My Anal Orgasm Chal...
 
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My Anal Orgasm Challenge


Helghast
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Hello gents!

From the start of my pegging fun with my wife,she expressed the wish for me to have a completely stimulus/handsfree ejaculatory orgasm from pegging alone. Something I find extremely difficult. Sure,she loves my prostate orgasms,but she needs to ‘see’ an orgasm for her own needs. Rightly or wrongly,being able to shag the cum out of me is just something that’s important to her.

@rumel kindly posted a link to the 30 day anal orgasm challenge. So after a little research,she decided a chastity cage will be a good way for us to proceed. This is to ensure no masturbation or cheating throughout,though I like to think I can be trusted,she’s not taking any chances ha ha So I’m wearing it until she’s had what she wants. This includes any sexual play. It will only be removed for pegging. I asked how the sex thing will work. She says intercourse for me is out of the question until she’s had what she wants. But she’s also promised if Im good and get my act together with the HFWO,I’ll be well rewarded,she wants to train me to be able to do it when she wants.

Though things don’t stop for her. I have my oral duties and toys to see her through,and if she gets needy,then intercourse will involve me wearing the strap-on for her. I also get that impish smile and teased that perhaps if i take too much time,and she gets frustrated enough,she might have to be satisfied elsewhere. That stuff is doing me no favours at keeping erections at bay!

It’s only been a few days and I’m gagging already. Chastity is hard. Morning erections can be a bit sore,a visit to the bathroom brings much needed relief. I’m learning to manage day time erections. I wake sometimes in the night with nocturnal erections but it is what it is. Wife is enjoying the control of my penis immensely. Something she reckons she should have done from the start!

I’m allowed to A-Less at playtimes,but that’s been affected by the cage too. The oral demands come sporadically. Sometime it’s 5mins and she has one orgasm. Other times it’s 30 mins and a bunch of o’s. Different times too. Things for me get good,then erection comes,and the cage stops it. That can throw me off a bit. So I’m having to get used to that,trying to do a spot of re-wiring. Rather than prostate o or dry o,I’m coining the term FRUST O! I think any o’s of mine are pure frustration.

It’s a long time until Friday night when I hope to get pegged again,I can’t see it happening in the week.I’m not sure I ever imagined life being this way,but I’m really getting into it and while there is frustration,pleasure is much more ‘pleasurable’ if that makes sense. I gotta get my work put in and get out of this cage. Though I doubt this will be the last time I wear it ha ha.


   
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 MBtS
(@mountain-below-the-sea)
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It sounds like you're having a blast mate 🙂 

 

Just curious - was your sexual relationship with your wife always this adventurous?


   
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Helghast
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@mountain-below-the-sea

That’s a loaded question ha ha. 
I’d say our sex life was just normal. We both loved sex. A typical couple.

Adventurous when young,at it like rabbits. Did all the positions and places etc. Again,probably quite typical across couples. Nothing too fancy I guess. But we did keep it going into our 40’s.

Then i discovered the prostate journey.Then she got involved.Both of us had uncharted territory to explore. I started to explore the submissive side of me,she started to explore the dominant side of her,we both found we really like the role reversal,her I think her even more than me. And here we are. I did say to someone on another post,that as far out as I thought I was when younger,I’m kind of thinking now I wasn’t as far out as I thought. 

 


   
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Ggringo
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Posted by: @helghast

 

 A typical couple.

 

Not! 

Yes, adventurous at first; sex on the hood of our car at the cottage,  sex in every room of the house,  outside on lawn chairs, strip card games and more adventures but somehow it all melted away.

 

For some of us, sex is either a distant memory or it's on-going self pleasured.  Mine is the latter and I  thank the stars for prostate play!


   
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Helghast
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Posted by: @ggringo

Not! 

Yes, adventurous at first; sex on the hood of our car at the cottage,  sex in every room of the house,  outside on lawn chairs, strip card games and more adventures but somehow it all melted away.

 

For some of us, sex is either a distant memory or it's on-going self pleasured.  Mine is the latter and I  thank the stars for prostate play!

If it came across offensive in some why,I apologise.That was not my intention. When mountain asked were we always an adventurous couple,I assumed he was referring to yesteryears. I figured being adventurous and at it like rabbits was typical for most young couples. Not with this kind of stuff though.

Coming into our 40’s,we still enjoyed sex,although the planes,trains and automobiles etc had cooled off a little. A lot more quickies in the week,only really weekends providing time for extra.

But my prostate journey has really spiced up the excitement between us. Her getting involved is the best things that could have happened to my journey. Now there’s some new twists and turns in the road that I didn’t know where there,she’s took over a bit,but that’s women 😉

 

 


   
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Ggringo
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@helghast, don't apologize my friend, no offence taken!

 

My point is that what you and your wife have is not typical of married couples (at least I don't think so).  Your approach on sex as a long time couple is special and not to be taken for granted.

 

I tip my hat to you both for seeking new ways to keep your sex life active and satisfying.  Keep sharing with us!

 

Enviously, Ggringo

 


   
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Helghast
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@ggringo ok cool. I just read it wrong,I thought I was being chastised ha ha.

Yea well I guess we just really clicked with each other. I still love her now like I did when I was young. Never was tempted to step out,or even find someone new. Sure we’ve had ups and down like anyone else,but we work.

 

 


   
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Helghast
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Update:

Friday night came and went.  No pegging boo hoo!  Chastity is driving me crazy. I’m horny all the time,I just can’t get enough release. Not even prostate orgasm relieves all the tension. The witch thinks it’s brilliant....I’m ready to smash someone’s face in Hahahaha


   
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Helghast
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Update 2: Saturday nights the night! 
Erm no! No pegging last night either,she’s decided to keep me in chastity a while longer to make sure I play ball.

We? I? Did have intercourse.  I donned the strap on with one of her own dildos. Was a bit awkward but the job got done. She said,whilst it’s not as good a the real thing,she rather enjoyed herself.  It was quite funny actually,we laughed a lot.

The humour had me on the up and up. Then she  brought me back down with a thump at the end. She said it was quite good to have no wet patch,or anything wet trickling down her leg,then playfully threatened that maybe we could get used to that. I wanted to cry hahaha.

She reminded me as long as I’m a good boy,I’ll be rewarded. I’m not sure I can take another week of chastity though. Maybe I’ll get the axe and go fell a big tree. My cortisol is bubbling lol.


   
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Bro, you're living out my fantasies in real time. I don't know if I'll ever get there with my woman, but you give me hope. Thanks for sharing your journey.


   
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I have no experience with pegging, know zilch about dominatrixes, and nothing also about chastity for men with forced genital devices.

Yet in my own masculine soul, it seems to me that part of the thrill of all that Helghast has experienced is knowing that your wife or partner is thinking about sex as much as we men do.  For me and for all men who are truly men, that would be huge- -we men think of sex all the time. But as  for my sweet wife, I think her thoughts of sex and the thrill of sex are maybe incidental or rarely.  We have had good years of good intercourse sex, but when the wife takes the reins, something ignites in a mans soul and something ignites in the marriage.  The marriage becomes on fire and that fire cannot be extinguished as the wife is in complete control and  keeps pouring more fuel on the fire that makes the fire uncontainable and unpredictable.

Just my thoughts.  I may be totally off course here and criticism of my thoughts would not offend me.

Helghast, I envy you bro.  Live it to the max and let your body dictate pleasure to you not known to many men.  Thanks for sharing your life with us underlings.  


   
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Helghast
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@hrunting Sure you will. Start suggesting 😉

 


   
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Helghast
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@turnrow

Posted by: @turnrow

knowing that your wife or partner is thinking about sex as much as we men do. 

Fortunately we’ve always been on the same page with sex.

 

Posted by: @turnrow

when the wife takes the reins, something ignites in a mans soul and something ignites in the marriage.  The marriage becomes on fire and that fire cannot be extinguished as the wife is in complete control and  keeps pouring more fuel on the fire that makes the fire uncontainable and unpredictable.

That’s what I’ve said. It’s has reignited the passion,spice,a new honeymoon period of you like. She’s really grown in her new role. Excited. I’m a mixture of excited and scared about where and how far she’ll go with this,and what how far she’ll push the boundaries.

 

 

Posted by: @turnrow

Live it to the max and let your body dictate pleasure to you

I think we are way past me or my body dictating pleasure,she’s doing the dictating,and I think it’s here to stay. Once she came on board my prostate journey and saw what could be achieved,there was no turning back lol.

 


   
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@Helghast, I recently gave up control of my orgasms to my woman, and we have moved to an appreciation of how much more energized (and attentive) I am when I don't cum as often. It has been a very slow, gentle, vanilla approach, but she's been receptive to it, and I'm amazed at the change in our relationship--for the better. I'm just starting my Aneros journey, so I'm nowhere near inviting her along for the ride, but I hope to get there one day.

@Turnrow has exactly said it. I think all men want a woman to love us as we love them: with the kind of erotic passion and desire that we typically feel for them. To have that returned... Having given my woman total say in what we do, and when, and how she wants to respond to my desire for her, has given her a freedom she maybe never had before, and she is relaxing(?) into it. She's not yet pouring fuel on the fire, but she is tending the flame, and I'm in awe and loving it. As she grows more comfortable with this newer arrangement, I'm hoping her willingness to open up more and be more adventuresome will blossom.


   
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@helghast Excited and scared at the same time. That's a heady brew, indeed.

 


   
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Helghast
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@hrunting 

Posted by: @hrunting

, I recently gave up control of my orgasms to my woman, and we have moved to an appreciation of how much more energized (and attentive) I am when I don't cum as often. It has been a very slow, gentle, vanilla approach, but she's been receptive to it,

Have you considered suggesting a chastity cage to her? I’ve been in mine about a week now. Wife is really enjoying it. She has the key,and it’s not coming off until she wants. She has control over my erections along with ejaculations. 

Posted by: @hrunting

I'm hoping her willingness to open up more and be more adventuresome will blossom.

Maybe you’ll get dominance in place of openness hahaha 😉

  

 


   
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@helghast I've had a couple of cages for about a year now and would wear them occasionally, though she never knew it. I enjoyed wearing them, but usually it was for several hours during the day. I wore one over night just once... and woke to feeling my balls being ripped from my body from a night time erection. My woman doesn't like the idea of the cages, and has said so explicitly, so there's no reason to bring them up again anytime soon.

Moreover, the approach we've taken to giving her control includes the idea of celebrating and appreciating my desire for her, especially as it manifests in an erection. So, squelching my boner is contrary to the messaging and I haven't touched the cages in months. That being said, I would like to be able to wear something around my equipment as a sign that I am hers. I have an idea for a small charm or some such thing; in a couple of weeks, it'll be the 3-month anniversary of her taking control, so maybe I'll bring it up then. I don't mind suggesting it, or even getting it myself, but it would mean a lot more if she picked it out and bought it for me.

Frankly, scary and exciting as it is, I would be ecstatic if her openness led to more dominance. As I said above, you're living my fantasies in real time. (I know, I know: be careful what you wish for...)

 


   
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Helghast
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@hrunting

 

 

Posted by: @hrunting

My woman doesn't like the idea of the cages, and has said so explicitly, so there's no reason to bring them up again anytime soon.

Fair enough. I didn’t know you already had a couple. Mine fortunately or unfortunately isn’t a choice hahaha.

 

 

Posted by: @hrunting

, I would like to be able to wear something around my equipment as a sign that I am hers. I have an idea for a small charm or some such thing; in a couple of weeks, it'll be the 3-month anniversary of her taking control, so maybe I'll bring it up then. I don't mind suggesting it, or even getting it myself, but it would mean a lot more if she picked it out and bought it for me.

Ownership comes in many forms! That sounds pretty cool. Yes,it does mean more then they do it themselves. My wife never had an ounce of dominance in her IMO until she got involved in my prostate journey. Boy,did she change and discover herself lol.

I hope you get all you want mate. 😉

 


   
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can you post the link to the anal orgasm challenge? I can't find it!


   
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Helghast
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Bro.  If she is playing with you to the PONR daily as set out in that link or if she is massaging your prostate or doing anything to keep your arousal near ejaculation daily, then bro, I realize the heaven you are in physically and sexually.

Would to God my wife would touch me sexually daily in at least one small touch erotically.  

Keep us posted on your arousal level and what she is doing to keep that high?  Thanks for sharing.

 

 


   
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Yeah, bro. What @Turnrow said.


   
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Helghast
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@turnrow No playing with ponr. She doesn’t think she needs to,she’s confident that she’ll achieve her goal when she takes the chastity cage off.

No massage either. I’m getting nothing until I’ve done what I’ve got to do.

She doesn’t even need to do much for my arousal,I’m horny constantly. I’ve had about a million attempted erections from kisses,hugs,washing her in the bath,performing oral,using a vibe on her. She’s only gotta touch my arm and I’m practically foaming at the mouth. It doesn’t take much if I’m honest,it’s 2 weeks now since I’ve ejaculated,last time it was this long was before puberty lol

She drives me nuts at work with erotic texts. What she needs,who she might have to get it from because I’m locked up so i’m no use to her. Reminding me if I’m a good boy and play ball when the cage comes off I’m in for a real treat. 

How I feel is this...every emotion we have swirls around constantly,I’m horny,frustrated,happy,sad,angry,jealous,euphoric all at once virtually. I do my best to A-Less but the cage heads off the erection caused,which kinda dulls things. I’ve had some orgasms but they just arent enough. My cortisol must be through the roof.

Better be this weekend,but I think she enjoys a little too much, pushing to see how much I can take. Like everything else in what femdom appears to be,it’s heaven and hell rolled into one.

 


   
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Helghast
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@hrunting yea bro lol am getting that desperate now,i could possibly consider a bromance hahahahaha 😉

 


   
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@helghast <snort> If I could encourage my woman to a quarter of that much initiative...

 


   
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Helghast
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@hrunting well your lady is already pretty open,start nudging 😉

 


   
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@helghast OMG this is intense! I love the sound of it.

Sounds tough though. First I thought is "wow blue balls like crazy I bet!!" although I can handle quite a bit of teasing without aches and pains down there. My wife, back in the day, used to suck me to tease me sometimes 5+ times a day, morning in bed, random times during the day, at night before dinner, and after dinner, and then of course, sex. So fun! I feel like I can definitely handle this challenge and welcome it. I will for sure be shooting off between days 7-14 I bet, I don't think I could make it to day 30 she'll certainly peg me to completion without having to try too hard.

You're in a cock cage the whole time!? Does she peg you with it on? Will you finally have full release with the cage off and her cock in your ass???!!! Also, how often does she peg you?

 


   
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Helghast
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@techpump Yes its really tough. If I didn’t have the gym I think I’d die lol. This week I’ve nearly trained to death in a vain attempt to suck all the testosterone out of my testicles lol It’s not working!

No pegging,or any other stimulation except some A-Less whilst pleasuring her. That’s not working right as erection cycling is blocked by the cage. She feels it’s the best way to meet a specific objective.

Hopefully I’ll be freed at the weekend. What normality will be then I’ve yet to discover.

 


   
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@helghast 

This is awesome, baseball bat.. mmnnn


   
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