First time with a CD or TS

[chris313163]

What was your first experience with a crossdresser of a TS like? Was it by accident, did you seek out the encounter? Was it a "one time" thing? For me, it wasn't planned. I did enjoy the experience, and after the first time, I did seek out CD's.

 

[Buttboy7869]

What was your first experience with a crossdresser of a TS like? Was it by accident, did you seek out the encounter? Was it a "one time" thing? For me, it wasn't planned. I did enjoy the experience, and after the first time, I did seek out CD's.

Similar experience here. Scorching hot.

 

[Escierto]

My first experience with a trans woman occurred many years after I first realized how I felt about trans women. It took me that long to act on my desires and I was nervous about how it would go.

We spent a week together and the sex was amazing. Unfortunately we did not mesh well personality wise but that's life. My next encounter with a trans woman led to a relationship that here we are, five years into it still together.

 

[SmokingFap]

My first experience with a trans woman occurred many years after I first realized how I felt about trans women. It took me that long to act on my desires and I was nervous about how it would go.

We spent a week together and the sex was amazing. Unfortunately we did not mesh well personality wise but that's life. My next encounter with a trans woman led to a relationship that here we are, five years into it still together.

When I saw this thread pop up, I knew you'd be among the first to respond to it.

 

[Escierto]

When I saw this thread pop up, I knew you'd be among the first to respond to it.

I hope that's not a bad thing. It seems that few men have experiences with trans women let alone relationships. I always hope that someone can benefit from what, for me, was a difficult journey.

 

[SmokingFap]

I hope that's not a bad thing. It seems that few men have experiences with trans women let alone relationships. I always hope that someone can benefit from what, for me, was a difficult journey.

I'm sure everyone on this thread will love to hear about your experiences.

 

[SPARTAN047]

It was a threesome. Nothing mind blowing but two huge cocks to please.

 

[Dnthmn_19]

I loved it:

https://www.literotica.com/s/skye

 

[BiDrew42]

My first was with a Shemale escort (she identified as Shemale in her advertisement). I found her in a swinger's magazine (no internet back then) called Unique Encounters during a visit to my favorite Adult Bookstore where I had watched a video featuring trans women. Called her number and arranged a "date." I was 21, nervous, but incredibly horny at the thought of having sex with a sexy, feminine woman with a big dick! Fell in love when she opened the door to her apartment. Her name was Dusty and she had curly blond hair and looked amazing in her sexy lingerie with a lovely bulge in her panties. Years later when I saw a picture of Joan Jett for the first time I thought she looked a lot like Dusty. The sex was amazing and I saw her several more times over the next couple of years, along with a number of other trans escorts I found in the same magazine. My lifelong obsession with trans women began the first time I hooked up with Dusty.

 

[Versa92646]

My first encounter was definitely not planned.

Alana owned 24 hour laundromat in Atlanta. My work hours were crazy then so starting a load at midnight made my life easier. That became my Wednesday night routine. I admired the pride she took in her business and appearance with nails done and light makeup. She would slip in, check the trash and exchange a pleasant hello and be off. One night she wore these tight jeans and heels that accentuated her curvy ass beautifully. She was wiping down the machines and caught me admiring the view. Flustered I went out back to my truck to smoke a cigarette.
So I’m sitting on my tailgate trying get my head around being straight yet turned on by this hotty when Alana came out dragging a nearly empty trash can to the dumpster. On her way she teetered on those heels. She shook her head and kinda chuckled at herself. Coming back from the dumpster she paused in front of me, “New heels, still getting used to them.”
I blurted out, “I like them, they make your butt really cute.”

She melted. “Can I have one of those?” I pulled a Marlboro from the box placed it between those nails. She laid a hand on my thigh as she leaned in for a light. My cock started to swell.

Taking a puff of the cigarette she looked me over and I could see her making a decision. Taking a half step back and turning around she put more arch in her back, “So this is the view you like?” Giving her hips a little wiggle and running one hand up the back of her thigh to cup one asscheek. “Want a feel?”
When I put my hand on her hip she backed up on my crotch. Between her size and heels she was at the perfect height. Just a few wiggles had me fully erect.

Looking around she undid my shorts and asked permission before pulling my cock out.

All thoughts of straight/bi/CD/ gay left my mind as she sucked me off in that alley. I was just a guy getting a blowjob from an attractive person that wanted me.

It was not the only time with Alana and she opened a world of possibilities for me.

 

[KinkyLaughs]

It was a threesome. Nothing mind blowing but two huge cocks to please.

Sounds pretty mind blowing to me!!

 

[SPARTAN047]

Sounds pretty mind blowing to me!!

It was delicious! But cheesy so not that great.