Cheerleader Flirts - With Purpose

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

I don’t know if anyone will recall that I mentioned earlier, in the post titled, “Cheerleader Cucks Sissy,” that my cheerleader is a bit of a flirt at parties.  It wasn’t something that I’d always taken note of early in our relationship, but at the office party we hosted where she first introduced me to Randall, I picked up on it and then reflected back to past parties and it struck me that she seemed to enjoy flirting, in an innocent way, with guys at parties.  Well, her flirty nature paid dividends for her as we moved forward in our newfound cuckold relationship.

 Last Christmas was when my cheerleader made her first move.  I had been under the assumption that my cheerleader remained in contact with Andrea, primarily because it just seemed to me that they had a connection as women from our time with her, but also because it seemed my cheerleader continued to take new steps forward where she and I were concerned.  In any event, my cheerleader began talking about being with other men a bit more frequently.  Where we live, each Christmas, there is a neighborhood holiday party.  As I’ve mentioned before, we are fairly new to the neighborhood, so we don’t know a lot of people.  Added to our newness, unlike many of the families that lived in our neighborhood, we did not raise our children there, a fact that, interestingly, seems to inhibit opportunities to meet new people.  I had never realized how big of an impact children had upon ones social life, but it was a good method for meeting new people.  Whatever, we were going to the holiday party last year, as we will this year.

During the week leading up to the party my cheerleader began teasing me about meeting someone – and by “someone,” she meant a man.  I took it in stride thinking it was just more teasing, something she enjoyed doing to me.  However, on the afternoon of the party she went out to have her hair done up especially for the event.  Then, when she returned home, she had me join her in the bathroom to help her “get ready,” just as if she were going on a date with Randall.  It was then that she asked me how I’d feel if she found someone to bring home with us.  I thought she was kidding, but she wasn’t.  She told me that she thought it might be time – time for her to branch out beyond Randall.  My reaction was predictable.  I became anxious, nervous, uncomfortable, and my penis swelled within its chastity cage.  I told her that if that was what she wanted, then okay.  I remember that she merely smiled at me as if to say that she suspected I would acquiesce.

My cheerleader had gotten a pedicure and manicure earlier in the day when she had her hair done.  But she let me shave her legs and trim her pussy for her, an event that always felt different to me when I knew I was preparing her to be fucked by Randall.  On this occasion I experienced that same erotic response.  When my cheerleader dressed that evening I discovered that she had purchased brand new lingerie - panties, garter belt and bra - red satin trimmed in black lace – for the party.  She had made plans.  She also had purchased a new set of lingerie for me, similar to hers, to wear beneath my suit – pink satin trimmed in black lace.  I recall wondering at the time whether this was simply more teasing by my cheerleader.  It turned out that she wasn’t.  She was on the prowl.  Watching her that evening was a bit of an eye opener for me.  Despite having seen her flirt before, on this night, she flirted, but with purpose.  It was a new thing for me to see in her.  Like many beautiful women do, she had a way – a way that had a certain effect upon men.

She wore a very short and sexy red holiday dress, her pretty black nylon covered legs stretching beneath her hemline to a pair of matching red high heels.  Around her neck she wore her pearl necklace that she kept my key on, an adornment that never escaped my notice.  This annual holiday party was a big neighborhood affair.  I don’t recall whether I’ve mentioned this before, other than to say that we live in a nice neighborhood, but there are some fairly accomplished inhabitants who live there.  We live outside of Washington, D.C. – I know that I have mentioned that – and so there are people whose livelihoods revolve around the political sphere that finances much of the Northern Virginia and Maryland area that makes up the Beltway.

We arrived at the same time as a few of our closer neighbors and my cheerleader received compliments about how she looked, from the men and the women.  She really did look especially pretty for this party.  I was proud to be seen with her.  And yet, I was feeling the same nervousness and anxiety that I’d felt when my cheerleader first cuckolded me with Randall several months before.  I had grown used to him being around and having her on a regular basis.  But on this night, I was experiencing those same emotions anew as I wondered how my cheerleader intended to “find” someone new.  Of course, I still had not discounted that she might be toying with me.  So, I wasn’t completely certain that anything would actually happen.

Initially, upon our arrival, we drank and chatted with some people we knew, and were introduced to some new people as well.  My cheerleader and I had mutually acknowledged that we needed to continue to try to branch out to expand our social circle some.  An hour or so into the evening, I noticed from the corner of my eye a very handsome man standing among a group of men and women, two of whom were people we had met, and he was definitely looking our way – I suspected specifically at my cheerleader.  I glanced at her to see if she had noticed him yet.  She smiled at me as she caught me looking at her. 

“Shall we go over there?” she asked me.  She knew what I was thinking.  I told her if she wanted to that would be fine.  We walked over to join the group and our friends there introduced us to the others, including the man who had been eyeing my cheerleader.  By anyone’s definition, he was a fine specimen of the male gender – approximately six-four, maybe 220 pounds, thick blonde hair, and obviously athletic.  My cheerleader’s eyes were alive as she held her hand out to take his in greeting.  If he had any sense of intuition, he knew then that she was interested in him, despite that her husband was being introduced along with her.

His name was Jason, and it turned out that he was well connected in D.C.  He was the chief of staff for a United States Senator.  I’m not going to say anything about where the Senator was from, or whether the Senator was male or female.  I probably shouldn’t even reveal that much.  I just feel that it was significant that the second man my cheerleader cucked me with was someone such as Jason and that leaving out such an important fact would diminish the narrative.  We stayed in this group and talked for a long time, sharing details about our lives.  My cheerleader was clearly enthralled with Jason, quizzing him about his work on The Hill.  I sensed that she may have decided that he was going to be the guy, especially when she discovered during the conversation that he was unmarried.  I knew my cheerleader would never choose a married man, as she had been hurt once before by her first husband cheating on her, so I did not think she would be the cause of same thing for another woman.

After a while, the others who were part of our conversation with Jason drifted off to talk to others, and for a moment, we found ourselves alone with him.  It was then that my cheerleader really turned it on.  She asked him if he was dating anyone special and he told her he wasn’t.  When he said that, she expressed her surprise that someone as handsome and eligible as he was did not have women falling all over him.  He actually acted a bit embarrassed when she said that and explained that he really was very busy with his job.  At that moment my cheerleader looked at me and said, “Sweetie?  Would you mind going to get us all fresh drinks?”  I noticed the way Jason looked at me when she asked, almost as if he sensed that something different than he was used to had just taken place.  I understood right away that she wanted a few minutes alone with Jason.  My stomach was swirling with butterflies as I began to believe that my cheerleader really was going to attempt a move at this holiday party.

I left the two of them alone and went to one of the bars to get fresh drinks.  The home of the couple that was hosting this year’s party was very spacious.  Bars were set up in a few rooms throughout.  I decided to give my cheerleader a bit of time to talk to Jason alone, so I went to one of the bars out of view from where they were talking.  Honestly, at the time, I still did not think that my cheerleader would really do anything.  But I was nervous nonetheless, wondering whether she might.  The line at the bar I went to was fairly long, and so I stood alone waiting to get us drinks.  When I got our drinks, I walked back to the room where I’d left my cheerleader and Jason.  However, they were not where I’d left them.  Holding three drinks in my hands, carefully so as not to spill them, I began scanning the room.  I was feeling extremely self-conscious at this point, alone at the party with my cheerleader alone with another man.  My cheerleader and I did not know a lot of people – but we knew some.  Had anyone seen her walk away with another man?  I slowly moved about, looking for them, anxiety now beginning to get the better of me.  Eventually, I walked onto the back patio where the hosts had set up several large outdoor heaters for guests who wanted to smoke and still remain warm.  The back yard patio and garden was magnificent.  I glanced around and then saw them, standing to the side near a heater, talking alone, my cheerleader’s face aglow as she spoke animatedly with Jason, who seemed equally enthralled with her.  I approached them with our drinks, working myself up to act as if I was completely cool with whatever was happening, and yet not knowing what really was happening.  Had my cheerleader made a move?  I didn’t know.

They greeted me as I handed each their drink.  I said, “I thought I’d lost you there,” trying to sound casual about their disappearance.  My cheerleader answered, “We just thought we’d get some fresh air.  I figured you’d find us.”  Jason thanked me for his drink.  As he did, I thought I noticed something in the way he looked at me.  We chatted together for a few more minutes and then my cheerleader said to me, “So, are you ready to go home sweetie?”  Taking her cue, I said, “Sure.  If you are.”  “I am,” she told me.  Then, to Jason, she said, “See you in a bit?”  That’s when I knew.  She had invited him to our house.  Jason hesitated, locked eyes with me for a split second, then said, “If you’re sure,” as if he wasn’t convinced that my cheerleader really expected him to accept her invitation.  “I’m sure,” she said as she took my hand and said, “Come on sweetie.  Let’s go.”

My cheerleader and I began to make our way from the party.  We stopped to say our farewells to a few of the people we knew who were still there.  Then, searching out the hosts, we found them and thanked them for hosting and telling them how wonderful everything was.  To be truthful, at this point, I was in a fog, contemplating what I realized was about to occur, for the second time.  My cheerleader was going to make love with yet another man, all with my consent.  But what else had she told Jason?  That was the part that was causing me the most angst.

Holding hands as we left to go to our car, we did not speak.  I could sense that my cheerleader was feeling anxious about what she was about to do.  Until that moment, I had not considered that I wasn’t the only one who felt anxiety concerning a step such as this one.  She wanted this.  But she was nervous also.  I opened her door and helped her climb in, then got in and started the car to drive the few blocks to our home.  We drove in silence, me not knowing what I should say, and her I have no idea why.  When we walked in our house I finally spoke.  “So, are we having company?”  My cheerleader looked at me and said, “Yes.  We are.  Are you okay with that?”  Was I okay with it?  I found myself having the same debate I’d had when this situation first presented itself with Randall.  If I wasn’t okay with it, I probably should have already said something.  She had already invited Jason over.  “Does he know about me?” I asked, not saying it, but meaning, ‘Does he know I’m a sissy?’   My cheerleader looked down, avoiding my eyes, but then looked up and said, “Yes.  I told him.”  Then, adding,  “I think he’s okay with it.”  So there it was.  My cheerleader had told yet another person that her husband was a sissy, and that person would be in our house soon.  I remember saying to her, “Okay.  What shall I do?”  She told me then that she wanted me to go upstairs and change into a maid’s uniform, put on some light makeup, but no wig, and to prepare to sleep in the guest room after they went to bed.  But first, she wanted me, dressed as a sissy, to greet Jason at our door when he arrived, so he would understand that I was completely on board. 

I want to try to explain how I felt in that moment.  I have tried, throughout this narrative, to describe my feelings as much as possible, to attempt to convey what was going on inside of me – emotionally, mentally and physically – when my cheerleader was treating me as her sissy husband.   This is difficult to do.  As I have mentioned, I had grown used to Randall.  Randall had a hand in bringing Andrea into our lives, and so I viewed him as someone who understood us – my cheerleader and me.  But this new man – Jason – he was different.  He was a stranger to us only a few hours ago.  In addition - and this is why I felt it necessary to reveal what he did for a living – he was SOMEONE.  Not just some man - but a well-connected and important man who was going to enter our home, find me dressed as a sissy, and then, with my consent, fuck my cheerleader.  Randall was someone my cheerleader met through work.  They were familiar with each other long before they became intimate.  I’d met him before they became intimate.  This man was different.  He represented something else to me.  He was the embodiment of my cheerleader telling me she wanted to fuck other men – not just another man specifically (Randall) – but other men, generally.

I remember when she told me what she wanted me to do that I nodded.  I simply nodded my head in acquiesance, said, “Okay,” and walked upstairs to do as my cheerleader had asked.  I went into my closet, removed my suit, selected my black French maid’s dress, a white petticoat, and black high heels, and returned to our room to dress.  Leaving on the lingerie that my cheerleader had purchased for me to wear to the holiday party, I filled by bra with my breast forms, stepped into the slip and high heels and pulled the dress over my head, settling it over the fluffy crinoline slip.  I went into our bathroom and applied some mascara to my lashes, dabbed some rouge on my cheeks, and applied red lipstick.  Then, finally, I opened the drawer in my dresser where I kept them, and picked out a nightgown to wear to bed and carried it into our guest room.  I returned to our room and turned the covers back on our bed for my cheerleader and Jason, then went downstairs where I found my cheerleader in the kitchen preparing some snacks.  She smiled at me when I came in.  “You look pretty Sissy,” she said.  She approached me and kissed me softly on my lips.  “Thank you sweetie” she added.  I smiled uncomfortably, but replied, “You’re welcome.”  I then helped her carry the snacks into the den.  It appeared that she did not plan to simply jump in the sack with Jason, although it was clear that she was fully committed to taking him to our room. 

As we prepared for Jason’s arrival, I felt like time was dragging.  I even began to wonder whether Jason might chicken out – that the thought of going to someone’s home he’d just met and having sex with a woman whose husband was a sissy was more than he could actually deal with.  But then the front doorbell rang.  He didn’t back out.  He had come after all.  My cheerleader watched me and then said, “Go greet him Sissy.  Bring him in here to me and then offer us drinks.  Don’t forget to curtsy.”  Fuck!  This was actually going to happen!  I was about to be cucked for the second time.  My stomach was in knots!  I was a complete wreck inside as I walked in my high heels to welcome Jason into our home and lead him to his prize – my cheerleader.  Numbness overwhelming me, I opened the door to the man I’d only just met, curtsied, and said, “Good evening sir.  Won’t you come in?”  The expression on his face revealed that he was at least as overwhelmed as I felt.  “Hi,” he managed, the confusion of seeing me in this completely different light evident. 

I led him to my cheerleader who was sitting alone on our couch in the den.  “Mistress,” I announced.  “Mr. Johnson is here for you.” (Jason’s last name is not really Johnson.)  My cheerleader stood to greet him.  Smiling sweetly she said, “Hello Jason.  I’m glad you came.”  He walked to meet her at the couch and, as she had with Randall in the past, she set the tone for him – and me – immediately by giving him a full kiss on the mouth, holding him there long enough to make her intentions clear.  When they broke, she said to me, “Sissy?  Would you get us drinks please?”  “Yes ma’am,” I answered and asked what they wanted, and left them alone again while I prepared their drinks.  When I returned they were sitting together, closely, on our couch, his arm already around her shoulder.  I served them and then asked if they needed anything else.  My cheerleader said they were fine for the moment and dismissed me.  I went into the kitchen alone to wait, for what I really did not know.  I assumed at some point she would take him to bed.  I just didn’t know when.  I had no idea how my cheerleader intended to handle this entirely new situation of bringing home a man she had only just met, but seemed intent to fuck.  All I can tell you is that time was dragging on for me.  I tried my best to hear what they were saying, but it was quiet in the den.  It turns out they had been making out, as a way to break the ice I suppose.  After a while my cheerleader and Jason came into the kitchen together and she said, “We’re going to bed sweetie.  Will you clean up?  Then you can go to bed if you’d like.  We’ll see you in the morning.”  ‘We’ll see you in the morning,’ she’d said.  Jason was going to spend the night.  There it was.  I was left standing by once again while a man took my cheerleader to our bedroom to fuck.  “Yes ma’am,” I replied, dipping into a curtsy as I knew she expected.  Jason was along for the ride.  I don’t think he knew what to think.  He only knew the one thing that mattered – he was about to fuck another man’s wife and with his full consent.  They went upstairs and I heard our bedroom door close behind them.

As instructed, I cleaned up, putting away the snacks and loading their dirty glasses into the dishwasher.  Then, I went upstairs, alone, to our guest room, took off my dress and lingerie, put on my nightgown, and crawled into bed, imagining what my cheerleader was doing with Jason in our bedroom down the hall.  I could not sleep.  I turned on the television to pass the time and simply to hear other human voices.  They were going to ‘see me in the morning’ my cheerleader had said.  I was worried what she meant by that.  I eventually fell asleep only to be awakened by my iPhone ringing next to me on the night table.  It was my cheerleader.  She greeted me good morning, then asked me to bring them coffee in bed.  I agreed and then asked what I should wear.  She told me to put my uniform back on.  It was nearly nine a.m. when she woke me.  I dressed as instructed and went downstairs to prepare coffee.  When it was ready, I loaded a tray, and went up to serve them in bed.  I knocked on our bedroom door and after my cheerleader told me to come in, I opened the door, scared to death at what I might find.  How would they be when I saw them?  I could still remember that first time I was invited into our bedroom by my cheerleader when she was with Randall, naked together in our bed, his huge cock lying in plain view for me to see.  Would she and Jason be similarly situated?

As I suspected, my cheerleader and Jason were in our bed together, obviously nude, only partially covered by the bedclothes.  My cheerleader was snuggled up next to Jason, her bare breasts on display.  Jason, for his part, seemed appropriately ill at ease.  This was obviously new to him and he did not know how to behave.  My cheerleader, on the other hand, seemed at home.  I could see her hand moving beneath the sheet, obviously massaging his cock right in front of me.  She was used to me serving her and Randall as her sissy husband.  She merely substituted one man for another man.  Entering with the coffee and trying to not stare at where my cheerleader’s hand was located, I curtsied, and then approached.  “Good morning,” I greeted them.  “May I pour your coffee?” I asked them.  “Please,” my cheerleader answered, watching me look at her fondling Jason’s cock.  To Jason she asked, “How do you take your coffee?”  He addressed me, trying his best to act like this was normal, “Just cream please.”  It didn’t strike me then how polite he was.  But, thinking about it, as I wrote this, I realized that Jason was a very refined man who knew how to behave in many different circumstances.  But he was not equipped for this one and so his natural default was to be polite and to treat me as he might anyone else who was serving him – with gratitude.  After preparing their coffee I asked if they needed anything else.  My cheerleader told me that would be all and dismissed me.  I went back downstairs and waited, drinking coffee alone while my cheerleader relaxed in our bed with her new man.  She’d done it.  She had not just been teasing.  She had really picked up a man at our neighborhood holiday party.  And, on top of that, she had managed to pick up someone who had a vested interest in being discreet about our secret.  I remembered wondering if she had been that calculating – or merely lucky in that regard.  We eventually discussed that thought, and she admitted that it was more luck than design, although once she’d heard what he did for a living the thought of the safety to us his job provided was not lost on her.

It was a little over two hours later when my cheerleader called me on my iPhone again.  She told me that Jason would soon be leaving.  He was taking a shower before he left.  She told me to see him off and to then come to our room.  When Jason came down, dressed in the clothes he’d worn the previous evening, but without his tie, he told me goodbye and then thanked me.  He really was polite.  Playing my role to the end, I curtsied and said, “You’re welcome.”  I closed the front door behind him and then went upstairs to see my cheerleader alone for the first time after she’d cucked me for the second time.  Our bedroom door was open.  I walked in and found her still in bed, smiling and waiting for me as I entered.  “Take off your dress honey.  Come to bed,” she told me.  I slipped my dress over my head, dropped the slip to the floor and stepped out, slipping my heels off as I did so.  As I crawled onto the bed she flipped the covers to the side and pulled me to her and kissed me full on the mouth, passion dripping off of her lips.  We kissed like that for a long time.  When she finally let me go she sighed and said, “Thank you so much baby.  That was so amazing!  Thank you!”  As I found myself doing with Randall, her gratitude to me for allowing her this freedom erased any lingering doubts I had about her cucking me.  I told her I loved her and that I was happy if she was happy.  She assured me was and then, as I expected she would want, I was directed downward and between her thighs where I tasted another man’s sperm directly from my cheerleader’s pussy.  I licked and sucked her for a long time that morning, bringing her to several gentle, but urgent, orgasms.  Afterward, my cheerleader unlocked my chastity cage and let me go inside of her for the first time in over a month.  I was so grateful to her for allowing me to enter her, even though I was so excited that I did not last as long as I wish I had.  After I finished cleaning her, we cuddled and slept all afternoon.  It was the best I’d slept in a long time and I needed it, especially after the fitful night I’d spent the night before.

Later, when we awoke, my cheerleader told me about her night with Jason.  She told me he was a really good lover.  He not only had a very big cock, and lasted a long time, but he recovered quickly (with some help she teased) and on the subsequent times lasted even longer.  I asked if she thought she’d see him again.  She told me they had already agreed to get together the next weekend.  And, she added, he had agreed to let me fluff him for her because she’d told him she liked watching me suck cock.  She told me she couldn’t wait for me to see his cock and to suck him for her.  As she told me what she had planned for me the next weekend, my penis became erect.  My cheerleader felt it too and reached down to hold me.  “Something tells me you are looking forward to sucking Jason’s cock Sissy.”  I immediately felt embarrassed to have reacted as I had, but the penis doesn’t lie.  Then, without a word, my cheerleader slid me inside of her wet pussy again.  “I guess I’m turned on by the thought too,” she smiled as she began rocking on me, urging me to go slowly.  I had not been inside of her in over a month.  Then, after she fucked Jason, I was inside of her twice in one day.  I was in sissy heaven.  I lasted longer this time and when I finally came, my cheerleader had an orgasm too.  I cleaned her out and then we got up to shower and prepare dinner.  The rest of that weekend was special, just the two of us, although it was obvious my cheerleader was in a really good mood because of Jason.  But I wasn’t going to look a gift horse in the mouth – she kept me out of chastity the entire weekend.  I couldn’t decide if things had suddenly gotten more complicated, or just different.  I had no idea how she planned to work two men into her sex life.  But she would.  In the next post, I’ll tell about the next weekend with Jason.