Please read 1 -- 17 before going reading this one.
The crossdressing has begun!
After David asked me to start crossdressing him and I spent hours online looking at clothes both him and I would like. It was actually quite a turn on as the things we ordered started arriving and I would try them on. It took us a while to get the sizes right, but after some trial and error we started nailing all our purchases. We bought a host of panties, both thongs and boy shorts, bra's, pantyhose, high heels, nightgowns and Chemise', a couple of cheap wigs and a few oversized dresses.
I couldn't tell you how many times I rushed over to his house after work, to find packages awaiting me, then trying on my new clothing and modeling it for him. Countless nights were spent with me arriving after work, putting on a pair of panties, a bra and wandering around his house in a soft knee length nightgown, or a long free flowing dress with pantyhose and heels on. I was actually becoming quite aroused and loving being dressed for him. I oved going to bed wearing a night gown and panties. I started shaving every part of my body, as I later joked, I shave from nose to toes and everything in-between.
I wouldn't wear the clothes out on public, only at his house after work. Once we had all the basic and lingerie items down, we started buying more clothes, like jeans and shirts and just your everyday women's clothing, but really stayed focused on the undergarments and sexy outfits. We even bought breast forms so I could wear them in my bra and actually "have tits". David loved it! As did I.
We even got to the point when I needed help with make-up, that he invited his co-worker named Amanda over numerous times to have her teach me how to do it. Amanda was a bit of a freak and was very open to sexual experiences. Her only request for helping me out or her "price for doing this" was to watch us fuck as she masturbated. I had no problem with that. I wasn't interested in pussy anymore, so I didn't care if she watched.
I spent weeks wandering around his apartment dressed as a woman and to tell you the truth I really started enjoying my role. I felt more free wearing panties and bra's then my boy clothes. Most days I would go to work wearing panties under my pants, sometimes a sports bra and I couldn't wait to get to David's and change into something way more feminine and more comfortable. I had finally come full circle. Years ago, I was a regular guy who got introduced to homosexual sex with a transgender female and now I am a cock loving, crossdresser who was more comfortable as a woman than as a man. I was ready to live this lifestyle permanently.
At this point in our relationship, I was actually hoping David would ask me to marry him. I would have said yes and I would have wanted to take my transformation further, by getting breast augmentation and becoming more of a female. Externally I still lived my life as a man, went to work as a man, but at night when with him I was all feminine. Even at my own place, I would be home at night, in women's clothes, with wigs on and tits in.
There were weeks of discussion about what female name I wanted. We would lay in bed kicking around names like, Brandy, or Jennifer, Keri, Tina, Julia or Heather. We tried getting close to my real name with things like Mika, Mary or Michelle, but one night it came to me... Samantha... Yes, that's it... Samantha Meyers. I was now Samantha! Sam for short and was well on my way to transitioning to all woman.
During our time together David and I became couch potatoes. Outside of our sexual exploits, we rarely did anything physical, and since we were both foodies, we ended up putting on -- what I like to call -- a bit of dating weight. Personally, no matter how aroused I was wearing the lingerie and sexy outfits for him, I knew I wasn't as skinny as I once was; and in my opinion looked like a chubby guy in drag.
I wanted to lose weight and I wanted us to get into shape. I convinced David to join a local gym and start working out, so I could lose the weight and look better for him dressed up and we could both get into better shape. David agreed and as tedious as it was, strenuous it was, as sore as we would get, we struggled through it and after a while started seeing results.
One night just before our 1-year anniversary we went to the gym. On that day we ended going later than usual, due to a previous engagement. When we walked in, we only had just over an hour before they closed, so we had to get on the treadmill and get running. Usually, David and I would go before dinner and end up gong out to eat, or preparing healthy meals at home after working out and showering up. As the crowd started to thin, David and I were the only two men left inside the place. There were three girls working out on various machines and the only employee in the place was a young female.
We both wanted to shower before heading home and headed into the locker room. David got undressed and headed to the showers before I did, because I had a few text messages to return before I grabbed a shower. After stripping down and wrapping my towel around my waist, I grabbed my shower toiletries and started to walk around the corner to the showers, when I saw David in his shower stall.
The curtain was open a bit and I could see his back and naked ass. His head under the shower head, the water running down over his shoulder, neck and back. David ran his hands through his hair a few times, just enjoying the warm soothing water. When he turned around, he saw me standing there watching him. David smiled and with his index finger extended motioned me to come and join him. I was resistant at first, not because of showering with him, but because we were in public at the gym. But then I remembered the only people left in here were females, so who was going to see. I shook my head yes, walked towards him and dropped my towel as I entered into the shower stall with him.
