Sunday, August 25, 2013

Cheerleader Adapts To Chastity

[NOTE - Anyone who is just beginning to read my blog, might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow - Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home - Cheerleader Cucks Sissy - Cheerleader and Sissy Are Mentored - Sissy Offers Context For Cheerleader - Sissy Sees Her Future.  These are the previous posts that tell the story about my sissy journey.]
Andrea left my cheerleader and me alone that second Saturday morning after she discussed with us the events of the previous 24 hours.  For the rest of the day my cheerleader seemed to be in no mood to do much of anything.  As much as she appeared to enjoy her time with Randall, I think she was emotionally exhausted from it all - the sex, Andrea's presence in our lives, even me and accepting me being so openly sissified in front of her.  It was odd, really.  I had led us, to a certain extent, to where we were.  But she was the one who pushed us forward by causing the cuckold fantasy to become reality.  Seeing her so smitten and infatuated with Randall, and participating in their sex with them, was very difficult for me to do, as it turned out.  But I was accepting it.  My cheerleader, on the other hand, while benefitting from the great sex, was still finding it difficult to witness her husband as such a submissive sissy - from how I was dressing, to seeing me suck Randall's cock.  It almost seemed, to me at least, that she felt that she had to accept my sissiness as a cost for receiving the great sex, and it was tough, notwithstanding the great sex, for her to do.
That afternoon, as we lounged together on the couch in our den, my cheerleader would ask me to do things for her - like get her a glass of iced tea, or a snack, or a pillow from our bedroom.  Things she might have normally done for herself, she casually asked me to do for her.  I massaged her shoulders, her legs, her feet, all at her request and to relax her.  The day was actually quite an easy day.  We watched television, burning the day that way, almost as though neither of us wanted to confront the elephant in the room.  And by that, I don't mean her fucking Randall.  No.  What was hovering above us was the cloud of what to do about us, when we were alone together, now that I was fully exposed as the sissy I was.  What to do about the chastity situation?  It was as though we each felt the something between us, but neither knew how to broach the subject.  There was an unusual awkwardness between us.  For dinner we ordered a pizza for delivery.  Thankfully, my cheerleader answered the door to pay for it, as I was still dressed as Andrea had dressed me to begin the day. 
When we were ready for bed that night, and we had each put on nightgowns, I decided to raise the subject.  I asked her if she wanted to remove the cage, hinting that I was hopeful that she and I would make love.  Her response, however, was not what I was hoping for.  She replied that she didn't think so, that she was tired and wanted to sleep.  She had been up late the night before she said, intimating that after Andrea and I left them alone, she and Randall had continued having sex.  I was disappointed, of course, but didn't press the issue.  I was finding that I pressed fewer and fewer, if any, issues, instead deferring to my cheerleader.  I climbed into bed and my cheerleader spooned behind me, letting her hand drape over my waist and rest over my encased penis, outside of my panties.  "Take your panties off sweetie," she told me.  "I want to touch it."  At first, I wondered if she had suddenly changed her mind, and my hopes rose.  After I removed my panties my cheerleader cupped my restricted penis in her hand, softly stroking my balls, creating the effect one might expect.  "Does that feel good?" she asked.  I told her it did, but that it also was painful, and asked again if she would unlock me.  Her response was that Andrea had said it should stay on for a few days, at least, so that I could get used to it.  Fuck!  I couldn't believe this!  My cheerleader possessed the key, but apparently she wasn't in charge of the decision whether to release me!  I said, Please?" but my cheerleader only giggled behind me.  "What?" I asked.  "It's just that Andrea told me you would beg at first.  She knows what she is talking about.  You can't be rewarded for begging."  Hearing her words, I lay there quietly, contemplating my circumstances.  No release.  No begging.  So what?  Tolerate the pain?  I tried once more.  "But it hurts."  "Andrea says you have to learn to avoid erections if it hurts too much."  Avoid erections?!  With my cheerleader fondling me like she was?  I was in a no win situation.
We lay in silence.  I accepted that I was fighting a losing battle if I expected release.  My cheerleader had received her instructions and was going to follow them.  However, she was not through with me yet.  Whispering in my ear that she was a little sore, she asked me to pleasure her - slowly and gently.  I slipped down between her thighs and began kissing and licking her smooth pussy lips (I loved her smooth pussy), attending to her for a good while, coaxing her to multiple orgasms, until she finally told me to stop.  My cheerleader fell asleep, but I did not.  I was overwhelmed with a sense of anxiety about the development of being locked in chastity.  I had read about it in fantasy tales, and had even fantasized about it myself, but as with my cuckolding, actually being locked up in chastity was altogether different from fantasizing about being locked up.
My cheerleader and I spent the next day, Sunday, running errands, so I was dressed in my normal male clothing, although I wore panties beneath my jeans.  I actually felt a sense of relief at not dressing in the sissy outfit I'd been dressed in by Andrea the day before.  I needed some male time.  My cheerleader, however, continued to treat me in the most subtlety different way, as though I was there to serve her.  It was not harsh or mean or bossy.  It was simply as though there was an expectation that I would meet all of her demands.  And I did.  And that night, as we readied for bed, I looked at her, hopeful that she would release me, but afraid to ask out of fear of being accused if begging.  My cheerleader wasn't responding to non-verbal begging either, although she did insist upon me removing my panties.  She seemed to enjoy tormenting me, but I wondered if she was actually doing what Andrea may have told her to do.
For the next few days, there was no change.  I remained in chastity, and my cheerleader continued to ask me to do almost everything she might have normally done herself.  Every other day she had me freshly shave her pussy so that it remained smooth, as well as making sure I kept myself smooth all over.  While I was not happy about the way things were going, there were little hints given that I might hope for release soon, so I did my best to maintain a cheerful attitude.  In any event, it seemed as though, whether it was her idea or not, my cheerleader was adapting to the concept of her husband being locked in chastity quite well.  As for her sissy husband, well that was a different matter.


  1. So true Leeanne so true! When fantasy meets reality they don't always merge smoothly. Chastity is something that starts out as physical and ends up mental. It's a frame of mind that took me some time to understand.
    Again many thanks and big kisses for sharing your story!


  2. Thanks again Leeanne ... a nice interim post.

    While my wife won't cuckold me, we did start chastity play almost 2 years ago. I quickly found out reality was not nearly as exciting as my fantasies. Within about 24 hours I was begging to be let out. Like your cheerleader, she held firm. After 48 hours I was a wreck. Before, my sexual fantasies led to frequent masturbation and relief. Now, they let to frustration and despair. It was not fun anymore, merely agonizing. Fortunately, she granted me relief after 3 days, although only after I pleasured her and let her take me with the biggest strap-on I'd ever had.

    Now, I can go about a week without going crazy. During that time, all I want is to do anything that will satisfy my sexual urges, mostly going down on her or giving up my ass to her. She has threatened to do a prostrate massage to drain me and not let me out for an additional week, but has not done that yet. But she usually follows through on her promises/threats.

    So I can feel your pain, especially the first time experience. Of course you are living a much more intense situation with the cuckolding and bi-sexual servitude, but chastity is something people should really understand before agreeing to. Once you give up control, it's over.

  3. Such a bittersweet continuation, Leeanne. Thank you! While I yearn to do this with my Wife (become Her chastised and cuckolded sissy maid), I know in the back of my head that the reality will be different than the fantasy. Nevertheless, my little sissy brain always brings me back to the same place. Thank you for describing the emotions and sensations SO wonderfully... hopefully one day I'll be able to share my own personal experiences!

    Kisses & Curtseys,
    Sissy Maid Tami