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…


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.

Cooked Bool Tincture

I wrote Mistress yesterday, confessing a concern/desire I’ve been thinking about:  CBT.

Potentially I won’t even have my cock and balls in as few as 15 month (after surgery to become a female). And as a male submissive, CBT is a pretty typical thing to experience. I realized that I haven’t experienced much along those lines though. And time is, literally, running out.

So I wrote Mistress an email about this, how I felt, and that I wanted to simply leave the issue in her hands. What she does when, if anything, how intense, etc, is all (of course) completely up to her.

Well, this weekend is one of our BDSM play parties. She told me today she’s already talked with a friend to help her with a scene she has planned for me. This friend is very much into pain herself, and is well versed in kinky things of all kinds. I’m a bit frightened to consider that I might just get what I’ve asked for.

Then again, Mistress may have something entirely different in mind. I won’t know. One thing I do know that she has planned is for me to come out as a transsexual to our friends at the party. I’m not worried about that at all, there are lots of transgendered folks in our kink community.

I only asked for one thing specifically: a butterfly board experience. The link is not for the squeamish. Of course if/when that happens is up to her.

We’ll see what she has in mind for me tomorrow night…

To Be Forced

Mistress spontaneously jumped me in our bedroom this afternoon.

I got home from work and was changing out of my “boy clothes”. She was dressed, I was naked (except for my chastity cage and some jewelry).

She forced herself between my thighs, and hoisted my legs up and apart with her strong arms. I instantly went into submissive mode. She got that dominating grin on her face, and I knew she was enjoying herself.

She started playing with my nipples and guiding me through our new routine, where I can experience an orgasm with no genital contact. I focus on my breathing, letting the erotic stimulation flow through me in a new way.

She started grinding her pelvis against mine, and whispered to me about how it’s not going to be long before tiny (her name for my cock) will be gone and she’ll have my slutty cunt to fuck instead. OMG, that was so hot to hear.

“I can’t wait to put on my strapon, or the feeldoe, and rape you”, she said forcefully. I wished that she could do it right then and there. My heels dug into her backside nearly involuntarily, and my legs pulled her against me with her rhythm as she pretended to penetrate and pound my imaginary pussy.

In those moments my body craves — utterly craves — to be entirely female right then and there. Not as a fantasy — it’s almost like some strange body memory. (And no, I have no sexual abuse memories). It’s more like my body wants to get where it’s always desired to be. In reality. Now.

Mistress then began to bite me. This turns her on, she loves to feel her teeth digging deep into my flesh. She continues stimulating me and biting, the pleasure and pain mix and blend as I swirl in the bliss of her intense attention. It’s incredible, painful, wonderful, amazing.

Then I’m over the edge. We call it an orgasm because the erotic feelings peak and my whole body shudders. I’m flooded with emotions, and sometimes cry. It goes on for at least a solid minute. It’s a more intense, whole body release compared to my “male orgasms”. And then I just want to be held and be close to Mistress. I can’t get close enough to her, it’s like I want to crawl inside her. I need to feel her right next to me, to hold her, to feel her touch. Sometimes I cry again.

It takes some time for me to come down. We talk and process it. She talks of feeling satisfied with her domination of me. I offer to pleasure her and she declines. I admit to feeling guilty about receiving such pleasure without her having any sexual pleasure, but she will not hear of it. Her “dom energy” had a wonderful outlet, she insists, and she is satisfied. I can’t argue or ask for anything better. I feel so grateful, so lucky, so happy. We hold each other quietly in bliss.

She inspects me and seems pleased with the marks she has left on my body. Visible bite marks, some will bruise by tomorrow. We both like it when she leaves marks on me that last a while.

Yesterday was one month since my last orgasm. I don’t think it’s even crossed her mind or mine for weeks. She will tease me about tiny, frequently. But her actions make it clear she has little actual use for my cock anymore. Just as well. I am happy enough submitting to her as she wishes, for her pleasure, at her will.


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.

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.

Delayed Gratification

This post isn’t about orgasms, it’s about punishment. And it’s not that I enjoy punishment, it’s that Mistress enjoys punishing me.

A few days ago she caught me eating dinner from a regular bowl, not my dog dish (which she lovingly calls my “trough”). I honestly forgot, but this is like the third time in a few months. And she’s tired of me “forgetting” Her Rules.

Instead of our usual red leather paddle, she had out three other severe spanking implements. One is essentially a hardwood board with a rubber tire tread on one side. That packs a wallop. Things proceeded as at other times.

As she started the spanking she told me to explain what I had done wrong. In detail. And to clarify why it was wrong, and how she can be sure it won’t happen again. By this time my ass is quite pink and hurting.

She continues, though, explaining why this incident upsets her. And she talks about how she doesn’t see how she can be sure that I’ll remember next time. All the while she is wailing away on my now painful behind with the big paddle or the wooden hairbrush or the strop. I’m now yelling into the mattress hoping the neighbors don’t hear.

The intensity increases as she proceeds. She explains that she wants to see some bruises this time, and wants to be sure that when I sit tomorrow (as I do all day at work) I remember.

When she decides that’s enough (about 20 minutes later), she rubs some icy-hot type “ointment” (as she calls it) on my red and painful ass. This time she told me to go stand in a corner with my nose against the wall while she watched TV. She left me there another 15 minutes while the cream burned my behind. She turned the volume up to “drown out my whimpering”.

After I came home from work she asked how my behind was. I said “fine”, since that was the truth. And the frown she showed made clear her disappointment. Next time it will be even harder.

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.