Mikes First Transgendered Pt. 16

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A story of my on-going trans & gay experience.
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Part 17 of the 26 part series

Updated 06/10/2023
Created 10/22/2020
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Mike's gay and transgendered experience's part 16.

Please go read 1 -- 15 before reading this one.

Our six-month anniversary and I am in absolute love.

David and I planned a one-night getaway to an antique quaint style town a few hours up the road from where we live. Unfortunately, due to his work schedule and mine, we couldn't get a way for a long weekend. But we didn't want to miss our anniversary day, so we booked a hotel room and on Saturday morning we made our way. We arrived just after lunch time and got situated in our room. The weather was beautiful, so we decide to walk around town looking at the antique stores and mom and pop shops. We each bought a few items eventually making our way back to the hotel late afternoon. We both laid down and took a brief nap, before heading to dinner.

I showered up before him, dressing to the 9's for our anniversary dinner. When David finished getting dressed, we headed to the local prime restaurant for dinner. After we ate a nice romantic dinner, I presented David with his anniversary present. I bought him a nice watch and a couple ties for work. He gave me a nice pair of shoes from his favorite shoe store and a charming bracelet with our names and anniversary date engraved on the underside of it. It was so romantic and thoughtful of him. After dinner we walked around town a bit more, walking hand in hand and just visiting the local shops. What David didn't know was, while he was showering, I had placed a bottle of Champagne and fresh strawberries on ice in our room, so when we got back, we could have a nice romantic drink and feed each other strawberries, before making love.

We returned to the room at about 8:30 P.M., and I surprised him with the Champagne. We sat on the bed, slowly drinking and feeding each other strawberries just being romantic and falling more in love with each other. Our conversations revolved around our future, our fantasies and desires and of course, we were both getting buzzed and horny. David pulled me in for our first kiss of the evening which was a slow, soft and romantic kiss. Our tongues softly and slowly swirled around each other's mouth as we edged in closer. I knew I was in love with him and I wanted to scream it out, but I wasn't sure if he felt the same way or was ready to say it back. David unbuttoned my dress shirt, sliding if off my arms as he kissed his way down my chest. He stopped and softly kissed, sucked and played with my nipples. My dick started to get hard as his hand was rubbing up and down my inner thigh, getting closer and closer to my crotch. My head leaded back and I moaned in pleasure as he continued seducing me.

I unbuttoned and unzipped my dress pants, pulling my partially hard cock out. I needed to be touched. I needed to be stroked off. I needed to be sucked and I needed to cum. David's head slowly dipped further down and he put his mouth around my hard cock. I leaned back a bit feeling his warm mouth, sliding up and down my shaft. "OMG David," I moaned out, as I watched the back of his head bob up and down. David sucked me for a few minutes before I got to the point of needing him.

"David, I need your cock," slipped from my mouth.

David pulled away from sucking my dick and came back up face to face with me. We kissed deeply as my hands rubbed up and down his body over his clothing. My hard cock still sticking up and out of my pants. David's hand reached down grabbing my shaft, making me draw in a long deep breath. I started unbuttoning his dress shirt, pulling him out of it. I reached my hand down and unbuckled his belt, spreading the buckle and belt away from his waist. My hand grasped and grabbed his cock over his pants while we kissed deeply as he kept stroking me off. I managed to get his button open and unzipped his pants, reaching down into his boxers grabbing a hold of his hard shaft. I gasped for air again, as my hand wrapped around his cock. As I pulled from my kiss, I whispered aloud to him, "Oh my god David, I want you."

I started to slide off of the bed as David started pulling his pants down. When I was down on my knees he slid towards the edge of the bed as I helped him slide off his pants. My hands gently rubbed up and down his inner thighs, as I knelt staring at his hard cock sticking straight up, waiting to be played with and sucked off. My cock still sticking out of my pants, hard and throbbing. My ass began to tingle wanting to be penetrated. I leaned my head down as I edged in closer, putting his hard cock deep in my mouth. I moaned through my mouth full of cock happy to have his dick in there. My hands kept rubbing up and down his thighs as my heads bobbed up and down on his cock, making soft, deep slurping sounds. In my head I was thinking, I want to suck this dick every day.

David leaned back on his elbows, watching me sucking his cock, enjoying every minute of this long, slow, wet blowjob. I pulled his cock from my mouth and stroked his shaft, staring into his eyes, thinking to myself; "Tell me what you want me to do to this cock baby." I leaned back down placing his cock back into my mouth. I pulled my pants down further grabbing my shaft and stroking myself and I sucked on his cock. I needed to be played with and I needed to be sucked too. I pulled David's dick from my mouth and stood up. I pulled my pants down and off and told him, "Back up."

David slid himself further back onto the bed. When he laid down on his back, I walked around to the side of the bed and leaned my head down towards his dick, as I got on my knees on the mattress. Just as I put his cock back into my mouth, I lifted my leg and swung my body over him, putting us into a 69. I felt Davis's hands grasping my legs guiding me into the right position. With some adjusting and lowering, I felt David wrap his mouth around my cock, as I continued slurping up and down on his. We laid together sucking each other off for quite a while and I couldn't get enough of the feeling of sucking his cock, while he was sucking mine. His fingers tickled and teased my asshole as his mouth caressed, pleasured and excited ever nerve on my cock. My head kept bobbing up and down on him, trying to bring him to orgasm.

I rammed his cock all the way down my throat, holding it deep inside me as I heard him moan through the blow job, he was giving me. To make it more pleasurable for him, I would then slide my mouth all the way up his shaft slowly to the tip of my lips, swirling my tongue around it while it was just inside my mouth. Pulling him out occasionally to stroke his shaft, moaning dirty statements like, "David I want you to cum in my mouth."

David picked up his pace on my shaft, as I continued sucking him. The only sounds in the room were light moaning from both of us, coupled with the sounds of wo blow jobs going on at one. David's cock was hard as a rock and his hips starting thrusting up and down, a sure sign he was close to cumming.

I pulled his cock from my mouth and told him, "Fucking cum baby, I want your cum."

When I put him back into my mouth, David started thrusting harder and harder upwards with his hips, as he was on the verge of blowing his load. My cock was rock fucking hard and I wasn't too far away from cumming as well. David's moans got louder and louder and he started whimpering. I felt his cock start cumming in my mouth. His warm soft, sticky load, swirling around my mouth and down my throat. After I swallowed down every drop, I pulled his cock from my mouth and was holding it in my hand. The excitement of him still sucking my cock after I made him cum, brought me to an instant orgasm. "David, Holy Fuck," I screamed out, just as I started cumming. I put his dick back in my mouth sucking it little a pacifier, while my cum shot deep into his throat. David and I kept each other's cock in our mouths for about two more minutes after cumming, just making sure we each got every drop.

When it was over, I slowly climbed off of him, swinging myself around. I leaned down face to face with him, kissing his lips softly. Our mouths eventually parted and our tongues swirled around each other's mouths, tasting each other's cum. I laid down next to David, lying just off of his left side partially on his arm and chest. David and I laid around naked, finishing our Champagne and just enjoying naked time together.

After a long while David got up and brushed his teeth, getting himself ready for bed. I got partially dressed and ran outside of the last smoke of the night. When I got back, I freshened up and climbed into bed next to him. Just before I climbed into bed, I placed David's anniversary bracelet on my wrist, falling asleep wearing only that. And happy to be wearing only that. We fell asleep pretty quickly, naked and comfortable from our blow jobs and cumming.

About 2:00 A.M. I felt David roll over and wrap his arm around me. He snuggled up behind me and suddenly I was the little spoon. I wrapped my arms over his and pulled him in closer as we tried to fall back to sleep. David began kissing the back of my neck softly and seductively. I got excited that he was cuddling with me and maybe trying to be romantic and loving and I was happy he was lying next to me. David got up and went to the bathroom to pee. As he returned, I heard him fumbling around by his suitcase. I figured he was getting something to wear, since we were both still naked. A short time late he climbed into bed and cuddled right up behind me again.

David continued softly kissing my neck and shoulder area, as his hands began rubbing all over my arms and chest. He whispered, "I want you now."

"Are you still horny honey?" I asked him.

I felt his nose rub against my neck as he whispered, "Yes. I am always horny for you."

My heart melted, because at least I knew he wanted me there and enjoyed sex with me.

I heard the top of the lube bottle pop open and within a second David's hand slid in-between my ass cheeks. The cold lube, sliding over and up and down my asshole sent hormonal feelings deep inside me. I knew he was going to fuck me in the ass and my stomach was doing flips waiting for it. I lifted my leg slightly and moaned as he fingers rubbed and caressed my asshole. David's hand pulled away as I reached back and behind me, finding his hard cock, bulging and standing straight upwards. I pulled on his shaft as he was fumbling with the condom wrapper. When he finished sliding it on, he pushed his hips forward as I adjusted slightly trying to line up his cock to my asshole. I felt his hard cock, hit my asshole, he tried pushing into me a few times, missing getting it in.

I said, "Lets just do it this way."

I rolled onto my back and grabbed the pillow from under my head, lifting my hips up and sliding the pillow under my lower back / the top of my ass crack. David got onto his knees and in between my legs. I lifted my legs up as his body leaned in. His hand grabbing his shaft lining up his hard cock with my asshole. I pulled my legs closer into my chest giving him better access. With one giant push David slid his cock into me, almost hurting me, because I hadn't been fingered and the condom wasn't lubed, but I was ok with it. David slowly started sliding his hips back and forth pushing into me further and deeper. I moaned in pleasure as I felt his hard cock, getting deeper and deeper into me. "Softly baby, just like that." I whispered out.

David was holding his body up by his arms, as I grabbed and stroked my cock, I wasn't hard, and to be honest, I didn't care. I was being fucked, pleasured anally by him, who was fucking me like a man should. So, if I didn't get hard or cum, wasn't a concern for me at that moment. After a while of his cock lovingly sliding in and out of me, kissing me deeply, he let his body down on top of mine and pressed against me, skin to skin. I felt like a true woman being made love to, while her man was sliding his cock in and out of her wet pussy. But in this case, his hard cock sliding deep in and out of my tight ass.

"OMG David, you feel amazing." Spewed from my mouth.

After making love to me face to face and chest to chest for a few minutes, David raised himself back up onto his arms and hands hovering over me as I spread my legs open and upwards wide open for his hips to push deeper into me. I reached down again with my left hand and started playing with my limp cock again. But, the feeling of having my ass banged was more erotic and carnal than being hard, so I decided I didn't want to cum. I just wanted to lie here and get fucked making sure he got off. I put both of my hands on the outsides of David's arms, as he was holding himself up by them, slamming his cock in and out of me.

"Yah baby, fuck me..... Auuughhh... Yah.... David fuck me." Spewed from my mouth.

His cock felt so big and so thick sliding in and out of my tight ass as I laid there in this dark hotel room, in the middle of the night; on our 6-month anniversary, being fucked, taking every inch of him. "Yah fuck my ass baby, fuck your pussy," Slipped from my mouth.

As I laid here being banged, I wondered if I would cum with a soft cock. I was curious to know if I could cum on my back without touching myself. Because a few times when he's fucked me doggie styled, I've cum hard without too much self-pleasuring. David was moaning and breathing heavy, as the sound of slapping skin filled the room. The mattress squeaking and popping as he continued pounding my ass. "David, cum in your ass baby." Slipped from my mouth, as he continued diving his cock deep inside me.

"Whose ass is this?" He asked.

"It's your ass!" I squealed out.

"Yes, it is!" He grunted.

"It's all your ass David. ALL YOURS!"

David began pounding me harder groaning out, "Whose cock is fucking your ass?" He asked.

"Your cock baby, your cock.!" I squealed out...

"Yes, it is!" He replied.

"You like this cock deep in your ass?" He asked.

"OMG David! Yes, I love your cock in my ass!" I replied.

"Your cock is perfect David; I love it up my ass! I furthered.

I was answering his question, but I was also screaming in my head; I love you David, I fucking love you.

My head was tilted back, my mouth wide open full of drool, my legs now wide-open feeling the pleasures of his cock deep in my ass. OMG David! All the dirty talk, started to get me hard and sent tingles throughout my body. I started moaning out again and again, "YES, FUCK ME BABY! FUCK ME."

David was pumping me as hard and as fast as he could. I moved my legs from wide open up towards the sides of his ribs. After a while of them being along his sides, David pinned my legs to my chest holding them down with his hands under my thighs, my partially hard cock hid between my legs, while being pleasured by his throbbing cock diving deep in and out of me. I wanted to scream I love you David. More importantly I wanted his to scream it to me.

"Mike I'm going to cum, I'm going to cum!" Bolted from his mouth.

"Yeah, cum in my ass baby, cum in it." I bellowed back.

David picked up his pace and started ramming his cock in and out of me for about another minute. My focus turned back to him, eye to eye contact with me screaming out in pleasure as I squeezed the exterior of his arms. His hips thrust his cock deep inside me. "HOLY FUCK DAVID!" I screamed out, coupled my quick hard whimpers and quips of, "Oh God, Oh God" crying out from my lips as he banged my ass. Just about a minute later, David's body started quivering and he moaned aloud, "I'm fucking cumming," as he blasted his load deep inside me. His motion still pumping back and forth but slowing as he ejaculated deep into the condom, deep in my ass.

My asshole wide open, my cock tingling, but not cumming, my heart racing and my legs shaking as I lay here in the dark. I thought to myself, I could do this the rest of my life. His cock is perfect. The way he fucks me is perfect, and the more cock I get the further I get away from women and the more I want to be a girl. "OMG David your amazing," I moaned out.

David still had his cock buried deep inside me as his body fell on top of me and we kissed deeply as the last bit of his orgasm, drifted away. Our tongues swirled around each other's mouth. I wasn't even hard and I didn't cum, but didn't even want to. I was loving every bit of lying here getting fucked hard, pleasing my man's needs, without even worrying about myself. David pulled from our kissing his head down onto my chest, his cock still deep inside me, as my legs wrapped around his waist.

"That was incredible." I spoke.

David catching his breath said, "Yes it was."

When he finally slid his cock out of me, I felt lube sliding out of my asshole, like cum would drip out of me. David and I fell asleep again, naked and cuddled in this dark hotel room, after having a wonderful round 2 of sex. I felt more and more like a true woman, letting my man pound my ass until he came deep inside me. There was no doubt I was going to be getting fucked for a long time to come. I knew I wanted it. I knew I needed it and I knew I loved it!

The next morning after breakfast, we ended up showering together before we checked out and headed home. After washing each other and ourselves, David spun me around and bent me over at the waist. He started eating my ass out for a few minutes in the shower. I thought he was going to slide up behind me and fuck my ass hard again. I wanted him to, I didn't even care if he had a condom on or not, I just wanted his cock inside me again. But sadly, he didn't. By the end of our shower, he had given me a blow job and I gave him one, until we both came again swallowing each other down.

On the way home, I wore my new shoes and bracelet and was so happy we spent our six-month anniversary here, alone and naked.

The next few months saw several few weeks, where we were unable to see each other, due to scheduling. But we got through it and continued our relationship without too many bumps in the road. By the time we finally got back on track and could really spend time together as often as we wanted it was almost 8 months in. That's when we finally said I love you to each other and moved our relationship forward.

I'll tell you all about that night in the next chapter.

To Be Continued...


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