A Night At The Bar Alone

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Vanessa has fun on her first night out alone.
1.8k words
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The next morning I woke up and the bed was empty. That was not unusual as Cindy often gets up early to workout. As I was lying in bed, I looked down and noticed that I was still wearing the black laced teddy that Cindy handed me before bed. It felt nice up against my body as I rubbed my hand along it. I couldn't help think back at what had happened last night. I didn't know how Cindy was going to treat me after watching what I had done with those two guys. I also thought about how much I liked the attention I was getting while walking around the club wearing my high heels and sexy little mini-skirt. I thought about how big Tony's and Carlos's cocks were compared to mine.

"Would Cindy even want to fuck me again or does she prefer much bigger cocks?" I wondered as I touched my little cock.

I got up and showered. I put on some shorts and a tee shirt and made some coffee.

Cindy came back from the gym in her colorful workout clothes and a little pony tail. She is so cute. She looked at me as if nothing had happened and thanked me for making coffee. I was a bit taken back that it was just a normal Saturday. She then rushed upstairs and said she had an appointment and would be gone most of the day. I lied and said I had a busy day too.

As I sat on the couch, I noticed a few new ladies fashion magazines on the table. I picked one up and started going through it. There were articles on makeup and fashion trends. There were ads for sexy shoes. I was really into reading about all these feminine issues.

Cindy was dressed and ready to head out the door in no time. She also looked great in her casual clothes with a nice sundress and matching hat. She looked at me as I was looking through the magazine.

"Well I am glad you are finding those magazines helpful," She said with a smile on her face. "We girls need to look good for the guys,"

She then walked up and gave me a kiss on the cheek.

"I had fun with Vanessa last night and I am looking forward to another Girls night out." She whispered

I wasn't sure what to say, so I just smiled.

Finally, I went upstairs to change. When I opened my underwear draw, there were several pairs of sexy panties neatly folded. I also noticed that some of the outfits Cindy purchased the day before were hanging in my closet. There were also several pairs of new heels. Everywhere I looked, I was reminded of my feminine side.

After a few hours of doing not much more than looking at Cross-dressing sites and YouTube Videos of practicing makeup, I got a text from Cindy.

"Hi Vanessa, meet me at 8pm at the hotel bar downtown"

I was confused. Was she serious? Did she really want to me go out alone?

I went upstairs to get ready. I showered again and removed any remaining body hair. I put on my new panties. My legs felt so soft and smooth. I then started to practice what I had learned from my makeup lessons. I went with the Smokey eyes look. I choose a nice pink lip stick. I looked so pretty in the mirror. I then put on a white miniskirt and a black little blouse. I put on a pair of clear 5" heels. I picked a new wig that was mostly dark blonde with highlights. I spray my neck with some perfume, picked out some earrings and grab my purse. As I opened it to put money and my id in it, I noticed the condoms were still there. I decided to keep them just in case. I then rushed out the door.

It was a little awkward driving in the heels. I also tried not to make eye contact with anyone while driving. I got to the bar right at 8pm. I then received a text from Cindy saying she was running a few minutes late. I ordered a drink and took a seat at the bar. There must have been a convention in the hotel as there were several well-dressed business men.

It was already after 9pm and no word from Cindy. I was finishing my 2nd martini and had a nice little buzz on. Just then, nice looking gentleman came up to the bar and stood behind me. He then looked at the bartender.

"Charlie, I want to buy this young woman a drink"

I couldn't believe a man was buying me a drink. I gave him a flirtatious smile.

"Thank you, Honey! Aren't you sweet?" I said to him with a sexy little smile.

He sat beside me an introduced himself as Jerry. Jerry was a Dr. from Texas. Our drinks came and we made small talk. He mentioned how boring the other doctors were. After a few more drinks, we were laughing and he started putting his arm around me. It was getting louder in the bar so often he had to whisper in my ear. Each time he would take a deep breath.

"I love the way you smell" he said as he closed his eyes.

He then put his arm around me and pulled me in to kiss me. I felt like I was going to melt in his arms. I had forgotten all about Cindy by this point.

Jerry got up to go to the bathroom. The bar was getting more crowded with the convention. Jerry came back and handed me an envelope. There were 3, $100 bills and a key to his room. The envelope was marked "3101",

"There are too many people I know in here. People will start talking. Just meet me upstairs in 30 minutes."

He walked away.

I didn't know what to do. He was really good looking and I could use the money. I then picked up my purse and walked through the bar towards the elevators. Several guys tried to talk to me and one offered me a drink. I smiled and walked on.

I got on the elevator and two older guys joined me. I could see that they had Dr. on their name tags. They were both drunk and checking me out.

"Hello ma'am! Would you care to joins us for a drink at the rooftop bar?"

They were so drunk I don't think they knew I was a guy.

I decided I would have a little fun with them. They were behind me as I was looking towards the door. I knew they were checking out my ass.

I turned my head back in a sultry way and said "Why the rooftop? I am sure you have a minibar in your room."

They didn't know what to say. Just then the elevator stop and the door opened for a young couple to get in. They too were drunk and laughing. I backed up all the way so my ass was now up against one of the guys. I reached around and grabbed the guys cock while starring forward as the doors closed. I started to tickle him and rubbed my ass on his lap without saying a word. This went on for a while and as we both were enjoying it.

I then said to him without looking at him, "Honey, will you take me to that expensive French restaurant tomorrow night?"

He cleared his throat and responded, "Well of course dear, whatever you want".

The couple then got off a few floors later.

I gave the guy with a now rock hard cock a final squeeze as the elevator stopped on 31. "It nice meeting you but I already have a date tonight".

He handed me his card and asked if we were still on for tomorrow. I looked at the card and said "Well Dr. Smith, Surgeon-in-Chief, I will call you"

As I got off the elevator I got another text from Cindy.

"Sorry hon, I got tied up this evening. I hope you are having fun with the Doctors. Remember, pretty girls can get these guys to give them anything they want." She must have had this planned all along.

I got to 3101 at the end of the hall. It had a double door. I figured it was a suite and it was. I walked into this beautiful room overlooking the city. My heels could now be heard walking across the marble floor. I went to the bar and made myself a drink. Just then the door opened and my Texas Doctor arrived.

He seemed a little more drunk but now.

"I am glad you decided to take me up on my offer" he said as he poured himself a drink.

He started to tell me about the show but I was so horny at this point, I couldn't resist. I walked over and stood in front of him.

"I want to be a good little nurse Doctor." I said as I undid his belt and unzipped his pants. I got down on my knees and pulled out his cock.

"Oh, I have wanted to suck this cock all night" I said to him as I put his cock in my mouth. It was a lot smaller than the other guys. It was only about 5" and skinny so I could get most of him in my mouth. I started to taste his Pre-cum so I stopped. I then lead him into the bedroom.

"I want you inside of me." I have never had more than a finger or two in my ass but his small cock would be the perfect size. I got my purse and handed him a condom. There was already some tranny porn on the Pay per view with some lube on the table besides the bed. I guess he must have jerked off earlier.

I took off my panties put some lube on my fingers and lubed my ass. I then put some on his condom. As I bent over the bed he came up behind me.

"Are you ready for me bitch?" He said as he grabbed my hips.

I thought it was going to hurt but was ready for it. As he held my hips his cock entered my pussy ass. It didn't hurt much at all. It slid right in. He started to pound my ass.

"Do you like that you little slut?" He said as he fucked me from behind.

I could hear the porn on the TV of a shemale also getting fucked. It felt so good; I just wished I had another cock to suck while he fucked me.

"Oh yes, Fuck me you big stud". I said as I really was enjoying it.

Just then he came and filled the condom with his cum. He pulled out of me as we both collected our breathe.

I went into the bedroom to clean up. When I came out, he was passed out on the bed. I collected my panties and purse. I still had a few condoms left. I didn't want the night to end. I picked up my drink and headed out the door.

To be continued...

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8 Comments
The_NexusThe_Nexusover 5 years ago
Fun fun fun!!!

Please write many many more stories!!!!!

cdCindy1cdCindy1over 5 years ago
I love this story

Great story. I wish my wife would accept my cross-dressing because I'm a sissy cocksucking CD who loves getting fucked by well-hung men. I wish my wife was watching and was supportive like Cindy (take note that my CD name is Cindy).

I also want to tell you that I love your photo on your bio - you look really sexy. I would love to have a hot lovemaking session with you.

Please tell more stories. I can't wait.

fuzeetafuzeetaabout 8 years ago
Loving it!

More please, so hot, I'm really loving this! X

BrendaNWBrendaNWover 8 years ago
hot story

Please continue.. love to read more about their adventures

AnonymousAnonymousover 9 years ago
Please continue

I can't wait for you to continue the adventures of Vanessa & Cindy. This is similar to what my wife & I have been doing for the past year, ever since I told her about my cross-dressing. We have lots of fun with hot sexy men. I'm now a cocki-sucking addict and I love getting fucked by both my wife and by well-hung men.

Please continue. It's been too long since the last story.

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