Sissy Had So Many Houses To Get To

Her wife instructed her to personally deliver a special treat to several of the men in their neighborhood.  Sissy had to get to them all before midnight or else she would turn into a pumpkin.

Too Sissy?

Or not sissy enough?

Trick or Treat

She's no Angel.  She's the Devil in Disguise.

What Could This Sissy Have Done?

Something very bad I'm guessing.

Which One Is The Sissy?

Don't Skip Steps Sissy

First step?  Practice your motion.

Second step?  Get used to the size

Step Three?  Enjoy!!!!

I Didn't Know Something Could Be Made To Look More Delicious

Sated

Time for her sissy husband to clean her up now.

Every Fruit Has Its Own Special Flavor

Soon, this sissy's wife will have her lusting after the juice of another fruit even more desperately than she yearns for the juice of this strawberry.

Sissy Got Mad Skillz

First Things First Sissy

Sure you're going to suck it.  But always, always, always get your lipstick right first.

John Was Humiliated Enough When He Was Forced To Accept Work At His Wife's Office As A Secretary

But when his new supervisor (his wife's lover) told John he would be the surprise entertainment for the annual all-male office bash, he thought he would just die.

Sissy Only Had Herself To Blame

Her wife warned her that her new lover did not like it when sissy watched them fucking.  But sissy could not resist and got caught peeking through the bedroom door keyhole.

The next day sissy's wife took her in for these special nipple piercings.  No more sneaking a peek now!

Waste Not. Want Not.

That's what my wife always says as a lover removes his cock from her pussy. 

Sissy Bliss

She wants it all.  But can she take it?

Want!

Oh! My! God!

Ten Seconds

It wasn't a record for sissy.  But it was longer than last month.

Question? Who Do You Suppose Is Responsible For This Look Of Longing And Pleasure?

Her boyfriend?

Or her sissy husband?

Our Weekend Apart Aftermath - Cheerleader Has A Heart-To-Heart With Sissy

[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 - Sissy Adapts To Chastity - Sissy And Cheerleader Spend A Weekend Apart.  These are the previous posts that tell the story about my sissy journey.]

The morning after my cheerleader returned from her weekend in Ft. Lauderdale alone with Randall, I woke up in a funk.  You might call it a ‘sissy funk.’  How do I even explain how it was that I felt?  As I’ve revealed throughout my journaling of my sissy progression, the things that were occurring in my cheerleader’s and my life really began with me confessing to her my deep, dark secret of having this feminine side of my personality.  She had not immediately embraced it, but because she loved me so much, she tolerated it and then began to slowly appear to accept me as I was.  Then, over time, after I further confessed my fantasy imagination, we actually took the step together that led us to where I found myself doubting how I felt about it all.  To put it simply, I was deeply confused about our current arrangement, and I wasn’t very good at concealing it from my cheerleader the Monday morning after her return home. 

On the other hand, my cheerleader woke up in the best of moods.  She seemed positively giddy to me, and I naturally attributed it to the fact that she was thoroughly enjoying her sexcapades with Randall.  As you might surmise, that did not help my funk.  In fact, it only made it worse and I became very pouty as I dressed for work.  To my cheerleader’s credit (and believe me, she sensed my funk), she didn’t press me on the way I was behaving.  But she continued acting as though she thought it was going to be a wonderful day.  She also selected lingerie for me to wear under my suit for the day.  Thus, she wasn’t showing signs of letting me back away from what she had now come to expect as normal for me.  Her selection was not elaborate.  She had laid out for me a pair of rather plain, white nylon bikini panties, a white slip, and an open bottom girdle with black nylon stockings to attach to the garters. 

As she had taken to doing, she lay on our bed and watched me as I dressed in front of her.  That’s when she did something that threw me for a bit of a loop and resulted in me saying something that I probably shouldn’t have said – at least if I had any intention of not letting her know what was eating at me.  I had pulled the panties up my legs and settled inside of them.  Then, I was about to shimmy the girdle on, when she asked me if I was forgetting something.  I honestly did not know what she was talking about and said so.  She held up the bejeweled butt plug Andrea had me wearing during my weekend with her.  I must have looked incredulously at my cheerleader, because that was precisely how I felt.  Surely she did not mean for me to wear it to work?  “You need to wear this,” she said.  I asked her why, and she replied, “Because we want you to.”  We.  She said, ‘We.’  “We?” I asked her, “We?  Who is ‘we?’”  She smiled at me and said, “All of us.  Andrea.  Randall.  Me.  We.”  My irritation and angst was not disguised as I responded, “Right!”  My cheerleader didn’t flinch though.  She simply said, “You don’t want to?  Okay.  No problem.  Go ahead and finish dressing.  I’ll go fix coffee.”   She climbed out of bed, still acting very upbeat and cheerful, and left me to finish dressing alone.

When I got downstairs, she was just as sweet as she could be, handed me a cup of coffee and kissed me sweetly on the lips, telling me I looked nice.  I gathered my things for work and then we kissed goodbye.  I was still in a funk and the butt plug moment had not helped me any.  I was totally confused about where my marital relationship with my cheerleader stood.  Worse still, I did not know how to address my feelings or to talk to her about them.

 Work that day was difficult.  I not only felt all funky about the underlying worry that began my day, but I also felt guilty for the way I’d behaved that morning with my cheerleader.  She seemed so happy (and I really did want her to be happy) and I’d ruined it by pouting and being a baby.  Still, I could not resolve in my mind what to do about my feelings.

I arrived home that evening, determined to put on a better face, and not to make my cheerleader feel badly for feeling so happy.  Apparently, though, she had been thinking about the morning confrontation as well.  She greeted me at the door with a kiss and a glass of Cabernet.  She took my hand and led my to the back patio where we liked to relax.  The evening was pleasant as the sun was making its way toward the horizon.  I sat down beside her, we clinked glasses, and she smiled so sweetly at me, asking about my day.  I wanted to do what I could to make her think things were fine, but as I’ve said, she knows me too well.  She knew I was not right, and she had no intention of letting it slide.  I shared a few details of things I’d done, but I could sense that she was simply letting me prattle on for a while before she focused the conversation upon us.

In the way only my cheerleader could do with me, she asked, “What is wrong sweetie?  I know there is something.  Tell me.  We have to discuss your feelings.”  I knew there was no way she was going to let this go.  On the other hand, I couldn’t find the words to say what was bothering me.  I was in conflict – a deep inner conflict.  But I did not know how to express those feelings to my cheerleader.  She was watching me struggle to respond to her question, and giving me time, but showing no sign of dropping the subject.  “I think you just need to spit it out.  We can talk about it.  Whatever it is,” she urged me.  Finally, I said the only thing I could think of – “I don’t want to lose you!”  There!  That was it!  I was worried that I was losing her to another man.  My cheerleader seemed so enthralled, happy, in love even, with Randall, that I feared I would lose her to him. 

Her reaction to my admission was perfect.  She set her glass of wine down, placed her hands on either side of my face, pulled me to her and kissed me.  Slowly at first.  Tenderly, lovingly and passionately.  Then she kissed me deeply for a long time until I surrendered to her.  Then, when she stopped kissing me, she whispered, “Honey - I love you.  More than anything or anyone.  Forever.  You never need to worry about losing me.  That isn’t going to happen.”  I felt a deep sense of relief, but still felt funny about things.  I answered in a weak, rather whiny voice, “But you seem so into Randall.”  She continued to smile sweetly at me as she began to explain her feelings for Randall.  This conversation may have been one of the most important conversations my cheerleader and I have ever had.

Telling me to listen, she began reviewing things with me, only asking me to affirm that she was correct in her recitation of events.  She basically took me back through our history.  She recounted how I first admitted my fetish to her and she first caught me on the Internet and all.  She explained how difficult that had been for her to accept.  She didn’t need to tell me that, but she seemed to want me to understand how close she’d come then to divorcing me.  Honestly, that revelation set me back.  I had known it was a shock to her, but I did not know my cheerleader had contemplated divorce.  Ultimately, though, she explained that she loved me too much to quit on us, and so she decided then to attempt to work through my revelation and her discovery.  As things moved on, she explained how she came to appreciate what I did for her.  She enjoyed the way I loved her sexually.  I wasn’t surprised when she admitted that, while she enjoyed normal man/woman sex with me, she really enjoyed what I did best, which was provide her oral pleasure.  

She also made her own confession of sorts.  During the time that I was revealing my fantasy of sucking cock, and actually sucking on the dildos in front of her, she was fantasizing about seeing me actually suck cocks.  She told me how hot it made her to see me with my mouth stuffed with cock, even though only rubber, and to hear me talk about sucking cock for her.  She also admitted that my suggestion that other men with bigger cocks fuck her was also an incredible turn on.  Finally, though, she told me that the moment for her that she would never have thought she would get turned on by was the night she jacked me off and watched me swallow my own cum.  She explained what an incredible power rush it was for her to watch my reaction as she sprayed cum into my mouth and onto my face.  I think I knew this already though.  Still, hearing her say so was a different thing entirely.  I sensed where she was heading.  I may have begun our fantasy world, but she was on board with it now.

I was listening closely to my cheerleader take me through the events we’d shared during our now long marriage – over 25 years by this point.  Step by step, she walked me through the stages we had gone through together.  I realized as she talked how true to me she had been.  Perhaps as important, I learned how she had grown as well.  A woman who always seemed such a ‘good girl’ to me (and who still was deep inside) discovered a part of herself that I actually helped blossom.  And so, we found ourselves in the middle of reality, rather than fantasy, and she was thoroughly enjoying herself.  She admitted that she did like the way Randall took her so aggressively.  She liked that she could openly come on to another man in front of me.  But even more, she loved that I would actually participate.  Watching me suck Randall’s cock and then clean his cum out of her was as much a part of the rush she got as him actually fucking her.  The thing she wanted me to face was that I was enjoying myself as well and that I should have no fear of losing her.  She stressed that she loved me no matter what else I might think and that I needed to continue to trust her with my heart.  As if to demonstrate her sincerity, she ended her narrative by saying that if I wanted to stop it all – Randall, Andrea, my sissy ways, everything – that she would honor my request.  But, and she emphasized this point, she didn’t want to stop.  She liked things as they were and wanted to see where things would lead.

 I was, needless to say, left with a huge decision to make.  I had begun this trail our marriage was on – not my cheerleader.  I could not dispute that.  I did enjoy the freedom to express my sissy nature in a more open way.  I could not dispute that either.  And while I was torn with conflict about seeing my cheerleader giving herself sexually so openly and with such vigor to a man, I also had to admit that it turned me on seeing her in that way.  The $60,000 question, though, was whether I could continue to bear it out.  I thanked my cheerleader for her honesty.  I told her how much I loved her.  Then, deciding two things really – one, that I wanted her to be happy, and two, that I wasn’t ready to give up living out my sissy fantasy yet, I told her I wanted to keep moving forward.  My cheerleader smiled lovingly at me and said, “You really are a sweet sissy.  You know that, don’t you?”  I must have blushed deep red hearing her call me a sissy in that way.  Years ago I would never have imagined my cheerleader referring to me as a sissy in such an accepting manner, as she seemed to at that point.  It felt so good to know. 

A huge cloud over our head now lifted, we kissed, and then sat back to enjoy the rest of the evening, sipping our wine until we finished the bottle.  We finally went inside to grab a quick snack for dinner and then went upstairs to bed.  That night I pleasured my cheerleader orally for easily over an hour, accepting that I was going to remain in chastity.  The next morning, after getting out of the shower, I went to my bedroom to find my cheerleader had already gone downstairs to prepare coffee.  On the bed was a set of lingerie for the day and the bejeweled butt plug.  I moistened it and slipped inside of me, knowing that while it may have been Andrea’s and Randall’s desire that I do so, what really mattered was that it was my cheerleader’s desire that I do so.  That was all that mattered to me.  All day at work the plug was a constant reminder of how much my cheerleader loved the sissy me.

Sissy Asked Her Wife Why She Suddenly Wanted Black Cock

Wifey gave sissy ten good reasons why:

One

Two

Three

Four

Five

Six

Seven

Eight

Nine

Ten

Then, for good measure, she gave sissy one more very good reason why she wanted black cock:

'Nuf said.

The Biggest So Far

Next for sissy?  Tyrone!

Sissy's wife knows.  Sissy will never be the same.

Ready For Sissy Hubby

Which One Is The Sissy?

Sissy Really Can't Complain

Since she convinced her wife to fuck other men, this is the only way she's permitted release anymore.