Home > Blogs > Crossdresstena > Open to having good times with good people > Blog Post

My journey from straight to cd cocksucker.

2:41 pm Monday, 26th November, 2018

I wanted to tell people who I am and what I am really like.  I look at profiles and there are a couple of pics and a brief description.  I make assumptions about the people based on very little information.  I shouldn't but I do.  Hopefully this will help people understand me better!
When I was younger I was practically homophobic.  I never even considered dressing as a woman or sexual contact with men.  I didn't like any contact with men at all...not even a handshake.  In my mid to late twenties I was often looking for porn online (hmmm....still do, lol!).  Back then most sites did not have thumbnails, only descriptions.  I clicked on a gallery of a "hot sexy blonde" and started scrolling through the pictures.  Face pic, clothed, bra, tits, and suddenly, she had a cock!  I had heard of "shemales" but that was the first time I saw a shemale nude pic.  I was fascinated that such a hot looking woman could have a cock.  For the next year I hunted for shemale porn but was only looking for the hottest, most feminine looking shemale pics I could find.  I skipped over crossdressers and any cock closeups.  Looking at cocks still seemed gay to me and I was still unsure how I felt.  After about a year I was starting to look at their cocks a bit more, deciding that some cocks looked pretty nice and might be fun to touch, play with, maybe even suck.....  I made the decision that I had to try it.  I was in Toronto at the time and there were free newspapers that had lots of different listings for "shemale escorts".  Most didn't have pictures but I didn't care.  I went to a strip club, had a few drinks (quite a few) to work up the courage then called an ad.  I went to her place, she opened the door and I was stunned at how gorgeous she was.  She took one look at me and said "this is your first time, isn't it?"  She knew right away I was nervous and said she was not the right person for first timers.  She asked me to leave but come back after I had met with someone who advertised that they were good with first timers.  I was disappointed...she was gorgeous but I left.  I called another ad and when I got there I was not as happy.  She was not as attractive and a bit chubby.  I had to get it over with though so I paid her and she led me to the bedroom.  I won't tell the story this time but if anyone wants to know about specific experiences I will post more blogs.  I had a great time with her and loved sucking cock.  I did let her fuck me but did not enjoy it....I hope I will someday.  After that I was hooked and went to a few escorts.  I enjoyed most but not all but am glad for each experience I had.  I moved away from Toronto and spent a few years with only online porn to satisfy my shemale fetish.  I managed to take a couple of vacations to Toronto and wen to Goodhandys on a T-girl night.  Had fun but too many escorts...I was hoping for real people looking for fun.  I did find some and did have fun though but left alone.  I had gotten a couple of blowjobs and sucked 1 cock there but wanted more so called another ad and went to another escort.  That was my best experience ever with an escort.  She had been at the club too but we never noticed each other.  I ended up staying the night at her place and she even wanted to cook me breakfast the next morning.  My next trip to Toronto was another great time.  I went to M4 and had a wild threesome with a transexual and her boyfriend while several guys watched us and jerked off.  Amazing night!  
I went to a transexual massage parlor in Montreal a couple of times and had a great time.  Trans-friendly bar in Montreal (citibar...closed now), had an okay time there.
After all that I still hadn't even thought about dressing until a gf told me she had a fantasy about role reversal and pegging me.  I agreed to her fantasy and said we would do it the net time we saw each other.  She lives pretty far away and I don't see her often so I had time to prepare.  I bought a couple of strapons online and found some old lingerie I had from ex gf's.  I tried some things on to see if they would fit...a bit tight but I could make it work.  I shaved my body smooth, put on the outfit I had picked, a halloween wig and started taking pics of myself in the mirror.  I couldn't believe how good I actually looked....it felt amazing.  I posted several of the pics on a website and had a lot of great comments.  It was so much fun I ordered some outfits and real wigs online and started dressing up more often.  Pictures to post, webcam sites so I could chat en femme and everytime I dressed I felt different.  More girly, more interested in men and being the girl in a sexual encounter.  I posted a couple of ads on cl and had 1 guy come over while I was dressed.  Not a great experience but it was okay.  That was the only time I have been dressed in front of someone.  I went to a gay spa a couple of times after that for some cocksucking fun and really wanted to go to Sauna St.Hubert in Montreal on T-girl night.  I was planning on that being my first night out dressed in "public".  They closed recently and I never went.  The only other option I can find now is "Cinema L'amour" that has a T-girl night but I am not sure what to expect there.  
After all that I joined this site and am hoping it will lead to some new and wonderful experiences....contact me!




Comments
4:41 pm Monday, 3rd December, 2018

Wow i can say you are much braver then myself,hoping to get there one of these days. Luv the experiences you have had. I enjoyed reading your blog,thank you for sharing your experiences and hope you have many more to follow.

Blog Introduction

Open to having good times with good people


Get full access to all site features
Register Now