Sarah Visits Chicago And Gets Lucky

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes.

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I was on a business trip to Chicago and staying at a nice downtown hotel. I decided to go out for the evening as Sarah. Well, what did I have to lose? No one knew me there and I would never see anyone that I met again.

I put on blue lace girls panties and a matching bra padded out with socks. It was a warm summer evening and so just I wore an ankle length blue cotton dress with puffy shoulders. The puffs hid some of my male appearance. I love the feel of an ankle length skirt around my calves. The way it brushes against my legs as I walk is so sensual. I did light makeup with just a hint of perfume. I wanted it to wear off by the morning. I put on a light white jacket and took my white purse to contrast against the blue dress. I could feel the dress moving against my panties as I walked to the elevator.

I walked out of the hotel, right through the reception area, dressed as Sarah. No one cared that I was a guy dressed as a girl. I forgot to mention that, while I always work hard to look like a girl, I don't pass. The best I can achieve is that at a glance, I am taken for a girl. Close-up and talking face-to-face, I am obviously a guy in a dress. I find that absolute confidence is the secret. If I start looking scared, people start to look at me more closely.

I found a nice little wine bar just around the corner but the bar tender told me, "I'm just about to close but I can serve you a glass of wine. Take your time; I still have a lot of cleaning-up to do." I sat at the bar knowing that I was dressed as Sarah. I've been going out dressed for so long, it just feels completely normal. The bartender didn't even blink when he served me.

I asked him if there was another bar nearby. He told me about a place only a couple of doors down from the wine bar. I sat there relaxing and enjoying my wine. Sitting there in a dress made me feel so good. By now in my life, if I have to go out dressed as a guy it actually feels odd. Although, I am never totally a guy. I only ever wear girls panties and jeans even when I appear to be a guy. Also, I always carry a shoulder purse. They are such a wonderful invention. I can't imagine trying to stuff all of my belongings into my pockets. Before I left the bar, I used the ladies room. I love using the womens bathroom. It feels so naughty pushing open the door labeled 'Women' and the room is always so much cleaner than the mens.

I finished my wine and went in search of the next bar. I found it quite easily but it was not at all what I was expecting. I expected a normal 'dive' bar, TVs, music, pool tables but what I found was very different.

The entrance was up a flight of stairs. The only indication from the street that it even existed was a name on a plaque beside the entrance but otherwise it was very nondescript. I went up the stairs, probably encouraged by the glass of wine. I found a small crowded bar. Talk about a contrast. Remember, I was a guy dressed as a girl; wearing a long light blue dress with a white jacket and a white purse. Everyone else was in black leather or denim. After a while I did identify some real girls in the room but not many. They were in black and just as heavy leather as the men.

I ordered a drink and found a seat at the window looking out over the street. I sat there just thinking about the situation. I was the only person in the room not in black and I did stand out a bit. Well to be honest more than a bit. I guess it was a biker bar but they treated me with utmost courtesy and said nothing against me. I never felt the least bit threatened or unwelcome.

I sat there hoping that a guy would come over and chat me up. I was so horny from being out as a girl. I really wanted sex that night. However, no one paid any attention to me. Good in a way, attention could have been negative too.

I finished my beer and had another. It was so exciting just sitting there knowing how I stood out. I am more than a bit of an exhibitionist. When I first started going out dressed, that alone was a thrill. Now being out dressed feels normal, I need to be centre stage to get the same adrenaline rush. In this bar my heart was definitely pounding. I loved it. Again I used the women's restroom before I left.

I went back to my hotel. The manager nicely called me over by name and asked if Chicago had been good to me. He could obviously see I was dressed as a girl. No two ways about it, a powder blue dress just shouts 'girl'. I said, "Oh yes thank you."

I didn't want to retire to bed just yet and so I went to the hotel bar for a night cap. I sat there thinking about where I had just been. I remember how I stood out, the only person in the place dressed as a feminine girl. However, I never felt at all unwelcome.

I was sitting at the hotel bar enjoying a white Russian when a cute girl came in. After a few drinks I get a little more talkative. We started chatting and I told her about my evening. She said she knew the place and it was a famous gay biker bar. She smiled and said, "You definitely would have stood out."

We chatted about how I love to dress as a girl. She was sitting close to me and so I rested my arm across the back of her chair and sensed for her reaction. I didn't want to spoil what we had going but I did find her attractive. I explained that although I love to dress as a girl and have played around with guys in the past, I like women for real love. By then she had not backed away so I let my hand rest on her shoulder. She smiled and said I was the best of both worlds.

A crossdressing boyfriend can always lend you a pair of stocking in a pinch and always has a lipstick handy. Also, he never gets bored shopping for clothes. Let him try on a dress now and again and he is happy all afternoon.

I finished another white Russian and I was desperately trying to think of an excuse to invite her back to my room when she asked if I had any other girls clothes with me. I said sure, I'd love to model them for you. She just smiled. I knew what she was thinking.

We finished our drinks and left the bar. I kept my arm around her as we walked to the elevator. I wonder if a casual passer-by would think that we were just two girlfriends out for the evening. Who cares? Gay, lesbian, transgender or straight these days does it matter?

In the elevator I pulled her towards me and gave her a kiss. At first, we just touched lips but then started a deep French kiss. She could feel my bra straps when she stroked my back.

In my room we kissed again and then she said, "Go and change, Sarah." I went to my suitcase and picked out another outfit I had brought with me. I didn't let her see what I had and went into the bathroom to change.

I had bought a red pleated school girl mini skirt and a white short top that tied across my chest. I had not expected to wear it out but I love dressing naughty in my room. Now a really cute girl was going to see me wearing it.

When I emerged, she said, "Oh my, honey."

I did a twirl for her and I'm sure she saw my panties as the skirt rose up.

I sat on the bed beside her and kissed her again. I held the side of her face and stroked her as we kissed. She put her hand on my leg and to respond I ran my fingers across her breasts. She just kissed me deeper. I cupped her breast and she slid her hand up under my skirt. I jumped when her fingertips reached my panties. She traced the shape of my cock through my panties as we kissed.

She said, "Nice sissy girls panties. Lift up your skirt and give me a good view." I stood in front of her and lifted my skirt so show her my blue lacy panties. With a very obvious bulge in them. She smiled at me and traced my cock through my panties. I had to be careful not to cum just yet.

Then she slid her hand in the side and touched my cock, skin to skin. She traced my cock with her finger tips and I lowered my hand to her leg. I slipped it up under her skirt and let it rub the front of her panties. I know mine were more sissy girly; hers were fairly plain white but there was a real pussy inside.

I slid my fingers in the side and let a finger slide into her pussy. It was already so wet that I easily found her hard clit. I started by slowly circling it and letting my finger tip run across it. She was dripping wet and starting to squirm. She wrapped her hand around my cock and held it while we kissed and rubbed each other for a bit.

She bent down and licked the head of my cock. Slowly she slid her lips over it and ran her lounge around my foreskin. She looked up at me smiled and licked her lips. I rested a hand on her head as she gradually took more of me into her mouth.

With my fingers still playing with her pussy, I don't think either of us could have waited much longer. We fell back on the bed cuddling and kissing. She had to have felt my hard cock against her leg. I rubbed my finger across her clit and she moaned.

I pulled back a little and smiled at her. Then, I moved between her legs and let my cock slowly touch her pussy. Slowly I slid it inside her. She held me and helped me to slip it in. We were fucking as two girls, our skirts pulled up and our panties tossed off on the bed beside us. I moved in and out of her while we kissed until she wrapped her arms around me and pulled me hard into her. I could feel her orgasm coming and so I let go and filled her pussy with my cum just as she exploded herself. She pulled me so tight into her.

Afterwards we lay back on the bed and enjoyed the moment.

I fell asleep and when I woke-up a few hours later she was gone. A wonderful visit to Chicago and a memory I will never forget.