Mikes First Transgendered Pt. 23

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A story of my on-going transgendered experience.
2.3k words
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Part 24 of the 26 part series

Updated 06/10/2023
Created 10/22/2020
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Mike's On-going gay experiences.

Part 23

Please read parts 1 -- 22, before getting to this.

David Proposes -- The engagement Part 1.

Our eighteenth month anniversary arrived and David and I have been moving along well. David wants to do something special that night, so he makes some calls and plans an evening of dinning followed by a party at the bar with our friends. He makes reservations at the finest restaurant in town, followed by a gathering at one of the gay clubs to celebrate our time together.

For some time now, I have been living as a woman 24/7 and plan to make it permanent. We have researched breast augmentation and hormones because I want tits, but I don't want to lose my ability to get hard and cum. There have only been few occasions I have been back out as Mike instead of Samantha, but if I go through these changes, there will never be a "Mike" ever again. And as far as were concerned, Samantha is where I am headed.

As the day of our party arrives, I want to look special for him. That afternoon I head to the salon and get my nails done, along with a pedicure, my hair done (I had grown it some out by then) and I meet David back at his place, so I can do my make-up and finish getting ready. When it's said and done, I have on a long blue dress, pantyhose, three-inch heels and have styled my own hair, instead of wearing a wig.

We have dinner at Marsalis Steak house. During Dinner, David orders us Champagne. When our glasses come, we toast our anniversary and sip from them. David slides off of his chair and down onto one knee. He reaches into his suit pocket and pulls out a black box, opening it and presenting me with the most beautiful silver diamond engagement ring I have ever seen. David looks at me in the eye and says, "Samantha, will you marry me?"

"Yes." I blurt out.

David's hands shake as he slides the ring up my finger as I well up with tears. A few people in the restaurant had seen this and start applauding, embarrassing us both. David rests his head on my legs and lets out a big sigh. He says, "I was really nervous about asking."

We finish our meal and I can't stop starring at my ring. I never would have thought I would be the bride, but I am absolutely enthralled he asked me.

After dinner we head to the club where a few friends await us. We celebrate our anniversary and our engaging with them. Apparently, they all knew he was going to ask me to marry him, while I was absolutely clueless. I can't stop gloating and showing off my engagement ring as the night flows along. David and I dance softly to songs on the Jukebox as I fall even more in love with him. We kiss romantically all night as we plan build our lives together. When the night finally comes to an end, we decide it's time to head home.

When we got home, I tell David to get undressed and lay on the bed. I have a surprise for him. I go into the bathroom and put on a pair of black crotchless panties, a pair of stay up elastic top thigh highs leaving my high heels on. I cover myself with a sheer black see through lingerie top. I spritz myself with his favorite perfume, put my lips stick on and prepare myself to go and seduce my Finance'.

As I walk out of the bedroom, I see David lying on the bed naked and awaiting my return. My dick and balls sticking out of the crotchless panties, slowly getting hard. As I walk towards him, I am feeling that I am living my dream. I can feel my new ring on my finger and I am so excited to be marrying this wonderful man. Just the thought of him, his dick and this night has made me so horny and so overwhelmed that I need him in me immediately. I plan to spend the rest of my life sucking cock and taking it in the ass and I am okay with that.

As I get to the edge of the bed, David reaches his hand out and lightly caresses my dick and balls. I whisper, "I love you."

David whispers back, "I love you too."

I lean down and kiss him and our passions ignite. I pull from our kiss and whisper; "I want you to fuck me all night leaving these panties on."

David smiles and says, "Ok."

David pulls himself from the bed and stands face to face with me. His dick getting hard as we lean into each other's arms for a deep kiss. I get down onto my knees at the foot of the bed. I look up at David as I reach out to hold his hard shaft. I slowly stroke him back and forth as my mouth waters. Thoughts of being on my knees, sucking his cock and pleasuring him forever spring into my head. This is the man and the dick I'm going to have forever, and I can't wait! I slide David's dick into my mouth and slowly bob back and forth on it. I reach my hand down on occasion and stroke myself as I suck him off. I love sucking his cock and now I will spend the rest of my life sucking him off.

I spend about 5 minutes on my knees, slobbering all over his cock, until David pulls his dick from my mouth and helps me to my feet. He puts me on the bed and whispers, "I want to try something."

He tells me to lay on my back with my head hanging of the edge of the bed and I oblige. I adjust to the position he wants me and I am looking at him from upside down. David leans over me and pushes his cock down to my awaiting mouth. He slides his dick back into my mouth and leans downwards and forward and begins sliding it in and out of my mouth. He is in absolute control as I am pinned down, mouth wide open, with his hard cock sliding in and out of my mouth. David's hips thrusting backwards and forwards coupled with his body weight is jamming his cock deep into my throat. He continues thrusting back and forth at an angle that my throat is wide open and he is sliding his cock deeper into it as he ever has before.

I can barely breathe and feel more like a girl sucking her mans cock than I have to this moment. I am gagging on saliva and his thick mushroom head as he is face fucking me. It feels forced, it feels compromising, it feels dirty and I'm getting harder and hornier by the minute. He is moaning out in pleasure looking down at me while he keeps ramming himself deeper and deeper into my mouth.

My cock is rock hard sticking out of my crotchless panties wailing back and forth. I raise my hips numerous times, wanting to stroke myself. David pulls my head farther down, to where the point I'm about failing off the bed as he gets down onto his knees. He continues slamming his cock in and out of my mouth, hearing my slurping sounds as he moans out, "Yah suck it, Samantha."

I am fucking rock hard my asshole is throbbing and I need cock in my ass. But if my man wants to face fuck me first, then he should face fuck me.

David pumps me for the better part of 5 minutes until I could hear his breath thicken and increase. I am so turned on that I can't contain myself anymore. I needed his cock in me and I needed it now. When David is ready, he pulled his dick from my mouth, as I moaned out to him, "Fuck me baby."

David rolled me over onto my stomach and after a few seconds he slid up behind me. I felt the tip of his cock hit my asshole, just as the cool wetness from the lube accompanied it. He slid his hard cock deep inside me as I moaned in pleasure. "OMG!" I cried out.

My cock was pinned in-between my skin and the sheets, rock hard and ready to explode as David started pumping me. I moan out time and time again as his big thick cock pounded my ass. "Fuck me baby! Yah Fuck me."

I could hear him breathing heavy and getting closer to orgasm and I wanted him to explode inside me, but I need him in my ass for a long time tonight.

David starts moaning, "I'm going to cum. I'm going to cum."

I stop his motion by raising upwards and whispering, "Not yet baby, I need more cock."

David pulls himself from inside me and we both laid down on the bed together. We kiss deeply for a while just letting his orgasm subside, before starting up again. I want him to fuck me and I want him to cum, but tonight I got engaged and I need his cock for more than a few minutes. I really don't care if I get hard again, or if I even cum. I am all woman tonight and plan to have that cock as long as possible.

After lying together for a while and sharing a few smokes, our passions restarted. David climbed back on top of me. He softly and romantically seduced me by sucking on my nipples, running his fingers through my hair and kissing me deeply. We whispered words of love as he started to get fully erect again.

David pushes my legs up to my chest where I grabbed the back of my thighs holding them there. David squirted a generous amount of lube on my asshole and began teasing me with his fingers. He slid one finger inside me, then two, as he fingers fuck me while lying on top of me kissing me. I was moaning aloud in pleasure as his fingers pleasured me. I reached in-between us and stroke myself slowly. David withdrew his hand and slid his cock back inside of me. He feeling of his hard cock, penetrating me thicker and deeper than his fingers, brought shivers to my body. I kept my legs pinned to my chest as David hovers over me pumping my man pussy with his hard throbbing cock.

At one point he was pumping me so hard that my ass was off of the mattress. I was almost staring up at my dick as his dick rammed inside of me.

"Samantha, I love you," spewed from his mouth time and time again.

"Fucking cum in me! Fucking cum in me!" Screamed from mine.

David picked up his pace and the sounds of heavy breathing, slapping skin and a cock being rammed up my ass filled the room. My dick was seconds away from shooting cum as I felt my Fiancé' fucking me harder and harder. "OMG I'm going to cum." I cried out, just as David was thumping me as hard as he could.

"Oh, shit baby. Oh shit." Squealed from my mouth.

I screamed like a little girl as his dick rammed my ass. "David, Holy fuck David, I'm cumming."

I felt the tip of my cock thrusting as my cum started shooting all over my new lingerie, in tandem with David moaning out, "I'm cumming Samantha, I'm cumming."

His pumping coupled with my excitement of knowing he was cumming in my ass sent me into overload, and I started cumming a second time, or at least one hell of a continuation from the first. Shooting out more and more cum, spraying it all over myself.

"OMG David, I fucking love you." I cried out as he kept pounding my ass dropping his load deep inside me.

David stayed inside me for a while longer, just slowly going back and forth, slowly withdrawing his cock and the re-entering my ass. I felt like he was still cumming as his cock continued penetrating me.

David laid his chest down on to mine as I lowered my legs alongside of him. We kissed deeply as his cock rested inside of me. Lube and cum sliding out dripping down onto the sheets.

"I hoped you liked it?" He said.

"I fucking loved it." I replied.

"I am yours forever David" I quietly whispered in his ear. "I'm ready to be all the woman you'll ever need."

When he finally withdrew his cock, I was still trying to catch my breath and want more sex tonight. I needed more sex tonight, I needed him to face fuck me more and cum in my throat. I needed to cum in his ass. I needed it all. I was the bride to be in a homosexual relationship and his dick was all mine. David and I just cuddled a while talking about our future until we both got horny again and fucked some more. This time I swallowed his load, and for only about the third time in our relationship, I fucked him in the ass, shooting my load deep inside him.

When it was finally over that night, we spooned in bed naked telling each other how much we loved each other and couldn't wait for this to be an absolutely permanent. I knew I had to call my friends and family tomorrow to let them know we got engaged. I drifted off starring at my ring, knowing this is where I was supposed to be.

Our morning coffee the next day was beyond belief. I'll tell you all about it in the next chapter.

To Be Continued...

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AnonymousAnonymousover 2 years ago

That was fucking incredible! I came as you and David came. Thank you!

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