I am not sure where to put this topic, so if I have it in the wrong forum, please feel free to move it. I have been talking to an online girl a bit the past two weeks and she knows I'm a submissive. She seems to like the idea of pegging and thinks someday I should try orgasming anally. In order to simulate it, I have been trying to finger f**k my behind just to see what it would be like. I've held off on orgasming the past four days just to try and help enlarge my prostate. Anyway, tonight I had a breakthrough. Every other time (and there have been a few in the past) where I have attempted to self finger, I have gone immediately limp. Tonight I remained hard the whole time. Is this a sign that my desires are changing? Anyone have any suggestions on how to bring on the anal orgasm? I know longer mental chastity would help, but is there any way to encourage it faster? Also, after you move your desire from the tip of your penis to your behind, is it possible to move the desire back?
This is something I am interested in but have yet to experience. My Wife has made me buy an anal probe and a prostate massager from Lovehoney but has not used it on me yet. Moving our relationship to a point where she is comfortable inserting things into my anus is a jump that we are taking our time with. She loves stimulating my bottom but apart from a small part of her finger she has concentrated on doing this with rubbing and pressure in the area below my balls and around my anus. A prostate massager can be used to help you release semen (not the sperm though, that gets mixed in from your testicles.) I have also seen videos of guys doing the same thing using various dildos. I would get a Tumblr account and search for chastity blogs, you are bound to see some for yourself. As for going limp that is completely normal. To relax your anal sphincter to a point where you can accept larger objects it is normal to lose your erection. I have stayed hard when my Wife plays with my bottom but I have also gone soft as well. I had to reassure my Wife that I was incredibly turned on and she is now happy with the idea and understands why it happens.
I have tried stimulating my prostate by using a vibrator anally and had some luck. I too will go limp shortly after insertion even if I am rock hard to start. I have not gotten my wife to play back there but would be curious to know if I would stay hard with the added mental stimulation. I have yet to have semen come squirting out of my cock like I am cumming, but I can get it to drip out very slowly. It is more of a slow build to get there and not coming for several days before really helps. Do not rush it. As far as moving the desire, for me it is not something where the desire moves, it is just something that feels different in a really good way.
I've been into anal play for years, everything from strap on's to E-stim. It really is a fantastic feeling, I have had some of my best orgasms from them but it's always combined with stimulation of my penis. I've never had a full blown orgasm from anal play alone, but have come close many times. Recently after a period of being locked and denied it was very close, but still no full blown orgasm. I don't know of any tricks to achieve one and have never lost the desire to have my penis touched after rounds of anal play. I find that anal being locked in the cage is a whole new sensation, without the penis being touched it's much more intense, almost to the point of not being able to take it after awhile. We keep on trying, she loves it as much as I do and one of these days it may happen. In the meantime it still feels great!
I recommend an aneros device. I don't want to sound like a shill but it is a wonderful device. I have the prograsm model. I took me a lot of time and patience (6-8 months) to master the device but once it worked for me it became very easy to repeat the experience. I can now get off in about 10-15 minutes. I have not been able to get off anally without the device yet but I think we are getting closer. Don't expect to ejaculate with it but it does provide some mind blowing orgasms and no refractory period to speak of. Some quick tips if you decide to try one (which may also work without one: 1. Be really really really horny. 2. Don't try to force the orgasm you have to let it come to you. (Easier said than done. This was my big problem.) 3. It helped me to be a little tired/foggy headed during my first major breakthrough experience but that may not work for everyone. 4, Find some meditative breathing exercises to help you relax. 5. Read everything you can about it from other users that have had the experience. 6. Avoid distractions. 7. Don't get frustrated if it doesn't work the first/100th time just keep trying You are still getting a nice internal massage. 8. Don't try it on an empty prostate. It works better if you are pent up. When it worked for me the first time I made a commitment to myself to not get off "traditionally" until I was able to get off with the device. It took about 6 weeks but was way worth it.