BRTraveler
I love to hear stories about men and their crossdresser experiences.
One of my favorites happened about 20 years ago when I was still passable.
My girlfriend and I along with on of our male friends took a one-week vacation to Vegas and I dressed as a female for the entire time. I got dressed at home before we left and only took along female clothing. We hit the casinos, saw shows, went to dinner all while I was dressed. We would also go to the clubs and dance and have fun. On several occasions during this trip, I was hit on by guys who did not realize that I was actually a male and this really turned on my girlfriend. Some times, my girlfriend would reach under my skirt and fondle my cock just to watch me try to leave the place with an obvious hard-on and trying to hide it. In truth, I actually liked being "discovered" but could not afford the harrasement or possible violence that could come with it.

If you people are interested, I will tell some of my other "adventures" while dressed.

ridernmich
We would love to hear more.

katlove
We'd like to read more as well!

luvtitsndicks2
Oh yes I luv to watch two men dress up sexxy nd play ) soooo hot mks me wet just thinking about it !!

luvtitsndicks2
Oh yes I luv to watch two men dress up sexxy nd play ) soooo hot mks me wet just thinking about it !!

BRTraveler
The "date"

Our friend/lover, Sean, had a special request -- he wanted to take me out on a "date" as Heather (my fem name). Just the two of us. We talked it over with Wendy and she was all for it. Although Sean knew of my crossdressing, he had never seen me fully dressed or out in public.

On the night of the date, I was wearing a full skirt, lacy blouse, matching pink very lacy and sexy bra and panties, thigh-high stockings (I always hated pantyhose and never wore them) and 5" heels. Although, at the time, I had long hair as was not uncommon for men at the time, I decided to wear my blonde wig. Wendy helped me with my make up and picked out the perfect jewelry and accessories.

Sean arrived and we all sat for a few minutes, having a drink and chatting. Sean then took me to dinner at an absolutely wonderful Italian restaurant treating me like an absolute lady. After dinner, we took in a show. During the show, Sean would reach over and caress my knee and lightly stroke and tease my inner thigh -- driving me totally crazy.
Then, when the show was over, we went to a nightclub for drinks and dancing. On the dance floor, Sean would hold me tight, lightly caressing my butt and whispering in my ear. Then he put his lips to mine in a light lingering kiss, moving from my lips to lightly nibbling my earlobes and kissing my neck. God, I was sooo hard (I was able to hide this with the panties I was wearing and due to the pleated flair skirt). As we returned to the table, Sean would place his hand in the small of my back and escort me as a gentleman should escort a lady. Again, sitting at the table, he would gently stroke my hand, brush my face lightly with the back of his hand, lightly caress the back of my neck. I never felt so feminine and turned-on in my life. Finally, he reached his hand under the table and under my skirt -- I almost exploded right there. "We better leave now" he told me with a little grin.
We returned to his apartment and he began to undress. Following his lead I, too, began to move to undress but Sean wanted me to wait. Once he was naked - and, as I already knew, Sean was an absolutely beautiful man with a fantastic body - he gently took me by the hands and pulled me towards him, then reached under my skirt and removed my panties. He then pulled me down to his lap, putting his beautiful hard cock between my legs, then slowly kissing me and caressing my face, stoking my thighs, fondling and stroking my cock. I was in absolute heaven and allowed my feminine nature to take over completely. At that moment, I wanted nothing more than to please Sean. I slid out of his lap and down to the floor taking his beautiful cock in my mouth and slowly, lovingly sucking his cock. He then told me that he wanted to face-fuck me and this was fine with me as I actually loved to be face-fucked. He placed his hands gently at the back of my head massaging as fucked my face with deep thrusts until he finally exploded in my mouth and I slurped up every bit of glorious, creamy cum then licked his cock and balls clean.
The night only got better from there with the kissing, fondling, sucking going almost the entire night till finally, both of totally exhausted, we fell into the bed and I snuggled up closely to Sean and while he held me in his arms we both fell blissfully asleep.

aremgian
I love playing dress up and walking around the house feeling pretty, feeling sexy, feeling horny...

BRTraveler
Some of the most fun I had during my years of dressing was shopping. I used to love to go shopping with the girls. Funny thing is, as a guy I hate to shop. I guess it is part of my feminine nature when I dress.
Many times Wendy would go shopping for lingerie - which I absolutely loved - either just the two of or with a couple of her girlfriends. On a few occasions, we would also include one of our boyfriends.
Some of the hottest times were when a few of us girls would take our men with us to Victoria's Secret or Frederick's of Hollywood. Guys, if you dress, there is absolutely nothing more exciting to shop at these two stores while dressed!! Especially when you have a guy with you!!
To look at the bras/panties, the nightgowns, and other sexy outfits while a guy watches is awesome. It is even better when he or the girls begin choosing outfits and lingerie for you. While shopping, I would constantly visualize myself wearing my new and sexy lingerie that night and would keep an almost perpetual hard-on!!

crushed
if Max reads this he will probably be a bit pissed off but we are all friends here so here is what we did many years ago
I had the idea of cross dressing both of us for a Friday night and do a little club hopping in LA, We decided La was far enough away that none of our regular friends would know.
we went out shopping together to dress each other as we wanted the other to look. first off, Max took me to a costume store to buy a --ohh crap I cant remember the exact name of the girdle but it is designed to squish my boobs so I don't have any cleavage. it was very uncomfortable but it was what Max wanted so I went along with it. next we went to low end biker leather shop to buy a pair of leather pants, a rocken t-shirt, a due-rag to hide my hair and a black leather vest. nest we had to go to a kids store to get some black biker boots and socks.-- I thought I pulled it off pretty well
now for Max ( sorry hunny but you looked so damn cute I have to tell them) I took Max to a trendy women's store we got a red and black checkered school girl skirt with white panties, a bra we could stuff, and a white button down top. next we went to a shoe store to find a pair of size ten 2 inch black heals with fishnet stockings. next we headed back to the costume store to find a wig with long red hair.
well that Friday we hit the Bonaventure hotel in down town Los Angeles to a club that was all the rage back then. I thought max looked cute but most the guys and girls I talked to said he was "one ugly bitch"
I tried hitting on a few women but was turned flat down. max and I danced through the night when mex got asked to dance by this one guys. he was a bit of a geek but had a heart of gold. max and I had agreed if we were asked to dance that we could not refuse so max hit the dance floor with this guy. they danced for a while. during all this I kept asking women to dance and finely got one woman to accept. we dance the first dance then a slow song came along and I asked if we could continue to dance. she accepted but as soon as we held each other close she knew I was a women. she took my hand and pulled to to a corner of the dance floor and asked me if I was actually a woman. well I came clean and told her what max and I were doing to add a little fun in our lives. she loved it and pulled me to the dance floor this time. she kissed me right their on the dance floor and sent my head into a tail spin. man could she kiss. anyway. this guy that was dancing with max keep asking him to stay on the dance floor. max got to a point that he didn't want to falsely represent him self and let the guy think he had a chance at some fun so Max took him aside then signaled me to come over. I dragged my date over with me then we told him of our little secret. at first he was pissed but he soon got over it and came back over to our table. . max still felt bad about leading him on so I decided to make his night a bit more fun. I grabbed him by the hand, dragged him into the men's room, sat him down on the sink and gave him a blow job, my only regret was that no other men came into the mens room while I was sucking him off
my new date did kiss me several times but told me that was the extent of her being with a woman. well i was a bit disappointed but she stay around and the four of us danced and chatted. What i did get to do was take max into the women's room and commenced to giving him a blow job under that cute little dress. we did have two women walk in, looked at us, then said "what ever floats your boat" so i got max off. after the restroom romp with max we invited our two new friends to a early breakfast at a Denny's. it ended up that the two of our dates left together. what a night. oh and max, you would still look cute in your catholic school girl outfit
Teri

BRTraveler
I know it has been awhile since I last posted, so here goes.

While I was still married to Wendy and still young (around 27 or 28), Wendy and I had one boyfriend that absolutely loved to watch me get "dressed". Actually, Mark was really Wendy's boyfriend -- Mark was totally straight! But, he was also one of those very rare individuals in that he was completely non-judgmental as to the sexual proclivities and/or other tendencies in people. When I was dressed with Mark, he would treat me totally as a Lady - he would open doors for me, allow me link my arm into his, hold his hand, etc. He would sleep over (or have either me or Wendy or both at his place for the night) and, at such times, he would allow me to cuddle with him, he would wrap me in arms, allow me to rest my head on his chest and so on. He also loved for me suck his cock and worship his body.....but would absolutely would not reciprocate, he would not touch my cock, and he would not kiss me.
With all of that said, as stated he loved to watch me get dressed - especially if Wendy was also with us and watching me (she, too, loved to watch me dress and often took delight in helping me with my makeup).

One of my most memorable and enjoying times occurred after a night's activities with Mark, myself, and Wendy.
I had slept in an absolutely adorable sheer, lacy white baby-doll with matching panties. I woke up and decided to wake Mark with a blowjob. Of course, this also woke Wendy.
After finishing, I went to take my shower. Returning to the bedroom, totally naked, I saw both Wendy and Mark sitting up in the bed watching me. I slipped on my garter and stockings then put on my bra, but did not put on the breast forms or my panties. I stood and turned slowly around showing off for Mark and Wendy.
I then sat at the dressing table and began to do my hair - at that time, I wore my hair long all of the time, just a little longer than shoulder-length. After doing my hair, I applied my make-up then began picking out my jewelry - watch, a couple of bracelets, dangling earrings, and necklace. I then put on a pair of 3" heels.
I again stand - remember, I am still only in my bra and stockings, no panties - and, again, began to turn and prance around the bedroom, loving the attention I was getting from Mark and Wendy.
"You look gorgeous" Mark tells me. I am delighted to see that Mark has full hard-on and it is so exciting to know that I am responsible for this. Wendy has been fondling Mark (as well as Mark teasing Wendy's pussy) through all of this and, at this point, she begins to give Mark a blowjob. I am still prancing around the bedroom - actually being a bit on the "swishy" side by now - watching Wendy suck Mark's cock and seeing the admiration in Mark eyes. I develop a raging hard-on as I knew I would when I started to get dressed in this situation - one of the reasons that I had not yet put my panties on.
Wendy paused in her enjoyment long enough to tell me "Why don't you do something about that" with a grin on her face. As I said, Mark is totally straight and with Wendy otherwise occupied, I laid back on the floor and began to masterbate much to both Wendy and Mark's enjoyment.
Afterward, Mark chose my dress - a cute little yellow sun dress with red pastel flowers. I put my dress on and we all went downstairs for coffee and small talk. Soon, I put my panties on and we went for breakfast before taking Mark to the airport.

cdmindy
My first time with a man crossdresser:
I put on my matching set of blue bustier, garter belt, and panties, with blk stockings, blk 4" heeled pumps, blonde wig, full makeup, and my fit and flare red dress it's hem falls to 3" above my knees. It was midnight I decide to go for a drive, I head out hitting I 37 north towards San Antonio. I loved how it felt being out almost being seen. I went 70 mi north then turn around going south, I had to pee really bad, I see a picnic area sign and exit into it. It was mostly dark didn't have restrooms. I topped the hill in it and parked in front of a pavillion. I sit watching traffic flow which was none thru the picnic area, there was several cars and semis parked there but no people out. I get out, my heels clicking on pavement, I walk to pavillion to back corner, reach up under my dress pulling my panties down some I squat peeing like a woman. When done I notice the cool breeze loving how it felt blowing my dress up some. I go back to my car getting in. I think for a min deciding to smoke a cigerete outside under the pavillion. I grab cigs and lighter, check for traffic, then get out walking back to pavillion and sitting on top of picnic table my feet on part usually sat on. I light my cig and sit smoking it. About a minute later a semi pops over the hill, I was in his head lights range, was easily seen. I almost jump up to hide but realize it was to late. The semi drives on by and parks 100 yards farther down. I relax again smoking cig. I get up walking around pavillion enjoying it when I see a man only 30 feet from me, once again I didn't run hoping he not bothering me. He gets closer maybe 15 feet from me. "hi there miss sorry to bug you but could I get a cig from you please?" he asks. I freak out, "yea sure" I say in my best girly voice. I walk to table where I left them leaning over grabbing them, I turn and he is a few feet from me. I open pack holding over to him he gets a cig. "you have a light miss?" he asks. "yes" I say. "light me up please" he says. I step to him light my lighter, realizing he could now see me a lot better, he lights his cig. I was standing at end of table and back to it leaning back on its edge. "so what's a sexy little thing like you doing out here?" he asks. "just having a smoke enjoying the breeze" I say. "you been out to a party?" he asks. "no sir" I say. "just figured you had been being dressed up like you are" he says, bout then a car drives thru lighting us up as it goes by. He had to know by then I was a man. " I just enjoy dressing up sexy" I say. I had never been with a man but had fantasized of it. "oh yeah, hmmm, so what are you wearing under ur dress?" he asks. "stockings or panty hose?" Im not sure I should answer but do. "stockings" I say. "mmm my favorite, so prove it" he says. It was fairly dark out I doubted he could see but I raise front of my dress over stocking tops showing him. "can't really see em that good, ok if I feel them?" he asks. I freak out, but hear me say "yes" he steps up closer now only a foot away, I see his hands reach over one to each of my legs and on me sliding around finding my stocking tabs, I couldn't stop my "ohhh" quiet whimper when his hands touch me. Even with my heels on he was 6" taller than me and 50 lbs bigger. "sure enuf stockings, they are a big turn on for me" he says. I stand not knowing what to do or say, then feel his hands slowly rise up my dress playing with the garter straps as his hands go higher, I want to say stop but couldnt, my cock was tucked between my legs. "I'm totally into sissy boys" he says into my left ear, he had leaned over to me. He pushes my hair back so my neck is bare and kisses my neck. "ohhh" I moan. His hands now slide around to my panties ass and pulls me to him standing up. I still don't know what to do. His neck kisses stop as one hand leaves my ass to under my chin pushing my head up I see him lean to me pushing his lips to mine, he pecks my lips 3 times the 4th was full on lips holding there as I feel his tongue pushing thru my lips into my mouth. Both his hands back on my ass. I find myself kissing him back as my arms then go up circling his neck. He pulls me closer and harder up against him, I could feel his hard cock between us in his jeans. I decide it was time for my first. I reach between us with one hand and rub his cock thru his jeans. He moans as we kiss.shortly he stops our kiss, "you like what you are rubbing miss?" he asks. "mmmhm" I whimper. "do you want to be my little cock slut?" he asks me. "yes" I whimper again. "go on then get it out" he says. With both hands I undo his pants then reach in pulling out his big cock, it was a lot thicker than mine and longer, I find stroking it. He tugs his jeans and boxers down to knees. "tell me what you want to do with it" he says. "I want to suck it please" I hear me say. He turns us around and boosts up sitting on table, I reach over grabbing his big cock stroking it, looking at it. It was big, I slowly lean over to it, I couldn't believe I was doin this, his fat cock head at my lips then I open my mouth sucking my first cock. I suck it half way down slowly in and out of my mouth. "oh yeah suck my big cock sissy" he says. I go faster now. "oh yea faggot suck it" he says. His talking turned me on, he notices as I go deeper and faster. "mmm yea ur a good little cocksucking sissy faggot bitch" he moans. I now suck, slurp and gag on it. "oh yes, suck my cock faggot, you will love it when I fuck ur sissy ass" he says. He stops me then and stands up, pulls me close kissing again his hands up my dress again. He turns us again then turns me around so I face table his hands all over me as he humps my pantied ass. His hands pinch my nipples thru my clothes making me whimper. "you like that, yes tell me what you want sissy boy" he says. "omg mmmm yes I want to feel ur big cock deep inside of me" I say. He pushes me over my hands holding me up on table, as he pushes my dress up over my hips my entire ass showing now as he pulls my panties aside. I spread my legs and shortly I feel his cock push thru my cheeks and at my hole. I brace for it as he slowly slides all of it into me. "mmmmph" I moan wiggling my ass around. "oh yea work ur sissy ass around" he says pulling almost out them slamming back in me. He keeps doing that going faster as he does, I push back to him. You could hear our bodies slapping together then. "oh my god yes fuck me" I whimper. He goes faster yet. "oh god fuck yes fuck me hard I want to feel you shot ur load deep inside of me" I blurt out. He then slams in me holding us together I feel his cock jerking in me as his hot cum blasts deep in me. When he was finally done he pulls out, pulls up his jeans and gone. I stand up fixing my panties as his cum leaks out of me, I smoke a cig then get in my car going home.

Jrtranny
My first time was with a friend who was very happy to see me dressed up in lingerie and heels.. I love it and I’m sure you’ll be able to do it with your friends and then come over to the party and play with your friend.

I still remember that glorious feeling when I got it opened up and I saw it all on my body like I wanted to look. I went to a different adult store with video booth for me to undress so I just had my lingerie and heels on. I asked the guy if he cared and then he said go ahead. I just got so into the lingerie and heels and being sub. I even had my hands tied up and I was led around with the other guy in my the back of the store. It was a great night

NylonSammi
I dont have any good stories, just love to wear.

SWFL4biFUN
I used to have a local CD playmate who was like me, interested in wearing panties, thigh highs and heels just to make our cocks hard and imagine we were slutty women seeking to please another cock.

He got more into it than I did and started wanting to go into our local adult theater fully dressed. I went there to meet him with panties under my shorts butt prepared to lose the shorts and saw him sucking a strangers cock and then getting fucked bi another man.

Did not bother me to WATCH (and JO as I did) butt I never "played" in person with him again.

rob_nj
I was divorced/single in my 30/40's and went through a long period of time dressing. I was super slim and am tall and let my hair grow very long. At one point, I was "friends" with a couple and would go out with them to bars and even swing clubs. The wife of the couple would help me with shopping. Great time.

Bobby69cocks
I only crossdress at home,go out in my back yard in my g string, and drive around town half naked and in g string and crop tops I love to hear more stories and I love sucking cocks all the time, anytime

Cwtogo
I just address it home however I have hosted

touchmeuseme
I put on my wife’s black sexy panties.
It was not a good look.
Removed them and smelled the crotch.

Pntyman2021
Oh the stories I could tell would make so many of you cum in no time.

Lexyslove
Mm love going to the adult peep shows and porn video stores dressed in a sexy red dress looking at the movies having men come up start hitting on me which always made my cock hard and wet being felt up with my legs spread was a big turn on walked into the videoe booth left the door open pretty soon men were in my booth pulling my panties down licking my cock till I came all over there face they turned me around bent me over and gave me a good fucking mmmm when he left I went to stand up pull my panties up another man was watching me I got on my knees sucked and swallowed his cum mm love wearing my sexy red dress in public