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Old 01-02-2016, 04:27 AM   #1
MarkoAaron
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A question for femboys

I shared a little fantasy of mine today in another thread and it got me thinking.

For 2 years now, I've fantasized about having sex with a femboy. It all started when I met a femboy at a gas station, he's a cashier there. I've always talked to him when I've went in. Just small talk, never in a "Let's hang out sometime" kind of way.

I'm in my mid-20's and he's probably 19 or 20. I stalked him on Fb and I was blown away, he looks beautiful when he's dressed up. At work, he just looks like a regular, skinny boy. But on Fb, he has pics of him with make up on, wearing skimpy clothes and just looking sexy. He's about 5'7, 120 to 130 lbs. He has long red hair and wears glasses.

My problem is, I'm straight. I've never experimented with someone of the same sex, and to be honest, I've never looked at other guys in that way.

Femboys seems to be my exception, I've enjoyed pics online of femboys and dabbled in femboy porn here and there.

I've thought about asking him if he would like to do something, but without being so blunt and telling him the truth. I mean are straight guys a turn on for gay men? What if he is looking for a relationship? I refrain from relationships altogether, been single for 6 years by choice.

I literally have no idea of how to start the conversation with him, can a femboy give me advice?
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Old 01-02-2016, 07:54 AM   #2
Iwantitnowpleas
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Talk to him like you would a girl

That is what he wants. Look for an opportunity to tell him you think he is cute and would he like to grab lunch sometime. Being accepted for who he is inside will be huge. You don't ask out a cute girl looking for a relationship every time do you? I bet it's because you are sexually attracted.

What you have is a great opportunity. Girls usually only want sex when it suits them. A femboy has the same sexual needs you have...to get laid constantly.
treat him like the girl he is and you will be amply rewarded.

Good luck and let us know how it goes!
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Old 01-02-2016, 02:30 PM   #3
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Thank you. I'm gonna try and break the ice, the next time I see him.
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Old 01-03-2016, 07:16 AM   #4
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Pictures tell a story better
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Old 01-04-2016, 09:28 PM   #5
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You may want a quick re-think. You say femboy and say "him".

If it was me I would prefer to think that you think of me as "she" and an attractive person and find me cute.

Is "he" gay or is "she" TG?
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Old 01-04-2016, 10:04 PM   #6
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You may want a quick re-think. You say femboy and say "him".

If it was me I would prefer to think that you think of me as "she" and an attractive person and find me cute.

Is "he" gay or is "she" TG?
Don't you have to go with the appearance that is being projected at the time. He appears as a regular boy at work so maybe you have to go with 'him' there and then make changes based on appearance later. Depending on whether progress is made, MarkoAaron my have to tip his hand and state, "I saw your FB and I think you look special that way." If nothing happens then either go in stronger or punt.
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Old 01-04-2016, 10:09 PM   #7
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Don't you have to go with the appearance that is being projected at the time. He appears as a regular boy at work so maybe you have to go with 'him' there and then make changes based on appearance later. Depending on whether progress is made, MarkoAaron my have to tip his hand and state, "I saw your FB and I think you look special that way." If nothing happens then either go in stronger or punt.
Fair point, as long as everything works out for the best
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Old 01-04-2016, 11:32 PM   #8
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However you approach it, be respectful, this is real life and not a story on Lit. Whether you approach them as her or him, remember it is a real person with feelings and insecurities.
Only bring up their FB in private, you have no idea what their situation at work is.
A little damage can last a very long time
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Old 01-04-2016, 11:42 PM   #9
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Quote:
Originally Posted by MarkoAaron View Post
I shared a little fantasy of mine today in another thread and it got me thinking.

For 2 years now, I've fantasized about having sex with a femboy. It all started when I met a femboy at a gas station, he's a cashier there. I've always talked to him when I've went in. Just small talk, never in a "Let's hang out sometime" kind of way.

I'm in my mid-20's and he's probably 19 or 20. I stalked him on Fb and I was blown away, he looks beautiful when he's dressed up. At work, he just looks like a regular, skinny boy. But on Fb, he has pics of him with make up on, wearing skimpy clothes and just looking sexy. He's about 5'7, 120 to 130 lbs. He has long red hair and wears glasses.

My problem is, I'm straight. I've never experimented with someone of the same sex, and to be honest, I've never looked at other guys in that way.

Femboys seems to be my exception, I've enjoyed pics online of femboys and dabbled in femboy porn here and there.

I've thought about asking him if he would like to do something, but without being so blunt and telling him the truth. I mean are straight guys a turn on for gay men? What if he is looking for a relationship? I refrain from relationships altogether, been single for 6 years by choice.

I literally have no idea of how to start the conversation with him, can a femboy give me advice?
I think it's safe to assume that you've he has been the object of your masturbation fantasies. My question is, do you fantasize about him as a young man or as the female person who he projects to be in his facebook pics?
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Old 01-05-2016, 04:17 PM   #10
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I think it's safe to assume that you've he has been the object of your masturbation fantasies. My question is, do you fantasize about him as a young man or as the female person who he projects to be in his facebook pics?
Honestly, it's kinda both. I've always identified as straight, this new feeling is both exciting and scary. It's something I've never really experienced in my life.

Seeing him "all girly" undoubtedly made me curious. I fantasize about it so much, because it's something new and I'm surprised by how much it gets to me. I learned through a mutual friend of ours, that he is gay. He's comfortable with his sexuality, but says he has a strong feminine personality.

Living in a rural town where gay marriage is still a heated subject, I guess he chooses to hide that in his work life. My friend told me he was really shy, but she was gonna talk with him about meeting a guy. She isn't gonna tell him who, but I think he'll be surprised when he finds out it's me.

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Old 01-05-2016, 05:08 PM   #11
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The thing to avoid is building up any pre-conceptions - that's true for any prospective relationship, huh? It'll be so much fun finding out about each other. I think you're being quite sweet about this - mind you don't get eaten alive . It sounds like you're doing the right thing so far and it shows from what you've said, that you are being very respectful
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Old 01-06-2016, 12:46 AM   #12
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Got home from work and received GOOD NEWS! Our mutual friend, Lindsay, talked to him today and convinced him she had a guy-friend that thinks he's cute and wants to hang out.

He wouldn't agree, unless he knew what I looked like. The cat is out of the bag. We added each other on FB and we talked for awhile. He was in disbelief, because we see each other almost every week. I told him I was nervous and didn't know what to say; plus, this is all new to me.

He understood. He also invited me to our friends house, tomorrow. We're gonna hang out and see what happens.
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Old 01-06-2016, 12:52 AM   #13
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Originally Posted by MarkoAaron View Post
Got home from work and received GOOD NEWS! Our mutual friend, Lindsay, talked to him today and convinced him she had a guy-friend that thinks he's cute and wants to hang out.

He wouldn't agree, unless he knew what I looked like. The cat is out of the bag. We added each other on FB and we talked for awhile. He was in disbelief, because we see each other almost every week. I told him I was nervous and didn't know what to say; plus, this is all new to me.

He understood. He also invited me to our friends house, tomorrow. We're gonna hang out and see what happens.

Hey ....way to go....good luck and hope it all works out
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Old 01-06-2016, 01:25 AM   #14
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Great to hear. Would love to chat more with you over pm if your interested would love to get more info from you. feel free to pm me
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Old 01-06-2016, 05:21 AM   #15
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Originally Posted by naughtyinsilk View Post
However you approach it, be respectful, this is real life and not a story on Lit. Whether you approach them as her or him, remember it is a real person with feelings and insecurities.
Only bring up their FB in private, you have no idea what their situation at work is.
A little damage can last a very long time
Naughty - that's great and caring advice. I feel its too easy to forget real life and real people sometimes when we read on here. Nicely put.
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Old 01-06-2016, 06:03 PM   #16
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Originally Posted by MarkoAaron View Post

He understood. He also invited me to our friends house, tomorrow. We're gonna hang out and see what happens.
Is he going though as himself or her? Are you attracted to him or to him as her?
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Old 01-06-2016, 09:18 PM   #17
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Tonight was really a new experience. I went to my friends house to meet my new, femboy friend.
His name is Brilee (birth name Bryan).

I went to my friends house and I was the most nervous when I parked and walked up to the door. My friend opened the door, when I was still on the steps and she smiled, real big at me.

I walked in the living room and there he was, leaned back on the couch with his legs crossed. He smiled, but didn't say anything. I noticed he was playing with his fingers, not really making eye contact with me.
I sat in a chair across from him. Obviously, we were both nervous. My friend eased things up for us, saying 'here we are, finally', and laughed.

With her in the conversation, it made things a lot easier. We all soon got to talking and getting more comfortable. We talked for maybe half an hour; my friend, Lindsay got her jacket and said she was gonna go out for awhile and leave us to "get acquainted."

After she left, we were quiet, again. I asked him if he was ok, he said yeah, he was just nervous. I went over and sat beside him and started talking about anything that came to mind. We talked for a bit about him and his decision to become to a femboy.

He said, he knew he was gay at a young age. The femboy stage didn't start until he was a sophomore, he was always a petite guy and felt more feminine than masculine. At that moment, I told him, he was a very pretty femboy. He smiled at me and said, thank you!

We kept talking for a bit, he didn't seem to mind or maybe didn't notice, my hand on his knee, rubbing it. It got real, when he laid his hand on the inside of my thigh and started rubbing up and down. He asked what I had in mind?

I was blunt, I told him I had a sexual attraction to him and I hoped we could have some fun.
He said, he'd like that, he had a nervous smile and kept giggling. I put my hand on the back of his neck and brought him closer, and we kissed. During the kiss, I rubbed my hand on his lower back and then starting grasping his ass.

To make things short, he gave me oral sex; he leaned over the arm rest of the couch and I fucked him for a few minutes.

It was my first time with someone of the opposite sex. I wouldn't say that I'm ready to switch teams, but it's certainly something I wouldn't mind doing again.
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Old 01-06-2016, 10:07 PM   #18
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Nicely done!
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Old 01-07-2016, 01:56 AM   #19
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You don't have to switch teams. But for society disapproval, very probably many more guys would be bi. ....and just like with women, pay attention to their needing to orgasm, and it's a whole lot more fun.
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Old 01-07-2016, 05:40 AM   #20
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Awesome! That's great to hear

Also, would you mind turning on IM? I have a private question for you
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Old 01-08-2016, 05:22 PM   #21
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Good to hear it went well and hope it develops. Now to find a nice guy for myself lol
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Old 01-08-2016, 06:26 PM   #22
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Good to hear it went well and hope it develops. Now to find a nice guy for myself lol
Hello sweety. Care to get a conversation started with me?
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Old 01-08-2016, 08:29 PM   #23
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Hey MarkoAaron, don't leave the gurl hanging. Make some follow-up contact. People need to feel like they are human beings and are not being taken advantage of.
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Old 01-08-2016, 08:50 PM   #24
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Hey MarkoAaron, don't leave the gurl hanging. Make some follow-up contact. People need to feel like they are human beings and are not being taken advantage of.
Very true
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Old 01-08-2016, 09:43 PM   #25
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This is such a touching thread Marko, thanks for sharing your journey.
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