[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. These are the previous posts that tell the story about my sissy journey.]
When I concluded the last installment of my recitation of my sissy journey, I indicated that I would bring my story up to the present in the next installment. Dee Mentia, of Dee-lusions of Grandeur, fame, commented that perhaps I should draw it out a bit longer, being a bit of a sissy tease myself, so to speak. And while I do admit to being a bit of a tease, that I will not be bringing my tale up to the present is not motivated by a desire to tease. Instead, as I thought through the things that have happened since my cheerleader and I moved from our hometown to Washington, D.C., I realized that there is so much more to tell if I am going to provide the full flavor of where we are today in our relationship. So, please forgive me if I leave anyone wishing I would tell my story faster. I have struggled, from time to time, in the recounting of my sissy journey, but now that I have come this far, I want to do the story justice.
Although my cheerleader and I knew that the move was the right one for us to make, especially financially speaking, neither of us fully realized how difficult it would end up being to move away from our hometown, leaving our friends and family behind. And while we did not move so far away that visiting was out of the question, once you begin a life somewhere else, it is difficult to go back to your old one. And so, we found ourselves relying more and more upon each other to occupy ourselves.
Initially, I had to spend a great deal of time settling in to my new job. My cheerleader was not working, although she eventually found a part-time job working in a trendy retail store, more to keep busy than anything else. We had been fortunate when I took the new job that we were able to sell our old home for a very good price. Consequently, we were equally fortunate in finding a new home in a very nice neighborhood that was convenient to my work. One of the things we liked about our new home, aside from its charm resulting from it being a very old home, was that, within our neighborhood, we were very private.
I don't know whether that had anything to do with my cheerleader's relaxing her usual limitation that I only wear feminine clothing, openly, in our bedroom, but shortly after we settled in to our new home, she let me know that she wouldn't mind if I wanted to wear my nightgowns around the house more freely. I was, initially, uncomfortable with doing so. It wasn't that I didn't like the idea. In fact, there had already been occasions of me dressing en femme when I was home alone. But there was a big difference in wearing lingerie to bed with my cheerleader, from casually wearing lingerie around the house. But my cheerleader seemed almost insistent that I do so, and so, reluctantly, at least at first, I did so. The result of this new freedom to express myself in a softer and more feminine manner led to more frequent sexual episodes outside of the bedroom, and mostly involving me performing oral sex upon my cheerleader. And another by-product of me wearing feminine clothing more frequently when at home was that my cheerleader became more and more dominant with me. And I don't mean dominant in the classic Dom sort of way. It was more subtle than that. In fact, it may have been more because, when dressed in soft feminine clothing, I become so very submissive, that my cheerleader sort of naturally fell into a more controlling role in our relationship. To me though, the thing that was most interesting to notice as things developed was how comfortable she seemed to be in assuming that role.
Sex in our bedroom continued on as it had been. My cheerleader was now fully involved in the fantasy we re-lived repeatedly that involved her selecting some male friend of ours and making his cock the one I would first prepare for her, and then fuck her with. And while we never talked about what this fantasy may have meant to her, I thought regularly about what it meant that my cheerleader got so turned on by imagining that some other man was fucking her, or that her sissy husband was sucking their cocks for her. As for her enjoyment of watching me clean my sperm from her, there was no need for me to wonder about that. My cheerleader loved it. I would never have thought she would react so to me eating her creampie as she did, but she simply expected that of me at this point in our relationship.
I'm going to finish this part of my story by telling of what I consider to be a very significant event. We'd been in our new home for about six months. We had met some new people, but had not developed close friendships yet. So, we still spent most of our time alone together. On our 25th wedding anniversary we went out for dinner at a very nice D.C. restaurant. For her, I had bought her a new gold watch, that I gave to her in the restaurant, that she seemed to really love. She told me then that my present was at home. When we arrived home she went upstairs and returned wearing a pretty pink negligee. She was nude underneath of her sheer gown. She handed me a package wrapped in pretty pink paper tied with light blue ribbon and a bow. When I opened the package, I was caught off-guard. My cheerleader had bought me a matching negligee, but mine included a red panties and bra set. I looked up to find her watching me intently, as if wondering what sort of reaction I would have to my cheerleader buying me lingerie for an anniversary gift. "Well, what do you think?" she asked. Not sure what I should say, I told her it was beautiful and thanked her. "Go put it on," she told me. "Now?" I asked. "Of course," she said. "Now go on. I'm going to open some wine." And so, I went to our bedroom to change into the pretty pink gown my cheerleader bought me.
When I came back downstairs, I called for my cheerleader, but she did not answer. I walked around to each room looking for her, but she was nowhere. Finally, confused as to where she could have gone, I looked into our very private backyard. It was then that I saw her sitting on a loveseat located on a small, raised patio in the back corner of our yard, the accent lighting of our yard illuminating her sitting there sipping wine, wearing her gown. I opened the door and called out to her. "Come on," she replied. I was...well, honestly, I don't know what I was. I would never have thought of going outside dressed in a nightgown. I hesitated, unsure what to do, and she called down to me again, "Come on silly! No one can see us. It's a beautiful night! Come on!" And so, feeling funny about it, I nonetheless walked out to join her.
She handed me a glass of white wine and tipped her glass to mine, "To us," she toasted me. "To us," I responded. I sat down on the loveseat beside her and she cuddled into me, our soft nylon rubbing together feeling electric to me. I don't know how to explain how I felt just then. While I was nervous, I also loved it. We seemed so comfortable in that setting, two feminine creatures, sharing a special moment. We kissed and petted as we sipped our wine, and soon my anxiety eased away. Before long, I was on my knees between my cheerleader's thighs, kissing and making love to her pussy. She was relaxed and enjoying it immensely. I had been worshiping her sex for quite a while when she asked, almost out of the blue, if I wanted to suck a dick for her. I glanced upward, confused by what she meant. For a second, I thought she was actually asking me if I would suck a real dick for her. Before I could verbalize a reply, she reached down next to the loveseat and came up with another package wrapped just like the earlier one. She handed it to me saying, "I bought you another gift." She then watched as I began opening it. When I removed the top and lifted the pink tissue paper her second gift was revealed. My cheerleader had bought me a dildo for our anniversary. And not just any dildo either. This one was called a Realdoe. For anyone who does not know what a Realdoe is, click on the link. By this point, butterflies were churning inside my stomach. My cheerleader took it from me, expertly turned on the vibrator, and then slipped the end intended for her pussy inside of her, and then looked at me and said, "Go on sweetie. Suck my cock." And so I did. On my knees, in a worshipful position beneath my cheerleader, I gave her a blowjob on our new dildo. And for her part, she really got into it, urging me repeatedly to suck her cock. Not the cock. Not some fantasy man's cock. Her cock.
After I had sucked the cock for her for a long time, bringing her to multiple orgasms, aided no doubt by the vibrator and the bulbous end inserted inside of her. Finally, she told me to fuck her. Beckoning me to sit on her lap, I stepped out of my panties and climbed upon her as she guided my stiff penis inside of her. I was so turned on, as was she, that I was spewing inside of her in no time. She held me close to her breasts, my own fake breasts tight to hers, and kissed me on the neck, whispering how much she loved me. And I professed my love for her as well. All in all, the moment was magical. My cheerleader had not only fully accepted my feminine desires, she had completely bought in and was letting me know how much she loved me as I was. I remember thinking, 'How did I ever get this lucky?'
As my penis softened and slid out of her, she nudged me down to clean her out. I could never deny my cheerleader anything by this point. Obediently, I kneeled between her thighs again and began licking her clean. My cheerleader relaxed back against the sofa, savoring my mouth on her wetness, repeatedly sighing how much she loved what I was doing. When I finished, she took my hand and led me inside and to bed, where we cuddled together and fell asleep.
Twenty-five years of marriage, and we had celebrated as few couples probably ever had. And although we did not discuss what happened, that night was a moment that I believe led to where we are now. My cheerleader completely accepted the feminine me. And really, more than accepted, she let me know how much she loved the feminine me. Was it possible for me to love or worship my cheerleader more? Recall, she was the first and only woman I had ever been able to make love to. And now, she was drawing me deeper into my feminine nature, and telling me she loved me this way. Yes. It was possible for me to love and worship her more. And so, when things began to evolve, I was already inclined to give her whatever she desired.