Mikes First Transgendered Pt. 06a

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A story of my on-going transgendered experience.
1.5k words
4.48
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Part 6 of the 26 part series

Updated 06/10/2023
Created 10/22/2020
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Mike's first transsexual experience part 6

Please read 1 -- 5 before this one.


After Sara and I parted ways I stayed single for a bit. I was just getting back into work, seeing friends and just living life. I still wasn't sure where I was sexually. I knew I absolutely enjoyed being with Sara and if things would have continued, I would have been okay with that, but I also was thinking maybe it was a passing phase or an opportunity that "presented itself" and life would go on. After a while of being single I placed an add on one of those popular dating sites "looking for women." After a few weeks and a few conversations, I got a message from a Filipino lady named Enna. I replied to her message and over the next week or so we chatted on the site, until we finally swapped phone numbers and started calling and texting.

Enna had a fairly deeper voice, but seemed all woman to me. Finally, after she sent me a few photographs, I saw the bugle in her pants and asked her if there was, "Anything special about her?"

Enna finally admitted, "There was something special about her, she was transgendered."

I met Enna for several short dates, getting to know each other. The way I looked at it I had just spent a length of time with Sara and dick, so to discovered another trans woman and have dick again, kind of led me to believe the planets and stars aligned and this is where I was supposed to be. Enna and I had our first kiss after a romantic dinner, when we walked along the lake shore in our hometown. I was being the perfect gentleman and did not push for anything more. A few days later on a Sunday, Enna invited me over to hang out and watch a movie. I drove to her place, which was closer to the inner city and hung out with her. Enna put on the movie and sat next to me (to the left) on her small love couch and a few minutes into the movie, leaned over and placed her head on my shoulder. Within a few minutes, she looked up at me and I made my move. I kissed her big soft lips gently until our mouths parted and our tongues met again. We kissed for a few seconds figuring each other out and pulled away returning to the movie.

Minutes later our kissing started Again. I slid my right hand onto her upper chest running along her neck. I slowly slid my hand down her chest until I hit her left breast. I felt Enna's left-hand rest on my left thigh. She rubbed back and forth staying in the same spot as our kiss got deeper and more passionate. I tried to reach into her shirt, but her shirt was so tight I couldn't get into it. Enna pulled back from our kiss and pulled her shirt over her head revealing her plump, luscious augmented breasts. When we leaned back in continuing our kiss, I cupped her left breast and rubbed all around her chest. Her hand started moving further up and down my thigh, until she hit my crotch. Her hand gently and softly rubbed my dick and balls over my pants as I reached my hand into her bra cup feeling her soft skin and hard nipple.

Enna and I kiss for a while, still feeling each other out when I felt her hand start unbuttoning my button and unzipping my pants. Her hand slid down into my pants rubbing up and down over my dick and balls over my underwear. I was getting hard and surprised she had made a move so quickly. Enna's hand pulled back and she pulled my hard cock from my underwear, starting to slowly stroke me off. I moaned in pleasure as she caressed my hard on. Enna pulled from our kiss and leaned downwards placing my cock into her mouth. I leaned back and just enjoyed the view of her head bobbing up and down on my shaft. I rubbed her naked back over her bra strap, until I finally unsnapped it. Enna worked out of her bra, while still sucking my cock. I was in absolute pleasure and I wanted to see, touch and suck her cock. I pulled Enna upwards and started kissing her passionately. I leaned her back onto the couch and slid my hands deep in-between her legs feeling her hard cock inside her yoga pants.

I rubbed up and down her cock over those yoga pants as I kissed my way down to her sexy, plump and luscious tits. I licked her nipples and sucked on them making them harder and harder. Enna lifted her hips from the couch and slid her yoga pants down to her ankles spreading her legs open for me. I felt the soft silkiness of her panties as I continued kissing her and rubbing her big boner over her panties. My dick popping out of my underwear as we got more involved with each other. I was so excited to be feeling cock again and glad I had met her.

I pulled from our kiss and slid my pants and underwear all the way down as Enna kicked off her yoga pants. As we re-embraced, I slid my hand down into her panties grabbing a hold of her thickening cock. OMG it felt so erotic and sexy to have a cock in my hands. I stroked her up and down feeling how sexy her dick felt sliding in and out of my hands. Listening to her moan, so truly erect and fucking horny I was. We kissed passionately and deeply. I kissed my way down her chest and adjusted myself on the couch until I was face to face with her erect cock. It was beautiful.... Not as big as Sara's but she was surely well endowed, with a thick head; long lightly brown skinned shaft. Without hesitation, I placed her cock into my mouth as started sliding up and down it. Enna moaned in pleasure as I started giving her a long wet slow blow job. I was rock hard and couldn't wait to suck on her more. I couldn't have been in a better place mentally. I was back to sucking cock and was fucking loving it!

After a few minutes, Enna was getting close to cumming, so she pulled my head from her cock and slid off of the couch. She pushed me back up against the back of the couch. She got on her knees in-between my legs and placed my throbbing cock back into her mouth. She bobbed up and down on my dick as I sat back in pleasure. I placed my hands on the top of her head and just enjoyed the pleasure of her sucking me off. When I got close to orgasm, I pulled Enna from my cock and lifted her from her knees. Enna stood up and slid her panties off, standing naked in front of me, her breasts perky and plump. Her Sexy brown skin all smooth and shaved and a hard cock standing erect. I leaned forward and began sucking her off again. The taste of her cock in my mouth, couped with the taste of her pre-cum made me overly excited. I was at a bad angle so I slid down off of the couch and down onto my knees, lowering myself as far down as I could go. I bobbed back and forth sucking her cock listening to her moan and groan in pleasure. Enna grabbed the back of my head and assisted me in going back and forth jamming her cock deep into my throat. I felt her start moaning further as she started to whimper.

"Mike, Mike, I'm close"

Within a few seconds I felt the warm gooey sensation of her cum squirting into my mouth. I moaned in pleasure as I continued siding back and forth on her cock, swallowing every burst right down my throat.

When Enna finished, she smiles at me and said, "Your turn."

Enna laid me flat on my back on the floor and climbed down in-between my legs. Enna put my cock back into her mouth and bobbed up and down for the better part of 5 minutes until I came in her mouth. She swallowed every bit of my cum down and slowly sucked me off until I was absolutely finished. Enna slid up next to me and we laid cuddled together on the floor. We softly kissed and caressed each other's bodies until it was time for me to go home.

As I left, we kissed at the door and Enna whispered in my ear, "I hope to see you again soon."

"Yes, you will," I replied.

I texted Enna when I got home and thanked her for a great Sunday afternoon. I knew my place in the world now. I went from about a year of Sara's cock, being single a bit, right to Enna's cock. Guess I am attracted to and addicted to cock!

I did see Enna for about six months, but it wasn't as steady as Sara, but I didn't mind, I was getting cock again and I experimented with her with more sexually than Sara and I ever did. I'll tell you all about them in the next chapter.

To be Continued...


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2 Comments
Afterhours22Afterhours22over 3 years ago
Loved it

Sure made me wish to see Enna.

CDsuzie69CDsuzie69over 3 years ago
Why do I crossdress? Simple.....because I love it.

I loved your story. It got me hard. I just wish it had been mine you were sucking and I would have done the same for you.

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