Mikes First Transgendered Pt. 19

Mike's On-going gay experiences.

Part 19

Please read 1 -- 18 before going reading this one.

Our 1-year anniversary and Samantha is almost complete.

David made reservations for us at a seafood / steakhouse in town for our 1-year anniversary. I believe he thought I was going to go as Mike, since I have never been out of the house dressed as Samantha. But he was in for a real surprise.

That afternoon, Amanda and I went to her favorite salon where I bought a new wig, long, blonde and flowing, almost the exact matching color to my hair. The stylist styled it and got it ready as I got a pedicure. When Amanda and I returned to my place, she provided me with a set of press on nails, painted them to match my toes and did my make-up. I couldn't tell you how surprisingly aroused I was walking around half naked in front of her as we gathered my dress and matching accessories. Amanda was wearing low cut shirt and I was staring at her tits constantly. In some ways because I was jealous, she had tits, and in another because, I wanted to pull them out and play with them. Even though I was in the midst of transitioning, I still had male urges and still found some women desirable.

When we had everything ready, we headed over to David's. He wasn't allowed to see me as I finished getting ready in his bedroom. Amanda touched up my make-up and I put on some jewelry so I could be all the woman I could be. When it was all done, I was wearing a knee length tight black dress that had a low-cut V-shaped front. My bra filled with my breast forms. I had a throw shawl over my shoulders, with my long blonde wig / hair flowing. I had on a pair of thigh high black pantyhose, a matching black thong and two-inch heels. Amanda gave the drum roll to David who was sitting in the front room waiting for me. His jaw dropped when he saw me in full dress, with make -up, the wig, the heels and the shawl all ready to head out as Samantha, not as mike. I think his heart skipped a beat.

"You look absolutely amazing!" He mumbled out.

He walked over to me and grabbed my hand noticing my long-painted nails. He kissed my hand and said, "Samantha, you are incredible."

I know he was truly shocked. I think is his mind, Amanda was over to help me out with the "after dinner attire," not making me up the way she did.

"You're ready to go out as Samantha?" He asked.

And as scared and nervous as I was, I replied back; "Yes, I am baby."

As sexy as I looked and as sexy as I felt, I was petrified to go out anywhere dressed as a woman, but tonight was going to be the first step of the rest of my life. As David and I left as Amanda shut the door behind us. She had to gather her stuff before heading out. David walked me to the elevator and he was in absolute awe of my appearance and my lady like mannerism. When we got to the front door of his building I stopped for a few seconds and took a deep breath. I looked at the outside world I was about to enter into. David paused and just waited without saying a word, knowing I was about to embark on a new chapter of my life, because once I stepped outside of those doors into the open world, I was going out as Samantha.

After a few seconds, I mustered the courage and walked out of the building into my new life. We walked through the parking lot to his car and he opened the car door for me like a gentleman should. As we drove, we held hands and talked about the outfit I had on. There was no doubt I was nervous and anxious about the night, but I have to tell you, Amanda did such a great job on my make-up and with the wig and shawl, that I barely recognized myself.

We arrived at the restaurant and were seated almost immediately. At first the waitress called me Ma'am, but I think she realized a bit into it that I was a man in a dress. But I didn't care. I had a lot of people staring at me throughout our dinner and I don't know if they were starring because we were both "overdressed" for this type of steakhouse, if they thought I was smoking hot, or if they knew I had a dick. Either way I was out as Samantha and was loving the attention.

After dinner David and I went down to one of the city's gay clubs, that we would hang-out at time to time. We sat with a few friends, including Amanda who was there to help us celebrate our one-year anniversary. David and I slow danced to a few songs and kissed in front of everyone. I was ready for him to propose. I was truly hoping it would happen, but that night he didn't. Later in our lives together he did, but not at our one-year anniversary. I even danced with Amanda a few times, as well as a few of the gay guys that hang out at the club. It was a great night. I never felt so free and unincumbered dressed as Samantha. I even went to the woman's bathroom. P.S. that was weird...

David and I had several drinks throughout the night, but never got drunk. We knew we still had a private party to attend, back at his place. And to be honest dressed in full regalia (as I liked to call it) was a huge turn on for me. I was the center of attention that night and couldn't wait to be the center of attention for him back home. As we drove home David and I held hands and just talked about the last year of our lives, how things have changed. The friends we associate with, how Amanda helped me more than anything or anyone in the world. We spoke of things to come. Things we wanted to do together and we spoke of our love.

When we arrived home, David had the house all set. I discovered that one of the reasons Amanda didn't leave right away as we left for dinner, was as much as she was helping me get ready for the night, she was also helping David. After we left, she placed two dozen red roses on both sides of the bed. She had spread rose pedals on the bed, and had Champagne chilling with two beautiful wine glasses that were etched with the writing David and Samantha. David dimmed the lights in our room and turned on soft romantic music. We danced again for a while, just talking and holding each other. It was (at that point) the most romantic night I had ever spent with someone.

As the night progressed, David started to seduce me. But not me -- as in the old me -- but he started seducing Samantha and I was puddy in his hands. The feeling of my breast forms pressed up against his chest, the lipstick on my lips, transferring over to his. My hair having to be moved out of the way for him to kiss my neck and the fact that with my new two-inch heels on, I was actually just about a ¼ inch taller than he was. Which was rather cute. But the whole night, with the dress and pantyhose, heels and make-up, the dinner, the friends, the bar and now us alone at home was so stimulating, so erotic and so fulfilling.

David guided me down onto the bed and we kissed deeply. His hands rubbing up and down the front of my dress, touching my breasts, as I cupped his face. The smell of his cologne - the one that attracted me to him in the first place -- lightly scenting from his neck. His hands touching me everywhere, sliding up and down my pantyhose, along my thighs, along my ass cheeks. David's hand rubbing on my crotch feeling my cock over my panties, was such a turn on.

I could feel the little strap of material from the thong nestled between my ass cheeks as he rubbed back and forth. My asshole was already wide open and awaiting his hard cock. David sat me up and unzipped the back of my dress. I pulled my arms through and let it fall to my waist. He unbuttoned his dress shirt, removing it from his body. He slid off the edge of the bed and got down on his knees. I lifted my hips slightly as he pulled the dress off of me the rest of the way. I sat in the oblique light of his room, in my bra, panties, pantyhose and heels. David rubbed up and down my legs and kissed my inner thighs. As my hand rested on the back of his head. David stopped at one point and looked up at me and said, "Samantha, I absolutely love you."

My heart just melted as he knelt in front of me, admiring at how beautiful I was. David stood up and unbuttoned and unzipped his pants. He slid then down and off, followed by his boxers. He stood in front of me naked, partially hard and sexy as shit. Driving me crazy. My hand reached between my legs rubbing my bulge as I just stared at his naked body. David returned to his knees and kissed his was up my legs from my knees to my crotch. He kissed over my panties while looking up at me, making deep eye contact. His hands reached at the sides of my hips and he grabbed my panties hinting for me to lift my ass off the mattress. David looked at me and whispered, "You are a beautiful woman, Samantha," as he slowly pulled my panties off. My cock popped free as he nestled my panties down my legs.

Holy Fuck, rang out in my head. He is sliding my panties off while calling me Samantha!!! I sat staring deeply into his eyes as I softly and slowly stroked my cock. "David, I love you." Sprang from my lips.

I leaned back onto my elbows as his head dipped down. His mouth wrapping around my hard cock. David slid his mouth up and down and back and forth, sucking my cock. I moaned out in pleasure as he gave me head. After a few minutes David pulled my cock from his mouth and pushed my legs up a bit, so my feet would rest on the edge of the mattress. He dipped back down and put both of my balls in his mouth. He sat there making eye contact with me, while I felt his tongue swirling around my nuts, as my hard cock stuck straight up in the air. David released my balls, dipped his head down further and began eating my ass out.

He pushed my legs up in the air towards my chest, as his tongue swirled around and up and down my asshole. I am in absolute heaven while being eaten out, I only wish (at times) I had a dripping soaking wet pussy for him to lick, stick his dick in and cum in.

As much as he's pleasuring me, I can't take the teasing anymore. I need his cock inside me and I need it in me now. I pulled David from my asshole and helped him back up onto his feet as I leaned forward. I grabbed a hold of his hard shaft as he stepped closer towards me. I slid his cock into my mouth, making sure I swallow every inch of it deep into my throat, as I start bobbing back and forth. I was sucking so hard, that I thought I might suck it right off his body. I want it so bad! I need it so bad! and I only wished (at that second) that he was 3 inches longer and 2 inches thicker, so I would literally die from suffocation with his cock down my throat. Let alone feeling him ripping me apart as he fucks my tight ass.

After about two minutes of sucking his cock as hard and deep as I can, I pulled his cock from my mouth and whisper, "David, fuck me!"

I raised my hands grabbing his arms and pulled him down on top of me as I laid back onto the mattress flat on my back. David started to lean towards his nightstand to get the lube. I stop him mid reach. "No". I said. "I'm wide open and ready for you. You won't need that tonight."

David leans back on top of me as I began lifting my legs up. With one fluid motion, he pushed down towards me as my legs are lifting up and he slid right into me. The spit from my mouth on his shaft, along with the saliva on my asshole from being eaten out, accompanied by my wide-open ass was lube enough for him to slide right it. "HOLY FUCK," I moan out. As he begins shifting forwards and backwards.

"Samantha, I love you." Spews from his mouth.

David starts pumping my ass as he has done so many times before. But tonight, was different. I was all the woman he asked me to be. I was fully dressed for him. I was being fucked while wearing my bra, with breast form tits in it, my thigh high panty hose and my heels still on completing the ensemble. Tonight, I was complete Samantha! Completely a woman! I had made the change.

I wanted to please him. I wanted him to want me even more. I was ready to transform. I was ready to become a woman. I was ready to be his wife. I was ready for surgeries, for hormones, to suck cock the rest of my life. I wanted his cock all night, I wanted to be all the woman he'd ever need. I wanted it all. I wanted his dick forever. I wanted him to fuck me harder. Fuck me faster. I wanted it deeper and longer. I wanted everything.

"Fucking harder David. Fuck me Harder!" Bellows from my mouth.

"Fuck me like I should be fucked. Like you wanna fuck me. Fuck me like your woman!"

"Fuck me baby."

I was literally trying to push my ass downwards as he thrusting in and out of me. I want him to cum. I need to feel him explode deep inside me. I want to fucking cum while his cocks buried deep inside me; and I never want him to stop pounding my ass. I figured with the excitement level we were both at and the pace he is ramming his cock in and out of me, it wouldn't be long until he came. But tonight, I was way off. Without breaking stride, David rolled me on top of him. His dick popped out for a second, but since we have done this so many times, I knew exactly where to be and without my hands for assistance, I sild his cock back inside me.

"Oh my god," I moaned out as I started bouncing up and down on his dick.

My cock was flapping up and down as the bed squeaked and the moans and groans got louder. There was no doubt I wanted to be fucking like this all-night. I rode David for about 10 minutes, leaning back a lot of times, looking down at my legs covered with pantyhose, my hands grasping the heels of my high heels as I moaned out in pleasure. Grabbing and cupping my bra with the breast forms, holding them, caressing them like they were real tits, moaning out, "OMG, I want real tits,"

I bellowed out to him as his cock kept ramming deep in my ass, "David, I want this forever. Your cock is perfect." Just as I leaned down to kiss him, David whispered out, "I'm getting close."

I rolled off of him and pulled him back on top of me. "Fucking fuck my ass baby," spewed from my mouth. David pushed my legs up to my chest as he slid his throbbing cock back inside me.

"Oh fuck!" I moaned out as he began pumping me again.

Light moans of Oh's and Ah's squeaked from my lips as his body weight pushed my legs closer into my body. "I'm going to cum, I'm going to cum!" He whimpered out.

"Cum on my face baby!" I replied.

David pumped me hard and fast for about another 15 seconds. He pulled his dick from my ass leaned up over me. He started stroking himself as I lay under him, my mouth wide open, tongue sticking out. Within a few strokes, David started shooting his cum all over my face, mouth and neck. I was trying to catch it all as he was squirting, but he was shooting it everywhere. My hand pulling on my cock the whole time. Just as I was swallowing what I had caught down my throat, David reached down and rammed two fingers up into my ass and I screamed like a little girl. He started finger fucking me as I was jacking off. "HOLY SHIT," I moaned out as my stomach tightened and my legs lifted upwards. Within seconds I started blasting my load all over my stomach and chest as his fingers kept sliding in and out of me.

"David, fuuucccckkkkkk!" Strewed from my mouth. "Don't stop." I begged. "Don't stop."

I pulled David back on top of me and I reached down grabbing his cock. Stroking him hard to keep him hard. "David, I need more. I need you more."

David slid himself right back into my wide-open ass and continued pumping me slowly as we kissed deeply. Eventually we started to dry out, so he reached over to the night table and grabbed some lube. He squirted a bit at the bottom of my balls and I felt the cool lube running down in-between my ass cheeks until I felt his cock all lubed up. David and I laid chest to chest slowly making love. I couldn't get enough of his dick. I felt the cum he squirted along the side of my face and in my hair, on my chest. My cum all over my stomach getting cold and running down my sides.

"David fuck me from behind," I begged.

As he I got up and was getting situated, I got on my knees with my ass away from him. I felt a generous amount of lube hit my asshole again as he climbed in behind me. A second later his cock slid deep inside me again. David grabbed both of my hips and started thrusting as deep and as hard as he could.

"Oh David, Oh God David. Yes, just like that. Yes."

Sensations were running through my body like never before. My cock became rock hard again as my balls were swaying back and forth as he continued slamming my ass. I was face down on a pillow, my hands buried deep inside my bra, pulling and twisting my nipples as I knelt getting my ass ponded by the man I love. "Ugh David, Ugh, I can't get enough. Ugh, Ugh, Ugh..."

"David holy fuck baby! Holy fuck! I need you to cum in me."

David continued pumping me for what seemed like an hour, just driving his dick home. Fuck me, kept spewing from my mouth. I wasn't going to touch myself. I didn't want to bring myself to a second orgasm, before he was ready to cum. I wanted my cock to start shooting cum from being ass fucked from behind and not from being stroked off. And as long as he was still going, I was still going to keep taking it and not cum. But a soon as I was thinking that, he was hitting a spot deep inside me bringing me closer and closer to cumming.

"David, I'm going to fucking cum. I'm going to cum," spewed from my mouth. Just seconds before I started shooting my load all over the bed. I screamed in pleasure as his big cock kept pounding my ass. David, don't stop! Don't fucking stop!"

And believe me he didn't. He just kept ramming his long hard cock in and out of me. Deeper and deeper and faster and faster. I reached down and grabbed and pulled on my balls. The feeling of this night, the transition, the desire to be a woman made me want this forever. I needed a cock in my mouth. I need a mouth on my cock, and I needed a bigger dick in my ass. David pumped me for about 1 more minute this way, until --- believe it or not --- I came again. I had never cum back-to-back times while being ass fucked. But tonight, he managed to make me do it. Seconds later his groaning got louder and louder and I felt him blow his load deep in my ass. "Samantha!" He cried out as he was cumming inside me.

When David finally pulled out of me, my ass was as wide as could be. I would have bet you he could have slid his whole hand inside me and fist fucked me for another half hour until I shot a third load. David and I laid down together, just cuddled whishing each other a happy anniversary. I don't know if it was the alcohol, or me dressed as Samantha, or just the night in itself, but It was the best sex we ever had. The longest sex we ever had and the most erotic sex we ever had.

We both feel asleep quickly and I awoke before day daybreak. I just laid there next to him pondering my future. What I wanted, what I believed in and where I hoped we were going. I was ready to make the change. I now had been out in the world as Samantha. I had broken new ground. I had just stepped out and away from the "sneaking around" dressed; the "part-time" dressing. I was out. And was going to be out permanently from here on out. I couldn't have been happier.

I never went back to wearing boy clothes again after that night. I lived from that moment on as Samantha. No matter where we went, no matter what we did, no matter the event, occasion or just a quiet night at home, I was always dressed as a woman. Of course, when I walked into work on Monday dressed in women's clothes It was an awkward situation. Sometime later I was fired from my job at the "BIG COFFEE HOUSE", even though they "allegedly" have very liberal views, because I wasn't a product of creativity and I was "late" a few times. I spent a few weeks unemployed, but found work again.

I lived and breathed from that moment on as Samantha and I was never going back. The next 11 months went by quickly and we had some fun times. Some erotic sexual experiences and .... Things I'll tell you all about in the next few chapters. But for now, let's just say, Walter joins us.