For men that have been with ts...

[MrsKellyPierce]

Did any of you after your first time, say never again?

If so, why? What made you change your mind?

Then after you did it the second time, was it due to being more secure or was the experience just better?

[SXFX]

Nope my firs girl Janice was a very nice girl, who was a total sweet heart.
Met her while at university. She was asian and stunning.
The only real time I've ever had an issue with dating a TS woman was not any issues with her or sexuality rather with the baggage I had and had brought into the relationship.

[dabaldone]

Sure did! And after the second time and the third time but it eventually got better.

[MrsKellyPierce]

Sure did! And after the second time and the third time but it eventually got better.
So yours was probably just nerves?

[Rusty Eldora]

Did any of you after your first time, say never again?

If so, why? What made you change your mind?

Then after you did it the second time, was it due to being more secure or was the experience just better?

It was almost a year of being very TS curious before I took the plunge in late Sept this year with a well reviewed escort. Was worried how I would react when first touching shecock, then sucking and being topped. Found I was drawn like a moth to it. She was first class and very feminine and I really enjoyed it, however I could barely sit down.

I saw my 2nd one a week later, I have now seen 4 different ones, with one twice. The I repeated with has been excellent, fun to be with and a turn on to me. The first two were quality women, the two later were doing it for money, didn't vibe female although they looked very passable.

Seeing someone like you Kelly would be fantastic, I haven't been that fortunate yet.

[BBaggins06]

Nope, I talked to some women online for a while first. When I decided to start dating, I went to an escort to see if it would feel right. It did.

[MdR Dave]

My "first" became my girlfriend for quite awhile. It wasn't weird.

[dabaldone]

Actually it was fear. We have been conditioned to believe trans-women are taboo. That if you engage in a sexual act with one you're gay. The fear of someone finding out amd being label drove me insane for a while. My first experince was in the 80's. No internet or social media to fall back on. I was on my own. The term trans-attracted has only recently been coined. It took years before I was comfortable with myself.

[amberskyi]

Its interesting how some guys never really seem to struggle with those feelings of fear or shame to any great extent.i wonder why that is? Maybe some of you guys who haven't really struggled with those feelings can chime in and explain how come?
I want to say its an age or experience thing but i know guys of various ages and experience who just seemed to automatically be secure or whatever.

[TSCURIOUS]

After the first - I wanted to see my second the same day. If I'm not in a relationship, I see TS more than GG escorts at thsi point.

[chloev69]

Ive been with quite a few now but have trouble being topped, Im really really tight and I sometimes bleed. BUT sometimes their beautiful cock feels so good in my ass I cum withouth touching myself. My other fave is tasting a beautiful gas sweet cum.

[Dino Velvet]

After my first time I wondered why I waited so long. Had a really good time with a hot girl who smelled great and I had sex with her pretty much the same way as with a GG.

[MrsKellyPierce]

Ive been with quite a few now but have trouble being topped, Im really really tight and I sometimes bleed. BUT sometimes their beautiful cock feels so good in my ass I cum withouth touching myself. My other fave is tasting a beautiful gas sweet cum.
Do you practice with a butt plug?

You should set one in there time to time, to keep yourself ready.

[chloev69]

I have tried, big and small but not regularly. Ive had a huge black she cock in in my ass and no problem and another time an average size and it hurt.
I guess i'll have to keep practicing:)
AVN here I cum!!!!!

I dream of yasmin or mia lol

[daltx_m]

nope. loved it every time

[RallyCola]

well, i do know someone that struggled with having his first experience for a long time then when he finally did it, he was filled with regret and said it was "gay." he tried to convince me that i should not indulge and that it was sinful and wrong. we are no longer friends but we have mutual facebook friends...he's married and quotes the bible often.

[559alphadog]

Ive topped twice, once in guam and once in thiland, I didnt mind I was buzzed my first time and sober the second.

[timid1]

Hi Kelly, no , after my first time I was elated! Only waited 3 days for the second time ,and I was so greedy I saw 2 girls in one afternoon / evening! I feared that it might be a bad experience before hand , and was very nervous ..... but the tgirl was wonderful . I just wished I'd taken the plunge when I was much younger!
Certainly the second time was better in terms of feeling safe and secure with the young lady, (it must be a bit nerve-wracking when you girls meet a fella for the first time?) and more relaxed!

[Rusty Eldora]

Its interesting how some guys never really seem to struggle with those feelings of fear or shame to any great extent.i wonder why that is? Maybe some of you guys who haven't really struggled with those feelings can chime in and explain how come?
I want to say its an age or experience thing but i know guys of various ages and experience who just seemed to automatically be secure or whatever.

There may be some self selection going on here, those that struggled or felt it was a mistake probably are not the type that hang out at HA. Those that had a good or great time are now pumped. I am sure I am in the 2nd group.

[bellamy]

No I only had about 3 hours in between first and second time and was gleefully counting down the seconds. lol

[timid1]

Its interesting how some guys never really seem to struggle with those feelings of fear or shame to any great extent.i wonder why that is? Maybe some of you guys who haven't really struggled with those feelings can chime in and explain how come?
I want to say its an age or experience thing but i know guys of various ages and experience who just seemed to automatically be secure or whatever.

Hi Amber,
I have to say I must be a bit of a softie. I can honestly say I was scared . Scared of taking my first step , scared that I wouldn't like the experience despite my fantasies and hopes, and honestly scared I would be ashamed of my actions . After 90 mins with a very lovely lady , I laughed that it had taken so long to take the first step , the experience was much better than I could of hoped for, and I felt really good about the whole experience rather than any shame. It felt right, felt special and something I wanted to try again. If I had taken the plunge when I was in my 20's I would of maybe settled with a TS? Who knows . In the last couple of months,I've met some really nice girls , with lovely personalities and kind dispositions.I felt my whole experience has been positive and uplifting sexually and emotionally.
Maybe because I am in my 40's I'm just ok with who I am? I certainly don't always feel secure , but you get used to knocks and learn to have an inner strength to overcome certain situations. Maybe when I was younger I just wouldn't of taken the step because of fear.
Don't know whether this answers your question adequately?

[blkmamba]

I struggles with it cause I know my marriage was done. Am not the one whos going to lie and keep it a secret. There no way I was going to put my wife through all and she would never andestand the way I feel. Specially being my wifey.

[amberskyi]

Hi Amber,
I have to say I must be a bit of a softie. I can honestly say I was scared . Scared of taking my first step , scared that I wouldn't like the experience despite my fantasies and hopes, and honestly scared I would be ashamed of my actions . After 90 mins with a very lovely lady , I laughed that it had taken so long to take the first step , the experience was much better than I could of hoped for, and I felt really good about the whole experience rather than any shame. It felt right, felt special and something I wanted to try again. If I had taken the plunge when I was in my 20's I would of maybe settled with a TS? Who knows . In the last couple of months,I've met some really nice girls , with lovely personalities and kind dispositions.I felt my whole experience has been positive and uplifting sexually and emotionally.
Maybe because I am in my 40's I'm just ok with who I am? I certainly don't always feel secure , but you get used to knocks and learn to have an inner strength to overcome certain situations. Maybe when I was younger I just wouldn't of taken the step because of fear.
Don't know whether this answers your question adequately?

actually it did and quite eloquently.you did have the immediate feelings of fear but i liked reading about your journey to acceptance.i wonder if it was really fear you were feeling or just a case of nerves about a new sexual experience.
i know when im going to be intimate with someone new im all nerves and awkwardness lol.of course im talking in regards to interactions within my personal life.when it comes to "work" its like a switch goes on lol

[amberskyi]

There may be some self selection going on here, those that struggled or felt it was a mistake probably are not the type that hang out at HA. Those that had a good or great time are now pumped. I am sure I am in the 2nd group.

theres quite a few guys on here actually who have struggled or are currently struggling with their attraction.its kinda what brings allot of people to this forum.a place to discuss and explore you know

[Amoore]

been with a few girls but only been topped once, and never again!

[bassman2546]

I had some nerves the first time. It took a couple of years for timing and logistics to work out before I had my first and only experience - but not the last. I enjoyed it very much (after the pain subsided. Damn, she was thick. Note to self. Buy a buttplug. Thanks for the reminder, Kelly).

I think about that next experience a great deal and will build on what I learned from the first to heighten the next, and the next... and the next.

[questioningone]

First was iffy and nervy for me but i topped and probably not too well. 8 out of 10 of my visits have been terrible experiencesand i have swore each time i would never try again. The 3 good experiences were pretty damn enjoyable and as a bottom, too. It's a good feeling being done well. BUT, i have stayed away for 5 or 6 years as a result of bad experiences. However i do still yearn for what is in my mind a great experience (a feminine girl with people skills who would enjoy doing me and enjoys themselves). Now, if either Kelly or Amberskyi wishes to step up to the plate.....

[Spittingboobs]

Never been in my life consider myself straight.
Now saying that many many beautiful babes out in the world.

But only one I would ever be with is allanahstar and yes I would allow anything and everything. She is the bomb

[amberskyi]

First was iffy and nervy for me but i topped and probably not too well. 8 out of 10 of my visits have been terrible experiencesand i have swore each time i would never try again. The 3 good experiences were pretty damn enjoyable and as a bottom, too. It's a good feeling being done well. BUT, i have stayed away for 5 or 6 years as a result of bad experiences. However i do still yearn for what is in my mind a great experience (a feminine girl with people skills who would enjoy doing me and enjoys themselves). Now, if either Kelly or Amberskyi wishes to step up to the plate.....

Sorry hun,i prefer to be the one getting done lol

[questioningone]

THAT works for me, too.

[bellamy]

I bet some of the issues are the fact that most guys first time with a ts is also with a prostitute which can add to the nervousness also

[reformedcharacter]

the first Ts I knowingly spoke to was a girl who supported the same soccer team as me but it was only after one occasion I saw her in the pub after a game and she tickled the top of my head as she said goodbye that I became curious.

Strictly speaking the first ts I had sex with was a post-op girl and it felt totally natural and just like with any other girl.

A few years later I took the plunge and met a pre-op TS escort and I only started to feel nervous when I thought that maybe once I saw her in the flesh that I'd find that I wasn't as into the idea of having sex with her as I fantasised.

Needless to say I found that not to be the case and afterwards it felt like I had made this amazing discovery and I couldn't wait to do it again.

To be honest I in my experience I feel like I connect more with ts girls than other girls which is the main reason why I've continued to see them I just wish there were more of them that you can meet in everday life rather than this relatively secretive world

[Spittingboobs]

Never been in my life consider myself straight.
Now saying that many many beautiful babes out in the world.

But only one I would ever be with is allanahstar and yes I would allow anything and everything. She is the bomb

Sorry was on the iphone hard to type so now on laptop.

To continue on from what i was saying.
If a guy decides he wants to become a girl and goes through with all this work to become what she is... The motivation and desire to succeed in life is strong.
So why cheat with your desires.

Reading so many threads here as to wanting a ts gf... and who would you want to be with etc..

Just do it stop wasting time in this once chance you got!

[timid1]

actually it did and quite eloquently.you did have the immediate feelings of fear but i liked reading about your journey to acceptance.i wonder if it was really fear you were feeling or just a case of nerves about a new sexual experience.
i know when im going to be intimate with someone new im all nerves and awkwardness lol.of course im talking in regards to interactions within my personal life.when it comes to "work" its like a switch goes on lol

Amber, I guess a combo of both fear and nerves? I don't enjoy Gay Porn generally, as there is a lot of aggression , whereas TS girls are far more feminine and generally more gentle ? Therefore (maybe my perception only) I felt less threatened, but a little scared nonetheless. (Scared of the " unknown"?) However , I take your point re: nerves about a new sexual exp. I'm nervous each time I meet a new girl for the first time. I've met 9 different girls, only one encounter was disappointing . We just didn't connect personality wise. However , her reviews on this site were generally poor, but she lived close by . I was hoping we might click, I usually get on with people , but she was exactly like the reviews said. All the other girls were friendly, and I really enjoyed the meeting. I've seen 4 of the girls at least twice, and have exchanged messages with a couple of the girls whose personalities I liked the most. I appreciate it is "business" for you girls at times, but I like to strike up a nice relationship if possible? It makes subsequent visits much for fun..... Hopefully for the girl too?!! And stops me being scared! X

[blckhaze]

Did any of you after your first time, say never again?

If so, why? What made you change your mind?

Then after you did it the second time, was it due to being more secure or was the experience just better?


I said never again, but because she was a hookup I knew nothing about. By the time I made the attempt for physicals i knew it was something i wanted long term just not what role id ultimately play.
My secodn time rocked mainly because it was with a girl who i knew more than just as a piece of flesh with a half way working brain.

[Kire89]

I think it's easy to become ambivalent, insecure and thoughtful after such an experience. I think that I've reflected long enough on this matter that my first time with a TS (assuming I see one that's recommended or get lucky with one that has no HungAngels "cred" (or is reviewed elsewhere)) will be wonderful. I look forward to the day it reaches fruition! :)

[spunkette]

I'd spent a lot of time using TS porn before taking the plunge with my 1st escort who was a TV. The experience was horny but unfulfilling given all the build up. It didn't put me off - just made me more curious. Feels like a long journey to find something - still travelling. Seem to have plenty of breaks on the way where I divert my energies to GG or football!

[txjr3]

Couple of ads in the back page of the local free rag causght my attention, and I followed up with a call. Had a great time, never looked back - now I think I prefer TS to GG, although I like 'em all. All started about 20yrs ago

[wiltthestilt]

I did it last summer. BJ both ways. It was a first time for me; and I was exhilerated during the lead up. The experience itself was OK. I chose the provider because she was very feminine and she had an established reputation. I wasnt overly attracted to her; not because of the cock, but she had a broader frame than I like. Services were very limited. Basically just the bj. I would have topped her, which was not offered. I would not bottom, which was offered. On the positive side I got hard and popped like normal and she was cool to chat with. She also got hard and came which I wanted.

With my curiosity satisfied, I am not motivated to do it again. Finding a TS who I find attractive, gets hard, and will bottom isnt easy and the few who intrigue me charge 2x to 3x as much as a gg. I only watch TS porn these days, but Im happy with gg providers. I am open to doing it again. I dont know when it will be though.

[brickcitybrother]

The first time was awkward... but hot nonetheless. But it was a long time before I did anything again. And it really takes being confident with yourself before you enjoy anyone or anything.

[Anubis1779]

Never had any negative feelings about it

[tomvan20000]

First time was a few years ago, Ive been pretty much TS exclusive since. To be honest though, my orgasms are much more intense with genetic women, but the build up is much better with TS, not to mention the latter get me going instantly.

[56k]

Did any of you after your first time, say never again?

If so, why? What made you change your mind?



It seemed that she was at the crossroads and could not figure which direction to go. She was a very depressed on not making more out of life. With the lack of affection & we meeting on a client/customer basis, I realised nothing would have escalated other client/customer relationship after a 6 month period in her eyes.

Being an Alpha male and adoring girls that offer a very girly character, my expectations may have been too much for her personality. To my dismay I assumed her girly looks would reflect her character. To this day (7 years later) I have a strong feeling she was a top and did not know how to keep someone interested that was not a top. She also had extreme difficulty explaining what would make her happy other than financial security.

I learned a lot from my mistakes and, quite certain I will have a second experience when the right one catches my eye.

[dryriser]

The first time was a bit of a disaster, she turned up slightly drunk, was out of condition and no longer looked quite like her pics (photoshop), she didnt have any condoms, I got very excited and came very quickly.
Undeterred I saw another lady about a week later, she got hard but considered herself strictly bottom.
The next one after that was again a bit overweight and past it, but fucked me in very positions before we both came.
I have seen various other ladies but have never really got used to being topped, although since the last time I have purchased a set of Butt plugs and feel very comfortable now with the largest in situ.
Im hoping to meet someone this week so I will find out then if Im prepared enough.
I dont as a rule like normal porn all the cocks put me off, however I do like T Girl porn and find it exciting.

[dodi67]

Well, my first was Allanah Star... Obviously, she did a very good job since I still enjoy shemale bodies every chance I get. I stoped counting long ago... Black, white, latino, asian... Uf, I love you girls!

[hwbs]

there is no turning back...maybe for a period of time but its almost impossible to completely quit....obviously it is different if u don't live in an are populated with a lot of ts

[DreadedFlower]

Well the title says "ts", so I dated with a male ts, a guy with a vag. :P It went well, but it showed me that I didn't like dating men.

[jennylicious]

Did any of you after your first time, say never again?

If so, why? What made you change your mind?

Then after you did it the second time, was it due to being more secure or was the experience just better?

I'm not a man, but as a very confused as a 17 year old I met the TS owner and main performer of a nearby trans bar who took me to her establishment and opened it up specially. It was on the floor of that bar I experienced my first and last time. There was nothing about it that felt right, and from the moment we started I just wanted it to end.

I never say never but:
NEVER!
NEVER!
NEVER!

It certainly sorted out some of the confusion.

[crsd1966]

- Did any of you after your first time, say never again?
Part of me said not to do it again, because of my family and religious upbringing, but it felt totally natural . It felt beautiful, like any other guy and gal.

- If so, why? What made you change your mind?
I felt much more secure, yes, but the experience was just as good: My first partner became my long-time GF.

[Dobladito]

My first time was great. First I went with this female prostitute and was so cold and meaningless. I went out and around the corner was this beautiful girl who was a ts, really nice and hot, I didn't doubt and went for her, it was awesome, didn't felt guilty or regret.

Later on like the second or third time I felt guilty and dirty, lots of nervous when going out looking for a girl, thinking if I'm doing wrong or not, what would people say, am I gay, am I bi, why is so attractive.

As time goes by, I started building confidence, experience and enjoying my taste in women. I like TS a lot, their beauty, the way the inside woman is expressed in full sexy as hell.

I'm going to watch a few more images and get back to work :wiggle:

[mwilliams001us]

Hi Kelly, I never thought of turning back...

[bhlaab]

Like many, my first time was with an escort. She was absolutely lovely, though I never went back. I think because she thought I would be into the dominant thing. Which, now that I mention it, it the most important thing I learned from that session: I'm not submissive!

[kmersh]

I never went out looking for a TS nor would I describe myself (at the time) as curious either, it was all innocent enough.

I was flying from Tokyo to Singapore and my seatmate (a rather attractive female) and I started chatting about Singapore, she explain how it was her first time visiting and how excited she was. I gave her some restaurant recommendations (as it turned out she is also a foodie) and we talked about business and such, the usual banter on an airplane.

Upon landing I offered her my mobile phone number in case she needed anything as I am an old hand at Singapore and know it almost like I know my home state. She thanked me for the restaurant recommendations and said goodbye, I figured that was the end of it and honestly never gave it another thought. I have had conversations like that before and it never amounted to anything other than a nice conversation aboard the plane (which is perfectly fine by me).

Low and behold two days later she calls me that she was done with her business meetings early and was dying to talk with somebody with an U.S accent. So I met her at a local coffee bar by her hotel and chatted for a while. Before I knew it, coffee turned into dinner and dinner turned into drinks at a favorite bar of mine.

By 11PM I said goodbye as I had early morning meetings the next day and besides, truth be told I am not into the whole one night stand thing, especially overseas. We ended up meeting for dinner and drinks the following three nights and agreed to call each other when we got back to the USA.

I got back 2 days to the USA after she did and almost like clockwork I got a txt message from her welcoming back the USA and welcome home. We talked on the phone for almost two weeks before I flew out to LA to have an "official date" with her.

After truly having a great time (and I do not generally have great times on dates) we start to kiss and her phone rings breaking the moment, after finishing her call, she drops me at my hotel and we say goodnight.

The next day she met me at my hotel for brunch and we again had a great time, talking, etc and she is as big a gear head (petrol head for you Europeans) as I am, what luck ;-).

We start to kiss again and she stops it and says that I need to know that she is a Transsexual and she hopes that I can be cool with that. I have to admit I was really unsure at first as I never EVER considered anything like that in my 10 year plan. However, I try to be open minded and said that I honestly think you are an awesome person and truly have a great time with you, so I am cool with it, but we are going to have to work up to the sex thing as I am still a little iffy on that.

She smiled and said that most guys would have turned and ran at full speed at that point, so no problem we could take things slowly. We ended up dating for two years (and it only took 3 weeks for me to become cool sexually with her being TS) until she got a V.P. position with her company in Korea and I was unable to leave the job I loved and we agreed to break up.

Honestly, once I was able to get over the idea of the penis down there, it was just as pleasurable for me, clearly the physics are different, but it become second nature so to speak.

k