Sunday, December 1, 2013

Sissy's And Cheerleader's Last Weekend With Andrea - Part One

[NOTE - Anyone who is just beginning to read my blog, might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow - Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home - Cheerleader Cucks Sissy - Cheerleader and Sissy Are Mentored - Sissy Offers Context For Cheerleader - Sissy Sees Her Future - Sissy Adapts To Chastity - Sissy And Cheerleader Spend A Weekend Apart, Our Weekend Apart Aftermath - Cheerleader Has A Heart-To-Heart With Sissy.  These are the previous posts that tell the story about my sissy journey.]
The conversation my cheerleader and I had the Monday following her return home from spending the weekend in Ft. Lauderdale with Randall was a much needed clearing of the air between us. I admit that I continued to feel a strange and conflicted sense about how our relationship had so transformed over the course of a few weeks.  However, the reassurance I felt from her emphasizing that, no matter what happened, she still loved me and never wanted to be without me, helped me to accept what appeared to be a significant shift in the role I would play for her.  I loved her so much.  After all, she had saved me at a point in my life when I truly doubted I would ever have a meaningful relationship with a woman, including all that was entailed in that - emotional, physical and sexual love - even spiritual love.  If it were not for her, I truly don't know what would have become of my life.  And so, if this new physical expression of sex was good for her, even though it wasn't turning out exactly as I had fantasized, I was prepared to see it through.  Plus, there was a lot about what we were doing that I was enjoying, if I was honest with myself.
The Thursday following, as we were watching television, my cheerleader's iPhone rang.  I had taught her how to assign a special ring tone for specific callers.  The ring on my iPhone when she calls me is Aerosmith's "I Don't Want To Miss A Thing."  When I call her, her iPhone plays "Baby I'm Yours," by The Mamas and The Papas.  I know.  Cute.  Huh?  Anyway, the song that played when my cheerleader's iPhone rang was the female orgasm segment from "Wait (The Whisper Song)" by the Ying Yang Twins.  She gave me this little smile she has when she realizes that I'm picking up on something we haven't shared yet.  As soon as she began talking I was able to put 2 and 2 together and knew it was Randall calling her.  As it turned out, the call was to firm up their weekend plans.  
When she hung up I already knew from her side of the conversation that he was going to spend the weekend with us.  My cheerleader smiled at me as she set her iPhone down.  "You don't mind?  Do you?" she asked, without really needing my answer.  I assured her it was fine.  I'd actually been expecting it.  She stood up and held her hand out to mine, "Come on.  I want you to help me with something."  I followed her upstairs.  She went into the bathroom and turned on the water for her bath.  Her need for my assistance?  To cut it short, I washed her hair and helped shave and freshly trim her landing strip on her pussy, and then painted her fingernails and toenails.  Bright red.  That night, in bed, she let me pleasure her orally.  I enjoyed the feeling of her smooth slit and pussy lips.  When I finished, or, I should say, when my cheerleader let me stop, she thanked me and added, "Tomorrow night I'll be filled with Randall.  Can you wait?!"  I was embarrassed to be talking this way with her, but admitted to her that I was looking forward to it.  And I was.  At least my penis swelling within its cage said that I was.
I'm going to say this now, rather than let the description of what took place over the next 72 hours of my life suggest what the weekend turned out to be like for me.  Obviously, as I'm telling this story, I made it through the weekend.  But there were so many moments when I wondered if I would.  Moments when I didn't think that I could.  With the help of a few well-placed words of encouragement and the recollection of the words my cheerleader shared with me the previous Monday, though, I made it through what was the most difficult series of days I have lived through since my cheerleader cuckolded me.  In the end, I told myself that she loved me and I loved her, and that with our love we could survive anything.  But this weekend was a true sissy test for me, as I'm about to explain.
Right after I arrived to work on Friday, Andrea texted me.  She told me to meet her at my house at 2 o'clock.  Her text wasn't a request.  I was able to leave work early, so I acknowledged that I'd be there, wondering what I would discover upon arrival.  My cheerleader was not home when I got there.  She was off from work that day, so I figured she was running errands.  As it turns out, Andrea had sent her out.  She wanted to be alone with me.  Not long behind me, Andrea was in full professional mode as she entered our house.  She told me to get undressed and shower, expressly telling me to shave all over.  A makeover was in my immediate future.  The previous weekend Andrea had done wonders with me and I enjoyed the result.  But it was easier for me to enjoy the results with my cheerleader not there to see me, at least until she got home on Sunday.  This makeover, I surmised, was for her benefit, and I was feeling that familiar wave of anxiety begin to sweep over me.  Yes.  I wanted it.  But equally so, I knew I'd feel embarrassed to be presenting myself so femininely in front of my cheerleader and her man.
Andrea had very good makeup skills.  I suppose, being in the profession she was in, such abilities came in handy.  As she worked on me she talked about the upcoming weekend.  It was then that I learned that this would be our last weekend with Andrea in our lives, at least in such a capacity as she had taken on with us.  My reaction to learning this news was mixed.  I don't know why I expected that she would always be around.  I mean, who has that kind of time to devote to anyone?  I was disappointed that we might not see her again and even wondered how my cheerleader and I would do without her guidance.  In short, Andrea explained that this weekend was my Final Exam, and that she was going to be there to help me pass it, but that I needed to be prepared.  Confused, I asked her what she meant.  Simply, she told me, I was expected to serve my cheerleader the entire weekend as her sissy husband, adding that serving her meant serving everyone she expected me to serve.  In other words, I surmised, Randall. 
Andrea applied a very dark makeup motif.  It wasn't what I would describe as Gothic.  But, it was more sultry than she'd done to me before.  She painted my nails black.  When it came time for getting dressed, I was prepared for a maid's uniform.  She pulled out a pink corset with a light pink lace tulle skirt at the bottom.  She helped me into the  corset, snugging it up tightly.  She helped me attach white stockings to the garter straps.  She surprised me with a new pair of high heels she'd bought for me.  They were pink paten leather open-toed heels with five inch heels.  She then clipped on pearl earrings, slipped some bangle bracelets on me, and attached a string of pearls around my neck.  Finally, she pulled out a blonde pageboy styled wig and attached it firmly to my head. 
 Stepping back to admire her work she declared, "Perfect!"  I was confused.  I felt nearly naked.  All I wore was the corset.  No panties.  No bra or breast forms.  No dress.  Just the corset with the frilly lace skirt.  My chastity caged penis hung openly between my thighs.  My flat male chest was bare.  I fully realize how silly it sounds for me to say what I'm about to say.  There I was standing before a woman who had spent the last month completing my feminization, so to speak, wearing a pink corset with a frilly lace skirt attached, complete with high heels, a wig and makeup.  And what was my concern?  That my penis was exposed - not covered by panties - and that my male titties were bare.  Seriously!  But that bothered me.  I suppose it had something to do with exposing me so fully as a fraud.  If I concealed all of my maleness - if my chest was shaped like a woman's - then I was better able to pretend that what I was doing was okay.  But the corset Andrea had laced me into exposed me as though I were utterly naked.
When I expressed my concern to Andrea, she gave me a knowing smile, as if she understood precisely what I was feeling.  And what's more, it was as though she was pleased to know that she'd achieved her goal.  "You are a sissy," she said flatly.  "You will look and act like a sissy the entire weekend.  Do you understand Sissy?"  she asked me.  It was sinking in.  I was suddenly extremely anxious about seeing my cheerleader and Randall dressed as I was.  This was the first of many moments I would have to survive and, really, plow through over the course of the weekend.  I wonder sometimes how things may have gone if I'd backed down then.  Would my cheerleader have been disappointed?  Would it have ruined her weekend?  I don't know, because I didn't back off.  And each successive step I took that weekend made turning back more difficult until, when it was over, I'd made it.
I told Andrea that I understood and asked what was next.  It turns out that there was one more thing - she inserted the bejeweled stainless steel butt plug inside of me, explaining that it would stay in fine if I maintained the right pressure.  She then explained that I was to go downstairs and prepare for Randall's arrival.  I needed to set up my bar and prepare some snacks.  I also learned then that Randall was taking my cheerleader out to dinner.  Again, and not for the last time, my stomach flipped as I realized my subservient sissy role placed me directly outside of the weekend's planned events.  Even the idea that Randall was going to spend the weekend at our house was different than I'd imagined.  He wasn't visiting my cheerleader and me, as our guests.  He was visiting her.  I was going to be an observer, albeit an active observer playing the role of servant to their wants.
Andrea came with me and helped me get organized.  I noticed that she was behaving slightly differently than she had on previous weekends.  The first two weekends, she seemed to be a part of the social activities.  The weekend that my cheerleader went away with Randall, Andrea was part companion and part teacher.  This weekend, so far, I felt that Andrea was evaluating me and providing ongoing encouragement whenever she sensed reluctance or concern on my part.  As I moved about the kitchen, feeling extremely self-conscious because I felt naked, Andrea talked to me about how she expected me to behave during the weekend.  She emphasized curtsying, how I was to address my cheerleader, Randall, or any guests.  The mention of possible guests gave me pause and I asked if there would be guests.  Andrea told me I should not concern myself with whether there would, or would not be.  I was to immerse myself in my role as my cheerleader's sissy.  The way she explained it was that anything I did was for her pleasure, no matter how intimate or not.
Around 4:30 my cheerleader arrived home from wherever she'd been.  I don't think she had been briefed on what to expect when she saw me.  Her immediate reaction was almost shock upon seeing me dressed as I was, but more like utter astonishment.  Her eyes revealed that she did not expect to see me dressed quite so sissyish.  "Oh my!" she exclaimed.  "Sissy!"  In that moment I felt as sissyish as I had at any other time since she'd cucked me.  After her initial reaction, though, she seemed to accept me.  She greeted Andrea, set down the shopping bags she'd carried inside, and approached me.  I'd forgotten to curtsy when my cheerleader entered.  Andrea gave me a stare that reminded me of my transgression.  I dipped as my cheerleader drew nearer.  "Hello Mistress," I said.  "Hello Sissy," she smiled.  She stood close to me and touched me on my cheek, kissing me softly.  Her other hand gently stroked my bare ass as she fondled me possessively, letting her fingers find the plug inside of me and pressing it inward slightly.  "You look very cute honey.  I think Randall will be pleased."  This statement by my cheerleader was the first hint that Randall liked seeing me sissified, as opposed to merely tolerating me because it was part of the turn-on for my cheerleader and he was enjoying the freedom I gave him to have her.
My cheerleader spent time teasing me with her touch, kissing me and assuring me how pretty I looked.  My reaction to her attention was mixed.  I felt anxiety thinking of how Randall would react to seeing me dressed as I was.  I was self-conscious as I sensed Andrea observing the interaction between my cheerleader and me.  But I also felt warmth to hear my cheerleader praising me and I responded to her touch as you might expect.  After a few minutes my cheerleader excused herself to get dressed for her dinner date with Randall.  I assumed her shopping bags contained the outfit she was going to wear, so I realized she was going through some special effort for Randall.
My cheerleader had been upstairs getting ready for at least an hour when the doorbell rang.  Randall had arrived.  It was the moment of truth for me.  I was about to display myself to my cheerleader's man as a completely feminized sissy husband.  My feet were frozen to the floor when the bell rang again.  "Go," Andrea told me.  "You can do this Sissy.  You need to to do this.  Go."  I didn't say anything.  Following Andrea's urging, I took the first step and went to answer our front door.  Careful to conceal myself from a view of the street, I swung the door open to let Randall enter.  As he stepped in carrying an overnight bag, I looked downward and curtsied.  "Good evening Sir," I said.  "Please come in."  We were within inches of each other.  Randall said nothing at first.  Instead, he visually scanned up and down my body.  His apprising eyes felt hot upon my exposed body.  Finally, he spoke.  "Look at you!" he exclaimed.  "Unbelievable!" he added.  The embarrassment I experienced as my cheerleader's man took in my sissy presentation to him was beyond what I'd geared myself for.  In the entire time that my cheerleader had been fucking Randall, I'd never felt him take such an interest in my sissy appearance.  I felt utterly at his disposal, almost as though I was his property.  As if to emphasize this to me, he touched one of my exposed nipples.  I probably should have backed away or done something to stop him, but I truly felt helpless.  His touch was almost electric.  Goose bumps broke out over my body and I felt my nipple grow at his touch.  I could not look him in the eye.  I wanted to sink into the ground or disappear.  
Finally, I gained some sense of control and asked if I could fix him a drink.  He smiled and said that would be nice.  I seized upon this opportunity to put some distance between us.  As I turned from him to walk toward our kitchen I discovered that Andrea had been watching.  She was smiling broadly.  "Good girl," she whispered as I passed her.  She greeted Randall as two good friends would.  They hugged and she complimented him on his suit, telling him he looked very handsome.  And he did.  Andrea and Randall chatted as I prepared his Maker's Mark.  He was telling her that he had reservations at a nice restaurant in Arlington where he was taking my cheerleader for dinner.  Hearing a man discuss his dinner plans with my cheerleader felt so strange.  This man had been fucking my cheerleader for a month by this point.  They'd gone away together for a weekend.  He would, no doubt, be intimate with her this weekend.  But hearing him discuss with Andrea his dinner date plans with my cheerleader, while I stood by dressed so femininely and serving him a drink, stung me.  What Andrea had said to expect of the weekend was settling upon me.  I was here to serve my cheerleader.  And serving her meant serving her man.  
I handed Randall his drink and asked Andrea if she wanted anything.  She told me to bring her a glass of white wine into the den.  They walked together toward our den while I poured Andrea her glass of wine.  After delivering her wine to her I stood by while they chatted and sipped their drinks.  Our attention was drawn toward the sound of my cheerleader's high heels as she walked downstairs.  Were it possible for me to be more shocked at her appearance than she had been at mine earlier, then I think I was.  My cheerleader had gone to a lot of trouble to look fabulous.  She was wearing a very short and tight sheath dress.  The dress was white with black sequins that created a glowing and glittering effect.  Her black heels were at least 5 inches tall.  Her hair was brushed out and flowing over her bare shoulders.  Her makeup was applied flawlessly.  The thing that stood out most to me was the simple necklace that adorned her bare throat - the key to my chastity cage.  My cheerleader paused, as though for effect, at the entrance to our den, clearly enjoying the attention she had drawn from all of us, each seeing her from our own unique perspective - Andrea, the tutor; Randall, her lover; and me, her cuckold sissy husband.  I cut a glance toward Randall.  His lustful gaze was unmistakable.  He understood that my cheerleader was dressed for him - not for me - although I wondered if she wasn't making a point to me as well.  
My cheerleader walked directly to Randall, who had stood when she approached.  When she got to him she draped her arms around his neck and gave him a long and sensuously wet kiss right in front of me and Andrea.  I was stunned to see her give herself to him in such a wanton manner.  Randall grabbed my cheerleader's ass, then slid his hands possessively under her dress.  My cheerleader offered no resistance and, as her dress rose higher, I could see that my cheerleader apparently was not wearing panties.  Randall seemed to make the same discovery as me.  Meanwhile, my cheerleader had begun fondling Randall's crotch.  Her brazen display was completely unexpected and out of character.  I couldn't believe how she was behaving.  Loud enough for all of us to hear, she whispered urgently into his ear, "I am sooo wet!  Feel me!"  From where I stood I could see Randall's face as he reacted with an eagerness about which I could not blame him.  My cheerleader was coming on to him very aggressively.  What man would not respond as Randall was?  His hand moved to the front of my cheerleader's dress, raised her hem upward, and I could see that he had placed his hand between her thighs.  My cheerleader spread her legs, adorned in lace-topped, stay-up, thigh-high stockings, giving him full access to her pussy and she sighed audibly at his touch.  I don't know how Andrea was reacting to what was taking place because I could not avert my eyes from the scene.  Randall was fingering my cheerleader as she ground herself against his hand, kissing him passionately as he probed her.  I have described my cheerleader many times as a good girl.  I know that.  And she is.  But I have also written that she does, and has, enjoyed sex, including my own kinky displays.  But I had never seen her like this.  Perhaps it was because it was not me.  But watching her give herself in this way to Randall was beyond anything I could have imagined.  
After a few moments, but what felt like forever, my cheerleader began fumbling with Randall's belt buckle.  She was unfastening his pants!  She was attempting to free his cock!  I was stunned!  Beyond stunned!  What was my cheerleader doing?  I couldn't believe what I was seeing!  As she snaked Randall's hard cock from his pants she moaned urgently, "Fuck me!  Please?  Fuck me!"  It was as though she had been thinking of being fucked the entire week and now that Randall had finally arrived, she could not wait until they returned home from their date to get him into bed.  As I stood helplessly by, my cheerleader begging another man to take her, Randall turned her toward the wall beside them and pressed her against it, his trousers sagging to his knees.  With her help, he aimed his cock toward her pussy and I watched in shock as he slid inside of her.  My cheerleader raised one leg and wrapped it around his thigh, pulling him completely inside of her.  He then grabbed her other leg, lifted it behind him, and raised her upward and against the wall.  Wedging her against the wall, my cheerleader's arms wrapped around his neck and her legs around his waist, Randall began fucking her violently right in front of me and Andrea.  My cheerleader's eyes were squeezed shut as she panted, moaned, and groaned with each re-entry of his cock.  From where I stood, to their side, I could see each thrust and withdrawal.  He looked even bigger tonight than I recalled.  His shaft was shining from the wetness of my cheerleader's hungry pussy.  As shocked as I was at what had bolted from out of the blue and began to unfold in front of me, I could not look away.  My cheerleader was being fucked like she had never been fucked before - at least not by me anyway.  Randall fucked her and fucked her and fucked her.  I felt my own penis swelling against the restrictions of its prison, evidence that despite my shock and embarrassment to be witnessing my cheerleader being pleasured in this aggressive manner by another man, I was turned on by the erotic display.  Eventually, it became apparent that Randall was going to cum inside of her.  As he did, she cried out, "Yes!  Yes!  Yes!"  The two of them were panting from the incredible exertion they'd undergone in a matter of minutes.  
Still hanging onto Randall, my cheerleader began, slowly, laughing, as if overcome beyond her own belief at what had just happened.  Then, she seemed to gather herself, and looked at me, suddenly aware that I was staring at them, as if transfixed, because I was.  "Sissy," she said.  "I'm going to need some help sweetie."  I was too stunned to move or respond.  She spoke again, "Come here baby.  I need you," she said as she looked downward to where Randall was still embedded within her.  In that moment it registered what she meant.  I was going to clean her out.  Still frozen in place, I heard Andrea say, "Go on Sissy.  Do it."  Willing my legs into action, I walked toward them, and as I did, Randall let his spent cock slip out of my cheerleader, thick strands of his cum trailing behind.  My cheerleader quickly covered her pussy with her hand, as if to contain his secretion within her.  Nodding to Randall, she told me, "Him first."  Randall looked at me as if he wondered whether I really would.  Looking back on this event, I believe that I was simply too confused and shocked to actually think.  Encouraged by my cheerleader and Andrea, I simply did.  I fell to my knees and began licking the cum off of Randall's cock.  
After he was clean I looked at my cheerleader.  The expression on her face as she watched me turn from sucking her man clean to preparing to clean her pussy was one I will never forget.  It wasn't quite a smile.  And it wasn't one of astonishment either, as if she couldn't believe I was really doing it.  It was more of wonderment that I would do such a thing for her.  There was also a sense of love in the way she looked at me.  Kneeling beneath her as she straddled above me, she removed her hand and I locked my mouth on to her messy pussy and began to lick and suck her.  There was a lot of cum inside of her and it began to flow heavily as soon as I began sucking her.  My cheerleader began to gently rock against me, sighing at my efforts, and as I continued to lick and suck her, I could sense that she was about to have another orgasm.  Within a matter of minutes my cheerleader had been given orgasms by two different men, if I could be called a man  at that moment. The task complete, my cheerleader coaxed me to stand.  Embarrassment immediately swept over me as I knew I'd now have to face Andrea and Randall, who'd just watched me clean Randall's sperm out of my cheerleader.  And then, as quickly as my embarrassment rose within me, it was put on hold when my cheerleader pulled me to her and kissed me as deeply and as passionately as she had Randall earlier, grabbing me by my naked ass cheeks and holding me close to her, my chastity caged penis pressing against her bare slit.  When she finished she whispered to me, "I love you so much. Thank you sweetie."
I don't know how to describe how I felt in that moment.  A man had just fucked my cheerleader in the most dominantly animalistic way that a woman could be fucked.  Right in front of me, her husband, as I stood by wearing nothing except a pink corset and high heels.  And yet, despite that, in that moment I was filled with love and devotion for her beyond anything I could have imagined.  "I love you too," I told her.  "I know you do," she replied.  "I know you do."  She then pulled her dress back down and began to get herself together.  Looking at Randall she said, "So, are you ready to go?  I'm starved!"  Randall chuckled and said he was too.  
They said goodbye to Andrea and me and left for their dinner date.  When the door closed, Andrea said to me, "Have a seat.  I'm going to fix you a drink."  I was still in a fog.  Andrea had, I thought, tried to prepare me for whatever, but she could not have prepared me for what had just happened.  I sat as instructed and waited for her to bring me my drink.  She also refilled her glass.  Sitting down right next to me, she clinked my glass and said, "To love."  "To love," I agreed.  Andrea seemed to know precisely what I needed in that moment.  She sat quietly with me as we sipped our wine.  She talked to me about what an expression of love my support for my cheerleader's relationship with Randall was.  And she also emphasized how obvious it was that my cheerleader loved me for the gift I gave her.  She told me that not many men could give what I was giving her.  But not many wives could give me what my cheerleader was giving me either - the freedom to be what society wouldn't accept from me - a feminine creature who needed to let herself shine.  In other words, she explained, while it might be difficult, at times, for me to accept my cheerleader's newfound appetite for another man, I needed to know that there was a true quid pro quo in play between me and my cheerleader.  
 Andrea and I drank and chatted the evening away.  I was glad that she was there to help me occupy my mind.  Otherwise, I would have probably sat around thinking about everything that had happened and wondering what my cheerleader and Randall were doing.  Near eleven o'clock Andrea excused herself to bed, but told me I needed to wait up for my cheerleader and Randall, in case they wanted anything when they got home.  She told me I could come to her room to sleep if my cheerleader didn't need me for anything.  I sat alone in our den waiting for my cheerleader and her man to get home from their date.  Fortunately, I didn't have to wait much longer.  Just before midnight the doorbell rang.  I could hear my cheerleader laughing on the other side of the door as I approached to let them in.  When I opened it she greeted me, " Oh Sissy!  Thank God you're awake!  I forgot my house key!"  I curtsied and said, "No Mistress.  I was waiting up for you.  Can I get either of you anything?"  My cheerleader declined, but Randall wanted water.  As I went to get it my cheerleader told me to bring it upstairs to their room.  Their room!  Not our room.  Their room.  
When I got to my room I nearly opened the door and walked right in.  But then, at the last second, I stopped and knocked.  My cheerleader answered, "Come in Sissy."  When I opened the door she was standing by our bed struggling to unzip her dress.  "Help me with this?" she asked.  I could hear Randall moving about in our bathroom.  I set his glass of water on the table by our bed and then carefully unzipped my cheerleader, who shrugged her arms out of her dress and let it fall to the floor.  "My stockings?" she asked.  I squatted to remove her stockings for her as she stepped out of her heels.  My cheerleader, who had worn no bra or panties on her dinner date, stood naked before me.  She pulled me close to her nude body and kissed me tenderly as she stroked me near my chastity cage.  "Thank you for tonight Sissy.  I hope you know how much I appreciate this freedom you are allowing me."  I smiled uncomfortably, because while it was nice hearing her say so, I knew that in a matter of seconds a man was going to walk out of our bathroom and take possession of my naked cheerleader.  And I was going to let him.  She must have noticed my discomfort because she asked me if I was alright.  I tried to assure her that I was fine, but not very convincingly.  As if sensing I needed it, my cheerleader kissed me warmly and lovingly, her hand drifting to my bare bottom and touching the plug inside of me.  "It's okay baby," she whispered in my ear.  "I love you.  Maybe more than ever.  What you've given me means so much.  I'd almost forgotten how it feels to be so filled."  I realize she was attempting to reassure me of her love, but her last statement hit me.  She'd almost forgotten how it felt to be filled?  What did that mean?  I let the statement pass at the time, but we would return to it later, after this weekend passed.
As we were standing together, her naked and me nearly so, Randall exited our bathroom.  Stark naked!  In all of his magnificent glory.  God!  He really was quite well hung, as they say.  My cheerleader looked from me to him and smiled.  "Come here," she said to him.  Still holding me near to her body, she took him in her hand, and then directed my hand so that we were holding his impressive member together.  It was, without a doubt, one of the most humiliating, and yet, erotically charged moments I'd ever experienced.  Then, releasing her hand, leaving only my manicured fingers wrapped around Randall’s cock, she asked me, "Feel how heavy he is?"  Completely embarrassed at what was happening - Randall, my cheerleader, and me standing within inches of each other - her talking openly to me about his size, I nodded.  "Try to imagine how he feels when he is inside of me.  It is amazing honey!”  I smiled awkwardly, not knowing if, or how, I was expected to respond.  "You have given this to me baby.  And I love you for it."  So, there it was.  The three of us together, Randall's huge cock in my feminine hand, the contrast of his size next to my exposed caged penis remarkable.  
Next, as if to complete the circle of understanding we had with each other, she asked, "Suck him for me?"  The two of them were watching my reaction.  "Please?  I want to watch you suck him."  Another moment of decision for me.  At the time I didn't think it through in the way I'm relating it now.  And now, it is too late to rethink it and do it any other way than how I chose that night.  That night, following my cheerleader’s request, I sunk to my knees, face to face with Randall's, by then, rock hard cock, my cheerleader's excited and glistening pussy visible in my periphery, and began to fluff Randall for my cheerleader.  I admit this freely now, but only to tell this important part of my sissy journey with my cheerleader.  But I experienced an enormous sense of emasculation as I dropped to my knees that night, submitting to my cheerleader's instruction and her man's cock.  Once in motion, I took my time, treating his cock like a most precious gift.  I licked him from tip to base, lingering on his ballsack, stroking him with my tongue up and down until he was slick with my saliva.  Alternately, I opened my mouth and took him inside, each time swirling my tongue around his thick head, feeling his deep ridge, then licking him again.  At some point I felt my cheerleader gently place her hand on the back of my head, as if to guide me and keep me in place, though it wasn't necessary.  Randall was grunting his appreciation throughout.  He was sooo hard!  And so ready for my cheerleader.  After several minutes she told me to stop.  
She bent herself forward over the edge of our bed, presenting herself to Randall for rear entry, and told me to put him inside of her.  I rose from my knees and Randall moved into position behind her.  Taking him in my hand again, I directed him inside of my cheerleader, her pussy lips moist and swollen, ready for her man.  As he parted her lips, she swallowed him easily, moaning as he penetrated her completely.  "Oh!  Oh!  Oh!" she exhaled.  "Sissy!  Thank you!"  Then, as I stood by, not really knowing what was expected of me, I watched from inches away as Randall began fucking my cheerleader even more aggressively than he had earlier in the evening.  The leverage he had over her body as he pressed one hand onto her back, holding her face down on our bed, permitted him to pound her in a most vicious manner.  But I didn't need to be concerned for her.  She made it clear that she loved every second of his dominance.  I was stunned at what I was witnessing.  To see one's wife being taken in such a manner by another man is an event like no other that a man could witness.  And yet, my sissy self was helpless to change the course of events.  This was done.  I still remember the moment when I knew he was pumping his seed inside of my cheerleader.  Each individual, deliberate thrust, accompanied by his animal grunt and her equally base feminine squeals of appreciation, sent home the message that I'd just been shown how it was done by a man.  Randall was in every way an alpha.  I was in every way a beta.  And my cheerleader was the beneficiary of each of us.  When he finally stopped, each of them physically spent, he withdrew from her, his cock covered in thick, milky cum.  Still breathing heavily, my cheerleader told me to clean him, and so I went to my knees again and licked him clean, my humiliation for the evening nearly over.
 Then, turning around, my cheerleader pointed to her pussy, already leaking Randall's cream.  Still on my knees, where I belonged really, I licked and sucked my cheerleader clean.  "Thank you Sissy," she said sweetly.  Then, dismissing me, my cheerleader told me, "You can sleep with Andrea tonight.  Okay?"  I was disappointed, but couldn't have possibly explained why.  Did I really think she and Randall would want me to spend the night with them?  Obviously, my cheerleader did not intend for that to happen.  And so, having completed my service to my cheerleader and her man, I curtsied and said, "Yes Mistress."  As I turned to leave, I heard Randall slap my cheerleader playfully on her butt and say, "Get in that bed woman.  Time for Round Two."  "Oh my!" she squealed as she jumped onto our bed.  As I closed the door Randall said, "Goodnight Sissy," like it was just as natural as it could be to dismiss me in that manner.
I quietly opened the door to the room where Andrea was sleeping, but found her awake, reading, when I entered.  She gave me a knowing smile, as if she knew what had probably just happened. She offered to help me remove my corset, which I was actually thankful for.  She was wearing a black babydoll, but pulled it over her head revealing her full breasts to me as she beckoned me in beside her.   I was exhausted when I finally crawled into bed and was actually thankful that Andrea was there so I wouldn't have to sleep alone.  She asked if I was okay and I shrugged, not knowing what to say.  Andrea patted me reassuringly, almost as though I were her pet, and told me I'd done well tonight.  Then, she nudged me in the direction of her thighs, and I knew there was one more person in my house who was going to have an orgasm before going to sleep.  Meanwhile, I was suffering from a severe case of blue balls resulting from my near constant, but unrequited release.  I licked and sucked Andrea to multiple orgasms before she finally let me stop.  She then kissed me on my cheek and told me to get a good night's sleep so I would be ready for the next day.  We cuddled and soon I was asleep.
Andrea woke me early in the morning.  She was going to help me dress for the day.  I needed to prepare breakfast in bed for my cheerleader and Randall.  As I showered I wondered what an entire Saturday of serving my cheerleader and Randall would be like. Would it be a typical, lazy Saturday?  Or would I be working all day, attending to their whims?  I would soon find out that it would be nothing like I imagined.  In fact, I don’t think even my cheerleader realized what this Saturday with Randall in our home would be like.  I will say this though - I haven’t had to spend another one quite like it since, and I am thankful for that.
After I showered and Andrea applied fresh makeup to make me look as feminine as possible, she gave me a pair of sheer black pantyhose to wear.  No panties.  The result was, to me, the most embarrassing way a sissy can contain her clit - all scrunched up and yet, visible to reveal how tiny it is - especially so when locked in a chastity cage.  She helped me into a strapless, waist-length, full-cup black lace bra, to help keep my tummy tucked firmly.  The uniform of the day was a form fitting satin pink maid's uniform - very short - with an alternating black and white lace petticoat.  My pink paten leather heels I’d worn the night before completed my uniform.  As Andrea twirled me to inspect her handiwork, I realized that the dress and petticoat was not long enough to cover my pantyhose exposed ass and penis.  Thus, throughout the day I would be on display.  I didn't say anything though.  I realized it was pointless, unless I was prepared to put my foot down and end the entire weekend, which I obviously was not capable of doing.
Andrea then gave me my instructions for serving Randall and my cheerleader breakfast.  Before she sent me on my way though, she let me know that the day might prove challenging to me.  But, she emphasized, she would not set up any challenge for me that was not either safe or within my capabilities.  I was confused as to why she made that point to me then.  But later, as events unfolded, I realized what she meant.  I felt strangely comfortable and at ease downstairs in our kitchen, alone, dressed as such a sissy, moving about preparing breakfast.  I even was looking forward to serving my cheerleader and Randall in their bed.  I don’t know how to explain how I felt.  I was tormented that my cheerleader had so thrown herself at Randall.  On the other hand, I felt a sense of satisfaction at seeing her so happy.  When I had everything prepared, I set up a silver tray with coffee and muffins and carried it upstairs to my bedroom, preparing myself mentally for how I may find my cheerleader and Randall.  I knocked on the door and heard Randall’s voice say, “Come in Sissy.”  Carefully holding the tray so as to not spill the coffee, I turned the knob and stepped inside.  Randall was sitting up in the bed alone, nude, his soft, but still large cock, laying limp across his thigh.  You might think that I would try to not look at such a thing, but it seemed that it was the only thing I could look at.  He was sooo big, even soft.  And he made no effort to conceal it from me.  It was as though he wanted me to have to look at it.  I saw him smiling as I stared at his cock.  “Good morning Sissy,” he spoke, breaking the uncomfortable silence.  I remembered my instructions from Andrea.  I curtsied.  “Good morning Sir,” I replied.  “I brought you coffee and muffins.  How would you like your coffee?”  “Black Sissy, thank you.”  I set the serving tray down and poured Randall his coffee.  As I handed it to him the bathroom door opened and my cheerleader walked out.  Both Randall and I looked toward her as she entered the bedroom.  She was wearing a sheer light blue cover that was hanging open, revealing her breasts and smoothly shaved pussy as she walked toward me.  When she reached me she stopped, moving her hand to my pantyhose exposed ass and kissed me on the cheek.  “Good morning Sissy,” she smiled.  “You look cute today.”  I dipped into a curtsy and answered, “Thank you Mistress.  Would you like some coffee?”  “Please,” she said,  and so I prepared her a cup the way I knew she liked it.  As I stood by holding her cup, she climbed onto the bed, crawling over Randall to sit beside him.  As I handed her cup of coffee to her, she casually let her free hand lay on top of Randall’s cock, causing him to twitch.  He looked at her as if to say, ‘You want it again?’  Her devilish grin as much as said, ‘Yes.’  I then placed muffins for each of them on a plate and handed them to Randall.  I didn’t know what I was supposed to do at that point, so I just stood there, feeling uncomfortably foolish as Randall fed my cheerleader her muffin while she fondled his cock, which was growing larger right before my eyes.  I found, again, that I could not avert my eyes from him.  My cheerleader was looking at me with interest as I stared at her hand massaging her man’s cock.  “Have you had breakfast yet Sissy?” she asked casually.  I thought, ‘Thank God!  She’s going to tell me to go eat.’  “No Mistress,” I answered.  “Come here,” she said.  I looked at her, wondering what she intended.  It was pretty obvious though.  “Suck him,” she told me.  I hesitated, and she repeated, “Suck him Sissy,” as she directed his cock toward me, indicating that I should take him in my hand.  His cock was throbbing in my grasp as I prepared to follow my cheerleader’s directions.  I slowly began to please him, first licking him, making him wet all over.  As I continued, I sucked him into my mouth, aware out of the corner of my eyes that Randall and my cheerleader were intently watching me as I sucked his cock for her.  I was waiting for her to take over, as I assumed she intended for me to prepare him to fuck her again.  But that was not her plan.  I know what it feels it like right before a man cums, and I could tell that Randall was on the verge.  I glanced to my cheerleader, expecting her to stop me.  Instead, she encouraged me to continue.  “Don’t stop Sissy.  I want to watch you take him.”  In a matter of seconds Randall grunted and shot the first jet of his semen into my sissy mouth, the first time I had ever taken cum directly from a man’s cock.  I will never forget the feeling of his hot cum filling my mouth and running down my throat, nor the gasp that escaped my cheerleader’s mouth as she watched her sissy husband swallowing her man’s sperm.  He quickly followed with several rapid blasts as I continued to suck his cock, no longer needing my cheerleader to encourage me.  I wanted it for myself as much as I wanted to please her.  I continued to suck him after he completed his orgasm, sucking even more of his thick jizz out of the end of his thick cock.  I know that we say that eye contact is important, but in the middle of this blow job I became lost and was not aware until I finished how intently Randall and my cheerleader were watching what I’d done.  They both seemed mesmerized at me when I finally allowed his softened cock to escape my lips.  My cheerleader leaned over Randall’s waist and kissed me full on my mouth, her tongue tasting his flavor.  When she stopped, she looked at me and said, “You can go now Sissy.  Thank you sweetie.”  And so, again, right after I performed for them, I was unceremoniously dismissed, leaving them to be alone. 

In a haze following what I’d just done, I went downstairs where I found Andrea sitting at our kitchen bar drinking coffee and eating a muffin.  She looked at me, as if sizing me up.  “Everything okay?” she asked.  I didn’t know how to respond.  I’d just sucked a man’s cock and he came in my mouth.  While my cheerleader watched and encouraged me.  Three times in less than 24 hours I had taken Randall’s cock inside of my mouth!  I didn’t think these thoughts specifically at the time, but what did I think was going to be the result of this?  I was more than my cheerleader’s cuckold by this point.  I was a cocksucker.  And as many times as I’d lived the fantasy with my cheerleader, I would never have thought that she would be the one who seemed so taken by seeing me with a real cock in my mouth.  But there could be no doubt that she did like watching me suck dick.  Now that we’ve gone down this path, I’m glad that she does.  It permits me to be involved with her and her lovers.  Plus, I do like the feeling of a cock in my mouth, although only in my feminine persona.  I realize my cheerleader’s men may understand that a male is sucking their cock.  But to me, I’m a woman sucking their cocks.  But I’m getting ahead of myself.  This weekend was long from being over.  “I suppose,” I answered.  I felt as though Andrea had a general idea as to how events were going to unfold, even if she didn’t know precisely how they might end up as they developed.  And she always seemed to know what to say to me for reassurance.  “Don’t overthink things Sissy.  You are doing fine.  Just remember what your role is this weekend.  You serve your wife.  It’s that simple.  This is new to her as well, so you need to make it easy for her.”  So there it was.  The weekend was long from over, and I needed to buck up and take what came along with a cheerful frame of mind.  Just then my cell phone rang.  It was my cheerleader calling me.  When I answered, “Yes Mistress?” she said, “Will you please come upstairs Sissy?  I need you.”  “Yes Mistress.  I’ll be right there,” I answered and hung up.  I began to walk away and Andrea stopped me.  “Sissy.  You need to pay better attention to your responsibilities.  Whenever you enter the presence, or leave the presence, of anyone, you must curtsy.”  I said, “Yes ma’am,” and dipped into a curtsy for her.  It really was something I had difficulty remembering.  It was also something that constantly reminded me that I was a sissy, so I understood why Andrea insisted upon it.
I knocked on my bedroom door and waited for my cheerleader to tell me I could come in.  I assumed she and Randall might want fresh coffee.  I opened the door after she said, “Come in,” and entered, pausing to curtsy.  My cheerleader was lying in our bed, alone, still wearing the blue robe.  Randall must have been in the bathroom.  “Come here Sissy,” she said.  I walked to the side of the bed and asked what she needed.  “I need you,” she said sweetly.  She beckoned me to lean toward her and she kissed me softly on my mouth.  “How are you?” she asked.  “Fine,” I said.  “Is this what you wanted?” she asked me.  I wasn’t sure what she meant.  Kissing her?  Or something else?  “What do you mean?” I asked.  “You know.  Me being fucked by a big cock.  You sucking cock.  Is this what you wanted?”  I really did not know how to respond.  It had been my fantasy to start with.  I could not argue with her on that point.  But I wasn’t sure how I felt now that it was happening.  I had not fantasized it in quite this way.  And I was still confused at eagerly my cheerleader had taken to it.  I ended up responding with a question.  “How about you?  Are you happy?”  She smiled.  “Yes Sissy.  I am.  Very.  Thank you.”  I told her, “Then so am I.”  She pulled back her gown to uncover her breast.  “Randall left something for you.”  I looked and could see her breasts were shiny wet where he had cum on her.  She nudged my head down.  Compliantly, I leaned down and began to lick and suck her breasts clean. My cheerleader sighed and moaned as I sucked her nipple into my mouth.  I know she likes it when I bite her nipple gingerly, and so I did that for her and she reacted as she usually does, tensing up and groaning her appreciation.  She then nudged me lower, toward her pussy.  When I got there I could see that cum was leaking from her, and I knew that Randall had fucked her again this morning.  I began licking and sucking her clean, and as I did she let her legs fall open to grant me better access.  As I usually do, once I began servicing her pussy I became lost in the endeavor, until I noticed something move in my periphery, and realized that Randall had come out of the bathroom and was standing by us watching me pleasure my cheerleader.  She soon began having an orgasm as I finished her off with Randall watching me.  When I finished, I felt embarrassed that I had done it with him standing there, but it seemed I could do nothing about it.  He was there, and that was that.  “Thank you Sissy,” my cheerleader said.  “You may go now.”  I said, “Yes Mistress.”  I curtsied and then left them alone.
Andrea was not downstairs when I got down.  I began moving about the kitchen cleaning up after breakfast.  In a few minutes I heard steps.  Andrea and my cheerleader came into the kitchen together, each dressed as if they were going somewhere.  I remembered to curtsy when they entered the room.  My cheerleader smiled as I did.  “We’re going shopping Sissy,” she told me.  “Will you please do laundry and change the bed sheets today?”  What was I going to say?  Andrea had told me what my role was.  “Yes Mistress,” I replied.  “Thank you.  We won’t be long,” she said as they walked out.  Once the door closed the other shoe dropped for me.  Randall was coming downstairs.  I was alone with him.  Was he going out?  I prayed that he was.  I didn’t know if I could bear to be alone with him all day.  My prayers went unanswered.  He was wearing a pair of gym shorts and a t-shirt.  He wasn’t going anywhere.  I curtsied when he walked into the kitchen where I was still cleaning.  “Is there any coffee left?” he asked.  “No sir,” I told him.  “Would you like some?”  He told me he would and walked into our den and turned on our television.  When I brought him his coffee, black, he was watching the Saturday pre-game sports program, College Game Day, on ESPN.  He thanked me and continued watching television.  It appeared that Randall was settling in on a Saturday of watching college football.  “Can I get you anything else?” I asked.  “No,” he said.  “Go ahead with your chores.  I’ll let you know if I need anything.”  Go ahead with my chores?  He was aware of my duties?  And he was treating me like the servant I suddenly felt like.  “Yes sir,” I answered, and curtsied before leaving him.
I was in a fog at this point.  Randall had been in our home less than 24 hours.  He’d fucked my cheerleader I didn’t know how many times.  I’d sucked his cock three times.  Now, my cheerleader and Andrea had left me alone with him and he was treating me like hired help.  My embarrassment and humiliation was only exceeded by my irritation at how I was being treated as a servant.  It was soon going to get worse.  I went about following my cheerleader’s instructions.  I stripped the beds and carried the dirty sheets to the laundry room to wash them.  While the laundry was running, I took clean linens out of the linen closet and began remaking the beds.  Then I retrieved the dirty clothes from our hamper and went downstairs to wash everything.  I moved the sheets to the dryer and loaded the washing machine with the dirty clothes I could wash in the machine.  While that was running I hand-washed my cheerleader’s and my soiled lingerie.  I actually felt a sense of relief to be out of Randall’s presence.  I don’t know why, but it just felt even more embarrassing to be alone with him dressed as I was.  I felt like he was looking at my sissified state and enjoying knowing the role he had played in making me so.  
I could hear the game on in the den as I moved about doing my chores.  The laundry was well underway and everything else was pretty straight, so I felt like my cheerleader would be satisfied when she and Andrea returned home, which I hoped would be soon.  As I was moving about, the front doorbell rang.  Randall called out from the den for me to get it.  I froze.  Was he expecting someone.  I went to the den and asked.  He told me he was expecting a few friends to stop by and watch the games with him.  I was stunned!  He had invited friends over?  Immediately I wondered if my cheerleader knew.  I said, “I can’t answer the door like this!”  Randall looked at me like he was highly amused.  “Sure you can.  They won’t be surprised.  I told them about you.”  My mouth dropped open.  I couldn’t believe this!  I had agreed to a lot.  But I did not agree to this.  Or had I?  What was I going to do?  I felt like we were having a stand off when the door bell rang again, this time repeatedly, as if whoever was there was becoming impatient.  Randall met my eyes and said very slowly, in a way that indicated he was not going to tolerate disobedience, “Answer the door Sissy.  Invite my friends inside.  Offer them a beer.  Now go,” he ordered me.  I hesitated, then thought of what Andrea had told me.  I was serving my cheerleader this weekend, and all that that entailed.  And she had told me she wouldn’t subject me to anything that wasn’t safe.  So I had to figure she knew about this.  These would be strangers.  They already knew about me.  How bad could it be?  I had to go through with it.  I dipped into a curtsy and said, “Yes sir,” and turned to go answer the door.
When I opened it there were three guys standing on the other side.  All six eyes locked on me immediately.  They had obviously been briefed and were anxious for their first look at the sissy.  I forced a smile and curtsied.  “Hello gentlemen,” I whispered in a soft, feminine voice.  “Won’t you come in?”  They responded mostly in a polite manner and walked in, all watching me as they did.  “Mr. Randall is in the den,” I told them.  “May I get you something to drink?  Beer?”  They all said beer sounded good and so I directed them to the den and asked Randall if he wanted a beer also.  He did, and so I curtsied and went to get each man a beer.  I could hear the chatter as the three guys were obviously reacting to their first impression of me.  They stopped talking when I entered the room with the beer, so I knew they’d been talking about me.  I served their beer, aware that I was the focus of all of their attention, not that I could blame them.  I was completely humiliated knowing that all of them knew I was a man dressed as a sissy.  And to make matters worse, the short maid’s dress I wore did not conceal my chastity locked penis on full display under my pantyhose.  I wondered if my cheerleader had known this was going to happen.  I had no doubt that Andrea was aware.  I even suspected she had orchestrated the display.  Her goal was clearer and clearer.  I was being made to accept my sissy self and in a most public manner.  What could be worse than having to serve a bunch of men beer while they watched football, something I would normally be doing on a Saturday afternoon, all the while dressed as a sissy maid?  I soon found out.  
I continued to serve them beer throughout the day, wondering when my cheerleader and Andrea would get home to bring me some relief.  Around five they returned, but not alone.  Apparently, and this let me know my cheerleader did know what was going on, they had met up with two of Randall’s friends’ girlfriends, because they were in tow with Andrea and my cheerleader.  I assume you all know what a group of women who have been hanging out for a few hours sound like.  Yeah.  When they came in they were chattering and laughing with each other, and the new girls were all anxious, in was obvious, to meet the sissy.  Suddenly, I found myself thrust into the role of being the sissy maid to serve my cheerleader and her guests for a party at our house.  I wanted to run and hide, but was so disoriented from the rush of the moment that I couldn’t do anything other than react.  My cheerleader greeted me, “Hi Sissy!  I have some new friends to introduce you to,” moving me past my shock at what was unfolding.  I stood there like a deer caught in the headlights.  Andrea was watching me.  With a move of her head she reminded me to curtsy.  I dipped.  “Yes Mistress,” I weakly replied, wishing I could disappear.  The two women were mesmerized.  Clearly they had been told something, but whatever they’d been told had not fully prepared them for the sissy standing before them.  But, as women are wont to do, they greeted me warmly as I was introduced as my cheerleader’s husband.  Andrea took control long enough to get things moving along, asking for drink orders from the women.  Then, as my cheerleader showed them into the den, Andrea stayed behind to help me with their drinks, but more likely to help reorient me to what was happening.  

She came to me and said, “Not bad Sissy.  You handled that quite well.  Now all you have to do is go with the flow and you’ll survive the evening.”  I looked at her for an explanation.  “Why?” I whispered.  “It’s simple Sissy.  You, and your wife, need to become comfortable being around each other with you in this role.  These people don’t know you.  They know Randall and me.  And they understand their role tonight.  This is not shocking to any of them.  You can let yourself go, even if you feel embarrassed.  You can do this.  Let go.”  And so began an evening I will never forget.  I did, indeed, let go.  And in doing so, I let my cheerleader let go as well.  I fell into my role as the maid and served them drinks and chips.  As dinner time drew near, they all got together and ordered Chinese food to be delivered, which I served after having to answer the door for the delivery boy, dressed like a sissy.  I am pretty sure he was even more embarrassed than me.  Throughout the evening my cheerleader was all over Randall as he treated her as his personal possession.  I realized his actions were part of Andrea’s design.  As for my cheerleader, well, I couldn’t fault her.  Her husband was dressed as a sissy and playing the role to the hilt, complete with curtsies and ‘Yes ma’ams’ and ‘Yes sirs,’ all evening long.  She naturally gravitated to the alpha male.
When the final game ended a little after 11 p.m., the guests began excusing themselves.  Everyone was very polite and thanked me for my service.  The two women were especially sweet as each hugged me and kissed me on the cheek.  One even whispered in my ear how pretty she thought I looked.  I thanked them and we said our goodnights.  My cheerleader, Randall, and Andrea excused themselves to bed.  I was left to clean up before going joining Andrea in bed.  I was not invited to my cheerleader’s bedroom that night.  And I found my reaction odd.  I wasn’t happy about it.  I liked it better when I was involved.  This felt like I didn’t matter.  I finished cleaning up and then went to change out of my uniform.  I took off my clothes and put on the nightgown Andrea had laid out for me on the bed.  I went to the bathroom and washed off my makeup before going to bed.  When I crawled into bed I was exhausted.  Really exhausted.  Andrea seemed to understand and let me cuddle to her.  “You did splendidly today Sissy.  I couldn’t be more pleased.  And I think if you are honest, you are pretty pleased with yourself too.  Aren’t you?”  She looked at me expectantly for my response.  I did not want to admit that she was correct.  But she seemed unwilling to permit me avoidance.  “Hmmm?” she asked.  “I suppose I am,” I finally admitted.  “And that is what I expect from you in the future when your wife has a man over.  And what she’ll be expecting too,” she added.  Men?  I asked, “Men?”  Andrea seemed perplexed.  “Yes Sissy.  Do you think this is going to end?  Now that she has had a taste?  You’ve given this to her.  You can’t take it back now.  Not without consequences.  I assure you, Randall won’t be her last.  Your job is going to be to make it work for her.”  I was truly stunned.  But, looking back on it, I should not have been.  I did open this door.  I couldn’t possibly close it now.  
Before we went to sleep I went down on Andrea for what would turn out to be the last time.  She obviously knew that as well as she made me pleasure her for a very long time.  As I licked and sucked her, she was manipulating the plug inside of me, tormenting me beyond belief.  She had several orgasms that night before finally permitting me to stop and to snuggle with her.  The next day was a day like no day I could have imagined.  I’m leaving for a separate installment the description of what happened to me on my cheerleader’s and my final Sunday in Andrea’s company.  Stay tuned.  And please don’t be upset with me over the cliffhanger.


Leeanne (a thoroughly cucked sissy husband)


  1. Such a lovely installment of your story Leeanne!

    Every time I think you can't cross another barrier, you seem to sail past and I can't wait to hear about your Sunday. I also have to say that at the heights of personally being Caitlyn I always had one last refuge for Calvin.... Saturday Football. Reading about you dolled up and serving as a sissy maid during that time really hit home with me.

  2. Dear Caitlyn,

    When I started my blog almost two years ago, one of the main reasons was that I had decided to tell about my sissy journey, starting from the very beginning. A lot of what I'm telling now had just begun occurring, including my cheerleader's and my experiences with Andrea and Randall. So, I always knew that, if I carried through with telling it all, this was coming. I've been worried about reactions because, looking at my story from an outside perspective, I realize that I must seem a weak man. But the thing is, although I was the one who got my cheerleader fantasizing about other men, I had planted a thought inside of her that, I now understand, had to be released. And you are correct - that Saturday serving Randall and his friends while dressed as a sissy - was so hard for me. It was one of the moments when I knew I was a lost cause in some respects. I could not return to feeling much like a man inside, although I do still watch sports all of the time. My cheerleader and I have always enjoyed that part of our lives. I guess what I'm saying is that I began seeing myself differently after that weekend - especially so after the Sunday my cheerleader and I spent alone with Andrea.

    Thanks for your support Caitlyn.



    1. I still find it surprising that you could ever think that anyone would look upon you as a weak man Leeanne. I'm sure there are some prehistoric neanderthals out there that might only see you as a weak man, but for the entirety of your audience here, and dare I say the majority of people everywhere, can only look upon you and marvel at your immense inner strength.

      Many of us have, or at least have had, fantasies of being a true sissy. Sometimes it's just the figment of a dream when we wake and other times it's a heartfelt desire that feels like it will break us in two. But where we continue to sit and read about your story and pooh pooh away thoughts of making our fantasy into reality, you are living it out. I know that I don't have that kind of strength, and I doubt that I ever had that type of fortitude. I can only hope that I will one day have half of your strength when it's needed in my life.

    2. You know Caitlyn dear, if you were here with me, right now, I might feel compelled to show you some special sissy appreciation. You are so nice!

      Kiss kiss,


  3. I can't in any way imagine a more ideal situation that how you describe your cuckolding experience w/ your cheerleader. It just sounds perfect!

    1. The love is what makes us so perfect. My cheerleader is such an amazing woman. And perhaps even more so now that she has crossed the line to experiencing so much pleasure from men.

  4. Leeanne:
    I have read all of your wonderful stories...and have followed your blog with severe devotion. I have the greatest respect for you as a sissy. You have walked the walk so to speak......and have brought us into your world and shared your innermost feelings. My dear, I adore you so much. Yes, it's true, you can never go back to being a man ever again. I've been there myself..... as you've opened one door, you also shut and locked another.
    Love always

  5. Leeanne,

    Can you tell me where I can find those older posts (do you know the date range)? I want to read your stories in order, so I have to find them first.

    I'll copy them into a word document so I can keep them in order and read them like I read Sara Desmarais' stories.


    1. Each preceding post is linked, in order, at the beginning of each successive post. I've done that throughout for easy reference to new readers.

  6. Thank you sooo much for sharing your story. It is perhaps the most exciting progression into submission i have every read. If my Mistress would allow it i would gladly jerk off over and over to it...and, of course, lick it up. But, as an owned subhubby, i am just fortunate that She lets me read your blog. Still, the titillation is delicious. Please keep your story coming!

    1. Thank you didon. I wonder, does your Mistress read my sissy blog?

      Kiss kiss,