Mikes First Transgendered Pt. 02

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A story of my second transgendered experience.
2.8k words
4.53
26.4k
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Part 2 of the 26 part series

Updated 06/10/2023
Created 10/22/2020
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Mike's first part 2

Please go read part 1 before this.

Sara and I had talked via text and E-Mail several times after our first sexual experience. I was still unsure if I truly enjoyed it, or was just trying to digest the fact that I had finally experienced gay sex. I wanted to see her again, but didn't know if a second experience would as passionate or with as much desire. I thought about Sara a lot and what we had done. Some of me, wanted to do it again immediately, while the other part was leery, I'd like it too much and turn gay. Remember in the era I was raised you weren't gay and if people thought you were gay, you'd be ousted and criticized, picked on and made fun of. Of course, my biggest concern wasn't what other people thought, it was coming to grasp of who I actually was.

In conversations I agree to meet Sara for lunch again and spend some time back at my house. I didn't know what to expect as I drove to the restaurant to meet her. As I got out of my car, I saw her standing outside the entrance. She was wearing a knee length black skirt with panty hose, high heels and a white satin button up shirt, with a long coat. She looked amazing! her hair was lightly curled and free flowing. As I walked up to her my fears and concerns quickly evaporated. As she saw me, she started extending her arms as to give me a hug. Before I could even get my arms completely around her, I place a big wet kiss on her lips. Our lips parted slightly and we just barley touched tongues. I embraced her and was rather happy to see her. I wanted to show her how interested I was and how un-tethered I was about sleeping with her.

We sat inside and had a nice lunch and I was very comfortable sitting there with her. There was no nervousness, or concerns. I actually had thought to myself as the waitress came back and forth, if she knew this was a man and not a woman I was sitting with. Did the waitress know there was a big cock in those panties? Did she know I was hoping to be sucking that cock shortly after lunch?

We left the restaurant and she agreed to follow me back to my place. She did have to work at her restaurant later that night, but had a few hours to kill and wanted to spend time with me. It was only about a 10-minute drive to my house and I was excited she was coming to hang out. A million thoughts ran through my head as we drove back. Would I just take her immediately after walking in the door? Would she take me? Would the afternoon progress in anticipation until that first kiss happened? After arriving at my place, she slipped off her jacket and asked to use the restroom. When she returned, I was just in awe! I watched as this beautiful woman was back inside my house walking towards me, dressed so sexy, here for me. Here to be with me, here to make love to me. I got up from the couch and wandered up to her. Our hands reached for each other's. We stood there holding hands just talking and enjoying each other's company. I Told Sara; "I missed you and have been thinking a lot about you."

Sara replied, "I've been thinking about you too."

She asked me, "If I had been okay with our sexual experience?"

I said, "I was and hoped things could develop into more for us."

Sara smiled and said, "well looks like we could build on this."

I led Sara to my bedroom. I was so excited she was here. I stood with my back to the bed and as we began kissing. Her kiss was amazing. I wanted her so bad. I wanted to get her clothes off and just put that big cock of hers in my mouth. I wanted her to suck me, I wanted her to fuck me, I wanted her cum. As we stood there, Sara kicked off her heels and her height dipped to my level. We started undressing each other just like before. Except this time there was no fear or leeriness. I wanted this. I managed to get her shirt off and unhooked her bra. Just like before I started sucking on her nipples and listening to her ever-deepening moans. I pulled my sweatshirt and T-shirt over my head. Sara's head dipped down, she started kissing on my chest, sucking on my nipples. My hand cupped the back of her head. I can see her hands behind her fiddling with the zipper to her skirt. She finally managed to unzip it and let it fall to the floor.

I was rock hard and wanting her to do anything she wanted to me. I sat down on the edge of my bed just starring at her gorgeous body. Her breast fully exposed, her dick hard but held down by the panties and her panty hose. She reached at her hips and slid down and out of her pantyhose standing there with just her panties on. She smiled at me and slid her panties down. Her dick sprung out as it was released. Standing straight up, hard and ready for some attention. My mouth watered. Sara asked me, "Do you like my dick?"

"yes", I replied.

"Do you want my dick?"

"Yes", I replied.

I did want her dick! I wanted every inch of that dick and wanted it where ever she wanted to put it. Sara edged in closer to me and put her hand on the back of my head pulling me slightly down and towards her. She had her other hand wrapped around the shaft of her cock and before I can even get my mouth completely open, she pushed her dick into my mouth. I heard her incestuous moan as she pushed it all the way in. Her hips thrust slowly back and forth as her cock slid in and out of my mouth. I was looking up as her head was thrust back starring at those full plump breasts listening to her moan as I sucked her dick. I was in heaven! Sara whispered, "you're good at this." I got so excited I about split my pants. I sucked on her dick for a few minutes watching it slide in and out of my mouth. I was so turned on. So horny, so glad she came over. After a while, Sara pulled her dick form my mouth and told me to lean back. She unbuttoned and unzipped my jeans and pulled them off of me. She then pulled my underwear down and told me to move further onto the bed. My dick popped out and was standing straight up as I edged myself back further onto the bed.

As I centered myself on my bed, Sara climbed onto the mattress on her knees in-between my legs. Sara kissed her way up my legs. I could feel her hair gliding along my skin. She kissed all the way up my inner thigh and put my hard dick in her mouth. I let out a low deep groan. OMG, this feels amazing. I watched as Sara's head bobbed up and down on my hard cock. I was so glad I decided to try this again. I knew her hard cock was in-between her legs waiting for me to play with it more. Sara stopped sucking me and asked me, "if I ever did a 69 with a boy?"

I replied, "no."

Sara asked me, "do you want to try it?"

"yes," I replied.

Sara adjusted me to the middle of the bed and then swung her leg and body over mine. She backed up slowly until we were in the right position, she reached her hand between her legs, pushed her cock down a bit and placed it right at the tip of my mouth. I opened wide, lifted my head up and slid her hard cock back into my mouth and started sucking her again. I felt Sara's mouth swallow my cock and begin bobbing up and down on me. The feeling of being sucked, while sucking her off was intense. I had been in 69's with women before, but never with a hard cock in my mouth. My head motioning up and down as my mouth worked her cock, her balls resting and rubbing on my forehead, as she was working mine. Both of us moaning, getting more turned on, more aroused, more excited, hotter and closer to cumming. Sara's cock was bigger than mine and I FUCKING LOVED IT.

I couldn't suck it deep enough or fast enough. At times it almost gagged me as it hit the back of my throat. I knew I was getting close to cumming but I didn't want her to stop. I pulled her big cock from my mouth and said," I'm close to cumming." Sara moaned and with one hard loud giant suck pulled my cock from her mouth.

Sara climbed off of me and adjusted herself at my side. Her knees at my shoulder. Sara leaned down and over and put her dick back in my mouth. My head now bobbing sideways and up trying to suck her off. Just seeing it, playing with it, watching it slide in and out of my mouth getting her harder and harder, closer and closer to orgasm was the biggest turn on I had in a long time. I wanted it all... This wasn't going to be a passing phase. I couldn't get enough. I wanted to make her cum and cum again. The position we were in was uncomfortable, so I told Sara to sit on the edge of the bed. Sara pulled away from me, got to the edge of my bed and sat on the edge with her legs hanging over the bed, feet on the floor. I slid of the bed, got down on my knees and in-between her legs. Just the sight of her sitting there, tits out, fully erect, her balls hanging got my so excited. I leaned in, put my head down and went right back to sucking her cock. I was determined to give her the best blow job she ever had and I was going to make her cum hard.

I was giving her a blow job for a second time in the past week, sucking this big hard cock and fucking loving every minute of it. I was still rock hard and on occasion I reached down and stroked myself to keep close to orgasm, stopping when I was almost there. I must have sucked her dick for 10 minutes this way. Just trying different depths, different strokes, different angles, tonguing the tip, licking up and down her shaft, taking it as deep into my throat as I could. Just getting to know and enjoy sucking dick.

I was overly aroused as I gave her a blow job. And as time passed my lips got numb. But my mouth drenched with saliva, taking every inch of her deep down my throat, knowing I was pleasuring her, knowing I was going to make her cum. I bobbed back and forth and up and down as fast as I could, hearing the sloppy slurping sounds of sucking dick. Sara's hands resting on the back of my head. As Sara was getting close, she pulled me face away from her dick, looked me in the eye and said, "I want to cum in your ass!"

My heart skipped a beat. I wasn't sure I was ready for anal sex yet. I wanted to try it in real life. Lord knows I had fucked myself in the ass with dildo's and vibratos enough times watching porn movies, but the real thing??? I asked Sara "if we could wait another time or two for anal". I said, "I want to try it, just don't know if I'm ready yet."

She smiled and said, "of course."

Sara pulled me up from my knees and said, "I just want you to be happy and comfortable." With that she pulled me in for a long, wet, sexy kiss. I climbed back onto the bed with her. Both of us engrossed in each other's bodies, minds and passions.

Sara and I laid kissing for quite a while, using our hands to touch, rub and stroke each other off. We took turns sucking each other off for the next few minutes. She brought me to orgasm rather quickly with my loud moans of "I'm going to cum."

Sara swallowed every drop of my cum. After she finished me off, I rolled her onto her back, I got on my knees and was sucking her off waiting for her to explode. Sara was getting close and was moaning she was about to cum. I had never swallowed cum before, but I was ready for it today. I wanted to know what it was like to have my lover cum in my mouth. To have them explode because of the oral sex I was giving. Wondering what it tasted like?

I bobbed my head up and down faster and deeper awaiting my surprise. Within seconds Sara let out a big moan and screamed, "I'm cumming!" I felt the rush of hot wet sticky cum fill my mouth. Her ejection hitting the back part of my throat. It was a lot. More than last time when she came all over my chest, face and neck. I kept bobbing up and down slurping up every drop I could get. I eventually swallowed it all down my throat. It left a tingly feeling as I swallowed it. I looked up at Sara who was lying there naked, sweaty, catching her breath as she was oozing the last bit of her hot load in my mouth. What a sight to see a beautiful woman, with her big tits showing as her big 7" cock was still deep in my mouth.

I made sure I got all of her cum before I finally pulled her dick from my mouth. The smile on her face was priceless. I wanted her today; and now I wanted this even more. I laid next to her for a while just softly touching, kissing and talking. We both dozed off for a bit and after I awoke with this hot shemale in bed next to me naked, I was ready for more. I knew I wasn't gay because I have had lots of women before her, before this, but I surely knew I was becoming quite fond of dick. At least her dick.

Eventually, Sara had to go to work. I walked her to the door and we kissed goodbye. I wanted her to stay, I wanted to ask her to come back after work, but I still wanted time to reflect upon my sexual experiences before seeing her again. As she walked to her car, I was wondering if the neighbors who were seeing her leave knew she was a boy? I still couldn't believe she was a boy and was still somewhat taken-a-back as to what I was doing. But knew I was developing a fondness for it. For her. That's the day I fell in love with dick. That's the day I knew I was BI-Sexual. That's the day I truly began loving boys and dick and cum and eventually anal Sex. That's the day I knew my life was going to change. I may not have known it at that moment, but looking back it was that day.

Later that night as I laid in bed alone, thoughts of her, that dick, those tits and her cum got me horny again. After stroking myself for a bit re-living the days experience, I got out my dildo and lube and I fucked myself thinking about her. I rode my dildo wanting it to be her, wanting to feel her deep inside me, feeling her cum in my ass. Wanting to know what it felt like to be fucked, instead of fucking. Wishing she was there pumping me hard with that cock of hers. I rode my dildo that night for a long time. Looking back, I wished I would have let her fuck that day, wishing I would have called her that moment. Wishing she walked through my door after work, kissing me and making love to me before we fell asleep. Wanting to wake up tomorrow next to her and that dick. OMG, I wanted her to fuck me now, more than ever...

Hoping next time, I'd get my chance.

Wouldn't be long until I found out.

To be continue...


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3 Comments
MisterMongerMisterMongerabout 3 years ago

Loving this series, i really identify with the mental fuckery of giving yourself permission to truly enjoy a ladyboy, its a tricky minefield and the ultimate acceptance is taking it in the ass and loving it. Thanks for writing

BiguyinOC69BiguyinOC69over 3 years ago
LOVE gurlcock as well

I remember the first time I was with a TG gurl. I was with a Bi woman at the time who had been fucking my ass with her strap on when she introduced us and the rest became history

nutcase666nutcase666over 3 years ago

Love this series plesse continue the story

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