Mikes First Transgendered Pt. 03

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A story of my third transgendered experience.
2.9k words
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Part 3 of the 26 part series

Updated 06/10/2023
Created 10/22/2020
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Please read 1 and 2 before this one.

Mid October has set in and once again I am leaving work later than usual. I am in the parking lot speaking with co-workers when my phone rings. I recognize the number as being from the restaurant Sara works at. I answered and hear her voice on the line.

Sara Says, "Hi Mike. How are you?"

"I'm good Sara. How are you?" I reply

During our conversation Sara says, "She misses me and would like to see me tonight."

I asked her, "Are you still at work and if so when will you be done?"

Sara replies, "Yes, I am still at work. I have a few things to put away and straighten up, but I should be done in about a half an hour." Sara says, "Come by, have a drink and we'll hang out for a few minutes after I'm done."

I agree and start making my way there. I enter the restaurant and see her. I sit at the bar and order a drink and she comes over to me and gives me a big hug and kiss on my cheek. Sara says, "Give me a few minutes and I'll have a drink with you."

I sit at the bar and start thinking of her more deeply. I watch her as she's finishing up with work. Tonight, she is wearing a mid-length black skirt, with a blue dress shirt on. High heels and black pantyhose. Her walk is sexy, her voice is erotic and her smile lights up a room. I am in awe of her. And I must say there hasn't been to many days since our last visit that I haven't masturbated thinking about her and that dick of hers. Fucking myself with dildo's and vibrators preparing for the day we finally have anal sex. Wondering if this is going to go on for a while or is just a fling? I start wondering if she thinks of me as much as I think about her? I wonder if she's just having sexual fun with me, or if this is something more?

Within a few minutes Sara comes over, sits down and orders a drink. We have a great mood lightening chat before we decide to head out. The restaurant / bar is still crowded as we head towards the parking lot. I walk arm in arm with Sara to her car. When we get there Sara says, "Get in for a bit."

I agree and get into her passenger side. I lean on my left hip facing her as she leans on her right facing me. Her face is amazing, with her beautiful light brown Asian skin, all-natural sexy look. Sara grabs a hold of my hands and says, "Mike, I'm glad you stopped by, I needed to see you and talk to you. There's something I need to tell you."

Sara takes a deep breath, preparing herself and says to me, "I am into you and I love where this is going. But I just want to make sure you feel the same way and this is not some sexual fling or some shemale fantasy notch on your bed post."

I smile at Sara and reply, "I'm glad you brought it up, because that's been on my mind for a while now."

I continue, "Sara I am very interested in seeing you more and seeing if this can develop into more of a relationship. I never thought I'd be this interested in dating a shemale, but I am enjoying it so far."

Sara seems to be relieved by our conversations and even though I have fought some inner battles about dating a Shemale and experiencing dick, I am willing to see what happens.

Sara leans towards me and puts her lips on mine. Knowing what we both said and both admitted, our kiss seems to be more intense and loving than ever before. Our lips part and our tongues touch. The feeling is incredible. We both pull away and smile. As I look at her I truly realize I am falling for her and have really liked (so far) having dick and not pussy. We go back to kissing deeply in the parking lot and it is getting me turned on. As our kissing continues, our passions increase. We are engaged deeply with each other and getting more and more aroused, only to be interrupted by people walking through the parking lot heading to their cars. We giggle every time someone walks by, but we go right back to kissing deeply after they pull out. The windows are getting foggy with each passing minute.

I want her so bad; I want to get her out of those clothes. I want to pull her dick out from her panties. I want to climb over this rather large stupid center column dividing us. I want to slide my cock deep in her ass. I want to cum inside of her, I want to see her cock shooting cum out of it as I am fucking her in the ass. I want it all!

After our 4th interruption of people walking by, I tell Sara to, "Drive over to a different section of the parking lot."

Without hesitation, she starts the car, straightens herself out and we move to a more secluded area. She backs into a spot, so we can see the vast majority of the lot. This way no one, not even the cops can sneak up on us. We go back to kissing deeply. Our bodies leaning in towards each other. Our hands touching and rubbing each other. I unbutton the top two buttons of her dress blouse and slide my hand down into her shirt. I cup her left breast over the bra. Her tits feel amazing. I am so turned on by her. Our hormones are racing and I know I want to cum. There is no way we are going to get any further in the front seat of this SUV, so I suggest to her we climb in the back. Sara smiles and says, "Ok."

We both exit her car and climb into the back seat. After settling back in we giggle like two teenage kids as I say, "This will be better."

Sara kicks off her heels and we go back to kissing, this time we have nothing separating us. We are cuddled together, arms wrapped around each other. I slide my hand back down onto her breast feeling her body react to my touch. I break from our kiss and I kiss along the side of her face, along her neck and lightly nibble at her ear. My dick is hard and bulging in my pants. "I want you Sara" I whisper in her ear.

Her body reacts and she pulls me closer to her. I feel Sara's hand rest on my inner left thigh. She is rubbing up and down my leg and I am wishing her hand would make its way up to my cock. I pull my hand from her shirt and place it on her sexy panty hosed leg and start rubbing up and down. I love the feeling of panty hose on skin and knowing her panty hose lead to a big hard cock is such an incredible turn on. Sara whispers to me, "I'm so hard."

With that she breaks from our kiss and sits back, scans the parking lot and starts sliding her skirt up towards her ass. She finally gets it high enough and behind her enough that I can see she is wearing those elastic / stay up thigh high panty hose. Her black panties bulging with her hard cock inside them. My mouth waters. She unbuttons the rest of her shirt and pulls the cups of her bra down releasing her tits. I lean my head down and start sucking on her tits. My hand goes back to rubbing in between her inner thigh. I suck on her breasts as my hand finally reaches her hard cock, stuck inside those black panties. I rub and caress her cock wanting to pull it out. Sara's head is back and she is moaning in pleasure. I feel her lift her hips and with one fell swoop she slides her panties all the way down and off. When she sits back up straight, I reach down grabbing a hold of her hard cock. I am so excited to grab a hold of her erect cock.

After slowly stroking her hard cock with my hand, I pull away from her lips. I want to suck her cock. I want to make her cum. I look around the parking lot to make sure the coast is clear and I lean down putting the tip of her hard cock in my mouth. Sara lets out a soft moan. I slowly bob up and down taking more of it into my mouth. I get it so far in that it hits the back of my throat. I stop, holding it there for a few seconds as my mouth fills with saliva. I continue bobbing up and down on her cock, making slurping sounds as I suck her off. I stop for a second and use my hand reminding her to watch out for anyone pulling up on us. I put her big cock back in my mouth adjust my angle a bit and continue giving her a nice wet blow job. I want to please her, I want to make her feel loved, most importantly I want to make her cum. I love the feeling of her hard cock sliding in and out of my mouth. Feeling her hard-pulsing dick soaking wet with my saliva. Her hand on the back of my head as I bob up and down. My cock is raging hard and my asshole is tingling wanting to be played with. All I can think about is pulling my dick from my pants and sliding my cock deep inside her, or her sliding hers into me.

I have never given a blow job in the car, but now I'm doing it with a shemale I am falling in love with. I have to let my dick out. I reach down and unbutton and unzip my pants. I reach down into my underwear, letting my cock stand straight up. I am hard as a rock as I pull on my shaft making me even more horny, hot and turned on. Sara starts moaning loudly begging me to go faster. I pick up my pace and suck as hard and as thorough as I can. I stop jacking myself off and use my hand to help her get off. Slurpy sucking sounds fill the car as I work up and down her shaft using my mouth and hand to please her. Sara whispers, "I want to cum inside you!"

I am so tuned on by those words that it sends shivers down my spine. I think for a second about climbing on top of her and letting her slide that big cock inside me. I want her to fuck me, I want to experience anal sex. I want to ride her cock, but I know this is not the time or place. I pull her dick from my mouth grabbing it with my hand, looking up at her as I whisper back, "Not here, next time were at my place."

I feel Sara's hand go back to the top of my head. She pushes my head back down onto her cock. Just that bit of force got me even more turned on. I slurp up and down on her. When my mouth gets tired, I pull her dick out of my mouth holding it at the base of her shaft. I'm swirling my tongue around the tip, rubbing it along and around my lips and licking up and down her shaft. I stroke her hard making her moan even deeper. When I know she's harder and hotter, I slide her cock back into my mouth. I go back and forth between my mouth, to my hand and back to my mouth pleasuring her. I continue bobbing up and down on her shaft, just feeling her body move and quiver as I continue this erotic blow job. The tip of my dick poking out of my pants, begging to be played with. As I continue sucking her, I can feel Sara start breathing heavier, her hips start thrusting upwards slightly jamming that cock deeper into my throat. Sara starts moaning, "I'm going to cum, I'm going to cum."

My sexy woman, with her big 7" cock is about to explode deep in my mouth because of my blow job and I am so tuned on by it. I keep sucking her hard cock as her hips start thrusting upwards more rapidly. Within seconds, her moans of, "I'm cumming, I'm cumming" fill the car as I feel her hot sticky cum start filling my mouth. I continue sucking up and down slowing my pace, allowing her to keep squirting her hot load down my throat. I swirl my tongue around her shaft as it's in my mouth. I hear her moaning, "OMG, Mike that's what I needed." I keep my mouth wrapped around her cock until she finishes cumming. I swallow every drop of her cum and wish she had more. I love seeing her big cock and get so hot by playing with her making her cum.

I finally release Sara's cock from my mouth. Moving back up to her face. We kiss deeply and she smiles and says, "Thank you."

Sara eases me back to an upright position and leans me back against the seat. She pulls her skirt down, shifts onto her right hip and reaches for my pants. She discovers I have already unbuttoned and unzipped my pants and the tip of my dick is sticking out. She spreads the material out as far as she can, pulls my underwear down letting my hard cock completely free. She leans her head down and wraps her lips around the top of my cock. I feel her take me all the way in her mouth. I moan in pleasure. Sara's head is now bobbing up and down along my shaft. I feel her tongue striking the tip as it goes in and out. I am so fucking turned on and so horny, it's not going to take me long to cum. I put my hand on the back of Sara's head and my hand goes up and down as her head does. I moan aloud, "OMG, Sara, I love you sucking me."

Sara works my cock like a pro, she sucks dick good. Her wet mouth sliding up and down my shaft makes me feel like I'm in heaven. I feel her hand working in conjunction with her mouth as she slurps away at getting me off. As I sit back enjoying her sucking my cock, I lick my lips, I can still tase her cum in my mouth. I so want to be in her right now. I really want to be sliding my cock in and out of her ass right now. I want to fuck her. I want to know what's it's like to have anal sex on a shemale. I want to cum all over the place. Sara stops on occasion using her hand only to stroke my shaft hard and fast for a few seconds then puts me right back in her mouth. God I'm loving this. "Sara," I whisper, "I want to be in you. I want to cum in your ass."

I close my eyes and envision putting her on her knees, raising that skirt up, climbing in behind her and sliding my hard cock deep in her ass. OMG, I want to fuck her tight ass! As I fantasize, Sara's bringing me even closer to orgasm. It's not going to take me long until I explode. "Sara, I'm going to cum, I'm going to cum."

I feel her stroke me off a few times with her hand and just as she puts my cock back into her mouth and I start cumming. My cum is thrusting hard, I am giving her a mouthful. I can feel my cock pulsing and thrusting as I shoot out every drop. When I finish cumming Sara pulls my dick from her mouth. Sara sits up and leans in to kiss me. As our mouths meet and tongues start swirling around, I get a taste of my cum on her tongue. Sara and I kiss deeply for a while, just holding each other as we catch our breath. My dick still hard still releasing the last bit of cum as I settle down from my orgasm. I am becoming even more comfortable with her and her cock. "Whew, Sara, that was incredible" I whisper.

Finally, realizing the time, Sara says, "I have to go." We both get dressed and fix ourselves, climb back into the front of her car and she drives me back to my car. We kiss again, both of us spent, tired and fulfilled. I ask her, "When's the next time I'm going to see you?"

Sara replies, "I hope soon."

As I part ways from her, I was happy I stopped by to see her. An unexpected, erotic night of oral sex was just what we both needed. But I still want more. Next time we are together, I want her cock in me!

To be continued...

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3 Comments
sensuousOkietopsensuousOkietopover 1 year ago

I am so glad I've discovered your writing. It's entrancing and what really comes through is the yearning. So good.

AnonymousAnonymousabout 3 years ago

Wonderful series. Thank you.

Single_ElizaSingle_Elizaover 3 years ago

your story is so hot and has me so wet, I'm going to have to clean up before reading more. xxx

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