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.

 

Scary Saturday

So my wife and I were out to dinner a month or so ago with a couple we’ve known for a few years. But it had slipped my mind, until he walked into the restaurant, that I had given the man a blow job some time ago at a party.

So here I am, at dinner, with this man sitting across the table, his wife next to him, and my wife next to me.

I should probably also mention that my wife was the one to told me to suck him off at that party.

A few weeks later we go out dancing with them. It’s a bit awkward for us, as two women, to dance in this vanilla establishment. Our heterosexual friends didn’t get the stares that we did, especially during that one slow dance. Ah well, screw the gawkers.

Partway through our dancing, my wife tells me to invite them both to our place in a few weeks. I’m instructed to let him know that my “nibbies” (her pet name for my breasts) need some of his TLC. I’m in shock, but I do as I’m told. He graciously accepts the invitation.

You need to know that he is one of the top-notch whip masters in our local BSDM community. In other words, my wife’s plan is for him to use his whips on my breasts.

So that was supposed to happen today. But unfortunately he got ill and cancelled our plans and others. Annetta said she will reschedule.

I was already nervous, and now I have to wait even longer. Understand that being whipped isn’t the only thing on their agenda. He and my wife have been discussing what will happen at our little private party for quite a while. All she’s told me so far is that I will also be serving them throughout the party.

Last night she picked out my outfit – a black, lacy number that really flatters my figure – it’s hot! A demure black leather collar, and locking high-heel patent leather boots will complete the scene. Oh, and I’m supposed to be sure to have all our gags handy, as we don’t want to bother the neighbors regardless of what happens.

All the rest will be a surprise – for me anyway.

So in this you can probably see that our relationship is still very much intact and going extremely well. We love each other very much. And I trust her completely, enough to let her turn my body over to a friend for him to use as he sees fit.

My wife also told him about my rape fantasies (which I do indeed have). Then she told me “But since you don’t have a vagina yet, that will have to wait until later”. I know non-consensual rape is a very bad thing. But I’ll speak only for myself and say that I’ve had fantasies about being raped, as a woman, all my life. YMMV.

My wife loves to tease me, and humiliate me, including with other people. Being her devoted submissive and spouse, that is just fine with me. It’s one of the many ways I can show her how much I love her (and her dominance).

 

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.

Happy in heels

Things are still going well! I love being in the world as a woman now, instead of as a man. And unlike most married couples to find themselves wrestling with this issue (one partner being transexual), we are still going strong together. I think being openminded kinksters really helps.

I’m still eating out of my dog dishes, sometime 3 times a day. It’s so automatic now. My latest need for punishment has related to being tardy. My wife/mistress does not appreciate departing to an event with me when we are behind schedule. The last time we were 3 minutes late to meet some friends for dinner, she tacked on a penalty 5 minutes because I hurried through a yellow light (her opinion was that I ran a red light). That turned into a paddling with her favorite thick leather paddle, non-stop for the full eight minutes.

And she still has her appreciation for men of color. She rarely misses an opportunity to notice or comment on them, or even flirt with them. Humiliating me remains another past-time, making comments about my sexual inadequacy over the years as a man, and how my penis will be so much better off as a vagina anyway. There is little need for male chastity devices any more, as the female hormones have left tiny barely functional in that regard.

I can’t remember the last time she permitted me an orgasm. Several times per month, though, she instructs me to orally pleasure her, which I happily do. We both really enjoy that, and as a bonus she gets to ignore how horny it leaves me.

Our relationship is doing amazingly well, considering all we’ve been through lately. In many ways we feel closer than ever. And I’m extremely grateful for that. The next (and perhaps final) challenge for us will be the Gender Confirming Surgery (also known as SRS or GRS). She’s worried about infections and other problems. I’m still very excited to have my body fully reflect how I see myself now in the world – as a woman.

As time goes on, I’m less and less comfortable with my male genitals. They are inconvenient, as I cannot dress how I want sometimes. They are annoying, since tucking them snugly so they don’t bulge obviously under my clothes is a hassle. They hurt sometimes, as the atrophy fights with the occasional erection attempt. And mostly they no longer feel appropriate at all. I was in the shower with my wife, feeling horny, and instead of being able to rub my pussy against her thigh this damn semi-flaccid hunk of skin was flopping around. It honestly felt very wrong.

Electrolysis is a pain in the ass. I just completed my 7th trip to Dallas TX where they again removed all the active-growth hairs from my face. Eleven hours of technician time zapping and pulling those hairs one-by-one. Don’t mind the anesthetic injections — by needle into the face. Yeah, it really sucks. But most transitioning friends I know do it locally, without anesthetic, a half-hour or hour at a time. Which reminds me, I have to start that process in my genital area. It’s a strong recommendation prior to surgery down there. Apparently it’s quite painful too. So of course my wife wants to be with me during those procedures.

On the up side, I wore the cutest outfit to work yesterday! And heels, which I love. Actually, I only meant to do a brief post, as I need to be getting ready for work. Dress, jewelry, makeup, hair, and out the door.

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.

Hanging free for now

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

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

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

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

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

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

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

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

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

Boundgasm

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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