My Cheerleader And Her Quarterback

[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 - Sissy And Cheerleader's Last Weekend With Andrea - Part One - Sissy And Cheerleader's Last Weekend With Andrea - Part Two - Cheerleader Thanks Sissy - Cheerleader Does A Sleepover - How My Cheerleader Vets Men - Cheerleader Flirts - With Purpose - Cheerleader Is A Happy Girl - Cheerleader Learns – Juggling Isn’t Easy - Cheerleader Gets An Itch - My Cheerleader's Summer of Contentment. These are the previous posts that tell the story about my sissy journey.]

In this post I am going to tell about something that is, perhaps, the most difficult thing I have revealed thus far as I have told about my sissy journey.  I certainly never saw this coming when I first confessed my sissy nature to my cheerleader.  Not only was this next event I am about to describe a very traumatic thing for me to accept and live through, but it is deeply embarrassing for me to admit that I actually stood by while it occurred.  I cannot undo what happened during the Fall of 2013, and has been repeated a few times since then, nor do I necessarily want to now.  The emphasis is on the word, "now," in the last sentence.  I realized afterwards that it was important to my cheerleader.  In the final analysis, that is what matters most to me.  By this prologue, I am merely providing some small preliminary notice that what I am about to reveal was very difficult for me to live through at the time it occurred.  And, as I have done in the past, I beg for those who have been following the story about my cheerleader and me to not think too harshly, about either of us, as we each played a role in what I’m going to tell about.

I mentioned early in my postings about my sissy journey that I had a huge high school girl crush on my wife when she was a Senior cheerleader and I was a Freshman.  See, “Sissy Marries Cheerleader.”  That is why I refer to her as “my cheerleader” throughout my blog.  In that same blog posting, I talked about her first husband, with whom she had two children and had only recently divorced from when I met her.  When they dated in high school she was the head cheerleader and he was the quarterback of the football team, so it was a very fairytale romance for them that did not end well when she caught him cheating on her with a woman with whom he worked. 

When I joined my cheerleader’s life 29 years ago, I worked very hard to be a good stepfather to her two sons by her quarterback.  I coached them in Little League and any other sport that either participated in.  But I also encouraged a better relationship with their father than they had been experiencing before I arrived on the scene.  My parents were divorced when I was fairly young and I understood how difficult split marriages were, especially on the children.  Thus, I actually had managed to establish a comfortable relationship with my cheerleader’s first husband, who I am going to call Tom, although that is not his real name.

In my post about the last weekend my cheerleader and I spent with Mistress Andrea, I told about a sort of wrap-up counseling session Mistress Andrea held with my cheerleader and me.  See “Sissy and Cheerleader’s Last Weekend With Andrea – Part Two.”  It was during this session that my cheerleader talked about how much it meant to her that I had given her the opportunity to experience sex with a man, especially a man such as Randall who had an impressive cock that satisfied her in a way that I had, apparently, not managed to do.  In that post, describing how my cheerleader had confided to me, in the presence of Mistress Andrea, I wrote what she related as follows: The kicker for her though, was when I began injecting the fantasy of her being fucked by other men, even men we knew.  She said that she had begun privately fantasizing about being fucked by other men.  Men with bigger cocks.  Men who took her like a man - rather than as a sissy.  Men like, it turned out, her first husband.  She shared with us that he had taken her cherry when they were in high school.  Sex with him was always amazing she told us.  As she shared this news with me, for the first time, in front of Andrea, I was overcome with a deep sense of inadequacy.  When Andrea asked me to share how my cheerleader’s revelation made me feel, I admitted the same.  I was being confronted with my sissiness and being forced to put into words the emotions evoked by all that had gone on.  My cheerleader was clearly concerned about my reaction to her sharing her sexual relationship with her first husband.  She insisted that sex with me was wonderful and that she loved what we did together.  All that she was saying to me was that she had experienced great sex with a man who was blessed with a huge cock - had had babies with him - and always longed for that one thing that he gave to her.  On the other hand, she would not have traded me for him no matter what.  

Then, in another post, my cheerleader once again referenced her quarterback when she thanked me for giving her the freedom to experience a big cock again.  See “Cheerleader Thanks Sissy.”  It was in that posting that I wrote:  She talked about how great if felt to be filled with such a huge cock – one that filled her with sperm.  She thanked me for giving that to her.  She loved me, but she had missed being filled with a big cock for so long and that a real one was so much better than a fake one, no doubt referring to the large dildos I’d introduced to our lovemaking long ago.  And I thought I had shown her something she was not familiar with.  Instead, I’d unwittingly rekindled her memory of what being filled in that way felt like.  

Thus had I learned that, long before I entered her life, my cheerleader had already experienced a huge cock and knew the satisfaction a woman could receive from an alpha man.  In fact, it turns out, before me she had only experienced her quarterback’s cock.  So, compared to many women, she was especially blessed, having lost her cherry to a man with a big cock and having enjoyed the experience of knowing what it felt like to be well fucked from an early age in her life.  I’ve mentioned before that, for a sissy, I am not tiny.  And I do believe that I did provide satisfaction to my cheerleader, although being in the correct position, such as doggie style, always helped.  But, as I’ve also emphasized, whatever I lacked in the actual fucking department, I more than made up with using my oral skills.  But when I introduced the large dildos into our lovemaking and my cheerleader experienced a semblance of what she’d experienced when being fucked by her quarterback, I awakened ancient memories within her – pleasant ancient memories – that she began silently longing for once again.  My encouragement that she take a real man for a lover wasn’t, it turned out, too much of a hurdle for my cheerleader to clear.

Why am I going over all of this again?  Well, I am about to tell you why.  In October of 2013, my cheerleader’s quarterback’s father passed away.  His mother had been dead for many years, so this was his last surviving parent.  Anyway, obviously his sons (my stepsons) were going to attend the funeral.  I might have attended also if we still lived in our hometown, rather than Washington, D.C.  However, I had work responsibilities that prevented me from going.  My cheerleader, on the other hand, felt that she should attend the funeral, especially for her sons.  I, of course, agreed with her.  I did think it was the right thing to do.  But I will make a bit of a confession here.  With the things I’d learned recently from my cheerleader about her past with her quarterback, I felt a slight twinge of jealousy and worried about her being in his company when I was not around.

In any event, my cheerleader did travel to our hometown and attended the funeral.  Learning more about it later from her, it turned out to be a bit of a high school reunion for her graduating class.  Remember, my cheerleader was a Senior when I was a Freshman in high school.  I was not part of her circle of friends.  In fact, as I have said before, she did not even know I existed then.  Many of her (and her quarterback’s) friends attended the funeral as well.  Of course, there was a reception following the funeral and my cheerleader had an opportunity to catch up with her old friends and, I’m sure, relive those days of her life when she and her quarterback were an item and she lost her virginity to him, a memorable event that happened one night in her bedroom at her parents' beach cottage at Sandbridge Beach, Virginia.

My cheerleader ended up staying at the post-funeral reception until there was no one left except family.  As she and her sons were walking out of the club, where the reception had been held, her quarterback approached her to thank her for attending.  By this point in her quarterback's life, the woman he had left my cheerleader to marry had left him for another man.  Anyway, as he was thanking her and saying goodbye, he asked if she and the boys would like to join him for dinner.  As my cheerleader explained it to me, she was about to decline when her sons simultaneously said they thought it would be a great idea.  And so, she reluctantly agreed to go to dinner with them.  Note this – I learned all of this after the fact.  I was home in D.C. none the wiser about what was taking place.  Had I known, I would have probably become an emotional wreck thinking of my cheerleader being out to dinner with her quarterback.

He took them to a very nice restaurant where they had drinks and dinner.  Apparently, it was a quite enjoyable time for their “old family” to be together.  And, make no mistake, I get that.  Some might say that it was wrong.  But I don’t see things quite like that.  A mother and a father never stop being a mother and a father, even when their children are adults, as my cheerleader’s and her quarterback’s offspring were.  The dinner was an opportunity for the four of them to be together as a family again, if only for a few hours.  I think that is how my cheerleader began to see the dinner and so she let her guard down and enjoyed herself.  As it turns out, she may have let her guard down a little too much.  As they were leaving the restaurant, my cheerleader’s sons went to a parking garage to retrieve the car the three of them had traveled in together to the funeral.  While she and her quarterback were waiting outside of the restaurant, he began to get sentimental with her.  He told her how much he had missed her over the years and how much he’d regretted leaving her as he had.  He confessed to her that his last wife had not been nearly as good of a lover as she had been.  Then, before my cheerleader even saw it coming, he kissed her.  But what was the most difficult thing for me to accept, as my cheerleader told me what happened when she had returned home the next day, was that she kissed him back.  I know she was attempting to be honest with me when she told me about this event.  She could have never mentioned it and I would never have known.  Hearing her tell me she kissed him back, I could not resist the question that I had to ask.  “Did you enjoy it?”  Her answer, “Yes.  I did,” hit me hard in the gut.  My cheerleader, it turned out, continued to have feelings for her quarterback.  He had tried to persuade her to go with him to his apartment, but she told him she could not do that, and so they parted, sharing only what I believe was a long, lingering and passionate kiss, one filled with all of the memories of their past lovemaking.  Unable to stop myself from asking one too many questions, something I never did in a courtroom, I asked her if she would have gone with him if circumstances had been different - if it weren’t for her sons being present.  Again she was honest.  And it hurt.  She told me that, as he held her close to his body when they kissed, she could feel him pressing against her.  She admitted that she might have gone home with him if she could have, just for that one time opportunity.  She also told me she was glad she couldn’t go with him though.  She wouldn’t have wanted to do that to me.  She’d have felt badly about it.  I thanked her, but the damage to my psyche had been done - self-inflicted as it were because I asked the question drawing the response.  I knew she wanted to be with him.  I knew she had, if only for a fleeting moment, imagined their reunion.  That was all I needed for the image to be indelibly etched into my sissy imagination.

The night that my cheerleader told me about her kiss with her quarterback we made love, but not in the way a man and woman typically make love.  No.  We made love the way a woman and a sissy make love.  I went down on her and worshipped her pussy with my mouth.  As she always does now, when I pleased her in that way, she whispered and cooed about what a sweet lover I was, telling me she loved her sissy so much.  But, instead, what I heard that night was how much she missed her quarterback’s huge cock – the cock that had taken her virginity in high school and delivered her two babies – the cock that had filled her over and over with cum during their high school years and marriage.  Locked in my chastity cage, unable to achieve my own release, as I worshipped at my cheerleader’s temple, I imagined her being fucked by her quarterback and loving it.  I think she may have been thinking similar thoughts, although she was too kind to articulate them to me.  I was wise enough to not ask.

What I did

What I imagined my cheerleader was imagining.
While hearing about her encounter with her quarterback following his father's funeral was difficult for me, I also was touched that she was honest with me about what had occurred.  Still, I could not get the image of her kissing him out of my sissy head.  Closely following the image of her kissing him would always be an equally vivid image of them fucking.  Our lives continued onward though.  The following weekend, when Jason came over on Saturday, my cheerleader took him straight to our bedroom.  It was as though she needed to be fucked in the worst way.  I recall wondering whether her urgent need for Jason was related to her recent encounter with her quarterback.  I mean, I knew she would eventually fuck Jason that next weekend.  That was why he came to our house.  But she literally took him by the hand when he walked in the door and said, “Come here!  I want you!  Now!” and led him up to our bedroom, leaving me downstairs alone.  There was no hint that she wanted me in the room when they fucked.  My cheerleader and Jason stayed in our bedroom all afternoon fucking.  I could frequently hear her loud feminine cries of joy as they must have been really going at it hard.  Finally, around dinner-time, they came downstairs for something to eat.  Jason actually seemed embarrassed for me, but he needn’t have.  I knew what had happened.  He didn't.  He had just played the role of my cheerleader’s quarterback for a few hours.  She needed that release.  As for me, I accepted that it had to be.  My cheerleader was more of a sexual animal than I had ever realized in our early days of marriage.  She had learned to live without her quarterback.  Then, when he kissed her, it was like she had received a small taste of something delicious without receiving a full meal.  He left her starving for more.  She needed what Jason gave her that afternoon.

Jason and my cheerleader retreated to the den where I brought them drinks and then prepared dinner for them.  That night, we watched a movie together and then they went to bed, leaving me out entirely until the next morning, when I brought them coffee and breakfast in bed.  When Jason left for the day, my cheerleader and I laid around in bed together cuddling, not speaking about what I believe we each knew had occurred that weekend.  And although the image of her fucking her quarterback would not leave me alone, I felt like she had gotten it out of her system.

We went on with our lives much as we had been for the next few weeks.  Then, one night right just before Thanksgiving, while we were watching a television program, my cheerleader announced, without preamble, “Tom called me today.”  My heart immediately caught in my throat.  Tom was her quarterback.  “He did?” I replied.  My cheerleader became quiet, as though she was thinking about how to say what was obviously on her mind.  Meanwhile, she had reached down between my thighs and begun softly stroking my ball-sack through my panties, possibly intentionally creating a distraction.  “He’s going to be in town for business tomorrow,” she informed me.  “D.C.?” I asked.  “Uh huh,” she confirmed.  Again, she became quiet.  “And?” I coaxed her to go ahead and spit it out.  I sensed what was coming.  She remained quiet.  “Do you want him to come here?” I finally asked her when she remained uncomfortably silent.  Her response was immediate, “Of course not!  I wouldn’t dream of that!”  What she didn’t say though, was that she didn’t have something else on her mind.  “He wants me to go out to dinner with him,” she finally confessed, turning to look directly into my eyes, as if gauging my reaction.  That she even told me he called and why was enough of a hint to me as to what she wanted to do.  I could barely meet her gaze, but asked her, “Do you want to?  Meet him?”  She gave me her shy, but deadly, smile, and said, “Yes.  I do," adding, “If you don’t mind.”  She wanted my blessing.  I had never denied her anything she desired.  Could I agree to this?  “Just dinner?” I asked.  She actually blushed when I asked for that clarification.  Then, she said, “Well, that’s all he actually invited me to do.  But, I don’t know if he meant something else.”  She had me hooked by this point.  “And, if he does?  Mean something else?  Then what?  Are you saying you want to?”  Her hesitant, whispered reply, “Maybe.  I mean, I think, yes.  I do," sent a shiver up my spine.  “Are you asking me if you can bring him home with you after dinner?”  She shook her head emphatically 'no.'  “I don’t think that would be a good idea!  I don’t want him to think you know.  I mean, I’d hate for him to think that I, that we, you know, that you’re a, well, a sissy,” she finally spit it out.  So, there it was.  My cheerleader wanted to fuck her quarterback again.  That much was perfectly clear to me.  She also hoped that was what he wanted. 

'Seriously?' I thought to myself.  Could there be any doubt about his intentions?  Of course he'd fuck her!  All she had to do was give him a tiny hint that she was receptive and he’d have her in the sack quicker than a blink of an eye.  The real issue for my cheerleader was me.  She didn’t want her quarterback to know that her second husband was a sissy.  If I had been thinking rationally at the moment of her disclosure, I would have agreed with her.  I wouldn’t want Tom to know that I was a sissy.  I’d never be able to look him in the eye, and there would be many more opportunities during my life when I’d have to be in his company.  The entire time we were having this conversation my cheerleader was gently stroking me outside of my panties.  I knew what she wanted.  Could I give her this?  One time?  “If this is what you want,” I told her, “then you should meet him.”  She was unable to conceal her inner glee at receiving my consent.  She hugged me and held me closely, whispering in my ear, her breath hot as she said, “I love you so much sweetie.  Come on, let’s go to bed.”

We went to our room and got in bed.  As soon as we were in bed she pulled her necklace over her head and presented the key to my chastity cage.  She unlocked me and removed the cage.  Then, although I was dressed in a nightgown and wore a bra with breast forms, we made love that night.  The way a man and a woman make love, despite my feminine presentation.  She stroked my penis and then sucked me softly and slowly, bringing me to the edge over and over until she finally turned around onto her knees to accept me doggie style.  We fucked that night and, as I fucked my cheerleader, I pictured her with her quarterback.  I knew why she was giving me this gift.  It was an advance thank you for my blessing her date with her quarterback the next night.  I did not kid myself for a second – I knew they would consume more together than dinner.

When we woke up the next morning, as I dressed for work, my cheerleader relayed a plan she had obviously spent some time conjuring in her mind.  She wanted to explain to her quarterback that I was away on business, but that she could not bring him to our house.  She could tell him she just did not think it would be right.  She figured she could simply go back to his hotel with him and then come home when they finished.  That way, she could be with him and make him think she was cheating on me, even though she wouldn't be, really, because I actually knew what she'd be doing.  I agreed that her plan made sense.  I asked how I would know whether she would be going with him to his hotel, since he’d only asked her to dinner.  That’s when she gave me her smile that revealed what I already knew from our conversation the night before.  There was no doubt in her mind that she would be going back to her quarterback’s hotel room.  She had that glint in her eye that I had not seen in some time.  Despite her ability to openly fuck other men, this was going to be a special night for her.  I could only imagine what she would wear for their dinner date.  I asked her if she planned to spend the night.  She told me that she wasn’t going to count on it, but that she would be prepared, just in case.  She intended to pack an overnight bag.  Her quarterback, when he saw that she had packed an overnight bag, would understand that she had planned to fuck him all along. 

Needless to say, I did not concentrate on work much that day.  As I was leaving the city to drive home in the evening, my cheerleader called me.  She was heading into the city as I was heading out.  We were literally going to pass each other heading in opposite directions.  Her, to a rendezvous that I knew she was extremely excited about.  Me, home alone to wait for an evening of self-torment to end.  She had called to tell me that she had prepared a salad for me to eat for dinner and to thank me for being so understanding.  I wasn’t actually feeling very understanding at the moment.  In fact, I was torn up inside and beginning to regret giving her my blessing.  But it was done at that point, so I told her to have a nice evening, as if what she was intending would somehow end up qualifying as a “nice evening.”  So, as my cheerleader travelled to meet her quarterback for dinner, I drove home to an empty house, knowing that whatever happened between the two of them for the rest of the night was out of my hands.  When I arrived home I went upstairs to shower and change.  Upon walking into the bedroom I saw that my cheerleader had left new lingerie lying on our bed next to a note she’d written to me. 

The note read:

Dear C,

            I imagine that, as you read this note, you might be feeling regret about agreeing to allow me to have this evening with Tom.  I understand if you are.  I only want to say this to you baby.  I love you.  I love you more than you can ever possibly imagine.  While we have had some difficult times, the one thing I have never questioned is your love for me.  I hope you never question my love for you.  No man could ever replace you in my life.  This need that I have, to be with Tom again, is not something that I can explain.  But somehow, I think you may understand it better than I do, or else I do not think you would have agreed to let me meet him.  But no matter what happens, please know that I would never do anything to hurt you or ruin what we have together.  We agreed to life.  And that is a promise I intend to keep.  If you want, I’ll tell you all about tonight.  We don’t need to have any secrets.  Not anymore. 

                                                                        I love you,

                                                                        Me

What could I say to that?  How could I harbor ill will toward my cheerleader after a note like that?  As she was going to meet her quarterback, she had assured me that we were together for life – that she loved me more than she could any man.  I laid the note on our bed and undressed to take a shower.  I then put on the lingerie she’d purchased for me to wear on the night of her special occasion.  I suspected that she’d bought new lingerie for herself - or rather, for Tom - as well.  And if I knew my cheerleader at all, she had bought us matching lingerie, so she could picture me wearing the same thing she was wearing when she went to bed with her quarterback.

I went downstairs alone to have dinner.  I opened a bottle of wine and ate alone at our bar, maintaining a watchful eye on my iPhone, hopefully, for a message from my cheerleader.  I wished I would receive some news of her plans - something to confirm for me that I was on her mind too - but none came.  After dinner, I went into the den alone and tried to watch television, but I could not concentrate.  When it reached eleven o’clock and I had still not heard from her, I figured she must already be with him in his hotel room.  I went upstairs to our bedroom and got into our bed, alone.  I turned on the late news just to have noise around me.  I could not pay attention to anything.  This was so different than when she had entertained men at our home.  At least then I knew where she was.  I sometimes participated.  This was torture.  I wanted to know what they were doing.  Oh, I knew what they were doing.  I knew.  But I wanted to know exactly what they were doing.  I tried to imagine my cheerleader and how she must be feeling as she found herself back in the strong quarterback arms of the man who took her virginity and gave her two children.  Those two facts, alone, were so significant to me.  Randall, Jason, and Dave were only men who fucked her.  Tom was a man she began creating a life with.  He was a man with whom she created life itself.  He was a man who had meant something significant to her.  And this night, possibly at that precise moment, he was meaning something important to her again.

At just after midnight, I received a text message from my cheerleader.  “Hi sweetie.  It looks like I’m staying the night.  I love you.  And thanks!”  She left a smiley face next to her text message.  I wrote back, “I love you too.  Goodnight,” although I doubted she would sleep much.  I know that I did not.  I did finally fell asleep, after lying awake for hours thinking of my cheerleader and what she was doing with her quarterback.  I don’t know why, but I pictured her quarterback as trying to make up for the lost years, fucking her over and over, as many times as he could.  When I finally woke up the next morning, after not getting much sleep the night before, I decided I could not go to work.  I was an emotional wreck.  I wanted to be home when my cheerleader returned that morning.  I know it was crazy, but I wanted to hear about her night.  I wanted to know the details.  I wanted her to see me immediately upon returning home from her night with her quarterback.

I prepared coffee, thinking she’d be home early and we could have breakfast together.  But, the morning stretched to 10 a.m. and she had neither shown nor called.  I texted her to let her know I had stayed home for her.  Within a few minutes I received a reply.  “I won’t be home for several more hours baby.  I assumed you would go to work.”  Fuck!  She was still with him!  I was now officially a complete mess!  I decided I had to do something.  I couldn’t just sit around waiting for her to return home.  I put on my bike clothes and went for a ride.  I rode and rode and rode.  I only thought of one thing - my cheerleader fucking her quarterback.  But I rode, and rode hard, for over two hours.  I tried to burn off my anxiety.  And it helped.  A little.  Not really.  The only thing that was going to help me now was seeing my cheerleader again – holding her in my arms, even if she’d been in her quarterback’s arms the entire night before and most of the day.

When I finished my ride I showered and then changed into something that I hoped my cheerleader would like – something pretty and sexy.  I know.  I had been torn up with anxiety about what my cheerleader had been doing the past night and day with her quarterback and what was my thought?  Greeting her dressed as her sissy husband.  Well, it turned out to be the right thing to do.  She wasn’t looking for me to, suddenly, attempt to me a man for her.  She had men.  And now, she’d had her quarterback again.  I was better off presenting myself to her in a manner that was more fitting to my role in her life.

After dressing in a pretty pink ruffled panty and bra set, stay-up lace-topped black stockings and a sheer white baby-doll, I went downstairs to prepare dinner for us.  It wasn’t long before she called.  She was on her way home!  She sounded very upbeat when she spoke to me.  I told her I couldn’t wait to see her and hear about her date.  She told me she would tell me everything, if I wanted her to she added.  I did.  And I didn’t.  But I couldn’t resist.  I wanted to know.  I had to know!

When she walked in and saw me dressed as I was she smiled and dropped her bag on the floor.  “Baby!” she exclaimed.  “Look at you!  So adorable!”  She came to me and wrapped her arms around my neck.  She was wearing blue jeans and a tank top.  I wasn’t treated to seeing the outfit she'd worn for Tom the night before.  I made a mental note, though, of scoping it out later.  Smelling dinner, she asked, “Can dinner wait?  I’m really tired.  I was hoping to take a nap.”  I said, "Sure," if that was what she wanted to do.  She asked me to come upstairs with her.  As soon as she reached our room she pulled off her tank top, revealing a new black lace bra, similar to the full-cup bra she'd bought for me, and then shrugged out of her jeans, revealing a pair of matching black lace thong panties that I did not recognize.  She had bought new lingerie for her date with her quarterback.  I also noticed that her panties looked damp.  I wasn’t mistaken.  She climbed onto our bed and beckoned me to join her.  I crawled up beside her and she immediately cuddled up to me, nuzzling her nose into my neck.  She cooed, “I love you so much baby.  I am such a lucky girl.”  I smiled as she snuggled to me, happy to know she still loved me.  I wanted to know the details about her date, but did not know how to bring it up.  I finally asked, “So, was it wonderful?”  She giggled.  “Yes sweetie.  It was wonderful.  And beyond!  Can I tell you all about it later?  After I take a nap?  I'm really, really tired.”  I told her that would be fine and let her cuddle, happy to have her nude body wrapped in my sissy arms again.  As we lay there quietly, adjusting to her returning to me, my cheerleader said, “Baby?”  “Yes?” I replied.  “I don’t know if you want to.  You don’t have to.  But, I did bring you something.  If you want to, you know.”  Fuck!  She didn’t?!  But yes, she had.  She wanted me to go down on her after she'd been fucked by her quarterback.  “Ho, how long ago?” I asked.  She looked at me and smiled.  “Not long.  Just before I left him.  I wanted it to be fresh, in case you were looking forward to it.  Do you?  Want to?”  The question wasn’t asked in terms of what I wanted.  I could tell.  She wanted me to.  “Okay,” I told her.  My cheerleader’s smile told me how much she wanted me to do it for her.

Pulling the covers away from my cheerleader, I turned around to position my head between her thighs.  I was spinning somersaults inside as I committed to cleaning my cheerleader's pussy.  Based on how much I've revealed about what I have done for my cheerleader, some might question this next statement, but what I was about to do was something completely beyond the pale for me.  I’d long ago accepted that this was what I did for her.  I even liked doing it, odd as that may sound to some.  But there was something about it this time.  I was about to taste her first husband’s sperm.   The first cum that had ever entered her beautiful body.  Ever.  Sperm she’d been impregnated with two times.  I can’t even explain how I was feeling, other than extremely nervous.  I gingerly kissed between her thighs, planting soft butterfly kisses as she began to respond to my lips.  I gently nuzzled her panties, smelling them, licking them to get a preview taste through the damp lace fabric.  As I did that, my cheerleader lifted her pussy toward my mouth, encouraging me to continue. 

I was taking my time for more reasons than the effect of the foreplay upon my cheerleader.  I was summoning up the courage to tackle the task.  Eventually, she couldn’t stand it.  “Take off my panties sweetie!” she urged me in a commanding tone.  Obediently, I slipped my fingers inside of her waistband and began to reveal her recently fucked pussy.  As the fabric peeled away from her neatly groomed bush, I saw the thick strands of Tom’s cum sticking to my cheerleader’s panties and coating her bush.  Experience told me there was a lot of cum inside of her.  The thought crossed my mind, 'How many times had he fucked her before my mouth tasted the pussy he now owned much more so than I ever had?'  I licked across her bush, coating my tongue for the first time with her quarterback’s cum.  It had a distinct flavor, although it was also laced with my cheerleader’s own unique nectar.  I licked until her bush was clean and then let my tongue dive inside of her hungry, wet pussy for the first time since she'd fucked her ex.  Just inside of her opening my tongue found a huge load of thick, creamy, white sperm.  It was pungent.  I was swallowing her ex-husband’s seed.  I was really doing it.  By this point though, I had moved past the trepidation I’d felt in the beginning.  I was simply a sissy – a sissy conditioned to cleaning his wife’s pussy after she had been fucked by a man – simply doing what was expected of me.  My cheerleader was responding to my tongue as well.  She was bucking up toward my face, encouraging me to lick deeper with her actions and her vocal exhortations.  I was responding to her as I always did.  There was so much of her quarterback’s cream inside of her.  I serviced her for a good thirty minutes before I could tell there was only a scant trace, if any, of his cum remaining inside of her.  By then I had brought her to several orgasms with my tongue.

After I finished my cheerleader pulled me to her and kissed me hard, her tongue invading my mouth, tasting Tom's cum as well.  She seemed almost ravenous to taste him in my mouth.  When we broke she said, “Doesn’t he taste amazing!”  It was obvious that she had missed his cum all of these years.  

I did not know how to answer her question though.  Instead, I asked, “Did you suck him?”  Her response told me so much that I wasn’t sure I needed to hear the details later.  “Did I?  Oh baby!  How could I not?  God!  I had to taste him again!”  I was, literally, dumbfounded at her response.  I could not speak.  As if sensing my reaction to hearing her reply, she pulled me to her.  “Hold me baby.  Hold me.  I need to rest.  I’ll tell all later.  For now, just know I love you.  Thank you for allowing me to do that.”  I said nothing, content to remain quiet, not knowing what to say anyway.  As for me, my own penis was throbbing within its confinement.  I wondered whether she might reward me later.

In my arms, my cheerleader fell asleep within minutes, and I was soon gone too.  I had not slept well the night before for worry.  And she had apparently not slept much either, but for different reasons.  When we finally woke up, it was nearly 9 p.m.  By then we were both famished.  She wanted to take a shower and, so, she did that while I went downstairs to organize the dinner I’d put on hold earlier.  I was waiting for her with a glass of white wine when she came down wearing only a baby-doll.  We wordlessly toasted each other and sat down to eat, both of us remaining quiet through dinner.  I still wanted to know about her date, but felt I should permit her to get there on her own.  It had obviously been intense for her.  It had been over 30 years since they’d been together, and he had clearly been a special man to her - much more so than I had ever realized.

After dinner we went into our den and drank more wine.  For different reasons, the last 24 hours of our lives had been traumatic.  I could sense that my cheerleader was a little uncomfortable about telling me all that had occurred, even though she had promised she would.  I understood that doing whatever she'd done with her quarterback without me around was one thing.  Telling me about it was probably not so easy for her to do.  Against my better judgment in regard to the impact upon my sissy psyche of what she might tell me, I was dying to hear the details about her night with her quarterback.  I decided to let her off the hook though, and reached over and touched her cheek, “It’s okay baby.  We don’t have to talk about it.”  As if hearing me give her a reprieve provided her the relief she needed, she smiled at me and said, “No.  I’m okay.  I’m just worried about you sweetie.  I promised I’d tell all.  And I will.  I just don’t know where to start.  The night was so full of, well, everything.”  I assured her that I was okay with not hearing about it right away, but it seemed she was committed to spilling her story. 

Hearing my cheerleader relate the details of her date with her quarterback was difficult.  And yet, I was mesmerized as she told me of what transpired between them.  I want to pause in the telling of the story to try to explain something.  I was, when this event was happening in my life, truly torn up inside.  I honestly worried, despite the note my cheerleader had written to me the night of her date with Tom, that their reunion would stoke the old fire she'd had for her quarterback and she would decide that she didn't need me, or other men, anymore, and that she would return to him now that he was free from his second wife.  I also was experiencing that other feeling I always felt when my cheerleader was with a man - when she was being satisfied sexually - the feeling that I was excited and happy for her to be experiencing intense feminine joy from real sex with a man.  In other words, I was tormented by the conflicting emotions that churned within me in equal measure.  Notwithstanding all of that, I could not resist hearing her tell me about her night with her quarterback.  I also want to explain how I have decided to tell this part of my story.  Rather than write about what she told me, in a narrative form that would require a great deal of sentences composed of such phrases as, "She then told me he said...," or "She explained that he did...," I am going to tell what she told me as though she were talking to me.  In other words, I am going to use a literary device where I speak in my cheerleader's voice.  The words I use will be mine, although many will be hers as they have stuck in my sissy brain, but the narrative will sound as though my cheerleader is telling me about her date with Tom.  I hope that makes sense.  I believe it will be easier to tell the story using this approach.   When my narrative is in the voice of my cheerleader, the words will be italicized.  And so, without further ado, herewith follows what my cheerleader told me that night.

I met him at the Hotel Monaco, near the Verizon Center.  I parked my car in the hotel garage and we took a cab to a really great new French restaurant in D.C. called Le' Diplomate.  The food was amazing!  And the wine was excellent as well.  Tom ordered a second bottle before I even knew what was hitting me, but needless to say, I was feeling a lot looser by then.  Dinner was nice too.  I want us to go there together soon.  We talked about old times, and that was fun.  Not since our divorce had we really had a chance like this, to talk about our children and all.  I guess, if I am honest about it, I never forgave him for cheating on me, even though I knew I was better off, in many ways.  He told me how much he appreciated how great you were with the boys.  We also talked about Anne (Tom's then ex-wife - the woman he cheated on my cheerleader with).  I could tell he was really embarrassed to have to admit that she had cheated on him.  I gave him a bit of grief about that.  I told him, "What goes around, comes around."  It was fun to watch him squirm a bit too.

I asked her if she could tell during dinner that Tom had hopes of seducing her that evening.  She laughed and said, "Well, if he didn't have designs upon me before I showed up for our date, I know he must have begun developing some after he saw how I dressed for him."  I went shopping yesterday to pick up something to wear.  I know you saw the lingerie that I bought for you, and the matching set I bought for myself also.  But I found a really hot black dress that fit very tightly and had a low cut front, so my boobies were on full display.  If I say so myself, I looked pretty irresistible, which was my plan.  I could tell that he appreciated what he saw the moment I met him in the hotel lobby after I'd parked the car.  He told me I looked great.  But it was the look in his eyes as he watched me approach him and then kiss him on the cheek that let me know he liked what he saw.  So, anyway, we spent a few hours in the restaurant talking and drinking.  I was beginning to get a little bit anxious as I knew that we were inching toward the moment I was waiting for, and I assumed he was too.  Ya know, how was he going to broach the subject of me going back to his room with him?  Finally, he asked for the check, and then he asked me if I had to go straight home to you.  I could sense how nervous he was when he asked about you.  I couldn't resist teasing him some, and so I asked him why he wanted to know.  As he was stuttering to answer me, I said, "He's out of town.  So yes.  I can come back to your hotel with you."  His expression was priceless!  It was obvious that he wanted me to come back with him, but I don't think he seriously believed there was a chance in hell that I would.  Before he said anything I gave him one of my looks and said, "Quit wasting time.  Pay the check and let's get out of here."

We hailed a cab outside the restaurant and headed back to his hotel.  We were both very quiet.  I was so excited that I was actually going to be with him again.  As for him, I couldn't read him then, completely, but he seemed more nervous than I remember him being about anything.  I asked him to tell the cab driver to drop us off in the garage so I could retrieve something from my car.  When he saw me pull out the overnight bag, he looked at me kind of quizzically and asked, "Were you planning to spend the night?"  I smiled and winked, and told him, "I already told you my husband is out of town."  The look in his eye as everything began to add up - my dress, the overnight bag, and you out of town - we were going to fuck.

As I was listening to my cheerleader describe her seduction of her quarterback, I thought about how Tom may have thought, before the date, that he was going to lure her to his hotel room.  Little did he realize that she was the one who was about to have her way with him.  I know that it was Tom who she wanted, but I believe all of my cheerleader’s experiences with Randall, Jason, and Dave had something to do with how she ended up controlling things.  Since she cuckolded me, my cheerleader had discovered the power she held over the men in her life, and she intended to enjoy her quarterback, given the opportunity presented to her, and in the process make him regret ever cheating on her.

As we walked through the hotel lobby, and then onto the elevator to Tom's room, there was a tension.  Both of us wanted this.  I could feel it.  I still knew him.  And he still knew me.  We both remembered how things were between us.  This wasn't like with Randall, when I was doing something I'd never done.  There was also a real feeling that we were about to cheat, but without guilt or questions.  I know I would have felt guilt if you hadn't given your blessing, but he didn't care that he was about to cheat on you.  Still, I felt the sensation that we were about to cheat.  Another couple got on the elevator with us.  They were young and I could tell they were married.  They spoke and we spoke back.  They probably assumed we were married too, and that actually felt kind of exciting.  I was feeling so amped up and anxious and just, really, ready.  In a matter of minutes we were going to be alone for the first time in thirty years.

When we walked into Tom's room, he slammed the door behind him, dropped my bag on a chair, and offered me a drink from his mini-bar.  I don't know exactly what possessed me, because I didn't have a plan or anything, but when he asked me that, I took it as a delay tactic because he was still nervous about making a move on me.  I figured, we have history.  We did not need to beat around the bush.  I went after him.  I began removing his tie and then unbuttoned his shirt.  He looked at me, for the first time in the evening, like, 'Who are you?'  He was totally unprepared for me being so aggressive.  I got a kick out of that.  He was, literally, speechless and stood there as I undressed him.  After I pulled off his shoes and began unbuckling his belt so I could get his pants off, he laughed and said, "So, no drink?"  I laughed back and shoved him toward the bed, and began undressing for him.  As I did, I let my eyes shift back and forth from his eyes watching me to his cock hanging between his thighs.

I got down to my garter belt, stockings and heels.  He was looking at me like he could not believe his luck.  I have to admit that I was enjoying his reaction after all of the years that had passed.  He said, "Fuck!  M!  You still look as hot as ever!"  I smiled at him and then looked at his cock, locking on it for a long enough time that it was obvious how much I wanted it.  I had been thinking of him - of it - all day.  I wanted him in my mouth.  So much!  One of Tom’s weaknesses is having his cock sucked.  When she told me this part of her story, she smiled at me and said, “I wish you could have sucked it Sissy.  You’d love Tom’s cock.”  I blushed when she said that.  But the more important thing for me to confess here is that my penis twitched and I briefly pictured myself on my knees in front of him preparing to suck his cock.

I had an ulterior motive for sucking Tom’s cock though.  Tom always lasted longer the second time around.  I knew he’d love it if I sucked his cock, but I knew I’d love what he’d do to me after that.  I also wanted to taste his cum again.  Tom was always such a huge cummer.  I really wanted to feel it and taste it again.  I sucked him a long time too.  Every time I’d sense he was about to cum, I’d stop and slowly lick his cock or balls.  I kept him right at the edge and he was telling me how much he loved it while urging me to finish him.  I could tell, though, he didn’t want it to end.  I teased him when he began begging me to let him cum.  “Did Anne ever suck your cock this good?”  I loved his answer!  He told me, “No one sucks cock as good as you!”  I smiled as I thought to myself, ‘I bet I know someone who does.’  But that’s our secret baby.  I finally took him over the top and he began gushing into my mouth.  I knew it would be a blast, but I couldn’t take it all.  It began spilling from my mouth, dripping down my chin.  The look on his face was worth it too.  He was like, ‘Why did I give this up?’  I loved it!

After I finished him off I made him go down on me for a while.  I knew that would be the only time he would do that, because there was no way he’d do it after he fucked me. (She didn’t have to spell out what she meant by that statement.  Her first husband was not a sissy and he wasn’t going to put his mouth somewhere that it might taste a man’s cum.)  I was already so wet and ready for him by then, but he made me even wetter.  I wouldn’t say he is as good as you are in that department, but he isn’t bad either.  But I wanted to be as wet as possible so I could take him easily.  He is soo big and it had been a while since I took him.  I wanted it, but I was also a little leery of taking him inside me again.  After he ate me for a while I went back down on him to help him get hard again, which wasn’t too difficult.  I could tell how much he wanted me.  Once he was hard again I climbed on top of him and positioned his cock just right, and rubbed it back and forth on my slit for a few minutes, just to get him really slick.  I slowly settled on him, enjoying the feel of his fat cock opening me up again.  He was watching me the entire time, like he needed to see how much I wanted him again – just like he wanted me.  And I did want him baby.  Sooo much!  I slid slowly onto him until I finally was sitting on his stomach.  Then I laughed out loud, remembering how fucking good his cock felt when it touched me in places I couldn’t remember being touched since he left me.  After a minute or so, I began riding him, cowgirl style, sliding up and down on his cock.  He felt sooo good.  He was sooo big and sooo hard.  I knew he would last too.  He always did on the second time.  I remember I kind of zoned out on him as I just kind of savored his cock.  Every thick inch of him.  I never imagined I’d ever have him inside of me again.  And there I was, fucking him again.  He told me to finger myself while he fucked me and, when I did, that was the end of it for me.  I began fucking him harder and harder until he finally came inside of me.  And did he ever cum!  My God!  He filled me with so much hot cum!  It was incredible and all I could think of as he finished was how much I wished you were there to taste him.  I really did think that.

She went on to tell me that they fucked two more times before they finally fell asleep around 3 in the morning.  When they woke up late the next morning, she sucked his cock again and they fucked again.  Then, after calling room service for some food, they fucked a few more times into the afternoon until she finally knew she had to leave.  And she left all of his afternoon cum inside of her for me.  That’s why there had been so much when I went down on her after she returned home.  I was stunned to hear her description of her night with her quarterback.  My cheerleader was obviously feeling very good about herself and what had happened.  She also emphasized how thankful she was to me for permitting her that opportunity.  I had to ask her if she had gotten him out of her system.

 I don’t know baby, to be honest.  I thought I might be satisfied, if I could only feel him one more time.  But now, that I’ve had him again, felt his big cock again, I don’t know if I want it to be the last time.  He told me he could arrange more business trips to D.C.  I can tell he wants us to meet again.  He asked me how often you travelled.  I told him some, but that it wasn’t necessarily a regular thing.  He told me all I needed to do was let him know and he could arrange a trip.  I think he would too. 

The one aspect of the whole thing I didn’t like was that my cheerleader’s quarterback was so willing to cheat with her as to me.  I had always been good to his sons, and it bothered me that he so willingly fucked my cheerleader with no concern to me.  I told her too.  But my cheerleader laughed that off, explaining that we were the ones who knew what we were doing to him.  She asked me if I would really want him to know that I knew what she and he were doing.  Of course, I knew the answer to that question was a negative.  We ended up leaving it as something we’d talk about more.  I ended up being glad that I agreed to let my cheerleader meet her quarterback.  I think it really did her a lot of good to be able to tease him some for his fuck up, and also to show him what he had been missing since he left her.

That night when we went to bed, as I had hoped, my cheerleader released me from my chastity cage.  As she unlocked it she said, “I want to thank you baby, but I don’t want you to go inside of me.  I’m really very sore there.  Just let me take care of you tonight.  Okay?”  I was thankful for anything I could get, and as it turned out, I think I ended up getting the best possible option.  She gave me one of the best blowjobs I have ever received from her.  Apparently she was still inspired from sucking her quarterback’s cock the night before.  She sucked me for the longest time, varying using her mouth with her tongue, going under me and licking my smoothly shaved ballsack repeatedly.  Every time I thought I was going to explode, she would ease back and extend her pleasuring.  I was moaning my appreciation, and was getting loader and more vocal.  My cheerleader was obviously enjoying how she was tormenting me.  She asked, “Sissy likes?”  I cried out, “Sissy loves!”  “Does Sissy want to cum on my titties?” she asked me.  “Yes!  Yes!” I pleaded.  I would cum anywhere at that point.  I had been leaking small amounts of sperm as she had been working me to the edge repeatedly, only to pull back right before I erupted.  Then, my cheerleader positioned my penis between her breasts and began sliding me back and forth as she wrapped them around my wet, hard penis, incrementally picking up the pace as she titty fucked me until I began spewing cum all over her breasts.  She rubbed my sperm all over them and when I was spent, she crawled over me and dangled one of her cum soaked breasts into my mouth for me to suck clean.  When I finished that one she gave me the other one to clean as well.  I didn’t mind.  My cheerleader loved watching me swallow sperm and I loved the taste.  So it was a win-win for us.  We fell asleep in each other’s arms and slept until late the next day.

I realize that was a pretty intense event to relate in my sissy life with my cheerleader.  I hope most readers can appreciate that it was important for my cheerleader to be allowed to do what she did.  I know it was agonizing for me when it was happening.  However, by the time my cheerleader finished telling me about her night with her quarterback, I realized that it was a good thing that she got to do it.  I will let readers know now that this was not the last time my cheerleader and her quarterback got together.  Since then I have “taken a few business trips,” permitting Tom to “arrange his work schedule” to bring him to D.C.  I should have known that, once it happened the first time, it really wasn’t that difficult letting it take place again.  On subsequent visits, my cheerleader and I had some understandings and on one trip, that I’ll tell about later, we actually did something very unusual that allowed me to participate to an extent.

For now, though, I’m interested in hearing the reactions I expect to receive about what I agreed for my cheerleader to do.  I expect some will think poorly of her.  I hope not.  She loves me.  She has needs though, and I understand that.  And if it was possible, I think she loved me even more after that night.  Some might think poorly of me as well.  Like, do I have any self-respect?  I think I do.  I can't explain my actions any better than to say that I love my cheerleader and would do anything for her happiness.  It is really that simple for me.  Now.