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  #1  
Old 18th May 2006, 12:17 AM
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Join Date: Feb 2003
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Crossdressing the first time

Any crossdressers out there, I would love to hear your story about the first time you dressed for a man and let him have his way with you. I will add my own experience as soon as I have time to write it. In the mean time let me hear about yours.
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I am fairly new to the Goldsboro area and looking to hook up with some mature friends for fun. If interested drop me a line and lets see what happens.
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  #2  
Old 25th May 2006, 09:58 PM
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Join Date: Nov 2003
Posts: 17
fist time

my first time
i meet this guy i talked to online, he invited me over to his place
told me to bring my clothers with me, i already was wear my red
red nyllons,bras panties, garter belt under my reg clothes
after i got to his place went into his bath room, put on my blond wig, lipstick (red) red mini skirt. when i came back into his bedroom he was already naked waiting for me. he grab me and kiss me wet feeling me up all over. then pushed me down on my knees and told me to suck his big thick cock . i lick sucked it for a long time deep throting him had he pressed my head into him
finily he lead me to the bed sucked and bit my tits moving down
to my panties sucking my cock though them then he pulled my panties off and turn me over and lubed my ass real good and next thing i know he had drove a big dildeo up my ass and fucked me with it until i was nice and loose. then he had me get on all
fours that withone push ramed me with his big thick cock and fucked me for a long time till he came in me and then told me to suck him more. as i was sucking all of a sudden i felt something big and long sliding into my wet male pussy and it was a friend of his fucking while i worked his cock and balls after we all cum
i left it was great to have two guys using as their slut
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  #3  
Old 26th May 2006, 06:54 PM
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Join Date: Mar 2002
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Here’s my tale
I love to cross dress. I love the slinky feel of lingerie, the sexy shimmer of pantyhose sliding up my legs and the sleek look of high heels on my feet.

To know me, one would never think this. I am masculine, a bodybuilder and quite muscular. Until I was married, I usually had no problems attracting woman.

I fantasized when I dressed in lingerie, (complete with wig, thong teddy, camisole, stocking or thigh highs, heels lipstick and blush) of being treated as a woman and be taken advantage of with a long kiss and a fondling followed by a long sensual fuck by a strong attractive man.

I used to dress under my work clothes at the office and couldn’t wait to get home to take a bubble bath, shave my legs and dress for the night.

Although I had met guys before, I decided to take the plunge dressed. I met a man online and he agreed to come over then next evening.

I couldn’t wait for the next day. I dressed and played with my ass pussy and my cock and fantasized about dressing and sucking cock. When the doorbell rang that night I was jittery. I had taken a long silky bubble bath and shaved completely except for a small patch above my cock.

I put on my black gartered thigh highs and a black thong teddy and pulled my already dripping cock back a little to make myself look more like having a pussy. I wore bright red lipstick and put on a fresh coat of nail polish (nothing like lovingly sucking a cock and admiring your nails while you caress those sweet hanging balls) to add to my glow. I wore a beautiful full curly brunette wig that came down to my shoulders and put on a touch of blush. To finish it off I put on a beautiful pair of black pumps. I peered through the peephole and saw an attractive man standing there and opened the door enough to let him in, but careful not to let the neighbor see me.
He brought a bottle of wine, which I opened and served as he relaxed on the sofa. I put a sex porn tape in and as we watched 2 studs get it on, I felt his hand caress my silky leg. I turned towards him and gave his neck a ling kiss while his hand traveled up and down my legs and slowly caressing up to my ass. Oh God, I thought I would explode right there.

I moved up his neck and kissed his chin. To my surprise he kissed me long and hard, his tongue caressing mine and exploring every bit of my mouth while his hands played with my ass.
I could finally hold it no longer. I got on my knees in front of him and felt his cock through his cotton pants. It was extremely huge and I was surprised, thinking that perhaps he had a dildo in his pocket to play with me.
I opened his zipper and worked his pants (no underwear… mmmmm…) down to his knees and there was the largest cock I had ever seen in life. Now I know people say this, but it was almost as thick as a coke can and about 7.5 – 8 inches. Huge, magnificent, but terrifyingly huge. I caressed that beautiful cock and squeezed a glistening drop of precum out of the large tip. I looked up at him, he smiled at me, held my chin in his hands and guided me to that massive cock.
I licked the precum off and played with it with my tongue take ever more in with each swirl, I couldn’t take the whole thing in without gagging, but I tried. I was absolutely turned on at the thought of being treated like a woman while sucking a massive cock. He then pushed me around and took my cock in his mouth and we sucked each other. I then felt his tongue slid past my balls and start lingering around my pampered ass. It felt so wonderful and I knew I had to have that cock in me.
He pulled my thong to the side and started to lick my ass hard I moaned and pushed my hips towards him, begging to be taken. I then felt a finger in me and then two. I pushed back hard as his saliva covered fingers slid in and out of me.

After a few minutes of this, he said, "You really need to be fucked in that sweet ass of yours." I said back teasingly, “Are you man enough to make me your little fuck doll?” With that he spanked my ass – one slap. I almost came. I rolled on my stomach and then up on my hands and knees and said begged him to pleas fuck me. He wasn’t done with my mouth yet, he came around the front of me and this time I swallowed him completely, knowing that he could have me anytime he wanted.
When he was good and wet, he spun me around and pulled my teddy thong to the side again and I could feel his cock pressing against my asspussy. I pushed back and could feel the tip of his cock trying to get through. I grabbed a tube of Vaseline from the floor n front of me and asked him to put it on. He did. He then came back and pushed hard. I thought I was ready this time…..Ooooohhh..
The pain was immense. Much more than my dildo. Ohhh, it hurt so bad and then suddenly, he was in. I could feel him almost to my belly button – I had never felt anything like that before. It was incredible. All I could do was lower myself to the ground and arch keep my ass up while he worked his way back and forth.
He had me and I loved it. I tried squeezing as hard as I could and he could feel it. It was long before he started slamming me hard. I could feel his hairy balls brush against my smoothly shaved balls, tickling me each time.
Suddenly he grabbed my hips, held me tight and thrust hard. I hadn’t wanted him to come inside me, but there was not way I could stop it now.
I could feel him pulse inside me at least 4 times and then slowly subside. What an intense incredible feeling. Oh, now I know why women loved to be fucked.
He slowly pulled out and along with it was a thick wad of cum, which dripped out of my ass and onto the floor. I stood up achingly, and went into the bathroom to clean up. I came back out and he pushed me on the sofa and gave me the softest blowjob I ever had. Within 30 seconds I spewed cum all over his face and my lingerie. He licked it up and then kissed me again, long and softly, depositing all my cum back on my tongue. WoWWW!!! SO SENSUAL!!!

We met twice after that and then he moved away. How I long to be his beautiful fuck doll once again.
Each night after he left, I would cum at least 3 more times and always in my lingerie and always unable to sleep after my ass takes such a hard pounding!!!
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  #4  
Old 1st June 2006, 09:33 AM
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Join Date: Feb 2003
Posts: 19
As Promised

Well, as promised here is my story:

My First Time Crossdressing for a Man

We first met on the internet like so many. As time passed and we shared more and more of our interests and desires, I let him know of my secret fetish to dress in my wife’s clothing. In fact, that I had gone so far as to have hidden away a wig and very realistic breast enhancers. He encouraged me to be more graphic in describing myself when dressed in my wife’s clothes. He told me the more I did the hotter and hornier he became, which didn’t slow down my horniness. In fact, I would crossdress before sitting down to chat with him, which would make me so hard my cock would ache.

During one of our steamier sessions he ask me if I would come to his apartment and crossdress for him. As I was not only a closet CD, but a closet bi person…I guess so closeted that I was a total virgin. Anyway, I agreed not knowing why or even if I would get up the nerve when the time came. We planned the meeting during a time that my wife was going to be away.

My wife isn’t a particularly large woman, but with her slightly stout build and my slim build I am able to get into most of her things. She almost caught me one day when I was laying out what I wanted to wear.

While planning our meeting we decided to do some roleplaying. As he was already a shoe clerk, I would play his last customer of the day. Well, the big day came and I was nervous all day fantasizing about how he would touch me, where he would touch me, how his touch would feel. Finally, the time came and I loaded my women’s clothing into a bag and drove to his apartment. It seemed that I sat out here for an hour getting up my courage, however it was only a few minutes.

I rang his bell, we shook hands and he showed me to the bedroom. We had agreed that we wouldn’t talk that we would just shake hands and then I would dress in private. Making our next encounter with me as a woman. We had decided that I would play being a real woman…not a man crossdressing, if you know what I mean. I can’t tell you how excited and scared I was as I arranged my clothing on his bed and began to undress from my male clothing.
I put on matching black lacy bra, filled with my realistic padding, and bikini panties, dark thigh high nylons, black skirt with a white flowery print and a silky black blouse. I added lipstick and makeup then my expensive and realistic dirty blonde wig. As I looked in the mirror I thought I had never looked so good. I slipped in to my low heal shoes, took a deep breath and opened the bedroom door.

Bill was there with a line of shoes already in place and one of those stools that shoe clerks sit on when fitting you for shoes that he had brought from his store. I could tell from his smile and the way he looked me up and down that he was pleased, which relieved some of my anxiety. He told me that the store was about to close but that he would be happy to help me. He went to the front door and locked it and turned one of those OPEN/CLOSED signs around so it showed OPEN on our side. He came back had me take a seat on his sofa and asked what I was looking for. After a brief discussion he started showing me some shoes.

As he started trying them on and having me walk in them I fell more and more into the part I was playing. Feeling oh so feminine. Then as I sat and he tried on another pair of shoes his hand roamed slightly up the calf of my leg. It was so casual that I almost didn’t notice. With the next pair he casually raised my skirt to my knees so I could get a good look at the shoes. All the time his hands were touching my legs so nonchalantly.

Then with one pair he raised my leg to hold it straight out so I could get a unobstructed look at the shoe and at the same time he was getting an unobstructed look up my skirt. As he lowered my leg, he moved forward and his hand moved just above my knee onto my inner thigh. The touch was like magic and accomplished its intended purpose, as I sucked in my breath and half closed my eyes. I was rapidly starting to feel the passion of his touch.

He looked straight into my eyes as his hand slowly moved up my inner thigh. I finally knew what it felt like to have a man’s hand touching my nylon-clad thigh other than my own. It was unbearable, as much as I tried and wanted to keep myself soft and feminine I became hard as a rock. Then when his hand reached and passed the top of my thigh high and touched my flesh I thought his hand was on fire. I was no longer a man I was a woman filling with passion and desire.

As his hand reached and his finger tips caressed my panties, he moved to the sofa next to me. My skirt was pushed up, you could see my skin above my thigh highs and I could feel his soft, gentle hand starting to fondle me. I was now totally his for the taking. He leaned over and softly kissed my lips. The first time man had kissed me and I was somewhat surprised as I puckered to return the kiss. As his hand began to probe and massage what he called my large clit, his kisses became more intense and before I knew it his tongue was in my mouth and I mine was dancing with his. His hand left my pussy and slowly started unbuttoning my blouse. He pushed it back and fondled my breasts through my bra. I swear I could feel every touch and the tease of my nipples.

As he moved down to my neck, my chest (which is naturally smooth) he rested his cheek against my bosom. Then he went lower and lower tonguing my belly button and slipping past my pushed up skirt to oh so slightly kiss my aching clit through my panties. His lips found the massive wet spot I had created and he kissed and licked at it. I was moaning and swooning like any woman caught up in the ecstasy of the moment. He told me how wonderful I tasted and then I felt his hand start to remove my panties. All I could do was raise my hips to allow them to slip down my legs to the floor. He licked and kissed my clit while both his hands were massaging my breasts through my bra. When he sucked my clit into his mouth I thought I would explode then and there. However, I was able to hold off…how I will never know.

He pulled me down into a flat position on the sofa with me on my back. He kissed down the sensitive under side of my clit and over my thick heavy clit sack. He pushed one leg up and hooked it over the back of the sofa; he raised and spread my other leg with his hand. That is when I felt his hot lips kiss my pussy as his tongue stroked it. I uncontrollably raised my hips off the sofa to meet his wet mouth and let out such a moan that I am sure his neighbors on both sides could hear me. He probed and kissed and licked and I squirmed and moaned and almost lost consciousness the feeling was so intense.

Then he pulled away and stood looking down at me. He started unbuttoning his shirt exposing a well-defined chest covered with black curly hair. As my pussy was still burning from his tongue I watched as he unbuckled his belt, loosened the top button and slowly unzipped his pants. As he let them fall to the floor around his ankles my eyes followed his thick black curly hair down to where it surrounded his hard perturbing cock. He wore no underwear. His cock was average in thickness, but seemed very long and curled upwards. Which seemed so sexy to me as I lay there looking at it and the shiny tip.

He bent down and took a jar from beside the sofa and opened it. He stuck in two fingers, lowered himself to one knee between my legs, as one was now hanging off the sofa onto the floor, and started spreading a warm creamy substance all around my pulsating pussy. I thought I would die when I felt a finger enter me and spread this warmth inside my pussy.

It is funny now but at the time I never really put two and two together. I was just so filled with passion and lust that he could have done anything to me. He leaned forward and kissed me again. I will never forget that kiss, as it was so sweet and loving and tender and passionate all rolled into one. I returned the kiss with every nerve ending in my lips.

He again stood above me and taking the same jar again dipped his fingers and this time spread the warmth over his cock. I could only stare at what seemed like a magnificent tool. He returned the jar to the floor and again placed on knee between my legs on the sofa. He reached down and hooked my one leg that was down off the sofa and raised it up over his shoulder. He leaned forward and again kissed me. Not as softly not as sweetly but with more intensity and lust. This is when I felt it, felt the tip of his cock lightly pushing against the crack of my pussy.

I knew what it was, I knew where it was and for the first time I knew what he wanted. And I knew I was his woman and that I could never say no to him. He whispered in my ear, “Guide it for me.” As if in a trance and completely under the control of this man, I took one hand, found his throbbing rod and placed the tip at the opening of my puckering pussy.

My mind was bombarded with the knowledge that this man was about to fuck me. And even more by the awareness that I wanted him to, that I wanted to give him the ultimate pleasure a man can have, that of inserting his penis into a hot willing pussy. I felt him push and my hands went to his hips to help pull him into me. He stared down at me and I in return stared back up at him. Our eyes locking onto each other and telling the other that this is okay, that this is as close to pure love in one moment that any two individuals will ever encounter.

That is when I felt his nub penetrate my pussy with a shooting pain that for some reason I relished. He saw me wince and paused. But my eyes told him to continue and he slowly started pushing deeper and deeper into me. I never felt more like a woman in my life as I was letting my man have his way with me, giving him my treasure. When he was completely inside me his body fell on top of mine and he kissed me. Not a wild lusting kiss but one of gratitude and love. One that said thank you for allowing me this ultimate pleasure. And then his hips started to move up and down, up and down.

I was being fucked by this man, me who had never even sucked a cock or been sucked before. And I was loving it, I couldn’t get enough. I heard him say, “I want this to go on forever.”

I responded, “Yes, yes never stop never stop fucking me.” I couldn’t believe it, I was even admitting it, saying it out loud that I was being fucked. He would go deep into me and hold it there and I would work his cock with my pussy muscles then he would fuck me some more. It seemed that this went on forever and ever. I was in a state of euphoria.

Then he started quickening his pace, a look of urgency came over his face. He started uttering over and over, “Fuck, fuck, fuck, fuck.” As he pumped my pussy faster and faster. I uttered back at him to let him know it was okay, “Yes, yes, yes, yes.” Then he slammed into me deep, wrapped his arms around me and I could feel him deposit his seed inside my willing and accepting pussy. He was moaning, “I didn’t want to cum, yet.”

I assured him, “It’s okay baby, it’s okay.” As my pussy clamped around his pulsating cock and tried to milk every drop of his goo. I had become so excited at the thought of him cumming inside me and even more so when he did that I never realized until we started to relax that at the tip of my clit was a pool of my own juice being squished between us.

When he finally eased out of me, he took my hand, lead me to his bedroom, finished undressing me except for my thigh highs and bra and we curled up together in his bed. Oh yes, when we did wake up, he did fuck me again. I can’t say that it was as good as the first time, but it and every time after that has been a close second. We don’t always roleplay when we get together, but I always crossdress for him I will always be his woman.
__________________
I am fairly new to the Goldsboro area and looking to hook up with some mature friends for fun. If interested drop me a line and lets see what happens.
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  #5  
Old 30th July 2006, 09:56 AM
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Join Date: Feb 2005
Posts: 31
Wink My 1st Time

I also met an older man online, probably in his late 60's if I remember right, and we hooked up to go to his house. I had brought some items that I would normally wear; stockings, a short red skirt, a red nightie, and makeup. Lo and behold, he wasn't the only one there. he had invited a friend of his who was a little older. They were both naked and had been sitting on the couch watching porn. The older one escorted me to the bathroom where I could change. I threw on my outfit, applied eye shadow, lipstick, eyeliner, and some blush, and then walked out into the living room where they were both seated, each one jacking off.

They had me crawl on all fours in front of them while they furiously jerked off. The sound and images from the porno on TV was turning me on like crazy. The older one leaned forward and slipped his hand up the backside of my skirt and tried fingering me. The other guy took cue and got off the couch and dropped to his knees while he rubbed his cock off on my face. I took him in mouth while the other finger fucked me and was massaging my nuts. Pretty soon, the man whom I was sucking off had laid down so that I could service him while his buddy began rubbing his cock up and down my ass crack.

I felt like such a feminine whore that I began to moan loudly and tried to change the tone of my voice to sound more like a lady. This turned them on even more and soon the guy behind me started to poke his cock into my ass, thrusting harder every time. It made me horny as hell letting them have their way with me.

It wasn't too long until his cock popped off into my mouth, big sticky loads of cum shot down my throat as I gulped his juice down. The older guy behind me was pounding away like crazy and had me lay on my back. I turned to lay on my back as he grabbed my ankles and held them up as he fucked me missionary. The other old man began twisiting my nipples and telling the older man to fuck me harder, to shoot his cum all over my pussy. That's when he moaned outloud and instead shot his cream deep inside my butt. He bucked his hips for a moment then sat back down on the couch, breathing heavy.

They then had me lay on my back again and jerk off for them while their limp cocks tried to stiffen again. Just watching these two old men jerk off to me got me so hard that I blew my load all over my stomach in 3 minutes flat.

I never had the chance to dress up much after that incident but it sure does drive me to temptation. Maybe one day again soon...
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