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.

Having it Her Way

We’ll be going to a kink party next week. Mistress isn’t sure what she plans to do with me then. But we do plan on having me come out to everyone (as a transsexual).

They already know me as a part-time crossdresser. But my persona at those times was a ditzy, funny, slutty, “blonde” female. Of course my new presentation will me instead. It will be interesting.

We fully expect everyone to be quite supportive. The BDSM community has plenty of GLB and T folks, and we personally know many of them. So the risk is low here for coming out. A few already know.

Mistress talks about my post-op situation sometimes. Once tiny (her name for my cock) has been turned into a vagina, she has plans for me. One is to fist me. She also plans to fist me and another woman at the same time at one of these parties. The three of us have done that once before, but next time will be different (3 women).

She’s also talked about finding men to “have their way with me”. She’s mentioned some specific names too, and that she plans to talk with them about their interest in having sex with me after my surgery (and after healing of course). She’s also mentioned setting up “rape scenes”, which excites me too.

I’ve realized that one of my core aspects is finding pleasure in providing sexual pleasure for others. I love it when Mistress orgasms using me in various ways, particularly when she ignores what she calls “my poor excuse for a penis”. And I realize that letting men eventually use me for their sexual pleasure is almost certainly likely to leave me feeling the same way – satisfied that they achieve orgasm, even (and particularly) when I don’t.

However, I understand that I’m likely to be orgasmic after SRS (Sexual Reassignment Surgery). Although I’m certainly looking forward to that, Mistress has made it clear that she plans to have me in chastity then as well. So at some point I guess we’ll be investing in a female chastity belt.

Surgery seems like it’s about 2 years away, possibly a little less. I’m hoping to be evaluated for female hormones later this month, likely having a prescription within a month. Time to grow breasts!

Mistress talked with me about my cage today. She insists that tiny will remain locked up for now, with no releases planned. She said she was unhappy with my behavior during my week out of the cage a month or so ago. I don’t recall specific problems, but I’m in no position to argue. It’s just a bit of a hassle to try to tuck my male parts out of the way when I crossdress, due to this stainless steel cage locked onto them.

Another one of my core aspects is being submissive to Mistress. As I transition from a male into a female, I fully expect to remain submissive to her. That is what we both want. I will remain her chaste, submissive pet.

Coasting

We’ve been into a pattern lately where my wife/keyholder will have me locked up all week, Monday thru Friday. Then on the weekend she has me remove the CB-3000, wash Tiny (her name for my cock), and supervise my release from chastity over Saturday and Sunday.

Both this weekend and last weekend I have been permitted to orgasm, but only after she has had a chance to climax at least once.

Friday night was an example. She allowed me to slip inside her. After having been locked up a week, intercourse feels incredible. But on top of that, she started playing with my nipples which drives me crazy with sexual energy. She had not cum yet so I had to stop and stay still, and I had to beg her to quit stimulating my nipples. So she left my nipples alone and focused on her orgasm, which arrived before long. I waited until she was ready for me to continue. Then she went back to my nipples, and in no time at all I had a long and satisfying orgasm.

Saturday night she was a little miffed at me for not being interested in going out to a drive-in movie. I was exhausted from lots of yard work, and had a few other reasons. But she was certain that my orgasm the night before had reduced my interest in sex. In fact, she was so annoyed by this that she said she would find another man to satisfy her since sex with her didn’t seem that important to me. I tried to plead my case, but it was hopeless. She also suggested leaving me locked up for two week periods instead, or maybe permanently once she found another lover. And her plans are to have me watch while she is satisfied by another man with a cock that isn’t Tiny. To be honest, I’m not sure how serious she is. She might do it.

Last Thursday she gave me an opportunity to be released early. We were meeting a friend for dinner and she wanted to be sure we were on time. I left on-time from work, but hit unusually heavy traffic on the way home, and then again on the way to dinner. We were a few minutes late, and so I stayed locked up for two more days.

A week earlier she allowed me to get unlocked for the weekend and wash myself up before bedtime. It was another evening when I was exhausted, but apparently she was hoping to use my cock in an erect state for her own pleasure. Tiny stayed soft as she played with him, and she talked about how useless he was. “Look at how small and soft this thing is. It certainly isn’t going to give me any pleasure tonight, is it? What is the point of even having it? Perhaps we should have it removed, or better yet turn you into a woman. Then I could fist both your ass and your pussy.” I agreed, being too tired to argue at all.

We both have tomorrow off work, just to make a 3-day weekend for us at home. So I’m not sure if she’ll want me locked up in the morning, or if she’ll just keep me “supervised” during this extended weekend. The freedom or imprisonment of my genitals are up to her.

500

Saturday was quite a special day, both for my wife/keyholder/mistress and for me. Her birthday was that weekend, and she decided that I would receive birthday spankings on her behalf. Rather than use her age, she set a high goal for me to earn release from chastity and an orgasm: 500 spanks.

With her help we made a little progress towards that during the week: 15. Only 485 spankings to go.

On Saturday we attended a play party with friends. This was a kinky party at a friend’s house in their BDSM dungeon. About 30 people attended. I picked up a Byerly’s birthday cake that was decorated with roses. I asked them to customize the frosting with her name, and to add thorns to the rose stems, which they did.

After we arrived at the party, my wife suggested that I let people know about my predicament. Most folks I asked were happy to help out by spanking my ass. So with my pants at my ankles and my CB-3000 visible, I received scores of birthday spankings. Most used a nice leather paddle that my wife prefers (similar to this but red). However, a few used their bare hands. Before very long I had over 300 and was pretty sore and pink.

Soon a special friend arrived at the party. I had phoned R earlier and asked her to participate in a special scene that my wife had wished for. A short while later the three of us were on the dungeon floor, where R and I stripped and laid down next to each other. My wife put on gloves and proceeded to fist us both at the same time. I was still locked in chastity, but during this scene R had three orgasms. My wife/mistress loved having one hand inside R’s pussy and the other inside my ass.

After that scene we cleaned up and then mingled with our friends some more. I asked for additional spankings. My wife said I had to stop at 480 so she could take over. I suspected she might quit at 499 and leave me locked up for the night. Indeed, at that point she administered the next 19 herself and stopped. I begged and pleaded for one more. To my surprise, she layed into my red rear with one more hard one, bringing my total to 500.

I asked to be unlocked, and she instructed me to retrieve the key from her keyring and ask someone else to unlock me. As it turns out, the couple who introduced my wife and I to each other were at the party, and I asked him to unlock me. He was happy to, as I suspected he might be, since he is also locked up at times. He knew what it meant for me to get unlocked.

Back in the dungeon, my wife had me strip again and lay in a leather sex sling with my legs up (like this but without the ropes). Apparently my orgasm would be here in front of everyone watching. She whispered something to R, who disappeared for a short while. My wife produced our largest dildo (similar to this), ready with a condom and lube. She held it at her waist and started fucking my ass with it. Due to it’s size, this is a very intense experience for me.

R returned and my wife asked her to masturbate me at the same time. A minute later my wife told me to close my eyes, turn my head, and open my mouth. I did so, and someone shoved their cock down my throat. He grabbed my hair and proceeded to fuck my face. I can’t do justice to how amazing this was – to be simultaneously used at both ends and jerked off. With so many sensations going it, it took me a few minutes to focus on the orgasm that was building. But before long I came and came and came. Having been locked up for a week, it was a wonderful orgasm, and the additional penetrations made it even more intense and incredible.

I opened my eyes and recognized D, a substantial presence in the local scene, as he took his cock out of my mouth. We both laughed, since I had sort of owed him this for a while. About a year ago I was crossdressed at another party here. Sitting in his lap, I got him all turned on but then had to run to a scene when my mistress called. Since then he had teased me about “finishing the job”.

Of course I’m locked back up now. My wife has been very appreciative of the dual fisting scene I helped arrange for her. And I’ve been so grateful to her, not only to have had an orgasm, but to have realized such an incredible fantasy with her. We are both aware of how fortunate we are to be together.

  • Calendar

    • February 2018
      M T W T F S S
      « Jan    
       1234
      567891011
      12131415161718
      19202122232425
      262728  
  • Search