Mikes First Transgendered Pt. 18

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.

David stepped aside, allowing me to get under the water as his hands rubbed up and down over my shoulders and back. The water felt so warm and relaxing as his hands gently caressed over my skin. David and I washed each other with his luffa sponge and just enjoyed being alone, warm, wet and naked in the shower. Just as David was rinsing the shampoo from his hair, I was standing face to face with him. When he finished rinsing the water through his hair and away from his face our eyes met.

I was in awe of his sexy body and was so turned on by being in the shower with him in the gym. I reached my hand downward and softy caresses his crotch feeling his soft cock, hanging in between his legs. I wanted to suck his cock and I wanted him to fuck me right here in this shower. David looked at me with a smirk and said, "Here?"

"Yes." I replied.

"What if we get caught?" He asked.

"Who's here to catch us?" I asked.

David and I leaned in towards each other and our lips met. We softly kissed as the warm water trickled down our bodies, my hand still holding his cock feeling it slowly getting harder and harder. My cock slowly getting erect as his hand reached down to mine. We stood kissing for a few minutes softly stroking each other off. David spun me around and guide my body down at the waist. He got down on one knee and I felt his tongue start swirling around my asshole. I softly whimpered out in pleasure because I enjoyed getting my ass eaten out. David licked and tongued my asshole for a bit of time, while his hands reached around me and softly stroked my cock.

I wanted him to stand up and ram his cock deep in my ass, but water is not a great lube. David got up from his knee and pulled me towards him. I twisted around facing him as we kissed deeper and deeper. His cock now back in my hand, rock hard and ready to go. I kissed my way down his chest until I had to get down on my knees to kiss further down, Suddenly I was face to face with his hard cock. I smiled and moaned in pleasures as I slowly slid his cock deep into my mouth. I bobbed back and forth giving him head. I sucked his dick for the better part of five minutes, making sure I was giving him the best blow job I could. My hand slowly touching and caressing my asshole, wanting to finger myself as I sucked his cock.

David was leaning back up against the shower wall as the water struck his body, misting and dripping on my head and face as I just stayed on my knees sucking his cock David was really close to cumming when we heard a female voice yell out;

"Gym closes in five minutes."

I shot up from my knees as David literally pulled himself more upright, twisting his body sideways to hide his hard cock. We both peeked out through the shower curtain, making sure we didn't get caught. What we finally realized is the female employee yelled in from the entrance into the locker room, instead of catching us fucking in the shower. Of course, we didn't get the chance to finish, the nervousness and anxiety of almost being caught ruined the mood. We got dressed and headed out of the gym, hoping the employee didn't say anything to us. Once we were out, we realized, she didn't see us and was just doing her closing routine. We both had a sigh of relief as we made our way home.

When we got back home to David's, we were both still chuckling and slightly nerve racked from being that close to being caught. I was still horny and partially hard as I sure he's still horny too. It was getting late and we decide it time to head to bed. I headed to the bathroom and put on my new floral knee length nightgown with a sexy nude colored thong on underneath.

I lightly spritzed myself with a bit of perfume and put some lip gloss on. I climb into bed and waited for David to get ready. Just as he was climbing into bed, David shut the light off and leaned onto me for a good night kiss. His hand softly caresses my face as we kiss deeply. In my mind I am screaming I need you David and I want to finish sucking his cock and I surely need to cum too. Within seconds of lying there in my new nightgown, with this sexy thong on, my cock was rock hard and I was dying to be fucked. David rolled over and rested up against me, as I wrapped my arm around him. His hand reached out and started rubbing up and down my nightgown. Passing by my hard cock.

"David, I need you," rolled from my lips. David lifted his head as I leaned mine down. Our lips met, softly and gently at first, but becoming more heated and passionate as time went on. I could feel the soft cool satin of my nightgown rubbing up against my skin, my lip gloss spreading onto his lips. David leaned backwards and pulled the lube from the draw. As he returned towards me, he slid his underwear off and started to lube up his hard cock. I knew I was about to get fucked, and as always, I was excited and wanting it.

I watched David stroking his cock getting completely hard and lubed up. "I like seeing you stroke yourself," dribbled from my mouth. David returned to kissing me as his hand rubbed up and down my panties, across my hard cock and balls. I lifted my hips and slid my panties down, raising my nightgown up past my belly button.

David didn't break our kiss as he started to climb on top of me. His lubed fingers made a few quick passes along my asshole just before he grabbed his hard shaft. We adjust angles accordingly and I felt him slide into me. My cock was rock hard, as he began ramming his dick deep inside me. His motion constant at the perfect pace as we lay chest to chest, kissing deeply. "Make love to me David." Rolled from my lips. The night fell quiet as I laid on my back, legs up and pinned to his ribs, the sound of slapping skin and squishy lube sounds filling the air.

I have grown very accustomed to having hm fucking my ass and I love the feeling of his hard dick sliding in and out of me. I wrapped my arms around him, pulling him in closer to me as he slides his cock deep in my ass. I truly feel more and more like a woman every time we make love. Just lying here with my nightgown pulled up after sliding my panties off, his hard cock buried deep inside me, while my shaved legs and painted toenails are up at his side.

David raises himself off my body and is holding himself up by his arms. Our moans emanating in conjunction, the passion intense, the feeling of his cock sliding in and out of me, while his fucking me brings me closer and closer to orgasm. "I love you David," drips from my mouth. David's hand reaches down and grabs my shaft. He slowly holds and strokes me as I lay here taking every inch of his hard throbbing cock, like the little girl I am becoming.

My head was back, my mouth wide open, my arms over my head just being as feminine as I could, enjoying every minute of his cock inside me, while David is stroking me off making me want this forever. I can't get enough of his cock! And now feeling him sliding in and out of me, while being jacked off, is more than I can handle

"David, you're going to make me cum." I blurt out.

"I'm going to cum too," He replies.

David picks up his pace, pumping me harder, faster and deeper as he sends shivers throughout my entire body.

I moan out, "Fuck me baby, fuck me!"

Within seconds, David is pumping me as fast as he can and I hear him moan out as he pushes hard into more one last time. I feel him exploding deep in my ass. Cumming inside me as he should. The excitement of knowing he's cumming in my ass, coupled with his hand wrapped around my cock, brings me to an instant orgasm and I start spurting my cum all over my stomach, screaming in pleasure.

"David, Oh fuck! David!"

My body thrusts and shakes as I release every drop of my cum onto my body, as he releases every bit of his cum inside me.

When we finally finish cumming, David collapsed on top of me. I wrap my arms around him as he rests his head alongside of my face. "I love you," he whispers in my ear.

"I love you to baby." I whisper back.

I fell asleep panty 'less, filled with his cum, sticky from mine, ass tingling, overly fulfilled with him and who I'm becoming. The next morning, David and I finished the shower we started the night before at the gym. He sucked me to orgasm first, followed by me giving him a nice long blow job, which culminated with him ramming his dick in and out of my ass, while I was on my knees on the bathroom floor. It was beyond fun!!

After I left David's and got back home that next afternoon, I invited Amanda over to my place. Her and I spent about 3 hours finding the perfect "little black dress" for me to wear for David on our 1-year anniversary, which was right around the corner. I wanted to be Samantha in full on that night and from then on. There was no going back. I was transitioning and leaving Mike behind as Samantha was coming to life.

To Be Continued...