Goodbye Y, Hello X

Mistress continues to use me as her urinal at night. For the last few weeks it’s been most every night, sometimes twice. On occasion she will even wake me up to pee in my mouth. Call me strange, but it turns me on. And I also find a lot of satisfaction in serving her this way. See this post for how we manage it without making a mess.

My transition from being male to female is progressing. I’m out to over 100 people now in my life, and am spending about half my awake/non-work time as a female. I started female hormones last week (under doctor supervision). Mistress says she can already see some breast development, but I’m skeptical. She loves the fact that I’m getting boobs, because she’s a lesbian at heart. She is having the best time monitoring their progress and playing with them – multiple times per day. I feel so objectified – she even pulled up my shirt and showed her sister – they were both fondling my breasts.

I don’t mind being objectified – if that’s not already obvious. I’m also finding that I am liking pain to be mixed with my pleasure now. Mistress loves to stimulate my nipples, and I encourage her to bite me as she does, which usually turns her on enough to reach an orgasm.

She’s allowed me two male orgasms over the past 2-3 weeks. They were nice, but still disappointing. The feelings just don’t compare with the female orgasms I am experiencing at her direction. I have to say that males are really missing out on what an orgasm can feel like. My female orgasms are huge, intense, full-body experiences that leave me energized and feeling connected and wonderful. My male orgasms, in contrast, feel quick and shallow and narrow, totally groin-centric, and leave me feeling tired and anti-social. Yuck.

I’m also finding something like body cravings to be female. During my female orgasms I’d give anything to have a vagina and to be getting penetrated right now. It’s a bit shocking to experience, like my body is screaming to be fully female. It seems that Mistress will be easily able to get me into a state where I will desperately have sex with anyone or anything she wants. Eventually.  Genital surgery is 1-2 years away.

Over the next 2-3 months I’ll be coming out to the rest of my family, neighbors, and finally at my work. Then I will be living 100% of the time as a woman. One year after that my doctors would all likely sign off to enable me to get tiny (Mistress’ name for my cock) inverted and turned into a vagina and clitoris. Apparently my testicles (which will have shrunk and become literally useless by then) will just go into the trash.

Until then, the hormones will be changing my body: breasts, fat distribution (face, waist, butt), skin, and brain. I am feeling so ready for this. I really do feel like I’m becoming the person I was meant to be. I’m very happy having this opportunity to spend the rest of my life as a physical and legal woman. It’s definitely not for everyone, but it is right for me.

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.

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