I Finally Go Out While Dressed As A Woman

Swordmonkey

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I'd been cross dressing for a few months at this point, but I'd never gone outside while dressed up before. I'd been to the shops a couple of times wearing one of my outfits under my normal male clothes; that's the closest I've ever been but just doing that turned me on a lot. Even under a fairly loose coat, I'm sure people could make out the outline of my breast forms. Since those little trips to the shops had got me so aroused, I was determined to do it properly so I decided that the following Friday I would go clubbing in town.

Friday came and I'd bought a new outfit just for the occasion. I slipped into my black lace low rise boy shorts , tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my D cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd been blessed with an arse that any woman would kill for so I could pull off wearing a skirt this small. The skirt had suspenders which I connected to my stockings. I finished off my outfit by putting on a tight black low cut top and adjusting my breasts so that I got some pretty good cleavage.

Next I had to put my makeup on. The good thing about having been cross dressing at home in private for so long was that I got a lot of practice putting make up on, so it was no trouble for me to put on some foundation, eye shadow, mascara and lipstick to make me look that bit more feminine. I already keep myself relatively hair free so all I had to do in this department was pluck a few stray hairs that my razor couldn't get to. I sprayed on some of my best perfume then got my wig out to put on. It was a wavy copper orange coloured wig that reached down to just past my shoulder blades.

After this I was done, so I went downstairs and to my front door. I reached for the handle but stopped for a second. I took a deep breath and thought to myself that I was about to go outside dressed like a woman, something that I'd never done before. So I composed myself, opened the door and stepped out into the outside world. Luckily, it was a warm night so I didn't need to wear a coat and could show off my assets. I spotted the taxi that I'd phoned for earlier and walked over to it. As I got in I could see the taxi driver looking at me through his mirror. He was looking me up and down with a hint of lust in his eyes. So far so good I thought to myself. I told the driver where I wanted to go and we set off.

On the way there, I noticed the driver kept glancing at me hoping I wouldn't notice. I blushed a little and smiled to myself, apparently I make an attractive woman! We arrived at the nightclub about ten minutes later and I got out, paying the taxi driver, then walking over to the entrance. As I got there, the bouncer gazed at me , waving me through without a second look. I stepped through the door and into a large building full of drinkers and dancers and pulsing with club music.

I walked over and sat on a stool by the bar. I was only there for a few minutes before a guy strolled over to me. He looked like he was just a shade under six foot, had an average build and short brown hair, well-built but not overly so.

"Hey, can I get you a drink?" he asked me.

"Sure..." I replied, my heart racing with excitement. He ordered a drink for me and himself and as we sat there drinking, we began to talk. We talked about the usual things, where I'm from, what I do, what I like. After a few more drinks, the conversation eventually took on a more sexual nature.

I told him I wasn't that experienced in sex which he said surprised him as he thought I looked that good that I'd be beating guys off with a stick. I giggled, putting my hand on his leg, which he seemed to like as I could see him harden a little in his pants. The alcohol was helping lower my inhibitions and the more I had, the more I flirted with him. We moved onto the dance floor and danced for a bit, grinding our bodies together to the music. After a little while, he placed his hands on my waist and moved his head towards mine, leaning in for a kiss.

I pulled back for a moment, hesitating, I'd never kissed a guy before. I could feel his warm breath on my face as he waited for my reply. I made my choice, lifting my head a little so my lips would meet his. A warmth spread through my body as we kissed and I wondered why I'd never tried this before. His hands slowly moved to my arse and he pulled me closer to him as continued to kiss. I placed my hand on the back of his head and started to involve my tongue in the kiss with him responding in the same way.

After a while, he moved his head away from mine, breaking the kiss and leaving me desperate for more. He leaned his head in towards mine and whispered into my ear.

"You want to take this somewhere else?" he asked, gesturing his head towards the nearby toilets.

I had a feeling about what he was hinting at, so I nodded and he took hold of my hand and led me across the dance floor and towards the toilets as my heart pounded at the thought of what was about to happen.

He opened the door to the toilets and pulled me in to join him, leaning me against a row of sinks in front of a large mirror and began to kiss slowly up and down my neck. My eyes rolling into the back of my head from the pleasure. He moved up, kissing my cheek as he went along, before moving onto my lips which he gently caressed with his, slowly moving his tongue in and out of my mouth. I moved my hands to his chest and, not wanting to have stopped kissing in the first place, I hungrily returned the favour and allowed my tongue to enter his mouth. After a couple of minutes, I broke off the kiss this time and I saw a glint in his eye as I knelt down on the floor and looked up into his eyes with a slight grin on my face.

He moved a little closer and I reached up, unzipped his fly and carefully pulled out his penis. It was pretty big already even though it wasn't even fully erect yet, about five inches I'd say.

“Mmm...so big...” I moaned as I stroked him, still looking into his eyes.

I leaned forward and started licking and sucking down the side of his shaft as I heard a soft moan. I slowly moved back towards the tip which I licked around in circles a few times before I couldn't wait any longer and finally put my lips over the head of his penis and began to suck his shaft down towards the back of my throat. I started off going about halfway before moving back to the tip while stroking the rest of his penis. I continued to bob my head up and down for another minute or two before I got the courage to start deep throating, gradually moving my mouth all the way down to the base of his penis so the tip was touching the back of my throat and my mouth was touching his crotch.

He began to moan loudly as I fought my gag reflex for a second or two. It calmed down and I stayed in that position for a good ten seconds before I gently drew back along the length of his shaft and allowed it to leave my mouth with a slight popping sound. I looked up at him with a cheeky grin on my face.
"You like that?" I asked while stroking him off, using the spit I'd left down his shaft as lubrication. A low groan was all he could reply with but it answered my question well enough.

My attention was then drawn to his balls, which were smooth and completely hairless. I leaned in towards them and, while continuing to stroke his manhood, took one of his balls into my mouth and set about rolling it back and forth over my tongue. I kept sucking on his ball for another minute before I let it slip out of my mouth. I could see by the look on his face that he was disappointed I'd stopped but he wouldn't be for long as I stopped stroking his fully erect penis and instead pointed it towards my mouth and took the entire length in straight away this time.

I moved my mouth up and down his throbbing member, each time taking it in all the way to the back of my throat before withdrawing so far that only my lips and tip of my tongue were touching it. After a while, he gently put his hands on my head and began to slowly push downwards each time I was going down on him. I took this as a sign he was getting close and I increased the speed of my sucking to which he responded with louder moans. As I stepped up the speed further, his moans got even louder and more frequent. I could tell he was on the verge of an orgasm so I started sucking as fast as I could, deep throating each time. Very quickly his hold of my head got tighter, his legs started to tremble and his manhood quivered as he orgasmed in my mouth.

He came in large spurts, each one hitting the back of my throat, giving me no choice but to swallow. He slowed down after another few squirts and, thinking he'd finished, I pulled him out of my mouth and he unexpectedly squirted two more jets of warm cum onto my face. I was taken aback for a few seconds as I wasn't expecting it, but then I ran my finger over my face and licked off the stray cum before swallowing it with a smile. He was breathing heavily now, clearly exhausted from an intense orgasm.

"God, that's the best blowjob I've had in ages." he said, in between his deep breaths.

I was pretty shocked at his comment; before tonight, I had never even done anything with a guy before. Sure I'd fantasised about it and practiced with toys, but I'd never had the real thing and here he was saying that the first blowjob I'd ever given was one of the best he'd had in ages!

"There's more to come yet, if you're up to it." I replied playfully as I got to my feet and leaned over a nearby sink, turning my head to look at him. I hiked up my skirt and pulled down my underwear just a little, sticking my butt out seductively.

“Lucky for you, I can go again straight away.” He said, smirking as he joined me at the sink.

I'd tried using a dildo anally at home, it was about the same size as the real thing that I'd just been sucking on. Even with lube, I only ever managed to get it in just past halfway but I was so caught up in the moment of having my first time with a guy that I was about to try taking the whole thing without anything to make it slide in easier and I didn't care!

I braced myself on the sink as he gently took hold of my head and kissed me. I reached behind for his dick and when I got hold of it, it was still rock hard. I guided it towards my hole and felt it prod at the opening.

“Shit, girls don't usually let me stick it in there!” he quipped.

I giggled as I probed my hole with the head of his dick. I couldn't wait much longer as I was getting hard just at the thought, so I backed into him to show that I wanted him to give it to me now. He duly obliged and slowly started pushing into my hole and my legs began to tremble. He kept pushing further, eventually getting in further than I had managed with a dildo which is when it started to hurt. I think he could see it was starting to hurt me because he forced in the last couple of inches to get it over with. There was a sharp pain for a few seconds but this was quickly replaced by an amazing feeling as his cock was inside me.

He started thrusting, slowly at first, allowing me to get used to the feeling. He quickly sped up as he got hold of my hips and increased the force of his thrusts. His balls were slapping against my arse with each thrust and I couldn't believe how much harder this made me. We were both moaning with pleasure, I'd never experienced this much bliss before now. I started backing into him each time he thrust to increase the force and this nearly put me over the edge. I was so close to cumming that I had to slow down and let him do the work.

He moved his hands to my breasts while still pounding me. It was a good thing I'd spared no expense with my breasts forms as he went to town on them, grabbing them with some force. I moaned with pleasure at his treatment of my breasts which seemed to please him. He started to use my breasts as leverage, pulling on them with each thrust to add more force. It hurt the first few times before a feeling of pleasure again overpowered any pain I was feeling.

The pounding he was giving me got to its fastest yet and his moans the loudest and I guessed he was getting close to cumming inside me for the second time. He moved his hands back to my hips and I started backing into him hard with each thrust to help him over the edge. Within seconds, his grip on me tightened, he gave a loud moan and I could feel him start to fill me up with his cum as large amounts of his seed flooded me with each thrust. This pushed me over the edge and I had one of the best orgasms ever, shooting stream after stream and my legs almost collapsed from the intense pleasure. It was a good thing I was over a sink and my cum landed there otherwise he might just have suspected something!

We both stayed like that for a couple of minutes panting heavily, exhausted from the powerful orgasms we both just had. I could feel him slowly softening inside me and, before long, he gently slid out of me and we could both finally regain our composure. He had shot so much of his sperm into me that I could feel it running out of my hole and down my legs. I pulled my underwear up so I could keep the juices inside me and wiped up what had leaked out with my finger and licked it off. It seemed to taste better after being inside me, maybe it was because it was a stronger orgasm than when I had sucked him off.

I adjusted myself as he'd pounded me so hard, my breasts had nearly fallen out of my bra. I neatened my hair a little and, as I turned around, he was zipping his fly back up. He leaned in and kissed me on the lips while grabbing my butt. He had to hold me up as my legs were still feeling like jelly.

"That was the best sex I've had since I can remember.” he said as he stopped kissing me. “Such a tight arse, I couldn't even last long!”

"I'm glad you enjoyed it." I said, blushing at the flattering words. "Shall we go back then?" I asked, glancing towards the door leading to the dance floor.

He agreed and he led me out of the toilets and to the bar area. We had a few more drinks and danced for a while, being unable to keep our hands off each other. Eventually he said he had to leave.

"Give me a call sometime." he said as he handed me his phone number which I immediately saved in my phone. We left it at that and I didn't stay much longer having had more pleasure than I'd expected before I came out tonight.

I arrived home at about 3am and it didn't take me long to fall asleep, dreaming about what I'd experienced that night. I was sore for a couple of days after that but it was well worth it as I had the best sex I'd ever had; I never expected I'd enjoy it with a guy so much. I decided that this would definitely not be the only time I did this and I would definitely be giving the guy a call.
 

AllDixNeedLuv69

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my mom dressed me up in a dress a wig and makeup when i was 13 for halloween--i must have been a sexy one because guys would ask me who i was and what school i went to--i never told tem because the last thing i needed or wanted was to be teased by friends at school
 

kydicksucker

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I'd been cross dressing for a few months at this point, but I'd never gone outside while dressed up before. I'd been to the shops a couple of times wearing one of my outfits under my normal male clothes; that's the closest I've ever been but just doing that turned me on a lot. Even under a fairly loose coat, I'm sure people could make out the outline of my breast forms. Since those little trips to the shops had got me so aroused, I was determined to do it properly so I decided that the following Friday I would go clubbing in town.

Friday came and I'd bought a new outfit just for the occasion. I slipped into my black lace low rise boy shorts , tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my D cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd been blessed with an arse that any woman would kill for so I could pull off wearing a skirt this small. The skirt had suspenders which I connected to my stockings. I finished off my outfit by putting on a tight black low cut top and adjusting my breasts so that I got some pretty good cleavage.

Next I had to put my makeup on. The good thing about having been cross dressing at home in private for so long was that I got a lot of practice putting make up on, so it was no trouble for me to put on some foundation, eye shadow, mascara and lipstick to make me look that bit more feminine. I already keep myself relatively hair free so all I had to do in this department was pluck a few stray hairs that my razor couldn't get to. I sprayed on some of my best perfume then got my wig out to put on. It was a wavy copper orange coloured wig that reached down to just past my shoulder blades.

After this I was done, so I went downstairs and to my front door. I reached for the handle but stopped for a second. I took a deep breath and thought to myself that I was about to go outside dressed like a woman, something that I'd never done before. So I composed myself, opened the door and stepped out into the outside world. Luckily, it was a warm night so I didn't need to wear a coat and could show off my assets. I spotted the taxi that I'd phoned for earlier and walked over to it. As I got in I could see the taxi driver looking at me through his mirror. He was looking me up and down with a hint of lust in his eyes. So far so good I thought to myself. I told the driver where I wanted to go and we set off.

On the way there, I noticed the driver kept glancing at me hoping I wouldn't notice. I blushed a little and smiled to myself, apparently I make an attractive woman! We arrived at the nightclub about ten minutes later and I got out, paying the taxi driver, then walking over to the entrance. As I got there, the bouncer gazed at me , waving me through without a second look. I stepped through the door and into a large building full of drinkers and dancers and pulsing with club music.

I walked over and sat on a stool by the bar. I was only there for a few minutes before a guy strolled over to me. He looked like he was just a shade under six foot, had an average build and short brown hair, well-built but not overly so.

"Hey, can I get you a drink?" he asked me.

"Sure..." I replied, my heart racing with excitement. He ordered a drink for me and himself and as we sat there drinking, we began to talk. We talked about the usual things, where I'm from, what I do, what I like. After a few more drinks, the conversation eventually took on a more sexual nature.

I told him I wasn't that experienced in sex which he said surprised him as he thought I looked that good that I'd be beating guys off with a stick. I giggled, putting my hand on his leg, which he seemed to like as I could see him harden a little in his pants. The alcohol was helping lower my inhibitions and the more I had, the more I flirted with him. We moved onto the dance floor and danced for a bit, grinding our bodies together to the music. After a little while, he placed his hands on my waist and moved his head towards mine, leaning in for a kiss.

I pulled back for a moment, hesitating, I'd never kissed a guy before. I could feel his warm breath on my face as he waited for my reply. I made my choice, lifting my head a little so my lips would meet his. A warmth spread through my body as we kissed and I wondered why I'd never tried this before. His hands slowly moved to my arse and he pulled me closer to him as continued to kiss. I placed my hand on the back of his head and started to involve my tongue in the kiss with him responding in the same way.

After a while, he moved his head away from mine, breaking the kiss and leaving me desperate for more. He leaned his head in towards mine and whispered into my ear.

"You want to take this somewhere else?" he asked, gesturing his head towards the nearby toilets.

I had a feeling about what he was hinting at, so I nodded and he took hold of my hand and led me across the dance floor and towards the toilets as my heart pounded at the thought of what was about to happen.

He opened the door to the toilets and pulled me in to join him, leaning me against a row of sinks in front of a large mirror and began to kiss slowly up and down my neck. My eyes rolling into the back of my head from the pleasure. He moved up, kissing my cheek as he went along, before moving onto my lips which he gently caressed with his, slowly moving his tongue in and out of my mouth. I moved my hands to his chest and, not wanting to have stopped kissing in the first place, I hungrily returned the favour and allowed my tongue to enter his mouth. After a couple of minutes, I broke off the kiss this time and I saw a glint in his eye as I knelt down on the floor and looked up into his eyes with a slight grin on my face.

He moved a little closer and I reached up, unzipped his fly and carefully pulled out his penis. It was pretty big already even though it wasn't even fully erect yet, about five inches I'd say.

“Mmm...so big...” I moaned as I stroked him, still looking into his eyes.

I leaned forward and started licking and sucking down the side of his shaft as I heard a soft moan. I slowly moved back towards the tip which I licked around in circles a few times before I couldn't wait any longer and finally put my lips over the head of his penis and began to suck his shaft down towards the back of my throat. I started off going about halfway before moving back to the tip while stroking the rest of his penis. I continued to bob my head up and down for another minute or two before I got the courage to start deep throating, gradually moving my mouth all the way down to the base of his penis so the tip was touching the back of my throat and my mouth was touching his crotch.

He began to moan loudly as I fought my gag reflex for a second or two. It calmed down and I stayed in that position for a good ten seconds before I gently drew back along the length of his shaft and allowed it to leave my mouth with a slight popping sound. I looked up at him with a cheeky grin on my face.
"You like that?" I asked while stroking him off, using the spit I'd left down his shaft as lubrication. A low groan was all he could reply with but it answered my question well enough.

My attention was then drawn to his balls, which were smooth and completely hairless. I leaned in towards them and, while continuing to stroke his manhood, took one of his balls into my mouth and set about rolling it back and forth over my tongue. I kept sucking on his ball for another minute before I let it slip out of my mouth. I could see by the look on his face that he was disappointed I'd stopped but he wouldn't be for long as I stopped stroking his fully erect penis and instead pointed it towards my mouth and took the entire length in straight away this time.

I moved my mouth up and down his throbbing member, each time taking it in all the way to the back of my throat before withdrawing so far that only my lips and tip of my tongue were touching it. After a while, he gently put his hands on my head and began to slowly push downwards each time I was going down on him. I took this as a sign he was getting close and I increased the speed of my sucking to which he responded with louder moans. As I stepped up the speed further, his moans got even louder and more frequent. I could tell he was on the verge of an orgasm so I started sucking as fast as I could, deep throating each time. Very quickly his hold of my head got tighter, his legs started to tremble and his manhood quivered as he orgasmed in my mouth.

He came in large spurts, each one hitting the back of my throat, giving me no choice but to swallow. He slowed down after another few squirts and, thinking he'd finished, I pulled him out of my mouth and he unexpectedly squirted two more jets of warm cum onto my face. I was taken aback for a few seconds as I wasn't expecting it, but then I ran my finger over my face and licked off the stray cum before swallowing it with a smile. He was breathing heavily now, clearly exhausted from an intense orgasm.

"God, that's the best blowjob I've had in ages." he said, in between his deep breaths.

I was pretty shocked at his comment; before tonight, I had never even done anything with a guy before. Sure I'd fantasised about it and practiced with toys, but I'd never had the real thing and here he was saying that the first blowjob I'd ever given was one of the best he'd had in ages!

"There's more to come yet, if you're up to it." I replied playfully as I got to my feet and leaned over a nearby sink, turning my head to look at him. I hiked up my skirt and pulled down my underwear just a little, sticking my butt out seductively.

“Lucky for you, I can go again straight away.” He said, smirking as he joined me at the sink.

I'd tried using a dildo anally at home, it was about the same size as the real thing that I'd just been sucking on. Even with lube, I only ever managed to get it in just past halfway but I was so caught up in the moment of having my first time with a guy that I was about to try taking the whole thing without anything to make it slide in easier and I didn't care!

I braced myself on the sink as he gently took hold of my head and kissed me. I reached behind for his dick and when I got hold of it, it was still rock hard. I guided it towards my hole and felt it prod at the opening.

“Shit, girls don't usually let me stick it in there!” he quipped.

I giggled as I probed my hole with the head of his dick. I couldn't wait much longer as I was getting hard just at the thought, so I backed into him to show that I wanted him to give it to me now. He duly obliged and slowly started pushing into my hole and my legs began to tremble. He kept pushing further, eventually getting in further than I had managed with a dildo which is when it started to hurt. I think he could see it was starting to hurt me because he forced in the last couple of inches to get it over with. There was a sharp pain for a few seconds but this was quickly replaced by an amazing feeling as his cock was inside me.

He started thrusting, slowly at first, allowing me to get used to the feeling. He quickly sped up as he got hold of my hips and increased the force of his thrusts. His balls were slapping against my arse with each thrust and I couldn't believe how much harder this made me. We were both moaning with pleasure, I'd never experienced this much bliss before now. I started backing into him each time he thrust to increase the force and this nearly put me over the edge. I was so close to cumming that I had to slow down and let him do the work.

He moved his hands to my breasts while still pounding me. It was a good thing I'd spared no expense with my breasts forms as he went to town on them, grabbing them with some force. I moaned with pleasure at his treatment of my breasts which seemed to please him. He started to use my breasts as leverage, pulling on them with each thrust to add more force. It hurt the first few times before a feeling of pleasure again overpowered any pain I was feeling.

The pounding he was giving me got to its fastest yet and his moans the loudest and I guessed he was getting close to cumming inside me for the second time. He moved his hands back to my hips and I started backing into him hard with each thrust to help him over the edge. Within seconds, his grip on me tightened, he gave a loud moan and I could feel him start to fill me up with his cum as large amounts of his seed flooded me with each thrust. This pushed me over the edge and I had one of the best orgasms ever, shooting stream after stream and my legs almost collapsed from the intense pleasure. It was a good thing I was over a sink and my cum landed there otherwise he might just have suspected something!

We both stayed like that for a couple of minutes panting heavily, exhausted from the powerful orgasms we both just had. I could feel him slowly softening inside me and, before long, he gently slid out of me and we could both finally regain our composure. He had shot so much of his sperm into me that I could feel it running out of my hole and down my legs. I pulled my underwear up so I could keep the juices inside me and wiped up what had leaked out with my finger and licked it off. It seemed to taste better after being inside me, maybe it was because it was a stronger orgasm than when I had sucked him off.

I adjusted myself as he'd pounded me so hard, my breasts had nearly fallen out of my bra. I neatened my hair a little and, as I turned around, he was zipping his fly back up. He leaned in and kissed me on the lips while grabbing my butt. He had to hold me up as my legs were still feeling like jelly.

"That was the best sex I've had since I can remember.” he said as he stopped kissing me. “Such a tight arse, I couldn't even last long!”

"I'm glad you enjoyed it." I said, blushing at the flattering words. "Shall we go back then?" I asked, glancing towards the door leading to the dance floor.

He agreed and he led me out of the toilets and to the bar area. We had a few more drinks and danced for a while, being unable to keep our hands off each other. Eventually he said he had to leave.

"Give me a call sometime." he said as he handed me his phone number which I immediately saved in my phone. We left it at that and I didn't stay much longer having had more pleasure than I'd expected before I came out tonight.

I arrived home at about 3am and it didn't take me long to fall asleep, dreaming about what I'd experienced that night. I was sore for a couple of days after that but it was well worth it as I had the best sex I'd ever had; I never expected I'd enjoy it with a guy so much. I decided that this would definitely not be the only time I did this and I would definitely be giving the guy a call.
I let men take me out to dinner movies dancing I m a guy but feel womanlier and I love men so much It nice for us gurl to get out in the public and enjoy ourselves Love you girl
 

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