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Cheerleader and Sissy Are Mentored

So, it happened.  My cheerleader had cuckolded me.  She had evolved from being upset about learning that I liked to wear women’s lingerie, to accepting my confession that I was consumed with feminine feelings as an alter ego, to enjoying our little fantasy world, to actually fucking another man, or, as I now say simply, a man, whose cock and really, male attitude, was more satisfying to her than I was.  I should emphasize here that nothing that happened over the next few months, and up to the present, diminished her love for me.  And I continue to bring her sexual pleasure.  The crucial difference is that she now enjoys an added element of sexual pleasure that she hadn't before we made our sissy journey together.  And of this particular point I am 100% certain - if I had never brought her in on my panty secret - if I had simply remained in my private fantasy world - my cheerleader would have never dreamed of going where we have gone.  So, for everything that has occurred, I accept responsibility.  And while what I am about to describe was the most difficult, often humiliating, time I have been through in my life, I can tell you now that I am so happy that I have made the journey.  And why?  Because, as I note in the first few sentences of my blog description - I am a sissy and I have been all of my life.  I simply didn't always know it.  But a sissy who lives in denial is a tormented person.  Now, my cheerleader and I can openly share our experiences together, and she has the best of both worlds - a man when she wants to be fucked - and her sweet sissy husband to pamper her and to love her tenderly after the raw sex is done.
Once the cucking happened, even though my cheerleader didn't fully realize when it happened what she'd done to me, things began to move at a faster pace than either of us realized they would.  Randall was invited to dinner again the next Friday evening.  My cheerleader and I had a pretty normal week.  I was apprehensive about the next meeting with Randall though.  She had indicated that she intended for me to be an active participant this time.  And while a part of me wanted that, another part of me was relieved that I had not been called upon the previous Friday to suck Randall's cock while my cheerleader watched.  I believe that I would have been too embarrassed to do so. 
 The Thursday night before Randall was due to visit us for the second time, my cheerleader's iPhone rang while we were watching a television show.  She immediately popped into cheerful mode when she heard his voice.  "Randall!" she exclaimed.  "How are you?"  She then became quiet, listening to him talk, nodding, me watching and trying to piece the conversation together based upon her end of the call.  At first, I wondered if he were calling her to cancel dinner the next night, and I remember feeling an odd sense of relief and disappointment all at the same time.  After listening to Randall say whatever he'd had to tell her, my cheerleader said, "Hold on.  I'll ask."  Removing the phone from her ear, she told me that Randall was asking if he could bring a friend with him to dinner.  Trying to speak so he wouldn't hear me, I whispered, "A guy?"  My cheerleader mouthed, "I assume so.  Do you mind?"  I was completely ill equipped for her question.  Implied in it was that she wanted Randall to bring a friend.  She wanted to have a three-way with two other men.  I had no time to think about it.  Randall was on the phone waiting for an answer.  I acquiesced saying, "If you want."  My cheerleader smiled and spoke back to Randall, "Sure!  That would be great!"  They ended the call right after that and the two of us just sort of sat there and looked at each other.  Then she asked me if I was sure that I was okay with it, and that she'd call Randall back and tell him we changed our minds.  But I could see that she was excited about the possibility and couldn't bring myself to deny her.  I would just have to ride this roller coaster to the end. 
 My sense of confusion about the direction my relationship with my cheerleader was taking amped up several notches, I barely survived the next day at work.  And it was a busy one too, so I had to find a way to remain focused.  I was late arriving home, so my cheerleader was already dressed and in the kitchen making final preparations when I walked in.  I apologized for running behind.  She told me not to worry, but to go shower and change - that she'd laid out clothes for me to wear.  Since it was already after 6:30 by then, I quickly went upstairs to get ready.  Lying on our bed was a pink, outlined with black lace, panty, bra and garter set, and black stockings.  My male disguise was a pair of grey trousers and a black half-mock turtleneck sweater.  I quickly showered and shaved, and then began donning my cheerleader's latest purchase for me.  I wondered what she had bought for herself.  She’d been wearing a very tight, grey, a-line skirt and red sweater when I’d walked in.  Not to mention very high heels.
 I was just fastening my stockings to the garter clips when the doorbell rang.  I paused and listened as my cheerleader's heels clicked across the hall floor downstairs to greet our guests.  Almost immediately, I realized that the voices my cheerleader was greeting were not the voices of two men, but instead, Randall and another woman.  Randall's friend was a woman!  What was going on?  He'd brought a date?  I was even more confused.  My cheerleader called up to me to hurry, that our guests were here.  I told her I'd be right down.  Nervous energy coursing through me, I quickly finished dressing.  Then, filled with apprehension, I walked downstairs to join my cheerleader and our guests.
Randall greeted me warmly, extending his hand to shake mine.  He then introduced me to his friend, a very attractive dark-haired woman, who I figured for being in her mid-forties.  That would make her younger than my cheerleader and me, but still a mature woman.  She was wearing a tight, short red skirt and a tight white top, through which you see that she was wearing a black full cup lace bra beneath.  Her name was Andrea, which she was quick to emphasize was pronounced "On-dry-uh."  She greeted me with a hug and a touch of cheek to cheek, her hand noticeably touching my bra strap beneath my sweater.
 Greetings done, I offered drinks.  I asked Randall if he wanted whiskey again, and he affirmed.  My cheerleader had a bottle of white and red wine out.  But Andrea wanted a Whiskey Sour, and so I had to scurry about to find ingredients for her.  Luckily, I had what I needed and had soon delivered everyone their cocktail.  Randall, Andrea and I went to the den to sit while my cheerleader was doing a few final touches on dinner in the kitchen.  Within minutes of the three of us sitting down in the den, Andrea excused herself and went to see if she could help my cheerleader.  Randall initiated small talk with me, asking about my work and stuff.  He really was very nice to me, so as awkward as the situation still felt, I had a difficult time not liking him, even though we each now understood that he had fucked my wife.  Plus, I was assuming that he knew that I’d cleaned his sperm from her the weekend before. 
 Andrea and my cheerleader had been alone in the kitchen for a pretty good while when I noticed Randall's drink was empty.  I excused myself to refresh him and went to the kitchen.  As I turned the corner I saw my cheerleader and Andrea standing closely together near the sink, Andrea obviously speaking seriously to my cheerleader.  They stopped and turned to face me as I approached.  The expression on my cheerleader's face was one that I could not quickly interpret, but it seemed almost somber.  What could the two women have been discussing?  Whatever it was, they stopped the moment they heard me walk in.  I explained that I was getting Randall a fresh drink.  Andrea asked me to make her one too.  Actually, she didn't really ask.  She told me to make her a fresh one.  The two women stood silently by, watching me as I worked making the drinks, but their spacing remained close.  I finished making the drinks and offered the one I made for Andrea to her.  She told me to take it into the den - that they would be joining us in a few minutes.  I thought that her demeanor was odd, like she was in charge, and my cheerleader was under her control or something.  Whatever, I could sense that something was going on with this Andrea woman.
 I took Randall's drink to him and then sat back in the chair I'd been in.  We sat in an awkward silence together, me wishing the women would hurry and join us just to change the dynamic.  I was feeling a foreboding sense of discomfort.  Why was Andrea here?  I felt something was going on, but could not figure out what.  As it turns out, I was correct.
When they joined us, my cheerleader, as she had the week before, went straight to the couch where Randall was sitting and sat right next to him.  And, in what seemed a deliberate act on her part, she placed her hand on his thigh, just next to his groin, and leaned in and kissed him right on the mouth.  Despite the week before, I was stunned by her forwardness, especially in front of me and this new person, Andrea.  As my cheerleader kissed Randall, I noticed Andrea was looking directly at me, a studious expression upon her face.  The feeling in the room had taken on a tone that I don't know how to describe.  Randall's guest had turned out to be more than either my cheerleader or I could have fathomed.  It was obvious to me that her invitation to dinner by Randall was not random.
 The four of us sat together a while, engaging in social small talk, and then my cheerleader excused herself to begin getting dinner ready to be served.  Right after she left, Andrea suggested to Randall that he go to help her.  Suddenly, I was alone with this woman.  And it felt like she planned it too.  We sat together, her looking at me, as if sizing me up.  I felt so small in her presence.  What was it about her?  The next words she spoke let me know I was in trouble.  "I can refer to you as sissy?  Yes?”  I knew that I'd heard her clearly.  What I couldn't process quickly enough was why.  For Andrea's part, she continued to observe me, as if gauging my reaction to her question.  Before I could form a response, Andrea said, "Your wife has already told me about you sissy.  No need to be shy."  My cheerleader had told her?  I managed to speak and asked when.  She explained that it was when they were talking in our kitchen.  So, that was what was going on in there.  Andrea proceeded to, basically, tell me why Randall had invited her to have dinner with us.  Andrea, it turned out, was a professional Dominatrix who Randall knew.  He had asked her to come, as a personal favor, to help my cheerleader and me.  I was very confused at this point and told her so.  Andrea explained that she understood that my cheerleader wanted to keep exploring sex with men, and that she actually thought I wanted it also.  The problem, according to Andrea's assessment, was that my cheerleader did not know how to express herself to me.  Andrea explained that she was going to help us with that problem, and to lead my cheerleader to her own comfort zone as she continued to cuckold me.  The moment she said the word I must have turned red as she smiled in a knowing way.  "You do understand that when your wife fucks men with your blessing that she is cuckolding you?  Don't you sissy?"  I nodded, suddenly incapable of anything more than minimal expression.  Then, Andrea told me that she realized it was probably going to be difficult for me, and even my cheerleader, at first, but that her goal was to help us become more comfortable addressing each other, and expressing ourselves, when my cheerleader was with a man.  She invited me to ask questions, but the main thing she wanted me to do was to affirm my consent to my cheerleader's desire to be with men.  This turn of events was beyond my fantasy world, but I did admit to her that I wanted my cheerleader to have what she wanted, even though I probably could not have articulated why in that moment.  Andrea told me that for the rest of the evening, that I should stop thinking or worrying about how I should behave.  She would tell me what to do.  All I needed to do was act.  To comply.  She told me that it would be difficult for me to do so, but she assured me that if I placed my trust in her, I'd soon understand the benefit.  Short of asserting myself in some way, and objecting, I saw no other avenue.  Plus, deep within me, I think I was truly relieved to submit to someone else's guidance.  I had no idea where things were about to go, but for some reason I found myself agreeing to follow her lead.  
 
 Andrea then told me to follow her to join my cheerleader and Randall for dinner.  They were already seated at the dining room table, across from each other, and seemed to be waiting expectantly for us to arrive, as if they understood why Andrea had arranged to be alone with me.  Andrea paused by the seat at the head of the table, and addressing me for the first time in front of my cheerleader, said, "My chair sissy."  I noticed that my cheerleader's gaze was locked firmly upon me, curious to observe my reaction.  Feeling humiliated to be called a sissy in front of my cheerleader and her man, I, nonetheless, pulled Andrea's chair out and assisted her in sliding up to the table.  My stomach was in knots as I began to suffer through this first, of what would turn out to be several, moments of humiliation as I stood by while Andrea controlled and referred to me as, ‘sissy’ in front of my cheerleader and her man.  Andrea then proceeded to give me a series of instructions, from telling me to fill the wine glasses to serving each of them the meal my cheerleader had prepared.  And with each instruction, she referred to me as, ‘sissy.’  I was actually amazed how easily I seemed to grow accustomed to the constant reference, including when my cheerleader quietly thanked me when I served her, "Thank you sissy."  I sensed that even she was acting according to Andrea's instructions, and as it turned out, she was.  After I served everyone, Andrea told me to prepare a plate for myself and to join them.
How she managed, I don't know, but Andrea skillfully led us through a rather normal adult dinner discussion.  For my part, I remained mostly silent, content to not have to speak much.  Throughout the meal I was periodically asked to serve the others.  I refilled water and wine glasses.  I cleared dinner dishes and served coffee and dessert.  And each time, Andrea and the others referred to me as ‘sissy,’ when addressing me.  If her goal was get everyone comfortable calling me ‘sissy,’ it was working.  
 After dessert, Andrea stood up from the table and invited my cheerleader and Randall to join her in the den to talk.  She told me to clear the rest of the dishes and to clean up the kitchen, and to join them when I finished.  Thus was my status among the four of us established.  As I cleaned up, I wondered the entire time what was being discussed in the den.  I had to assume they were talking about me.  And the other thing I wondered was what was in store for the rest of the evening.  Needless to say, I was filled with anxiety about my fate, which I would learn soon enough.
When I finished cleaning up, I walked into the den.  My cheerleader was sitting up close to Randall, snuggling tightly to him.  Andrea was sitting across from them.  She addressed me, "All done sissy?"  I told her yes, and it was then that she seemed to begin ratcheting things up on me.  "You may refer to me as 'Ma'am, sissy."  I repeated my answer for her, "Yes Ma'am."  She stood up then and told my cheerleader and Randall to excuse us for a few minutes, and then she walked out of the den beckoning me to follow her.  As if she felt completely at home, she led me upstairs to our bedroom.  She was so matter of fact and nonchalant that I did not know quite what to make of her.
 Andrea walked into our bedroom and began surveying things.  Noticing an armchair in the corner of the room, she went toward it and sat down.  I stood in the doorway, wondering what was going to happen next.  Andrea smiled at me and told me to come to her.  I walked over, anxiety and apprehension coursing throughout my body.  I knew, deep within me, where this was going.  And while I thought I wanted it, I was also freightened as the reality seemed about to collide with my fantasy.  When I reached Andrea, she explained to me what was about to occur.  She made clear to me that it was probably going to be difficult, but that she would help me through it, if I wanted it enough.  She also emphasized that my cheerleader wanted it.  She told me that what had happened between my cheerleader and Randall the week before may have felt like something significant to me, but that what was going to happen on this night would make me realize how intense the experience of my cheerleader being fucked by a man could be.  I was nervous, to be sure, but I understood how much my cheerleader wanted this, so I made up my mind to do what was necessary.  I told Andrea that I would do as she told me to do.
 The first thing she made me do was to undress for her.  She wanted to see the lingerie I was wearing.  So, for the first time ever, I let another person – another woman - see me dressed in sexy feminine lingerie.  My fingers were shaking as I removed my male clothing, revealing to Andrea the bra and panty set my cheerleader had bought for me.  She was very complimentary on what I wore, telling me that I looked very pretty.  Then, she asked if I owned any high heels.  When I admitted that I did, she told me to get them and to put them on for her.  I was hesitant, as I never wore heels around my cheerleader.  I didn’t think she would accept it very well.  Now, it seemed, she was going to see me wearing heels.  I was worried about how she would react.  I retrieved a pair of black high heels from a locked trunk I kept in my closet.  I stored other items in the trunk that only came out when my cheerleader was away, including a few wigs, makeup, and sexy dresses.  Returning to Andrea with my high heels in hand she was smiling, and I think it was because the heels were so tall - 5 inches.  She told me to put them on for her and so, still feeling extremely embarrassed, I did so.  She had me walk a few steps in them and told me she was quite impressed at how well I did so.  She then asked if I owned breast forms, which I did.  So she told me to get them as well.  As I went to retrieve them, I was aware that this was going to be so humiliating for me.  To be dressed this way for my cheerleader and her man to see.  I slipped them inside of my bra cups before returning to Andrea.  She had me stand before her, telling me to pull my shoulder blades backward, which resulted in my breasts jutting forward in a more pronounced manner.  She complimented me on my feminine form, which actually caused me to blush.  Finally, Andrea asked me if I owned a sexy nightgown that I could wear, something preferably sheer she said, so that my bra and panties could still be seen.  Of course, I did, and so I went to my lingerie drawer and located a sheer, white baby-doll, and held it up for her approval.  She was very pleased at my selection and told me to put it on.  Once I had the baby-doll on, Andrea pointed to a spot in front of her and motioned for me to stand before her.  I was feeling overwhelmed at what she was having me do, and extremely apprehensive about how quickly things were moving.
 Andrea told me to kneel in front of her, facing her.  I slowly sank to my knees and can still feel the utter sense of submissiveness that she instilled in me.  Whatever her intentions with me were, I intuitively understood that I was in the presence of a natural Domme.  Touching me below my chin, Andrea tilted my bowed face, more out of an awkwardness born of not wanting to meet her stare, upward until I was looking directly at her.  She then proceeded to apply red lipstick to my mouth, and then eyeliner and shadow upon my eyes, and blush on my cheeks.  And I let her.  As she applied the makeup, she explained in more detail what she expected of me for the remainder of the evening.  She emphasized that she would be instructing me throughout, but she wanted to preview for me what I was going to be asked to do, so that I would be better able to comply without question.  She also explained that, what was going to occur was something my cheerleader had already affirmed that she wanted to take place, although she didn't know precisely how Andrea intended to make things happen.  But, from my perspective, Andrea wanted to be certain that I understood my role.  My tummy was aflutter with butterflies as I kneeled before this dominant woman who had just entered my life.  Could I have stopped things then?  I suppose I could have.  And I wonder sometimes what might have happened if I had balked.  How would my cheerleader have responded?  Would she have accepted what would have been a decision I, effectively, made for the two of us?  Or, would it have been the beginning of the deterioration of our marriage?  It is pure speculation now, I realize, for I did not balk.  But the next two hours of our life really did cause a seismic shift in our relationship forever.
Ground rules established, Andrea gave me my next set of instructions – instructions that involved me acting, from outward appearances, on my own.  Andrea was going to wait in our bedroom for me to return with my cheerleader and Randall, or, as I was to refer to him for the rest of the evening, Mr. Jones (not his real last name).  As I recount the rest of this most important night in the life of my cheerleader and me, I must emphasize how almost out of body I felt as events unfolded.  It was a very tense time for me, and no doubt for my cheerleader as well, as she saw her husband in an entirely new light for the very first time.  Sure, she was used to seeing me in lingerie.  And she knew, at a deep and subconscious level, that I was a sissy.  And she had already, technically speaking, cucked me the previous week.  But this was the night when I would become a participant.  And really, even more than that, as you'll understand as I describe in detail the rest of the night.  But remember this as you read onward - I was frightened, nervous, and humiliated beyond description as I acted out my role in this drama.  But I acted on faith.  Faith that my cheerleader wanted everything to occur just as Andrea described.  And faith that Andrea knew the best way for this step in our relationship to take place.
 My walk down the stairs in my high heels seemed to take forever.  As I was carefully walking down them, holding onto the rail as I went, I rehearsed in my head what Andrea had told me to do and say.  Aware that my cheerleader and Randall could probably hear my footsteps clacking on the hardwood stair treads, I wondered how they were going to react upon seeing me.  My cheerleader, seeing her husband for the first time in high heels, wearing makeup, and being seen in front of another man for the first time dressed femininely.  And this man, Randall, seeing another man appear before him dressed as a sissy.  All of these thoughts and emotions combined to push me nearly to a point of emotional overload.  And yet, I walked toward my fate, one short high-heeled step after the next.
As I turned the hallway corner at the foot of the stairs and began my walk toward the den where my cheerleader and Randall were waiting, I saw my cheerleader cuddled snugly to Randall's side, her face nuzzling into his neck.  He saw me first and I don't even know how to describe the expression his face took on, obviously thrown by seeing me dressed as I was.  I think even he, who had obviously brought Andrea to us for a reason, was stunned.  But when my wife realized something was happening, and she turned away from his neck to see for herself, her face revealed her complete surprise.  I know she realized it was me, but it was as if she could not really process what she was seeing.  Following the directions Andrea had given, I slowly walked toward them.  Pausing as I stood before them, looking at my cheerleader, I dipped into a curtsy and then held my hand out to take hers.  "Your bed is ready Miss M."  Then to Randall I said, "Mr. Jones?" inviting him to follow us.  My cheerleader took my hand, stood, and we held each others' hand as I led them wordlessly up the stairs to our bedroom, the two of them having ample opportunity to observe me dressed as I was without me having to match their gazing eyes.
 Walking into our bedroom together, we found Andrea waiting, still seated in the same chair.  I could feel her watching me as I led my cheerleader to our bed.  Then, I turned to Randall and asked, "May I undress my wife for you Mr. Jones?"  I could see that what was unfolding was probably way beyond what he'd anticipated.  But he was grinning in a most lascivious manner, and nodded yes.  Turning to my cheerleader, I asked, "May I Miss M?"  She smiled nervously and said, "Yes sissy.  You may."
 Facing my cheerleader, I reached out and grasped the bottom of the tight red sweater she wore, and then lifted it upward over her head, revealing as I did a red lace push-up bra.  I could literally feel my cheerleader’s excitement as I undressed her for a man.  Next I reached to her waist and unclasped her skirt, lowering the side zipper, and then helped her work down the tight skirt until it puddled on the floor at her feet.  My cheerleader now stood beside me wearing only her sexy red lingerie.  She'd worn her panties outside of her garters, and so I helped her step out of them as well, revealing her full, but suddenly well-groomed bush, to open view. I remember wondering when she'd done that.  It must have been as she prepared for the evening before I arrived home for work.
 Andrea then injected her instruction into the ritual, telling my cheerleader to climb onto the bed.  Once she was lying down, watching from her new perch, I asked her, "May I please prepare Mr. Jones for you Miss M?"  My cheerleader was rapt by this point.  Perhaps she’d doubted that it would actually happen.  Her fantasy was actually unfolding as reality.  Her sissy husband was going to participate in her being fucked by a man.  She was going to watch me suck a cock for her.  I was going to suck a cock for her.  Her one word answer said so much.  "Please," she replied.
So.  The moment of truth had arrived.  My fantasy.  My cheerleader's fantasy.  Randall's fantasy?  I don't know.  But whatever, I was about to face my new reality.  And my nearly naked cheerleader was lying on our bed watching her sissy husband about to prove to her how far he would go to please her.  She'd asked me to suck a cock for her.  But, when it had come down to it the week before, as Andrea had revealed to me, my cheerleader had been too embarrassed to see it through.  Now, with the assistance of a stranger only hours before, our fantasy was becoming reality.
Facing Randall, I asked, "May I Mr. Jones?  Prepare you to fuck my wife?"  His one word response, "Sure," was the last word I recall him uttering for a while.  I gave one last glance at Andrea, as if for final assurance that I should proceed, and she told me, "Go ahead sissy.  Just like we discussed."  In that moment I sank to my knees, my made up feminine face level with the crotch of a man who would soon be fucking my cheerleader.  I reached forward and, with trembling fingers, began unbuckling Randall’s belt.  How can I describe this moment?  I was fully aware that all eyes in the room were upon me, especially those of my cheerleader.  The other thing I feel I should mention here is that I was in a state of wonderment about what to expect.  My cheerleader had told me Randall was very big.  I had also sucked dildos, so it wasn't as though I wasn't used to having my lips around a phallus, but this was going to be different, and I was completely tuned in to that fact.  Then, Andrea had given me certain instructions on what she expected to see me do.  She wanted me to, as she'd put it, "Show your wife how reverently you can treat the cock you are going to place inside of her."  And so it was with nervous apprehension that I unbuttoned Randall's trousers and pulled them to the floor, helping him step out of them, leaving him only in his blue Oxford cloth boxer shorts, but with the shape of his already aroused cock pushing against the fabric.  Finally, with one slow tug downward, I freed the first cock I would ever suck, and watched as it bobbed forward toward my face.  Almost instinctively, it seemed, I grabbed it and held it in my hand.  I still remember noticing the heat that emanated from Randall's thick, hard cock.  Then, recalling Andrea's instructions that she had emphasized to me earlier, I looked upward into Randall's eyes for a brief moment, and then looked directly at my cheerleader.  My eyes locked upon hers, I leaned in and softly kissed Randall's cock right on the head, holding the kiss long enough to ensure that I'd left a distinct lipstick mark upon him.   
 My cheerleader was beyond mesmerized.  I think she may have thought that there was a chance that I would not carry out the act.  But, really, there was no chance that I wouldn't.  Still maintaining eye contact with my cheerleader, because this blowjob, as Andrea had emphasized to me, was for her, I opened my mouth and let Randall press his cock inside of me.   
 Others have said this, but from that moment forward I can affirm the truth of the claim - there no comparison between sucking a rubber dildo and sucking a living, breathing, cock.  I slowly savored my first taste of a man, enjoying the feel of his pulsing rod inside of my salivating mouth.  Then, somewhat reluctantly I recall, I slowly slid my mouth off of him and then dipped my head beneath him and gave him a long, slow, wet lick along the underside if his cock.  My cheerleader was correct too!  He was very big.  Long.  And thick.  Only seeing him enter my cheerleader later made me realize even more just how big he was.  I took him back into my mouth and tried to swallow as much as I could, which was probably only a few inches.  Mainly, I was intent to suck him softly, trying to help him become hard for my cheerleader.  I honestly do not remember how long I sucked Randall's cock that first time.  But I do remember that I might not have stopped were it not for Andrea eventually interrupting me, saying, "Sissy!  Time to put him inside of your wife.  This is for her pleasure.  Not yours."
 Stopping at Andrea’s command, I stood up from sucking Randall's cock, holding his erection gently in one hand.  "May I Mr. Jones?"  As if understanding what he needed to do, he crawled upon our bed.  My cheerleader, also seeming to know what was about to happen, lay back upon her pillow, letting her legs fall open to the side, allowing Randall access to position himself between my cheerleader’s thighs.  "Kiss her pussy first sissy," Andrea coached me from her chair.  I leaned down and placed a soft, loving kiss on my cheerleader's excited pussy, letting my tongue dip inside of her briefly, tasting her, before pulling away and then, in a deliberate motion, I guided Randall's hard, thick, cock inside of her.   
 Then, from mere inches away, I watched as he slowly slid his cock inside of my wet cheerleader, and I could almost feel her arousal as he spread her pussy lips wider than I ever had.  And her words as Randall penetrated her, "Oh God!  Thank you sissy!" still echo in my head when I remember the night.   

 As soon as Randall had buried his cock inside of her, my cheerleader wrapped her legs around his waist and pulled him in tighter, refusing to permit him to pull out.  She was looking right at me as she relished that first moment of being filled with such a big cock, her eyes speaking volumes about how much it meant to her that I was consenting to this.  Then, she closed her eyes, and I sensed a separation occurring, where my cheerleader became lost in the sensation of being fucked by a man, and although I was right next to them watching, it was as though I was no longer in the room as far as she was concerned.  She began encouraging Randall to fuck her.  Harder.  Deeper.  Longer.  Randall appeared up to the task as far as I could tell.  My cheerleader released her hold upon Randall, letting her legs fall open and hang suspended above her, permitting Randall the freedom to begin pumping in and out of her.  At first, he moved slowly, withdrawing nearly all of the way out of her, and then re-entering her until he was once again buried inside of her.  And with each movement in and out, my cheerleader sighed and moaned her approval of his motion, continuing to plead with him to fuck her.  I was mesmerized by what I was watching.  It wasn’t like watching porn, though it was as pornographic as any I’d ever seen, because this was my special woman – my cheerleader – the one and only woman I had ever made love to – and she was being fucked by a man. I was equally amazed at his staying power.  I believe I would have already cum inside of my cheerleader if I were fucking her.  But Randall seemed capable of going forever.  I don’t know how long he fucked my cheerleader that first time I watched them, but it seemed to last forever.  Eventually, he increased his pace, and my cheerleader seemed to realize that he was about to orgasm inside of her.  She offered him encouragement, urging him to fuck her – to fill her – to cum inside of her.  Suddenly, Randall tugged at her bra and pulled it down, revealing her full breasts.  He grabbed one in his fist and leaned down and took the other in his mouth, biting her nipple, causing a shriek from my cheerleader, but not one that indicated she wanted him to stop. 
  To the contrary, it seemed to set her off onto another level of excitement.  I already knew how much my cheerleader loved the feeling of being filled with hot cum, and I could see how excited she was to be about to receive Randall’s hot blast inside of her.  Within moments I could tell that Randall was cumming inside of my cheerleader’s pussy, and she welcomed all of it, panting and groaning as he thrusted repeatedly with each shot of ejaculate. 
  I felt a presence behind me at this moment, and turned to see Andrea standing just over my shoulder, softly touching me, as if she were there to console me as I witnessed the surreal event that was coming to a conclusion.  As my cheerleader lay beneath Randall, each of them spent from the incredible orgasms they shared with each other, Andrea whispered in my ear, “Do you see why she needs this sissy?”  I did not respond.  But I did understand.  I’d made love to my cheerleader many times, and I believe she loved it.  But Randall had just fucked her, and she loved that too.  I was happy for her.
 After a prolonged silence, Andrea announced, “It’s time.”  My cheerleader opened her eyes for the first time since she’d closed them early in the fucking, and looked right at me.  “Are you ready sissy?”  I was only confused for a blink, and I realized what the women were talking about.  I was going to clean them.  As Randall withdrew, his white cream oozed out from around his cock at the entrance of my cheerleader’s pussy.  His cock was now soft, but still large and full from the exertion he’d just gone through.  And coated with a thick layer of his sperm.  Andrea directed me, as if unwilling to risk that I might refuse, “First her lover sissy.”  All three were watching me, each with a different question in their eyes.  Andrea was waiting to see if I would comply with her instructions.  Randall was waiting to see a sissy suck his cock clean.  And my cheerleader was watching to see whether I would really commit such an act for her.  I leaned down and took his wet member into my hand and directed his swollen cock toward my mouth and took him in, tasting his sperm mixed with my cheerleader’s own orgasmic juices.  The difference between sucking a soft cock and a hard one is significant.  I sucked Randall and licked him until he was clean.   
 Then, without further instruction, I placed my mouth onto my cheerleader’s gaping pussy and sucked, creating suction that resulted in a flow of sperm entering my mouth.  My cheerleader encouraged me as I cleaned her man’s sperm out of her, telling me how much she loved me as I did so.  I sucked and licked my cheerleader until I brought her to another orgasm, oblivious to the fact that her man and Andrea were watching me from the side.  When she seemed spent, I stopped and stood by the bed once again, wondering what would happen next, now that the cuckolding was complete.
  Andrea seemed to understand the need for a transition of some kind.  She told me to go downstairs and bring everyone a drink.  So I took orders and left the three of them alone, no doubt to talk about me.  I returned with a tray full of drinks and found that Andrea had returned to her chair, and my cheerleader was lying back in our bed, her head nuzzled into Randall’s neck, who was lying next to her.  I served everyone and then, at Andrea’s direction, kneeled beside her.  We quietly sipped our cocktails, everyone seeming content with the evening.  Andrea broke the silence when she told me that she was impressed with me, telling me that she thought I was a natural cocksucker.  I was embarrassed to hear her say such a thing so conversationally in front of my cheerleader and her man, and yet, proud to receive her compliment.  I think that is part of what it is to be a sissy.  We are humiliated when someone calls us a cocksucker, but we also love being complimented on our ability to make a man feel good, and especially if it is in support of him providing satisfaction to the women we worship.
 Andrea indicated that she and Randall were going to have to leave soon.  But first, she wanted me to get him ready to fuck my cheerleader one more time.  She told me to crawl onto the bed and do it where he was lying next to my cheerleader.  So, I climbed upon the bed and positioned myself between his thighs, leaning down to take his still soft cock into my mouth, sucking him and licking him until he was erect enough to fuck my cheerleader again.  I felt him growing harder in my mouth as I sucked him and knew that it would not be much longer before he was ready for her again.   
 My cheerleader was quietly encouraging me, repeating, “Yes.  Yes.  Yes.  Suck him sissy.  Suck him.  Yes.”  She was enthralled watching me prepare her man for her.  Finally, he was ready and my cheerleader climbed onto him, straddling his body and slowly sinking down upon his cock, taking him inside of her. 
  She then began to rock back and forth, grinding against him, feeling his cock deep within her pussy.  She didn’t take long to get going at full speed, riding him harder and harder as she fucked him right in front of me.   
 Andrea interrupted the action and told me to rub myself as I watched.  She wanted me to cum with my cheerleader.  And so, I rubbed my penis through my panties and soon I could feel it coming.  It didn’t take much as I was already aroused.  Within a few moments I was cumming inside of my panties and my cheerleader was cumming on Randall, who was filling her again. 
 Once again I had to clean Randall’s cock after my cheerleader climbed off of him.  Then, Andrea announced that she and Randall were going to leave us alone.  By this point, I wasn’t sure I really wanted to be alone with my cheerleader.  Could I look her in the eye after what I’d done?  I didn’t know.  Andrea told us that she and Randall would be back the following Friday.  She took my cheerleader’s and my phone numbers with her, indicating that she planned to be in contact with each of us during the week.  And so, it appeared, she had taken us under her wing, and planned to see us through our progression into a new stage in our marriage.
Andrea and Randall saw themselves out, leaving my cheerleader and me alone in our bedroom.  I couldn’t think of anything to say, and my cheerleader didn’t seem to know what to say either.  I couldn’t look her in the eye I was feeling so embarrassed as what I’d done began to sink in more firmly.  She was smiling warmly at me though, and that felt good.  She beckoned me to cuddle next to her, and so I crawled up beside her.  She kissed me softly upon my forehead, as if to thank me.  After a few minutes she nudged me downward, letting me know that she wanted me to clean her one final time.  And so I buried my face between her thighs and went about the task that I loved more than anything, pleasing my cheerleader with my mouth, and sucking all of Randall’s sperm out of her in the process.
 I couldn't figure out at the time why I seemed so willing to comply with this relative stranger's directions to me.  But looking back on it, I believe it was because I did want to take this step with my cheerleader, escalating from wearing nightgowns and lingerie and such around her and when we made love, to her seeing me in an even different light, as a man completely absorbed in expressing my deep seated longing to be seen as a feminine creature.  The rest of the weekend was interesting.  We didn’t discuss Friday night’s event.  We didn’t need to.  We had each been there.  I’d watched my cheerleader become engrossed in being fucked by a man, revealing her complete feminine submission to a man.  And she’d watched me reveal my utter sissiness to her, and in front of a man and a stranger.  I could not have shown a greater willingness to humiliate and embarrass myself.  But my cheerleader treated me so carefully and tenderly all weekend, as if sensing that I was fragile and needed a soft touch.  I gave her oral pleasure for the next two nights, but that was all.  She seemed uninterested in me going inside of her, although I would have loved to.
 And so, that is the story of how I became a sissy cocksucker for the first time.  I have thought long and hard about sharing this event in my sissy life with the world.  It was a difficult experience, but one that I now know had to occur.  And while it is embarrassing to admit some of what I did, I made a decision a little over a year ago that I was going to share my story, and have committed myself to do so.  I hope that most who read this are able to get something from it.  But mostly, I hope people won’t judge me too harshly for my behavior.  I realize that some may call me a fag or something like that.  I don’t feel like one though.  When I sucked Randall’s cock, I felt like a woman at the moment I did so.  My sexual orientation is so embellished with femininity, that it feels natural to me to please a man with my mouth.  The next weekend with Andrea and Randall was another significant step for my cheerleader and me.  And with the next post, I will tell about the week leading up to the weekend and then the weekend.  Please be kind in any comments made about this last confession of my sissy journey. 

Kisses,

Leeanne




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