Questions: Ever consider entering the porn industry?

Nah, I'm too shy for that and once you enter you just never know where you will exit. I've considered starting my own site and model there for paid subscriptions. But how would I stay anonymous that way? I just think that once you get into porn then if you don't make it and try to find a regular job, you might run into some problems.

Question: Where is your list of blogs?

No idea. I don't know if you guys like these new blogger formats or the old designs are better? Let me know. Otherwise I'll just do whatever I want to do. Hmmm... that's what I'll probably end up doing anyway.

Question: I am greatly turned on by the milking fetish where women are milked like cows. Could you do me a TG comic in which a woman steals milk from a farm and as a punishment has to provide milk for the farmer by being milked by a milking machine?

Erm... wow! Love the imagination but this is really not my thing.

Question: HOOOOOOOOORAAAAY!!! Sasha back! Where've you been, sexy minx? Arooooga, Arooooga!!!

Classy. Are you in college? Don't you know how to behave? And most importantly, where is the frat house and when can I come in?

Question: I can't remember if you ever said if you were into manga/anime or not in a previous response...so here's a two part question. Are you into anime/manga and if so, do you read/watch a lot of Trap stuff?

I enjoy manga but I'm not a huge fan of it. I don't know the terminology of the styles but I enjoy the more adult stuff kind of drawing. I have not seen any trap stuff but I love trap stuff. I just don't seem to find much of that on the web. Any suggestions?

Question: sooooo.... when do we get to see you in your halloween outfit? (bounces impatiently)

You just did. :-)

Question: Out of all the actors to play 007, who is your favourite-Barry Nelson, who played him on US TV, Sean Connery, George Lazenby, Roger Moore, Timothy Dalton, Pierce Brosnan or Daniel Craig?

Sean Connery is an all time classic but I think I just enjoy him as a really good actor. For some reason Timothy Dalton has stuck in my mind as the image of 007. Daniel Craig is pretty good but I think he's more of a darker 007 just like the newer Batmans movies.

Girls, be good to your man tonight and keep your lips moist. Happy new year!


Question: I started dating this girl and my friend who once dated the girl told me she loves wearing Latex, but I am allergic to Latex. Should I tell and How?

Totally not. I think you should just wrap yourself on a latex condom for Halloween and when you have an allergic reaction that will scare the shit out of her. A Halloween she won't forget!

Question: You think waiting to your 18 requires justification? In less than 4 months I will be 31 and I still haven't been on a date much less touched a girl or a guy.

That makes you a highly valuable virgin. Ever saw the movie 30 Year Old Virgin? You too will nab a hottie when you least expect it!

Question: Could you do some pregnant caps?

Sure, who wants to try to get me pregnant?

Question: Mr. Enigma Mystery here again, Sasha. I saw the caption you referred to, but were you No.11, 16 or 3? Also, since boys as well as girls have breasts & mammary glands, why don't you write a TG comic in which a bad boy is punished by being forced to...

That was just an illustration... or maybe not. Maybe I'm one of the numbers but it's a mystery for you to find out. ;-) Remember that you really can't send essays through the formspring box. It cut of your message like a TG caption that cuts off boys' manhood.

Question: WHY do you have some of your images get obscured by some- thing that looks like a damn test card? Check out TG comic: witness-protection-fail and what SHOULD HAVE BEEN the 3rd image, and you will see what I mean.

No idea what you mean by test card. The TG comic looks and reads ok to me. I don't see any images being covered.

Question: Just went through all of your caps. it was interesting to see your progress, and how it all became increasingly more complicated. in your quest for the most expressive cap, dont forget how you started and make a simple one every now and then:) -LiEF & Ro

Glad you enjoyed it. I too agree that I progressed to a great complication and now I'm leaning towards the short and dirty pleasure.

TG caption: Cleaning house was a whole lot different for Sasha ever since she agreed to explore her feminine side.


Reader reveals her/himself!

For some reason people just love to share themselves with me. My fan mail! This is why I'm anonymous. So many internet freaks out there! ;-)


Question: If I wanted to dress like a girl, or was dressed as a girl when I met you, how would you react?

I'd be shocked... appalled... wait a second, are you hot looking? ;-) I'd probably be just surprised and would think it was great. What would you wear? Would we meet in the evening and you'd be dressed as a prostitute? Now, that'd be fun!

Sasha, I can suck myself off, how does that make you feel?

Who said America doesn't have talent? Oh wait... are you American?

Are u TG?


When did you first have sex?

I first had sex when I was 18 years old. I guess you can probably tell that I wasn't really the jock type so it took some time and effort to find that special girl. And, I just wanted to wait to be legal. Yeah, that's what I tell myself. ;-)

Hi, i was wondering if i send a pic of me to you, would you caption it and find a girl which you want me to turn into?

Go a-head email it to me.


TG caption: the last pill

This TG caption is just fresh off the press. Just made it right now. A picture of a super hot babe and the eternal question, what would you do if you were given the choice? 


Question: I love your TG Comics, Sasha. Is there even the remotest possibility that they might one day be downloadable, so the reader could take his time reading the comic at their leisure? And who is the mysterious Sasha ? I've got the hots for her!

Thanks for loving my TG captions so much that you want to download and take them with you all the time. At this time I do not have any way to put it together in a place so you can download the whole bunch. I can look into put at least the comics into a zip file and find a place where I can upload the file to share. I can try to do that when I got time.

Sasha is a figment of my imagination that comes to life from another realm into yours. She only visits us when you close your eyes at night or when you are on my blog. ;-)

Sasha, I have 3 questions. 1: What is the name of the Sasha model? 2: Where do you get your models? 3: Have you ever appeared in any of your TG comics, even disguised? Yours sincerely, Mr. Enigma Mystery.

Mr. Enigma Mystery, ooohhh that sounds like a double mystery to solve! The Sasha model's name is Sasha, sometimes she goes by the name of Sam when she doesn't want anyone to find about her or when she needs to function in the real world.

I get my models from surfing the web with all their free goodies. You have to thanks the internet for free porn! I remember sneaking in to check on my dad's playboys for the articles. That was so old school!

I believe I have appeared in one of my TG captions. I think it was one of my early Sasha schoolgirl captions.


TG caption: still-got-married

I don't usually read my TG stories when I repost them here but I remembered this one to be particularly good so I did... and I was right. It was hot. It's quirky, fun, flirty and with a great ending. Yeah, I can blow my own horn.


Question: I think it is very cute when a girl wears guy clothes. Do you ever walk around your apt. wearing nothing but one of your boyfriend's dress shirts and a coy smile?

I certainly would if I had a boyfriend, any takers? ;-) Please email me pics so that I can select one.

Question: Can i be a sissy with 16 years old?

You can be anything you want. That is a prime age to be sissified. The world tells you can do and be anything you want to do just be prepared to deal with the consequences... good or bad.

Question: My computer had a seizure and now it lost all it's memory. What if that happened to you? Your computer I meant... although it does work both ways.

If my computer lost all it's memory it would suck because I'd have to install everything again. I wouldn't really lose much because I'm anal and I have lots of things on a 2nd drive so I'd just have to use the back up. Oh, you meant my computer? It would be the same thing.


TG caption: That is your wife

A naughty TG caption about submitting to your desires. How a lovely wife helps her husband become all he wanted to be.


Question: Why don't you have any TG stories in which a brother is encouraged to dress up like a girl, and not punished?

Because to me part of the whole TG caption appeal is being punished, forced or found out. There is something about the thrill of the risk of doing something you shouldn't be doing.

Are you ever going to do a caption competition, where the funniest ends up in one of your stories?

Probably not. As you probably noticed I have slowed down a bit on the TG caption making process so I don't want to get anyone's hopes up.

I wore a bodysuit of a cute young college girl to a party cause I thought it would be cool and no one would know. My best guy friend happened to be there and he is trying to get into my panties, what should I do?

Put the bodysuit again and get fucked like the little bitch that you know you. You know you want it. Just make sure to come back and tell us all how it was.

My girlfriend first turned me on to crossdressing, I'm now very passable and incurably hooked. Recently she suggested she would like me to start taking Female Hormones. What are the side effects if any and can they be reversed?

Side effects is looking like a girl. Your success will vary depending on genetics. The longer you are on hormones there will be some things that will be harder to reverse.

Ha, ha, ha! Not data table, I said-look, I'll say it once more, in simple terms, this time. Is it possibe for me to date-you know, take the Sasha model to dinner?

Sorry, I'm in a relationship and I keep my internet life separate from my real world life.

Can you make a caption with my pic?

Yes, go ahead and email it to me.

Where do you shop for your transgender clothes?

Fortunately for me, I just go anywhere. I'm not a big guy so most girl stores have clothes that fit me. Online stores are amazon and even ebay. You can also shop online for the equivalent of all the brick and mortar stores, like Victoria's Secret, GAP, BR, Guess, etc. One of my favorite store is Forever 21 have nice sexy clothes that are very affordable.

Are you married?

I'm in a long term relationship.


TG caption: the-headpiece

An old school TG captions that starts like this, a long long time many moons ago, somewhere in the middle east a boy and a girl have a costume idea for the now called Halloween.


Question: When you started dressing up, what piece of female clothing did you wear first? I wore panties first myself.

I started with a pink bikini and then to cover myself like a proper beach bunny I had a tank top and a mini skirt. It was my mom's if you believe it, from her younger days. It looked just like the one below.

TG caption: an-improved-andrea

I made this TG caption for a friend some time ago. Her name is Andrea and she agreed to model for me for a cap based on my own real-imagination.


Question: Sasha, on one TG website, I found a Julia James comic strip. Do you have any idea what that site was called, and where do you get your models?

No idea. I searched google and shows there is one on Amazon? However, I'm pretty sure you did not mean that Julia. I get my models form the vastness of the internet.

Hello, Sasha, my name is Lamorak, & I love your TG comics. Is there any way I could buy one of your comics with English cash so it could be mailed to me?

Sorry but they are not published in paper format.

Did you know that boys and men have breasts and mammary glands of their own, and their milk is far more nutritious than a woman's milk?

I better start developing my mammary glands them.

As a woman, Sasha, do you think it's fair that women can wear mens' clothes, but men cannot wear womens' clothes? Also, have you thought of a caption competion for the viwers of your website?

Sure men can wear women's clothes. I do it all the time. I think fairness is a tough word. If you view all the other impositions and expectations and limitations that women still face today then a matter of clothes does not seem fair at all. Besides, aren't the biggest fashion designers men? So in a way women are wearing clothes designed my male minds. What are the ramifications?

Is the Sasha model datable?

I don't think I'd like to be put on a data table. ;-)

Question: Are you female and do you love giving head?

I'm female in my head some of the times. Does that count? I'm just poking some fun at you. If you go back and read my posts the answer to your questions will come through. I know, it takes work and work is hard. It is so much better to just sit back, relax and enjoy, right?

PS. No, I'm not female.


Question: Where do you get your models from? In particular, who is the Sasha model?

Who is the SASHA model? And will she be used for any story? Anonymous would like to know, because I think she's cute!

Sorry about the long question, Sasha, but where do you get your models from? I'd love 2 know. Your buddy, Anonymous.

Three questions asking the same thing? New readers? If you like the model Sasha very much then I suggest you to read my prior posts. Plenty of pictures of 'her' and you even might get to know her a little bit after you read all that stuff. I know... words hurt our brains. Sasha may be on some future TG captions if it strikes my fancy.

All other models I got their pics from the web (no particular website).

Hi, Sasha! It's me. Anonymous again. I came up with my own word for a woman's breasts, namely, Pleasure Pillows, because sometimes a woman or young woman will let a boy fall asleep with his head resting on her breast. Do you find it offensive?

There are so many names for breasts that it really doesn't matter. I don't think pleasure pillows offensive at all. It sounds kind of cute. Besides, if a girl lets you fall asleep on her breasts she must like you a lot. The question is do you like big or small pillows? And what shape?


TG caption: -whats-for-dessert?

Always wear a uniform when you're doing house chores.


Question: Hi! I'm Mr. Lamorak Korving. Sasha, if it was legal, and approved of by Society, would you work as a prostitute?

Sure thing I would. You say if it was approved by society... so does that mean it would be a profession just like any other hopefully without all the sleaziness and safety measures in place. So, yeah, why  not? Everyone loves sex right?

Sasha, a see you as stunningly beautiful woman with sexy and inviting come-to-bed blue eyes and a sensual mouth, measuring 36-24-35 inches, but have you ever made long TG Serials, like Annabelle Raven does?

I have not made any stories like she does. I looked it up and she is quite good. I just haven't had the inclination to write long text stories that are illustrated with pictures. Although, I do enjoy reading them quite a bit. Oh yeah, thanks for the compliments. You have quite an imagination. So, I'm a brunette with blue eyes? Something like this?

What if we saw just your eyes?

What if... I did... will... maybe. ;-)


TG caption: do-not-eat-donut-in-car

A fun TG caption about cars and donuts. Are you messy when you eat in the car? Do you eat in the car? Do all Germans don't eat in their cars? Do Americans eat McDonald's in the car? Do French eat 5 course meals in the car? Lots of questions!


Question: Would you ever show us your bulge? Like through some hot little boyshorts of yours?

I believe I already posted one in boy shorts some time ago.

Hi Sasha: I really, really enjoy the hooker fantasies. Can you please do more? Also, any blogs on the subject that you would recommend? Thxs, Brandy

Hooker fantasies are fun. I'll keep your request in mind. Unfortunately I do not have any other recommendations.

When are you going to update your comics tab?

When I make new comics. It may be some time. I'm without the inspiration and time to make long TG comics these days.

Dear sasha, It seems to me that you ONLY do tg stuff on this website... and not that tg isn't THE best thing in the world, but if that is all that you do eventually you will find it boring. I suggest finding ways to keep it new like:

(cont.) going forward with your tg stuff or finding the places where tg and other "topics" overlap. -hugs and kisses from a concerned friend.

Thanks for your thoughtful message. However it seems like the form ate most of it. So far this blog covers TG captions and comics and my own crossdressing adventures. I'd love to hear what other options you had suggested. I await your follow up suggestions.


Question: Have you ever thought of using your friends-male and female, in your TG stories?

No, out of respect for their privacy. At the same time, they would create another breadcrumb that could eventually lead to me. I enjoy my privacy too so that way I can be unprivate on the internet. There is some freedom when the consequences are vague and distant.


TG caption: perfect-in-every-way

A happy ending in my TG caption universe! Unbelievable!


Question: How long have you been involved in the TG scene? I'm a straight guy, so would you be offended if I wore female clothing? I am epileptic, 5ft. 8ins. tall, with a 39 inch chest and 36 inch waist and short-cut dark brown hair and dark brown eyes. Would [cut]

This would have been a curious question. Remember that formspring does not let you write essays when you ask me something so try to keep it short, otherwise you risk having your answer cut short. I have been interested in TG since I was a kid, so that is some years.

No, I'm not offended that you are a straight guy that wants to dress up. You are just like me. I'm straight'ish and I dress up. I think dressing up has little to do with who you want to have sex. Hmmm... let's say it is just complicated. Human sexuality is so complicated and we are all trying to make sense out of it, which is hard. Putting labels on something and categorizing will always be a generalization and what may be applicable to the masses may not be what it applies to you. So, yeah, it's complicated. Just have fun!


Question: PLAYING ALONG was a great story, but where do you get your models from?

Thank you and I hope you enjoy many more of my TG captions and stories. I just get my models from surfing the web for pretty girls in certain scenarios and stuff. I generally look around without having any TG caption or storyline in mind. Sometimes I save pics that I think I might use later. As you can tell this is a very unscientific method, it is much more touchy feely as I go along. You just never know when creativity is going to burst out and make a mess of everything. You just need to stay open and ride the internet waves. Surf's up!


TG caption: new daughter

On this TG caption, I love the look on her.


Question: Are you into futanari/TS women more than men?

Oh yes, futanari is pretty hot. It is all part of the m2f fantasy of being so feminine'ly sexy with a secret. I can only hope one day I'll look like her.


Question: do you derp at sometimes?

Maybe when something is really funny.


TG caption: pool potion backfrire

With the summer here, there is nothing like a swimming pool to quench the heat.


TG caption: niels-vs-sasha-and-anna

A fun TG caption I made some time ago for a very special German bimbo.


TG caption: hermosa

What could possibly go wrong when you want to ride a hot car? I made this TG caption some time ago but somehow got lost in all my files. It is about a boy that casts a spell that goes wrong or does it?