Sissy And Cheerleader Spend A Weekend Apart

[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.  These are the previous posts that tell the story about my sissy journey.]

My first full week in chastity was nearing an end.  Honestly, I don't know why I had it in my head that the next weekend would bring release.  I fully expected the upcoming weekend to be much like the previous two, with Randall spending Friday night at our house.  Nonetheless, I was hopeful that I might receive some reward (yes - I was already thinking in terms of rewards) for my good behavior and no more begging for release.  Thus, when I received a series of text messages from Andrea while at work on Thursday, my anxiety about the coming weekend spiked.  As she had the previous Thursday, Andrea explained to me that my cheerleader would be broaching a subject with me that evening.  Again, she told me, I would know it when she brought it up.  And when she did, Andrea instructed me, I was to say, "May I help you get ready?"  In my text replies with her I attempted to lure enough details to allow me to deduce what was up.  But Andrea was too skillful for that to work on her.  Reluctantly, I assured her that I would do as she told me to.  As with the previous week I was motivated, more than anything, by Andrea's hinting that this was what my cheerleader wanted.

For the rest of the day I wondered what new little twist my cheerleader was going to throw my way.  When she revealed it to me later that evening, as we watched television, I was beyond floored.  What she told me was not something I would have imagined she would be willing to do.  But, then again, the things she'd done the past two weeks were not things I would have expected from her.  We were sitting in the den watching a baseball game when she casually told me that Randall had decided not to come over the next night.  The abruptness of the news caught my attention immediately.  My first thought was that meant he'd be over Saturday, and asked if that was the case.  At that point my cheerleader became quiet, revealing her own discomfort.  "No," she told me.  "He isn't coming here at all."  I asked if something was wrong and she said no.  Then I pushed her to find out why he wasn't coming over.  How can I explain my response to the news?  Not only was I feeling a sense of disappointment, but I was actually concerned for my cheerleader.  I was under no illusions that she was not thoroughly enjoying her time with Randall.  My cheerleader's explanation, though, turned all of my internal concerns upside down.  She explained that the reason he wasn't coming to our house was because he wanted to take her away for the weekend.  Alone.  Needless to say, I was shocked.  This was not part of what I thought I had bargained for.  "Where?" I asked.  "Fort Lauderdale," she said.  The beach.  That also meant a flight since we live in D.C.  What could I say?  I was not thrilled to hear this news.  My internal anxiety began rumbling out of control.  I asked her if she was going to go.  Her response was, "I want to.”  Then, shifting it to me, she asked, “Do you mind?"  Well, yeah, of course I minded.  On the other hand, my cheerleader wanted to go.  I realized that this had to be what Andrea was referring to earlier.  Although I'd agreed to do as she instructed, faced with the significance of this event, I was reluctant.  As I considered my response, my cheerleader repeated her question to me, "Do you mind sweetie?"  I made my decision.  I loved my cheerleader.  I wanted her to be happy.  I decided to prove my love for her.  "May I help you get ready?" I asked.  Her reaction, in that moment, was worth it all.  Beaming a bright smile, she hugged me, thanked me, told me loved me, and then said, "When I get home I'm going to unlock your cage!"  So, at least she gave me something to look forward to. 

 Allowing no time for further reflection, my cheerleader stood up and took my hand.  "Let's go.  We need to pack.  Our flight leaves at 8 tomorrow morning."  Right!  Randall had already booked flights.  She was planning to go with him no matter what I'd said.  Their plans were to stay at a W Hotel overlooking the Atlantic Ocean, to return Sunday evening.  So, my cheerleader was going away with Randall, leaving me alone for the weekend.  And I was acquiescing in her desire.  Upstairs in our bedroom, my cheerleader asked me to get out her carry-on suitcase.  Then, as excited as I'd seen her in a long time, she began chattering about what to pack, soliciting input from me on each thing.  The first thing she chose was three different bikini bathing suits, presumably one for each day they were going to be there.  She asked me to pick two of her dresses for dinner Friday and Saturday, letting me know she wanted me to pick something I thought Randall would like.  As difficult as it was to do so, I chose two of her sexiest dresses.  My cheerleader approved and gave me a big kiss for being such a good husband.  She picked out a few casual outfits to wear during the day and then turned to her lingerie.  Not surprisingly, she chose some of her skimpiest and sexiest lingerie for her trip.  This was really happening and I voiced not one objection.  Sissy or not, I felt I should have resisted somewhat.  But I couldn't bring myself to deny this to my cheerleader. 

Packing complete, we went to bed, spending our last night together for the next few days.  The next day I was to drop her at the airport on my way to work.  Not only had I helped her pack for her weekend away with Randall, but I was delivering her to him as well.  My stomach was a whirlwind of turmoil as I contemplated my cheerleader being away, under totally anonymous conditions, with another man.  It would almost be as if they were husband and wife for all intents and purposes.  I hated the thought of it, but felt helpless to do anything about it.  My cheerleader kissed me goodbye at the airport, again thanking me, telling me she'd call or text while she was away.  After she disappeared into the airport, I started my car and drove to work, although I was in no condition to accomplish anything.  Shortly after I arrived Andrea sent me a text message.  "Did she get off okay?"  I replied that she did, irritated that she was throwing it in my face.  She then asked me if I had plans for the evening, as if she didn't already know that I did not.  When I confirmed it, she asked if I'd like to go to dinner.  I didn't really take her suggestion as a request - I sensed that she meant that we were going to go out to dinner.  But I also wasn't looking forward to being alone all weekend, so even spending time with Andrea was a welcome thing for me.  We agreed to meet at a D.C. restaurant after work.

Around mid-afternoon I received a text message from my cheerleader.  It consisted of a photo of her lying on a chaise lounge by a pool, wearing a sexy, red string bikini and wearing dark sunglasses.  She looked beautiful.  She was waving, presumably at me, and was holding up with one hand, for me to see, that she was wearing her necklace with the key to my chastity cage.  In the background were other bathers, including many women who all appeared to be upscale and glamorous types.  I knew the W was a trendy hotel, so I wasn't surprised.  Obviously, my cheerleader was enjoying herself.  My irritation spiked as I thought of Randall maneuvering my cheerleader away for himself like this, and was even more bothered that I felt my penis swelling in the chastity cage as I thought that thought.  Feeling as though I had to reply in some way, I texted her back, "Looks like fun.  Wish I was there."  She replied, "Hmmm.  Maybe some other time."

I worked late since I was to meet Andrea in the city.  We met at a restaurant in Georgetown.  She was sitting at the bar waiting for me.  She stepped off of her stool to greet me with a peck on the cheek.  Smiling, she said, "Hi sissy.  You look different dressed like that."  'Thanks for the reminder,' I thought.  We sat down and had a few drinks while Andrea talked a bit more freely with me than she had before.  It turns out that she and Randall had known each other for a long time.  He had invited her over to our house the first night because he had sensed that my cheerleader and I were a bit out of our element with the whole cuckolding thing.  She had quickly concluded that he was correct in his assessment.  Then, she had taken an independent liking to my cheerleader and to me.  We seemed to her like a nice couple who genuinely loved each other, but had needs that we weren't comfortable mining completely on our own.  So she decided to assist.  I was intrigued by her insight, not simply into my nature, but into my cheerleader as well.  I found myself opening up to her and sharing my inner sissy secrets.  Andrea was non-judgmental as she listened to me talk freely.  I shared much of my story that I’ve already told here on my blog.  I think she was genuinely intrigued.  We drank wine and ate dinner together until late.  When our waiter brought the check I picked it up, paid it, and then we left.  As we walked to our cars Andrea invited herself to spend the night at my house.  I hesitated, thinking that my cheerleader had not indicated consent to me spending the weekend with another woman.  Sensing my concern, Andrea explained that she and my cheerleader had agreed I should not have to spend the weekend alone.  Oh!  Besides, she added, "She's probably getting fucked as we speak, if I know Randall."  Oh!  Once again, a decision seemed to have already been made for me, and my acquiescence was not really necessary.  Since we each had our own cars, we drove separately to my house.

 As if to emphasize her conspiracy with my cheerleader, Andrea had a suitcase in her car that she let me carry inside for her.  She went to the guest room where we'd spent the night together the previous weekend, said she was going to shower, and told me to do the same, but to dress "appropriately" for bed.  I understood what she meant.  When I returned to the guest room, Andrea was in bed wearing a shiny black chemise, leaning back against propped up pillows perusing a magazine.  I wore a pink babydoll, pink panties, and a pink bra containing my breast forms.  On a whim I'd brushed mascara onto my eyelashes and added a bit of pink lipstick.  Andrea made me feel so comfortable about my sissiness that it just made sense.  She smiled when she saw me.  "Pretty."  She patted beside her, indicating I should join her on the bed.  I cuddled beside her, the pain my penis felt a sure sign of my arousal.  As we cuddled, my cell phone beeped next to me.  It was a text message from my cheerleader.  Well, it wasn’t really a text message.  The message contained a photograph of her wearing a sexy babydoll.  Andrea made me show it to her.  “Well,” she said.  “I suppose we know what they are getting ready to do.  Don’t we?”  I felt weak and helpless, seeing my cheerleader looking so sexy for the private pleasure of Randall.  But I’d agreed to let her go.  Right?  So what could I say?  “I suppose.”  Andrea kissed me softly on my lips, and then nudged me downward.  "Do your thing sissy," she said, more like an order than a request.  “Try to not think of what your wife is doing right now.”  As if I would be able to keep that thought out of my head now.  In any event, I complied, treating Andrea to all of the pleasure I could manage with my mouth.  She let me pleasure her for a long, long time, as she continued to read her magazine.  I could tell she enjoyed it.  But her manner made me feel as though I was more a tool than a lover.

We feel asleep snuggled closely.  I was relieved that I was not spending the weekend alone.  As difficult as it was to know my cheerleader was away for the weekend with a man, at least I didn’t have to pass the time alone.  The next morning Andrea woke me and told me to go shower and to shave my entire body fresh.  She wanted me to be perfectly smooth.  The thing about shaving your body is the immediate realization that you need to maintain the smoothness, because the stubble phase is really not comfortable at all.  I’d already been maintaining the smoothness from the previous weekend.  Still, I did as she asked.  By the time I finished Andrea was up and dressed - casually, wearing jeans, a white blouse and sandals.  She didn’t come out and say it, but I sensed that she had a plan for me.  She told me to put on a robe and come down for breakfast.  She had made coffee and heated some muffins my cheerleader had left in the refrigerator.  As we ate I received a text (or, again, I should say, a photo) message from my cheerleader.  Randall was obviously treating her to a special weekend.  She was receiving her breakfast in bed.  Naked.  Fuck!  I wondered if she was torturing me intentionally.

Andrea seemed to be sizing me up at every turn.  Seeing my reaction to the photo of my cheerleader she said, “Looks like a fantasy weekend for a woman.  Doesn’t it sissy?”  I reluctantly said that I supposed so.  She told me to stop acting so wimpy.  Basically, she told me that it was obvious that I enjoyed seeing my cheerleader receive the pleasure that a man could give her, and that I was equally enjoying letting my sissy side come out in such an open way.  In short, Andrea was cutting me no slack if I was going to feel sorry for myself because my cheerleader was away with another man.  And then, she told me to forget about them for a while – that I was about to experience a special sissy fantasy.

After we ate, Andrea and I went upstairs to my cheerleader’s dressing room.  Andrea sat me down in front of the mirror and began a very careful and complete makeover.  Fresh red polish on my toenails, application of press-on fingernails, also painted red, and facial makeup that exceeded anything I’d ever managed before.  Andrea checked me out when she was finished and was equally astonished at how pretty she had made me look.  She told me to wait in my bedroom while she retrieved the clothes I was going to wear.  I was stunned when she returned with a maid’s uniform.  Observing my reaction, Andrea said, “What did I say?  Every sissy’s fantasy.  Huh?”  I was, honestly, torn.  How did she know me so well?  Of course I’d fantasized such a thing.  But Andrea was making it come true in a way I had not imagined.  She had everything to make me look like a French maid.  As if I had a choice, I nonetheless submitted and let her dress me in the intricate outfit she’d brought with her.  First, she laced me into a black lace corset, pulling my waist in tightly.  She attached fishnet stockings to garter straps that hung from the corset, and then helped me step into a pair of tight black panties covered with rows of white lace, front and back.  She made me tuck my locked penis between my thighs.  The black bra was a match to the corset, the lace at the bottom edge interlocking nicely with the lace along the top of the corset.  Before she put the dress on me, she revealed another little toy she intended to introduce me to.  She had brought a stainless steel butt plug with a jeweled top, and told me to bend over.  I hesitated, but she was having none of my protestations.  She said that the plug would make sure that I felt feminine all day, and that it was going to happen, or she was done with me.  Her approach nailed me perfectly, because at the point this was happening I would have done anything to get to finish the transformation.  I would never have dreamed doing something like this in front of my cheerleader.  But Andrea was another matter.  She understood that I was a sissy, was experienced with sissies, and I just felt like I could really let go, without being judged, in front of her.  So I bent over and let Andrea pull my panties down, lube me, and then insert the plug into my butt or, as she referred to it, my pussy.  It felt so, how do I describe it?  Perfect?   Yes.  It felt like it belonged there.  Andrea explained that I would be aware of the plug with every move I made and that was the entire point.  To feel full of something.  Andrea then rewarded me by helping me don the beautiful black satin maid’s uniform she’d brought with her.  It was lovely.  I loved how it covered and sat out over the full white petticoat she’d had me put on.  Next, she adorned my ears and neck with pearls.  But that was not the end.  Up to this point, I’d been made to appear feminine, but not allowed to look like a woman, because I’d not worn one of my wigs, which I did know from my private experience made a difference.  But Andrea was prepared.  She’d brought an auburn wig cut in a pageboy that she showed me and asked, “So, what do you think sissy?  Do you want to?”  As if I was going to say no.  I nodded, letting my smile get away from me.  “Please,” I answered.  “I thought so.  You are such a sissy,” she laughed.  But I didn’t care.  I just wanted her to put that wig on me. 

Once it was on and Andrea let me look at myself in the mirror, I was mesmerized.  I could not believe how good I looked.  I mean, I was still a man.  But the fantasy of being a woman felt real in that moment.  And I was going to get to stay dressed like this all day.  Andrea was enjoying my reaction.  “I think sissy likes,” she said.  Then she told me to get my black heels and put them on.  Admittedly, with the heels on, I was a tall sissy maid.  But I felt incredible.  I wished I could do this more often, and momentarily forgot that my cheerleader was off for the weekend with a man.  I was loving dressing up like this.

Andrea told me then that she had some errands to run, but would be back in a few hours.  I was confused, because I thought she was going to stay with me.  She then told me what she expected of me.  In other words, this was not simply playing dress up.  Andrea told me that she expected me to clean the entire house, so that it would be spotless for my cheerleader when she returned home.  I was to change and remake all of the beds, vacuum the entire house, dust, and make sure all of the laundry was washed and neatly folded and put away.  My entire Saturday was going to be devoted to performing as if I was an actual maid.  I was in disbelief at first, but Andrea assured me she was not kidding.  She then told me I was to curtsy whenever I addressed her, and to refer to her as Mistress Andrea for the remainder of the day.  So, within a matter of minutes, the joy I was feeling about getting to dress up like a sexy French maid was replaced with the reality that I was going to actually have to do housecleaning.  Andrea found her purse and said she’d see me soon, and that she expected me to be finished by the time she returned to inspect.

I was suddenly left alone to contemplate my situation.  Realizing it was going to take some time to accomplish all that Andrea had told me to do, I began stripping the beds so that I could get the laundry going.  It did not take me long to realize how difficult cleaning a house could be wearing 5-inch heels, not to mention with a butt plug in my pussy.  I was, as Andrea had told me I would be, constantly aware of the invasion, and the heels made every move a little more difficult.  But, accepting that this was my Saturday, unless I wanted to blow the whole thing up, which I didn’t, I went about doing as I’d been told.  Near mid-day my cheerleader sent me another text of her in the pool at the W.  She asked, “Are you being a good girl today?”  I had to smile inwardly as I considered the situation I found myself in.  My cheerleader was out of town enjoying the company of a man at the beach while her sissy husband was home cleaning her house for her.  We’d come a long way in only a few weeks’ time.  I replied, wondering if she knew what my plight for the weekend was, “Yes ma’am.”  I was hoping for some reply, just to engage with my cheerleader for a while, but none came.

I worked steadily for the next few hours and became so caught up in the work that I barely had time to really think about how I was dressed, at least from an erotic standpoint.  I suspect that was likely part of Andrea’s intent.  I was being shown what it felt like to serve.  I found that I was driven, though, by the hope of a future reward in the form of release from my chastity cage.  By late afternoon I had successfully cleaned our entire house.  My cheerleader and I had a maid who came once per week to do most of what I’d just done.  I wondered if she would realize that the house was unusually clean on her next visit the following Tuesday.  Andrea returned around 4ish carrying several bags of groceries, which she began to unload onto our kitchen bar.  I asked her what she was doing and she told me she was going to prepare dinner.  I thought that was very nice of her and offered to help her.  She began giving me directions on what she wanted me to do, cleaning vegetables and such.  I commented that there seemed to be quite a bit of food and that’s when she told me we were having company.  Or, at least, she was.  I was going to serve.  I seriously thought she was kidding and told her so.  But she wasn’t.  I immediately told her that I just did not think I could do that.  But, in her special way, Andrea set me straight.  She told me that I needed to do this to truly experience what it was like to be a sissy.  She also emphasized that the guests she was having over were people who she assured me would not be shocked to find a man dressed as a sissy maid.  And, she emphasized, they would not know me or ever see me again.  All I had to do was trust her and do whatever she told me to do and I’d be fine.  I was not happy about this development.  I asked her if my cheerleader knew what she was doing to me this weekend.  She told me that my cheerleader knew that I was receiving “special instruction” while she was gone, but that she did not know precisely what was happening.  So, here is a little confession.  I was truly worried, and scared, about the prospect of what Andrea had in mind for me.  But my penis was throbbing inside of its' chastity cage.  I wanted to do this thing!  I thought about it and then realized that this may be the only chance I would ever have to do something like this completely anonymously.  Even my cheerleader would not see me behaving as a sissy maid for a dinner party.  I wasn’t sure I could do it, but I did trust Andrea.  She just seemed to be so careful about things, and so I decided that I would do it.  I agreed.

Andrea and I worked together for the next hour or so preparing dinner.  She told me that the guests would include a man she dated from time to time, and another couple.  They all knew that Andrea was staying at someone’s house, but she had not told them specifics about me – only that there would be someone who Andrea was “working with."  Once we had dinner organized, Andrea went upstairs to change.  She told me to set up a bar and to prepare to serve drinks, telling me what she expected her guests would likely drink.  My nerves were on edge as I busied myself to welcome and serve guests as a sissy maid.  I couldn’t believe I was actually doing this!  When Andrea came downstairs I was nearly blown away.  She looked amazing!  She wore a tight, red satin sheath dress that barely reached her thighs.  She had on what I guessed were pantyhose, as I saw no signs of stocking tops, and black high heels.  Her long hair was piled high upon her head and she looked simply regal.  She surveyed things and praised me on how I’d set things up.  She then gave me some final instructions.  The first was to remind me to refer to her as Mistress Andrea.  The other guests would be referred to as Mr. or Miss, and I was to curtsy at every command or request, and whenever I departed or entered any of their presence.  She emphasized that I was to do whatever I was asked, and that I should not concern myself with what they might think of me – I was a sissy – and as such, I should accept whatever they might think, emphasizing again that I would never see them again and, thus, had nothing to really worry about.  That was some consolation to me.  However, I was, nonetheless, extremely on edge about what I was doing.

I froze when the doorbell finally rang.  I had worked myself up to facing this challenge head on.  But faced with the sudden reality of greeting guests into my home, dressed up as a French sissy maid, I didn’t think I could go through with it.  Andrea came to me and looked into my eyes and said, “You can do this sissy.  None of these people know you.  And they are expecting to find a sissy maid.  They are not going to be shocked.  Now, go answer the door and do as I have instructed you.”  I knew that I had to go through with this at this point.  So, I nodded and said, “Yes Mistress Andrea.”  She smiled and said, “Good girl.”  I curtsied and then walked to the front door, conscious of my heels clicking on the hardwood floor.  I opened the door to find three expectant faces, each of them obviously interested to see what they would find on the other side of the door – two handsome men and a beautiful redhead.  I was tongue tied at first, but then remembered what Andrea had told me.  I curtsied, looking downward as I did.  In a soft voice, well aware that I didn’t come close to sounding like a woman, I said, “Good evening.  Mistress Andrea is expecting you.  I’m Sissy Leeanne.”  (This was the first time I'd revealed my self-chosen sissy name to anyone.  Andrea did not even know I was going to do that.)  The redhead spoke for the trio at the door.  “Nice to meet you sissy.  I’m Miss Anne.  And this is Mr. Carl,” referring to the man with her, “And this is Mr. Joseph.”  “Won’t you please come in,” I invited them inside.  “Mistress Andrea is in the den.  I’ll show you.”  I curtsied and turned to allow them to follow me.  As I entered the den I announced, “Mistress Andrea.  Your guests have arrived.”  Andrea stood up to greet them, receiving a hug from Miss Anne and Mr. Carl, and a much warmer hug from Mr. Joseph.  Once greetings were complete, I offered everyone a drink, took their orders, curtsied, and left to prepare drinks.  My heart was racing out of control.  I had been so anxious about that moment, but as it turned out, Andrea had been correct.  Her guests treated me as though I was nothing out of the ordinary.  It was strange, really.  I had worked myself up to thinking that they would immediately laugh at me, but they didn’t.  Although, I did sense that Miss Anne was sizing me up.  Was there something about women and sissies?  Something that made them more, I don’t know, more apprising of us?  Checking out how feminine we managed to be?  I couldn’t put my finger on it.  I served them drinks and then, curtsying again, excused myself to retrieve appetizers.  When I returned to set them out, the four of them were chatting like old friends, acting as though I were just a servant – as opposed to a man masquerading as a sissy maid.

Following some earlier instructions Andrea had given to me, I stood back and to the side, waiting to act upon any request that she, or the others, made of me.  I noticed Miss Anne cutting her eyes toward me from time to time, but she never spoke to me.  Meanwhile, they continued to socialize and behave as though I were not even present.  It was strangely disconcerting.  On the one hand, I had been nervous and worried about how I would be treated.  On the other hand, I was actually bothered that I was receiving none of their attention.  You might have thought I would have been relieved that I was not an object of their scorn or teasing.  Instead, I found myself feeling irritated.  Again, I suspect that was Andrea's intention.  She seemed to understand my sissy psyche so well.  As I was stewing silently next to the wall, my iPhone chimed the tone I have associated with my cheerleader.  I noticed that the phone was lying on a coffee table next to Andrea.  My eyes were met by Andrea's, who obviously knew it was mine.  But I did not move.  Andrea smiled rather slyly as she said to me, "Looks like you have a text message sissy."  I immediately felt anxious.  I did not want to look at it just then.  As my cheerleader had been sending me photo messages all weekend, I was not looking forward to seeing what this message might contain.  I simply replied, "Yes Mistress Andrea," but did not move.  Andrea, though, had other plans, and as they panned out, I realized they were devious.  Holding the phone toward me, Andrea told me to check the message.  Reluctantly, I accepted the phone from her, entered my pass code, and opened the text message.  What I saw shocked me.  My cheerleader had, indeed, sent me another photo text.  She and Randall were going out for the evening.  I did not recognize the dress she wore.  It was not one I'd selected for her trip.  And it was not the kind of dress that my cheerleader was known to wear.  The only word to describe it was 'slutty.'  As I stared at the photo, I sensed that the others in the room were watching my reaction.  Finally, Andrea interrupted my thoughts.  "What did she say sissy?"  I told her "nothing," that it wasn't a message.  "Oh!  Another photo?  Let me see!" she insisted.  I tried to resist, but realized Andrea was not accepting "no" for an answer.  She looked at the photo my cheerleader had sent me, raised her eyebrows, and exclaimed, "Oh my!  It looks like your wife is going out to get mind fucked by every man who sees her."  I didn't reply.  What could I say in response.  Miss Anne, on the other hand, was intrigued and insisted upon seeing the photo of my cheerleader.  She reacted much like Andrea had, and then showed the photo to Mr. Carl and Mr. Joseph, asking them if they wouldn't want to fuck my cheerleader.  They each agreed that she looked  "quite fuckable," as Miss Anne had put it to them.  Meanwhile, all I could do was stand by and suffer the humiliation of them all seeing my cheerleader dressed so sluttily while I was dressed as a sissy maid.  Andrea told me I should respond, telling her to have fun.  Miss Anne teased me that perhaps we should send her a photo of me.  Andrea acted like she was considering it, but perhaps showing mercy as she saw the panic in my eyes, she declined.  "I want her to see her sissy maid live tomorrow."  Fuck!  She planned for me to be dressed like this when my cheerleader got home the next day.  Suddenly, nothing I did for the rest of the evening could surpass the anxiety I had about the next day. 

The evening proceeded with me serving them dinner.  I was allowed to eat alone in the kitchen while they ate.  Andrea did everything she could to make me feel like hired help in my own home.  Being a sissy maid wasn't turning out to be the erotic fantasy I'd always had.  I served dessert in the den, and cleaned the kitchen while they continued having a fun evening.  I began wondering how late they would stay.  They had been drinking steadily and were actually being sort of loud.  Around 11, though, Miss Anne and the men began saying their goodbyes to Andrea.  I walked them to the door.  Miss Anne kissed me on the cheek and whispered in my ear, "You look quite fuckable yourself sissy."  Then, loud enough for the others to hear, she said, "It has been a true pleasure meeting you sissy."  I thanked her and curtsied as they left, leaving me with Andrea.

After they were gone, Andrea was beaming at me.  She seemed genuinely pleased, and told me so.  She told me that I was a natural sissy maid.  Should I have felt embarrassment?  Probably.  What I felt instead was pride.  I'd done it!  And it wasn't at all what I'd worried it would be.  The worst part was when they were all lusting for my cheerleader.  But I couldn't really blame them.  She did look hot.  Andrea told me to go upstairs and get ready for bed.  I was actually pretty happy to do that.  I'd been in high heels all day and was looking forward to taking them off.  I took off my uniform and showered, washing off my makeup, something else that felt good to remove.  I wore a matching pair of yellow panties and bra, and put on a light blue babydoll, then joined Andrea in the guest room.  She was just taking off her pantyhose as I walked in.  She crawled onto the bed nude, without taking a shower, and immediately put me into service between her thighs, telling me she had been looking forward to my mouth all night long.  I smiled at the compliment and did my best to bring her to several orgasms.  Later, we snuggled and slept soundly.  Working all day as a sissy maid had worn me out.  We slept late.  It didn't take long for my anxiety level to spike again as Andrea made clear that she expected me to be dressed as a maid to greet my cheerleader upon her return.  I asked if Andrea really thought that was a good idea.  I was worried that my cheerleader would be put off seeing me in full femmy style, including a wig.  Andrea insisted that if my cheerleader and I were going to move forward in a cuckold marriage, that she needed to see me as the sissy I was.  She said her weekend away with Randall, with my blessing, was important, but that me welcoming her home as a sissy was equally important.  Relenting, but scared to death, I let her make me over and dress me up as a sissy maid again.  We then had coffee, ate breakfast, and chatted, Andrea giving me instructions for when my cheerleader arrived home.  The gist was that I was not to treat her like my wife, but rather as my Mistress who I was to serve, including curtsying and everything.  It was going to be so difficult, but I was going to go through with it.  Later, Andrea packed her things, leaving me alone to wait for my cheerleader to arrive home.  Thus, I spent a lonely, anxious, Sunday afternoon, waiting to reveal myself as a total sissy to my cheerleader.

When I heard her key in the lock around 5 o'clock, I quickly went to the door to greet her in the way Andrea had told me to do.  While I was prepared for her, as much as I could be, she wasn't prepared for me.  Her first reaction was total shock.  I don't know why, but I had thought perhaps Andrea had forewarned my cheerleader, but I don't think she had.  To make matters worse, instead of catching a cab as she'd told me she would, Randall had driven her home.  He was carrying her luggage to the door for her.  So, there I stood dressed as a sissy maid in front of my cheerleader and the man who had been fucking her all weekend.  I felt deep embarrassment and humiliation.  I think my cheerleader was embarrassed as well, seeing her husband dressed as I was in front of another man.  Not knowing what to do, I did what Andrea had told me to do.  I curtsied and said, "Welcome home darling.  I hope your weekend was all you hoped it would be."  My cheerleader was speechless at first.  Finally, she spoke, and with an odd smile, said,  "It was.  Thank you.  It looks like you've had an interesting weekend as well."  I replied, "Yes ma'am."  She turned to Randall, who had been taking in the entire exchange between us with a wry grin, almost as though he did know what to expect, and asked him if he wanted to stay for a drink.  He said he would, so I went to work, retrieving them each a drink and served them in the den.  Suddenly, it was not just me and my cheerleader, as I had anticipated, but me and them, me cast in the role of servant to them.  No doubt, this was what Andrea had hoped would occur.  She wanted my cheerleader to see me in this light, and for her to accept me in such a role as well.  My cheerleader seemed to naturally gravitate to being affectionate with Randall, even with me in the room.  As they were finishing their drink, she grinned seductively at Randall and asked if he had time for a "quickie" before he left.  He smiled and said, "Sure."  She stood, took him by the hand, and led him toward our upstairs.  She paused and looked at me.  "Come on sissy.  I want you to help."  Fuck!  I was being asked to participate in their lovemaking.  I hadn't prepared myself for that.  But I felt the telltale response that let me know I was excited at the prospect.  I'd been worried about how my cheerleader would respond to me sexually after such a weekend as she'd had.  But, no.  She still wanted me involved.  So I followed her and Randall to our bedroom.

And so this is how our weekend ended.  My cheerleader immediately noticed how clean the room was and commented upon it, asking who cleaned.  I admitted that I had done it.  She asked me if Andrea had me serving as her maid all weekend.  Again, I told her yes.  She smiled and said, "Hmmm.  Maybe we can save some money by letting ours go?"  I shrugged, but said I didn't want to take away her employment.  My cheerleader agreed and said she'd only been teasing anyway.  She looked me over and then said, "Sissy, why don't you help Randall and me get undressed, and then, you know, ready?"  I knew what she meant.  I curtsied for her, and she cracked a smile, suppressing a laugh I think.  "Yes ma'am."  Beginning with her, I unbuttoned her blouse, revealing a new blue lace bra.  Randall had bought her more than the new dress I'd seen her wearing the night before.  I unfastened her tight mini-skirt and helped her shrug it down her legs, revealing the thong panties that matched the bra.  Her shaved pussy lips, clearly damp with sexual anticipation, were outlined against the sheer nylon.  My cheerleader seemed mesmerized as she watched me undress her for Randall.  I reached to unfasten her bra, but she stopped me.  "No sissy.  Randall.  I want to watch you."  So she was going to make me undress her man for her.  Randall was standing behind me, watching me undress my cheerleader.  I turned to face him and asked, "May I?"  "Sure sissy," he replied.  My hands were visibly trembling as I began unbuttoning his shirt, revealing his muscular and tanned shoulders.  He was a well built man.  I could not deny that.  Then, stooping the way Andrea had shown me, I squatted low to remove his shoes, then unbuckled his belt and unfastened his pants, lowering his zipper in the process.  I could see already that his cock was erect.  I didn't know if he was excited anticipating fucking my cheerleader in front of me, or whether he was turned on because I was undressing him.  When he was stripped down to his boxers, I hesitated.  My cheerleader told me to take them off.  As I lowered them, his cock sprang free.  It was as big as I remembered from the previous weekend.  I began to stand up, but my cheerleader told me to stop.  She told me get on my knees and suck him for her.  Accepting my fate, and really anxious to suck him again, I fell to my knees and held him with my manicured fingers, then began a slow, wet and sensuous blow job of my cheerleader's man.  I understood that was what he was now - her man.  I was her sissy.  She seemed to accept it.  I realized that I was going to have to accept it as well.  I'd set this new relationship in motion a long time before this day when I confessed my attraction to wearing women's lingerie.  My cheerleader had gone from upset to learn I wore women's clothing, to accepting and tolerating it, to now embracing it and cuckolding me.  Now, seeing me dressed as a sissy maid, she wanted to watch me on my knees sucking her man's cock.  And I did so.  Willingly.  As I sucked him, Randall began thrusting in and out of my mouth, effectively fucking my face, a first for me, although not the last time a man would fuck my face.  It just felt natural to me as I was on my knees taking his cock into my mouth.  There was a moment when I sensed that he was about to orgasm.  My cheerleader must have sensed it also because she told me to stop.  I almost had to push Randall away from me.  I think he wanted to cum in my mouth.  And the truth is, I wanted him to.  

My cheerleader reached behind her back and unfastened her bra, letting it fall to the ground, then slid her panties off.  Beckoning Randall to the bed, she said, "I'm ready baby.  Fuck me.  Watch sissy," she told me.  So I stood by the bed and watched Randall fuck my cheerleader.  But more importantly, I watched her respond to him pounding her with his extremely large, very hard (courtesy of me) cock.  He had tremendous stamina, and my cheerleader, who had obviously found a rhythm with Randall, helped him by grinding her pussy onto him as he fucked her.  I knew I would never be able to deny her this pleasure again.  Our marriage had shifted to another plane and would stay there until my cheerleader decided otherwise.  Randall began driving into her and pausing between thrusts, his imminent ejaculation inside of her obvious. 

 When he finished he let his softened, but still thick, cock, slip out of my cheerleader.  It was covered with cum comingled with my cheerleader’s own fluids.  I was awestruck at what I’d witnessed. 

 My cheerleader, catching my eye, said, “Clean him sissy.”  I hesitated, but she repeated herself, "Suck him clean."  I leaned down to the bed and let him stick his gooey cock into my mouth, the taste of the two of them a mixture that I could not deny liking.  I had already acquired a taste for sperm.  And I always loved the way my cheerleader tasted.  After Randall's cock was clean my cheerleader said to him, "You can leave us now baby.  I want some time with sissy."  And so, just like that, Randall dressed, kissed my cheerleader goodbye, said, "See you next weekend," and left us alone.

My cheerleader looked at me, smiled, and told me to go get ready for bed, explicitly telling me to wash off my makeup and not to wear the wig.  I went to my closet, took off my clothes, and went to the bathroom to shower.  I put on the same babydoll I'd worn the night before, and went to join my cheerleader in bed.  She was lying on her back, feet pulled up near her butt, thighs spread, pointing to her pussy.  "Lick me."  I crawled onto the bed and leaned close to her smooth slit.  Randall's sperm provided a slick coating on her lips.  She was watching me as I ran my tongue along her slit, revealing a thick ooze of sperm within her.  "God!" she exclaimed.  "You have no idea how hot that is to me.  I love that you'll do that."  I stopped and looked up to her.  "I love you."  "I love you too.  So much.  Thank you for giving me this weekend.  It was amazing!"  "You're welcome," I said, then returned to cleaning Randall's cum out of her pussy.  I brought her to another orgasm and she finally told me to stop.  

When I looked up, she was holding the key.  "Are you ready?" she smiled.  Was I?  Oh yeah!  She sat up, helped me remove my panties, and stuck the key into the padlock, unlocking it, and then removed the plastic prison that had tortured me for a week.  Grinning, she crooked her finger, indicating she wanted to suck me, and she gave me an incredible blow job.  I tried to make it last, but soon felt my own orgasm building.  I wanted to fuck her, but she a different plan.  Pulling away from me, she began jacking me off right onto her breasts, forcing me to cum all over her tits, covering her in a sheen of sperm.  When I was spent, she pressed my face toward her breasts, making me suck and lick them clean.  I was disappointed, but didn't complain.  I was so happy that I had been permitted release that I didn't want to ruin it for her.  

I was brought back to reality when she immediately said we had to replace the cage.  I tried to protest, but she said that Andrea insisted it was necessary, and the best time to replace it was right after orgasm.  So I relented and let her put it back on. 

 We then snuggled and fell asleep.  And that is how my weekend as a sissy cuckold ended.  I was being treated like the sissy I had always known I was.  I was finding the adjustment more difficult that I thought, but it was taking place no matter how I felt about it at this point.  We didn't know it then, but the following weekend would be our last with Andrea.  And she had special plans for each of us.