Man having sex with a transgender women?

Discussion in 'General Sex Discussion' started by amazing_blue, May 5, 2015.

  1. amazing_blue

    amazing_blue New Member

    Joined:
    Nov 1, 2014
    Messages:
    3
    Likes Received:
    3
    For the past few months I have been dating a very lovely transgender woman. I'm not the kind of guy who chases those types or sees himself with them, it just kind of happened. We had a class together..she is fresh from the great country of Brazil and didn't speak English too well so I offered to help out. An absolutely gorgeous girl with a great figure and (go figure) big big booty. Studying turned into lunch which turned into dinner over time. On one of our early dates, she made sure that I knew she was transgender before we proceeded any further. I was pretty sure she was transgender. I told her I was completely fine and supportive of it. I was just too crazy about her to care. She has such an angelic personality and is very feminine. She likes to wear high heels, mini-skirts and halter tops. She likes to wear thong bikinis and tan her booty in the sun. We have since held hands, kissed and made out on a number of occasions. I enjoy holding her in my arms. I have felt her penis through her clothes on a few occasions, both erect and flaccid. When she sits on my lap I sometimes feel her balls. It was a little shocking to me at first but not in a bad way. The couple of times I've seen her in a thong bikini, I could definitely tell she had male parts down there.

    This weekend her parents are out of town on big business and she has her house to herself. She is inviting me over for a "special weekend" which means we will likely have sex for the first time. I'm just wondering how to approach it. I'm still a bit apprehensive about her having a dick but I like to think it will not be too much of an issue. She likes that I am very much a straight guy and not someone who likes her because of that. She has said that she attracts many bi/homosexual men who like her because she has a dick. She kicks them to the curb.

    I feel like I can't assume that she's into anal just because she's transgender. If she is I'm guessing that I would penetrate her that way. If she isn't I'm guessing I could just rub my dick between her legs to get off. And I know that at some point her cock is going to come into play and I really have no idea what to expect. Any insight would be appreciated.

    She's going to Brazil for 3 weeks in August and is hinting that she wants to bring me with her. By that time I would like to be fully comfortable having sex with this beautiful, special woman. How do I please her?
     
    phish likes this.
  2. rcc8611

    Gold Member

    Joined:
    Sep 30, 2010
    Messages:
    426
    Likes Received:
    553
    Gender:
    Male
    I'd say start with oral on each other and touching. She may be bottom being the fem but if not get off by oral. Have to admit that's a fantasy of mine bad
     
    phish likes this.
  3. billytk1977

    Verified Gold Member

    Joined:
    Mar 18, 2015
    Messages:
    956
    Likes Received:
    908
    Gender:
    Male
    Location:
    Metropolitan
    I may honestly be the last person in the world that should respond to this, i have never met a transgender person. But in all honesty the only thing i can say is what i would tell anyone starting a relationship reguardless.

    Don't force her to do anything she is not comfortable doing, on the same token however don't allow yourself to do anything you are not comfortable with.

    Take your time and most importantly, have fun. If you enjoy her, and want to be with her take it easy, what will happen will happen.

    And good luck, i hope you enjoy your weekend.
     
    10_3XL, phish and whybother like this.
  4. HotForHoney

    Gold Member

    Joined:
    May 9, 2013
    Messages:
    16,922
    Likes Received:
    17,177
    Gender:
    Female
    Location:
    North East USA
    I think she is fortunate to find someone understanding. Not sure I could.

    Best advice - communicate. Talk about what she wants first.
     
  5. phish

    Gold Member

    Joined:
    May 7, 2010
    Messages:
    1,354
    Likes Received:
    1,309
    Gender:
    Male
    Location:
    Central PA
    Good luck. Maybe start out with Kissing that might get things going... Just have fun.
     
    billytk1977 and Tonystarkxxx like this.
  6. Redline1

    Gold Member

    Joined:
    Jun 13, 2013
    Messages:
    497
    Likes Received:
    677
    Gender:
    Male
    Dude!!! Take your time just like you would with a female. Go with the flow and have fun with her!!! Try to stay relaxed and enjoy the moments!!! I too have this fantasy and would love to hear about your weekend!!!
     
  7. Doitagain

    Verified Gold Member

    Joined:
    Jun 13, 2014
    Messages:
    3,994
    Likes Received:
    6,596
    I've never been in that situation but honestly you sound sincere and respectful. I guess just take it slow like you have and talk to her. Good luck , good for you two , and have fun.
     
    HotForHoney and billytk1977 like this.
  8. wrangler

    Gold Member

    Joined:
    Apr 30, 2010
    Messages:
    103
    Likes Received:
    698
    Gender:
    Male
    Location:
    Australia
    Don't over think it ..... Follow her lead
     
    ply and billytk1977 like this.
  9. johanconra

    Gold Member

    Joined:
    Jan 17, 2015
    Messages:
    152
    Likes Received:
    491
    Gender:
    Male
    Location:
    Netherlands
    Stop thinking to much about it, if you start worrying it'll just get worse.
     
    ply likes this.
  10. Candela

    Verified Gold Member

    Joined:
    Dec 13, 2014
    Messages:
    4,867
    Likes Received:
    7,448
    Gender:
    Female
    Just get down on your knees,and show her how its done!!!!!

    ps..In all reality,She is lucky to have found someone like you!!..Good Luck xo
     
    Bambidaaarvark, ply and billytk1977 like this.
  11. ply

    ply
    Gold Member

    Joined:
    Jul 15, 2011
    Messages:
    1,032
    Likes Received:
    430
    Location:
    Alsaks
    Not forcing your partner into doing something they do not want to gets way to much airplay. Grab him by the back of the head just like you would any other gal - or like any other gal would do to you.
     
  12. billytk1977

    Verified Gold Member

    Joined:
    Mar 18, 2015
    Messages:
    956
    Likes Received:
    908
    Gender:
    Male
    Location:
    Metropolitan
    Ply, while i agree that there is a time for that he made it clear that this relationship is just starting, if he was to do that right off it may not end well.
     
  13. AGFUNK

    Gold Member

    Joined:
    Dec 28, 2010
    Messages:
    3,974
    Likes Received:
    3,237
    Gender:
    Female
    Location:
    IL
    Her, you referred to her as a he and she is not just because she has a penis.

    Just take it slow, kiss, talk about it before hand if need be. Hope you both have fun!
     
    ply and billytk1977 like this.
  14. 10_3XL

    Verified Gold Member

    Joined:
    Apr 11, 2014
    Messages:
    8,236
    Likes Received:
    9,544
    Gender:
    Male
    Location:
    Idaho, USA
    I think everyone else has pretty much already said it:

    Communicate, take your time to "get a feel" for each other, don't force anything, and (most importantly) enjoy yourselves.
     
    billytk1977 likes this.
  15. mactheripper

    Gold Member

    Joined:
    Mar 29, 2014
    Messages:
    270
    Likes Received:
    319
    Gender:
    Male
    Location:
    California

    The fact that she likes that you are straight tells me he enjoys being a woman and will most likely want you to penetrate her anally.


    Have fun dude and give us an update. My homie had sex with a transgender in Mexico and he says it was the best experience he has ever had.
     
  16. woodster

    Verified Gold Member

    Joined:
    Jun 24, 2014
    Messages:
    608
    Likes Received:
    561
    Gender:
    Male
    I really like your openmindedness and that you look at the person first. it is refreshing to see. have seen some very attractive transgender people and thought about it myself. your moving on it with no hangups. good for you. have a delightful time of it!
     
    Ashli likes this.
  17. Redline1

    Gold Member

    Joined:
    Jun 13, 2013
    Messages:
    497
    Likes Received:
    677
    Gender:
    Male
    How did the weekend go?
     
    woodster likes this.
  18. Ashli

    Ashli Member

    Joined:
    Sep 3, 2016
    Messages:
    36
    Likes Received:
    50
    Gender:
    Female
    Location:
    Texas
    As long as you see her as a woman, and not only a sex object like many men do.
    Ashli