Transition Update

Life has been so busy!  I am continuing with my gender transition.  I’m working with some of the best professionals in my state, which rocks.  8 months now on female hormones, and I definitely have some cute breasts.  My wife loves to tease me about how much larger my ass is (yet she says she loves my “girl butt”).  I have filed paperwork to legally change my name, and have started talking to gender reassignment surgeons.

This week I’m going to talk to HR at my workplace to set plans in motion to transition on-the-job.  One day I will simply start as a female.  Yes, really.  I’ve learned my employer has recently gone through this with someone else already, which is heartening.  I’ve been living as a female for many months now everywhere in my life except at work.  It’s time to come out there and go “full-time”.

I received a comment or email from a reader who wondered if becoming a transexual was a natural or common eventuality for a feminized husband in chastity.  My short answer: no.  It’s a great fantasy, and I’ve loved the stories I’ve read on-line over the years.  But the reality of changing your gender for real in this society is very different.  I’m sure there is the occasional “forced” situation, but I estimate that’s far less than 1% in real life.  What you don’t realize is that there are plenty of transitioning people all around you.  Some estimates as low as 1 in 200.  Of course that includes the entire transgender umbrella, not just transexuals.

Some of the women you know might have been born male.  That’s just reality.  But please don’t ask them.  Think about it — a genetic female will likely be very offended that you thought they were born male; quite a buzz-kill on a date.  Like me, most transexuals want to transition and live the rest of their life as peacefully as possible.  I just want to be in the world now as a woman.  Eventually I will legally be female.  And my wife and I will simply want to get on with the rest of our (lesbian) lives.

Some aspects of my situation were not really that unusual:  a lifetime of private activities exploring my female side (crossdressing, reading TS stories, playing with makeup, wishing I was female); deciding to explore it more seriously after getting heterosexually married.  One aspect of my situation is very unusual:  my wife and I plan to stay together.  The harsh reality is that most relationships cannot survive one spouse changing their gender — I think the partnership failure rate is over 90%.  The suicide rate for transgender people is also very high (over 30%) — I’m fortunate to be a survivor, in fact.

But back to the question.  It very well could be that a husband willing to be feminized and put into chastity does have some latent gender identity issues.  But they may not be as serious as full-out transexuality.  There is nothing wrong with loving to crossdress (I did it for decades), and for many it ends there.  Other have a stronger pull away from their genetic gender, but life circumstances prevent them from acting on them (I was also there for decades).  A full transition is not cheap — at least $30,000 start to finish.  If you are interested in more details of transitioning, let me know.  I don’t want to bore my readers!

Let’s revisit my dog dish (see prior post).  I haven’t messed up once!  But I will relay one story.  My wife’s sister moved to our city about a year ago, and she comes over sometimes to chat or eat — or the three of us girls go shopping!  One day she was over and she brought her two little dogs.  I came home from work and saw my dog dish on the floor, and her dogs were eating out of them.  I didn’t know if my wife had told her or not.  And I didn’t dare ask.  But it was clear that my wife noticed me noticing, and she really got off on the humiliation that it provided.

I’ll end on a chastity development.  Today I’ll be removing my PA piercing.  That’s a major deal for me.  I’d wanted that ring in my cock for so very long, and it meant so much when my wife decided to have it installed.  But gender surgeons apparently recommend letting that hole in my penis heal.  I guess it makes sense, since they will be turning tiny inside-out when they surgically transform my male genitals into a vagina and labia.  It’s amazing what they can do today (google for “SRS photos”).

But removing my PA ring signals the end of an era.  No more chastity.  Having my cock locked up was such a focus and big deal to me.  And I’m feeling some loss about that.  Mistress still dominates me, of course.  But not with forced orgasm denial.  She’s threatened a female chastity device, but those always come with a waist belt, and she has never been ok with those.

At some point I’m going to sell my whole high-security chastity setup:  lock, JailBird cage, bio-safe, etc.  If you want to be notified, drop me an email or blog comment.  That will be a sad day too for me.  On the other hand, it truly does feel awesome in so many ways, to finally become the woman that I’ve dreamed of being — and to have my Mistress/wife with me on the journey!  Heaven!

A New Phase

Well, it looks like I’m well on my way to never needing to have tiny (my wife’s name for my cock) locked into a chastity device.  Several times she’s happily remarked on how well my “chemical castration” is coming along.

What she’s really referring to are the hormones I’m on as I progress in my transition to becoming female.  I’ve been on estrogen for 2 months now, with maybe a little breast, and hip growth (but hardly any so far).  The sprio though, which blocks testosterone, is what she was referring to.  It reduces the male sex drive and, over time, shrinks the testicles.

Recently I realized that my PA ring may not be long for this world.  It was integral to the 100% secure stainless steel chastity cage we used not that long ago.  But it’s getting uncomfortable now that I’m tucking my junk away to look more feminine “down there”.  And sometimes that damn ring gets really uncomfortable, squishing things in strange ways, particularly when sitting.

It also occurred to me that it may be a problem later when I go to have sexual reassignment surgery.  Since, basically, the penis is turned inside out to make a vagina, it probably won’t be good to have a hole in it.  That’s 1-2 years away at this point, but still something I’m thinking about.

I asked Mistress about it recently, and she suggested that I may as well just remove the ring.  That was a bit of a shock to consider, since my PA piercing will probably close up and heal over pretty quickly (a week or two maybe?).  What shocked me was facing the end of serious male chastity in my life.  Funny, that hit me harder than not having sex.

The extensiveness of this blog probably makes it pretty clear that chastity was a pretty important thing to me.  Masturbation, sex, and male orgasms certainly were also.  But they aren’t any more.  I’ve changed, and I’ll continue changing.  Not only has my male desire for sex been suppressed, my whole sense of sensuality is changing.  I’m amazed at how erotic simple touching can feel now.  I’ve always been a tactile-sensitive person, but hormones have turned it up to 11.

Anyway, lately I’m coming to grips with letting go of my manhood.  Chastity represented that, in a way.  My cage was an illustration of how I needed to have it controlled, lest it be out of control.  Thinking about selling my awesome metal penis prison makes me sad.  It’s a rite of passage, I suppose – if atypical.

Of course, to see me typing this with my hair up and wearing this bright, fun sun dress – you wouldn’t guess that I’m struggling with my masculinity.  And I’m not, really, I’m doing well at letting that go, because I feel so great as a woman.  But chastity – wow, letting go of that part of my life is harder.  Necessary, but a heart-felt loss.

In terms of my transition, I’m living at home and in public as a woman over half the time that I’m not at work.  My immediate family knows (parents, children, siblings), and probably 100-200 friends.  We have new friendships in the transgender and transexual community, which is wonderful.  This fall I plan to come out at my workplace, which I’m expecting to go well.  Between then and now I’ll be legally changing my name.  Serious progress.

It’s been busy, with extra appointments, investing time in new relationships, additional shopping to get my closet ready for going full-time, hair removal activities (laser, IPL, electrolysis), etc.  Mistress and I are both really looking forward to the time when we can just get on with our new lives together, without so much focus on these transitional steps.  Again, necessary, but sometimes frustrating.

And she is excited to be growing into a lesbian relationship.  Being bisexual, this is seriously working for her.  She can’t wait for me to have fuller breasts, a vagina she can have men of her choosing use, and labia she can torture.  After all, I’m still her submissive pet, regardless of my gender.

Just thought I’d update everyone.  Thanks for reading.  As always I’m open to questions and comments.

Hanging free for now

Mistress gave me an orgasm on Friday. It had been 48 days since my last one, and I was securely locked up for the last 35 days.

I had a doctor’s appointment the next day, one that included a genital exam. So she wanted me to take it off (I would have been fine leaving it on, and it wouldn’t have gotten in the doctor’s way at all). Mistress masturbated me while biting my chest. It didn’t take me long.

I don’t think she realized it, but she stopped stroking right as I started to cum. I begged her to keep going, and after a short pause she did. Fortunately I had another climax and got to fully unload. There was a ton of fluid. No surprise, I suppose, since it had been almost 7 weeks of celibacy for me. I was worried that she was going to give me a “ruined orgasm”. That would have really sucked!

The doctor appointment was with my endocrinologist — the one who will oversee the female hormones that I am likely to be on in a week or two. She did a health history, advised us about the risks, did a quick physical — including the genital exam and a prostate exam with Mistress watching! Yesterday I had some blood drawn for lab tests, which should show me healthy and ready for hormones. About a week for those test results.

Mistress told me today she’s looking forward to me having a pussy. She has plans to fist me in a variety of ways, and was telling me details today. She want to fist my pussy and the pussy of a friend of ours. She’s done us both before, but obviously one of her hands was up my ass then, the other in our friend’s vagina.

She also wants to double-fist me – one in my pussy, and one in my ass. And she’s talked about the various dildos she plans to use to fuck me. (I wish she’d fuck my ass now!).

Another thing she plans to do is have people watch while she sews my labia lips together (explicit image here). And yes, she’s completely serious and I fully believe she will do it.

Not sure what she plans to do about keeping me in chastity once my easy-to-secure cock becomes a tempting pussy. She’s never liked the full waist-belt style metal chastity belts, but maybe she’ll end up locked me into one. Not sure how else she’ll be able to control access to my eventual clitoris otherwise.

For the moment Mistress has decided to leave me out of the cage. It will help me crossdress more effectively (and comfortably). A few months back you may recall that I signed a written chastity contract with her. It clearly specified that I must avoid all masturbation or stimulation of my genitals, and that I have turned over all of my sexuality and control of my cock and balls to her. So even though I’m not locked in the JailBird, I am still “in chastity”. And I fully intend to be faithful to her and our contract.

Boundgasm

My spouse, Mistress, and keyholder took me to a kinky party yesterday, but left me in chastity. However, I was luckier than another guy we saw there.

It’s been over 5 weeks since my last orgasm, and 23 days of continuous lock-up in my JailBird + PA-lock. Last night, though, I watched a poor guy get teased to an unbelievable degree — and he’s been denied orgasms for 57 days.

His owner had bound him (naked of course) to a suspended leather sling with plastic wrap in the dungeon at this party. She then proceeded to sexually tease him for a solid hour, stroking his cock and stopping before he could orgasm. A small audience watched.

If he got too close, she would give him some “distracting pain” to “help” him avoid an orgasm. Things like slapping the head of his cock really hard with her hand, or grabbing his balls and squeezing them hard. He got close to cumming time after time after time. But he never spurted.

I’m not sure what their agreement was, but he was begging not to orgasm. In the end he got his wish, but not before what seemed like an unbearable amount of substantial penile stimulation. His owner knew how to get him off, her hand-job technique was clearly effective. He was hard the whole time, and making the most interesting noises throughout.

His scene was still going on when Mistress decided it was time for me to submit to her and our friend. She took out our lightest leather bondage hood and secured it tightly around my head. It has a snap-on blindfold and a snap-in gag, which she left out initially.

She led me over to a bondage table, with webbing for dozens of straps to bind the limbs and torso. I’d been on it before, and knew what to do. I removed my clothes and got in position to be tied down.

Mistress kept it simple, using just 5 of the thick nylon straps to secure my wrists, ankles, and waist. Our friend joined us, and I was then blindfolded and gagged. They wasted no time and started tickling me mercilessly. I recognized the voice of the owner of the other chaste male who was tickling my feet and really enjoying watching me thrash and squirm and (try to) yell. Mistress and our friend were at my sides tickling my ribs. I felt completely out of control as my body tried uselessly to move away from the excessive stimulation. They all seemed to have a great time.

Eventually they stopped, and Mistress directed our friend to help calm me down with “smoothing” hand motions on my skin. My breathing slowed, and I settled down.

Then I felt her start stimulating my nipples. Mistress whispered to me that she wanted me to orgasm in front of everyone in our new special way. I nodded to let her know I understood and would try. At this point we’ve only done it a few times, and I wasn’t sure I could do it there in the dungeon. But, wanting to please her, I was going to try.

The nipple stimulation continued, and I continued my deep breathing, focusing not on my cock but on the growing sense of sexuality throughout my body. My cock doesn’t get very hard during these experiences — it’s not a penis-based orgasm. I felt the sensual energy building inside of me.

Then she was biting me. Mistress’ teeth dug into the flesh of my chest as her fingers continued their very arousing motions on my nipples. Then our friend began biting me on the other side, and licking my nipple as she sucked my breast skin into her mouth. The pain mixes with the pleasure for me, taking me deeper and farther.

I heard Mistress ask me if I needed more, and I nodded. The two of them continued stimulating me and biting, until finally I went over the edge. My body shuddered and I felt flushed. I strained against my bonds as I tried to arch my back and spread my legs as the orgasm spread through me. They continued stimulating me and pushing me on, until I went limp. Mistress reminded me to continue breathing as I recovered.

I wasn’t sure what to expect at the party, but it was a very nice scene. Mistress seems very interested in exploring this alternate way of pleasure for me, and she continues to show no interest in my cock. I think it’s her way of encouraging my new female sexuality to emerge.

A number of people seemed surprised when I got undressed before the scene. But I wasn’t sure if that’s because they didn’t realize I was a guy (I was wearing a new hot dress for the party), or if they hadn’t seen a stainless steel chastity cage like mine before. Either way, I was fully on display for quite a while. Being blindfolded, I have no idea who was watching during our scene.

A short while later I was dressed again, fetching Mistress some food and then massaging her feet as she chatted with others. A little while later we were back in the dungeon watching several other scenes, while I was Mistress’ footstool. It was a wonderful evening.

Having it Her Way

We’ll be going to a kink party next week. Mistress isn’t sure what she plans to do with me then. But we do plan on having me come out to everyone (as a transsexual).

They already know me as a part-time crossdresser. But my persona at those times was a ditzy, funny, slutty, “blonde” female. Of course my new presentation will me instead. It will be interesting.

We fully expect everyone to be quite supportive. The BDSM community has plenty of GLB and T folks, and we personally know many of them. So the risk is low here for coming out. A few already know.

Mistress talks about my post-op situation sometimes. Once tiny (her name for my cock) has been turned into a vagina, she has plans for me. One is to fist me. She also plans to fist me and another woman at the same time at one of these parties. The three of us have done that once before, but next time will be different (3 women).

She’s also talked about finding men to “have their way with me”. She’s mentioned some specific names too, and that she plans to talk with them about their interest in having sex with me after my surgery (and after healing of course). She’s also mentioned setting up “rape scenes”, which excites me too.

I’ve realized that one of my core aspects is finding pleasure in providing sexual pleasure for others. I love it when Mistress orgasms using me in various ways, particularly when she ignores what she calls “my poor excuse for a penis”. And I realize that letting men eventually use me for their sexual pleasure is almost certainly likely to leave me feeling the same way – satisfied that they achieve orgasm, even (and particularly) when I don’t.

However, I understand that I’m likely to be orgasmic after SRS (Sexual Reassignment Surgery). Although I’m certainly looking forward to that, Mistress has made it clear that she plans to have me in chastity then as well. So at some point I guess we’ll be investing in a female chastity belt.

Surgery seems like it’s about 2 years away, possibly a little less. I’m hoping to be evaluated for female hormones later this month, likely having a prescription within a month. Time to grow breasts!

Mistress talked with me about my cage today. She insists that tiny will remain locked up for now, with no releases planned. She said she was unhappy with my behavior during my week out of the cage a month or so ago. I don’t recall specific problems, but I’m in no position to argue. It’s just a bit of a hassle to try to tuck my male parts out of the way when I crossdress, due to this stainless steel cage locked onto them.

Another one of my core aspects is being submissive to Mistress. As I transition from a male into a female, I fully expect to remain submissive to her. That is what we both want. I will remain her chaste, submissive pet.

Morphing Normality

It’s been 12 days so far in chastity this time, and to be honest, I’ve hardly noticed. It’s just the way things are now.

Sitting to pee is just second nature, I hardly think about it. About the only time it registers is around showering. And even then it’s just procedural: wash it, dry it, put a little lube around the base ring.

You’d think having a tight stainless steel locked to your penis would be a bigger deal.

We’ve had the JailBird for almost 4 months now, and I’ve worn it at least 95% of that time. Male orgasms appear to be a thing of the past now. They are simply not interesting to her at all any more. I don’t even find I crave them that much, although I suppose I could easily fall back into the masturbation habit. I don’t want to, though.

Now that I’ve experienced (what seems to be) female orgasms, there’s just no comparison. The last time we did that, tiny (her name for my cock) was only a little bit hard, barely at all. Mistress stimulated my nipples, touched and rubbed me elsewhere on my upper body, and guided me with her words to relax into building wave after wave of sensation. Eventually  I went over the threshold into this extremely blissful state, with my whole body participating in the sensory experience. It’s hard to describe, but oh so wonderful.

Mistress prefers me to have these “girlgasms” because I don’t get all cranky and grumpy afterwards. Right after, all I want to do is get close to her — even cuddling right next to her doesn’t feel close enough. I just crave feeling her next to me. The next few days I’m extra attentive and loving to her, so appreciative and present. I think we both prefer it this way.

And this works out pretty well with the whole sex-change business. I’m feeling impatient lately. I want to get on with this Becoming a Woman thing. I mentally put myself in that role walking around work every day. Even though am not ready to approach them yet to discuss it, part of me is so ready to come out — all the way out.

Over a dozen friends now know. And in about a month I will be coming out to my “church” community, fully transitioning there so that I can dress as my new female self every Sunday at services and during my other involvements there.

I literally have a closet full of clothes now. Probably enough presentable and normal female clothing for 1-2 weeks at work. I need more shoes though (what girl doesn’t?!). And Mistress has decided that I’ll be having a second pair of ear piercings so I can wear 4 earrings at a time (like her).

Friday I’ll be talking with my gender therapist about next steps to start hormones. We’ll also go over a rough timeline. Bring it on! Let’s get this thing rolling, I’m feeling so ready to make more progress.

Now with more security

Mistress went to visit some relatives late last week. She took the emergency keys to our biometric safe with her. The keys to my chastity cage are in that safe, which opens only by her fingerprint. The safe is cabled securely in our closet.

Until now she had “hidden” those emergency keys in our house. She teased me at times to try to find them, but I dared not look as I didn’t wanted to be tempted to let myself out of chastity. The corporal punishment consequences for that would not be good, and I couldn’t live with the guilt. So it’s actually good that those keys are gone and locked in her relative’s gun safe over an hour away.

We still have a spare set of chastity keys in a tamper-proof box. But the security of my chastity significantly increased by her decision to relocate the keys to our safe.

Before she left she teased me pretty significantly. She reminded me about how why I was locked up: because tiny (her name for my cock) is so small and inadequate for her needs. She said she might find another guy to have sex with while she was away. Some stud with a man-sized cock that could really please her. And she asked me what I thought about that. I said “I want you to be happy, even if that’s what it takes” and I meant it.

In the end she was too busy with the relatives to do anything else — or so she tells me. I expect that’s true, since her finally cuckolding me for real would be a new level of humiliation that I’m quite sure she would want me to experience.

I’m continuing to come out to more friends about my plans to transition into a woman. Mistress is supportive, in fact we told her sister today. I’m hoping to start hormones this month, and am continuing to work with professionals on moving forward. Some days I’m scared about how fast things are moving, other days I’m frustrated that we’re not further along in this (roughly) 2 year process.

Mistress and I went out to a pretty busy restaurant this weekend, and I was dressed up pretty. She went with a rather butch look (jeans, jean vest) while I had on a nice dress with hose and matching low wedge shoes. I seemed to completely pass as a woman, which is great.

Lately I’ve had an issue with the chastity cage when crossdressing. Since the cage is bulky I have to really tuck it between my legs. Twice now one testicle has slipped through and escaped between the base ring and the base of the cage. That’s my own fault, of course, for ordering a base ring 2 sizes larger than I wore on my CB-3000 (which I’ve previously blogged about at length).

The last time it happened I requested the keys to get that testicle back into place. This time I worked pretty hard to push that naughty ball back through that narrow space. Nasty! I think I bruised it. Weird how I can not even notice it slipping out. Yet getting it back through is torture. Ah, what we go through to look beautiful!

For those curious about transsexuality, I’ll again recommend the book She’s Not There – A Life in Two Genders. I finished it, and it was very, very good. Hard for me to read in spots, as it got so personal. But very education, very readable, real, and well written.

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