Healing, slowly

I haven’t written any updates lately because there’s been little to write about. Most of my activities with my wife and Mistress have been curtailed due to issues with post-surgical healing. But things are looking up.

My first 6-7 weeks post-op went quite well. Minimal pain, considering that this was major surgery. But then things started to hurt, and hurt more. For various reasons I wasn’t able to get the medical attention I needed until last week. And even then things aren’t 100% resolved yet.

So, unfortunately, The Drawer still remains unused for it’s intended purpose. Mistress has talked about it recently, though. I’m hoping to post a few pictures of the D-rings that I mounted in The Drawer for eventual restraining uses.

I specifically asked my doctor about resuming anal sex, and she was fine with it. Since then, Mistress has made it clear that she intends to go there sometime soon. Not sure what she has in mind, stay tuned.

And for more updates about how my Gender Confirmation Surgery is really going, see my other blog “Blooming Time”.

Not just any dildo

Mistress took the brand new, very realistic cock shaped dildo and held it to my face. “Kiss it,” she commanded. I did. “Open,” she said, and I obediently opened my mouth. She slid it past my lips, sensuously working it slowly in and out.

“You like that, don’t you?” She kept going as I tried to respond, my words came out all garbled due to the intruder. Then she briefly stopped and allowed me to speak. “Yes, Mistress,” I said with complete honesty. “Of course you do,” she shot back, “because you’re a little slut whore who loves to suck cock, isn’t that right?” This time she didn’t permit a response as the dildo went deeper and faster, down my throat as I choked on the deeper thrusts. She laughed and continued for a while, amused, as tears started running down my cheeks from gagging.

Fast forward a few days…

We met a kinky couple we know for dinner. Afterwards we gave them a present. She opened the box to reveal a dildo, very similar to the one that recently raped my mouth. But this one is a little better and has a handle for, well, “ease of use”. Her husband rolls his eyes and says “well isn’t that special”. Our friend is delighted because she recognizes what it really is.

It’s a replica of my own cock – the penis I won’t have anymore in about 16 months.

Mistress ordered kits to create dildos of tiny (her name for my cock). Yes, they make kits that you can use at home (like this one, which I can highly recommend) – handle not included (that was my idea).

So now Mistress can gag me and fuck me with “my own cock”, as she calls it. And one of our friends can pleasure herself with a near-exact replica of my penis. Eventually Mistress wants me to be fucked in my new vagina by some man of her choosing while my own cock invades my ass.

Despite Mistress telling me some great fantasy stories while making the penis castings, tiny wasn’t at his largest. And that’s somewhat humiliating. Then again, I’ve been on estrogen for about 3 weeks now. And the way the mold cures, I think gravity can’t help but shrink them a little. But perhaps I’m trying to compensate.

One story Mistress told me was how transsexual women are a lot more likely to be raped by men (a statistic she made up just to tweak me). And, she said, since I’m such a slut it’s likely to happen to me before too long. (Can you tell she knows that I have fantasies about being raped?) She talked in detail about what these two men would do to me, which greatly turned me on as the molding material set around tiny.

Yesterday she had me place an additional order for the silicone components. We’re going to use our best cast one more time. This time it will be a “chocolate colored” version of my cock. She said this will make it easy to tell which one she will use over and over in my ass, and which one will get used in my mouth and eventual pussy.

The last time she allowed me to have a boy orgasm, she rolled our “dildo of tiny” in my fresh cum and then made me suck and lick it off the dildo. It was the first time she had ever made me eat my own ejaculate. I was a bit shocked that she just did it, but I’ve turned it all over to her, and that’s that.

Over the last few weeks she’s allowed me just that one orgasm. Meanwhile she directs me to eat her, teaching me more lesbian techniques as we go. Last night she was very pleased with my progress as she had two orgasms making use of my lips and tongue.

We now personally know several other male-to-female transsexuals, and two of them are having their final sexual reassignment surgeries over the couple of months. I’ve been thinking about the finality of that lately. The penis is converted into a vagina and clitoris, the scrotum into labia. It’s a one-way trip. And so far I’m on track for my own date under the scalpel in late 2013.

I guess at least we’ll have a few things by which to remember tiny.

No Fooling

Last night Mistress had me begging and pleading while she just laughed.

We were in bed watching between South Park episodes on DVD, and she just looked so sexy and wonderful. I started caressing her and getting turned on by her beautiful breasts and soft, warm thighs. I told her I loved her and wanted her so much.

She started teasing my nipples, which is like pouring gas on the fire of my horniness. Tiny (her name for my cock) filled his metal chastity cage and was straining against the tight bars. I could not help myself and started begging, I wanted her so very badly.

“Please, please Mistress, I want to make love to you, please!?” She just laughed and kept stimulating my nipples. “I want so much to feel you again. It’s been months since you’ve allowed me inside you. Please?!” Although I am not to ask for release or sex, she seemed willing to play along and I desperately wanted it.

“Months?” she asked. “It hasn’t been that long, has it?” I said “Four months, not since Thanksgiving.” I didn’t realize it at the time, but she did let me inside her once since then. She said “Oh, I don’t think it’s been that long. Besides, tiny couldn’t possibly satisfy me anyway.”

“Please, Mistress, let me try. I want you so much, you are so sexy and beautiful. Please let me make love to you.” She laughed again and pushed me back, then put her feet on my chest and teased my nipples with her toes. “There would be nothing in it for me. Tiny is so worthless, and I wouldn’t get any pleasure. Look at how small and pathetic he is. The last time we let him out he was definitely smaller. Clearly he’s shrinking, if that’s even possible.” I said “yes, Ma’am.”

She continued “So, I don’t see any reason at all to let you out. The truth is that it would be nice to have a real man’s cock inside me right now. A big, firm, nice stud to fuck me properly.” I lowered my head and replied “Yes, Ma’am, you deserve a quality penis to pleasure you. I want you to be happy.” She sighed, “Well, we don’t have one, do we? Just your useless bump of flesh. But hey, if you want to try, go ahead.”

She spread her legs and pulled her labia lips apart. I looked at her. “Let’s see what you can do” she teased. I moved between her thighs and placed the end of the chastity cage between her pussy lips. I gently moved it around, but I couldn’t feel anything. The cage was right up against her wonderful sex, but no sensations for me at all. “There, isn’t that nice?” she said, mocking my attempt.

I leaned forward into sort of a missionary position, my caged cock still up against her opening. It was unbelievably frustrating to feel all the feelings of intercourse except any sensation on my penis. My legs against her thighs, her upper body under mine and next to my arms, kissing her desperately. She laughed in my face. “Are you enjoying this?” she taunted. I was nearly crying. I whined that I couldn’t feel anything.

She laughed again and said “Well, I actually am really enjoying this. I can tell that you are really suffering, and I am loving that.” I meekly agreed, and told her that I was glad she was amused by it. “More than amused,” she said, giggling, “this is not only making me horny, but it’s a lot of fun too.” She went back to stimulating my nipples as I pointlessly thrashed around between her legs, trying to be careful not to bump her sensitive places with the bulky metal cage, but also dying to feel even the smallest sensation of her pussy on my cock.

Nothing. She smiled and kept going, tormenting me relentlessly. The head of my cock, when fully swollen, does protrude a bit between the bars of the chastity cage. But I get no sensation from it, probably because the skin is so tight and there is so little actual contact. So even through the cage provides some skin contact, for me it may as well be solid since I can’t get any stimulation through it.

I begged and pleaded some more, and she said “I let you have an orgasm not that long ago, remember?” Dejectedly I answered “Yes”. She said “And do you remember how poor your attitude was after that?” I couldn’t deny that. “So why in the world would I want to do that again?” she asked. “You shouldn’t, Mistress, I’m sorry. You shouldn’t allow me any more orgasms, ever.” I couldn’t believe I said that, but I did. She said “You’re right, I shouldn’t.” Ok, that was dumb, but I was still really horny.

I caressed her thigh, and she played with my nipple more. Then she pulled her labia open again to display her waiting and wet vagina. I have never been more sexually frustrated in my entire life. She kept teasing and laughing while I begged and moaned and cried. Eventually she stopped and said that it was time for me to calm down. “We need to get something up your ass. Why don’t you go for a pony ride?”

Although it sounded like a question, it wasn’t. She directed me to put the big black dildo on her riding machine. I realize that different people mean different things when they say “big”. So here’s a picture of it.

Big and black

Big and black

It had been a while, and even with lots of lube it still took some time for me to accommodate the “pony’s big black cock” in my ass. Once it was fully inside, she directed the riding speed. The pony started slow and sped up as she told me to adjust the speed. She stayed reclined on the bed, reading a book, while her pony fucked the daylight out of me.

She told me to stop, and that the pony had cum inside me, and that I should thank the pony. It was humiliating to thank her riding machine for raping my ass, but she is the Mistress and keyholder. It took about 5 minutes for me to settle down enough to dismount. It’s always sort of a sad, empty feeling when that massive dildo pulls out of my well-stretched ass. I cleaned up and joined her again in bed.

She wanted a backrub to get to sleep, which I lovingly provided. Soon she was in dreamland. My cock was still straining the cage, remembering in vivid detail when it was next to her sweet pussy. With sore balls I rolled over and tried to get to sleep.

The next day we were hugging in the kitchen and I was overcome again with desire for her. I kissed her passionately and held her, grinding my caged dick against her thigh. Again I begged to be able to make love to her. She just sighed. I pulled down my pants and humped some more, while she laughed at me. I felt her hands around the cage, just barely getting the smallest bit of sensation of the parts of tiny that were poking out between the metal bars.

“If you can find the keys, you can have me” she teased. “But the keys are locked in the safe!” I said. “Not those…” she replied. It took me a minute to understand what she meant. There is a set of backup keys that can open the safe. “But I don’t know where they are!” I cried. “No, but maybe you can find them. Maybe they’re right under your nose!” I knew she was teasing me, likely trying to get me to tear around the house half naked and crazed about sex looking for those keys.

I just couldn’t do it, feeling like there was no way I would find them. “I’ll never find them,” I cried. She just said “Oh well” and lightly patted my bare ass. I pulled my pants back up and tried to settle down by doing the dishes.

By the way, I have no April Fools stuff in my post today.  As with all my non-fiction postings, it’s all true.

Mistress just told me that tonight she plans to tie my wrists and ankles out tightly on our bed and then stimulate my nipples. She’s wants to see if I can have an orgasm (a male or female orgasm) that way. That would be nice, but I suspect it will instead be a long torment session that she enjoys much more than I do.

Two to One

Mistress woke me up this morning to use me to pleasure her to two orgasms. We were still in bed.

She started by arousing me. That turns her on, since we both know that I can’t orgasm or even have an erection being locked up as I am. She loves to torment me and watch me crave and beg for relief, knowing that the keys are in her sole control.

Once she had my attention, she sat her sexy naked body on my chest, then moved her crotch to be directly in my face. She grabbed my hair and pulled my face against her pussy. I didn’t need any further instructions, and began licking her clit.

She moved down a bit further so I could apply more pressure. Then she instructed me to bend my knees so my legs formed an incline for her to rest on. I continued lapping at her sex, and soon she had her first orgasm. I gently caressed her while she relaxed in her happy space.

She moved closer again, and my tongue found it’s way inside her. She started rotating her hand slowly on her sensitive nub while I orally penetrated her. I felt so happy to be pleasuring her. It didn’t take long for her second orgasm to wash over her. Then she rolled off, crawled back under the blankets, and instructed me to cuddle with her.

I thanked her for the opportunity to serve her. She just stroked my hair. I held her and let her enjoy her time of post-orgasmic bliss.

For my Saturday chores, Mistress let me wear my formal housekeeping dress instead of my everyday housekeeping dress. The formal one is black instead of light grey. And it looks best with black hose and black heels, instead of the white tights and white work shoes I normally wear. She complimented me on how nice the kitchen floor looked after I swept and hand-washed it on my hands and knees. I did lots of other chores too.

While changing for an evening event, she came up behind me and leaned me over the end of our bed. She played with my nipples, which arouses me intensely. I was only in my panties, and she was grinding her crotch against my ass pretending to fuck me. She kept stimulating me and I was moaning.

To my surprise she retrieved a dildo, slid a condom on it, lubed it up, and slid it inside me. Then she returned to playing with my nipples while she penetrated my behind. Again I was whining and moaning, craving release. Then she presented an even bigger surprise. She retrieved the keys to my chastity cage from the safe and tossed them on the bed.

“You’ve been such a good girl lately, I think I’ll allow tiny to squirt just once.” I wasted no time in removing the PA-lock and cage. My partial erection from all the stimulation made it difficult to pull the cage off my cock. Of course I managed. Then she was behind me sliding the dildo in and out while flicking one of my nipples with her other hand. I steadied myself with one hand and jerked off with the other, spraying a large amount of cum.

My orgasm was intense and wonderful, but it really struck me how brief it was. My legs were wobbly afterwards. I was really aware that the build-up and physical release was fleeting, and then it was gone and I was off cleaning up and putting things away. While I really enjoy those moments of pleasure, I somewhat regret how quickly they pass. My wife seems to enjoy much more time of post-orgasmic bliss.

Although she had two orgasms today and I had one, she’s had a total of five during this latest lockup.  Combining this with my last round, she’s had 11 orgasms to my 2 over the last 4.5 weeks.

A couple hours later Mistress interpreted something I said as harsh and snippy. “I can sure tell that you had an orgasm.” I politely disagreed, but she wouldn’t have it. “With an attitude like that, I’m not sure I’ll ever let you have another orgasm.” I stopped disagreeing.

So, my next period of chastity begins. I hope she will use me for her pleasure again soon. If I cannot orgasm, I at least want her to be happy.

Party Pounding

Mistress has been teaching me how to make love to her like a lesbian. Obviously that doesn’t include any participation by tiny (her name for my locked-up cock).

She’s had several orgasms now over the past 11 days that I’ve been in chastity. The combination of being totally denied genital stimulation and starting this transgender journey in earnest leaves me ignoring my “male parts” day-to-day. Other than washing around the cage and applying some lube, I don’t tend to think “with my little head” at all anymore.

My poll shows that a clear majority of readers of this blog don’t mind my including details of my gender transition story here, even though my intention for this blog was to be focused on chastity. By a 4-to-1 clear majority, most voters (35 = 81%) agreed with “I don’t mind chastity and TS/TG stuff in your posts; let it all hang out, dude”. The rest selected “I strongly wish you’d focus just on chastity in this blog”.

I’ll try to maintain as high a level of chastity focus here as I can. But I do concede that my gender issues are coming to the forefront of my life. I’ve started laser treatments to eliminate the dark hairs on my face. And in 2 weeks I’m being assessed for a Gender Transition program. I’m hoping to start female hormones as soon as I can.

My Mistress/wife/keyholder is totally supportive, which is incredible. We went shopping together for shoes today, with me crossdressed. It went just fine. We’ve told a few close friends, but are being cautious at this point.

In a few years, if things go well, I could complete my transition to being a female. For real. This has been an issue in my life for decades, so it’s really quite amazing to finally get to a point like this where I can foresee actualizing this part of me. And to (likely) be able to keep my marriage is rare and incredible on top of all that.

While this isn’t part of my interest in going M2F, it occurs to me that not having a penis is sort of like the ultimate chastity situation. I’ll never have a male orgasm, ever again. It’s possible that the “bottom surgery” could leave me unable to orgasm at all (but most do end up with a functional clitoris).

Last weekend Mistress and I attended a big kinky play party locally. I wore a new dress and shoes, and really looked hot! I got lots of compliments. Mistress had a new outfit too and she looked great as well (I think she was a bit jealous, actually).

At the party she had me show my chastity cage and the useless tiny inside to friends. They were impressed with the seriousness of the cage.

Later she used me for a scene. She strapped on our largest dildo and, with me on my knees, had me sucking it and gagging on it as others watched. Then she had me strip, get up on a massage table, and she fucked me hard with it.

As she was impaling my ass, she talked about the people watching, how they were laughing at how small my cock was and that it was locked up. I actually did hear people laughing. She teased that she didn’t think to bring the keys, so I shouldn’t expect any release. I felt very close to having an orgasm with her just fucking me. It was really strange.

More later. I must not daly, Mistress is waiting for me in bed upstairs.

Teased into Pain

I suffered through a very intense tease-fest last night.

My wife and I went to bed, and she wanted to “see tiny” which now means “show me your chastity cage”. I presented myself to her, and we were both surprised how small my cock was in the cage. I’ve been wearing it for 6 days now, and I inspect it frequently. This was the first time I’d seen myself shriveled as opposed to merely flaccid.

My penis was narrow enough to be loose within the cage. Until then I’d always been large enough so that my shaft was snug against the inside of the cage bars. But now it looked as if the cage was way too big. The humiliation aroused me, and before long tiny was pressing up against the bars again.

My wife tried to masturbate me through the cage. She asked me if I could cum that way, and I said no. I just can’t get enough stimulation, as the bars only allow contact with a fraction of my glans. She gave me permission to orgasm, but neither her hand nor mine could complete that job. The attempts, however, got me very horny and amused her.

My wife teased my cock and my nipples for quite a while. This was the most arousal I’ve had since putting on the JailBird. The base ring felt a bit small as my genitals swell up to the maximum size permitted by the stainless steel entrapment. It was somewhat painful (I’m thinking I may need a larger base ring). My wife was really enjoying the look of my cock severely compressed in the cage, with bits of flesh poking out between the bars.

I was so sexually frustrated I was moaning and to the point of crying many times. I was instinctively yet uselessly humping the air and begging to have sex with her. She just laughed and said “No, I don’t think so”. She compared my antics to the humping that dogs sometimes do when they get randy.

She also reminded me of how she couldn’t be satisfied by my cock anyway, reinforcing how small it was. “You probably couldn’t even get hard enough to fuck me. The longer tiny is locked up, the more he atrophies and the more useless he becomes. Eventually it’ll be just a worthless lump of flesh. And tiny is just too small to be worthy of going inside me anyway.”

Then she brought up the black man she’s contacted, and started raving about his long, thick, impressive black cock. “Now that’s a cock that could satisfy me” she said. “Did you see how muscular and strong he is? I bet he could overpower you and rape you. You’d like that too, wouldn’t you? Having him force that massive cock of his inside you?” It was true, so I could only concur.

She put her hand between her legs and wet her fingers from her sex. Then she put her fingers under my nose. The smell of her juices drives me wild, and I bucked my hips in a frenzy. She repeated this olfactory stimulation about a dozen times. “I imagine it would feel sooooo good to have his cock inside my wet, warm pussy. Maybe I’ll let him fuck me, and make you watch.” I was too sexually crazed to even respond, and her words turned me on even more.

Eventually she tired of the game, and got comfortable in preparation for sleep. It took me about 20 minutes to calm down. During that time I asked her about her recent dreams and fantasies, something she teased me about by text message earlier in the day. She said “Well, one is about castration.” I asked if she would care to elaborate. She said she was tired, maybe another time.

With that she got comfortable and was soon asleep. My crotch was sore from the tightness of the chastity cage, and it was a relief when I finally became flaccid again.

It’s been almost two months now since she’s allowed me to have intercourse with her. And since the cage arrived on Friday I’ve had no release. She said she wants to remove it soon to check for any physical concerns. I’m confident there won’t be any, so I’m quite sure she’ll want it right back on.

It looks like the PA lock will be here tomorrow. Installing that will be quite a momentous occasion.


Last night I spent some time with some guy friends. We meet about once a month. This was my first time wearing the JailBird chastity device with this group. Of course they have no idea that I’m submissive or in chastity.

But I do. While sitting there chatting I realized that they all get to masturbate. I don’t. They all get to have sex with their beautiful wives. I’m denied intercourse. They can use urinals. Not me. I’m sure I was the only one in the group wearing women’s panties. Humiliating. Embarassing. All in my head.

I’m certainly getting used to it. But sometimes it just strikes me how different I am. In general I like diversity. But the occasional reinforcement of my enforced and denied sexuality sometimes surprises me. Out of the blue I am reminded of my submission and genital inadequacy.

A few evenings ago at home I lifted the skirt I was wearing to let my wife inspect the cage. Tiny (her name for my cock) was so small that there was room left in the cage. My wife remarked how minuscule my cock was, and there was no denying it. Even though the cage is only 2.75 inches long, my cock was shorter than that.

She surprised me yesterday by telling me about someone she is in contact with online. She excitedly described him as a strong, muscular black man that only lives a few miles from us. And she said he had an incredible cock which was long and quite impressive. Her text message to me earlier at worked teased about him being “hung like a horse” and that he was looking for a couple into power exchange. She is quite eager to show me pictures of him. I got home late last night, and she was already asleep in bed.

This morning she mentioned him again. It sounded like she might be planning to invite him over sometime soon. I said that sounded like it would be fun for her. She clarified that she was planning on it being fun for me. I stopped, and she observed my reaction. “Why are you blushing?” she asked. “Look at you! Are you getting hard?” she asked rhetorically.

I’d assumed she’d be interested in him and his cock for herself. But I realized that’s not at all what she’s thinking about. She likely plans to offer me for his pleasure. It suddenly shifted and made sense. My wife loves to orchestrate. It’s often more fun and erotic for her to set up a scene and manage it, rather than participate directly. It’s like she’s directing her own little movie. Except it’s real.

I can’t let myself think about it too much. Partly because I want to let go and let her be in charge, avoiding any expectations in my own mind. But also it’s an erotic fantasy for me, and the strain of tiny against the cage can be uncomfortable. She very well might make something happen later this week or weekend.

This would be significant as the first time either of us would be sexual with someone else at our house. My wife has arranged a few gatherings where our guests enjoyed some sexual activity. Like the time she arranged for this guy to experience cunnilingus for the first time with another woman we know well – right there on our living room couch. My wife likes to make things happen.

She mentioned to me that she’s had a lot of sexually-oriented dreams lately. I asked her about it and she clarified it as “dreams and fantasies“. I told her I’d like to hear more, and she said she’d “tell me a story later”. Some of her stories are not that far from reality for us. So I’m quite intrigued to hear her tale.

She also mentioned how much she likes being able to tease me at work by sending texts. She askes often about how tiny is doing. I guess it’s a way for her to reinforce the situation, maybe make me horny so I suffer a little in the cage, and put some spice into my workday. She’s wonderful.

After work tonight she suggested I put on my housekeeping dress and take care of the dishes after dinner. Of course I did so. Midway through the dishes she called out “Teena! Come here.” I joined her in her office, and on her computer was the profile (and pictures) of the black man I wrote about above. She read me his profile, and then said she was going to contact him. As I left, she was typing that message. She is serious. A short while later she returned to the kitchen and asked me if I would like to have his huge black cock up my ass. “Yes, Ma’am” was the reply.

His profile talked about both dominant and submissive roles. She mentioned that he offers foot massage, which is something my wife really enjoys. So she has several reasons for inviting this man into our home. His muscles are really impressive – bodybuilder stuff. I am a total wimp compared to his physical condition. It’s a bit frightening.

Once again – be careful what you wish for?

P.S. Bonus link: Keverly and frannie – I really enjoyed reading this story today.

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