Orgasm Challenge Successful!

Posted: July 15, 2016 in Chastity, Fetish, Key-Holder, Kinky, Male Chastity, Orgasm, Orgasm Denial, Strap-On

​In my last post I wrote about a 5 Day Orgasm Challenge that Angel and I were going to try to accomplish this week.  I am happy to say that it was VERY successful!  Here’s a day-to-day rundown of our activities! 

Day 1 (Monday)

I woke up with my alarm clock, but instead of hitting the snooze button as I usually do, I actually turned it off then rolled back over to face Angel again.  I snuggled up behind her, started running my hands downward to begin her wake-up call, and was very pleasantly surprised to find that she was not wearing any underwear!  That’s pretty rare for her, so I knew that she must have done this in preparation of what we had already talked about doing this morning!  

I began rubbing Angel and feeling how wet she was beginning to get, until she actually began to wake up and rolled over on her back to give me easier access.  At that point I went down with my tongue while slipping about 3 fingers deep inside her to enhance the feeling even more.  It was not long at all before Angel was very much awake and squirming underneath me as her orgasms came in big waves! From this position I can always tell when she gets there and the water works come on full blast squirting pretty much right into my mouth!  

When Angel began calming down from that round, I decided it was time to continue with her magic wand.  A few minutes of that and Angel was in heaven once again and my cage was feeling as tight as ever!  When she had enough, we put the toys away and still had a few minutes to cuddle before I had to get up and start getting ready for work.  This is a VERY nice way to start a day, even (or especially!) a workday!

Day 2 (Tuesday)

Today I woke up a few minutes BEFORE my alarm was to go off.  I was pretty much wide awake at that point so I just turned the alarm off and got up to use the bathroom.  When I came back I stripped all the way down as I climbed back into bed. Under the sheets, I saw that Angel had once again slept with no underwear on, and laying on her side I had a very nice view of her ass!  Not able to resist, I went right in and began nibbling and licking her ass, while at the same time massaging all the way down her legs, feet, etc.  I was doing this for a few minutes before Angel woke up, realized that she needed to use the bathroom herself, so got up and left me in the bed alone…  

You might say that I was already in “ass-mode” at that point, and while she was gone I reached over into our bedside drawer and pulled out a couple of smaller butt plugs and a bottle of lube.  The first one I began working into my own ass, and had just gotten it in and was starting to enjoy that full feeling when Angel came back to bed (now completely naked herself!)  For the very first thing, I turned her over onto her stomach so I could play with her ass some more, and she didn’t complain in the least when I lubed the second plug up and slipped it right in..

Now, with both of us plugged and of course me still caged, I turned Angel back over onto her back again so I could once again have some “breakfast!”  Again slipping a couple of fingers inside of her, I could feel the plug pushing back against me from the other side, and the combined sensations of that plus my tongue sent Angel over the edge very quickly!  

Once she had a couple of orgasms that way, we once again pulled out the magic wand.  This time Angel was not able to go quite as long with that, saying that she was still just a little bit sensitive down there from all of the extra play that we’ve been doing the last few days!  That’s understandable but we still managed to squeak out another orgasm or two before stopping!  Since we’d started a little bit earlier than normal, after a brief rest and cuddle time, there was time for Angel to ride the magic wand on top of me for a little while too!  This always seems to be one of her favorites, as it gives her even more control of how much stimulation she is getting at any given time. 

Eventually, Angel turned off the wand and rolled back off of me, still saying that she was very sensitive right then!  I reminded her that we still have 3 more days to go, and she said she can handle it!    

Day 3 (Wednesday) 

Today I didn’t wake up until the alarm went off.  I was still feeling a little tired so I did hit the snooze button once.  But I DID manage to wake up enough to get things started again with Angel before the alarm had a chance to go off again, so that’s a big improvement in my normal morning routine!  

Once again, Angel wasn’t wearing any underwear, and she was turned kind of half on her back so it was pretty easy access..  This seemed like a pretty good opportunity to try out a new little toy I’d picked up for her.  It is basically just a little set of Ben Wa balls (or whatever this particular brand calls them) which are connected to each other and have the extra little retrieval string at one end.  I started with a little dab of lube on them since I wasn’t sure just how wet Angel might be right then.  The first one slipped right in, I think before she even woke up enough to realize what was going on!  The second (slightly larger one) took just a little bit longer, since by now Angel was stirring more and involuntarily pushing back against this little invasion.  I kept pressing on it while I went in with my tongue, and it wasn’t long at all before Angel was enjoying the sensations and opened herself up to accept the second ball!  

As most people probably know, these balls are hollow and have some other kind of little ball or weight inside of it, so every movement by Angel would result in even greater sensations for her as the weights rolled around from side to side inside of her!  As we proceeded with giving her a couple of orgasms with my tongue followed by more with her riding her magic wand on top of me, Angel definitely seemed to enjoy the added stimulation!  

Once satisfied, Angel rolled off of me and we both laid there for a while to catch our breath.  Angel had almost fallen asleep again when I did have to get up and get ready for work.  I got ready, came back into the bedroom to kiss Angel goodbye, then headed out.  

I was almost to work when Angel called me to tell me I’d “forgotten something.”  Apparently in the heat of the moment we’d forgotten all about the Ben Wa balls!  Lol I usually take care of the toys like that, getting everything cleaned up and put away, etc.  Apparently when Angel got up to use the bathroom, they came on out on their own.  So she cleaned them and got them back into the drawer, no harm done!  

Let’s just say there’s a SMALL chance that I might have remembered that the balls were still inside Angel at least once before I left the house.  I MIGHT have been just a little bit curious to see if she would realize herself that they were there, and exactly how it would feel to her if she did get up and start walking around the house with them still in…  But I will neither confirm nor deny anything with questionable intent!  🙂

Day 4 (Thursay)

Today, we had sort of a double-header!  Angel came to bed last night well after I did.  I felt her get into bed and rolled over to cuddle a bit.  She asked what I was going to “do to her” the next morning, and I sleepily responded that she would just have to wait and find out!  She then took my hand and guided it down her body to show me that she was once again not wearing any underwear.  That was enough to get me to start waking up though, and I couldn’t resist working a couple fingers inside of her!  Angel was immediately very wet and began to moan in pleasure.  I told her that she could have ONE orgasm then, but after that we had to get some sleep and pick it up again in the morning!  

The next morning I woke again with the alarm clock and looked over at Angel’s nice, naked ass under the sheets.  I began kissing and massaging from her waist all the way down to her feet.  It took a little bit longer than normal for Angel to start waking up this time (seems this week might be starting to get the best of her!)  When she did wake up she was resisting me a bit at first by turning towards me and kind of curling into a fetal position making it very hard to access anything!  But I kept at it and soon enough she was on her back again gladly spreading her legs for me! 

This time, I reached under the bed to grab another little toy that we’ve used a few times before but it had been a while.  It’s basically just a little sling, with a soft pillow to go behind Angel’s head, then some straps leading down to some stirrups for her feet.  I got Angel into position and tightened the straps a bit so it would help keep her legs up and knees bent while I went to work with my tongue again.  I also kept about 3 fingers inside of her, and after several minutes of this it felt like Angel came more today than she has any other day this week! 

As we finished off once again with Angel riding her magic wand on top of me, she told me that at first she had kind of wanted to sleep in a while longer and skip the sex for this morning…  But she was very glad that I had managed to change her mind!  

Day 5 (Friday)

We did it!  The 5 day Orgasm Challenge is complete, as Angel and I managed to have lots of fun (and LOTS orgasms for her) every single morning this week!  Today ended up not being quite as much, but it was still lots of fun!  This time I woke up WELL before my alarm was to go off, which gave me time to prepare one last little surprise for the week.  Then I went back to bed and managed to doze off just a little bit more before the alarm.  At that point I started waking Angel up again with my fingers and tongue.  She was very tired and not nearly as into it as some of the other mornings this week, but she still managed an orgasm or two!

When Angel was finished with that, I went ahead and revealed the surprise–which was that I was already wearing our strap-on for her!  I added a little extra lube to it and began inserting it deep inside of Angel.  I must have been a bit too aggressive at first and seemed like I was hurting her, so I slowed down and as she began to relax it slipped right in and she definitely seemed to enjoy the feeling of being filled again!  For me, that is one of the most amazing feelings to be so close and going through all of the motions of regular sex, but to still be denied and not really getting any stimulation from it myself at all!  

This lasted for a few minutes and one more decent orgasm for Angel, but then she was pretty much spent.  She even completely declined her magic wand for the first time all week!  

In Summary:

We did manage to do what we set out to try, but I think it really did wear Angel out to wake up early every single morning for this type of “workout!” I suspect we’ll end up taking a little break from it for a couple days or so, but there’s nothing saying that we can’t try something like this again sometime in the future!  

  1. chazz8ball says:


  2. Ouch, it looks like that cage is taking a bite out of you!!

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