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!

She Does This From Time to Time Now

Not all the time, just when I least expect it.

I'll be sitting in the living room reading on my tablet while listening to the music channel on the TV...

She'll come into the room, and somehow migrate over to me...

Lean over and whisper something like this...

And when she does, my clitty immediately begins dripping.

Reflections on Being a Good Sissy Cuckold

I think being a real sissy (as opposed to a fantasy sissy if there is such a thing) carries with it an entire state of mind. We may be male, but our minds work differently than a man's. I may be a male, but I'm definitely NOT a "man." It's one thing to occasionally wear a pair of panties or some lingerie. It's one thing to be locked up in a chastity cage. It's one thing to have your wife call you "Lauren" or talk to you as a sissy gurl when you're in bed at night and you're between her legs licking her pussy. It's one thing to hear your wife say "I want a MAN to fuck me..."

Don't get me wrong... Those things are incredible.

But when your wife comes home after having sex with a REAL man... And when you spend the next hour or so between her legs licking her pussy whilst being dressed en femme. Ahhhhh. That's about as real as it gets.

When I picked my beautiful wife M up at the train station and she told me what she had done, a burst of adrenaline immediately shot through me and I almost had to pull over to the side of the road. Emotionally I was thrilled beyond belief. I felt a sense of utter contentment. Of absolute peace inside.

And at the same time, I felt closer and more in love with my wife than I ever had before.

And I wanted to somehow convey that feeling of love to her. To convey how happy and in love with her I felt at that instant. That very moment.

The act of her cuckolding me was an explicit affirmation... A black-and-white acknowledgement by her that she recognized and accepted me for who and what I am...

Not... A... Man...

I am a sissy with a tiny, gurly clitty.

I love it. I am so incredibly happy with it. I want to be and do all the things that a good sissy gurl should do.

From my previous trip down memory lane, you'll no doubt see that M thoroughly enjoyed not only her first date with James but also her second, which took place two days later. This reinforced my "sissy sense" and confirmed for M that I was not merely content with what she had done but that I was truly happy with it. We talked at length about her dates with James and, after a bit of unease at being completely descriptive about it, she shared more details about their two get togethers, all the things they did, and how good he made her feel. I think there was still some (very understandable) angst on her part - I had been her only "male" lover for decades. But I gently probed and got her to open up and to admit that he was better as a "Man" when making love with her than I was... MUCH better. This came as no surprise to me, but getting her to SAY it was a real breakthrough for her and (I think) helped her to remove some of her remaining doubts about me.

For days, I was running on a real emotional high. Wearing my most sissy-like things every day and taking every opportunity to have gurl-girl sex with M. And every time, continuing to reinforce her mental picture of James as a MAN and me as her sissy gurl with a locked-up gurly clitty between my legs.

And then I went overseas again and (because of my project there) fell into my very typical deep funk. Not only was it impossible for me to wear the things that felt right to me, but I also was unable to spend any time between M's legs licking her pussy and making her cum. Talk about torture! And it seemed (as it always does still) that our daily calls - while being a lifeline for me - were also torturous. They served as constant reminders of our separation.

My trip was 24 dreadful days... Almost a month... Purgatory...

She Knows What I Am

It's humiliating.

It's arousing.

It makes me immediately want to lick her pussy.

Every... Single... Time...

I Love Looking In The Mirror

I love dressing in my sissy things.

I LOVE looking in the mirror and seeing this.

It makes me feel so good... So right...

While I drool over all the different colors in my lingerie drawers, those that are pastels and those that are bright, there's just something special about classic black and white lingerie. Black always makes me feel so elegant. White always makes me feel so... virginal...

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
********
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
********

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!

A Short Interlude

I get this caption, I really do...

These days, my little clitty is caged continuously when I'm not traveling... The device is different (a sleek, stainless steel cage instead of a plastic tube), but I do wear stockings and other lingerie to the office all the time. Since that very first time when I pulled the stockings up my legs and reveled in the sensation of them against my skin I've loved that feeling. Putting on my sissy things every morning makes me feel completely ready to handle anything that might come up (freudian slip there) during the day.

And yes, I do wonder. All the time... I wonder what they would think...

And THAT makes me feel good too!

Our Maturing Sissy Relationship

The last couple of years have been challenging for me work-wise. I've been traveling internationally a lot more than I'd like in support of a really stressful project. Through it all I've made a very conscious effort to talk with my wife every single day - whether I was in country or out. I think my daily calls with her when I was traveling helped me keep my sanity in a chaotic world. It has been especially challenging because my travels take me to places in the world where being a sissy could get me a long prison sentence or even a death sentence. Talk about stress inducing. Whenever I was home, we'd continue our nightly discussions, and - more often than not - our Gurl-girl lovemaking. This brought me an inner peace and helped me feel safe. Reflecting back on some of my earlier posts in this blog, I think it has gotten easier for me to tell my story. Where it would have probably been uncomfortable for me to say something like "gurl-girl" lovemaking a month ago to an online audience, it doesn't now. That too makes me feel good. I think I'm enjoying the catharsis of "coming out of the closet" - even in the anonymity of a blog like this.

I mentioned in an earlier post how anally retentive I am - how I keep track of everything. I guess one could say I'm an electronic packrat. I wonder if there's an intervention for that?... In 2015, I was locked up (or unlocked but chaste) about 85 percent of the time and experienced a total of 35 orgasms, but only 12 were through traditional sex. In 2016, I was locked up or chaste over 90 percent of the time, and the number of orgasms I experienced continued to decrease - a total of 30 orgasms and 9 through traditional sex. But what's noteworthy about 2016 was that my last traditional sex orgasm was on October 11 - a trend that continued well into this year! The number of orgasms my wife enjoyed, on the other hand, went up significantly! And I reveled in the thought that she was finally getting the pleasure she deserved. My enjoyment, on the other hand, has shifted from what it was to ensuring SHE did.

Our nighttime fantasy discussions about her making love with (another) man continued, and - if anything - got more graphic and detailed. Notice that the word "another" is in parentheses. That's intentional. During this period, it became very apparent that my wife stopped thinking of me as a man and really began thinking of me as a sissy gurl. So perhaps the sentence should have read "Our nighttime fantasy discussions about her making love WITH A MAN continued..."

We got to a point where I no longer "cross-dressed," I just "dressed." We got to a point where she wouldn't think anything at all of calling me "sissy gurl" or even just "Lauren" when talking to me at night. I'd routinely send her cuckold-themed pictures, and I also searched for, and sent links to sissy-themed and cuckold-themed books on Amazon. Slowly, oh so slowly, she came to understand that she shouldn't feel guilty for "having those thoughts," especially given a sissy husband who actively encouraged them. This was a big deal for her given her somewhat strict religious upbringing. She loved me. I loved her. No doubt about it. She had one sexual partner before me. I had one sexual partner before her. I never pleased her as a man, so I did everything I could to get her over the mental hurdle of A) seeing me not as a man (which was true anyhow but she would sometimes cling to that memory), and B) seeing herself WITH a man. She was so incredibly afraid of hurting me - realizing without saying it that once the bell has been rung it can never be "un-rung." We talked about this and I encouraged her for months, emphasizing over and over again how much I loved her and how much I wanted to see her get all of her needs fulfilled. With her acknowledgement of my sissyhood, she was already fulfilling mine!

During this time I was also actively reading a number of other sissy-related blogs and saw so much of myself in them, at least in the ones I read regularly. I sent her links to these as well, and encouraged her to read them. I know she did because she'd sometimes bring up topics for us to talk about that came from those blogs. And when she did, we'd talk about other sissies, their relationships with their wives, and the challenges they encountered. Each time we did, it got easier for her to talk about cuckolding me. To talk about "being with a man not her husband."

And I was so happy...

Early in 2016, our cuckolding discussions rose to a new level when she told me that she was actively looking for a MAN... A MAN to be her lover... To say I was thrilled would be an incredible understatement! I redoubled all of my efforts to please her as her sissy gurl and was often rewarded by her orgasms brought about by my oral ministrations. I was incredibly distraught (as was she) when her first potential suitor didn't work out. Fortunately they never got to the point where they met, and I'm glad they didn't. Through all of her / our correspondence with him, it just didn't feel "right." Somehow I got the impression that he was a troll - a lot of words, a lot of fluff, but no substance. This put her search on hold for a while because she got a bit depressed about it and her self-image suffered a bit, but I kept encouraging her to not give up.

And while all of this was going on, I continued my project-related international travel. And upon my return home after every trip it always - without fail - felt so good to get into what were, by that time, my "normal" clothes... (Big smile here) - I remember my wife once saying to me: "I get home from work and the first thing I want to do is to take off my bra... YOU get home from work and the first thing YOU want to do is to put ON your bra..." How true! That AAAHHHHH feeling!

And late in 2016, everything changed...

For the better...

Sissy Gets Her Name

Well, for what it worth, the "history" is almost done. Although I'm quite certain that I'll continue to add to add to it over time... "Oh-by-the-ways" I guess.

As time went on, my perception of myself became more and more clear. This will probably be an interesting - and challenging - post for me to write. I've got some things I want to say, but I don't want them to come off as being superficial or phony... This is something that's incredibly important to me - being who I am - my acceptance of who I am. And the relationship I've got with my beautiful wife is deeper than most people can possibly imagine... We were two lost souls brought together decades ago by chance. Through it all we've somehow grown together and flourished. Over time our relationship has become deeper and more complex, a melding of flavors into a simple yet magnificent dish... The kind you can't get enough to eat. The kind you always come back for. The kind that's always there in the back of your mind... So when you read this, you should consider that context. In this case, the context is everything.

April 2014 was another milestone for me. It marked the first time I bought lingerie for myself. My wife was already accustomed to seeing me wearing panties and the occasional camisole. I was wearing panties almost every day. And I was feeling better about myself than I had felt in (literally) decades. But all the panties and lingerie I wore were things that my wife "donated" to me. I think the act of buying my own lingerie was an explicit affirmation of who I was.

So in April 2014 I bought my own lingerie. Stockings and a really sexy garter belt. Putting them on for the very first time made me feel phenomenally good. Here's the actual picture I saw when I ordered the garter belt. Those of you who are sissies like me know exactly what I'm talking about... The indescribable feeling of the material against your skin. The knowledge that YOU bought it for yourself. The angst of wearing it in front of my wife for that very first time and wondering what she would think...

After that order, I began ordering lingerie for myself more often. Not all the time, but whenever I felt the need to get something special for myself. My wife took that cue and began ordering more things for me as well - including matching bra and panty sets. I was in heaven! Wearing my own lingerie made me feel so "right." Wearing sexy things that my wife had bought for me made me feel special. When I traveled for business internationally and couldn't wear "my things" I felt like something important was missing. It always felt so good (and does today) when I came back from a trip and could dress the way I felt. My wife would sometimes pick me up at the airport and would tell me that she had laid out the things she wanted me to wear when we got home and I got out of the shower. What a special woman!

I was locked up most of the time. I still had "traditional" sex with my wife, but less and less frequently. It was apparent to both of us that she preferred oral sex (me going down on her) much more than she preferred our traditional lovemaking. Don't get me wrong, orgasms felt great. But I always experienced a huge emotional letdown after having an orgasm - knowing that I hadn't pleased her and that she felt she was only doing her wifely duty made me feel terrible, especially given how I now thought of myself - as a sissy. We talked about that often...

My nighttime discussions with my wife continued to evolve. We talked more about how I didn't please her when making love with her as a "man" but definitely did when I made love with her as a sissy. Somehow that didn't bother me at all. Perhaps that's because I already knew that I didn't please her with my "manly" lovemaking. It always left me frustrated and emotionally drained, even if I was never courageous (to that point in my life) to confess my feelings to her... She didn't yet use the term "sissy", but she kept encouraging me to not make love with her as a man, but to do so in the only way that I DID please her. My orgasms went down in number and shifted slowly. Where they were previously almost exclusively from penetrative sex, they became more from her stimulating me manually, or having me masturbate while she watched. The shift was slow, but apparent to me. And the first time she told me to play with myself while she watched my heart just about leapt out of my chest! Especially when she said it made her wet to watch me...

My periods in chastity increased in duration. I felt more aware... More aroused... Energized... More feminine every day it seemed. And it felt GOOD to me. Being out of my chastity cage and trying to make love with my wife as a "man" felt somehow wrong... Abnormal... I loved being between my wife's legs, cuddling with her and playing with her breasts while dressed en femme. I loved that there was no pressure on me to initiate penetrative sex after that. I loved that I could play with her for long periods, then slowly kiss and lick my way down until I finally reached her (invariably soaking wet) pussy and gently begin pleasuring her. This is what I wanted. This is who I was. This is who I wanted to be. And my wife - God bless her - accepted and supported me completely.

Slowly, we began to have deeper discussions about her desire to still have penetrative sex. To feel a man's cock in her. Yes, I already knew about cuckolding. Yes, I already knew about her college boyfriend having sex with her and making her cum. Yes, I had already been cuckolded by my first wife. And no, it wasn't her who brought it up...

It was me.

I don't remember the exact day that the topic crossed my lips, but I do remember asking her to fantasize about a MAN fucking her one night while I was between her legs licking her. By this time, she was calling me "sissy," "sissy gurl," or (to my great happiness) "sissy Lauren." and referring to the locked-up thing between my legs as a "clitty," which always aroused me. I remember looking up from licking her to see her with her head thrown back, lips apart, eyes shut, and her hands pulling and pinching her nipples in ecstasy... An incredible view into her fantasy as I continued to pleasure her orally. It made me feel incredible inside, and I confess that my clitty was dripping profusely. It wasn't so much a "fantasy" for me to think about my wife cuckolding me as it was a fervent (and very, very real) desire on my part to know that my wife was getting all the physical pleasure she (deep down) needed but was afraid to ask for. But the mental picture wasn't bad for me either...

For a long time, our lovemaking followed that model, with occasional variations on the theme. I would begin by stimulating her breasts, then begin verbally painting a picture of her with a man...With her making love with a man and thinking of all the things they would be doing together. A man with a real cock instead of the tiny thing between my legs. A man who could have sex with her for more than a minute before cumming. And all the time I would be gently licking her pussy. Getting her more and more aroused. I'd occasionally ask her to describe what she was fantasizing about. I'd occasionally ask her to play with herself while fantasizing about a man making love with her. I'd ask her to play with herself while comparing the man in her fantasies with me - her sissy husband... The scenes were very arousing to me as a sissy, and seeing her in such bliss made me love her even more.

Kinky? Definitely. I knew that I pleased her when I made love with her as a sissy. Much more so than when I pretended to be a man. But at the same time, I knew that she wanted and needed "real sex." But given her upbringing the emotional guilt for her was incredible. Even today, several years later, she still has occasional pangs... The most important thing for me though was that she be happy - emotionally and physically. She had already done so much for me by being so supportive, accepting, and loving for me for so many years.

And a Blogger Discovery...

How interesting...

My normal web browser is Firefox. When I access my new blog using Firefox and try to respond to a comment, here's what I see. Notice that that the first item is "Google Account." What's interesting is that I CAN'T respond to someone's comments using Firefox. I think it's a script thing.

But when I open my blog using Internet Explorer, then do the same things, I see that the generic "Google Account" is automatically replaced by my Google Profile information as shown below, and I have no problems responding to comments. Seems that IE "remembered me" where Firefox didn't.

 

This is something I'll have to look at. It COULD be a cookies thing... It's very possible that I've got cookies turned off in my Firefox browser (remember that "I don't like sharing any information with anyone" thing I've talked about in my blog??).

"M" Learns More About Who I Am

(Sigh) Allow me to ramble for a minute...

There are lots of links to Blogspot sites about and for sissies. Unfortunately, it seems that many of the sites are either deceased, shills for junk, or just placeholders for "future content." In looking at some of the sites that I browsed through, it seems that there is a lifecycle period of three to five years. The sites start out so promising. But after that period of time, they just end. I don't mean that they slowly peter out, I mean that they "fall off a cliff." One day the blog author is enthusiastically posting and the next day there's nothing. I wonder why that is? Perhaps a move to a different place? Perhaps the creative juices dry up? Perhaps some sort of personal crisis? Or something else altogether?

If you've read my blog so far, you'll see my recognition in my early life that I was different than other males. Physical characteristics notwithstanding, I was different in my head as well. I think three things contributed to the turmoil in my head:

• I grew up in a very patriarchal household where gender roles were very traditional and fixed. You were either a boy or a girl, man or woman, defined completely by what you had between your legs. A very loving household - absolutely - but rigid.
• When I was young, I didn't have a lot of friends of either gender. Moving around a lot contributed to that, but I also tended to not make friends easily. As a young child, I just didn't gravitate to other boys as close friends, and knowing that girls had cooties and boogers didn't make them appealing to me either.
• I grew up as a "loner." Lost in my own world in many ways. As a loner, I looked at the person-to-person interactions going on around me (and yes, I OBSERVED them in silent solitude a LOT) and just wasn't comfortable in my own head with the notion of traditional relationships. I just couldn't see myself in those kinds of interactions so I withdrew even more.

Don't get me wrong. I don't mean to present an image of myself as this solitary loner who grows up to be a serial killer like you see on the news. Not at all. I engaged with others all the time. I laughed. I played. I had a great mom and dad who encouraged me to explore lots of different things. I DID lots of things with others. I just didn't have close relationships with others while doing all those things because I felt different.

As I entered my teens, I still didn't engage in friendships with other males. It seemed easier for me to build relationships with girls. At least talking relationships. Not "boyfriend-girlfriend" relationships. Not deep "bare your soul" close relationships by any stretch, but "get to know you... friend zone" friendships. And I was comfortable with that.

When I matured, my differences became more apparent to me, and I kept them hidden. Outwardly, I presented this "manly man" image. Inside I was in turmoil. Emotional agony.

And then, around the turn of the century, reconciliation and acceptance. Emotional freedom. We're talking "breath of fresh air" freedom. And it felt (and feels) so incredibly good!

The decade we're in currently has been a decade of change, of growth, and of exploration and discovery. It started with my wife buying my chastity cage and (tentatively at first) clicking the lock. It continued with routine, open nighttime discussions about her, me, what we're thinking and feeling, and what makes us happy. I told her that I wanted to wear panties and other women's underwear and lingerie. Pretty quickly she started putting some of hers into my drawer. Not that we were the same size at all, but given today's stretchy materials it somehow worked out. In fact, she bought me some panties. Nothing frilly, nothing lacy, just plain bikini panties in a variety of colors. God I love that woman! Almost right away I was wearing panties all the time. Every day. At home... At work... Everywhere. That simple act was an affirmation for me and I saw myself becoming more and more outside like the person I felt like inside.

Exploration and discovery progressed slowly, but pretty consistently. Nothing that really "pushed boundaries" in any kind of huge leap, just slow and steady progression. Where she kept my locked up for only short periods of time at first (think "chastity play") and unlocked me pretty regularly for "traditional" lovemaking, I noticed that more and more often I would end up with my head between her legs or cuddling and snuggling for long periods of time. And I was fine with that because I loved it and because I didn't have to feel bad anymore when I tried to please her like a man and failed miserably.

I regret to say (only because it's a character flaw that I have I guess) that I'm anally retentive - I keep track of details over long periods of time. Thus I can honestly say that in 2013 I got my Christmas present chastity cage, that we had it for 348 days that year, that I was locked-up for 229 days that year and that my longest period locked was 16 days, and that I had a grand total of 35 orgasms that year.

Remember how I said in an earlier post that my wife finally confessed and told me that I had never really pleased her when I made love with her as a man? Well... 2013 was the first year I kept track, and (I guess I'm proud to say) my wife's orgasms exceeded my own. Given that early (and for a long time thereafter) into our marriage I didn't engage in oral sex with her (to my great chagrin now), she spent a LOT of years without an orgasm that wasn't self-induced. So her orgasms in 2013 that I kept track of were due to me "practicing my technique" orally. And knowing that I could make her cum orally where I couldn't do so through penetrative sex reinforced my self-image even more. I've seen chastity blogs where it's said that keeping a husband locked up results in a lot more (and better) oral sex for the wife. I'll confirm that's true... On both counts!

And as long as my wife was getting the pleasure she deserved, that was all that mattered. The fact she accepted me for being "different" was just icing on the cake! She didn't know HOW "different"...

Yet...

Clarity

For about 3 years, from 2008 until 2011 my job took me to a part of the world where having the kinds of thoughts that I was having was a very dangerous thing. The kind of thing that could earn you a death sentence. But it's interesting what you can find if you set your mind to it. I was already actively searching the Internet for more information (and yes, of course erotica) about "those like me." But when I traveled, I couldn't do any of that because all of my normal websites were blocked. But of course there are ways around the blocks. Interestingly, I learned that the US government actually sponsors some of the technologies that enable people to bypass government Internet access controls. So I installed a VPN tunnel on my personal laptop and continued to browse. That worked for a couple of years, sometimes better than others, but at least it was something...

It was during those years that I explored this thing called "male chastity." It was during those years that I learned more about "feminization" and being a sissy. It was during those years that I learned more - oh so much more - about separating the fantasy from the reality. It was during those years that I finally discovered my sense of self. It was during those years that I finally accepted who I was and was able to articulate to myself what that meant. It was during those years that I discovered the courage to open a dialog with my wife. Slowly. Gently.

I remember saying out loud to myself for the very first time... "I... Am... A... SISSY."

And saying it to myself - out loud - made me feel GOOD about myself. Having the ongoing emotional conflict that had gone on for so long finally resolve itself made me feel so incredibly GOOD!

I discovered so many erotica websites. So many blogs. So much information. It was hard separating the fantasy from the reality. At least at first. I think I got better at it as time went on. The sites that I felt were "real" I continued to visit. Those that seemed to be more fictional I began to bypass. Yes, of course I still visited some of them from time to time to arouse my prurient interests, but less and less frequently.

A quick sidebar! It was during this time that I also discovered that many of the sites I visited also tried to download computer viruses to my machine! Yes, I got spammed. Yes, I got viruses. Yes, I got really good at re-imaging and rebuilding my machine from backups. I'm a lot more careful now. A LOT more.

In 2011 I made a chastity device based on what I had read and the pictures I had seen. A "home built." Being pretty creative, and being pretty good with tools, it was actually quite nice. But I kept it secret. By this time, I was spending more of my time (when I was home) wearing panties and (occasionally) pantyhose. But they were my wife's, not MINE. This too I kept secret. But I wanted my own panties. I wanted my own "girly things." When I was in bed with my wife, I'd initiate discussions more frequently with her about what she liked and didn't like. I'd initiate discussions with her about her life before we met. It's during this time that I learned about her college boyfriend. It was during this time that I learned that I never made her cum when we had sex. It was during this time that I learned that while I couldn't please her when making love with her as a man, I could very definitely please her when I made love with her like a girl. And these things confirmed my sense of self. They confirmed that I really was different from a "man." Beyond the obvious size difference I mean.

In 2011 and 2012 I was traveling internationally for business quite a bit. Sometimes to places where I felt I was still in the dark ages if you take my point. Sometimes to places that were much more civilized. When I was home, I spent a lot of time in my home-built. But uncaged whenever I was on the road. When I was home, my wife and I would continue our discussions about sexuality. I would wear my home-built chastity device often during the day, but would take it off at night when I was in bed with my wife. I loved how it made me feel. I would raid my wife's panty drawer often. Sometimes now I wonder if she noticed... Wearing my chastity device and panties didn't feel weird, it felt completely "right."

Slowly - ever so slowly - I got her to open up. Got her to tell me more about what she was thinking. And at the same time I tried to put MY feelings into words. I've read so many times about those who just dumped everything on someone in one shot, like ripping away a Band Aid. That was definitely NOT the case for me. Maybe I was scared. Meh. I just felt more comfortable taking things slowly. It seemed that peeling back each layer of the onion made it easier and less traumatic when I peeled back the next layer. Sometimes I smile when I think of those days and our discussions... Feeling our way through.

When I was traveling, I talked with my wife every night. Every... Single... Night... And I eMailed her almost every day as well. Having discovered the miracle of Blogspot and Tumblr, I was doing a lot of browsing and looking through images - almost always captioned. My eMails would almost always include pictures with captions that portrayed how I was feeling on any given day. Invariably chastity-related. Or dominant-wife related. Or sissy-related.

Late in 2012 I told my wife that I was interested in chastity. I don't think it really came as a shock to her as we had talked generally about the topic a lot, and many of the images I had sent to her portrayed chastity-related themes. What made the discussion stand out was that I asked her if she would buy me a chastity device for a Christmas present. Having done all my research, and having had some experience with my home-built device, I even sent her the link to the site. And so it was in January 2013 that my Mature Metal Jailbird arrived and life as I knew it changed forever...

And the mental picture I had of  myself came into clearer focus...