Mikes First Transgendered Pt. 21

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A story of my on-going transgendered experience.
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Part 22 of the 26 part series

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

Part 21

Please read parts 1 -- 20, before getting to this.

Our second night with Walter.

A few weeks after our night together, Walter calls David and tells him he needs a night out. Both David and I are off Saturday night, so we all decide to go to the gay bars downtown. Walter arrives at our place just as I am finishing getting ready. Tonight, I am dressed to the nines. I am wearing a knee-high black skirt, a dark colored women dress blouse, my black thigh high panty hose, 3-inch stiletto heels, a short brown wig and have a beautiful set of nails on. I am so excited to get out, see some friends and be the woman, I was meant to be.

David drives to the bar. I sit in the passenger seat and Walter's in the back. We arrive and head into the first club. It is crowded, but we find a table and order. There is a lot of transgendered and crossdressers in the bar, so I feel right at home. After a few drinks we decide to walk down the street to another club, where our usual crowd is at. We see a few friends and join them at their table. We all polish off a few drinks while playing pool and listening to the Juke Box. As the night progresses, I have one too many drinks. I am horny as hell from being dressed up and even hornier with the alcohol running through me. David excuses himself and heads to the bathroom. I figure this is my chance. I excuse myself telling everyone, "I'll be right back."

I follow David into the bathroom. After he finishes up, I grab him by the tie he's wearing and gently pull him into a stall.

David Asks, "What are you doing?"

"A surprise!" I reply.

I sit down on the toilet, mumbling the words, "I want you cock now."

David is almost embarrassed and trying to stop me from unzippering his pants, but I am horny, persistent and I need to suck cock. I manage to get his zipper open and reach my hand into his boxers. David's dick is soft, but I slowly stroke it looking deep into his eyes. I know he doesn't want to do this here, but I need it. As I gently stroke sand arouse him, I feel him start getting harder.

David says, "Samantha, you're crazy, what if someone catches us?"

"Then they catch us," I reply.

I pull David's almost erect cock through the hole in his boxers and lean down. I slide his cock deep into my mouth, my head motions back and forth as I feel his cock getting harder and harder with each passing moment. Davis's head drops back and he is moaning in pleasure as I take him deep into my throat. I slide my hand up in between my legs rubbing up and down my inner thigh, feeling the sheer sexiness of these pantyhose, winding my way up to my fully erect cock. I can feel the silkiness of my panties as I softly rub my cock over the panties, making myself harder than before. I continue sliding his cock in and out of my mouth as David moans out;

"Samantha, not here. We're in public and Walter is waiting.

Knowing he's right, I let David back away from me as he puts his dick back into his boxers and zips his pants up.

David walks out of the bathroom ahead of me as I sat on the edge of the toilet rather bummed that I didn't get to finish sucking him off and I didn't get to cum. Lately there has been an overactive drive and desire for me to cum, whether it be by getting head, or being fucked, but more importantly I have such a desire to shoot y load into someone.

I sit back and just fantasized deep in my head about touching someone and someone touching me. I rub my hands all up and down my legs feeling the sexiness of my pantyhose, my fresh shaven sexy legs, just wishing I was on all fours, naked with a cock buried deep inside me. I pulled my cock from inside my panties and slowly stroke myself. My dick, which has become un-important part of our sex life, is missing someone taking care of it. I was thinking about all my past experiences. Being inside my old girlfriends, Sara and Ina and I was missing the feeling of being inside someone. I was deep in thought and stroking myself at a good pace, when I was interrupted by someone coming in the bathroom. I was probably 10 seconds away from cumming and I wanted to just kept stroking off. But I let the erotic desires go, composed myself and head back into the bar.

We sit at our table for a while longer, having a few drinks and just enjoying the night. But I must say, I could not focus on anything but their cocks. I wanted them both to blow me. I wanted both of their dicks in my ass. I wanted either of them, right now. I was having flash backs of the last time the three of us were together and how I felt sucking one, while being fucked by the other. I needed them both tonight and I was planning on getting them.

After we finished our round of drinks, David and Walter walked back over to the bar to order more. They were standing with their backs to me, shoulder to shoulder awaiting the barkeep. I decide it's time to take this party back to David's. I walked up behind them both, placing my arms around their shoulders. I pulled their heads a little closer to me and whispered, so they both can hear me; "When are you boys going to take me home and fuck me?"

Both David and Walter get a look of shock and surprise on their faces. They both looked at each other around my face and kind of nodded in agreement.

David yells out, "Bill please!"

David turns his attention to me, looks me in the eye and asks, "Are you sure?"

"Yes, I'm sure. I reply. "Let's go home."

We left the bar and start driving home. On the ride home I am trying to decide whose cock I want first? Should I suck Walter off as David fucks my tight ass, or let Walter try anal sex, while I blow David.

When we get back inside David's apartment, I could not control my urges and more. I walked both of them over to the couch standing them face to face. I tell them, "You guys kiss while I take care of everything else."

David and Walter start kissing passionately as I stood and watched. It didn't take me long to start getting hard again and I really need both of their cocks. I unbutton and slide out of my shirt, unzip and slid my skirt down. I am standing there in my bra and panties with my pantyhose and heels on, rock hard watching these two men make out. I drop to my knees and place myself in-between them. I start rubbing on both of their crotches as I smile from ear to ear. Two cocks tonight, what else can a sissy crossdresser ask for???

I unbuckle Walters belt then David's. I unbutton and unzip both of their pants letting them fall to the floor. Both Walter and David kick out of their pants and are still standing over me kissing. I can see both guys are hard and ready for action. I pull down Walter's underwear, then David's letting both of their hard cock's spring free. Since I have given David numerous amounts of blow jobs, I decide to start with Walter. I slide his hard cock into my mouth and slowly start bobbing back and forth on his shaft. I take a free hand and grasp David's cock slowly stroking it. After a while I switch over and slide David's cock in my mouth and stroke Walter. My cock is bulging in my panties and I need cock in me. David and Walter break from their kiss and David says, "I'll be right back."

I stand up and kiss Walter for the first time letting our tongues swirl around each other's mouth. I gently walk him backwards with a seductive look, easing him down onto the couch. I get down onto my knees in between his legs and stare at his hard throbbing cock. I lean in forward, placing him back in my mouth and start sucking up and down on his shaft. I hear David come back from around the corner. I look in his direction and he has a bottle of lube in his hand.

I pull Walter's cock from my mouth and ask him, "Do you want to try sucking dick."

Walter nods his head yes. I tell David, "Let Walter suck your dick."

David gets onto the couch leaning over Walter. I see Walter open his mouth and slide David's cock inside. He slides back and forth or a bit as I watch him giving David head. My hand slowly stroking up and down his cock as I watch him pleasure my boyfriend. Walter pulls away after a bit with an odd look on his face. He says, "I just can't do it. Sorry."

"It's okay" I say. "Just sit back and enjoy."

I bow my head down again and place Walter's hard cock back in my mouth. David slides off of the couch and kneels in behind me and I feel him slide my panties down to the back of my knees. I feel the cold wetness of the lube hit my asshole and I moan in pleasure. Oh, My Fucking God, I am about to be ass fucked while sucking cock. My cock gets even harder then before. I feel David put the tip of his hard cock at my asshole as he pushes in and slides inside me. I gasp for air as he pushes himself all the way in. I begin moaning through the blow job I am giving Walter. David starts quickening his pace as my dick falls limp. My mouth trying to keep up with the pace of David's dick fucking my ass. My head bobs up and down Walters hard cock tasting every bit if his pre-cum as David continues railing me from behind.

In my heart and my mind I was thinking, THIS IS A FUCKING DREAM COME TRUE. A cock in my mouth and one in my ass! Holy Fuck!!!

Walter is getting closer and closer to orgasm as I suck up and down his shaft. His breathing increases and his hands are on the back of my head lightly guiding me up and down. David's dick ramming in and out of my ass, deeper with ever push, bringing himself closer to cumming. Walter starts moaning more and his hips start thrusting up and down. Within seconds I feel his sticky hot cum shooting into my mouth. I keep sucking taking every drop of his cum, while David pumps me harder and harder. I sit with Walter's cock in my mouth moaning in pleasure as David is thrusting me deeper and deeper. I can't get enough and I want more. I want to be fucked all night. I want more cock. I want more cum. I want Walter to fuck me in the ass too.

I finally withdrawal Walters cock from my mouth and just lay my head down on his legs as David continues pounding my ass. Walter watches David just fuck me hard for the better part of 8 minutes His cock slamming in and out of me bringing me the sexual pleasure I desire. I want him to cum so bad, but I can't get enough of his dick deep inside me. I think Walter's enjoying seeing me get pounded. Walter is slowing stroking my head and face as I am fucked like a little slut. I hear David start moaning deeper and deeper and I know he's getting close. I whimper out, "Fuck me baby, cum in my ass."

My head lies softy on Walter's lap with my mouth wide open, moaning in deep pleasure and pain as David pumps a few more times deeper and deeper. I lift my head putting Walter's cock back into my mouth. I need something to suck on as David pounds my ass. I start bobbing up and down again as David continues pumping me faster and faster. I hear David moaning louder and louder and I know he's about to cum. I am so fucking excited to have a dick in my mouth as my boyfriend is about to cum in my ass.

With a low moaning groan, I feel David push deep inside me as he starts cumming in my ass. I feel his cock pulsating inside me and I know he is blasting my ass full of sperm. "OMG." I mouth out with Walter's dick still in my mouth.

David slows his pace and continues sliding in and out of me slowly until he finally withdrawals. My legs quiver and my ass numb from the punishing I just took. Walter sitting naked on the couch, holding my head as my body quivers.

We all hung out for a bit sitting around half naked until Walter had to leave. I could not believe the night we just had, I swallowed Walter's cum and David blasted my as full of cum. It couldn't have gotten any better.

But it wasn't over yet!

Remember I hadn't cum yet. I had sucked both of their cocks, swallowed Walter down and taken David anally. Now it was my turn.

As David and I crawled into bed, I started to seduce him again. I was instantly hard and wanting to cum all over the place. I begged David to let me fuck him and he finally agreed. I got behind him, squirted his ass with lube and pushed myself deep inside him. It felt so good to penetrate someone again. It has been at least a year since I have been inside anyone and I needed to fuck him. I don't think he was all that comfortable with me being in him, but I needed it. I pumped back and forth for a few minutes until I exploded inside him. It was the best feeling I have had in a long time. Just to cum inside someone. It was all that I needed. I finally withdrew my cock and we laid spooning until we fell asleep.

The next morning, I left before David awoke. Seeing him lying there naked was all the pleasure I needed that day.

The next erotic pleasure occurred at a friend's wedding with Amanda in tow. Let's just say, she wasn't disappointed.

To Be Continued.

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BiSummerFunBiSummerFunalmost 3 years ago

Wow! What an incredible story. I’m all wet and horny reading about you MMM threesome, it’s such a huge turn on. Thank you for the multiple orgasms! You’re a spectacular writer adding in details that makes me want to be there with you, watching while playing with myself.

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