Cheerleader Does A Sleepover

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

My cheerleader continued seeing Randall after that first month when Andrea was mentoring our developing relationship.  He made a point of seeing her each of the next several weekends, usually making a “Date Night” out of it.  He’d show up at our house to pick her up and take her to dinner, returning later to spend the night with her.  My cheerleader looked forward to her “dates.”  We developed a bit of a routine where I would assist her in “getting ready” for them.  And by “getting ready,” I mean the entire process of primping and preparing for Randall.  My cheerleader seemed to enjoy having me serve as her handmaiden, so to speak, before her dates.  I would help her bathe, wash her hair and, of course, shave her (in all appropriate areas), and then select a sexy set of lingerie and a sexy outfit for her to wear.  I am now solely responsible for maintaining her shaved pussy.  It’s kind of interesting the way she became so fixated upon me doing that for her.  It is like that is her way of ensuring that I bless her giving herself to men because of the active role I take in “maintaining” for her what she gives to them.

As for me, my role was always to play her sissy when Randall was present.  I would sometimes dress in one of my French Maid dresses, although not always.  Sometimes, I would wear only bedtime appropriate lingerie, and there are other dresses that I wear from time to time.  The primary focus is that I present myself as a sissy and submissive in their company.  My cheerleader treats me with the utmost respect, as does Randall, but I am unquestionably “at their service.”  By, “at their service,” I mean that I do what they want me to do.  Sometimes, Randall will take my cheerleader to our bedroom alone and I won’t be a part of their lovemaking, although my cheerleader always saves a bit of Randall for me after he leaves.  That is one of her major turn-ons and another thing she does that I believe is her way of ensuring my acquiescence in our lifestyle.  Other times I am asked to fluff Randall for her and am permitted to watch them as they make love.

There was one occasion that my cheerleader went on a date with Randall that I found especially unsettling.  It was a Friday night and she had dressed very elegantly especially for him.  I was wearing an especially sissy outfit that night.  They were going out to dinner and then a performance at The Kennedy Center.  My cheerleader told me they would be late as they left, but asked me to wait up for them.  I spent that night alone knowing that my cheerleader was on the arm of her man in a very public place enjoying an evening during which I would have loved to have been the man with her instead.  I was feeling a bit down and lonely about the entire thing, but realized I could do nothing about it short of exerting some control that I’d long since abdicated to my cheerleader.

Around midnight, long after the show would have ended, my cheerleader called me.  My anxiety was at its peak when my iPhone rang and I answered it immediately, actually a bit worried by then.  My cheerleader said hello and asked how I was.  I told her I was fine (lied) and asked where she was.  That was why she was calling she told me – she wasn’t coming home.  Randall wanted her to stay at his house and she was asking for my permission.  I suppose I should have given her credit for asking, but at the time of the call, I didn’t really feel like giving or withholding permission was within my power.  I just recall feeling like she was really calling to tell me that she was spending the night with Randall, and so I told her that if that was what she wanted then I suppose it was okay.  She thanked me and said she’d see me in the morning.

I spent a long, sleepless night alone in our bed.  My cheerleader had been away once before with Randall for a weekend, so it wasn’t a foreign concept that she would spend time away with him.  On the other hand, this was the first time I was left alone while she stayed away with him.  My imagination ran pretty wild with worry that this would become a regular thing for them.  I really did not want that.  As it turns out, it hasn’t become a regular thing.  But on this occasion, it was difficult for me.

I was still in bed in the morning when my phone rang and it was my cheerleader.  Randall had to work that day and they had not awoken in time for him to bring her home.  She wanted me to come to his house to pick her up.  Something about that got to me.  How do I explain why that bothered me so?  After all, Randall had been fucking my cheerleader regularly for months by then.  I had sucked his cock.  He was a regular guest at our home.  Somehow, though, me having to go to his house to pick up my cheerleader to bring her home after he had been fucking her seemed more, I don’t know, like I was being used.  Does that make sense?  I still get upset when I think of the occasion.  Of course, I did it - and was rewarded for doing so by my cheerleader.

Randall lived in a nice section of Arlington, Virginia.  When I pulled in front of his house my cheerleader came out to our car.  She had, obviously, not packed for spending the night.  She was barefoot, wearing one of Randall’s t-shirts and a pair of his pajama bottoms that she was able to tie at the waist to hold up.  I remember thinking how sexy she looked wearing her man’s clothes.  She had her evening gown over her arm and her heels in her hand as she came to greet me.  I could tell that she understood what she was asking me to do under the circumstances.  She smiled and kissed me as she thanked me for picking her up.  I, of course, told her that I was happy to do so.  It was apparent that she had not showered yet either.  On the way home she asked me to stop and get her a cup of coffee and a pastry, and I got one for myself also.  We engaged in small talk about the show the previous evening.  She said it was really good and she wished I could have seen it, which I also wished, making the entire event that much more difficult for me.  All in all, the ride home was uncomfortable, but less so than I thought it might be.  My cheerleader had become very good at giving me space to work through the difficult times I sometimes experienced when she was with Randall. 

When we arrived home my cheerleader told me she was pretty tired.  She had not gotten much sleep the night before.  Thus, we were in the same boat, although for different reasons – she had not been up all night worrying about me, or us.  The wry smile she flashed when she told me she was tired sent the clear message as to why she had not slept much.  She wanted to crawl into our bed and take a nap and asked me to join her.  We went to our bedroom and each removed our clothes to get into bed, her naked except for her panties, and me wearing my panties, bra, and slip that I had worn out under my clothes to pick her up from Randall’s.  My cheerleader was all snuggly and huggy with me that morning as we held each other in our bed.  I was happy to be so close to her.  However, I believe her actions may have been primarily motivated to help make me feel better about the fact that she had spent the night out with Randall.  Before long I was in a familiar place, removing her panties to pleasure her.  As I removed her panties I could see that she was still carrying Randall with her.  There was a thick layer of his cum inside of the gusset, and plenty more leaking from her.  Her excitement as she anticipated my discovery of her messiness was noticeable.  After I orally pleasured her for a while she asked me if I would like for her to unlock my chastity cage.  Of course!  I did!  She removed the key from around her neck and handed it to me to unlock my cage.  I was so excited anticipating entering her for the first time in a month, even if it would be with some remnant of Randall still within her.

My penis was throbbing with excitement by the time I managed to wriggle it out of its plexiglass prison.  My cheerleader was watching me with anxious anticipation as well.  She opened her thighs, inviting me to enter her.  I slid inside of her easily, pressing completely within her as she accepted me with no trouble at all.  One of the biggest adjustments that occurred between me and my cheerleader after she began fucking Randall was that my penis, although not entirely unsatisfactory to her, now clearly did not have as impactful of an effect upon her when we fucked.  Still, I don’t think it was altogether a pity fuck when she let me make love to her in this manner.  I think she actually enjoyed the softer way that we fucked, as compared to her and Randall.  Being in chastity had taught me to appreciate the opportunities that my cheerleader allowed me to penetrate her.  And yet, it rarely took me long to orgasm.  I certainly wasn’t in Randall’s league as far as staying power, another difference between us that I know my cheerleader was appreciative to me for allowing her.  When I came inside of her she sighed and thanked me, nudging me to clean her again.  When I finished and returned to cuddle, she told me that she was sorry if her spending the night out had upset me.  She told me she didn’t really want to, but that Randall seemed intent upon her doing so and she didn’t want to press the issue, although she promised that she would not make it a regular occurrence.  I was thankful to hear that she didn’t really like spending the night out and away from our home, and decided I would try to deal with it the best I could and hope it did not become routine.

Between visits with Randall, our life remained much like it had before my cheerleader cuckolded me.  The main difference was the level of comfort we began to have with me dressing in a feminine manner more openly.  There were also subtle differences in duties, with me taking on a bit more of a submissive role.  And yet, we were very much a married couple in our day-to-day activities.  Although Andrea had encouraged my cheerleader to seek out other men, she did not do so initially.  I think she was operating in a comfort zone with Randall and me.  Everyone knew each others’ role in our cuckold relationship and that made continuing onward solely with Randall easy for my cheerleader.  However, she did tease me from time to time when we’d see a man that she found attractive.  But I attributed that to her liking to play with me because she enjoyed watching my response to her teasing.  That did not last much longer after the night she spent the night with Randall.  In my next post I will describe how my cheerleader branched out to another man.