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  #1  
Old 06-08-2009
daywalker267 daywalker267 is offline
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Default crossdressing experiences

recently i got my girlfriend to agree to let me wear some of her lingerie soon, heels too etc. shes also said to shave my legs and the rest of my body for the event. im looking forward to it tremendously, cant wait to have sloppy sex while we#re both dressed in lingerie. this is the first time ill ever have crossdressed in front of someone else, and i cant wait to get a blowjob while wearing stockings and high heels. even typing this now is giving me a hard on. might even go all out and get a wig too.

ive cross dressed in the past, but always on my own, jacking off privately. its always been such an adrenaline rush for me, the fear of being caught and getting away with it. ive also shaved my legs before, and put on my exs fishnets, highheels and underwear and admired myself in the mirror for a while. i looked damn good even if i say so myself, my ass in particular was hot. i jerked off and have a massive cum load on my smooth body afterwards, and even ate my own load i was so horny. now i can get to do it with someone else...

anyone had experiences like this in the past, either alone or with someone? or do you secrtly long to? my favourite part of crossdressing is the silky feel of tights on my smooth legs, and the feeling of a thongs tight grip on my asshole...feels so firm and right.
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Old 06-08-2009
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Crossdressers do it for SEX
and YES, it's a turn on. They can really get into it.:D
No appologies necessary.
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Old 06-09-2009
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I've done that loads of times. Gotten all dressed up in my fishnets, heels, bra & panties, and just wanked myself silly. It's best if you shave all over beforehand; shaved legs in fishnets look so good, and bare shaved legs rubbing together is a wonderful sensation!
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Old 06-09-2009
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Quote:
Originally Posted by daywalker267 View Post
recently i got my girlfriend to agree to let me wear some of her lingerie soon, heels too etc. shes also said to shave my legs and the rest of my body for the event. im looking forward to it tremendously, cant wait to have sloppy sex while we#re both dressed in lingerie. this is the first time ill ever have crossdressed in front of someone else, and i cant wait to get a blowjob while wearing stockings and high heels. even typing this now is giving me a hard on. might even go all out and get a wig too.

ive cross dressed in the past, but always on my own, jacking off privately. its always been such an adrenaline rush for me, the fear of being caught and getting away with it. ive also shaved my legs before, and put on my exs fishnets, highheels and underwear and admired myself in the mirror for a while. i looked damn good even if i say so myself, my ass in particular was hot. i jerked off and have a massive cum load on my smooth body afterwards, and even ate my own load i was so horny. now i can get to do it with someone else...

anyone had experiences like this in the past, either alone or with someone? or do you secrtly long to? my favourite part of crossdressing is the silky feel of tights on my smooth legs, and the feeling of a thongs tight grip on my asshole...feels so firm and right.
You experience what is normally referred to as a "transvestite fetish", meaning that you are a (probably) straight guy who gets off by putting female clothes on.

This has absolutely nothing to do with transsexualism - I guess you still identify as a man?

And I'm very happy for you that your apparently openminded girlfriend accepts it as it is.

So keep cross dressing, mano!

But ofcourse... it may be a start of something deeper... :-)

Best wishes!

Hank
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Old 06-09-2009
daywalker267 daywalker267 is offline
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Default

thanks for the encouragement all...and yes, do still identify as male, however seeing how feminine i can be is an incredible turn on...perhaps ill put some pics on if the oppertunity comes up ;p
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Old 06-11-2009
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it is a great feeling daywalker... and you are very lucky to have a supportive and encouraging partner. Good for you!

I am sure I am not the only one here that would love to hear more of your dress-up experiences
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Old 10-05-2009
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sounds like a hot night
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  #8  
Old 10-05-2009
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Default I hope it turns out to be everthing you want it to be a true fantasy come true

Give yourself plenty of prep time. Put as much thought into looking as pleasing to your partner as you can. Prepare yourself by first getting into the whole feminine experience by maybe taking a bubble bath or do your nails. If you kiss and make out as a warm up you could try putting on some lipstick, I was introduced to this by a bisexual girl she drew from experience. She had just applied her lipstick and snuggled up close to me and dropped her lipstick into her bag. She rummaged through her bag for a second and came out with another stick of lipstick. She took the top off of it as she screwed the lipstick out of the tube. she pointed it at my lips, I backed my head away, and she said its just chapstick I said ok and she started painting my lip's I knew it was really lipstick but I could always say that she lied to me. It was so stimulating having her painting my lps with such care. It put me in the middle of one of my fantasies wear, I am being forced feminized, anyway when she was done she could not wait to kiss me, and soon we were lip locked after just a few minutes of that she broke away from the kiss and said doesn't that feel sexy? I had to say it sure did. Now I know why she likes kissing girls. I will bet that your girl friend at least practice kissing first with one of her girlfriends before she ever kissed a guy. This could bring back very pleasant memories for her of a safe, carefree, time in her life and put you both in a sexier safe mood. But please you know where your boundaries are in this relationship so thread carefully, if you think that this is too fast, then let me suggest getting a tube of lip balm and put on a good coat before you meet for your event you can bring up that your lips have been dry lately, and you have lip balm on if she gives a sign of offence just say let me get some of this off, I really been lathering it on lately.
I think you said that you have shaved your legs before, but rather you have or not the pubic area is a whole other experience you could be very sensitive like me down there and if you are you could be in a whole lot of hurt just shortly after you remove the hair by what ever method you use and this could ruin your whole night so get on the internet. there is a lot of good information and a lot of bad information just use your good judgment and have a ball. Oh yes we must have a report of everything that happened panties and nylons garters and heals simply scrumptious. Now do as your told and mind your partner and try your best to follow her instructions to the letter if you find that you are having difficulty with anything call her and ask for her guidance and permission. I hope the pictures help you get in the mood
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  #9  
Old 10-07-2009
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Default That's me

My avatar is me crossdressed. I am still very male but its another experience that makes me feel sexy and a bit vulnerable. I am usually very top but dressing like a woman allows a part of me to come out that usually does not.
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  #10  
Old 10-07-2009
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to me there is nothing sexier than wearing a pair of panties under my dress clothes all day. just squirming in my leather chair at the office while the slick silky feeling of the panties rides me all day making me hornier and hornier until i have to go release in the bathroom at work. there is somthing about seeing my thick creamy cum in a pair of panties that is very arousing. i like the feel of it too, all messy in my cute little pink panties. i must admit i really enjoy the feel of a g-string up my ass as well - quite a sexy feel. almost slutty. i would like to be a slut for another cross dresser. i would like to be bottom in my panties

dre jones - you look quite hot in those panties - love the bulge!
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Old 10-10-2009
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i used to wear my mom's bra whenever i was home alone. haven't done it in 2 yrs or so.
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  #12  
Old 10-10-2009
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Sigh.... I can't wait until I live alone and can cross-dress more often. In fact, I haven't had the opportunity in months. I just want to dress up as a Catholic Schoolgirl and have sex with James Marsters, is that too much to ask?
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  #13  
Old 10-13-2009
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It was shemale porn that gave me the idea of crossdressing. Most crossdressers start as young kids, and have the urge to do it all their lives. I'm one of those sexual fetish transvestites - I do it only for the sexual rush. I actually started wtih lipstick. The first time I opened a tube of red lipstick and put it on my lips, I almost came while I was still doing it - it's so hot! Then I moved on to buying bras, panties and nylons. That turned me on - I always ended up in a fantastic jerk-off session - but I had to go all the way. I ordered a wig online and started shopping at thrift stores, and got myself a little wardrobe of short skirts and tight dresses. I also filled up on makeup of all kinds and started practicing with it. The first time I did myself up fully - panties, bra, lacy thigh-highs, a clingy dress and a wig - it was one of most intense experiences of my life. Just pulling that dress on made my head spin, and finally putting the wig on at the end and staring at myself in the mirror was such a turn-on. It's all about the transformation for me - turing myself into my version of a sexy woman. I just loved everything about it.

If this is the kind of thing that appeals to you, but you've never had the nerve to try it, you've got to do it. You won't get the makeup right the first time, and you may feel silly at first, but it's totally addicting. It's like a drug, and a great drug! I haven't done it for a while, but now Ive got myself all aroused writing about it, and I can feel a session coming on very soon!
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  #14  
Old 04-18-2011
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Not too sure this is the right place to post, but I've done another first.. I bought a female wig and a cat face mask.. I tried them on earlier, with my bra and a thong and it felt/looked so good that I couldn't help but masturbate
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Old 04-20-2011
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I do it sometimes when I go on cam sites. I took this one a few weeks ago
^^^
Boys really seem to like it :')
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Old 04-21-2011
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I have been crossdressing since my pre-teens. The more feminine and passable I feel, the more masochistic and turned on I am!
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Old 04-21-2011
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Boys really seem to like it :')
Yes they do, and I like their big tools
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Old 04-22-2011
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Quote:
Originally Posted by BigPhilly View Post
I do it sometimes when I go on cam sites. I took this one a few weeks ago
^^^
Boys really seem to like it :')
well i certainly do, you look hot hun
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  #19  
Old 05-24-2011
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I bought a new top today, it looks gorgeous. It's black and white stripes, with ruffled shoulders. I tried it out with my really short denim shorts. It looked great! I'm thinking of going out sometime, maybe on a Friday night, in a few weeks time. We'll see!
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Old 11-22-2012
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Thumbs up crossdressing

I'm not a crossdresser but wearing thongs and wearing garter-belts, and nylons during sex is a plus for me,
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  #21  
Old 11-22-2012
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im crossdresser too and love to do on skype
add me kadito69
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  #22  
Old 12-07-2012
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Many many years ago (probably just after a relationship breakup) I was at a bazaar and saw a black dress. I was surprised by the feelings that suddenly came to me, and impulsively bought the dress. It was a great turn-on getting dressed-up once or twice, but then I guess I got into another relationship and the feelings disappeared again.

Fast forward to today, and I have a secret dressingup box for when I'm alone. It's only skirt, stockings and a wig so far. I take photos when I dressup, but I don't think I'm at all beautiful, so haven't had the courage to post any of them here. BUT I am soooo happy to have found this forum where I can meet others with like interests.

Thank you to the webmasters, moderators and all of you who have posted so many interesting experiences and wonderful photos!
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  #23  
Old 12-14-2012
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the best part about cross-dressing to me has always been about nylons and heels

even though i fully cross-dress when i do...wigs makeup etc...the heels make me FEEL it
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Old 12-17-2012
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i wore high heels many times and jerked off. high heels are extreme turn on for me so i can not resist thinking of them, looking at the feets (high heels) of women outside, jerkin off lookin at the pics or vids of ladies in high heels... so when i wear hig heels, i feel as i gonna have an heart attack by the excitement they make me feel.

i really do want to be dressed in higly sexy women wear, too. it is one of my biggest fantasies to have a she cockk in my mouth while i'm dressed like that.
never had sex with a ladyboy or a shecock in my mouth, but i can not resist to have someday... and be crossdressed
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Old 12-18-2012
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Quote:
Originally Posted by mmmfajitas View Post
the best part about cross-dressing to me has always been about nylons and heels

even though i fully cross-dress when i do...wigs makeup etc...the heels make me FEEL it
For me it's a short skirt! But I know how you feel!
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