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I was filled with anxiety as I reflected on my relationship with Beth over the past year. Beth & I had been together for almost three years now. She was an uninhibited beautiful woman who pushed my limits, not only ually but in every way possible. But this most recent chapter had taken me to places that made me question who I was. It started on a crazy night when she and her girlfriends introduced me to crossdressing. Following that experience, I started to wear panties to bed, then to work and eventually I was wearing exclusively women’s underwear. I explored my feminine side through role playing, in fact I embraced it. I kept my body clean shaven, I learned to do makeup, my hair, and acquired a wardrobe of women’s clothing. I practiced walking in heels, adjusted my voice to more appropriately reflect my persona, and I focused on my mannerisms, ensuring they were feminine and more importantly, submissive. Soon I was spending nearly all of my time outside of work as Kelly.
My feminization continued in the bedroom as well. Beth and I had incredible throughout our relationship and that was true even through this process. But it was very different as I began to take on the female role in almost every instance. Beth, and sometimes her friend Carolyn, would play the role of my male partner, teaching me how to fufill my feminine role and to prioritize the satisfaction of my partner. They would wear a strap on phallus and have me practice oral , on my knees, staring into their eyes, taking as much of them as possible into my throat while learning how to use my hands in concert with my lips. I also learned how to have in a variety of positions as they shared their experiences of what sensations, movements and motions excited their male partners.
Quite honestly, I liked it. Alot. The feeling of being filled was incredible and every withdrawal created an immediate desire to be filled again, anticipating the subsequent thrust. I loved feeling my partners hands on my hips holding me, controlling me, or hovering over me while they were between my legs, totally in control while I provided them pleasure. Even when I was on top, lowering myself on them rhythmically, it was erotic as my purpose was to provide them pleasure. I even liked when I was asked to use my mouth to provide pleasure. To submit, to take that member in my mouth, to use my lips, tounge and fingers for no other purpose than to bring someone to orgasm. To kneel before them, submissive in position, looking upward for approval, my reward being their pleasure and possibly semen.
And the more and more I role played, the more and more I wondered about the real thing, desired the actual experience, wanted to pleasure a real man. And it happened. Beth had friends over, all of whom were discreetly aware of my journey, and I ended up with a man named Tim, with whom I spent the evening and following morning. We had multiple times and it was incredibly erotic and satisfying, better than all of the role playing.
But when the thrill of the experience was over, when I awoke that next day, I began to get into my own head. My confidence in myself clearly wasn’t as strong as I had always thought. There was no doubt I had enjoyed the entire experience. Not only the night with Tim, everything leading up to it as well. But now I felt a sense of guilt. Was what I did right? Was it ok? That sense of guilt alternated with waves of anxiety. Who knew what I had done? So many people were at the party, did they tell anyone? They must have, right? Did everyone know? How many people thought I was gay? Was I gay? I didn’t think so, but I must be…right? The thoughts just filled my head in an endless manner and the anxiety and guilt made me lose my appetite and my ability to get any good sleep.
I wanted to be alone. I worried that any interaction with Beth would push me further down this path. It was such a conflicting thought because I enjoyed it, but now my emotions were out of control and I needed time to get myself back in a good spot. I dreaded work each day. I had an overwhelming feeling each day that everyone knew I had been wearing panties to work and that I had feminized myself and given myself to a man. I kept my head down and just tried to get through each day. I went back to only wearing male clothing and I stopped shaving my body. Not that hair rapidly grew back, and where it did, the stubble was a constant, irritating reminder of the journey I had been on. And one night in a quest to eliminate my guilty feeling, I threw all of my feminine possessions into a couple of large shopping bags clothes, makeup, hair care, lotions, breast forms, shoes and lingerie, and began to take them to the dumpster. But I stopped. I couldn’t do it, and the bags ended up on the floor of the closet, a conspicuous reminder of what I had done.
Beth gave me space for a while but eventually she started to again spend most of her time at my place. She had to be aware that I was stepping away from my feminization but no mention was made of it. After a few weeks, we had for the first time since that weekend and it was great. It was a long night of fun, playful , like it had been in the beginning with no mention or acknowledgement of the chapter that had just played out. Things seemed to be back to normal at home. At work, I still wasn’t my normal self and on Friday of that week, my department director came by my desk and asked to see me in his office near the end of the day. I went to his office at 2, nervous because I was never asked to come to his office. Was this it, did they know, were they going to confront me? I walked in and sitting in his office was the human resources manager. I almost passed out. After some pleasantries, I was asked to sit with them at a small conference table where they informed me that my manager had resigned and I was being asked to fill that role. I was getting promoted!
With each day, I was more and more in control of my thoughts and emotions. Beth and I were having fun together in and out of the bedroom. The new work responsibilities were challenging and kept me distracted. But those bags in the closet were a reminder and one night I found myself thinking of how much fun I had while playing that feminine role. Those thoughts occurred on and off, but I generally moved past them, thinking that was a part of my past. Over the next few weeks, work became very stressful. My first big project in my new role was coming due and I was very involved with my team. We presented the project on a Friday morning to the senior team and received very good feedback. A bunch of the people on the team went out to celebrate after work and we ended up at a bar near my place. I called Beth and asked her to join us, but she said I should enjoy myself because she had other plans and likely wouldn’t be back tonight. I had a great time with everyone from work and was very proud that my first big responsibility went so well. I didn’t stay out too late, but I had started early and drank a lot in celebration. I chose to leave my car and make the long walk home to help clear my head.
I walked into the empty apartment, and grabbed a beer from the fridge. I went into the bedroom to change, grabbed some shorts and a sweatshirt and started to take off my suit and hang it nicely. As I placed it back in the closet my attention was pulled to the bag on the floor. Admittedly, my inhibitions were subdued by the alcohol and I was feeling very horny. I completely undressed and stared at myself in the mirror on the closet door. I was in a state of in between. Hair still slowly growing back on my body, some areas still clear while others like my genitals had now a very thin, trim covering.
My waist was still thin and my weight maintained low. I was still running and eating well so that was no surprise. And my hair was still shoulder length, even a bit longer now. I was semi erect and I worked to tuck myself between my legs. I admired myself and looked at the bag. I debated whether I should dress and do my makeup. I grabbed one of the bags, sat on the bed and rifled through it, quickly locating a favorite pair of panties. I slid the satin emerald green cheeky style over my legs and pulled them up on my hips. I ran a finger over my erection through the satin before standing up and tucking it uncomfortably once again back between my thighs. I decided to search for the breastforms in the bag and felt them at the bottom. It was quite a bit of work to glue them on so I looked for a sports bra to put on to hold them in place. I had to get the other bag and after a brief search, I found a black one. It struggled more than I should have to slide it over my head and drunken arms but once in place I inserted the breast forms and layed back in my bed.
I awoke to a feeling of happiness, enjoying my erection being teased by a fingernail slowly tracing up the length of the satin covered shaft, stopping just before the head as it extended beyond the top of the panties. I didn’t want it to stop but eventually I opened my eyes and saw Beth standing over me, continuing to tease me. Beth looked down on me with a smile. Her long auburn hair was a mess, she wasn’t wearing her bra and I had a sense that she had this morning before returning home to me. She told me she was surprised and happy that I was exploring Kelly again and climbed in bed next to me.
Our hands slowly explored each other as we laid together and talked. She asked about my day at work and my evening out. She noticed my car wasn’t outside and assumed I had quite a bit to celebrate. She was genuinely happy for me. She said she had spent the evening with James, a friend of hers that she spent the night with when I had met Tim. As always she was quite matter of fact in describing the that they had last night and, as I had suspected, this morning. Eventually she asked the question I knew was coming, ‘What made you decide to dress again? And why did you stop for so long?’
I addressed the first question directly because I was drunk and horny and I wanted to. To answer the second, well that was much more involved. I explained to her my conflicting feelings and how they overwhelmed me. I am not sure how long we talked, but as always, she was understanding and easy to talk to, and she wished I would have shared my feelings with her sooner so that she could have helped. But she had wanted to give me space to sort through it all and I told her I needed that.
She asked me if I was going to continue to be Kelly from time to time and I responded by asking if she wanted me to. ‘That’s not up to me. I will support whatever choice you make. I just want you to be happy and enjoy your experiences, and not regret them because you’re concerned with what others think.’
She ran her hand up and down my hip and continued, ‘You know my position, I like to have different ual experiences. It makes me happy, not a bad person. What’s wrong with me having with Amy when she is around? What’s wrong with being biual and enjoying both men and women. I get it that it might not be for everyone, that’s what only you can decide. But there’s nothing wrong with it if you are open and honest, like we are.’
As we laid there caressing each other she said we should shower. I was disappointed thinking any ual interaction was out of the question and then she added ‘together’. We stripped each other of our clothes and headed to the shower. It was a bit cramped but we had fun. Beth knelt before me and used her mouth to get me fully erect. But then she grabbed her lotion and razor and asked if she could shave me again. I actually enjoyed being clean shaven, it was an erotic sensation that I carried around with me everywhere I went. So I allowed her to shave my entire body and when she was finished she knelt before me and gave me an incredible blow job. She kept my cum in her mouth and stood and kissed me, sharing the reward of her efforts. I was quickly falling back to my feminine side.
We dried off and Beth walked to the bedroom and dumped Kelly’s bags out onto the bed. She grabbed all the makeup and hair care items and brought them into the bathroom. She said she would go clean up while I made myself up. I paused for a moment, wondering if I wanted to plunge back in, but I thought about what Beth had said and how much I actually enjoyed it and decided I would. Beth hung all of Kelly’s clothes up, put her lingerie and underwear into our dresser, set the shoes out and put the lube and lotion on my nightstand. She brought in a bra and panty set that I particularly liked. They were deep blue with small yellow hearts in a small area where the panties dove between my legs and on the material that connected the cups of the bra together. The panties were a hybrid of a thong and cheeky style, the thin material riding between my cheeks and then rising up and out over the top arch of each cheek. The set was primarily satin with lace trim. As I put them on I tucked myself away appropriately as a tingle ran through my abdomen. Beth applied the adhesive to the breast forms and placed them in the cups and pressed them into my chest. In moments they were an integral part of my body. Beth picked out a floral mini skirt and a deep blue shirt that tightly accentuated my breasts. I looked in the mirror and I was Kelly again.
We spent the afternoon sitting with music on in the background and chatting about a variety of topics. We talked about clothes, we talked about hair and makeup and we talked about men. As the afternoon went on, Beth asked if I would go out to dinner with her, insisting that I looked very feminine and no one would notice. But that was a line I wasn’t ready to cross and flatly refused. Beth asked if Kelly was here to stay or would I be putting her away. She said she was asking now before I had any wine so my head would be clear. I told her that Kelly was likely a part of my life going forward. She smiled and kissed me. That kiss led to more passionate kisses, that led to fondling, that led to my fingers slipping in her panties and quickly bringing her to orgasm. She thanked me and said she wished she could do the same for me but would take care of me later.
After a light dinner, we refilled our wine glasses and sat close together on the couch. Our time was quickly interrupted by a knock at the door. Beth answered and let Carolyn in. She was surprised to see me because my car wasn’t there and she assumed Beth was alone. She was also surprised that I was Kelly since Beth had told her that I had stopped dressing. She made a snide comment that I looked good as a woman, since I no longer had a shred of masculinity to cling to, and that I had a glow that only a woman that has been fucked by a real man could have. She asked for wine and I obliged. The three of us sat and talked and finished off a bottle and were well into the second when the talk turned to Kelly, and who I was going to be with next. Carolyn pushed the topic, stating that I might like the clothes, I might like the hair, I might enjoy acting feminine, but she knew the only reason I did any of that was the desire to fulfill the feminine role ually. And the only way to do that was to find a man willing to be with me. She asked if I agreed, which I did with some sense of embarrassment, because she was right.
‘How are you going to do that?’, she candidly pressed on. She and Beth talked about what it was like to date as real women. How it wasn’t easy, but it wasn’t difficult to find a guy for a night, but to find someone that you could be in a relationship with was different. I hadn’t thought that through but pushed back that I didn’t need a relationship. Carolyn argued back that maybe right now I don’t foresee that, but if I continue down this path I will want that. And as I thought about Beth and how important our relationship was to me, I realized she was probably right.
‘So what’s your plan, Kelly? Do you intend to go to Marie’s or some other bar and pick up men and then bring them home to surprise them with what’s between your legs?’, Carolyn pointedly asked in a derogatory tone.
‘No, that wouldn’t be a good idea,’ I answered, while Beth was staring at me as the reality of my situation was sinking in.
‘Why don’t you accept the fact that you’re gay and just go to gay bars and find men that’ll accept your cross dressing fetish? You have to agree that has a better chance of leading to something.’.
While Carolyn was right, I told her I wasn’t ready for that.
‘You’re not ready to go out in public? Or you aren’t ready to admit you’re gay?’
I didn’t answer, my mind was trying to avoid the question and the reality of the circumstance while simultaneously evaluating all the options.
‘I do have a few friends that are gay that could show you around that scene,’ Beth offered. ‘I’d be willing to go with you as well if you want my support.’
I didn’t say anything, no one spoke, and the silence was deafening to me.
But Carolyn wasn’t going to let up. ‘Is your plan to rely on Beth’s catalog of intimate friends?’
I told her that I didn’t know what my plan was, but at heart I only felt comfortable with the people Beth introduced me to. Beth thought for a minute or two and then said she had one friend other than Tim that was biual, but hadn’t talked to him in awhile and another friend who she was certain was bicurious but he hadn’t opened up to her about it. She again brought up her few friends that were openly gay. Carolyn said I should just start hanging out with them. Beth continued to think and a smirk came across her face. I asked what she was thinking and she said she had a few friends that were a little kinky and might work out, on their terms.
I asked what she meant but she wouldn’t answer directly. Rather she started to ask me questions and the amount of wine I had consumed removed any inhibitions and I answered her candididly. The first few were easy to answer, but as she progressed, I had to carefully consider my answers. Would I have in front of her? Would I be part of a threesome? Would I have in front of a group of people? With a group of people? Would I be ok with someone other than her controlling me? Would I consider bondage? We talked about each of the topics for a while, each providing our thoughts on each question while finishing the second bottle of wine. Carolyn occasionally injected derogatory comments about my situation while sitting next to Beth.
As the conversation was coming to a close, Beth stated she possibly had something to work with, and I was aroused by the different possibilities filling my head. Carolyn on the other hand concluded that I was desperate and pathetic, reliant on Beth and that I needed to figure this out on my own. She said I should skip the facade of dressing as Kelly and just be open about being gay and things would be much easier. She told Beth that she was going to leave but Beth encouraged her to stay, adding that we all had quite a bit of wine, and suggesting that they could spend time together. My heart sunk as I quickly realized that Kelly would not be included. Beth disappeared into our bedroom and Carolyn followed her. Before Carolyn closed the door, she told me that sometimes girls get all dressed up and anticipate a romantic night only to be left alone, adding that she hoped the couch was comfortable. As the wine made my eyes heavy, I could hear the sounds of their ual encounter, and I fell soundly asleep.
In the morning, I awoke to the sounds of movement in my bedroom as the sun beamed through the living room blinds. I was still exhausted as the couch did not provide the comfort of a bed and I realized I had not taken my makeup off and now it was smeared across the sofa pillow I had slept on. The bedroom door opened and Carolyn emerged. She came over to me and kissed my cheek, smiled, said I had missed a great night and quickly and quietly grabbed her purse, slid her shoes on, and headed out the door.
ero
