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An Introduction to Crossdressing, Pt. 5

"My first time at a not-so-straight club is friendlier than I imagined."

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As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in a long time, I start to feel fearless.

Being fearless is one thing, but making sure we look hot is quite another, so we take the time to look each other over in the parking lot before going inside. Our makeup is superb and our outfits are very sexy, showing off more than most real girls would ever dare.

Jackie’s six-inch stiletto heels make him look to be all legs. While he is all in black, my floral topped thigh-highs and blouse are both fire engine red, otherwise we are identically dressed. Our short black skirts just come down to the tops of our stockings, barely covering our asses. If we bend in any way there is plenty of skin to see since we are wearing our tiny g-string panties. Although our sheer blouses are a bit too much in the daylight, they are a perfect tease as the sun sets, and also for the dim lighting inside the club.

After checking each other out a bit too thoroughly, which causes a few car horns to honk, we head for the door and our sexy adventure.

As we approach the door we see a rather large man stepping outside with a barstool in one hand and bottled water in the other. Now, the sight of a bouncer might instill fear in some, but for me it was a sign that the club was taking our safety seriously. While I had never been to a club quite like this, I have been to a few and from my experience the ones with bouncers were always less tolerant of problem customers.

Bill, the bouncer, says, "Welcome to the club," as he holds the door open for us.

As we strut by we tell him, "Thank you."

He tells us, "Have a great time."

Stepping inside, we notice a long bar against the left wall. There is a dance floor directly in front of us that looks to be about fifty feet square, which seems rather large for a club this size. To the right is basically a grouping of tables, with booths lining the right and rear walls.

As we are perusing the place a rather sexy lady of about our age comes up to us. She introduces herself as Susan and asks us, "Where would you like to sit?" We decide on a booth along the back wall so that we can see what is coming at us. As Susan escorts us to our booth, she asks, "Have you two ever been here before?"

I reply, "We have not, but we hope it will get busier than it is now."

She says, "It is early yet, but it will be filling up by about 9:30 p.m." Susan takes our drink orders and walks to the bar to retrieve our cokes and some menus. As she hands us the menus she says, "I love your outfits."

Jackie tells her, "It's our first time out fully dressed, and we wanted to be as slutty as possible." As we look through the menu he asks Susan, "What can expect, since it is our first time at a club like this?"

She says, "It is a pretty good mix of gay, bisexuals, crossdressers and a few straights." She also says, "While it can get loud, mostly due to the DJ that starts at ten, the crowd is very fun and there are never any fights."

Susan did warn us, saying, "With your outfits being so provocative you will probably be fondled a lot!"

We told her, "We are hoping for as much, since that's why we dressed this way."

After giving Susan our food order, Jackie and I started talking about our night to come. I told Jackie, "I don’t mind bringing others back to the room, but I don’t think we should leave the club separately for safety reasons." I continued, "Plus it would be more fun with three or four if we find someone we like."

Jackie agreed, saying, "I really just want to flirt, tease and have fun while we are here." He also said, "I am not really interested in taking anyone home except for you," and went on to say, "but if a really enticing opportunity comes along I won’t pass it up either." 

Susan came back to the table and said, "I have put your food order in," and then asked, "do you need a refill on your drinks?"

Neither of us needed a refill but I did ask her, "Do you have some time for a few questions?"

She said, "Sure, since it's still slow," and slid in next to me in the booth.

I asked her, "Are there any regulars that we need to stay away from?"

Susan said, "Not really, as long as you don’t mind being fondled." As she said this she placed her hand on my thigh and started gently stroking from my knee to the top of my stockings.

She continued, "When there are a lot of people on the dance floor it can get a little crazy, especially towards the middle." Susan added, "I have even seen people having sex while dancing but it’s pretty well concealed and always consensual." About this time her hand had reached my panties, and she was massaging my cock and balls rather aggressively.

She also said, "The manager won’t let it go on if he sees it himself, that's why we have the back rooms." Susan went on to tell us, "There are some gentleman that come to this club specifically to pick up girls like you, so just be careful."

Then she leaned to my ear and whispered, "My husband and I like girls like you too."  As she was whispering, she started sliding her middle finger inside me and I nearly came before she stopped. She suggested, "Have your fun here and then go home alone," then added, "If you really want to take someone home then just ask me about them before you leave." 

Susan hopped up and said, "I need to go check on your order and help a few other customers."

As she walked away, Jackie asked me, "What did she whisper in your ear, because you look a little flushed."

I told him, "She said her and her husband like girls like us." Then I told him what she was doing to me the whole time she sat next to me.

Jackie just grinned from ear to ear and said, "We are going to have a blast here."

Susan dropped off our food, gave me a wink, and said, "I will be back with drink refills."

As Jackie and I took our time eating we noticed that the club started to fill up quite nicely. We took note of others like us since that was what we were really into. There were some nice looking men, but we really wanted some gurl time, especially since we only had one night.

About the time that we finished eating, the DJ was getting set up and he got some music going. We both had to pee from all the coke we had been drinking so we headed to the restrooms. We were wondering how this was going to go and were pleasantly surprised to see that the restrooms were for either sex. We each did our business, and by the time we were done the DJ was filling the dance floor.

I told Jackie, "I'm not a very good dancer."

He said, "I don't think it matters, since we are provocatively dressed girls now and no one will be watching our dance moves." So we headed to the dance floor and tried to find some of the other gurls that we saw earlier.

There were only about thirty or so people on the dance floor and all were either guys or real girls.

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So we decided to just dance together for a while. When a slow song came up a couple of guys came over and asked us to dance. We each grabbed one, but stayed right next to each other. I must admit that it is a very weird experience dancing with another guy and trying to let him lead.

As the song got going my partner said, "Hi, my name is Steven and I love your outfit."

I thanked him for the compliment and let him pull me in closer as the song progressed. I noticed that Jackie's partner had his hand slowly working its way down to his skirt. It didn't look like Jackie minded at all, and they both seemed to be enjoying grinding their crotches together.

Their boldness seemed to spur me on and I reached down and grabbed Steven's ass with both hands. Steven seemed a bit startled with my move but then asked, "Do you mind if I do the same?"

I told him, "We are dressed like this because we want to be felt up, so please feel free to touch anything."

He slowly slid both hands down my lower back until he got to my ass and firmly squeezed both cheeks repeatedly. As a small moan escaped my lips I asked him, "Do you want to feel under my skirt?" Steven's hands moved under my skirt and gently massaged my ass as the song was coming to an end.

Fortunately for me the next song was a slow one as well, and we just continued fondling each others asses. Steven looked at me and brought his right hand around to my front. Still under my skirt, he started gently caressing my cock and balls, so I did the same to him. The difference was that my cock had already outgrown my skimpy g-string panties, so he was feeling skin while I was feeling Levis.

I was in another world as we moved with the music and his hands had me right on the edge. I whispered in his ear, "I am so close to cumming but I don't want it to happen just yet."

Steven surprised me by saying, "I really want to suck your cock."

I told him, "I'll let you suck me if you fuck me afterward."

He started dragging me off of the dance floor and said, "There are a couple of rooms in the back for just what we need."

I tapped Jackie on the shoulder and told him, "I am going in the back room with Steven and should be back in about twenty minutes."

He said, "Have a good time," and then, "I will be back at the table by the time you are done."

Turning back to Steven I said, "Lets go and have some fun!"

We went towards the back, past the restrooms, and there were a few more doors at the end of the hallway. All of the doors had tags hanging on the knobs that said vacant. We went into the first room and flipped the tag to occupied and locked the door. The room had a large leather couch and a small dining table with two chairs.

Steven immediately dropped to his knees, bringing my panties to my ankles. He then lifted my skirt and sucked my cock straight into his mouth. The warmth was intense, but just as suddenly he pulled back and then began sucking my balls into his hot mouth. As he worked his tongue all over my smooth balls my knees started to weaken. Noticing my instability he pulled his mouth off again and then backed me up to the arm of the couch.

As soon as my ass hit the arm he swallowed my cock again, working his tongue like a master. Following the same routine as before he abruptly pulled off my cock and went to work on my balls again. As he was superbly sucking and licking my balls I slowly spread my legs and leaned back, giving him full access to my ass.

He quickly took the hint, releasing my balls, and started working that magic tongue on my hole. Steven constantly varied his technique lapping up and down, side to side and working slowly deepening circles. Just when I thought it couldn't get any better he started nibbling on my ass. In between deep moans and 'Oh Gods', I told him, "I am about to cum," and he quickly swallowed my cock whole.

All I can remember from the next couple of minutes was grabbing the back of his head with both hands and pumping his face 'til I passed out.

I awoke to Steven pumping first two then three fingers into my ass. When he noticed that I was awake, he said, "I thought this might bring you around."

I thanked him for the spectacular orgasm and told him, "It's time for the fucking to begin."

He said, "That is why I was loosening you up a little, so there wouldn't be any pain."

As he said this I leaned forward to get a glimpse of his cock, and then I understood his concern. It was about eight inches long but even more impressive, it was about two and a half inches across. It was one fat bastard, leaking pre-cum profusely and throbbing to his heartbeat.

I quickly flipped over onto my belly with my ass hanging over the armrest and told him, "Go slow."

Fortunately I had pre-lubed earlier in the evening, expecting that I would be someone's slut. As he slowly eased into me I remember thinking that he was about the size of my newest butt plug. I also remembered that even with substantial amounts of lube, I still had trouble getting it all the way in me.

Desire is a driving force though, and since both of us wanted this, I knew it was going in no matter what. Initially he just moved the head up and down and side to side, never really pushing too hard. As I relaxed he started going in circles and applying more and more pressure until he slid right in, like it belonged there all along. Steven paused for a moment thinking I needed time to adjust, but the truth is I didn't want him to stop. So I shoved my ass back and told him, "Get busy!"

Steven started off slow and as his tempo increased so did my pleasure. At this point we were both moaning incoherently, and he told me, "I'm so close."

I pulled myself forward on the couch, withdrawing his cock from my insides, and quickly flipped onto my back. As I pulled him toward me he pushed my legs toward my chest and slowly slid back inside. As he started fucking me again I grabbed the back of his head, pulling his face to mine. I did this so that I could wrestle his tongue with mine while he filled my ass with his cum.

As we lay there thanking each other for the great fuck he slowly shrank inside of me and then withdrew. The cleanup afterward went rather quickly, and within a few minutes we were heading back toward the table. I was still a little unsteady, so my heels were in one hand and the other was wrapped around Steven. When we got to the table Jackie was sitting with another gurl that he had met while I was gone. When I sat down Steven and I again thanked each other for the great fuck.

As Steven walked away, after leaving me his number, Jackie said, "I want to know everything."

to be continued...

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Written by stockingluvr
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