Sarah Visits Chicago

I was on a business trip to Chicago and I was staying at a nice downtown hotel. I decided to go out for the evening dressed 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 panties and a matching bra. It was a warm summer evening and so just I wore an ankle length blue strappy sundress. I put on a light white jacket over it and took my pink purse to contrast against the white. I put on light makeup with just a hint of perfume. I wanted it to wear off by the morning.

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 I don't pass. At a glance, I am taken for a girl but not close-up and not if we are talking face-to-face.

I found a nice little wine bar just around the corner but the bar tender told me, "I'm just closing 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, dressed as Sarah. It just felt so normal to be out as a girl. The bartender didn't even blink when he served me dressed as a girl.

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.

I finished my wine and went in search of the 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 so different.

The entrance was up a flight of stairs. The name was 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 sundress with a white jacket and a pink purse. Everyone else was in black leather. After a while I did identify some real girls in the room but not many and in just as heavy leather as the men.

I ordered a drink and found a seat at a counter 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 gay bar but they treated me with utmost courtesy and said nothing against me.

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 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 sundress 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'm 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 bar. She smiled and said, "I bet you definitely 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 my second 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 she was a lesbian. Who cares? Gay, lesbian, transgender or straight these days does not 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 held 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 micro mini skirt and a white short top that tied across my chest.

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

I did a twirl for her and I'm sure she saw my panties show 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."

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. We kissed and rubbed each other for a bit.

I don't think either of us could have waited much longer and so we pulled off each other's panties and resumed kissing.

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. 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.