Older men (60+) who have had experiences with CD's and TS's

[chris313163]

Looking to share experiences with older gentlemen (60+) who have had experiences with CD's and TS's. Was your first experience by accident; were you curious, or did you actively seek out a CD or TS.?

 

[jpro56]

65 here. It has been a while back but I have been with a few CD's. First time I just got a blowjob, I was nervous as hell. Other time have been more mutual pleasuring.
I am yearning to have a relationship with a true pre-op trans woman. I haven't found one locally that is interested.

 

[Escierto]

I have told the story several times of how I used to chat with a pretty Filipina girl on an old defunct web site. One day she confessed to me that she was trans. I didn’t believe her so she showed me her cock. OMG when I saw it I wanted it which surprised her very much. We began a long cyber relationship in which I eventually helped her get out of cam modeling. I never met her in person but I have fond memories of her.

Now I am in a relationship with a beautiful transgender Filipina and I will be seeing her again in July. This is our fourth year together.

 

[xdresssissytoes]

My first time with a CD was before I had much experience with dressing myself. I was a BWM cruising a park known for gay/bi casual hookups. We crossed paths and she circled back to look and chat. Once we knew that we were there for the same reason, we drove to a secluded area and started groping each other and rubbing our hard bulges against each other. Soon, we had released each other's straining cocks for mutual jerking and sucking. She was very sexy, horny, and passable in her make-up and sexy outfit! I was very turned on by this first experience and started to develop and nurture my submissive feminine side while dressing sexy and slutty for sex with a guy.

 

[Escierto]

She is very attractive, l could very well be attracted to her myself.......

Thank you. She is a lovely woman.

 

[drobert44]

My first time with a CD was before I had much experience with dressing myself. I was a BWM cruising a park known for gay/bi casual hookups. We crossed paths and she circled back to look and chat. Once we knew that we were there for the same reason, we drove to a secluded area and started groping each other and rubbing our hard bulges against each other. Soon, we had released each other's straining cocks for mutual jerking and sucking. She was very sexy, horny, and passable in her make-up and sexy outfit! I was very turned on by this first experience and started to develop and nurture my submissive feminine side while dressing sexy and slutty for sex with a guy.

lovely

 

[chris313163]

My first time with a CD was before I had much experience with dressing myself. I was a BWM cruising a park known for gay/bi casual hookups. We crossed paths and she circled back to look and chat. Once we knew that we were there for the same reason, we drove to a secluded area and started groping each other and rubbing our hard bulges against each other. Soon, we had released each other's straining cocks for mutual jerking and sucking. She was very sexy, horny, and passable in her make-up and sexy outfit! I was very turned on by this first experience and started to develop and nurture my submissive feminine side while dressing sexy and slutty for sex with a guy.

Sounds like a really fun experience. I know the feeling about developing and nurturing a submissive side when being with a CD; I always prefer give oral pleasure before receiving it.

 

[Gypieman]

Looking to share experiences with older gentlemen (60+) who have had experiences with CD's and TS's. Was your first experience by accident; were you curious, or did you actively seek out a CD or TS.?

Hello great topic I had a relationship with a CD/.When I was swinging me and my partner got with a CD and played around some.I enjoyed sucking her cock along with my other .I watched her get fucked with a strapon as she was sucking my cock.I enjoyed ever minute of it.To bad it didn't last that long.YES!! I'm looking for another one to have fun with .

 

[chris313163]

My experiences with CD's have all been good. Seems CD's make a greater effort during sex; and most give better oral sex than women. The times I was with a CD and a woman were exciting. When I watched the CD fuck the woman, it looked as if two women were having sex. So hot. I've been in a relationship with a CD for quite a while; where we see each other once or twice a month---it's been very satisfying.

 

[BiDrew42]

My first experience with a Shemale was 40 years ago. After watching a couple of shemale videos at an adult bookstore, I purchased a Swinger's magazine that had ads for shemale escorts. I contacted a shemale who lived near me and arranged a date. Her name was Dusty and she was incredible, beginning my lifelong attraction to beautiful women with cocks. I have fucked hundreds of shemales and ladyboys all over the world since then, mostly escorts and prostitutes. My girlfriend of the past seven years is a pre-op transgender female. When I met her she was just crossdressing, although she was living and working full time as a woman even then. Now after several years of hormone therapy and some surgical procedures, she is more beautiful and passable than ever. Fortunately we have a wide open relationship, and I continue to frequent escorts and prostitutes. I have just returned to Australia after nearly seven weeks in Thailand, where I spent about equal time in Bangkok and Pattaya Beach after a long time away due to Covid. I'm happy to report that, although things are a little different, there are still a large variety of gorgeous ladyboys available to satisfy my particular desires. After this latest trip, I have decided that I will move to Pattaya when I retire and live in a villa on the beach staffed with young ladyboys!

 

[Escierto]

My first experience with a Shemale was 40 years ago. After watching a couple of shemale videos at an adult bookstore, I purchased a Swinger's magazine that had ads for shemale escorts. I contacted a shemale who lived near me and arranged a date. Her name was Dusty and she was incredible, beginning my lifelong attraction to beautiful women with cocks. I have fucked hundreds of shemales and ladyboys all over the world since then, mostly escorts and prostitutes. My girlfriend of the past seven years is a pre-op transgender female. When I met her she was just crossdressing, although she was living and working full time as a woman even then. Now after several years of hormone therapy and some surgical procedures, she is more beautiful and passable than ever. Fortunately we have a wide open relationship, and I continue to frequent escorts and prostitutes. I have just returned to Australia after nearly seven weeks in Thailand, where I spent about equal time in Bangkok and Pattaya Beach after a long time away due to Covid. I'm happy to report that, although things are a little different, there are still a large variety of gorgeous ladyboys available to satisfy my particular desires. After this latest trip, I have decided that I will move to Pattaya when I retire and live in a villa on the beach staffed with young ladyboys!

Good plan.

 

[Gypieman]

Wow!! that's what I call a my kind of party.Ladyboy's all around.Most be very nice.

 

[Gypieman]

Well for me i mostly am looking for a CD /or ST .Sometime when i'm out I look around hoping to see one walking around.If i see one i'll try to get her to notice me .Most of the time i have no luck.One time i saw one and asked for her number and she said no.I never saw her again.

 

[docisin]

Been searching for a long time for one that did it for me. Been to AmDam many times, and got close, but just didn’t happen…..where I’m living now, there are escorts and providers, but they just don’t look like they’d fulfill my fantasy about what I want (thanks, porn!). The search continues….

 

[RachelWalsh]

46 trans female here

 

[shymalea]

i just want to say to all admirers from sissies or CD,s,if you want to chat please do

 

[55ChevyBelAir]

I have told the story several times of how I used to chat with a pretty Filipina girl on an old defunct web site. One day she confessed to me that she was trans. I didn’t believe her so she showed me her cock. OMG when I saw it I wanted it which surprised her very much. We began a long cyber relationship in which I eventually helped her get out of cam modeling. I never met her in person but I have fond memories of her.

Now I am in a relationship with a beautiful transgender Filipina and I will be seeing her again in July. This is our fourth year together.

View attachment 2147930

I have told the story several times of how I used to chat with a pretty Filipina girl on an old defunct web site. One day she confessed to me that she was trans. I didn’t believe her so she showed me her cock. OMG when I saw it I wanted it which surprised her very much. We began a long cyber relationship in which I eventually helped her get out of cam modeling. I never met her in person but I have fond memories of her.

Now I am in a relationship with a beautiful transgender Filipina and I will be seeing her again in July. This is our fourth year together.

View attachment 2147930

Escierto, your Filipina girlfriend is very beautiful, with such pretty eyes and smile. It's a testament to the depth of your relationship that you have been together for four years. I hope your visit in July was very special.

 

[Escierto]

Escierto, your Filipina girlfriend is very beautiful, with such pretty eyes and smile. It's a testament to the depth of your relationship that you have been together for four years. I hope your visit in July was very special.

Thank you. I leave this morning to go back home but I sucked her magnificent cock and swallowed her sweet load of cum one last time. It was a good visit and I shall see her again in a few months. Until then we shall resume our routine of chatting on cam every day.

 

[55ChevyBelAir]

Thank you. I leave this morning to go back home but I sucked her magnificent cock and swallowed her sweet load of cum one last time. It was a good visit and I shall see her again in a few months. Until then we shall resume our routine of chatting on cam every day.

You're welcome. I'm glad you had such a wonderful visit and enjoyed your special intimacy. She sounds very special and your relationship is exceptional. Enjoy!

 

[Dearelliot]

Maybe I was 75ish, Bangkok, in a bar with a lady boi, quite an attractive woman. We went to an alcove and lay down for a while...I decided to go all the way. It was so amazing.

 

[7528Dick]

About a year ago. I went to an adult vid store. They had viewing rooms. Some with glory holes. Also 2 private viewing rooms with a couch. I saw a cd at the door and asked if I could come in. She said sure sweetie. I went in and got undressed, laid on the couch and she proceeded to suck my cock. She had on a cage so I went for her ass, pulling her panties aside and put a finger in her ass. This made her suck with a vengeance and another guy came in and jacked off watching us. I motioned him over and sucked his cock. This made me come in the cd’s mouth and he came in mine. So fucking hot. An hour well spent

 

[Escierto]

Maybe I was 75ish, Bangkok, in a bar with a lady boi, quite an attractive woman. We went to an alcove and lay down for a while...I decided to go all the way. It was so amazing.

Please tell us more if you don’t mind?

 

[cuckoldbill]

Love this thread