Tuesday, January 14, 2014

Cheerleader Is A Happy Girl

[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 ApartOur 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. These are the previous posts that tell the story about my sissy journey.]
My cheerleader locked me back into chastity on the Sunday evening following her rendezvous with Jason, the man she picked up at our neighborhood’s annual holiday party.  We had spent an amazing weekend together following her night with him, making it, in my mind, very worthwhile.  I loved seeing my cheerleader so ebullient and happy, even if I was merely an indirect cause of her joy.  And while I was disappointed to be going back into chastity, I had been expecting it, so I wasn’t surprised.
My cheerleader had made plans with Jason to visit us the following weekend, on Saturday, and my cheerleader was positively floating on air as she anticipated her next tryst with him.  He was going to come by Saturday afternoon and watch the college basketball games that were scheduled for that day, and maybe stay through Sunday to watch the last week of the NFL season.  My cheerleader confided in me how excited she was to have added another man to her list, albeit a two-man list at this point.  For her, it appeared to me, Jason was symbolic of her taking control over her sex life because she had set out to find a man she found desirable and had accomplished her goal.  I sensed that she realized then that she could find men when she felt a desire to do so, and I even wondered whether that meant it was more likely that she would eventually bring other men into her fold.
During the week leading up to the weekend, my cheerleader was especially attentive and affectionate with me.  She teased me quite a bit about the weekend, including her intention that I fluff Jason for her.  She repeatedly told me that she could not wait to see me with his cock in my mouth and urged me to make sure he enjoyed it so that he would feel good about letting a sissy suck his cock.  When my cheerleader spoke that way to me, I always felt embarrassed, but at the same time, I found it quite arousing.  I felt nervous and anxious about the weekend, but I also felt excited as I anticipated being on my knees again, sucking a cock for my cheerleader.  She had told me he was big, but I was looking forward to finding out for myself.
My cheerleader had told me her plan for how the weekend would proceed.  I was going to spend the weekend as her sissy maid, dressed appropriately, of course.  Thus, my only job was to serve her and Jason as they spent the weekend together.  She would let me know when, where and how I would serve them.  All I needed to do was to behave as her sissy servant husband, and to follow her lead.  She did not say whether she had briefed Jason on what to expect, other than letting me know that she had asked him if he was willing to let me fluff him for her, and that he had consented to that much.
On Thursday evening of the week leading up to the weekend visit by Jason, my cheerleader received a phone call while we were watching television.  Want to guess who it was?  If you guessed Randall, then you guessed correctly.  My cheerleader had not mentioned Randall the entire week.  I had privately been wondering what might become of him, now that my cheerleader had hooked up with Jason.  Had she told him about Jason?  Did she intend to?  I wondered.  As I listened to her side of the conversation she had with Randall that evening, it became clear to me that she had not shared the news about her new man with him.  Randall was calling to make plans for the weekend with my cheerleader, having not seen her the previous weekend for the first time in quite a while.  From her side of the conversation I could tell that she was uncomfortable as she responded to his inquiry about her plans.  She told him that she and I had already made plans for Saturday and Sunday, but that she was free Friday evening.  As you might imagine, hearing her say that created an immediate spike in anxiety for me as I realized what she was proposing to Randall.  And when his response confirmed my fear - the weekend I thought we had planned suddenly became a weekend I had not anticipated.  Randall was going to spend Friday night with us and then, the next day, another man was going to be treated to a special weekend with my cheerleader. 
As she hung up from her call with Randall my cheerleader immediately looked at me to see how I was taking the sudden modification of our weekend plans.  “You haven’t told Randall.  Have you?” I asked her.  She admitted that she had not, and then questioned whether she needed to.  Her reasoning to me then was that these were simply men she had sex with.  Why did either of them have to be aware that they were not the only one?  I couldn’t think of a good response for her at the time.  I mean, she had a point.  She was a married woman and each man knew that she was.  They also each knew the story with us – that I was a sissy and that she had my consent to fuck them.  What more did they need to know?  The problem, as I saw it, was the additional drain upon my alone time with my cheerleader if the addition of another man meant that she would be doubling up on our weekends.  However, that was not a discussion we were going to have at the time.  All that mattered then was that my cheerleader was suddenly going to entertain – which meant that I was going to entertain – two men in our home that weekend.  And guess who was already excited about what that meant?  Uh huh.  My cheerleader.
Realizing that Randall would be visiting in less than 24 hours, she told me she needed me to help her begin to prepare for him right then.  She wanted me to do her nails and to help her groom for Randall.  So we stopped watching our television program and went upstairs to begin preparing, one day earlier than I’d anticipated, for the weekend.  While I attended to her, my cheerleader reviewed what she would expect from me during Randall’s visit.  As excited as she seemed about what visits by two different men meant to her, she appeared to be equally excited about what it meant to me.  She teased me, asking if I ever imagined I would be treated to sucking two different cocks in one weekend.  Embarrassed, I admitted that I had not considered such a thing.  But it appeared to be my destiny for the upcoming weekend.  As you might guess at this point in my narrative, the upcoming weekend was building up to being a big event that would hold a special place in the history of our marriage.
By now, those who have been following my story about my sissy journey have probably concluded that this story is not just about me – it is also about my cheerleader.  Readers might also already be anticipating the types of things I will be describing regarding how I spent the weekend when my cheerleader invited two different men to our home.  I assure you, I am going to describe the weekend in the sort of detail readers of my blog have become accustomed to receiving from me.  What can I say?  I am a detail-oriented person by nature.  However, what I want to emphasize here is that this particular weekend, much more in my mind, was less about me, and more about my cheerleader.  Sure, my cheerleader had come a very far distance emotionally and sexually from the beginning of our marriage to the moment I am now telling about.  She had accepted so much about me that she never could have anticipated having to process, much less accept, when she married me.  But she was also discovering things about herself along the way.  It seems to me that this particular weekend was a major turning point for her where she and I, and she and other men, were concerned.  If there had ever been a question as to which of the two of us was leading the parade, so to speak, since I was the one who had initially nudged us in this direction, the answer to the question appeared to me to be resolved as this weekend unfolded.  And I think you’ll see what I mean as I reveal the details.
I left work early on Friday afternoon to get home in time to prepare for Randall.  My cheerleader was off that day and she had done quite a bit as well, obviously getting ready for both Jason and Randall.  I sensed that she was fine with Randall visiting us, but that she was especially excited about Jason’s visit, and that he was her main event so to speak.  Whether that was because he was new, or because of how she had managed to select him and bring him into our lives, I couldn’t say.  It just seemed to me that she wanted her weekend with Jason to be special.
My cheerleader told me to wear my black maid’s dress for Randall, as she wanted me in pink for Jason.  I dressed in all black lingerie, including a garter belt to hold up my stockings.  I wore black panties covered entirely in white lace, front and back, which looked especially sissy.  My nails were painted red and I was told to wear the blonde pageboy wig that Andrea had bought for me when she was “breaking me in.”  My cheerleader was dressed in a short, black mini-skirt and tight red pullover top.  She also wore black stockings held up by a garter belt, the tabs of which showed beneath the hemline of her short skirt.
My cheerleader had prepared a nice dinner for her and Randall to enjoy alone together.  My role was to be her servant.  When Randall arrived, I greeted him at our front door with a curtsy and led him to my cheerleader who was waiting for him in the den.  She stood as he approached her and gave him a long, sensuous kiss, rubbing his cock through his trousers as she did.  Acting in accord with her greeting, Randall let his hand roam under her skirt, grabbing her ass as he pulled her tightly to him.  When my cheerleader finally broke her kiss, she smiled sexily at Randall and said, “It seems you are as happy to see me as I am you.  Should we just go fuck now?”  I was stunned at her bluntness.  I know that might seem odd, considering how far we had come, but such language from my cheerleader was still not what I was used to.  Randall’s response was not surprising.  “Why not?  That’s why I’m here, isn’t it?” he added.  My cheerleader took him by her hand and led him toward our bedroom.  “Keep dinner warm Sissy.  I’ll call you when we’re done so you can clean up.”  I was shocked at her brazenness and could barely form a reply.  I curtsied and said, “Yes ma’am,” as Randall grinned lasciviously at me, a look that basically said, ‘See what you are missing Sissy?  Your wife is a fuck queen!’
My cheerleader was giggling as she led Randall upstairs.  The door to our bedroom slammed as she led him in, leaving me alone within the first few minutes of a man entering our home.  After gathering my wits, I attended to making sure dinner was kept warm, but not overcooked, while I waited for my cheerleader and Randall to fuck.  While it seemed to me that they were upstairs forever, in reality, it was less than an hour before she called on my iPhone and told me to come upstairs.  I went up understanding that I was likely to have a cock in my mouth sooner than I had expected I would.  My cheerleader was lying nearly naked in our bed beside Randall, who was naked.  She wore her garter belt and stockings, but nothing else.  Randall’s spent cock was lying across his thigh, glistening from the wetness of his cum and my cheerleader’s pussy.  As I entered my cheerleader pointed to Randall and told me to clean him first.  I was used to servicing Randall in this manner by this point.  And he was accustomed to me servicing him as well.  I lifted his thick cock to my mouth and began licking and sucking him clean.  I felt him beginning to get hard again as I cleaned their juices off of him.  “Don’t stop Sissy,” my cheerleader said.  “I want to watch him cum in your mouth.”  I felt humiliated in that moment.  My cheerleader had taken to teasing me more and more, it was true, but such teasing as that, especially in front of Randall, was uncharacteristic for her.  Nonetheless, I continued sucking Randall’s cock, letting his thick rod slide back and forth across my wet lips.  I could feel him pulsing as he responded to my mouth.  Meanwhile, my cheerleader was watching me closely, encouraging me to suck him, until the moment when I felt the first jet of semen erupt from Randall’s cock.  He may have just cum inside of my cheerleader, but he had recovered enough to fill my mouth with sperm.  Once he began, he fired blast after blast of his cream inside of my mouth and I swallowed all that he gave me, feeling my own sense of satisfaction from having caused his second orgasm since arriving in our home.  When he was finally spent and clean, I turned my attention to my cheerleader who was lying on her back, her thighs opened and ready for me to clean her pussy.  She encouraged me as I did so, calling me her “sweet Sissy cocksucker.”  I had not anticipated such from her and it was a difficult moment for me.  However, I understood my role by then and accepted her words without reaction, simply continuing to do for her as I knew she expected of me.  When I had completely cleaned her pussy she told me to go get dinner ready to serve – that she and Randall would be down soon.
I began to set their dinner out on the table as I heard them walking down our stairs.  I was surprised to see how my cheerleader was dressed when she came in with Randall, who had changed into a t-shirt and gym shorts, making himself comfortable post coitus.  My cheerleader was wearing a sheer black babydoll nightgown and a pair of red bikini panties – nothing else.  Seeing her so intimately dressed in front of Randall and me threw me for a loop.  Suddenly, I was the most dressed person in the room.  My cheerleader was really putting on a display for Randall, as she treated me like her servant.
They ate alone, while I cleaned up in the kitchen.  When they finished, they went into the den and sat on the couch.  My cheerleader asked me to bring them drinks and then she told me to help her find a movie on Netflix.  She wanted to watch a Romantic Comedy and so I searched that category until she saw a movie, “How To Lose A Guy In 10 Days,” starring Kate Hudson and Matthew McConaughey, that she liked.  She told me to turn out the lights and to give them some privacy.  So, for the next few hours, I waited in the kitchen while my cheerleader and Randall snuggled on our couch watching a movie.  Around midnight, she and Randall came into the kitchen, heading for bed.  She told me I could go to bed and to be prepared to bring them breakfast in the morning.  I admit that I was disappointed that she did not invite me to join them.  Somehow I had it in my mind that I was going to fluff Randall for her.  But that was not to be. 
After cleaning up I went up to our guest room, changed out of my uniform, put on a nightie, and went to bed, filled with an odd sense of anxiety.  It wasn’t that I was upset that my cheerleader was with Randall.  I accepted that.  I simply felt odd at the way the evening had gone.  Was my cheerleader making a point to me?  That I needed to know my place?  Or was something else going on?  I couldn’t quite figure it out.  But it did occupy my mind and so I had difficulty sleeping.  Around 8 a.m. I woke up and got dressed to serve my cheerleader and Randall breakfast.  As I walked past their closed door I heard my cheerleader cry out – the sound she makes when she is experiencing intense sexual pleasure.  I paused, almost involuntarily, to listen, and heard her through our door telling Randall she loved his cock and to fuck her harder.  My penis swelled inside of its chastity cage as I heard her being fucked by Randall.  Worried that she might hear me eavesdropping on them, I stepped out of my heels, picked them up, and tiptoed down the stairs to the kitchen to prepare coffee and pastries.  When everything was ready, I returned and knocked on the door.  My cheerleader told me to come in.  I was prepared to find them naked in our bed.  I was not wrong.  She was lying next to Randall, her bare breasts pressed against his shoulder, as she fondled his spent cock right in front of me.  I served them coffee and pastries and then excused myself.  She didn’t even invite me to clean them.  Again, I was oddly disappointed.  I felt left out.  I didn’t like that feeling.  I was comfortable with my cheerleader having her man.  But I liked that I usually participated in some way, even such as I did.  I suppose that may sound odd to some – a man wishing that his wife would permit him the role of cleaning up after she and her lovers fucked.  But it was how I felt. 
I had not been downstairs long when Randall came down, dressed to leave.  He thanked me for everything as he left.  I went upstairs to find my cheerleader still in bed, and still naked.  She smiled at me as if everything was normal, and I must have somehow given away how I was feeling.  She asked me what was wrong.  I tried to pass it off as nothing, feeling as though there was nothing to say really.  But my cheerleader knows me well and she insisted that I tell her what was wrong.  When I did, she said she was sorry.  She hadn’t meant anything by it.  She told me that she was trying to give me what she thought I wanted by treating me more like her sissy maid than her sissy husband when men were around.  I told her I understood, but that I’d been a bit confused because it seemed so different than other times when Randall was around.  She then asked how I was feeling about the rest of the weekend, with Jason coming and all.  I told her I was prepared to do as she wished, but would just like to know what to expect.  That’s when she told me that things would be a little different with Jason because she was still getting to know him, but that she fully intended for me to participate with them some, because she wanted him to understand that I was on board with everything.
With the air cleared between us, she had me clean her pussy after her morning fuck with Randall.  Afterward, we each showered and began getting ready for Jason’s arrival.  My cheerleader’s demeanor actually noticeably changed.  She was much more excited about the rest of the weekend with Jason.  I touched up her pussy with a fresh shave, as she wanted to be perfectly smooth for him.  We also trimmed me up a bit as well.  I wore my pink maid’s dress, with a black petticoat.  I wore a pink bra, garter belt, black stockings, and sheer pink panties with black lace across the bottom, but with my chastity cage visible through the front of my panties.  She wanted Jason to be able to see that I was locked in chastity, explaining that she thought that would confirm to him that her pussy was off limits to me.  I knew that displaying myself in that manner was going to be humiliating for me, but accepted that my cheerleader wanted it that way.  My cheerleader was, well, she looked beautiful.  She wore a light blue lingerie set consisting of a shelf bra that left her nipples exposed, a matching garter belt and sheer bikini panties worn outside of her garter belt.  The dress she had purchased the day before was so sexy – it was also light blue, and the top, held up with spaghetti straps, fit her snugly which emphasized her exposed nipples, and the skirt was flirty and short, revealing her black nylon covered legs.  I remember thinking that poor Jason would have a difficult time concentrating on the games with her dressed as she was.  She asked me if I thought Jason would like her dress, and I just looked at her like, ‘Are you kidding?’ which made her smile.
We worked together downstairs preparing snacks and things for them to eat while watching basketball.  She explained to me that, once Jason arrived, she wanted me to tend to them, but to carry on with house cleaning as though it were my Saturday job  - changing the sheets on our bed and doing our laundry.  She wanted Jason to see her sissy husband in action.  However, I was to constantly check in with her to see if they needed anything.  When the doorbell rang, she told me to go greet Jason and to welcome him.  I don’t think he was expecting to find me wearing a wig and looking so completely feminine when I greeted him.  As I curtsied for him and invited him in, he did a double take as he visually took me in.  I welcomed him and told him my cheerleader was in the kitchen waiting for him.  I took his overnight bag and carried it upstairs to our bedroom.
When I came back downstairs I entered the kitchen to find my cheerleader standing close to Jason, her arms around his neck, kissing him.  I hesitated at the entrance as she continued kissing him, noticing his hand resting on her bare shoulders.  When she stopped kissing him, she acknowledged me, saying, “Hi sweetie.  Would you mind bringing Jason and me some snacks and a drink into the den?  We’re going to settle in for the games.”  Jason watched my response, clearly unsure of how to behave on a date with a woman who had a sissy husband (like, who would?) as I said, “Yes ma’am.”  She led him behind her into the den.  When I carried the snacks in, I asked what they wanted to drink and then went to prepare them.  After I served them my cheerleader said, “Once you’ve changed the beds and finished the laundry, if you’d like, you can join us to watch the games.  Okay?”  She was being so sweet to me in front of Jason.  I curtsied and said, “Yes ma’am.  Thank you.”  I then went to take care of my chores.  Honestly, at the moment, I didn’t know how I felt about returning to sit with them while they watched the games.  My cheerleader looked so sexy and I was dressed so sissily, that I wondered if it would be uncomfortable.
Nonetheless, I went about my chores.  I began with changing the sheets on our bed for my cheerleader and Jason to sleep in later.  Then, I gathered our dirty lingerie and other laundry that had accumulated over the past week and went to the laundry room to wash everything.  While I was hand washing our panties, my cheerleader came in to check on me.  She came up behind me and put her arms around me, kissing me on my neck as I worked.  “How are you doing sweetie?” she asked.  “I’m fine,” I told her.  “And you?”  She giggled and said, “Just great!  I wanted to check on you.  And to tell you that I love you.  Thank you for giving me this baby.  I really do appreciate it.”  She reached in front of me, lifted my skirt and, touching me outside of my panties, cupped my balls under the chastity cage.  “I plan to reward you for this sweetie.”  I couldn’t think of a response at the moment.  I just knew that she had done more for my psyche than she likely realized by coming in to check on me.  “Thank you,” was my response.  As she left she said, “I really want you to come join us when you’re through.  I want Jason to get comfortable with you.”
I want to take a brief detour from my story right here.  I have read so many different accounts of men such as myself who are in relationships of varying kinds with women who, for want of a better word, dominate the relationship.  Wife led marriages, Mistresses, Dominatrixes, whatever the term that may be used.  In many instances, the woman is quite strict and can sometimes even come off as sounding downright mean to her submissive man.  I have come to conclude that there are so many variations and circumstances that exist as backdrops to the many degrees and forms such woman controlled relationships may take that there is simply no way to make judgments as to what is “good” and what is “bad” behavior.  To me there seems to be simply, what is.  The couples are where they are and, so long as each is contented in some way, who am I to judge?  But, having said that, I want to say here how lucky I considered myself as I went through all that led to the present (and still do) to have a wife who was so tender and loving and understanding to me throughout.  I love her so much and would do anything for her.  She knows it too.  But as we move forward with me telling my story, I just wanted my readers to understand just how strongly I felt for her and how much I appreciated how she treated me.
After I completed the laundry and made sure that everything else was straightened up throughout our house, I organized things in the kitchen for dinner between games.  Then, as nervous as I could be, I went to the den to join my cheerleader and Jason.  Before sitting down, I asked if they wanted fresh drinks.  They did, and my cheerleader told me to pour myself a glass of white wine.  When I delivered their drinks, Jason thanked me for his, clearly stumbling on how to refer to me.  My cheerleader interrupted him and instructed him, “Call her Sissy Jason.  That’s what I call her.”  He looked at me, obviously uncomfortable, and said, “Thank you Sissy.”  I curtsied, smiled, and replied, “You’re welcome sir.”  It was funny really.  This man was so polite, and yet, so confused as to how to treat me, that it was almost as though I had the upper hand on him, despite that he was holding my wife in his arms as I served them.  Weird, huh? 
I sat on a sofa opposite them and we watched the game together.  Notwithstanding my sissy attire, I was still a man underneath when it came to watching and enjoying sports.  I found myself, as did they, relaxing as we watched the game together.  It turned out that Jason and I were pulling for the same team, and we began sharing views about the teams and the game.  I recall, at one point, catching my cheerleader watching me and smiling as her man and I slowly became more comfortable with each other.  Toward the end of the first game, my cheerleader excused herself and asked me to join her in the kitchen.  When we got there she pulled me to her and gave me a deep and passionate kiss.  When we broke I asked what that was for and she said, “Because you are the best sissy husband in the world!  That’s why!”  Then she returned to Jason, telling me to get dinner ready.  We were going to have pizza in the den together.  So, I was feeling pretty good at that point.  Jason was very nice and treated me courteously.  My cheerleader was very happy – with me and otherwise.  All in all, I had no complaints.
We ate dinner together, shared drinks, and watched the second game.  When the game was over, my cheerleader stood and asked Jason to excuse us for a few minutes, beckoning me to follow her out of the den.  She led me upstairs to our bedroom where she began to undress.  As she did so, she explained to me her plan.  She was going to dress for bed, and then, I was to go downstairs and invite Jason upstairs to join her.  Once I had him there, and he saw her, I was to ask him if I could please prepare him for my wife.  She assured me that he would go along.  I don’t know that I can possibly, adequately explain just how anxious, nervous, scared, and simply lost I felt in that moment.  I had become so comfortable with the two of them over the last several hours, almost as though we were not engaging in cuckoldry foreplay, that I didn’t permit myself to remember what the ultimate purpose of the evening was – namely, for me to suck Jason’s cock and for him to fuck my cheerleader.  Now that it was upon me, I was a wreck.
My cheerleader had bought a brand new sexy nightgown for the occasion.  It was a light blue sheer nylon gown, invoking a virginal quality, which allowed her light blue garter to show beneath it.  And that is all that she wore beneath her gown, as she took off her bra and panties.  She climbed onto our bed and lay there, on top of the covers, waiting for her man to be delivered to her by her sissy husband.  As nervous and scared as I felt, it was equally obvious to me that she was energized about what was about to occur and was at her peak of sexual readiness.  Before I left to deliver Jason to her, my cheerleader motioned me to her and kissed me softly on my lips, then said the last words she would speak to me until after Jason fucked her – “I want you to suck his cock like you’ve never done before Sissy.”  I looked into her loving eyes and said, “Yes ma’am,” then left to bring Jason to her.
Jason was sitting on our couch, in our den, waiting uncomfortably for what I realized he suspected was about to occur.  As I appeared before him, I curtsied, and said, “Would you please come with me Mr. Johnson?”  As if I was the one in charge, rather than him, he obeyed and stood to follow me.  In truth, neither of us was in charge.  My cheerleader was in charge.  She held the power over each of us.  The woman among us possessed all of the power.  Jason wanted her desperately.  I wanted her desperately.  And each of us would receive her, but in our own special way, and on her terms.  I did not think those thoughts as this event was unfolding.  But, reflecting upon what took place that night, that is precisely what was going on.
When I opened the door to our bedroom and revealed my cheerleader to him, Jason froze, unable to take his eyes off of her.  Even with her husband standing next to him, his attention became locked upon my beautiful cheerleader who waited for him on our bed.  For her part, she smiled at him, her eyes telling him she would soon be his again.  But not yet.  She was waiting for the show.  Yes.  Jason and I were going to give her a show.  Only, Jason was only a bit player in the show.  I was the star.
I reached out to take his hand and curtsied as I asked, “May I help you get undressed Mr. Johnson?”  Jason looked at me, unsure how he was to respond, and clearly thankful that the sissy between the two of us was taking the lead.  “Okay,” he said quietly.  “Thank you sir,” I told him.  Aware of the intense gaze of my cheerleader upon me, I began slowly and carefully unbuttoning his shirt, and then helped him remove it.  I then carefully folded in half and laid it across a nearby chair.  He was a very well built man, with a muscular chest and shoulder.  It was obvious that he worked out.  Then, I stooped to the floor to help him remove his shoes, and then his socks.  Looking upward, making sure to secure eye contact with him, I went to my knees and began the last fateful act of revealing his manhood to my cheerleader and to me.  I unbuckled his belt and then unfastened his trousers.  My fingers trembling with excitement and fear, I lowered his zipper and then lowered his pants to the floor in a puddle at his feet and helped him step out of them.  I held them before me, folded them along the crease, and laid them next to his shirt on the chair.  Now, only his boxer shorts – a real man’s underwear – stood between my face and his cock.  I tugged them downward.  If Jason had hoped to pretend that having a sissy undress him in this manner did not excite him, the release of his cock from his underwear betrayed him.  As Randall had months before when I did the same thing to him, Jason’s cock sprang upward and outward the moment it cleared his boxers.  My cheerleader actually gasped from her perch on our bed as I softly and deftly grabbed it in my feminine fist.
My hands trembling – with equal measures of fear and excitement – I softly stroked Jason’s cock with my fingernails, all while looking upward into his eyes.  I could sense that he was as nervous and excited as I was.  Nowhere in his mind could he have imagined that one day he would have another man, dressed as a feminine creature, kneeling before him and worshiping his cock, all for the sole purpose of delivering him to a woman to make love to.  And yet, it was happening and he seemed to be willing to go along for the ride.
As my cheerleader watched from our bed, I licked the length of Jason’s cock from the underside.  I could feel his heat and blood coursing through him.  As I reached the tip, I took him between my lipstick-covered lips and swirled my tongue softly around the ridge of his cockhead.  I licked all of the way back down to the base and then opened my mouth wide, sucking his balls inside of my mouth, tenderly sucking them for a long time.  Jason’s response suggested to me that he had never had his balls treated in such a manner.  Although I knew that my cheerleader was watching me suck her lover’s cock, at this moment it had become just me and Jason’s cock.  I did enjoy sucking cock.  Sometimes, I wonder what others think when they hear a man talking about sucking another man’s dick.  But I love having my mouth filled with a living, breathing, pulsing cock.  The power of an alpha man using your feminine sissy mouth for his pleasure is an incredibly erotic rush and I love it, even though I often find it embarrassing to admit that I love it.  If that sounds conflicting, then I don’t know what to say.  But the other thing I love is that it is something I do that my cheerleader loves seeing me do.  Performing that act for her is a very real turn-on, not just for her, but for me as well.
I continued a slow and sensuous worshipping of Jason’s cock, licking his shaft, sucking and kissing him all over, until I began to take him into my mouth in earnest.  He was much too long for me to take all of him.  And although he was very thick, I did not have difficulty getting my mouth around him.  Careful to allow only my lips and wet tongue make contact with his soft cock membrane, I gave Jason a very wet, very hot blowjob.  He was hard when I began, but he was growing harder and larger as I sucked him.  I felt a rush of excitement as I thought of how my cheerleader would respond when Jason slipped inside of her after I finished with him, which I knew would be soon.  Initially, I was doing all of the work, Jason seemingly satisfied to stand still while a sissy sucked his cock.  But when I felt him move forward for the first time as I lowered my mouth down his shaft, thrusting toward me so as to drive deeper inside of me, I knew that he was lost in the act and no longer felt unsure about what we were doing.  That thrust hit the back of my throat and I gagged a bit and my eyes teared up some.  I held him off of me with my hands after that, and it was not much longer that my cheerleader told me to stop and told Jason to come to her.
Leaving me on my knees beside our bed, Jason climbed onto our bed and into my cheerleader’s eager arms.  As she pulled him to her and kissed him passionately, I stood and prepared to leave them, unsure what else I should do.  But my cheerleader stopped me and told me to stay.  Thus, I stood there, by our bed, watching as my cheerleader threw herself at the man whose cock I had been sucking only moments before.  I was going to be permitted to watch as he fucked my wife.  Jason let himself go as my cheerleader revealed her urgent need for him.
I want to emphasize something as I describe what I observed that night about one year ago.  I had no idea precisely what my cheerleader was thinking or feeling.  I only knew what I saw her doing – how I saw her reacting to another man – and how she was behaving knowing that her husband was standing directly beside the bed watching her give herself to another man.  And as for me, I am not even confident that I’m accurately relating what I was thinking and feeling in the moment.  I’m trying now, over a year later, to tell about it to the best of my ability as I, in effect, re-live the moment.  What I do remember is the sense of helplessness I felt as I watched my cheerleader lose herself in the act of sex with a man who had a very large cock and who was touching her in places that I had never touched.
My cheerleader eventually pulled her sexy nightgown over her head and tossed it toward me.  I stooped as it fell to the floor and picked it up, dropping it on top of Jason’s clothing on the chair by our bed.  My cheerleader was naked then, save for her garter belt and stockings.  Jason was entirely nude, leaning over her, his hard cock lying on top of her sexy, nude belly.  Raising her legs high, readying herself for penetration, she said to Jason, “Fuck me!  Please!  Fuck me now!”  Jason raised up and positioned the thick head of his shaft against my cheerleader’s slit, wet and ready for coupling.  He began to press downward, my cheerleader sighing as he spread her lips and slipped inside, first the head, and then a bit at a time, the rest of his long, thick cock, sliding deeper and deeper within her.  I recall feeling a sense of awe that he was able to continue to penetrate her with his long cock.  How could she take all of him?!  With each level of insertion inside of her, my cheerleader breathed in short gaspy breaths, not showing signs of pain, but rather, signaling her utter and indescribable pleasure.  Jason sank his cock up to the hilt inside of her and paused, the two of them looking hungrily into each other’s eyes.  “Fuck me!” my cheerleader encouraged him.  “Fuck me Jason!”
Jason began to pull back.  I was transfixed as I watched his now slick, wet cock, covered with my cheerleader’s pussy juices, withdraw from her pussy lips.  He withdrew until only the tip remained within her, her lips hugging his cock head at the entrance to her pussy, and then sank down inside of her again.  Jason was deliberate with his opening strokes.  He took his time with each penetration and subsequent withdrawal.  My cheerleader was moaning her urgency.  She seemed to both want him to continue tormenting her by taking it slowly and, at the same time, to begin fucking her harder.  But she allowed him to control the pace, her female response made known with a combination of sighs, moans, and utterances of approval – “Yes!  Oh!  Yes!  Uh!  Mm!”  At a certain point it did hit me that neither of them were paying any attention to my presence.  I was reduced to a voyeur, granted a front row seat to observe my cheerleader receive one of the best fucks she had ever received.
I lost track of the time.  I remember thinking that I never lasted as long as Jason lasted.  I would have cum within minutes of being inside of my cheerleader.  But Jason had staying power.  Still, eventually, he was no longer taking his time.  He began fucking my wife.  And when I say he was fucking her – I mean he was fucking her.  He was pounding her pussy with each thrust.  The wetness generated between the two of them made the slap at the point where his groin hit hers at full insertion report loudly.  My cheerleader’s sighs and moans became cries and near screams.  She repeatedly cried out, “Yes!  Yes!  Yes!” as Jason caused multiple orgasms, her face contorted in erotic satisfaction.  Was any part of it caused by her knowing that her sissy husband was witnessing, first hand, the joy she was receiving from another man with his consent?  I did not know.  I doubt it.  I only knew that I had never seen my cheerleader so lost in sex before.
Suddenly, the next thing I knew, Jason had driven deep within my cheerleader and stopped.  He grunted loudly and my cheerleader responded, “Aaaaahhhhh yes!”  And I knew.  He was filling her.  Jason was filling my cheerleader with his sperm.  He began pumping and pumping against her, not withdrawing – only pumping – as he emptied his load of cum within my cheerleader’s womb.  And my thought?  Would I be asked to clean her?  Is that why she asked me to wait?  Jason collapsed on top of my cheerleader who had wrapped her stocking covered legs around his waist and held him tightly to her bosom with her arms around his back, and she began laughing as she reveled in the final moment of their coupling.  “Fuck!” she cried out.  “Fuck!  That felt soooo good!”  She then kissed him hard on his mouth as she showed her gratitude to the man for fulfilling her womanly need.
I recall feeling uncomfortable watching them, two people who had just shared such an erotic and sensuous act of love with each other.  Should I leave them to their privacy?  Then, my cheerleader looked at me and smiled.  “Thank you sweetie.  Thank you!”  She then rolled Jason over to her side and let his cock slip out of her pussy.  I watched as his wet cock flopped out, covered with his cum and her juices.  She pushed him onto his back and then said to me, “Clean him Sissy.”  Just like that.  I was back involved.  No longer the voyeur.  I was back on duty.  My cheerleader’s cuckold, doing his job.  And so I leaned over Jason and lifted his spent cock with my fingers, the sticky coating of his cock covering my fingers, and lifted him to my mouth and began licking and sucking him clean.  As I did a load of his cum oozed from his cockhead and I swallowed his thick milky cream.  When I finished with him my cheerleader pointed to her pussy as she lay with her thighs spread wide, ready for me to prove again my submission to her pleasure by sucking another man’s sperm out of her pussy.
My cheerleader held my head firmly against her slick, wet opening, coaxing Jason’s semen out of her and inside of my mouth, pressing her pussy upward as my tongue penetrated her and teased her clitoris, bringing her to yet more orgasms.  As she had when Jason first began fucking her, she sighed her satisfaction, urging me on saying, “Yes Sissy!  Yes!” as if she wanted to make sure Jason understood that he was the man and I was the sissy, as if it was not obvious.  Finally satisfied, my cheerleader released me and then said thank you again.  Then, dismissively, she told me I could go to bed, reminding me to bring them breakfast in bed.  I said, “Yes ma’am,” and curtsied.  As I turned to leave Jason said, “Goodnight Sissy,” and I replied, “Goodnight sir.”
I closed the door to our bedroom, leaving my cheerleader alone with the second man with whom she had cucked me.  Thinking back on it, it was the most erotic moment my cheerleader and I had ever shared.  Even comparing it to the first time she cucked me, with Randall, this time was different.  My cheerleader had put me on notice on this evening that she was a sexual woman who loved surrendering to the act of being fucked – and that she was completely comfortable doing so while I stood by as an observer.  I went alone to our guest room, took off my clothes, and then took a shower.  The warm water felt great as I washed the sex off of my face.  I then put on a nightgown and went to bed alone, certain that my cheerleader and Jason were probably making love again, but in a more intimate way than what I’d just observed.  I had done my part tonight – I had not simply told Jason he had my consent to fuck my wife – I had shown him that I wanted him to fuck her and also proved to him that she and I each needed him to fuck her.
That shift in understanding for Jason was evident in the morning when I served them breakfast in bed.  My cheerleader was wearing her sexy gown when I entered our bedroom with a tray of coffee and pastries.  She was snuggled closely to Jason when I entered.  They each greeted me, “Good morning Sissy.”  I curtsied and returned their greeting.  “Did you sleep well Sissy?” Jason asked me, his politeness shining through.  “Yes sir,” I answered.  I then served them coffee and pastries.  My cheerleader watched me serving them as she visibly cuddled with Jason, showing her womanly attention to him.  Jason complimented me on the breakfast and thanked me repeatedly for my service.  He seemed to completely accept me in my role as my cheerleader’s sissy husband.  I think he liked me.  In fact, I know he did.  Jason seemed to have grasped and seen clearly the unique relationship my cheerleader and I had with each other – that we were in love and that my ability to submit to her needs as I did was, indeed, an act of love.  I had no idea what sort of conversations the two of them had while they were alone, but I suspect that they had shared their own private discussion about the night before.
After serving them breakfast, I excused myself and went downstairs to wait for them to come down.  I understood that Jason was not leaving right away that day, so I knew that my sissy duties were not yet complete.  I had coffee and a pastry as I waited.  I supposed that they must have been making love again, as they did not come down for a few more hours.  When they did come down, I was surprised to see that my cheerleader was wearing her nightgown.  She was no longer wearing her garter belt and stockings, and her hair was wet.  She was wearing panties beneath her gown, and Jason was dressed casually as well.  As his hair was also wet, I assumed they had showered, likely together.  They greeted me and said they were going into the den.  My cheerleader asked me to bring them more coffee.  After I served them, she asked me to go upstairs and to make the bed and straighten up, and that I could then join them to watch the NFL games that day.
And so the day went.  I served them as my cheerleader’s sissy husband.  We watched the games together.  All in all, it was a pleasant afternoon.  After the games Jason excused himself to leave, but my cheerleader coaxed him to stay longer and took him back upstairs for one last fuck.  I waited downstairs until they finished.  When he came down, he was very nice, thanking me for a wonderful weekend.  It probably should have felt strange to me for him to say such a thing, but I really did like Jason and the way he treated me.  I told him he was welcome and that I looked forward to seeing him again, which I was certain would happen.  After he left I went upstairs to find my cheerleader in our bed naked.  She smiled at me and told me to join her.  I took off my maid’s uniform and crawled in beside her.  She cuddled to me and kissed me, telling me how much she loved me.  Eventually I was between her thighs cleaning Jason’s last load of sperm out of her pussy.
I had been hopeful that, like the previous weekend, my cheerleader would release me from chastity after Jason left, but that did not occur.  Instead, my cheerleader wanted me to take her out to dinner.  So we each took showers, got dressed, and went out to eat.  While at dinner, my cheerleader was so happy about the weekend.  She seemed anxious to discuss the details with me over dinner.  She told me repeatedly how much she appreciated what we had, asking me to confirm for her that I was also happy.  I was happy, and yet obviously for different reasons than her.  For her, it was the freedom to enjoy sex in a guilt free situation, in addition to seeing me perform for her as I willingly did.  For me, it was so much more about pleasing her.  More and more I felt myself falling into a feeling of submission to my cheerleader.  I loved her more and more, if that was even possible, as I was permitted to become more and more feminine.
When we got home from dinner we went to bed together where she let me know that she was in the mood for worship – me worshipping her that is.  She laid back while I massaged her all over, leading to kissing and sucking her tits and then to pleasuring her pussy for a long time with my mouth.  I ached inside of my chastity cage as I had most of the weekend and finally, in a moment of weakness, did the thing I know I am not supposed to do, and begged her to release me.  Almost as soon as I had uttered the plea I regretted having done so, but was surprised when my cheerleader smiled at me and said, “I suppose you have earned it Sissy.  Haven’t you?”  She reached behind her neck, unclasped her necklace, and then unlocked my cage, releasing my penis.  The next thing she did surprised me even more as she kneeled down and took me inside of her mouth and softly sucked me, helping me grow even larger.  I was in sissy heaven again.  Twice in two weeks my cheerleader was giving me the pleasure of being freed from chastity.  I thought, ‘Thank you Jason!’ crediting his presence in my cheerleader’s sex life as the cause for her generosity.  I was excited and apprehensive about being permitted entry inside of her when she sat back onto her haunches and lifted my legs onto her shoulders and raised me upward.  She was grinning lasciviously into my eyes as she did so and it was then that it hit me what was about to occur.  Just as she had done to me so long ago in our journey, my cheerleader raised my body upward until my penis was directly above my face and then she began to masturbate me, forcing me to climax almost against my will while she aimed my cum onto my face and inside of my mouth, an erotically humiliating way for a man to achieve orgasm, but a way that turned my cheerleader on so, so much.  Then, after I was spent, she used her fingers to wipe off the excess from my face and feed it to me, following which she kissed me deeply and then told me she loved me more than ever.  We fell asleep in each other’s arms, an incredible weekend finally ended.  When we awoke the next morning, before I dressed for work, she replaced my chastity cage, where it remained for the next month before being removed again.
The next few months with Jason proved to be very intense.  Much more so than I was with Randall and my cheerleader, I was a part of their lovemaking.  Jason treated me so nicely – not so much as a woman – but as a feminine creature.  We became quite comfortable with each other during his visits to our home.  Indeed, this weekend had marked a significant moment in our marriage – and in a good way.  I realized that there would likely be no turning back with her cucking me.  She had tasted sex with men and loved it.  And she had also accepted me as a sissy, including how it actually benefitted her.  And for me, I understood that what I’d started so long ago when I first confessed my feminine nature to my cheerleader, was now a part of our life.  I would continue to experience sensations of shame, embarrassment and humiliation from events and moments, but I also experienced satisfaction and comfort from being able to so freely be the feminine person that had lurked within my soul my entire life.  I knew I was lucky and unique to have a wife who so lovingly accepted me as the sissy I was.  Even more so was I lucky that she found joy because of my sissy nature. 
I have nearly reported every significant event in my sissy journey up to the present.  There are a few more things to tell about that go beyond the day-to-day events.  I thank everyone who has expressed support of my lifestyle as I’ve told my story.  Honestly, I never thought my personal story would be so well received.  I began this blog as a mechanism to share my story because I felt a need to do so, even as anonymously as I am by doing so in the manner that I have been.  It feels good to publicly tell my story, even if no one actually knows my true identity.
 Until next time, big sissy kisses to everyone,



  1. What a wonderful weekend, and beautifully told.

    You are truly amazing and inspirational couple.

    Love Tanya xxxx

    1. Dear Tanya,

      Thank you for your comment. I feel so fortunate to have the wife I do who accepts me as I am.



  2. Leeanne,

    I get a lot of pleasure from reading your life's story. It's intriguing, erotic, and so incredibly passionate. This portion in particular, however, surprised me. While it may be the most enticing and erotic, I firmly believe that it's also the most loving. Yes, having you participate with Jason was a joy to read, but the big tentpole moment for me was seeing you and your cheerleader grow closer. Seeing her treat you as a sissy maid at first and then correcting her actions and treating you as a sissy husband shows so much that she wants to care for you as much as you want to care for her.

    I love that.

    I don't often appreciate the more emotional side of such tellings, but this truly is making me smile and will make my day better just from reading it. Thank you!


    1. Dear Caitlyn,

      I am so glad to hear that you were able to get that sentiment from this latest entry in my sissy journal. I really felt that her love and caring for me was the thing I most wanted readers to understand.

      There are so many variations of female led relationships, and while I do enjoy reading about the ones where the sissy is treated more harshly, I am so thankful that my cheerleader treats me so kind and lovingly and wanted people to understand that aspect of our relationship. That's not to say I don't get off on the embarrassment and humiliation that I often experience because of some particular situation my cheerleader may place me in. However, she does not do anything with meanness or malice in her heart and for that I am eternally grateful and am pleased that message came through.

      I'm happy if I sent you off to tend to your patients with a smile on your face.



  3. Lovely Leeanne! Just lovely! Your story makes so many things clear about you, your sweet cheerleader and the Sissy Cuckold relationship in general. I thank you for sharing your intimate details and for your asides and insights too!
    Thank your lucky stars that you've found a woman who complements you so well!
    This was the best blog entry I've read since...well since the last chapter of your journey!

    I send you love, kisses and respect!
    I remain your admirer. more so with every post!

    1. Dear Kaaren,

      I do, indeed, thank my lucky stars everyday that my life collided with my cheerleader so long ago, although no one could ever convince me that we were not fated for each other.

      Sweet sissy kisses to you sweet girl,


  4. Leeanne, thank you so much for a wonderful description of the events. I absolutely loved it.



    1. Dear Christine,

      I am so delighted that you have enjoyed reading my personal story.



  5. Dearest Leeanne, Thank you so much for sharing the story of your journey. i have so looked forward to your next chapters you are such a beautifully talented writer.

    i detoured into your fictional writing, "A Fall to Grace", while waiting for your next chapters and cannot help wondering that your personal journey overlapped your fictional writing at some point, yes?

    i wonder if you have experienced any of the emotional trepidation expressed by the fictional Dani, denying his "sissy-ness"?

    Does your Cheerleader now know of your blog and fiction and how does She view your telling of your story.

    many sissy hugs

    lavender sachet

    1. Dear lavender sachet,

      I do admit that, throughout my journey, there have been many moments of "emotional trepidation," such as I have expressed through characters in my fictional stories. No doubt my own sissy nature informs most of what I do, and especially so my writing on the subject.

      My cheerleader does not know about my writings at this time. I have been struggling with telling her for a while now, as I do know that she has expressed concern about my Internet meanderings in the past. She, as many people rightly do, worries about things posted on the Internet. So, whether to tell her about this blog is a dilemma for me. I worry a lot about keeping it secret, almost as much as I worry about how she might react if I tell her. Hmmm. What is a sissy to do?

      Thanks for your comment and for reading my fiction on Fictionmania.

      Kiss kiss,


  6. Oh Sweetie, this posting is so loving and at the same time exciting! I truly don't know how I would react having to bring a new Man up to my wife's bedroom and then fluffing him! I read this post about three times and will probably read it many times again. Thank you so much for sharing your intimate life secrets with us- you are the best!
    Many lipstick kisses and a deep curtsy!

    1. Three times jennifer! Oh my! You deserve some special sissy lipstick kisses and a curtsy as well!! Love you!



  7. Leeanne, thanks again for posting your story. It is truly amazing, and an inspiration to many of us. I think you are the luckiest sissy in the world. I would say however that I'm surprised that it appears your Cheerleader does not use the strap-on with you, and that you have not been taken by a real man yet. It seems to me that your journey has more room for advancement!