Sissy Boy

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Oday

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Oct 21, 2017
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Hi sandy I want to ask you what girls think about sissy boys and how to turn into a real sissy boy?
 
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Hi Oday, I am really not the person to ask since I have never really known any in real life. Sure I have several gay friends and know a few cross/dressing-transgender types but no sissy boys. Sorry , maybe others can help answer this question.

Sandy
 
Oday said:
Hi sandy I want to ask you what girls think about sissy boys and how to turn into a real sissy boy?
If I may. I'm sissy boy nowv24. I have been sissy prolly since 13. Full time sissy/she ale since 15. As name says I went to proms as a girl. That was to do that AS a certain gender rather than just a CUTE sissy boy. Also to please my dateso he would be with a nice looking sexy GUrl. Not a x dresser. Girls are fascinated by sissies and all girls and women want to have at least one good sissy friend. I hope that is not a fad or a trend.
I do want to ask one thing for myself. I'm 24 and men are getting more n more interested in me'. I'm a boy who looks more like a girl. I guess I want to ask if I should be more aggressive about pursuing men or keep letting them come to me?
Luv, Mary real n legal name now.
.
 
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Hi Ms. Mary,

Regarding your question:
18mDresdF4prom said:
..... I'm a sissy-boy, now 24. .......... I do want to ask: Men are getting more-n-more interested in me. I'm a boy who looks more like a girl. I guess I want to ask if I should be more aggressive about pursuing men, or keep letting them come to me? Luv, Mary (real-n-legal name now).
You will need to answer this question for yourself, of course.... maybe you have already. Anyway.... I suggest making decisions about how to proceed based on what a given man of interest knows a-priori.

If he thinks you're a woman, then finds out in his or your bedroom that you have a penis — i.e., he's surprised to discover you're a shemale — that could result, conceivably, in an unpleasant or even violent response. Thus, if you find him desirable, I suggest proceeding in a delicate and tactful way toward educating him about your sexuality, making judgments along the way about how he's responding. If you sense his response toward the whole concept of shemales is hostile, I would suggest breaking it off and not proceeding further, just as you would with any man you sense doesn't like you.

If, on the other hand, a given man of interest knows in advance you are a shemale, and you find him attractive, then hey — go for it. In a case of this nature, I suggest going about seducing him in the way a woman typically would — not beating him over the head with your desire to get him in bed, but.... well, you know.... getting him there anyway.

Good luck!

—Custer
 
Custer's, Ty for your thoughts. I try to let a stranger know I'm a boy before he tries to kiss me. That has been what works for me. I've not decided my own answer yet. But hoping for more input. I do naturally look female but hormones have done pretty well for me. 1st the hips 8-10 years ago. Breasts This size about 3 years ago. My own dad died 3+ yr ago. I do wish he could have seen me developed! 33C-29-41.
Love Mary
 
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Custer Laststand said:
Hi Ms. Mary,

Regarding your question:

You will need to answer this question for yourself, of course.... maybe you have already. Anyway.... I suggest making decisions about how to proceed based on what a given man of interest knows a-priori.

If he thinks you're a woman, then finds out in his or your bedroom that you have a penis — i.e., he's surprised to discover you're a shemale — that could result, conceivably, in an unpleasant or even violent response. Thus, if you find him desirable, I suggest proceeding in a delicate and tactful way toward educating him about your sexuality, making judgments along the way about how he's responding. If you sense his response toward the whole concept of shemales is hostile, I would suggest breaking it off and not proceeding further, just as you would with any man you sense doesn't like you.

If, on the other hand, a given man of interest knows in advance you are a shemale, and you find him attractive, then hey — go for it. In a case of this nature, I suggest going about seducing him in the way a woman typically would — not beating him over the head with your desire to get him in bed, but.... well, you know.... getting him there anyway.

Good luck!

—Custer
Custer, You make a great point about being sensitive about your partner and his expectations. I am in the "awkward place" of femmed cuckold which in some ways may be easier than being single and dating, as far as sexual partners. I feel for those who are seeking partners, as I can understand the attraction and desire being around black men. Though it SEEMS as though more black men (as a cultural phenomena) are ok with using a white sissy boi as they would use a white woman.
 
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Hi Ms. Mary,

Re.:
18mDresdF4prom said:
Custer's, Ty for your thoughts. I try to let a stranger know I'm a boy before he tries to kiss me. That has been what works for me. I've not decided my own answer yet. But hoping for more input. I do naturally look female but hormones have done pretty well for me. 1st the hips 8-10 years ago. Breasts This size about 3 years ago. My own dad died 3+ yr ago. I do wish he could have seen me developed! 33C-29-41.
Love Mary
You're welcome. And, it sounds like you've successfully become a hot-looking shemale*. Congratulations!

—Custer

*Corrected from an earlier automatic misspelling by the word processor.
 
Last edited:
Hi Littlehubby4,

Thanks for your reply. Re.:
littlehubby4 said:
Custer, You make a great point about being sensitive about your partner and his expectations. I am in the "awkward place" of femmed cuckold which in some ways may be easier than being single and dating, as far as sexual partners. ....
By this do you mean, you are your wife's cuckold and dress like a woman (wear dresses, skirts and blouses, etc.), but are more-or-less obviously a man...?

Or, do you mean you are your wife's cuckold, and you've taken hormones, have broadened your hips, had breast-enhancement surgery, wear dresses or skirts and blouses, etc., such that you look like a woman, but in reality are a shemale with a penis?

I ask because the concept of "feminization" seems to involve various alternatives. Whichever is the case, I gather it's in accordance with what your wife desires for you....?

—Custer
 
Custer Laststand said:
Hi Littlehubby4,

Thanks for your reply. Re.:

By this do you mean, you are your wife's cuckold and dress like a woman (wear dresses, skirts and blouses, etc.), but are more-or-less obviously a man...?

Or, do you mean you are your wife's cuckold, and you've taken hormones, have broadened your hips, had breast-enhancement surgery, wear dresses or skirts and blouses, etc., such that you look like a woman, but in reality are a shemale with a penis?

I ask because the concept of "feminization" seems to involve various alternatives. Whichever is the case, I gather it's in accordance with what your wife desires for you....?

—Custer
Yes, correct as to what my wife wants, I call it "awkward" because of our lifestyle and public situation. Due to my wife & her bf's professional situation we must remain discreet. Given that, even though privately their desire for each other while cuckolding me. The hormones were my choice rather than being in chastity, the estrogen levels sufficient to inhibit male masturbation, but not high enough for significant breast growth, this way Cassandra & I can still portray ourselves as husband & wife.
The positive side effect has been much reduction of genitals which allow me to wear panties, with typically wearing yoga pants here at home, and for frequenting bar/nightclub wearing skinny jeans with barely any noticeable mound from what is left, very feminine. My nipples are enlarged and puffy, highly sensitive but not overly enlarged. Hope that gives you a better idea. Thanks for the inquiry though, its much appreciated Custer
 
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littlehubby4 said:
Yes, correct as to what my wife wants, I call it "awkward" because of our lifestyle and public situation. Due to my wife & her bf's professional situation we must remain discreet. ....... etc ....... Thanks for the inquiry though, its much appreciated Custer.
You're welcome, Littlehubby4. Thanks for the clarification regarding what 'feminization' means in your case. It sounds like your approach to that has worked, and continues to work, in the case of you, your cuckoldress wife and her lover.