Hello, I identify myself as straight and have always only had female partners. But sometime back I saw a dream where I was crossdressed by two girls then sucked cock while being pegged by the girls. I freaked out. I thought it would be one off. Then within the last month I had two similar dreams. So now I am thinking of giving it one try though I am not quite sure. So girls can you give me inputs on how to turn myself into a passable girl both dress up and make up? What all do I buy? I have crossdressed only once before and the dressup was done by a female friend so I have no clue as to what to do. Also I don't know people in the city I relocated to so can't get any help and will probably have to do it myself. I think I will give the crossdressing a try and then think about the rest of the stuff. Any girls want to give some suggestion or would like to dress me up?
The cross dressing I can't give any advice on as I've never had any desire to do so but the cock sucking I have decades of experience with. If you have thoughts of, or the desire to suck a mans cock and get the chance to do so I say go for it.
I love cross dressing! I just recently started about 6 months ago. I went out in public for the first time last week. Pretty sure I was passing. I’ve also been with a man but it was well before I ever dressed. Both are awesome in my opinion. I’m definitely looking to combine the two.
Wow this was well over 2 years ago. I am now trans and on hormones and have had a couple great sexual experiences dressed and it’s awesome. I’m not quite out but am getting there. When a man treats me like a woman it’s exhilarating
I would expect it's pretty exhilarating for the man, too, but that's a guess. Nice profile pic, Toni.
I have dressed up in my wife's dresses, bras, and panties. She does my makeup, and I really look like a woman. I'm fairly tall at 6 ft and roughly 160lbs, but I'm pretty hot dressed up. I've been with several guys while dressed up, and going into a bar. I always tell any men that show interest, that I have a dick. Even the straight guys still go for me. Being bent over, panties around my ankles, and dress pushed up, feels so feminine to me. I've thought about doing the change recently, but haven't talked to my wife about it yet. She loves seeing me with men, but I'm not sure how she would feel if I decide to go through with it.
Many years ago I went to a college party. I have never been charming enough to attract women of any size or shape. After my senses were numbed by several beers I asked a lady to dance because she was alone also. It was like a dream as she responded very quickly and suggested that we go to her apartment to get aquatinted. I was too naive not accept the offer. At her apartment we had another beer and sat on the couch. She was as fast chested as me, so I decides that I would make a move without involving her breasts. We started making out seriously, and she climbed up on to my lap. She was wearing a knee length skirt. I decided to check her out by slowly sliding my hands up her shirt. She offered no caution nor resistance. I should have been suspicious at this point. My hand completed the advance and ended up touching the hardest boner that I gad ever imagined trapped in some sexy black panties. Panic ensued and I got up bouncing him on the couch. I walked out as fast s I could and never looked back. I will never forget the event and how stupid I was to think that sex with a woman is a matter of luck.
I would never do that to anyone. It's only fair every man that likes what he sees, knows before hand that I have a dick.
How did she deceive you? Did she ask you to dance? Did she get you intoxicated? Did she tell you she was a cis woman? Definitely why I avoid bars, parties and alcohol especially drunken people I don’t know or hook up with random people. I have publicly listed that I am a trans woman and all someone has to do is look at my profile page. I still have people that initiate chats with me that get upset that they didn’t look at my bio. I shouldn’t even have to because you know how many of those people had anything in their bio??? NONE. I looked and you have nothing in your bio either. So why should we have to announce that we have something you don’t find appealing when you initiate contact and leave who you are a mystery? There are literally tons of men and women who find dating a trans woman normal and that’s who they go for. And many more who fetishize us or are curious. We don’t have to be deceptive my inboxes are FULL of men that know exactly what I am and would love to sweep me off my feet. Don’t worry nobody’s going to blatantly trick you into anything unless they’re a rapist and there’s far more cis men then trans women that meet that criteria.
Should you go ahead and suck cock? Hell, Yes! Always suck cock no matter what you are wearing or not wearing.
As a crossdresser myself, it would be a great thrill to be treated as a woman while dressed. Then show him how sexy and insatiable this ‘woman’ can be.
Prefer to be treated as a woman but don't have the body to be passable at all... But to submit and please a man is such a turn on and so gratifying even if I don't cum knowing that he is pleased and satisfied is wonderful and very satisfying to me
Like a lot of different thing we have done in the past, crossdressing is one of them, influenced by the movies. My wife wanted to transform me into a woman for a couple of reasons.She wanted to dess me up, wig, makeup and clothes and I gladly allowed her to play. She went all out, shaved me down and treated me like her little doll. As fucked up as it sounds, I was rock hard and drouling cum the entire time. I made love to her, as if I were another woman and later she fucked my ass with her strapon. Role reversal was fun, but I couldnt stand the itch of my hair growing back. Makeup, wig and pantyhose a couple of times after, but never went out like that.
Dear Pretty Toni: My Experience was from a long time ago. I had never heard of the terms Transgender, Crossdresser at that time. We did use the term Sissy for young men who dressed like girls and liked fellatio. I was not a very popular young man, and found relationships with women very difficult to create. That was my only experience with a male in any form. Most guys at that time would have punched her on the jaw. I chose to run away as fast as I can. I now have a god son who is in a gay relationship and has a very successful career. I enjoy seeing him every time that he is in town.
Maybe it's just my thoughts, but I feel that when i am dressed up and shaved smooth everywhere, it just feels correct. It feels even better with a guys dick in me...mouth, ass, anyway I can get it. I've started to have urges lately. It feels like something is missing, and at the same time, it feels like i need to cum. Butterflies in my abdomen area, and tingling in my ass....A man's cock in me while I am dressed as a woman fills that urge.
I’m more of a woman and for the most part it’s not exactly sexual. The first time I was dressed it was very erotic and the first time I was with a man as a woman I was aroused the entire time even just on the couch with him. I’ve never had the pleasure of being with a woman though while dressed or doing a role reversal. shaving now is just normal so is putting on panties and a bra. I have boobs now which when I first noticed them growing really excited me. I still love them but it’s just normal now.