Lesbian cuckold?

I’ve been living full-time as a woman for almost 14 months now, and I’ve been on feminizing hormones for even longer. One thing that means is that I can’t have penetrative sex anymore. To be blunt, my cock just won’t get hard enough for me to screw someone. Like my wife.

She loves to use this to humiliate me. This hormonally-induced impotence gives her lots of fodder for teasing. She doesn’t miss any opportunity to riff on words like limp, shriveled, tiny, ineffective, useless, etc.

She will also talk about being with other men for sex. I always – and I mean always – blush when she does. It’s involuntary. She’s even made be blush like that in front of friends, and they all find it humorous. Early on it seemed like she would talk about it just to tease. I’m not so sure anymore.

Yesterday our conversation turned to sex, and she asked me if I would like it if she were to have sex with a guy. I reluctantly said that I would understand, and that I wouldn’t mind. I said I sincerely wanted her to be happy. She asked me very specifically if that was my “final answer”. I said yes.

Tonight she told me she misses “man-sex”. I apologized for not being able to provide that for her any more. She said it didn’t matter, because she can get that whenever she wants, “Right?” I had to agree. After all, I honestly do want her to be fully sexually satisfied.

I know I can still satiate her sometimes. She lets me eat her out when she wants it. I never disappoint. But she says it’s not the same as a warm, firm penis inside her. I can’t dispute that.

I’ll be picking a surgeon this week for my Gender Conforming Surgery (which will convert my genitals from male to female). I think the finality of this is part of the energy that is going on.

I still can’t tell for sure if this “lesbian cuckolding” is something that she will go through with. More and more I am thinking that she will eventually. What’s unclear to me is whether she will get hers before or after she arranges for a man to take my newfound virginity. And I have no doubt at all that she will arrange that, if she hasn’t already.

 

Paving the way?

I’ll probably appear to be a bit fixated on this topic, but I wanted to share a conversation from last night while it’s still fresh in my mind.

My wife revisited the “jealousy” topic (see my prior post) after we went to bed. She wanted to talk about it more, in some detail. It surprised me.

She started out saying she wanted to be sure she understood how I thought I would feel if she were to have sex with another guy.  “So, you’re telling me you wouldn’t be jealous?” she asked.

“Well, like I said before, if it threatened our relationship, like if you wanted him instead of me as a life partner, then yes, I think it would be terribly hurtful for me. Not in a erotic humiliation sort of way, but in a severe depression and life sucks sort of way.” I continued, “But if it was just sex and not a deeper, emotional relationship, then… I don’t think I’d be jealous.”

She still seemed surprised. “I just don’t get that,” she said.

I asked her “Well, how would you feel if I had an affair?” Her response was immediate and firm. “Oh, that’s easy. I’d leave you immediately and we would get a divorce as soon as possible. I hope that’s clear. Is it?” I said “Yes, Ma’am, very clear. That will never happen.”

There is no doubt that this is a female-led relationship, that she is the dominant, and that I am her submissive.

“Let’s walk through a scenario,” she said. “You imagine it happening for real, and tell me how you feel.”

She continued. “You come home from work someday, and things look a bit messier than usual in the house, like maybe I’ve been distracted most of the day. You don’t find me downstairs, but hear something upstairs and come into our bedroom. There you see me naked on the bed with another man. We’re having sex, and the room smells like we’ve been doing it for hours. I don’t hear you, as I’m just about to orgasm again, and I do, making quite a bit of noise. Then I do notice you, and tell you to shut up and sit down. What do you do?”.

I said “I’d quietly sit down, without saying ‘Yes, Ma’am, right away’ as you’ve instructed, because you said to shut up.” She replied “Very good. And how would you feel?”

I pondered this, trying to put myself into this mythical situation. It was difficult to separate the idea of this really happening from a fantasy (one I’ve had many times). I answered her, “Well, I would feel surprised, shocked, and maybe a little hurt. But I’d also feel somewhat good that you were enjoying yourself so much, being sexually satisfied by him.”

Then she asked “How about if he was giving me oral sex? How would you feel about that?” That answer seemed easier: “I’d feel a little more hurt by that, since I really enjoy going down on you, and it’s something I can still do.” She didn’t miss the opportunity to rub it in, saying “Yes, I guess that is the one way you can still satisfy me sexually. We both know that, thanks to the hormones, tiny is more worthless than ever.”

She put her hand down my pajamas to check tiny’s status and said “This is turning you on, isn’t it?” I had to admit that it was (it always does). The answer to her question was obvious, but despite that, we both knew that there wasn’t enough there for me to sexually satisfy her. My size, thickness, and firmness has substantially decreased; a year of feminizing hormones will do that.

She rolled over onto her stomach, and put a hand down between her legs. She made a point of telling me “I’m going to masturbate now, thinking about having sex with a black guy I met at a swingers party before I met you. He had a magnificent cock. I gave him a bj back then. I might still have his email address. It might be time to reconnect. Mmmmm.” She started moaning and bucking her hips. I put my hand on her thigh to feel her gyrate until she came, relaxed, and got quiet.

It feels like I’ve just gone past that point — where those who want to be cuckolded suddenly realize that this might not be just a fantasy anymore, and that it’s truly out of their control. Maybe she’s just mindfucking me again. But what if she isn’t?

And yes, it really did happen like this last night.

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.

Bound and Beaten

The things I suspected my post yesterday came to pass last night. I came up to bed and my spouse/Mistress had our leather paddle quite obviously placed in the middle of the bed.

She had me lay face-down on the bed with my bare ass conveniently placed for her. As she watched TV she spanked me for about 1/2 hour. She interrogated me about recent behaviors that she didn’t like, and why I was acting like that. I gave her my answers, but in the end it came down to having been unlocked.

When she was done and my ass was red and sore, she applied the hot/cold cream as she does after my spankings, which burned more. Then she had me lock tiny (her name for my cock) back up in our cage.

She plans to visit relatives overnight later this week. They live 2 hours away, and she told me she plans to take the emergency safe keys with her. I suspect she may leave them there, far out of my reach (and likely locked in their gun safe from now on). Our bio-safe has been opening consistently well with my wife’s fingerprint, so not having the keys in our house would increase security. Mostly I think she just doesn’t want me hunting for them while she’s away.

I had gotten spoiled over the last week or so being unlocked. Using a urinal feels like a luxury that’s been taken away. And I’m back to wearing feminine pads in my panties to catch the drips after peeing.

This week I outed myself as a transsexual to 7 more people.  Four were folks in our kink community, two were friends, and one was a GLBT attorney that we’ve come to know. And this past week I had two hair removal treatments, one for my face and one for an arm. 5 weeks until my next treatments.

I’m hoping to move forward in May with getting on hormones. I’m anxious to see how quickly things might change. Then it’s time to start thinking seriously about when I will go full-time. That’s called the RLE (Real Life Experience), a time of living 24×7 as the new gender. That would require me “transitioning” at work, which involves some conversations with them about all this. Lots of details to deal with there. Some risk I could lose my job. I hope not.

Chastity leaves me so bulky between my legs. I have trouble looking female between my legs, and that’s frustrating. I am looking forward to the day when I don’t have male genitals anymore.

Mistress has informed me that she is horny and that I’m to orally service her tonight. She said she wishes she could strap my head between her thighs and keep me there all night, and piss on my head whenever she wanted. I told her I would do that for her. Time to go be her slave, which makes us both happy.

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.

Out of Mind

It has been two weeks since my last orgasm, and a week and a half in 24/7 chastity. I find it interesting to observe the mental and attitude changes happening to me.

One change is that being locked in the cage is baseline now. The cage is like a part of my body. Once or twice a day I’ll become aware of it, but for the most part I don’t even think about it. That excludes times when I’m feeling aroused, as the tight grip of the cage during an attempted erection really can’t be ignored.

So for two solid weeks now I haven’t been allowed to even get hard. My cock always curves downward, it is always less than 3 inches long, and it cannot achieve it’s full thickness. Although I can touch parts of tiny (my wife’s name for my cock) through the cage, I can’t access enough of my penis to even get close to an orgasm. But I do not even attempt that, since I am no longer allowed (by written agreement) to even try to stimulate myself sexually.

At times, my wife/Mistress/keyholder will amuse herself by sexually teasing me. Sometimes she flaunts her sexy naked body when changing clothes or showering. She likes to spread her pussy lips so I can see what she is purposely denying me. Sometimes she touches my body in those ways she knows drives me crazy with sexual desire. I know she loves to watch my intense frustration, and it makes her happy when she confirms how tightly the cage constricts my engorged genitals.

But there have been only a few of those teasing times these past two weeks. Mostly life goes on, and she is busy with many things. Me being her chaste, sissy hubby is just a standard part of our everyday life now. It’s not a big deal, it’s just the way it is. She doesn’t focus on it as frequently as when we started using the new cage. To her my cock is “out of sight and out of mind.”

I’m not complaining. That wouldn’t make sense, since I wanted to be in chastity. My point is that mentally I’m finding myself adapting to being basically sexless. For a male with an average history of decades of frequent masturbation, this is a different world.

I am thinking about my own orgasms and sex for myself much, much less. Instead, I find myself driven to please Mistress. When she sighs contentedly after I’ve applied lotion and massaged her hands or feet or legs, I feel complete. It’s hard to describe the satisfaction I feel when I know I have pleased her.

Yesterday before bed she brought up her lack of interest in tiny. She said that her bisexual side is really blooming now, particularly with me crossdressing a lot more and my active exploration of my gender identity issues. I know she fantasizes sometimes about me being a fully physical female. She said “As a result, I find myself thinking less and less about tiny – if that’s even possible.”

And that’s true. She’s shown absolutely zero interest in releasing me, allowing me to orgasm, or having intercourse with me. No teasing or discussion about it even. And I’m not allowed to bring those things up. She said “I’m almost to the point where it wouldn’t matter if tiny just fell right off. But I suppose there may yet be some use for it, such as to invert it into a vagina.” Although she’s teased me with this before, she actually meant this to some degree this time.

Last night she allowed me to lick her to two orgasms. I was struck by how content and fulfilled I felt, despite having absolutely no relief for my own arousal. In fact, I barely noticed that I was also turned on (the smell of her sex always makes me try to get hard). When she was done using me for her pleasure, it felt so clear that I was fulfilling my purpose. Her happiness made me feel very happy, and that’s all I wanted.

Over the week I’ve shaved off all my body hair below the neck. I’ve never really liked having man’s body hair. I’ve always thought that really hairy guys looked gross. I don’t have a lot of body hair, but I much prefer having none. I really enjoy the sensuality of being hairless. Clothing feels different, even the air across my skin when simply walking feels different. I was also surprised at how much of my genital area I was able to shave, even with the cage on. That was a pleasant surprise.

I have an idea for sharing my newly hairless body with Mistress this weekend. I’ll write more about how that goes next time.

First 24

My first full day of true chastity has gone pretty well. Being locked up like this isn’t too physically different, but mentally it is.

I never had any intention of defeating my chastity devices. With both the plain JailBird and the CB-3000, pull-out was always an option. I guess I did pull out once of the plastic unit, but I didn’t masturbate, I just put myself back in. Now I cannot pull out due to the lock that goes through my PA piercing and the end of the JailBird cage. True chastity.

Physically the cage feels about the same. But mentally I know that I am truly trapped in it now. No escape. She has hidden her set of keys. And she said today she’ll be checking the emergency key box weekly to ensure that it isn’t tempered with. Without access to the keys, my cock is trapped in this cage for real, 24 hours a day. No erections, no masturbating, sitting to pee, and my cock is always less than 3 inches long at all times. And the craziest part? I helped make it happen.

The PA lock is very secure, but it offers a little more discomfort than the simple captive-bead ring that I got when I had the Prince Albert piercing installed. I’ll go into more detail about all the pieces and parts in a few weeks. I’m pondering a product review posting for Altarboy’s chastity site.

My wife seems serious about having this chastity experience be real. By that I mean under her control. I was a little surprised when last night she told me we’d have to get good at this “milking thing”. I didn’t even know she knew what prostate milking was, so that indicates she’s been doing some reading about chastity on her own. That’s a good thing, but it was a surprise to me.

She said she didn’t know much about milking. I reminded her that we have an Aneros unit that should make it easy (we haven’t used it). She said that’s fine, but she didn’t know how, so maybe she’d just have me do it. That sounds pretty humiliating. To not be permitted orgasms, and then to have to penetrate myself anally to force my built-up cum to dribble out. Well, she gets to decide that.

I also realized that milking isn’t usually necessary unless the time between orgasms is long – typically over a month. So that suggests that she’s planning for some long-term lockup. She did ask me what my longest time being locked up was, but I honestly didn’t remember.

After she locked me up yesterday I expressed a little disappointment that I hadn’t gotten to be inside her first. I had held out just a little hope that she might let me fuck her one last time. She was pretty annoyed at me even bringing it up. And she said I was not to mention it again unless I wanted my lockup time seriously extended. Her reaction both surprised and aroused me. She is serious about being in control.

I sincerely was kind of bummed, though. The last time she permitted intercourse was Thanksgiving, about two months ago. Fortunately I can remember it vividly. She’s allowed me some orgasms since then, by either her hand or mine. But I’ve been begging and longing so much to feel my cock inside her again. However, I understand now that sex with me is clearly not on her to-do list.

She continues to talk about her fantasies of black men and their nice big cocks. She teases me about how nice it would be to have one inside her, and how she’d like to make me watch as she fucks men with real cocks. I’m still not sure how serious she is. I do wonder if it’s more likely now that she intends for my cock to be locked up for a long time.

There was a black man she found on-line who lives nearby. She contacted him, but he hasn’t responded. It could be that he’s abandoned that profile. Or who knows, my wife could be talking to him by phone tomorrow. Or maybe she’s looking elsewhere.

Last night she allowed me to lick her pussy until she orgasmed. I find that so fulfilling lately. Her smell and taste really arouse me, so it’s a bit painful to try to get hard with the chastity cage. But that doesn’t matter, she’s using me to pleasure herself, and that means a lot to me. I feel very gratified, it’s a meaningful experience for me. I find her pussy beautiful and fascinating, and I will worship it whenever she asks.

I’m suspecting that my chastity experience will transition into a more long-term journey now. I may post less frequently, depending on what events occur. I’m aware of wanting to keep the interesting-to-mundane ratio high in this blog.

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