Mistress surprised me last night by telling me to “remove the ring”, which means only one thing: she wanted to have intercourse with me. What a treat!

I removed the 8 gauge captive bead ring in my Prince Albert piercing, applied a touch of lube, and was in position to enter her in near record time. Once inside her, it occurred to me that she might not let me orgasm. I found out later that she was indeed thinking about exactly that – after she had her orgasm(s), of course.

I’d been completely faithful lately under her restrictive honor-based chastity, avoiding even stroking tiny (her name for my cock). So the feeling of sliding into her warm, snug, wet pussy was so very wonderful. No hand job or blow job can compare to the amazing sensation of being inside her.

I took my time, and at one point I just stopped and stayed perfectly still. I had a sense, and I just watched as her orgasm built over the next 30 seconds and then crashed like a wave for her. It felt so fulfilling to be the object of her pleasure like that. I waited a bit, and then asked her if I could have an orgasm.

She thought about it, apparently changing her mind (as I found out later) and allowed me to proceed and cum inside her. My orgasm was tremendous. Denial really does amplify the eventual release, for me anyway. Good thing our windows were closed, I’d have woken the neighbors.

Last weekend we discussed a very interesting topic: my gender-identity issues. As you know, I love to crossdress and have been for decades. My wife has been wonderfully supportive, helping with makeup and hair and even buying me clothes and accessories. But this talk was about my body and my sense of my gender.

It’s complicated. Am I a woman trapped in a man’s body? No. Do I crossdress just for the erotic aspect? No. What do I get out of it? A feeling of contentment and fulfillment, of being myself and whole. And to finally have this side of me accepted is such a gift (my first wife completely rejected that side of me).

Yes, fantasy stories of forced feminization including male-to-female surgery is hot. But expressing my female side is more than a kink or acted-out fantasy. I so look forward to weekends now, as my wife encourages me to let this side of me out as much as possible. Saturdays I am her housekeeper, in white hose and my housedress and satin slave collar, scrubbing her floors and cleaning the house. Sunday she lets me dress however I like. Today is a black skirt, topped by a red/black fun blouse and feathered earrings she bought me. I did my own hair and painted my fingernails black just for today.

Anyway, she was genuinely curious about it all. It felt so wonderful for her to care so much to ask such intimate and meaningful questions. Obviously some paths along these lines could seriously change our relationship. For example, if I wanted to become a biological female and date other men, she was clear that we couldn’t remain married. Ok, that makes total sense. Fortunately, I don’t want to date other men!

She admitted at one point that she would find it hot if I had female breasts that she could play with and suck on. Being bisexual, she enjoys it all. She even admitted that us living together as either literal or apparent lesbians would be totally ok with her. And that sounded exciting to me too.

Don’t think, dear reader, that this is some whim or minor fantasy of mine. I’ve seriously considered my gender issues for many, many years. I would love to be able to live full-time as a woman in the world for some months to really see for myself how far this part of me goes. My wife has offered for us to take a long weekend vacation out of town and do just that together. I love her so much!

My wife even contacted a post-op friend of ours, and a TS-friendly therapist, and has some recommendations for me – professionals I can talk to. I’m seriously thinking about starting that dialog to see where this rabbit hole leads. As I’ve written before, I don’t think I’m a slam-dunk M2F transexual. Then again, if I could get to the point of sexual reassignment surgery as an option, I’d have to seriously think about it.

Perhaps I am an androgyn. I scored lowest on the masculine scale on the Bem Sex Role Inventory (which you can take yourself online here and read more about scoring here). I scored outside of the Androgynous zone just into the “Nearly Feminine” range. My wife took it too (scoring Feminine, not surprisingly) and when she saw my results exclaimed excitedly “we’re lesbians!”. Honey, it’s just a test we took online.

Androgyny is a new role for me to explore. My wife encouraged me to dress androgynously yesterday when we went out to dinner. It was fun. Here is an interesting recent article on an androgyn in the news. Although he’s way too skinny, I’m jealous of his ability to look so damn good!

My wife and I need to talk a lot more. I have no idea where we’ll go from here. I’m going to ask her about talking to a therapist. One thought I had is maybe I can get one of those cards that could keep me from getting arrested for being crossdressed. Yes, in my state it’s a crime for a man to be dressed as a woman in public (6th degree sexual misconduct, if I remember correctly). Stupid, but true.

I’ve been paying a lot more attention to what I’m noticing about other people lately. With women I notice hairstyle, makeup, clothes, fingernails, and especially shoes and boots; although I still observe and appreciate a fit and sexy body shape. With men I’m finding less repulsion (so many men seem conceited and slobby), and that a lot of body hair is gross. I’ve been trimming my own body hair short lately as I don’t like looking or feeling hairy.

I’d be interested in any comments folks have about gender-identity issues.


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