The Beginning
It started innocently enough. As innocent as anything is for me, it seems.
I am 50 years old, assigned male at birth and rather feminine. I am 5'6", it seems I inherited my short father's genes. I am in good shape though soft around the edges: a bit of swell in my upper chest, soft belly, wider hips, much less hairy than average and what is there is fair, and my hair is dyed blue and cut into an a-line bob. I often wonder if Mother Nature got distracted when she gave me male rather than female genitalia. Speaking of genitalia, my penis is, at its most erect, maybe 4". I swear that I have seen clitorises larger in some of the porn that I have watched. I call it my clit or my twig since I have the corresponding berries, also small. Often, both my twig and berries seem to want to retract into my body,
I identify as non-binary and trans feminine. What is interesting is that the term sissy does not impact me because I feel emasculated. It impacts me because it exaggerates that I am not a woman by birth even though I have embraced my feminine side for the last ten years. I grew up with two older sisters, both about my size. I could and often did borrow their clothes when I was younger. I have a sense that they knew though have never said anything about it. I would often find some of their clothes mixed into my clean laundry, particularly panties, and I would wear them and put them back in the common laundry basket. They were lovely supportive sisters and, whether they knew it or not, I envied their shapely bodies.
I was never interested in sport, instead nurturing my geeky, loner, introvert aspects and becoming adept of working with computers and software. When I was forty, I sold my third company and decided that I was well off enough to share some with my sisters and parents to assure that they were comfortable and keep the rest and retire. Since then, I have been more out an about in female attire, engaging in travel and hobbies, skiing being one of them.
That is how this all started. I traveled to a new resort, in Colorado, and did not bother taking my skis, just my boots. I joined a ski and snowboard gear service and visited the office to rent my skis. When I arrived, there was no one there but her. Her badge identified her as "CC" and I introduced myself to her and explained that I had reserved some gear. She looked me up and down, taking me in, an experience that left me blushing a bit. I had one of my ski boots with me and I was wearing skirted leggings and a hoodie along with fleece lined boots, rather feminine. She was wearing an oversized branded hoodie from the resort, leggings, and her own fleece boots in a style that matched mine. We were also similar in height and as far as I could tell build.
I was immediately struck by her confidence. Her steady eye contact as she greeted me disarmed me. She politely asked me how I identified, and I was honest with her. She confirmed my name, Simone, on the reservation, and asked me a few questions about my ability and experience. She found some skis and poles for me, the skis clearly marketed toward women based on their decoration and the poles a bright pink. I smiled as she explained that I could exchange them as many times as I liked and that she would be on duty Thursdays through Mondays.
I tipped her and felt her slip a card into my hand as she leaned over to whispered in my ear, "You have been such a good girl, Simone. I don't usually mix my lines of work though you are just too tempting to pass up. Check out the information on my card."
I was flustered and thanked her, leaving the shop and putting the card in my pocket. It was a blue bird day after some new powder snow, so I fetched my other boot and gear and did some turns on the skis which suited me quite well. I forgot about the card for now though not the experience. I wondered if CC was teasing me when she bent over in her leggings, showing me her delicious bottom. It was hard to determine the rest of her figure due to the oversized hoodie. When I got back to my suite, I remembered the card. There was a link to a phone and video sex site that I knew with her information: Calliope: The Snow Princess.
My heart skipped a few beats as I fetched my computer and looked her up. I was already a member of the site, and I was familiar with the search interface. I found her and was struck by her shapely body with full breasts and toned legs. She seemed so plain and girl next door at the gear shop while she looked like the vixen that she described herself as on the site. What's more, she was a dominant. I guessed that her age was accurate--30--and she wrote about being a nurse as well as loving the outdoors, skiing and rafting. It all fit. I was gob smacked! I sent her a quick note with trembling hands so she would know my username and could view my profile.
I was rather descriptive in my profile, and I updated it right after I sent her the message so it was current. I checked back each day to see if she had read my message and I, again, imagine that she was teasing me as it sat unread for 4 days. On the 5th day, the site showed that she had read the message and my mouth went dry. The timing was such that she was not in the shop for two more days, something I imagine that was also deliberate. I tried my best to put her out of my mind though it proved a constant distraction.
I went back to the shop when I knew she would be there to exchange my skis. We exchanged pleasantries though spoke nothing of her other line of work. When she was bringing me my skis, she also handed me a small box with a sly smile though with no explanation.
I tipped her more generously than the previous time and she smiled, inquiring "When will you be returning these?" I noted the date which happened to be on one of her days off the next week, one of the last days of the ski season. She nodded and said, "Perfect. Look out for a few notes from me." I nodded and went on my way.
I was eager to ski but my curiosity got the better of me. I went to the gender-neutral bathroom and opened the package. Inside was a tiny cock cage not unlike the ones I had toyed with on my own. What was interesting is that it was disassembled. I searched the package and found the note: "Hello, Simone. I am hoping that we can start a lovely connection. If yes, put this on--it is self-locking--and answer the note that I will send you the site. If not, return this to the shop when you return your skis." My clit throbbed at the thought of committing myself to this relative stranger. I was soon too engorged to put on the cage, so I put the pieces back in the box and went skiing.
Later that day, after skiing, I showered, being sure to carefully shave my privates, then, before I lost my nerve, I put on the cage, my heart pounding as I heard and saw the magnets engage. I then logged into the site and saw the "new message" icon. With trembling hands, I opened the message, which read, "Simone, if you are reading this, I presume you are wearing my cage. Please take a photo of it and include it your reply to this message. Please, also, tell me your life situation and availability. I am committed to work at the resort until April 30 and then I am off until November 1st. I don't yet have any commitments for the summer. Miss Calliope."
I swallowed, hands continuing to tremble, clit swelling in the tiny cage. I took a photo and attached it to my reply. I explained that I was retired, financially stable, and, like her, had no upcoming commitments though had hoped to do some travel. I let her know where I was based and I pondered that I would have to deal with TSA on the way home, a first part of my submission to her. I took a deep breath and sent the message. Later than night, she replied, thanking me for the confirmation and information and letting me know that she was possibly house sitting in my state this spring and summer and that the house might be a good place to meet. She said that she would reach out to me after April 30 and that buying some of her photo sets and videos would help her decide if she would have me after all. It had not occurred to me that she could ghost me and leave my clit locked up!
