Thursday, August 29, 2013

Too Sissy?

Or not sissy enough?

Good Sissy!

Doing what sissies do best.

You've Heard of Hot Yoga?

Well, this is a new yoga class - called Yoga Bare.  Get it Boo Boo?
Oh!  I almost forgot to ask.  Which one is the sissy?

Sissy Knew

Just one look at her wife peeking from behind the huge cock in her hand - and sissy knew her wife would never be satisfied with her little clitty again.

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.


An Apple A Day May Keep The Doctor Away

But what a sissy's wife really needs every day is a good fuck from a man.

Saturday, August 24, 2013

Sissy Heaven

Sissy's wife invited her sister over to meet her recently feminized hubby.  One thing led to another and sissy found herself in heaven.

Wednesday, August 21, 2013

Which One Is The Sissy?


Sissy Knows That Someone Else Is The Father.

She hasn't had sexual intercourse with her wife in nearly a year.  Judging from her size, the best bet is that Tyrone is the father.

Brenda Jones May Have Given Birth To Three Male Babies

However, by the time they were ready to go to college, she had, as she did with her husband, transformed them into beautiful sissy girls.  And they were very close, so that it was no surprise that they were in each others' weddings.

Why Has This Sissy Been Banished To The Corner?

It seems, despite her best effort, she didn't protect her teeth from making contact with her wife's boyfriend's cock while fluffing him.  Bad sissy!

Sunday, August 18, 2013

Sissy Sees Her Future

[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.  These are the previous posts that tell the story about my sissy journey.]
Over a month has passed since my last post, in which I revealed a most significant moment in my sissy journey.  I honestly intended to post an entry telling about the week following the introduction of Andrea into my cheerleader’s and my lives much sooner than now.  And though I committed to myself that I was going to reveal all of the details of my sissy journey on my blog, I have found myself feeling especially worried, or shy, or anxious, or something, about telling about the week that followed me sucking my first living cock for my cheerleader.  Thus the procrastination.  It was, as it turned out, a very mixed week.  It was a week of an incredible high followed by a drop like the bottom falling out from under me.  What happened to me at the end of the week nearly erased the wonder I enjoyed at the beginning of the week.  What happened to me at the end of the week was beyond humiliating.  And I sometimes think back on it and shake my head as I recall that I went along with what Andrea and my cheerleader asked of me.  Finally, however, I have brought myself around and am going to describe the second week of our time under the mentorship of Andrea.  I will try to add current perspective on the events as I tell the details of a week I will never forget, but for purposes of interest, I will focus on how events unfolded in a real time narrative.
As I mentioned in a previous post, Sissy and Cheerleader AreMentored, Andrea took each of our cell phone numbers before she left with Randall, and so I expected that I would hear from her during the week at some point.  However, I did not receive any communication from her until Thursday.  And while I did not know it at the time, it seems that Andrea was communicating with my cheerleader throughout the week.
On the Monday following my cucking, my cheerleader asked me to dress in front of her as I got ready to go to work.  She wanted me to wear a full set of lingerie under my work clothes.  Now, she had seen me dressed in this way before, but she had not seemed so interested before in watching me dress for work.  Before, it was more like she knew I did it, but only tolerated it.  Now, she suddenly seemed interested in watching me don my feminine layer.  I wondered whether it was a direct result of me becoming her cuckold, but I couldn’t decide for certain.  I just know that she watched me, and I also recall feeling a bit self-conscious doing so.  Still, I did as she asked and then she kissed me goodbye and gave me a little pat on my butt, letting her fingers toy with the garter straps attached to my open-bottomed girdle that I wore.  Again, despite my cheerleader’s gradual acceptance of my love of wearing lingerie, this overt teasing was a bit new.
When I arrived home from work that Monday, my cheerleader had prepared a wonderful meal for us.  She greeted me at the door with a huge hug and kiss, and then told me to go change out of my work clothes, but to put on something “pretty” before coming down to dinner.  Even though she was always warm and affectionate with me, I was a little taken aback by her greeting.  Nonetheless, I was beyond questioning her at this point.  If my cheerleader asked me to do something, I tended to do it.  And so, I went upstairs, removed my work clothes, and took a shower.  Refreshed, I then went to my closet and put on some pretty lingerie and a babydoll nightie, and then went downstairs to join my cheerleader for dinner.  It was a strange situation, me wearing a sexy nightgown and my cheerleader dressed in normal clothing, but she seemed to be so happy generally that I accepted that this was what she wanted.
After dinner she asked me to clean the dishes while she went upstairs to shower and change.  And so, dressed in my pretty babydoll, I cleaned the kitchen for my cheerleader.  When she came down she was wearing a short robe and went into the den to watch television.  After I finished cleaning the kitchen, I joined her and she immediately directed me to my knees at her feet, lifting one up for me to massage.  I complied and gave her a long foot massage.  Eventually, she let me know that she wanted me to pleasure her with my mouth.  I was happy to oblige, as there is little else I enjoy more.  As she became more and more aroused, she urged me to join her on our couch and she climbed onto me, settling her wet pussy onto my cock and sliding me inside of her.  We fucked for a brief time as it didn’t take me long to climax, but she seemed to enjoy the moment.  For me though, it was heaven.  I was so relieved that she still wanted to have me in that way.  I had been worried ever since she had been fucked by Randall that she might no longer be interested in me in that way.  But to the contrary, she seemed very interested in making love with me.  Afterwards, I cleaned her out and then she held me in her arms and told me how much she loved me.  I was a very happy sissy to say the least.
The next morning began much the same, with my cheerleader watching me dress for work.  I felt a little less uncomfortable doing so, but still was confused at her new interest in watching me.  And the next evening things went much as they had the previous one, ending with us making love on the couch again.  I began to think that maybe the cuckolding was going to turn out to be a great thing for us, especially if it resulted in my cheerleader wanting me so much between visits from Randall.  Wednesday repeated the pattern of Monday and Tuesday.  I couldn’t recall the last time my cheerleader and I had made love three nights in a row, but I was not going to complain.
On Thursday, though, something happened that shifted things a bit.  Really, it shifted things a lot.  I simply didn’t realize it at the moment it happened.  Around mid-day I received a text message from a phone number that I did not immediately recognize.  It turned out to be from Andrea.  The message was a bit cryptic, causing me to feel anxiety for the rest of the day.  Aside from the message content, I could tell from the message that Andrea and my cheerleader had obviously been in communication throughout the week, and that made me begin to wonder why my cheerleader had not mentioned it to me.  In the message Andrea let me know that she was aware that my week had been very enjoyable for me.  But, she also left me with an instruction.  She told me that my cheerleader was going to raise an intimate subject with me that evening, without specifically telling me what the subject would be.  Andrea explained that I would know it when my cheerleader brought it up, and when she did, I was to say these words: “I want to do it for you.”  Andrea told me that while I would not know what it was until my cheerleader told me, Andrea expected me to comply and insisted that I respond to her text message indicating my agreement.  As you might imagine, this message created a knot of anxiety within me, and yet, unsure of what else to do under the circumstances, and thinking my cheerleader must be on board with it, I agreed to comply and sent Andrea a text reply telling her that I would do so.
That evening, when I arrived home, I tried to see if my cheerleader’s eyes revealed anything about what she may be thinking.  But there was nothing.  As she had the previous three evenings, she had a nice meal waiting and she told me to go shower and change.  I was becoming more accepting, or comfortable at least, about coming home and immediately becoming feminine at the request of my cheerleader, especially gien how the previous evenings had gone.  When I got downstairs she had poured me a glass of wine.  I sat at the counter as she finished preparing our meal.  Our conversation was pretty normal, discussing our day and such.  She had worked that day for a few hours in the morning.  After we sat down to eat, she casually mentioned that she had gone to lunch with Randall.  She told me that he and Andrea were planning to come over for dinner the next night.  Her telling me this was really not surprising, as I’d fully expected that they would be coming over for dinner over the weekend.  Then, she seemed to hesitate for a moment, and then, looking down at her plate, she said, “Randall asked me to do something for him.”  She paused, as if waiting for me to ask her what, thus prompting her to continue.  And so, suspecting that we were reaching the point Andrea had prepped me for, I asked, “Really?  What?”  She seemed almost embarrassed as she replied, “He, uh, wants me to, uh, shave for him.”  I was trying to process what she said, certain that I had not misunderstood her, and although I knew what she meant, and I had been, sort of, pre-warned by Andrea, I would never guessed that this was what she referred to.  At first, I was unable to speak, but then she added, “You know.  Down there.”  She then looked up at me, almost expectantly.  In that brief moment when she caught my eye I wondered, did she know that Andrea had forewarned me?  Did she know what I was about to say?  I couldn’t tell from her expression.  But when I spoke the words, “I want to do it for you,” it was apparent to me from her expression that she was surprised at my response, and that she was not in on the instructions Andrea had given to me.   “You do?!” she asked.  Did I?  Honestly, I was confused about how I felt.  I only knew that I was following Andrea’s guidance.  And so I assured her that I did.  My cheerleader hesitated for a few moments and then said, “Okay.  That might me nice.”
And so it was agreed.  I was going to shave my cheerleader’s pussy for Randall.  We were quiet for the rest of dinner, each of us obviously thinking about what we were about to do.  I believe my cheerleader was as anxious about it as I was.  The thought in my brain, that I was going to shave my cheerleader’s pussy smooth at the request of another man – no – a man – and then he was going to fuck her like that the next night, would not go away.  After, of course, my thought entailed, I sucked his cock to prepare him for her.  As I sat considering it, I could not believe the erection I felt growing inside of my panties.  When we finished dinner, my cheerleader excused herself, asking me to clean the dishes, as I had the previous evenings.  She was going to go upstairs to take a bath.  She said she would get things organized for me. 
After I finished the dishes I went upstairs and found my cheerleader lying back in the tub soaking, her naked body looking sexy beneath the water.  On the edge of the tub I saw a comb, a pair of scissors, a razor, and shaving cream.  She looked toward me as I walked into the bathroom, her sissy husband wearing a sexy pink nightgown, about to do a most intimate thing for her at the request of her lover.  I didn’t know how to begin.  I was so nervous.  But, thankfully, my cheerleader seemed equally nervous.  She smiled a shy smile at me and said, “I don’t suppose you’ve ever done this before.”  I don’t know why, but that made me laugh, and she did too.  I answered, “No.  I haven’t.  Have you?”  We each laughed as she assured me that she never had.  The laughter made us each relax a bit and so I just told her that I’d be careful and figure it out as we went. 
I kneeled beside the tub and began slowly, methodically, and very carefully, trimming her pussy.  Using the comb, I raised sections of her full bush and cut it until it was fairly short all around.  I then filled a hand with shave cream and began coating her.  When I did so, my cheerleader told me that she want to leave a “landing strip” for Randall.  That was the first mention of his name since I’d begun, serving as an uncomfortable reminder that I was doing this for him.  And yes, I knew what a “landing strip” was.  I very, very carefully began shaving my cheerleader’s pubic hair off of her pussy.  I removed most of it with gentle strokes, leaving only stubble.  Then, after rinsing her, I applied more shave cream and completed the job, shaving her until she was completely bare and smooth, except for a very narrow strip of hair that pointed to the entrance of her pussy, almost like a road sign directing the way for Randall.  How can I possibly explain how this felt to me?  I knew that I was shaving my cheerleader for a man, and yet, I was enthralled by committing such a personal, erotic and sensuous act for her.  At some point, I recall, I was intently focused upon the task, and yet, I could feel her watching me.  I could feel her love as she watched me do this thing for her - this thing that she was doing for another - but that I was doing for her.
The task completed, she asked me if I liked it.  I didn’t even know what to say.  I had not even thought about whether I liked it.  Oddly, what I’d thought about was that I enjoyed doing it for her.  I knew, though, that any answer, other than that I liked it, was the wrong answer.  And so I told her I did.  My cheerleader told me she was going to rinse and get out.  She told me to go wait for her in our bed.  As I went to bed I wondered if we would make love again that night.  I received my answer soon.  When my cheerleader joined me in bed she was naked.  She slipped the covers over her, as if to hide her bare pussy, and immediately pushed me down to taste her.  I had never touched a shaved pussy before.  What can I say other than that my first reaction was that it felt amazing!  My cheerleader felt smooth and slick.  The connection I felt was more intimate than I could have imagined it would be.  And judging from her response, I’d say it must have been an exhilarating sensation for her as well.  Within minutes she was literally writhing beneath me and before long she was encouraging me to fuck her, as if she simply had to have me.  Needless to say, I was thrilled at her reaction.  At that moment, the last thought on my mind was that my cheerleader had let me shave her pussy at the request of her lover.  All there was my cheerleader, and me.  I was in heaven.  Sliding in and out of her smooth pussy was an incredible experience.  She was so wet and slick.  I’d never considered that her pussy could feel so differently shaved.  I regretted not doing it sooner, although I doubt she’d have gone for it if I’d suggested it.
After I came inside of her, she pushed my head down between her thighs to clean her.  Even this act, the sucking and licking of my sperm was enhanced by her pussy being so smooth.  Even doing this, I wasn’t thinking that I would soon be cleaning Randall’s cum out of her.  All I thought about was how great it was to be experiencing this intimacy with my cheerleader.  She seemed to completely accept me as the feminine creature occupying my soul, and I was more deeply in love with her than I could ever have imagined being.  There was nothing I would not do for her, and if all she wanted was to have a man please her from time to time, I was happy to permit that pleasure to her.  After she was clean, I snuggled up to her and she whispered, “I love you so much.  Thank you for that.”  I was feeling all tingly inside and told her that I loved her more than anything in the world.  She assured me that she knew that I did.  We fell asleep in each other’s arms, me feeling more content than I could ever recall feeling, completely oblivious to what awaited me in less than 24 hours.  The week had been one of the most amazing weeks of our marriage.  But for me, it was about to take a sudden turn that I never could have imagined or predicted.
The next morning, as I dressed for work, my cheerleader watching me, she threw me a curve ball.  She asked if I thought Randall would like how it felt.  She didn’t need to be more specific either.  I knew exactly what she meant.  I was caught so off guard by her raising the question that I couldn’t speak.  Then she smiled and said, “I know.  He’ll like it too,” clearly referring to my reaction the night before.  And so, with just a few words, my cheerleader changed my mindset completely.  I went from feeling great about how things were, to being full of anxiety about where things were heading.  The previous weekend had been difficult for me, and yet somehow I’d survived it.  How do I explain this?  Before the previous weekend, I was living in a feminine, sissy fantasy world.  I was pretending to suck cock to turn my cheerleader and me on.  I was pretending, as a way to spice up our sex life, that different men we knew were fucking my cheerleader.  And she had joined me in that fantasy.  But, everything before the previous weekend, had been just that - fantasy.  The previous weekend changed everything.  Just like that, I’d had to swallow reality, and I still was not certain how I felt about the direction we were heading.  And yet, the past week with my cheerleader had been so incredible that I was not even bothered that I’d shaved her pussy at the request of her lover.  In a single question, my cheerleader brought it all back home to me by reminding me that she’d done it – that I’d done it – for Randall.  Suddenly, I felt sick to my stomach.  It was not the best way to begin the day.
I had not been at work more than an hour when I received a text message from Andrea.  The message told me that I needed to leave work early and to meet her at my house early that afternoon.  I asked her why and she told me that my place was not to question her, but to adjust my plans to meet her as requested.  I was a mess already because of what my cheerleader had said to me before I left for work.  Still, I told her that I could do it and agreed to meet her at 1:00 p.m. at my house.  And that was that.  So, I hung up, wondering what in the world Andrea could want to discuss with me that we had to meet at my house that afternoon.
I’m a supervisor at my office, so I only had to let another supervisor know that I had to leave early, explaining that something came up at home and I needed to go.  My stomach was in knots as I drove home to meet Andrea.  I arrived before she did.  I was anxious and nervous about why she insisted on our meeting.  Intuitively, I knew it could not possibly be a good thing for me.  When she arrived she was pulling a carry-on style suitcase.  She seemed to examine me closely as I greeted her and invited her inside.  I offered her a drink and she wanted iced tea, so I poured each of us a glass.  I was waiting expectantly for Andrea to reveal her purpose, but she seemed in no particular hurry.  Finally, she asked me how things went the previous evening.  I did not know what she knew, and was embarrassed to discuss what happened.  As I hesitated, Andrea let me know that she was aware that my cheerleader was now very smooth and that I had apparently enjoyed the result.  I was embarrassed to learn that my cheerleader had shared our intimacy with Andrea.  I had assumed that our private moments were between my cheerleader and me.
Seeing my obvious discomfort, Andrea assured me that everything she was doing was for my own good, reiterating to me that I needed to trust her.  She added that my cheerleader had expressed some uncertainty as well, but that she was fully on board with what Andrea was doing.  All of this sounded very scary to me at this point.  Let me add here, that I no longer feel the same way, but when events were unfolding, I was quite concerned that I was losing all control, which, as it turned out, I was.  I finally got up the nerve to ask Andrea why we were meeting.  She explained to me, in a very matter of fact manner, that she was there to "prepare" me for the evening.  I didn't understand, and asked what she meant.  That's when she stood and told me to follow her.  Pulling her suitcase behind her, Andrea led me upstairs to my bedroom.
Andrea went directly to the chair she had laid claim to the previous weekend and sat down.  She told me to come to her and then she told me to undress for her.  I did not want to undress for Andrea, especially knowing that I would reveal to her what I wore under my business suit.  It was then that Andrea basically gave me a "facts of life" talk.  She first explained that she already knew I was wearing lingerie beneath my suit.  She confirmed my suspicion that my cheerleader and Andrea had been talking regularly the entire week.  Next, as if to emphasize where things currently stood, she reprised the past week, including the details of the previous weekend when I submitted to my first living cock.  Thus, she pointed out to me, the question was no longer whether I was going to move forward with my submissive lifestyle as a sissy, but instead, how voluntarily I would proceed.  She minced no words with me.  My cheerleader had shared with Andrea that she was happy to be allowed to fuck men, such as Randall, and that she was going to trust in Andrea's guidance where I was concerned.  So, the question for me, she told me, was how much I loved my wife, and whether I was prepared to give her what she wanted.
Andrea's lecture certainly made things clearer, although it did not ease my anxiety.  The thing I knew was that I loved my cheerleader.  I wanted to please her.  And so, I finally relented, at least for that moment, and said I'd do what Andrea asked me to do.  I can still recall the smile she revealed in that moment, as I seemed to accept my fate, almost as if she always knew that I would do so.  And so, I began removing my outer clothing while Andrea watched me.  Make no mistake, I still felt completely self-conscious about doing so, but I was becoming more comfortable with her.  As I stood before her in my slip, panties, garter belt and stockings, Andrea seemed to be forming an assessment of me.  She then stood, as if a decision had been made, and told me to remove all of my clothing and to join her in the bathroom.  Each successive step, it seemed, required me to submit myself to additional indignity, and yet, I did as she asked of me. 
When I entered the bathroom, Andrea was laying out a sheet of plastic on the floor, and I could see in her hand a pair of electric barber's sheers.  Believe me, I knew what was up, but I was frozen in place, hoping against hope that I was wrong.  I still recall her words, as I hesitated coming closer - "Stop testing me Sissy.  I will not tolerate a hairy sissy.  You will be smooth for your wife.  Now get over here!"  She actually frightened me, and so I stepped forward and onto the sheet of plastic.  Once there, she told me to raise my arms above my head and she began sheering my body hair, beginning at my armpits, working down my chest (not much there) and then to my legs.  She did not shave me bare however.  She simply removed the bulk of the hair.  When she was done she told me to fill our tub with warm water and to soak.  After I was in the tub for a while she began, area by area, covering me with shave cream and shaved me smooth.  The only thing left unshaven was my male area, but that was not to last.  After I was made hairless all over, another sensation I had fantasized about, but never experienced, she told me to dry off and resume my position on the sheet of plastic.  Andrea then performed the final hair removal.  As she did so, she talked about me shaving my cheerleader the night before.  She asked if I thought she would be as turned on by me being shaved as I had been about her.  I considered the question, but actually, I did not think she would be.  In fact, I feared she would be put off by it.  Andrea handled me very carefully, and it seemed to me that she had done this before.  Then, as she finished, she said, "I think I'll leave a 'landing strip' also," referring to what I'd done for my cheerleader.  She really did seem to know everything.
After she finished I rinsed off in the shower.  When I exited, after drying off, Andrea was waiting for me with a sheer nylon robe that she draped over me.  Directing me to sit in my cheerleader's makeup chair, Andrea began working on me, basically, giving me a makeover.  She painted my toenails pink and applied fake nails onto my fingers and painted them pink also.  I was mortified thinking of how my cheerleader would react upon seeing me completely made up.  And yet, if I'm honest about it, I was very excited as well.  This was a first for me – having a woman attend to me and apply her skill to my feminizing my face.  As she worked a bit of magic upon me, Andrea talked to me.  She told me that I was really quite pretty, and that she wondered if it was even possible for someone such as me to avoid his true nature.  It felt odd, listening to her, because on a very deep, intuitive - almost intellectual level even – what she said was how I'd always felt.  I may have been born male.  And in many, many ways, I was a male.  But in the realm of emotional response, I was a woman.  And yet, I never foresaw a sex change for me.  The result seemed to lead, inevitably, to me being a sissy.  The problem with being a sissy, however, was the acceptance issue.  What woman would accept me as a sissy?  It seemed Andrea did.  But then, she was performing a job.  What about my cheerleader?  Was she coming around to accept me as a sissy?  Or, was she more drawn to sex with a man?  I didn't know the answer to my questions.  And I was terrified at how she might react when she saw me made up so effeminately.  My anxiety was at an all-time high.
My face, when Andrea was through, looked more feminine than I could ever have imagined.  Andrea led me to our bedroom and went back into her suitcase.  She withdrew a pink satin corset, complete with garter straps, and held it up for me to see.  "What do you think Sissy?" she asked smiling.  All I could think was how my cheerleader (not to mention Randall) would react upon seeing me wearing a corset.  Andrea didn't press me for a response though.  Instead, she told me face the bed and to hold onto the bedpost.  And thus began my first experience being laced up in a corset.  I've read descriptions about how painful being laced up feels.  But I disagree.  I immediately loved the secure sensation from being corseted.  Once Andrea was satisfied with the tightness of the corset, she revealed a matching bra to contain my breast forms, and helped me strap it on.  She smiled pleasantly as she worked, clearly pleased with her handiwork.  I even found myself relaxing under her care.  She assisted me in slipping a pair of black silk stockings onto my freshly shaved legs.  I cannot begin to describe how incredible it felt to be wearing stockings over smooth legs.  Finally, she slipped my feet into my black high heels.  Andrea stepped back to admire her work and declared, "You are a beautiful sissy!"  I actually felt myself blush.
Andrea also came prepared with jewelry.  She attached a pair of pearl clip-on earrings to my ears, and then adorned my neck and wrists with a pearl necklace and tennis bracelet.  She was completely feminizing me for the evening.  I was already wondering about what sort of dress she had for me to wear when she sat down in her chair and told me to kneel before her.  I hesitated for a second, but not much more, as Andrea gave me a stern look that let me know she meant business.  Once on my knees, Andrea began explaining to me that my role for the evening was to be as subservient as I needed to be to my cheerleader and to Randall.  She told me that, as my cheerleader's sissy, my goal was to make her, and whoever she was with (I noted her emphasis on, 'whoever she was with,’) feel comfortable so that they could enjoy each other's company.  She made me acknowledge that I understood her instructions.  And then came the coup da grace.  Believe me, I did not see this coming.  Andrea opened her thighs, revealing her pussy, also shaved.  She told me to masturbate for her.  You would think that I might have been beyond shockable by this point, but I wasn't.  I was stunned!  But Andrea was not kidding around.  She gave me a moment to process her command, and then restated it.  She told me she wanted me to cum into my palm and to swallow everything.  She told me to imagine myself fucking my cheerleader this past week, and to recall all of the wonderful orgasms I'd had.  Fuck!  She knew everything we'd done!  She touched herself and told me to picture myself between her thighs licking her pussy.  I began jacking off, finding myself extremely turned on by Andrea's erotic words.  Within minutes I was spewing into my hand, as ordered, and then she encouraged me to do as she'd said - to lick the goo out of my hand. When I finished she said, "Good sissy.  Now you're ready," and she held up a cock cage for me to see.  My eyes must have been the size of quarters.  She wasn't!  But yes, she was.  And despite my fear and initial resistance, she did.  And so, for the first time ever, I was locked in chastity, and I really had no clue precisely what it meant for my future. 
After she snapped the lock closed, Andrea stood and told me to follow her.  I was to begin preparing food for my cheerleader and Randall.  I questioned her as to whether I would be wearing anything else.  Surely she did not intend for me to wear only the corset, bra, heels and hose, leaving my caged penis on display as it was?  However, that is precisely what she intended.  I began shaking, thinking of my cheerleader's reaction to seeing me this way in front of a man.  I was afraid she would be repulsed at the sight.  But Andrea was insistent that I was to follow her and that I would be wearing nothing else.
The memory of the early part of the week, the part of the week when my cheerleader and I had shared such incredible intimacy, was vanquished.  I emphasize again - I do not feel now about things as I felt then.  Nonetheless, in that moment, I was a mess.  And yet, Andrea, in her unique manner, was able to pull me forward, convincing me that what was to occur, needed to occur.  Together, we set about organizing for the evening.  With Andrea's guidance, I managed to put together heavy hors d'oeuvres (there was not going to be dinner) to serve to my cheerleader and Randall when they arrived.  By this time, it was late in the afternoon.  I was expecting my cheerleader home from work at any time. 
At around five o'clock, I heard a key in the door and my cheerleader walked in.  When she saw me, dressed as I was, she stopped dead in her tracks.  I don't know if Andrea had specifically told her what she should expect, or whether it was a complete surprise to her, but she looked like she did not anticipate finding her husband looking as feminine and sissified as I looked.  Her hand went to her mouth and in a voice filled with astonishment, she whispered, "Oh my God!"  As for me, there were no words until Andrea poked me, reminding me of what she'd told me to say.  "Hi honey!  Welcome home!" I greeted her.  My cheerleader just stood there, taking me in.  Then, slowly, almost timidly, she walked toward me and touched me on the cheek.  She leaned close to me and kissed me.  Softly.  Tenderly.  "Wow!  You look amazing!" she said to me.  "Just amazing!"  I whispered a timid, “Thank you,” and offered to get her a drink.  She declined, saying she needed to shower and dress for Randall, reminding me what the evening was really about for her.  As Andrea had earlier instructed me to do, I asked if she wanted any assistance.  She declined, but I think it was more because she was in shock over seeing me dressed as I was, as opposed to not wanting any help.
My cheerleader left Andrea and me to go upstairs and get ready for what was sounding more and more like a date for my cheerleader.  When she left the room, Andrea said to me, "Was that so bad?"  I just looked at her.  Couldn't she see it?  My cheerleader's eyes?  I was not the same person to her as I'd been only a few weeks before.  I was her feminized, sissy, cuckold husband.  She was more excited about the man coming to visit than she was to see me dressed as a sissy, my bare penis on public display in a cock cage.  And my reply was not met with any disagreement.  "She sees a sissy.  That's all."  "That's right," she said.  "Because that's what you are sweetie."
Andrea asked me to fix her a drink.  She was going to sit in the den.  It seemed that she was through "prepping" me for the evening.  I was, more or less, expected to assume my subservient role for the evening.  I made a Whiskey Sour for Andrea and delivered it to her.  Just then, the front doorbell rang, and I froze.  It was Randall.  I knew what this meant.  I didn't want to, but realized I had no choice.  I had to go let him in.
I slowly opened the door, taking care to remain out of view of the street, in case there were any random passersby.  I greeted Randall and surprisingly, he didn't seem a bit phased upon seeing me dressed as I was.  Carrying a small, gift-wrapped package, he entered and said, “Hi,” in a calm and friendly manor.  "Good to see you Sissy.  You look nice."  Seriously!  He complimented me on my looks, without seeming the least bit like it was weird for a guy to be dressed as I was.  Flustered by the exchange, I thanked him.  I then told him my cheerleader was getting dressed and asked if he would like a drink.  He said he would and walked into the den and greeted Andrea like they were old and close friends, which they were.  I served Randall his usual, Maker’s Mark on the rocks, and asked Andrea how she was doing with her drink.  She said she was fine and directed me to stand next to her.  And so, while Andrea and Randall casually chatted, almost as if I were not in the room, I stood by feeling, essentially, naked.
In a few minutes, I heard steps on our stairway.  My cheerleader was coming down.  No matter how difficult each moment I'd had to endure so far was, each additional one seemed even worse.  Here I was, in my own den, dressed only in a bra, corset, stockings and high heels, my shaved penis locked up, but on display, as my cheerleader came in to greet her man in front of me.  I wondered how much more I could tolerate.  I saw her a split second before anyone else could.  I did not have enough time to process how she was dressed, which I would describe as "just barely."  She was wearing a light blue dress that was very short, and very tight, and really showed off her gorgeous shape.  Randall lit up the moment he saw her and she greeted him warmly, immediately going to him and kissing him full on the mouth, lingering on him as she let her arms drape around his neck.  I noticed Randall place his hands right on her ass, squeezing her as if he owned her, and I also noticed she did nothing to dispel such an assumption.  So, to recap, from my cheerleader I had received a sweet, nearly chaste, kiss on my lips, and Randall received a kiss that more than hinted that the night was going to be very special for him.  Throughout this my penis was throbbing painfully against the confines of the cock cage that Andrea had fitted to me earlier in the day.  After lingering in Randall’s arms for what seemed like forever, my cheerleader turned to me and, almost as if she were addressing a servant, asked for a glass of white wine.  I dutifully went to pour her a glass of cool white wine.  As I walked away I heard my cheerleader laugh and say, “Is that for me?”  That was all that I could hear though before I was out of earshot. 
When I returned my cheerleader was holding the package that Randall had brought in with him.  I handed her the glass of wine and then stood by, as I had been earlier.  “Look Sissy,” she said to me.  “Randall brought me a gift.”  I smiled, but said nothing.  Andrea had instructed me that I should restrict my input to the conversation unless required.  Randall told her to open her present and so my cheerleader carefully removed the ribbon and then the red wrapping paper.  It looked to me as though it had to be jewelry, and I wasn’t wrong.  It was a gold necklace with something dangling from it.  I couldn’t tell what it was at first.  Then my cheerleader held it up and looked at Randall, as if she was confused to find a small key attached to the necklace.  He said, “It’s her key,” nodding in my direction.  My cheerleader looked at me and as our eyes met it hit each of us what Randall was referring to.  He had given her the key to my chastity cage.  Andrea explained, “It’s up to you to decide when, and under what conditions, the cage is removed.”  So there it was – I was locked up and my cheerleader was in charge of my release.  I was so embarrassed to have this revealed to me in this way that I didn’t know what to do, and so I simply smiled what I’m certain must have appeared extremely forced.  My cheerleader smiled at me and said, “Well, I guess you’ll just have to be a good sissy.  Won’t you?”  I bowed my head and said, “Yes ma’am.”
The awkward feeling in the room was palpable.  Andrea, skilled as she was, broke the tension by asking me to go get the hors d'oeuvres.  I could hear quiet conversation in the den as I organized the trays to serve.  After I set everything out for them, I refreshed drinks.  Andrea then directed me to kneel by her as they carried on their conversation, my cheerleader cuddled up closely to Randall, his arm wrapped possessively around her.  They seemed so relaxed together, while I felt so uncomfortable in the situation.  The fantasies that I’d had of such circumstances occurring did not feel the same as reality turned out to feel.  That they, for the most part, acted as though I were not present, helped some, allowing me to retreat, somewhat, to my private thoughts, which were moving ahead of myself and thinking of where the evening would eventually lead.  I was asked to refill drinks a few more times as they chatted and snacked on the food I’d prepared for them.
After a while my cheerleader stood up and took Randall’s hand, and smiling seductively at him, said, “Come on.  I’m ready for bed.  And I have a surprise for you too!”  He said, “Really!”  She smiled and explained, “Me and Sissy, yes.”  And then addressing me, my cheerleader said, “Come on Sissy.  I want you to see also.”  And so we all walked out of the room together, my psyche torn with the anxiety of what I knew was to come, also mentally preparing myself to suck cock again, for that was what I expected.  It turned out that I was wrong in that regard – at least as to how I thought it would be. 
When we got upstairs Andrea assumed her seat and led me to kneel beside her.  It was as though she were my guide for the evening.  I began to wonder how much of what was occurring she had coached my cheerleader and Randall on before we the evening began.  My cheerleader certainly seemed to know what her aim was.  She wasted no time in undressing Randall, hungrily removing his clothing until he was naked.  She teasingly pushed him gently backward and onto the bed.  Then, she slowly lifted her tight dress over her head, pulling it off and tossing it on the floor.  She stood before us all wearing only a thin sheer bra and matching panties.  And that was when I noticed it for the first time, as it appeared that Randall did as well.  My cheerleader’s freshly shaved pussy, or cameltoe, as it more properly should be described, was prominently outlined by the thin sheer panties that clung to her puffy, damp, pussy lips.  Only the thin dark patch of pubes that made up her landing strip showed above.  Reaching behind her, she unclasped her bra, and let it fall to the floor.  Honestly, I had never seen my cheerleader behave quite this way.  And the weird thing was, she wasn’t doing it solely for Randall.  I think part of her little show was intended for me.  She was basically forcing me to sit by submissively watching her give herself to a man.  Then, she slowly slid her panties off and to the floor, revealing her smoothly shaved pussy for Randall to see.
“Do you like?” she teased.  Grinning broadly he said, “Yeah!  I like!”  “I’m glad.  Sissy shaved me for you,” she told him, which didn’t make me feel better about myself.  Randall looked at me and said, “Well thank you Sissy.”  I felt small, weak and insignificant at that moment, but whispered, “You’re welcome.”  My cheerleader then climbed up on the bed on her hands and knees, crawled toward Randall, and took his rock hard cock in her hand and began playing with him, smiling sexily the entire time.  I found myself wondering if I was going to be asked to prepare him for her, as I had the week before, but it seemed as though my cheerleader was going to do it herself this time.  And that did not make me feel better either.  Was I going to be forced to simply watch her seduce and then fuck Randall?  It seemed so.
My cheerleader leaned over and took him into her mouth, slowly sucking him deeply, moaning as she sucked his cock, seemingly oblivious to Andrea and me sitting by the bed watching them.  I’d never seen her this eager sucking my cock.  I mean, my cheerleader had sucked mine.  Many times.  And she did enjoy it.  At least, I thought she had.  But it was nothing like what I was witnessing this night.  With one hand wrapped around his thick base, and using the moisture from her saliva, my cheerleader was working Randall’s cock and sucking him like a pornstar, telling him between releases of her mouth how much she loved his big cock, how much she wanted his cock inside of her pussy.  I was in the worst pain, mentally and physically, because my own cock was pounding incessantly against the chastity cage.  I think even Andrea was affected by what was happening.
After several minutes of sucking Randall’s cock, my cheerleader finally couldn’t take it anymore.  She climbed on top of his cock, letting it slide into her wet, eager, smoothly shaved pussy.  I watched as she slowly sank down on him, his girth spreading her lips wide open, swallowing him inside of her.  I don’t know that I’d ever seen anything so erotic as watching my cheerleader consume Randall’s cock that night.  She was clearly in ecstasy.  It was so obvious how much pleasure she was experiencing.  And although I was not directly responsible for her eventual orgasm, I think she was getting off, in part, on doing it while I watched helplessly from the side.  As she fucked him harder, I could tell she was having multiple orgasms and that Randall was loving fucking my cheerleader.  And then it happened.  The moment when he had his orgasm.  He began bucking up toward her, stopping for a moment, and then fucking her again, then stopping, each thrust releasing another blast of his sperm inside of my cheerleader.  And here is the most difficult part for me to admit.  What I wanted in that moment, more than anything, was to crawl between my cheerleader’s thighs and begin sucking his cum out of her.  I was almost praying that I would be given that opportunity.  My cheerleader collapsed onto Randall’s chest, breathing heavily, his cock still inside of her, thanking him over and over again for what he’d just done to her. 
Andrea and I sat quietly by as they came down from their effort.  My cheerleader turned toward me, her head resting on Randall’s chest, and smiled sweetly, even lovingly at me, and whispered, “Thank you sweetie.  I love you,” and I melted.  What were these emotions running through me?  I had just watched my cheerleader fuck a man like he was the most precious thing on earth to her.  And my most nagging reaction was that I wanted to lick her clean, and then, she tells me that she loves me, and I want to do anything she asks of me.  “I love you too,” I answered from my knees beside our bed.
After a few more minutes passed, and my cheerleader had caught her breath, she said to me, “Come on Sissy.  It’s your time now.”  And I knew what she meant.  I gave no thought about to I was dressed – no thought about what a sissy I looked like next to her man.  No.  All I thought then was that I was going to be permitted some intimacy with my cheerleader.  In that moment, I needed it desperately.  As I stood, Andrea whispered in my ear, “Good girl,” and I actually did feel a sense of pride that I had pleased her.
As I climbed onto the bed, Randall’s cock remained partially inside of my cheerleader.  His sperm was drooling out of her and dripping down the side of his still engorged cock.  My cheerleader leaned backward, supporting herself with her arms stretched behind her, presenting her pussy to me, Randall’s cock keeping her lips stretched wide, their juices comingled together and waiting for my sissy tongue and mouth to clean them off.  With no hesitation – driven by my own urgent need to please them – I bent down and began licking them where they were coupled, right at my cheerleader’s opening, circling my tongue around her enflamed lips and Randall’s thick cock.  There was a lot of sperm leaking out of her.  And as I licked them, I suddenly realized that Randall was growing larger.  He was getting harder!  I was bringing him back to readiness!  Already!  He was ready to fuck my cheerleader again!  My cheerleader felt it too and exclaimed, “Oh fuck!  Yes Sissy!  Yes!  Don’t stop!  Fuck me Randall!  Fuck me!”  And so he began fucking her again while I was licking their junction.  I could never have imagined doing such a thing, but I was, and I was consumed in the act, being so close to my cheerleader as a man fucked her for the second time in less than fifteen minutes.  It seemed that Randall could go forever - especially this second time.  He was pushing in and out of my cheerleader, my mouth working feverishly to keep up, tasting their cum mixture as he brought her to another orgasm.  As I maintained my position at my cheerleader’s pussy, licking and sucking them, I could feel Randall ejaculating inside of her, his seed filling my cheerleader.  I could not believe what I was experiencing.  To this day, that moment is one I can recall with such vivid memory that it is as though it is actually recurring again.  It also may have been the moment that I realized that I would do anything for my cheerleader – anything! - and that I really was a sissy, and not merely in my fantasy mind.
My cheerleader had been watching me intently as I licked and sucked her while she had sexual intercourse with Randall.  I glanced at her and tried to decipher her expression.  While she seemed excited and aroused, I thought I saw confusion in her eyes as well.  What was it?  Was it me?  Or, was it her?  Or both?  No matter, there had been a change in my cheerleader.  It became noticeable after we moved from the fantasy of her being fucked by someone other than me, to her actually experiencing a man's cock inside of her.  It almost seemed that my cuckolding was a liberating event for her.  She had seemed so uncomfortable when she learned of my feminine proclivity way back when.  She had slowly accepted me more and more, allowing it to become a part of our lovemaking.  But, was there something missing for her?  The feeling of having a man touch her?  Not that she stopped loving me - that me acquiescing to her need for a man gave her that missing thing - permitting her to continue to love and, even, accept me as a sissy?  I couldn't tell, but I remember vividly having these thoughts as she watched me ministering to her and Randall.
Randall's cock, covered in thick cum, slowly slipped out of my cheerleader.  The sight of her pussy closing as he withdrew, his sperm dripping from her hairless pussy, was such an erotic sight for me.  As he fell free, without instruction, I took him in my mouth, hungry for his taste.  I cleaned him thoroughly.  His cockhead was continuing to leak thick cum, and I swallowed it all.  My cheerleader moved to his side, cuddling, watching me, mesmerized at my eagerness to satisfy Randall.  
When I finished cleaning Randall, I turned my attention to her, and could feel her body reacting to my tongue as I licked her cum covered slit, pressing herself upward, silently urging me deeper.  The pain I felt from my own penis was intense.  And yet, it only seemed to drive me more to please my cheerleader.
When I finally cleaned all that I could of Randall's cum from her, my cheerleader thanked me.  She also told me she loved me.  That was all I needed.  Hearing her express her love for me in front of Randall and Andrea made me feel as though, despite the humiliation I was experiencing by submitting as I had, I was of value to my cheerleader.  That was the only thing that mattered to me.  On the other hand, she was snuggled up close to Randall, and I suddenly felt awkward - out of place - on the bed with them.  As if sensing the same thing, Andrea took control, telling me to come with her.  She stood and we left my cheerleader and Randall alone.  I supposed he was staying, and Andrea confirmed when she told them goodnight and closed the door behind us.  
Andrea led me to one of our guest rooms just down the hall.  It seemed Andrea was also staying the night.  Turned my back to her, she told me to remove my stockings, and then she began unfastening my corset.  She told me get in the bed and she left me there.  I could hear her using the restroom, and was wondering if she was going to sleep in the other guest room when the door to the room opened and Andrea rejoined me, this time nude.  I was stunned - at her beautiful body and that she was joining me in bed.  I had not anticipated this.
Andrea crawled in beside me, positioning my back toward her breasts, and held me closely.  She whispered in my ear that I had performed well this night, telling me that I was one of the most natural sissies she had ever worked with.  I don't know how to explain my reaction to what she was saying to me.  As I've mentioned, I don't feel now as did at the time these events were occurring.  But then, I was torn between feeling proud to hear her commending me, to feeling a complete loss of my remaining manhood because I had so easily been led to do what I'd done.  I wanted to say to her that I'd had no choice, so that I would not be truly responsible for letting my cheerleader be taken by a man, or for sucking his cock as eagerly as I had.  But I've never been a person who resisted accepting responsibility for my actions.  Thus, deep within me, I knew.  I knew I was the one who let everything happen - who did it all.  I was a sissy, and there was no escaping it now.  The only question lingering for me was my cheerleader.  She was in our bedroom with a man - a man I had just watched her basically consume with a voracious sexual, appetite.  And while I thought I could continue to allow her that, I worried about us.  I couldn't bear to lose what we had.  Our love.  Our closeness.  I'd never made love to another woman.  She was my first, and I still wonder if, were it not for her, if I ever would have made love to a woman. 
I was uncomfortable feeling Andrea’s naked body pressing against me.  Holding me.  Did it feel good?  Yes.  It did.  But, despite my acquiescence in my cheerleader giving herself to Randall, I did not feel a corresponding right to be with another woman in this way.  Somehow it seemed like I should comply with a different set of rules.  Nonetheless, my penis was pounding inside of the plexiglass cage to which my cheerleader possessed the key.  When Andrea reached over my waist and cupped my freshly shaved ballsack in her soft hand, gently stroking and kneading me, I was unsure how to respond.  The simultaneous pleasure of her touch and the continued throbbing that resulted from my restricted effort to attain a full erection were conflicting responses.  Andrea shifted position, pushing me downward toward her waist.  I actually resisted her, feeling that it simply was wrong for me to do for her what I could tell she wanted from me.  But she was insistent.  She told me not to worry.  That it was okay.  She told me my cheerleader did not mind, hinting that she had prior approval.  As if to provide me a bit more justification, she added that my cheerleader probably had Randall's cock inside of her at that very moment.  And so, another first occurred for me that night.  I pleasured a woman other than my cheerleader.  With my mouth, of course.  Still, the experience of tasting another woman's pussy was not something I would have thought I would ever do, and I wondered if this would become a regular thing.  At the time, I did not know that Andrea would only be a part of our lives for a short time.  It seemed to me then that she was becoming a regular part of our lives.  As I became engrossed in pleasing her, Andrea coaxed me onward, encouraging me, repeatedly calling me a "sweet sissy," even revealing to me that my cheerleader had told her I was good at licking a pussy, so that I learned how much of our intimacies the two women had shared.  I licked and sucked Andrea through several orgasms that night.  Thus, everyone in my house, except me, received sexual release.  After I'd satisfied Andrea she held me closely again, consoling me as the weight of an emotionally exhausting day finally succumbed to sleep.
Andrea woke me the next morning, telling me to shower, as she needed to help me get ready for the day.  The previous weekend my cheerleader and I had been left alone on the following Saturday.  It appeared that might not be the case this weekend and I became anxious about what Andrea meant by getting me "ready for the day."  After my shower, during which Andrea told me to shave my legs and underarms again, she supervised my dressing in clothes she had brought with her.  What she dressed me in, while covering me more than the night before, was no less humiliating for me to wear in front of my cheerleader and her man.  First, she had me put on a pair of tight, control panties, insisting that I tuck my caged penis between my thighs, thus creating a frontal profile with no bulge showing.  Over those I put on a pair of nude pantyhose.  And finally, I was given a tight pair of red, lycra short shorts that just looked so so sissy.  My breast forms were held in place by the same pink bra I'd worn the night before, but I was also given a skin tight, pink nylon top.  The outfit was completed with my black high heels.  After fresh makeup was applied, the person I saw in the mirror was no man.  To the contrary, Andrea had managed to make me look even more feminine than I had been the night before.
Andrea sent me downstairs to make coffee and to prepare breakfast for everyone while she showered and dressed.  She told me to deliver coffee to my cheerleader and Randall in their bedroom.  I was not looking forward to doing so.  Nonetheless, I’d gone this far and knew that resistance would likely ruin things for my cheerleader, and I simply could not bring myself to doing that.  I’d seen how happy she was the night before.  I was doing this for her more than anything now.  After loading a tray with cups, cream, sugar and coffee, I made my way upstairs to my bedroom.  I rapped lightly on the door before entering, to make sure I did not interrupt them in the middle of anything.  My cheerleader called out, “Come in,” and I opened the door and stepped inside, preparing myself for their reaction to seeing me dressed as such a sissy.
Randall was sitting up against the headboard, relaxing as my cheerleader’s head lay near his waist, her hand holding his large, thick, semi-soft cock, her lips and tongue kissing and tasting him, holding him as if he were gold.  She smiled at me and said, “Good morning.”  I returned her greeting and asked if they would like coffee.  Randall said yes, but my cheerleader said, “In a moment.  I’m busy right now,” as if I couldn’t see that.  From the moment I walked in the room and found my cheerleader savoring Randall’s cock, she locked her eyes on mine, holding my gaze as she flaunted him in my face.  I don’t think she was doing it to be mean though.  I think she was simply feeling so comfortable with my silent agreement that she could have his cock – that I was her cuckold – that she didn’t completely assess the level of pain I felt watching her so intimately engaged with Randall.
I poured Randall his coffee, adding cream as he’d requested.  I handed him his cup and he sipped it, complimenting me, continuing to enjoy my cheerleader tenderly loving his cock as I stood by the bed.  I asked if they would like some breakfast.  My cheerleader said they would come downstairs in a while, but that I could go for now.  She told me to leave the coffee on the nightstand.  Confused as to why I simultaneously did not want to leave them and was relieved to have been dismissed, I left them alone.  As I closed the door I heard my cheerleader giggle, like they had a private joke between them, but that was all.  Downstairs, I found Andrea in the kitchen.  She looked refreshed from her shower.  She was dressed casually in jeans and a t-shirt.  She smiled and asked if my cheerleader and Randall were awake.  I must have turned red when she asked, for she said, “Oh!  Well, then, I suppose we’ll wait on breakfast.”  I looked in the refrigerator and found some fruit and bagels that I could prepare.  I set about keeping busy and getting things organized.
Nearly an hour later, my cheerleader and Randall came downstairs.  He was showered and dressed.  My cheerleader, however, was wearing only the panties she had worn the night before and a short nylon coverlet that hung partially open.  She was showing no signs of modesty around any of us.  They greeted us good morning and my cheerleader announced that she was starving.  So I put everything out for them and everyone began eating.  Andrea, Randall and my cheerleader were engaged in small talk while I felt, more or less, like part of the background.  I felt so self-conscious about how I was dressed, doubly impacted by my cheerleader’s complete focus of her attention upon Randall, that I was more comfortable remaining quiet.
After breakfast Randall announced that he was leaving.  I felt a huge sense of relief.  As he moved to leave from our side door in the kitchen, my cheerleader went to him and put her arms around him, her coverlet falling open completely so that her full nude front pressed against him.  She kissed him on the mouth – hard - a full, wet passionate kiss.  He grabbed her panty-covered ass and pulled her firmly to his body, returning her kiss in kind.  While this goodbye kiss was taking place, I was feeling small and weak.  My cheerleader was clearly smitten with her man.  From the corner of my eye I could see that Andrea was intently watching me observe the interaction between my cheerleader and Randall, as if sizing up my reaction.  “See you next week?” my cheerleader asked when their lips parted.  Randall smiled and said, “Of course,” as if it was a given, and so I was advised that there would be a next week to be prepared for. 
My cheerleader watched Randall walk away from our house, then closed the door and returned to the kitchen.  She walked directly to me and put her arms around my neck and gave me a soft, tender kiss, holding it for a long time.  It was not a forceful kiss full of sexual desire like the one she’d given to Randall moments before.  But it was equally passionate in its own way.  Pausing, she looked deep within my eyes and said, “I love you so much baby.  I can’t tell you how much I appreciate what you’ve done for me.”  You might imagine my reaction.  I went from, only moments before, feeling like I was losing my cheerleader to a man, to grateful to have her as my wife.  She was letting me know that, despite her sexual attraction to Randall, she loved me more than anything and thanked me for, basically, giving her an amazing gift.  Melting in her embrace, I told her I loved her too.  
She kissed me sweetly again and then asked me to pour her a cup of coffee and to bring it to her in the den.  Andrea asked for a cup too and went with her.  I fixed them each a cup of coffee, and one for myself as well, and joined them in the den.  I was about to sit next to my cheerleader when she stopped me, and motioned for me to go to the floor by her.  “I have a present for you,” she said, as she let her thighs fall open.  “From Randall,” she added.  Sinking to my knees, I reached to remove her panties that I could now see were soaking wet.  But she stopped me.  “No.  Leave them on.”  Positioning myself closer to her panty-covered pussy, I leaned down to taste her.  I licked outside of her panties and could immediately taste Randall’s sperm soaking through the sheer nylon panties.  I licked some more and felt my cheerleader tense up as she responded to the sensation of my tongue licking her panty-covered slit.  “Suck me!” she commanded.  I opened my mouth wide, placed my lips over her smooth cameltoe and sucked.  A flow of thick and creamy sperm began to ooze through the nylon.  Randall’s cum was strong and overpowering, although my cheerleader’s taste was there as well.  I sucked her until she had an orgasm and her pussy was emptied of cum.  Then she let me sit by her on the couch, cuddling close to me.
As we sipped our coffee, Andrea began talking to my cheerleader and me about the past 24 hours.  She told my cheerleader that I was a natural sissy, and that she felt that we were heading in the right direction with our relationship.  My cheerleader smiled at me as she listened to Andrea sizing me up.  This conversation seemed odd and felt uncomfortable to me at the time.  But later, after I had time to process it and consider what Andrea said, I realized that something altogether different was taking place.  At the time, Andrea spoke to my cheerleader almost as though I were not in the room, although she referred to me throughout the discussion.  And I felt embarrassed and humiliated to hear her speak of me in the terms she did.  However, I don’t think that was her intent.  Andrea, it seems, was not concerned about me.  She knew what I was.  She’d met men like me before.  I was a submissive sissy – and a natural one at that.  Her concern was how my cheerleader accepted herself as a woman with strong sexual needs that required attention from a man, and how she reconciled her love for me – her sissy husband.  As I’ve mentioned, I thought as events were unfolding that Andrea was becoming a part of our lives.  But she wasn’t.  Her role was to help my cheerleader and me accept our relationship.  Between the two of us, my cheerleader actually was the one who needed guidance more so than me, because I was, by my very nature, going to submit.  Thus, as I relate this conversation that occurred that morning, understand that it while it sounded one way when it occurred, it actually was intended differently.
Andrea asked my cheerleader if she had enjoyed fucking Randall.  She hesitated, as if to spare my feelings.  That’s when Andrea told her not to concern herself with my reaction.  She told her that I was her sissy, and that I was there to please her, even if that meant watching while she received pleasure from a man.  She emphasized that she was not merely referring to Randall, but to any man my cheerleader might choose.  Again, as I listened to this, I was in emotional agony, imagining my cheerleader with even more men.  However, Andrea knew what she was saying – I was going to submit to whatever my cheerleader asked of me.  On the other hand, I could see that my cheerleader was having difficulty accepting what Andrea was saying, almost as though she were feeling guilt for considering the possibility of even more men fucking her.  Andrea, seeing the uncertainty in my cheerleader, began recounting the previous night, reminding each of us of how willingly and enthusiastically I had allowed Randall to fuck my cheerleader while my sissy mouth was pleasing them simultaneously.  What man, she asked my cheerleader, would permit his wife to do such a thing and to do what I’d done?  Only a sissy she explained.  She explained that the love between my cheerleader and me was obvious, but that did not mean my cheerleader should not accept what I was allowing her to do.  However, she also told my cheerleader that there was a duty on her part to always make sure that I understood my role.  That, she explained, was where the chastity cage came in.  She emphasized that my cheerleader had to embrace chastity as a way to control me, and as a way to keep me focused upon my role in our relationship as it was now evolving.  All of this, at the time, was like torture for me.  I also think it was difficult for my cheerleader to process.  She was obviously enjoying her new sexual freedom.  However, she was benefitting from my submission to her through Andrea’s guidance.  Andrea was attempting to emphasize the responsibility my cheerleader had, not only to me, as her sissy husband, but to our relationship as a married couple.  Such was not easy for my cheerleader.  But she was listening, and in time, she has grown in her comfort level, and as I’ll reveal in later installments, our relationship has, indeed, grown stronger.
Andrea left us alone then, telling us that she would be in touch, and would see us the following weekend.  After she left, my cheerleader and I returned to the den and sat together.  She held me gently in her arms as I felt the tension of the previous day leave my body.  Alone in my cheerleader’s arms I could feel her love for me.  We had a quiet and peaceful day together, although whenever there was any doing to be done, she asked me to do it for her.  I could sense that she was taking to heart Andrea’s guidance that she had a real responsibility to me to be in charge, something that did not come naturally to her.  But she was trying.  The next week of our life was another step forward, leading to the weekend, where I was taken another huge step forward under the care of Andrea. 
Telling about this week in my life has been both difficult and liberating for me.  I wasn’t sure I could get it written to my satisfaction.  Throughout I worried about how people who have been following my story might think of me.  And while I know that I’m putting this out on the Internet in an anonymous fashion, I still feel as though I have announced to the world that I am a sissy and that I accept my nature, which I do, albeit in the way and to the relatively few people who actually know.  I will await the responses of the world now and hope that the critics will not judge me too harshly, as I look forward to the comments from those who share my nature.

Kisses,

Leeanne