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.

44 Days and Counting

Mistress continues to leave me locked up with no sign of release. It’s been 44 days now since my last orgasm, one of the longest times I have gone without. She still shows no interest in my genitals at all.

I’ve been wondering if I might wake up some morning to a mess (nocturnal emission), but I haven’t yet. I haven’t had to put up with a lot of tease and denial, so it could be that I don’t have much fluid built up.

I have been wondering if I should try to milk myself again. I’ve tried a few times with little or no success. I even have an Aneros prostrate massager, but even that hasn’t been effective.

Things have been a little more stressed in our relationship. The gender transition thing is taking some toll, both as a near-constant source of attention and focus, and as an emotional drain particularly for her. Tonight I got all stressed out because I didn’t have what I needed to wear under the dress I had been looking forward to wearing out with friends tonight. It sure is different for me to care so much about how I look when I go out. Guys really do have it easy.

In four days I’ll be getting evaluated for starting female hormones. Mistress talks about looking forward to my breast growth, particularly how much my chest will hurt as it happens. She wants to poke and pinch and squeeze them to give me even more pain. I expect she will really like to bite them as well.

She also talks about how the hormones will work to make tiny (her name for my cock) even more worthless (“If that’s even possible”, as she says). They will make my testicles shrink and reduce or eliminate my male sex drive. She teases me regularly about how it won’t make much difference to her, since my “useless excuse for a cock never did much for [her] anyway”).

Yesterday her sister was over at our house. She brought her two little dogs. I came into the kitchen and saw my dog dish on the floor with dog food in it for her sister’s dogs. The same pink dog dish I have my breakfast in. Her sister didn’t know, but Mistress did. She saw that I noticed and she smiled that knowing smile that says “oh yes, I know this is humiliating for you – too bad!”.

My last male orgasm, over a month ago now, wasn’t that great so I haven’t feel very compelled towards another. Especially since the “female orgasms” that Mistress lets me have now and then are so much nicer.

I wonder how long Mistress will keep me locked up. We don’t talk about it, so I have no idea what her goals or plans are – if any. Perhaps she just considers tiny “locked away for good”. I’ve forgotten what an erection feels like. The sensation of stroking my hand against my cock is just a distant memory now.

Yellow and black

Mistress has been using me more and more to relieve herself at night. As I wrote a few weeks ago here, we have a new toy to help her easily urinate into my mouth.

Lately it’s been several times per week that she will “save herself a trip to the bathroom”. She will hop out of bed, come over to my side, and I will move my head to be just off the bed.  She puts one end of the soft funnel gently over pussy, and the other end in my open mouth. Then she pees while I swallow.

When she’s done she lets me lick her briefly (in place of using toilet paper or tissue). Then she crawls contentedly back into bed with a nice empty bladder.

Sometimes she lets me know she appreciates my service to her by saying to me afterwards: “Thank you, toilet.” It’s a sign of my submissiveness and servitude that I feel happy to hear that.

My routine afterwards is to first “flush”, which is to rinse the funnel with some water (always in a bottle next to the funnel) – swallowing it of course. That keeps it clean and ready for her next use. I wash it weekly.

I also rinse my mouth with some mouthwash, also nearby and handy. Mistress doesn’t like me to have a yucky mouth or “pee breath” in case we talk or she wants me to service her or even to kiss me.

Another real life event: We were having some ice cream, sitting on a bench outside at a shopping area. We were talking and she noticed this muscular black man nearby. The conversation stopped as she focused her attention on him, saying things like “yeah” and “Mmmmm”.

Then she turned to me and said “Look at his arms”. I did. His skin was beautifully dark, and he clearly worked out a lot. His biceps and triceps were well defined. He could easily kick my ass. I said to Mistress “He has very nice arms. I bet you’d like to feel them around you.” She scoffed, and immediately replied “It’s not his arms I want to feel,” and she went back to watching him.

Eventually she returned our attention to us, after letting out a contented sigh. Clearly she was enjoying a nice little fantasy in her head featuring this dark, handsome stranger.

I know part of why she likes to do this is to humiliate me. But I honestly don’t know how far she would go with it. I wonder if someday she will take it further, maybe openly flirt with other men in front of me. Actually, it will probably be a lot easier for her to do that now that I’m looking like a woman more and more with her in public.

We’ve also talked about how my sex-change situation might affect our sexuality and relationship. She has fears about me wanting a heterosexual relationship after I’m fully transitioned (and physically a female). I don’t see that happening, I have never liked cuddling or hugging or kissing guys. I’m only attracted to women.

However, she has talked about not knowing where her own sexual interests might go once I no longer have a penis. Being bisexual, she is very interested in lesbian sex with me, and we have explored some of that already. But she has wondered out loud with me if she might crave intercourse sometimes. Of course I support her in getting all her sexual needs met.

Which brings me to this question:  Would I be a cuckold if she had sex with other men after I become a woman? Legally I’m still her husband. But legally I will also be a female.  And we will undeniably have a lesbian relationship. What a twisted web we weave…

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.

Teasefest

Mistress and I entertained her sister today. It was the first time I was dressed in my female role in front of a family member. It went very well.

We were eating a late lunch out on our deck, and the two of them were talking about men and relationships. Somehow the conversation turned to black men, and Mistress made me quite embarrassed. She told her sister about the man adjacent to her workplace, how attractive he is and what a nice sexual partner he would make. He’s the one she teases me about having sex with a lot (I’ve blogged about that many times before).

Her sister thought she was just lightly teasing me, so Mistress went further. She said “just because my spouse won’t be able to please me like a man, that doesn’t mean I won’t get any.” Her sister laughed like it was a joke, and Mistress just sat there with a smile. I blushed like I had too much makeup on. “After all,” Mistress clarified, “I’m not a lesbian, I’m bisexual.”

At another point in the conversation Mistress told her sister “Chastity isn’t so bad,” when talking about her sister not dating for a while. Of course that was a subtle dig at my locked up cock.

After her sister left, we stayed on the deck to chat. I found an inchworm and we watched it for a while. Mistress named it “tiny”, for obvious reasons. “Go, tiny, go!” she said as it slowly moved across the table. At one point I remarked that he was “straight up”, and her quick reply was “Well, I haven’t seen anything like that in quite some time.” I observed that it was by her choice, and she just smiled.

Mistress used me for her own orgasm this morning. I really enjoy being used like an object that she uses for her own pleasure. I mentioned to her that it turned me on. She said she didn’t notice, and that it doesn’t matter anyway. I love it that she’s right — that her sexual pleasure matters and mine doesn’t.

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