Sunday, April 27, 2014

My Cheerleader's Summer Of Contentment

[NOTE - Anyone who is just beginning to read my blog, might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home - Cheerleader Cucks Sissy - Cheerleader and Sissy Are Mentored - Sissy Offers Context For Cheerleader - Sissy Sees Her Future - Sissy Adapts To Chastity - Sissy And Cheerleader Spend A Weekend Apart - Our Weekend Apart Aftermath - Cheerleader Has A Heart-To-Heart With Sissy - Sissy And Cheerleader's Last Weekend With Andrea - Part One - Sissy And Cheerleader's Last Weekend With Andrea - Part Two - Cheerleader Thanks Sissy - Cheerleader Does A Sleepover - How My Cheerleader Vets Men - Cheerleader Flirts - With Purpose - Cheerleader Is A Happy Girl - Cheerleader Learns – Juggling Isn’t Easy - Cheerleader Gets An Itch.  These are the previous posts that tell the story about my sissy journey.]
In my last installment I wrote about what I perceived, at the time, to be another shift in my relationship with my cheerleader.  Randall, the first man she cucked me with, had left Northern Virginia around April of 2013 to accept a new position with the company he and my cheerleader worked for, leaving my cheerleader with only one man in her life, Jason, a man who lived in our neighborhood and was the chief of staff for a United States Senator.  Jason’s visits to our house had increased after Randall moved away, but my cheerleader became a bit, well, antsy, I’d call it.  As it turns out, she needed more - more than one man.  And so, during a Memorial Day party at our next door neighbors’ home, she picked up a new man.  It wasn't so much that she branched out with another man.  It was how she went about it that, to me, was the important thing in so far as how it impacted our marriage.  I had questioned her about the amount of time Jason was spending at our home, and she flatly laid down the law that I was the sissy, that she had accepted me and we weren’t turning back now.  In other words, I had gotten what I asked for - to be her sissy cuck - and she didn’t plan to return to how we were before I suggested she try making love with another man.  Then, on the night she decided to find a new man, she didn’t actually bring it up as a matter for us to discuss.  She simply informed me that she was going to find another man.  Well, when she chose one at our neighbors’ party, she selected a man I had met at their house before, and we had gotten along rather well, but in a guy-to-guy way.  Thus, when she invited him to come to our house after the party, I was very anxious and worried.  However, my cheerleader let me know, in no uncertain terms, that he was coming over and that I would participate as her sissy.  And I did.  The details of that night are in my last post, Cheerleader Gets An Itch.
The other thing that happened after she brought a new man into our bedroom was that my cheerleader decided that keeping her men secret from each other was too difficult to manage.  She had not told Randall about Jason when she began seeing him, resulting in a few uncomfortable moments when one or the other was attempting to arrange a visit, even though my cheerleader’s dance card was already full, so to speak.  Deciding that she couldn’t live with that, and demonstrating her continued exercise of control over her sexual relationships, my cheerleader told Jason and Dave about each other.  As it turns out, she needn’t have worried.  Both of them seemed to readily accept that they were in our lives solely for the sex, although I don’t actually think that is precisely how it has evolved.  How do I explain this?  It is very tricky and I’m fairly surprised at how the four of us have adapted. 
My cheerleader told Dave and Jason about each of them separately, but with me in the room as she explained to them our situation.  For me, it was embarrassing, to an extent.  It was almost as though I were not present, and yet I was sitting right in the room as my cheerleader explained how she and I had evolved in our new sissy/mistress relationship.  She even told them that inviting men into our relationship for her sexual pleasure was initially my idea.  I remember feeling very small when she told them about that, especially as each of them looked at me as if I was crazy to be willing to share a woman as beautiful and, obviously sexual, as my cheerleader was.  But the point she was making was not lost on either Dave or Jason.  They were permitted to be a part of our life, but only on the terms my cheerleader set, and those terms included me and the fact that my cheerleader loved me and was committed to our marriage.  As for me, I understood that my role in my marriage had irrevocably shifted.  However, I also understood that, as far as my cheerleader was concerned, I was safe.  That much was reassuring.
The ground rules laid out clearly, and accepted by Jason and Dave, my cheerleader was free to carry on with both of them without concern that she had to conceal relationships.  For her, that was important.  After all, she wasn’t concealing from them that her husband was a sissy.  Why should she have to hide that she was having sex with more than one man?  As it turned out, “scheduling” Jason and Dave was not that difficult.  Jason lived in our neighborhood.  He had already established a fairly regular routine where he’d come to our house on Saturday afternoon with plans to stay the night.  He also fairly routinely stopped over on Thursday night after work, but only for a “quickie,” although their quickies sometimes lasted all night.  Dave, on the other hand, being a pilot, had an irregular schedule.  But he learned that Thursdays and Saturdays were somewhat locked in by my cheerleader with Jason, so he simply approached time with my cheerleader depending upon his flight schedule, and she seemed comfortable being flexible about fitting him in.  It was a bit more difficult for me because that meant I had to be ready to submit and serve without notice, as my cheerleader did not really consult with me about when one of her men came to visit.  She would usually tell me one or the other was going to be coming over, but it was her decision alone, and I accepted that reality. 
My role, no matter what my cheerleader decided as far as having Dave and Jason over, was to serve them in any way that she chose.  However, even that evolved as each of her men became more and more comfortable with my role as her sissy husband.  Thus, Dave and Jason became quite comfortable addressing me as the servant in the house when they were visiting.  I should mention, when they were at our house, it wasn’t as though they jumped right in the sack with my cheerleader.  There were times, quite frequently in fact, that I would arrive home from work and find one or the other in our bedroom fucking my cheerleader.  She had let me know that she didn’t mind them stopping by for a quickie, and we’d worked out that I would wait for them to finish whenever I came home to find one of them at our house.  When I say, "we'd worked out," I mean to say that my cheerleader told me how she wanted me to handle those situations.  But other times, when Jason or Dave would be at our house, they might be cuddling with my cheerleader on our couch in the den watching television or something.  Sometimes, these moments would end up with my cheerleader on one of their laps fucking them.  She became very open about when and where she fucked them.  She was in complete control.  But, during those times, Jason and Dave (and my cheerleader) would ask me to bring them drinks or snacks.  If they were watching television, they would sometimes even ask me to change channels for them.  Once, when Dave stopped in for a layover before a flight to Paris the next day, he asked me to launder his travel clothes for him, and I did so without even thinking about it.  Dave and Jason both treated me so well that I didn’t complain or feel put upon.  The important thing for me became ensuring my cheerleader’s happiness.  I had incrementally become more and more submissive in my dealings with her.
Another thing that happened my cheerleader and I spent last summer with Dave and Jason was that we sometimes did things together.  I am a Season Ticket holder for the Washington Nationals.  Jason loved baseball.  So, sometimes he, my cheerleader and I would go to games together.  When we returned home, I would immediately return to “sissy mode,” and look after their needs, including fluffing Jason for my cheerleader.  As for Dave, he and I played quite a bit of golf together when he would be in town for more than a day or two.  He began keeping his clubs at our house and I’d take care of them for him between rounds.  It turns out that he and I were quite compatible on the golf course, and he never treated me in a bad way.  My cheerleader got a huge kick out of the fact that Dave and I played golf together. 
I often wondered if this was normal.  The way I interacted with my cheerleader’s men.  She and I talked about it, but she had no more insight than I did.  Her attitude was, as long as we were all getting along so well, why did we have to understand why it worked the way it did.  I always want to understand things though.  And yet, there seemed to be no ready answer.  In the end, things did work out well.
When it came to sex, each of them was different.  As I have described before, Jason was a kind man, who was always polite.  He accepted my role, I think, primarily because he saw how much it meant to my cheerleader that I was involved.  He did not seem the least uncomfortable with me dressing as a sissy, or with me doing any of the things I did for him as a sissy, including sucking his cock for my cheerleader.  There were times when she would encourage him to let me bring him to orgasm.  She loved watching me go “all of the way” with her men, meaning, letting them cum in my mouth and sometimes even on my face.  I’ve never completely understood that aspect of our relationship.  I know from early in our fantasy days, she loved watching me with a dildo in my mouth.  There must be something about seeing me with my mouth full of dick that she gets off on.  But it obviously isn’t simply that.  It is also watching me submit – seeing me get lost in the act of sucking a cock, of pleasing a cock, and then seeing how turned on I get when a man lets me bring him over the top with my mouth and tongue.  But I won’t lie.  This turn on is mutual.  I love sucking cock.  For her.  Sucking a live cock has been one of the best benefits for me as a sissy.  Sucking dildos and fantasizing does not compare to feeling a living, breathing, pulsing man’s cock in my mouth.  There is nothing comparable.
Dave, on the other hand, was much more of a man’s man when it came to sex.  It wasn’t like Jason wasn’t.  I’m just saying that Jason was so nice.  He and my cheerleader would easily make a great pair, if she weren’t committed to me.  They were very comfortable with each other.  Dave, on the other hand, loved the freedom he had with my cheerleader.  He accepted her terms much more clearly - he was there for sex.  And so he was going to carry out his role.  When they fucked, they fucked hard and with animal passion.  When he was encouraged to let me suck his cock and bring him to orgasm, he would frequently take control of me, holding me at the back of my head and actually fuck my mouth, sometimes fairly roughly.  And if I’m honest about it, I liked it when he did that.  I’m quite certain that my cheerleader liked it also.  She would usually play with herself whenever Dave took control of me, calling me a sissy slut and a cocksucker as he fucked my mouth right up to cumming in my mouth, frequently pulling out in time to jack off on my face.  My cheerleader loved watching Dave cum on my face too.  Another thing Dave loved to do was to fuck my cheerleader while I lay beneath her, licking her pussy and his cock as he fucked her.  I’d done that, but from a kneeling position, the very first time my cheerleader fucked Dave, and it must have been a real turn on for him, because he encouraged it quite regularly over the course of that summer.  He would let me suck his cock and then he’d stick it inside of my cheerleader, fuck her some, and then slip out and go right into my mouth for a few thrusts.  I admit that I loved doing this.  I loved tasting my cheerleader’s pussy on his cock, and especially after he came inside of her and he’d stick his cum coated cock into my mouth.  My cheerleader loved being made love to that way also, and so with them it became a fairly routine thing for us to do.
Everyone was getting something out of the odd relationships my cheerleader and I had with her men.  In a way, even though neither Jason nor Dave would have been present in our lives were it not for my cheerleader, they were my men too.  Does that even make sense?  I mean, they were completely into my cheerleader, and vice versa.  But, I served them in many ways beyond fluffing them for her.  So, they were like my men too.  All in all, last summer was pretty wonderful.  On the days that Jason and Dave did not visit my cheerleader, the two of us got along fantastically.  I was nearly always dressed en femme when home.  As for her, she treated me great, and yet, I was clearly the subservient one in our marriage.  But she treated me so sweetly.  I may be romanticizing it all a bit.  There were many times when I felt very embarrassed about something that would happen or the way she would have me dress for an evening with Dave or Jason present.  That probably sounds stupid, especially in light of how I’ve told how I basically was each of her men’s personal cocksucker all summer.  But, for example, my cheerleader would sometimes make me wear next to nothing, often highlighting the fact that my clit was locked in its chastity cage in front of her men.  She always wore her key around her neck.  Being so exposed was embarrassing, even if Jason and Dave didn’t specifically do or say anything to bring attention to it.  My cheerleader usually would though.  I think she liked to tease me.  Or, she liked the way I reacted to her teasing.  She’d say to one of them things like, “Isn’t she cute?”  Or, “I love keeping her locked up while we fuck.”  Whenever she’d say that, especially referring to me in the feminine pronoun, I would unquestionably respond in the way she wanted.  I’d blush, but my clit would get hard inside of the cage, so the teasing was having the intended effect.  She milked me quite a bit that summer too.  On the other hand, my cheerleader was also very kind and generous about releasing me from time to time to go inside of her, although I could sense that I did not turn her on in the way that I had before.  Jason and Dave were each very well endowed, especially Dave, so although I am not tiny like some sissies, I didn’t measure up to her men.  Then, there were the times we’d be out to dinner or in public while I was dressed in my boy clothes.  She would see a good-looking man and look at me, smile, and sometimes that would be all she’d do.  That was enough.  Other times though, she’d tease me, saying things like, “What do you think sweetie?  Big cock?”  Or, she’d say, “Should I ask him to come home with us?”  She really constantly teased that she might bring another man home to fuck, although up to that point she did not carry through on her teasing.
Jason and Dave are each still a part of our lives, although there have been some other changes to occur since the end of last summer.  One thing, in particular, happened in the Fall, and I’ll tell about that in my next post.  It won’t be long before I’ll be up to the present in terms of telling about my ongoing relationship with my cheerleader.  We are still very happy and very committed to each other.  I am forever grateful to her for allowing me to fully experience my sissy nature.  And I think it has worked out pretty well for her as well.


  1. Gah! Like every great writer, you leave us with a cliffhanger! You write so well Leeanne, and it brings us right into it so much that I feel like I know you and your cheerleader so well, even though we are relative strangers on the internet.

    And once again, this is all so very fascinating because I can feel the love, even when I say to myself, "no way in hell would I do any of this!" I can read it and say, "holy shit, I am so happy that things have worked out for the both of them" because blissfully kinky stories really make me smile.

    It gives me hope that all the people that visit your blog and mine find exactly what they are looking for, without harsh judgements and horrid repercussions.

    How does it make you feel as you've unleashed the story so far? How much are you reliving it as you post? Is that a good thing or not? Does the cheerleader still not know about this blog?

    1. Dear Dee,

      One of my goals, as I have told the Internet world about my personal sissy journey, has been to try to let those reading my story actually feel like they know me and my cheerleader, so if that has been achieved then I am pleased. What you say is interesting. You are right that we "are relative strangers on the Internet." However, I feel like I know you as well from your blog. So, I think that is a good thing. We are able to expand our relationships to like-minded (or, in our specific case, similarly-minded and open-minded) people.

      I realize how fortunate I am that things have worked out as well as they have for my cheerleader and me. My story could have taken a much different turn long ago, especially if my cheerleader had not decided to honor our wedding vows and stick with me when I laid on her the big news about me and wearing women's lingerie. And if she had, no one would have criticized her for doing so. Yes, I am a lucky sissy. I also think things have worked out well for her. I wonder how many women really would enjoy the freedom my cheerleader has? Probably more than some men would like to admit.

      I am always hopeful that people will not be harsh in their judgements. In my case, I have been pleased to find that most are not.

      When I'm writing about an event, or a time period, it is difficult for me as I re-live something that was particularly humiliating at the time. However, once I get it down on paper, so to speak, I feel good about it. I like sharing my story. And no, my cheerleader does not know about my blog yet. Terrible of me, I know. I just don't know how she'd react to me putting this out on the Internet. She worries about that kind of stuff. Obviously, I feel safe in doing it, or else I wouldn't do it. Who knows? Maybe I'll tell her someday. And when I do, maybe I'll ask her to write her own response, as you've suggested in the past. It would be interesting.

      Thanks for being such a great Internet friend Dee.



    2. Its not hard to be friends with you Leeanne, as you are such a sweet and engaging sissy. I actually think I got it wrong, and that we are friends on the internet, but strangers in real life, though I think I have a good handle on you both here online and in meat space.

      If I ever head back towards your neck of the woods, I'll definitely be looking out for the guy with the lingerie underneath hoping I spot you. Check that, if I see that guy walking along with a hot wife, I'll know its you! If you get a wink and a knowing glance your way, that just might be me!

  2. You sound like you and your cheerleader have achieved that delicate balance where you both get what you need/want while you both give what the other needs/wants! Rare and hard to do!
    I love reading your story, it makes me so glad that we've "met"!
    Can't wait for more!

    Love to you both!

    1. Thanks Kaaren. It is, as you say, a "delicate balance." I am very happy, as I believe my cheerleader is as well. I am equally glad that we have become such good friends as well. You are a sweet person and I love our little quips back and forth. Sissy friends forever!

      Hugs and kisses,


  3. Thank you so much for a wonderful installment in your story, Leeanne!



    1. Dear Christine,

      You are welcome sweet girl. And thank you so much for reading it.

      Kiss kiss,


  4. A lovely post Leanne. I have to admit im still getting my head around the cuckold thing but I feel subby to both male and female but prefer a lady running the show, so not too many more dots to connect maybe.

    You have a great eye for an image too! That tiny apron, the tiny white skirt, the subby on her knees with head turned demurely. Any one of these could be a centerpiece to a post.

    lill jo

    1. Dear Jo,

      I understand that being cucked as I have is not something everyone can handle. But for me, it really is about my cheerleader and her being in charge. If it were not something she enjoyed and wanted, then I don't think I'd be attracted to other men. I know that sounds strange given how much I do enjoy sucking their cocks. I just don't know if I'd be doing it if it were not something that I was doing, first and foremost, for my cheerleader.

      And thank you for the compliment about my photo selection. I spend a lot of time choosing them. And I enjoy spending a lot of time choosing them, if you know what I mean. LOL

      Kisses to you too,


  5. Another wonderful chapter of your story Leeanne!

    Your story has had so many climaxes (no pun intended) that's it's really wonderful to read about a 'plateau' of sorts. A summer spent with no major breakthroughs... just continued sissy bliss.

    As always, I wait with baited breath for the next chapter.

    1. Dear Caitlyn,

      Yes. Last summer was quite nice in its own special way. We were somewhat settled with Jason and Dave. The part that I found most interesting as it developed was us doing things together outside of the cuckolding dynamic, although it was always present. I think you'll have a thing or two to say about my next post. A very unusual occurrence.

      Hugs & kisses,


  6. Dear Leanne

    Again thanks so much for your story, both erotic and inspiring. i can appreciate the challenges and also the steady progress of becoming. In truth i love to read about how you relate to your cheerleader and to the men she has brought into your life, how you accept and even want her to enjoy having them openly as her lovers, how your femme self is just a part of who you are, your acceptance of being locked by her, and of course, how you much you have come to love sucking cock both for her and for yourself. While i am sure i underestimate the difficult moments you have had, i do envy you for the journey you have taken. i am on my own journey of feminization and service and i embrace the truth and joy of each step i have taken to become the sissy i want to be, to leave behind the man i once was. Thanks so much for your blog,