Monday, March 10, 2014

Cheerleader Gets An Itch

[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. These are the previous posts that tell the story about my sissy journey.]
During the month following the departure of Randall from our lives, Jason became a regular visitor to our home.  He spent every Saturday afternoon and night, just as he had been.  When he was with us I played the dutiful role of sissy servant to my cheerleader and him.  Occasionally the two of them would go out to dinner, leaving me alone.  Jason was apparently inspired by his Thursday night visit prior to Randall’s last weekend with us.  Living in our neighborhood, he began stopping by on random evenings on the way home from work.  He worked long hours for his Senator and would call on the way home, asking if he could stop by.  My cheerleader always welcomed him, and even seemed to like the idea of having the impromptu quickies with her only man, at least for the moment.  At first, I didn’t say anything about it.  One evening, however, I mentioned to my cheerleader that Jason was becoming quite regular in taking advantage of her availability.  Her response was not what I was hoping for, and it set us upon a slightly new course as far as she and other men were concerned.  I remember her taking a bit longer to say anything than seemed necessary.  After she spoke, though, I understood where she stood.  “I thought you wanted to be my sissy.  Not my man.  Do you think we can go back to how things were?  Before you told me you were a sissy?”  What could I say in reply?  How could there be a real discussion at this point?  I answered, rather meekly I recall, “No.  You’re right.  It’s okay.”  I still remember her reaction to my submission.  She smiled at me, touching me on my cheek as she did, and said, “That’s my good girl,” and nudged me downward to pleasure her, almost as an extra demonstration of her control over me.
It was about a week later when I came home from work and found Jason’s car parked in front of our house.  I had not known he was going to be there.  I entered a silent house and walked in through the downstairs rooms.  No one was around.  I quickly suspected what turned out to be the case.  I walked quietly up the stairs and, as I neared the top, I could hear my cheerleader moaning.  Jason was fucking her.  This was the first time she had fucked a man when I wasn’t home.  It wasn’t the first time she’d fucked a man when I was not around.  She’d been on the trip to Ft. Lauderdale with Randall (Read “Sissy and CheerleaderSpend A Weekend Apart”).  But this felt different to me – her being in our house with a man and me not being there.  I stopped where I was standing, just below the top of the stairs, and listened to them.  My cheerleader was letting Jason know how much she loved being fucked by him.  I probably should have, for my own sanity, gone back downstairs to wait for them to finish, but I couldn’t help myself.  It did hurt me to hear my cheerleader being pleasured by another man.  I couldn’t deny that.  On the other hand, there was something about hearing her receiving such intense sexual satisfaction that I could not resist eavesdropping.  And Jason certainly had staying power.  I tried to imagine what position he had her in.  Was she lying on her back with her legs spread wide as Jason plowed into her?  Or was she in her favorite position – doggy style?  She liked it that way with me as it helped make sure I touched her where she could best achieve an orgasm.  Eventually, I could hear each of them cumming together as Jason must have been filling her with his sperm.  As soon as I heard them orgasm, I quickly decided to sneak back downstairs.  I thought of leaving the house, waiting for Jason to leave, and then acting as though I had not arrived home while he was there.  But I decided I needed to accept this new thing.  My cheerleader had made clear to me the week before that I was expected to be her dutiful sissy.  It seemed to me that now was as good a time as any to let her know I understood her expectations, and that I accepted them.
I went to our wet bar and prepared a drink I knew Jason enjoyed, poured my cheerleader a glass of wine, and went back upstairs to deliver them.  Our bedroom door was slightly ajar, so standing back a bit I lightly knocked before entering.  My cheerleader replied, “Is that you sweetie?  Come in.”  She wasn’t attempting to hide anything from me.  I didn’t even think about the fact that this would be one of the few times Jason would see me dressed as a man, even if I was wearing lingerie under my suit.  My cheerleader was cuddled up next to him in her typical post-coital position.  Seeing me with drinks, obviously for them, my cheerleader smiled brightly and said, “Sissy!  That is so sweet of you.”  Jason also thanked me graciously for bringing him a post-‘I fucked your wife,’ drink.  Taking their glasses from the tray I carried, they toasted each other and thanked me again.  My cheerleader then said, “Baby, why don’t you give us a few minutes?  Jason can’t stay.  Maybe we can go out for something?”  I said, “Sure,” and left them alone to enjoy their drinks.  I returned downstairs and poured myself a glass of wine and then waited in our den for Jason to leave.  While there, I reflected on the situation.  My cheerleader had definitely set a marker for me.  She was going to have other men.  And she might do it when I least expected it.  My role was to accept her decisions.  Jason came downstairs, eventually, and said goodbye to me before leaving, thanking me again, I assumed for my continued acquiescence in him fucking my cheerleader.  In what had become an oddly natural thing for me, I said, “You’re welcome.”  He told me my cheerleader wanted me to come back upstairs.  So, after seeing Jason to the door, I went upstairs to our bedroom. 
Entering our room, I found her in bed, still naked following sex with Jason.  She was watching to see how I was going to react to arriving home from work to find her being fucked.  For my part, I was careful to show no sign of disapproval to her.  Smiling, she crooked her finger to me, inviting me closer to her.  “That was a nice little afternoon delight,” she teased.  “Sorry you couldn’t be here to get him hard for me.”  I swallowed and said, “Me too,” although I didn’t really know what response from me was appropriate under the circumstances.  As I reached the side of our bed she pulled me to her and kissed me softly on my mouth, and then breaking our kiss, she directed my mouth toward her pussy.  When I pulled the covers back I saw that Jason’s cum was already dripping from her.  Leaning over her I licked a thick load of his sperm from her slit, coaxing a sigh from her as I did so.  Her legs dropped open to the side and she urged me to continue cleaning her out.  I licked and sucked her until she had a few orgasms and then she stopped me.  Afterward, she got out of bed to shower.  After she dressed, we went to dinner.  Oddly, it was like any other meal, other than that we each new something different had taken place.  She’d had a man over to our house for sex while I was not home.  And I’d blessed it.  I understood my place as the sissy in my cheerleader’s life. 
I want to emphasize to readers that I understand some might think my cheerleader was being harsh with me.  That she might be taking advantage of my good nature.  I suppose that is a legitimate observation.  But that isn’t how I saw it - at least not after reflection.  My cheerleader did not knowingly marry a sissy.  When we married, I was a man to her.  We had wonderful, passionate sex as a man and woman are expected to share.  I revealed my sissy nature to her much later in our marriage.  Many women would have divorced me, and maybe even exposed me.  My cheerleader was hurt at first.  But she loved me and she tried to accept me.  She even learned to enjoy my nature to a certain extent.  Then, I led her to the decision to experiment with other men.  None of what happened leading up to me being cucked, and even up to the present, was something my cheerleader conjured up in her mind and manipulated me into accepting.  I was responsible for the state of our relationship much more than I felt she was.  I’m also not saying she hadn’t taken control of things either.  But please don’t judge my cheerleader harshly.  I asked for this.  She was simply making sure I didn’t try to turn things back to the way they were, now that we’d reached this point.
Memorial Day weekend was approaching in a few weeks from this time.  Our next-door neighbor was throwing a big party and we were invited.  On the Saturday afternoon of the party, my cheerleader went to her spa and got the treatment.  When she came home her toenails and fingernails were bright red.  She also had a shopping bag from a high-end lingerie store in Washington, D.C.  She told me to follow her upstairs to our bedroom.  In the bathroom she began to undress, asking me to draw her a bath.  I poured a capful of foaming bath oil into the tub and helped her step into the tub.  I helped her wash and, while doing so, I asked what she’d bought.  She had purchased us matching lingerie to wear to the party tonight.  She also had me trim her pussy hair.  Since Randall had left our life, she had let it grow back until it covered her slit with a neatly trimmed triangle.  Why?  She’d found out that Jason preferred a full bush.  After I finished bathing her, she stepped out and I helped her dry off.
The party next door was in an hour and so we began to dress.  The lingerie she’d bought us was very sexy.  Her set included a sheer turquoise nylon thong, edged in navy blue lace.  The dark hair of her neatly trimmed pussy was visible through the nylon.  The set included a matching garter belt and shelf bra, which I helped her put on.  The set she’d bought for me was identical, other than my panties were boy shorts and my bra was a full cup.  She had also purchased a sheer, light blue slip for me to wear.  We each attached dark black stockings to our garter straps.  I, of course, wore men’s clothes over the top of my sexy lingerie set.  My cheerleader had bought a short navy blue pleated skirt with a red and white striped top.  She looked very patriotic.  And sexy.  And hot.  I immediately thought that the men at the party were going to be pleased.  Until then, though, I simply thought she wanted to look nice for the party.  But when we began to leave to walk next door, my cheerleader pulled me to her and kissed me deeply.  Holding me closely she said, “I hope you don’t mind sweetie.  But I’m going to try to find someone to bring home tonight.  I’m in the mood for someone new.”  I didn’t know what to say.  I remember feeling apprehensive though, immediately thinking about the fact that we knew our neighbors quite well, and wondered what she had in mind.  As if reading my mind, my cheerleader said, “Don’t worry.  I’ll be careful about who I select.  I just wanted you to know my intentions.  And expectations.  Okay?”  I said that I understood, and so we departed, me now realizing that my cheerleader had sex on her mind.  The result was that every conversation we had with every male we spoke to was going to be colored, for me at least, through the prism of knowing that my cheerleader was on the prowl.
The party turned out to be huge.  There must have been 200 people there.  Our neighbors greeted my cheerleader and me, pointed us to where the bars were, and sent us out to mingle and get to know more of our neighbors.  Needless to say, I was tuned into how other men at the party were looking at my cheerleader.  She was not the only woman there who was beautiful and dressed sexily.  As I’ve mentioned, we live in a very nice neighborhood and the women tend to work hard at looking good.  But she was definitely drawing her share of looks.  I tried to act as though everything was normal, and if I judged my cheerleader correctly, she didn’t seem to act like she was especially coming on to anyone.  But I was preoccupied with her last words to me before we left home - she was, “in the mood for someone new.”  And so I found myself sizing up her options to myself, as I assumed she was as well.
We had been at the party for a few hours and had met several new people.  So far though, my cheerleader had given no indication that she was zeroing in on a particular man.  We had chatted with a few single men, but nothing my cheerleader had said or done gave me any clue that she had picked anyone.  We found ourselves alone on the back patio and she asked me if I’d seen anyone yet.  I looked at her with what must have been a twisted face of confusion at her inquiry and she laughed teasingly and said, “Come on!  I’ve seen you checking out every guy we’ve talked to since we arrived.  Is there anybody who strikes your fancy?”  I didn’t want to admit that I knew what she was talking about.  I replied, “My fancy?  I thought you were the one looking for someone.”  She laughed again, clearly having fun playing with me.  “I am,” she agreed.  “But surely there is someone you would like see me with?  Someone whose cock you’d like to suck for me?”  Her bluntness shocked me.  I was glad we were standing away from others when this conversation took place, and not solely because she said what she said about me sucking a cock for her.  No.  It was because I must have turned bright red from embarrassment from my cheerleader teasing me in that way. 
Then, pointing to a guy she and I had spent a bit of time talking to, she asked me, “How about him?”  The man she pointed to was named Dave, and he was a good friend of my next-door neighbor’s – a divorced airline pilot who was retired from the U.S. Navy.  He was a very handsome and manly looking man.  I had met him before this party and he seemed like a really nice guy.  I said, “He’s a good friend of Jack’s.”  (Jack is our neighbor.)  My cheerleader said, “Yes.  I know.  What do you think of him?” she asked, bringing me back to her initial question.  I thought my first response suggested that he might be risky.  So I was more direct, “Don’t you think he might be too close to Jack?”  My cheerleader was quiet for a minute, and then said, “I’ll make sure he understands our situation.”  Oh!  So she had decided.  “Okay,” I said.  “It’s up to you.”  “Hmmm,” she replied.  “I suppose it is.  Wait here.  I’m going to go talk to him.” 
Leaving me standing alone, my cheerleader walked over to talk to Dave.  I tried to move away so that it wasn’t obvious that she was leaving me to go talk to another man.  I saw a group of guys standing together where I could talk and still keep an eye on my cheerleader.  I saw her approach Dave and touch him on the arm, said something to him, and laughed, resulting in him laughing also.  I wished I could hear their conversation.  Left to imagine what she must be saying to him, I became distracted from the conversation going on among the group I was standing with.  One of the guys spoke directly to me, drawing me back in.  “Your wife sure looks good today,” he said to me.  I stammered in response, “Oh, yeah, I, guess she does.  I’m a lucky guy,” I added, to absorb the compliment that sounded more like, ‘I’d love to fuck your wife.’  The other guys agreed that she looked really good.  Suddenly, I wanted to disappear.  I was with a group of men all basically telling me my wife was hot while I was waiting for her to close the deal on taking one of the men at the party home with us to fuck.  Just then, my cheerleader waved to me from where she was standing with Dave, beckoning me to join them.  I excused myself from the guys and went over to her.
As I approached, she pulled me to her and hugged me.  “Hey!” she greeted me.  “Ready to leave sweetie?”  Dave was watching our interchange with interest.  What had she told him?  “Sure.  If you are.”  “I am,” she said.  As we left she said to Dave, “We’ll see you soon?”  Looking at me, Dave replied, “Sure thing.”  As we walked away from Dave I was wondering what she’d told him about us.  We passed through our neighbors’ house looking for our hosts.  When we found them we thanked them for inviting us.  Jack’s wife said, “I hope you guys got to meet some people.”  My cheerleader replied, “We definitely did Ann.  Thank you!” 
We didn’t speak until we got inside of our house.  Once inside, my cheerleader pulled me to her and kissed me deeply.  “Are you ready sweetie?” she asked, her excitement about what was about to take place obvious.  “I guess so.  The question is, what is going to happen?”  I was dying from worry about what she was going to expect of me.  Still hugging me, she said, “You mean, did I tell Dave you were a sissy?  The answer is that I did.  I wanted to be sure he wasn’t going to freak on us.  I actually think he’s looking forward to seeing you.  So I want you to go put on your maid’s uniform and greet him when he arrives.”  My psyche took an immediate nosedive.  My cheerleader was bringing into our lives a man who I was going to see many times in the future under circumstances where I would have to trust him to guard my secret.  I asked her if she was sure this was going to be okay.  I was very worried.  “Honey,” she said.  “I told you I’d be careful.  I’m confident that Dave isn’t going to say anything.  Now go get ready.  I think he’ll be here soon.”
Reconciled to what was about to happen, I went upstairs to change into one of my maid’s uniforms.  Dave, it seemed, was going to get the full treatment on his first visit.  I took off my male clothes and, leaving on the lingerie set I wore to the party, I filled my bra with my breast forms and then put on my black maid’s uniform.  I put on the blonde pageboy wig and applied some makeup, and then went downstairs to ready myself for the rest of the night.  My cheerleader was in our den sitting on the couch, drinking a glass of white wine.  There was a glass for me on the table.  When I walked in she complimented me on how I looked.  I could sense her excited anticipation.  She clinked her glass to mine and said, “To us.”  “To us,” I replied, filled with anxiety. 
It wasn’t long before the doorbell rang.  Dave had arrived.  This was really happening.  My cheerleader was about to fuck a new man.  And a new man was going to meet me as a sissy.  I’m curious as to whether those who read about sissies wonder if we ever actually settle in to our natures and treat situations as normal.  I know for me it has not been that way.  Despite that my cheerleader had accepted me as a sissy, and notwithstanding that I’d accepted that she cuckolded me, I still felt anxiety before each encounter with a man.  How would he treat me?  How would he treat my cheerleader?  The unknown always caused me consternation.  And so, filled with anxiety from the unknown, I got ready to meet my neighbor’s friend, Dave, again, but this time as my cheerleader’s sissy maid.
Lost in my personal anxiety was wondering how Dave would react to seeing me the first time.  When I opened the door to find him standing there, his reaction was stunning.  His eyes gave him away, as it was clear that he had not prepared himself for seeing me dressed as I was.  Shifting into full sissy maid mode, I curtsied and said, “Won’t you come in sir.  Mistress is waiting for you in the den."  Dave didn’t say anything, but entered our house and followed me into the den.  I announced him to my cheerleader and she stood to greet him.  “Dave!  I’m so glad you made it!  Won’t you come in?”  To me she said, “Sissy.  Please get Dave a beer.”  “Yes ma’am,” I replied and went to the kitchen for a beer.  By the time I got to the den to serve him he was already seated beside my cheerleader on the couch.
I served him his beer and then stepped back, waiting for a cue from my cheerleader.  I really had no idea what to expect.  Seeing the expectant look on my face, my cheerleader said to me, “Have a seat sweetie.”  And so I picked up my glass of wine and sat in a chair alone, watching my cheerleader cuddling up to Dave.  No matter what my cheerleader had told him next door, he still looked confused as to what was happening.  My cheerleader, however, seemed completely comfortable.  It was interesting really, when you think of it.  The two males in the room – I’m not counting myself as a man – were uncomfortable.  But the woman was in total control.  Of course, that is the way of it, isn’t it?  The woman being in control?  It certainly feels natural to me.  But it is sort of outside of the normal world view of things.  And yet, there we were.
She directed the conversation with Dave and me for a few minutes, engaging in small talk, as we sipped our drinks.  When she finished her glass of wine, she asked me to go get the bottle to refill our glasses.  By the time I’d returned, she’d already made her move and was kissing Dave.  She didn’t quit when I entered the room.  I filled her glass and mine, and then stood by, watching her kissing Dave.  As she kissed him, her hand was groping and rubbing what was clearly a substantial bulge inside of his trousers.  It began to dawn on me that my cheerleader might be getting ready to fuck him right there on the couch.  With me watching.  My cheerleader was getting extremely turned on by the second.  She broke her kiss and growled, “I want your cock Dave!  I want it!”  She began attempting to undo his belt so that she could get his trousers down.  “Help me Sissy,” she ordered me.  “Help me get him out!”  I hesitated.  I had no idea how Dave would react to me touching him in that way.  “Sissy!” my cheerleader hissed, her sense of urgency notable.  “Help me!”  Stunned into action by her sharp-toned command, I quickly stepped closer and then went to my knees to help her free Dave’s cock.  Our four hands working together, we undid his belt and then unbuttoned and unzipped his pants.  Dave revealed his response to me being involved.  Cooperating with us, he lifted his hips from the couch to make it easier for me to pull his pants and boxer shorts off.  As I pulled them to the floor his cock sprung upward and my cheerleader grabbed it in her manicured fist.  Without any hesitation, she immediately leaned over and took him into her mouth, engulfing him.  I couldn’t believe that events were unfolding as they were.  I was still on my knees in front of Dave as I watched my cheerleader suck his cock.  Suddenly, in a flash, she let Dave’s cock escape her mouth and pulled her blouse off, revealing her tits resting prominently in her shelf bra.  She told me to pull her skirt off of her.  As she lifted up, I reached to her waist and unclipped and unzipped her skirt, pulling it down to the floor.  “Lick me!” she urged me.  “Get me ready Sissy!”  I leaned in between her thighs and pulled her wet thong to the side and licked her pussy.  It was already soaking wet!  She was so ready!  And she knew it too.  Within a few moments she pulled away from me and sat on top of Dave, facing me.  Puling her thong to the side to permit Dave to enter her, she easily began settling her pussy down onto his eager cock.  I watched from the floor as he spread her open, sliding steadily inside of her.  She hesitated at the bottom, slowly rotating her hips on Dave, looking directly into my eyes, she moaned, “Oh God!  Dave!  You are soo big!  Soooo big!”  Slowly, again she rose upward, revealing Dave’s cock to me, kneeling only inches away, now shiny and wet from her pussy juices.  I was mesmerized at how easily and hungrily she took him, at how wide he spread her, at how her pussy lips embraced his fat cock.  Right before my eyes I saw that my cheerleader was going to her special place, a place where I suppose all women go when they are being well fucked by a man.  She was also watching me watch her.  “Lick me Sissy,” she suddenly commanded.  “Lick my pussy!”  I looked at her questioningly.  Really?  While she was fucking Dave?  “Please Sissy!” she pleaded.  “Lick me!”  Slowly, I leaned in between Dave’s thighs, unsure that I should do so, but understanding that I must.  Was I scared?  Yes.  But did I want to do this?  Oh yeah!  My cheerleader settled her pussy on Dave’s lap, his cock completely engulfed within her.  As she sat with him fully impaling her, I licked her pussy.  She tasted delicious!  “Oh yes!  Sissy!  Yes!  Don’t stop,” she said as she began to lift up again, revealing Dave’s hard, wet, cock as she did, my mouth and tongue remaining in contact with her engorged slit.  I drove my tongue further inside of her, simultaneously feeling the soft folds of her pussy and the hot, hardness of Dave’s cock.  Dave grunted his appreciation from behind my cheerleader.  I remember feeling thankful that I could not see his eyes – that he could not see my eyes.  My cheerleader, however, was a different story.  Her eyes were locked on me, her arousal from being penetrated by Dave’s thick cock enhanced from watching her sissy husband pleasuring her with his mouth as she was being fucked.
Slowly, as if to draw out her pleasure, my cheerleader rose up and then settled back down, each time sinking Dave’s cock firmly within her pussy, my mouth and tongue constantly massaging her aroused sex as I continually felt Dave’s fat member with my tongue.  I was no longer feeling embarrassment at being a guy dressed up as a girl.  I became lost in the act, happy that my cheerleader seemed so pleased.  On one lift upward, my cheerleader rose until Dave’s cock slipped out of her pussy.  Kneeling as I was between his thighs, the result was that his huge cock fell forward against my face.  Reflexively, I grabbed it.  My cheerleader’s viscous fluid covered him.  He was more than wet.  He was gooey and slick from my cheerleader cumming on him.  “Suck him Sissy,” my cheerleader told me.  “Taste him.  I know you want to.”  Not arguing with her, I leaned forward and wrapped my lips around his head.  God!  He tasted amazing!  The unmistakable flavor of my cheerleader’s arousal covered him!  I wanted more!  I let him slide further within my mouth, dazed by the combined stimuli of being filled with a dick and tasting my cheerleader’s cum.  Withdrawing, I licked his length, hungry for her juices.  I wanted it all!  My cheerleader interrupted me, telling me to put him back inside of her.  Reluctantly, I did as she wished, positioning his huge cockhead at the mouth of her still hungry pussy, and held him there as she took him inside of her again.  Without being asked, I leaned in and began licking and kissing her pussy, slipping my tongue inside of her so that I could feel Dave’s cock as it moved in and out of her.
I could sense that my cheerleader’s rhythm was changing as she began to move faster, up and down, up and down, moaning and groaning as she did.  Her hands were holding onto the back of my head, forcing me to maintain contact with her pussy and Dave’s cock.  Their mutual orgasm was imminent!  I could feel it with my tongue.  Dave’s cock was throbbing and then, in a flash, I felt him pumping his sperm inside of my cheerleader.  Her head thrown backward, she cried out, “Oh Dave!  Oh fuck!  Yes!  Your cum is so hot!  Fill me!  Fill me!  Yes!”  Throughout, her grip on my head did not relax.  In fact, if anything, she held me tighter against their union.  I could already taste Dave’s cum dripping from her.  My cheerleader slowly relaxed from her orgasm, but she remained on Dave’s lap, his spent cock lodged within her.  She lifted a few inches, and as she did more sperm oozed from within her, coating Dave’s cock with his cream.  “Lick him Sissy,” my cheerleader told me.  “Clean his cock for me.”  I licked the base of his cock while he remained partially within my cheerleader.  She lifted higher, revealing more of his cum-covered cock – more cock for me to clean.  She then settled back down, re-coating his cock with his sperm, and lifted again for me to clean him more.  Repeatedly my cheerleader rose and settled, each time rewarding me with more of her lover’s semen, his flavor immeasurably enhanced by my cheerleader’s own orgasmic release.  Eventually, she let him fall out of her and I took him into my mouth again, cleaning him completely.  Then, my cheerleader moved forward a bit, her eyes imploring me to suck her pussy clean.  I opened my mouth and locked onto her, sliding my tongue within her, licking and sucking Dave’s remaining cum out of her, Dave’s cock lying in contact with me just under my chin.
I don’t know what more I can say about this moment in my life with my cheerleader.  I will only say that I doubt my written description does it justice.  It was an incredibly erotic event.  However, what may be missing is an adequate explanation of how I felt afterward.  I had, obviously, been concerned about my cheerleader bringing home a man who we would socialize with in the future, and in the company of people we had come to know rather well.  How uncomfortable would things be?  And yet, in the moment, all of that was forgotten.  When my cheerleader climbed off of Dave’s lap, and his eyes met mine for the first time, I felt a deep sense of shame and embarrassment.  I wondered what he was thinking about me.  Did he see a fag?  Or, was he able to suspend disbelief and see me as the feminine creature I saw myself as?  Did he comprehend the love my cheerleader and I shared that permitted us to do something such as this together?  Obviously, he had enjoyed fucking my cheerleader.  All of her men did.  And he seemed to have no complaint about me joining in, including sucking his cock clean.  But he and I had talked, in the way guys talk around guys, many times in the past.  We had discussed playing golf together.  How would he see me now?  These thoughts were all swirling around in my head, answers to which were not immediately forthcoming.
Meanwhile, my cheerleader was cuddling close to Dave, showing her own feminine appreciation to him for pleasing her so.  Nuzzling into his neck she asked, “Can you spend the night?”  Dave looked at me, a slightly puzzled expression on his face, almost as if he thought I had something to say about her invitation, but I said nothing.  I didn’t have anything to say about it.  It was my cheerleader’s decision.  “Please?” she asked.  “Sure,” he finally replied.  “If you want me to.”  “I do,” she cooed to him.  “I really do.”  To me she said, “Sissy?  Would you please prepare our bed?”  Standing, I replied, “Yes ma’am.”  “Thank you sweetie.  We’ll be up in a few minutes.”  I curtsied and left them alone while I went to turn the bed back.  I wondered what the conversation between them was about.  Were they talking about me?  Whatever it was, I believed that Dave was likely hooked on my cheerleader, just as Jason had become.  Her utter sexual submission to them seemed irresistible.  She had a way of letting any man who was fucking her believe he was amazing, which, in Dave’s case, seemed to be true. 
I had just finished turning the bed back and setting out cool bottles of water next to each side of their bed when my cheerleader walked into our bedroom, alone.  She smiled at me as she entered.  “Thank you Sissy,” she said.  Then, she kissed me sweetly on my mouth and said, “I told Dave to wait until we were ready for him.  Will you pick out a baby-doll for me to wear?”  I said I would and went to her dresser to select something while she began to undress.  I picked out a sheer baby blue negligee that I knew she liked.  When I brought it to her she was naked.  I helped her slip it over her upstretched arms and watched as the soft nylon settled over her, not concealing her nakedness, but enhancing it.  Her large breasts and erect nipples poked prominently forward.  Again, she pulled me to her and kissed me.  “I love you Sissy,” she whispered.  “Thank you for giving me this.  I hope you know how much I appreciate it.”  I felt a bit embarrassed and even blushed.  I answered, “I want you to be happy.”  “I am,” she assured me.  “I am.”  Then, she asked me to put on a nightgown also, and told me she wanted to watch from our bed while I undressed Dave and prepared him to fuck her again, just as I had in the past with Randall and Jason.  Knowing she wanted it, I could not deny her, and so I went to my dresser and picked out a sheer white negligee to wear.  I took off my maid’s uniform and, leaving on the lingerie I’d worn to the party, I slipped the baby-doll over my shoulders.  “You look pretty,” my cheerleader said to me.  “Tomorrow I am going to unlock your chastity cage and let you make love to me.”  As if she knew that, after telling me that, I would do anything for her, she asked me to go downstairs and to bring Dave to her.  She wanted me to have to present myself to him looking as sissy as I could possibly be, wearing lingerie and a sheer nightgown that would surely reveal to him that I was locked in chastity as well.  And then, she told me, she wanted to watch me fluff him for her  - to get him ready to fuck her again.  As embarrassing as I knew it would be to do what she asked, and knowing that for the foreseeable future, whenever I was in Dave’s company in a social setting, he would know I had sucked his cock so he could fuck my wife, I agreed to do what my cheerleader asked of me.
Wearing high heels and a sexy nightgown that revealed my pretty turquoise lingerie, I went downstairs to bring Dave to my cheerleader.  Dave was waiting alone in our den.  He had put his pants back on.  Thank heaven!  He did a double take though when he saw me.  I had done this before, and so I knew that the best way to get through it was to just face the music and do it right.  I curtsied and said, “May I show you upstairs?”  He smiled uneasily and said, “Okay.”  He stood and followed me out of the den.  I wondered what he was thinking as he followed me upstairs to my waiting cheerleader.  I was certain that he was going to be pleased with what he saw when he saw her again.  I entered the bedroom with Dave close behind me.  I curtsied to my cheerleader and presented Dave to her.  Laying on our bed, on her side, her negligee concealing nothing, she smiled and asked me to prepare him for her.  I turned to face Dave and asked, “May I sir?”  I don’t know whether he really understood what he was consenting to, but he said, “Sure,” and so I began to undress him for my cheerleader.  I stooped before him to help him step out of his trousers and boxers, which had me at eye level with his cock when it popped free.  I took him in my hands and leaned close to him to kiss it.  He was hot and throbbing.  Taking my time so as to give my cheerleader a show, I slowly licked around his cockhead, making him wet, feeling him grow bigger as I did so.  I licked down his shaft and sucked his ball sack into my mouth, softly mouthing him while gently stroking his cock.  Then, licking back to the tip of his cock, I opened my mouth wide and took him inside, holding him there as I swirled my tongue around the shaft that would soon be pounding my cheerleader.  I bobbed slowly and gently upon his ever thickening cock, taking him to the back of my throat and then letting him slide out gently, making sure to allow only my tongue and soft, wet lips make contact with his beautiful cock.  I knew that my cheerleader was watching me suck Dave’s cock, but my focus was upon him. 
After a few minutes I began sliding rhythmically up and down his wet shaft, and he was responding to me, beginning to fuck my face as I sucked him.  It was then that my cheerleader told me to stop and told Dave to come to bed.  Still on my knees on the floor by our bed, I let him go to her.  As he climbed onto our bed my cheerleader turned over, onto her stomach, and then pulled her knees up under her, presenting herself to Dave so he could enter her doggie style.  She never told me to leave, and so I watched from the floor as Dave moved behind her and, positioning his thick, wet cock against her wet slit, he pressed into her.  I was amazed as he spread her wide, her lips hugging him as he disappeared inside of her, drawing a loud gasp and moan from my cheerleader.  Dave began moving in and out of her, withdrawing almost all of the way, and then disappearing inside of her again.  With each re-entry my cheerleader’s responses grew louder and more excited.  Her head was buried into her pillow, bracing herself for each insertion of his fat cock.  Meanwhile, my own penis was throbbing as it grew within the chastity cage I wore.  I couldn’t help myself.  I was very turned on watching my cheerleader being so thoroughly and satisfyingly fucked.  I watched from my knees, the two of them now oblivious to my presence, as Dave reached orgasm, along with my cheerleader, and began pumping his seed inside of her.  When he finally pulled out, his cock was covered with cum, and more leaked out of her pussy.  My cheerleader looked at me and said, “Clean him Sissy.  Then me.”  Obediently, I stood and went to Dave who willingly presented his goo-covered cock for me to lick and suck clean.  I could feel him watching me submit myself to him as my cheerleader had told me to do.  When he was clean, I moved behind her and stuck my face up into her pussy and began licking and sucking Dave’s sperm out of her.  When I finished, she told me to go to bed, but to bring them breakfast in bed in the morning.  Dave must have thought he’d died and gone to heaven.  He’d fucked my cheerleader twice already, and now, after dismissing her sissy husband, she was probably going to fuck him all night long, which is what happened.
I went to bed alone, knowing my cheerleader had brought a third man into our bed, although now only two were in our lives.  I know.  I said, “only two were in our lives,” as if having your wife fucking other men can be reduced to a number like that.  My cheerleader had established a new tone to her cuckolding of me.  She was going to cuck me when she wanted and with whom she wanted.  I had to have faith and trust that she would be careful.  And while I was worried about Dave, my cheerleader turned out to be right about him.  He has kept our secret safe.  And he’s become a pretty good friend.  He doesn’t judge me.  We can still talk about sports and other common male interests that we share.  But when I’m in sissy mode, and he is at our house to be with my cheerleader, he treats me like a sissy.  And I’m okay with that.
As promised, the next day, after my cheerleader spent a leisurely morning having breakfast in bed with Dave, and fucking him some more until he left to return to his life, she gave me a very nice reward.  We cuddled together after I cleaned her pussy, and then, she released me from my chastity cage.  I must have been making her very happy because she was intent on rewarding me for all that I was permitting her to do.  She teased my penis, kissing it and gently sucking it.  She brought me to the edge over and over, but always seemed to know just when to stop.  And, although I desperately wanted to cum, I suspected that once I did, it might all be over and I’d be placed back inside of my chastity cage, and so I was willing to let her draw things out as long as she wanted.  Eventually, though, she let me put my penis inside of her.  She had been stretched out pretty good by Dave, and so taking me inside of her was not difficult.  Still, I enjoyed feeling her wet pussy caress my sissy penis until I finally had an orgasm and filled her with my cum.  My cheerleader loves the feeling of hot sperm filling her pussy, so even if I wasn’t as big as Dave, I was still able to give her something that she enjoyed.  After I came inside of her, she straddled my face and let me lick and suck her clean.  Instead of locking me back up though, she left me free for the rest of the day and night, as we snuggled and cuddled in bed.
Dave’s flight schedule was fairly regular, but he was not in town every night.  But, when he was, it was almost a sure thing that he would come by our house to fuck my cheerleader.  For a while, my cheerleader was being fucked, by either Dave or Jason, at least three nights per week.  I had long since accepted my role as her sissy cuckold husband, as well as my role as her fluffer.
This last entry about my sissy journey is bringing us closer and closer to the present.  There has been one other very significant event that occurred a couple of months after my cheerleader brought Dave to our bed.  And I‘ll tell about that soon in my next entry about my sissy life.








19 comments:

  1. It's amazing to me that your cheerleader can and did continue your sissy cuckold journey. Not only continue, but raising the stakes along the way. Having a man was a significant step. A second man is another milestone. Now having a man you've already experienced in your male social circle... wow! I can't imagine this being laid out and planned any better. Each step taking you further along your sissy path making each previous step a more normal part of your life.

    I still love reading your life's story Leeanna and await your next chapter!

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    1. I really don't think she planned it out. Going there at all was my idea. I believe what happened was that once we began she came to realize how inch she enjoyed it. She suddenly had men who were ready, willing and able to provide her immense sexual satisfaction, and yet she still had a spouse who provided her creature comforts and complete emotional support while also loving her in the tenderest way. And she gave something to me as well - the freedom to be as feminine as I wanted to be. And it simply grew. Thank you for your thoughtful comment.

      Kiss kiss,

      Leeanne

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  2. Another lovely episode Leeanne. Beautifully written as always. You and cheerleader have the perfect lifestyle. I look forward to reading your next instalment.

    One quick question ? Are you ever tepted or would cheerleader allow you to be fucked by a real man or even 1 of her lovers ???

    Love Tanya xxxx

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    1. Dear Tanya,

      I'll admit that I fantasize about it. But I don't believe my cheerleader has it on her radar for me. She loves watching me suck cock, but I honestly think that is driven mainly by her knowing I'm submitting to a man for the purpose of preparing him for her. If one of her men ever got it in his head to take me that way, and said something to her though, I could see her giving it some thought.

      Kisses,

      Leeanne

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  3. That was so nice to read, Leeanne! Thank you so much for sharing it.

    And of course I'm looking forward to seeing your reply to Tanya as well.

    xoxoxo

    Christine

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    1. Dear Christine,

      Well, you got your reply to Tanya! Thank you for your sweet comment.

      Smooch!

      Leeanne

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  4. Thank you Leeanne, you articulate so well the thoughts, desires, doubts and anxieties that come with a Sissy cuckold life!
    We have had men who just couldn't deal with it, where my presence was a deal-breaker and we've had men who were indifferent to me and we've had a few that were really....enthusiastic about my participation!
    I love each installment of your journey and have often re-read some of your older posts! I look forward to your next post!
    Now I have to go put on fresh panties, these are decidedly damp!

    Love and Sissy Kisses
    Kaaren

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    1. Dear Kaaren

      Thank you sweetie. I have been blessed that the men my cheerleader have chosen have not only accepted my role in their relationship with her, but embraced it. On the other hand, she makes it soooo worth their while, if you know what I mean.

      See you at the next meeting of SCA.

      Kiss kiss,

      Leeanne

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  5. Beautiful, as usual. The love that you and your cheerleeader share is something very special.

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    1. Thank you Lost Sissy! We really are a lucky pair!

      Hugs,

      Leeanne

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  6. I've followed your story for some time. Incredible.

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    1. Thank you. I'm glad you are enjoying it.

      Xoxo,

      Leeanne

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  7. Love this latest and very detailed account. Your Cheerleader is wonderfully inventive and very skilled in choosing who she seduces ;-)

    My only regret is hearing that we're almost up to date on your past adventures, though of course there'll always be new ones, of that I'm sure!

    I too would love to see you used as a sissy-bitch by your lover's chosen Bulls. Is that mean of me?

    Hugs n sisterly kisses,
    Gigi, slut

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  8. Such a remarkable tale. It is only in the last few weeks that i found your blog - which i love. Then i discovered your entries describing your evolution as a sissy and your relationship with your cheerleader. i have faithfully read every entry over the past week or so. For myself over the past few years i have progressively discovered, nurtured and embraced the woman inside me, step by step becoming more feminine, loving the truth of becoming more and more of a sissy each day. So many changes as i leave my former self behind. Your story is special and goes well beyond my own experiences. Yes my sissy clit grew in size many times in reading your accounts as i recognize my own desires in so much of what you describe. Still, you tell of the points of intersection between desire and reality, the hesitation and the fears, the acceptance, and the changes within yourself. And at the center is your relationship with your cheerleader. i admire your courage, envy you for many of your moments of passage, and wish you well in the future. Thank you ever so much for sharing. We all have our journeys and yours is certainly special.

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    1. Dear Susan,

      I am so glad that you follow my blog. I love your thoughtful comments. I am especially pleased to hear that you have enjoyed reading my account of my personal sissy journey.

      Kisses,

      Leeanne

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  9. I really enjoyed reading about your experience my dear Leeanne. The way you obey your cheerleader, and only wish to please her and the real men in her life is quite arousing =) You have the perfect attitude as a sissy cuck!

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    1. Jessica!

      You've read my entire story? Oh my! And you like? thanks!

      Kisses,

      Leeanne

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    2. Oh yes sweetie, I think your blog is great! I also wanted to thank you for linking to my site. I finally got mine updated with a link to yours now. I also put your blogger and tumblr rss feeds on the main page. So some of your newest posts will randomly show up in the 'My Favorite Femdom and Sissy Websites & Blogs' feed. I think it's really cool we can help promote each other like this =)

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    3. Well! Haven't you been the busy little sissy! Thank you sweetie!!

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