and kissing her again as he began caressing her openly in front of me.

They sat down on his sofa again, and began making out again. Fondling one another in an incredibly erotic exhibition of their lust. She paused and looked over at me and said the words I longed to hear so much: "Sissy, come over here and suck my lover's cock and make him hard for me." Of course "making him hard for her" was unnecessary in the extreme as his cock was already incredibly hard! But I immediately got up and moved over to where they were sitting on his sofa. I knelt down next to his leg and moved my head down toward his cock while they both watched me.

MOMENT OF TRUTH....

The head of his cock passed between my lips and I immediately knew... I knew beyond any doubt... Every reservation, every doubt, every shred of inhibition immediately left my body as I took his cock into my mouth. To say that it made me feel completely "right" would be a gross understatement. Having his cock in my mouth made me feel absolutely perfect. In every way. So hard. So warm. The skin so soft. His cock so smooth... Perfection!

While M and her man continued to make out on the sofa, I did everything I could to make his cock even harder than it already was. For me this was Nirvana. Complete BLISS. Complete HAPPINESS. Alternately sucking his cock and licking it. Wishing beyond hope that I could make him cum, but at the same time not knowing if he and M wanted me to. So I did my absolute best to TRY to make him cum, trusting that he or she would tell me to stop if they didn't want me to make him cum. Hearing his moans of pleasure, and feeling his hips moving gave me all the feedback I needed - I was doing a good job sucking a MAN's cock. Sucking a MAN's cock for the very first time in my life! I was so proud of myself!

I probably spent no more than 5 minutes sucking his cock while they were touching one another before someone (I can't remember if it was him or her) said "Let's take this into the bedroom." What followed was a cuckold's ultimate fantasy. His cock was obviously much larger than mine, but not "huge" from a porn video perspective. Seeing his cock enter M's pussy from behind as she leaned over his bed was fantastic. Hearing her moaning was so great. After a while, they moved completely onto the bed, and she prepared to straddle him. As she did, he told me to put his cock into her pussy. This gave me a short opportunity to suck his cock again for a short while before guiding it into her pussy. Yep... No doubt about it... MUCH bigger than my gurly clitty!

She rode him for what seemed to be a long, long time while I knelt down at the foot of the bed, taking it all in and occasionally hearing their whispers. I couldn't see what they were doing with their bodies in the way, but M told me later that he was alternately playing with her breasts while kissing her and sucking on her breasts. You can no doubt picture the scene - M wearing her incredibly sexy lingerie while thrusting her body down onto his cock over and over again.

They continued like this for a long time. I heard him whisper loudly to her "Are you ready for me to cum in you?" M's response was exactly what I wanted and needed to hear: "Yes, I want you to cum in me..." From the foot of the bed, I saw the urgency of their coupling increase to a furious pace. His body was slamming upward and her body was slamming down onto his. Just a moment later and I heard his loud moan as his cock thrust deeply into her once, twice, thrice as he filled her with his cum. For my part, my clitty was dripping uncontrollably at this point and I was in sissy heaven!

Just a minute later and their bodies separated, with her rolling over to the side next to him. A short moment to catch her breath and she told me to lick his cock clean, which I did with complete enthusiasm while she watched me. She then told me to lick her pussy while he got up and went into the bathroom to get cleaned-up.

M's date with James was everything I wanted and exactly what I needed. In the week after her date, I spent more time between M's legs licking her pussy than I ever have before. I couldn't seem to get enough of her pussy. My clitty dripped almost nonstop in its cage and I kept thinking about good it made me feel to have James' cock in my mouth. M told me that he sent her a note in which he told her that I came very close to making him cum and that he had do everything in his power to NOT cum... You can only imagine how GREAT that made me feel!

I felt SO HAPPY! I felt SO FULFILLED!