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Adventure in St. Louis

Cassie's adventures on a night in St. Louis

Work can really suck. At this moment I am sitting on an airplane wrapping up a three day business trip. Thank goodness I know how to make work fun. If someone gives you lemons, I say make lemon meringue pie, because lemonade is not good enough. What I am getting at is you have to make the most fun in your life, because life is too short. If you have a passion, make the most of it and enjoy your passion.

My passion I have to keep hidden most of the time, but when I travel sometimes I am able to “let it out of the closet”. I am a cross dresser and have been doing it for over twenty years. I can go years without dressing and acting up, but a year ago it became over powering again and I have been enjoying my feminine side more and more.

I just turned forty and I decided that since I had not dressed as a woman for over five years, if I was going to do it again, I was going to do it right. I spent almost a year buying all the things I wanted and also doing the correct research on where I wanted to go to be my alter ego. The past three or four months since I have been dressing again have been so much fun (and sometimes crazy) I can’t see myself ever letting Cassie go away

Cassie, short for Cassandra (I also have gone by Sandy) is the name I use when I dress. The smartest thing I ever did was take the year to be fully prepared so when Cassie is out, she is 100% ready. I have had body waxing, ear piercings, make up lessons, spa treatments and many other luxuries to become more feminine. I also lost about twenty pounds and got myself in the best shape of my life.

Let me tell you about my recent trip while it is still fresh in my mind as I am flying home. I was on a trip to St. Louis where I was staying for two nights. I arrived on Monday around 6 PM, which allowed me time to do a little shopping before I went to my hotel. Being familiar with the area and the malls, I knew where to shop to pick up some new items. I bought new black fishnet thigh high stockings, new black lace panties and a sexy black tank top dress. I grabbed a quick dinner at the mall and then I was on the road again.

My next stop was a liquor store where I bought a bottle of Grey Goose Vodka, a “nip” of Grand Marnier, a bottle of cranberry juice and a plastic martini glass. I checked into the Days Inn and requested a specific room...again I always prepare, I know where I want to stay and which room so Cassie can be totally comfortable. After returning from the ice machine, I unpacked my suitcase and my shopping bags and made myself a beautiful cosmopolitan martini. I always travel with a martini shaker for Cassie’s enjoyment. I took a hot shower shaving any area of my body that needed some touching up.

I had finished my third martini when I looked in the mirror at the finished product. Cassie was in her full glory. My new sexy tank top dress with my new fishnets looked great. My look could be best described as classy hooker. My dress was about four inches above my knees. It was accented with three inch black patent pumps and a red leather jacket that was tight and very short not quite to my waist and the sleeves only went a little past my elbow. I had on silver jewelry, bracelets on both arms a choker and long necklace featuring a cross that dangled in my cleavage of my scooped top line. I had a 34B black lace bra with small breast forms and a gaffe to conceal my manhood under my new lace panties.

I wore long “dangle” earrings (silver of course) and had painted my nails a fire engine red to match my lipstick. I wore my dark red wig that featured curls and went down one inch below my shoulders. I smiled at myself in the mirror and touched up my mascara and rouge before grabbing my fake Prada handbag and strolled out of my room. I also slurped down my fourth martini!

The room I chose was right next to a side exit and entrance of the hotel. This allows me more freedom of going in and out of a hotel as Cassie or my male side. My destination was an adult book store about four blocks away from the hotel. I had visited this book store on my last trip to St. Louis, but was not dressed as Cassie. The book store was pretty good sized and featured about 30 video booths, some of them with glory holes and sliding walls that allowed you to see the person in the booth next to you. I felt it would be a great place to be able to suck some cock! Yes, when I get dressed, I am the biggest slut on the planet. I am straight in my everyday life, but when Cassie is out, all I want is cock. The more the merrier!

It was a warm evening, so I did not need to wear a heavy coat over my jacket, so I was looking pretty hot in my short dress and high heels. Well, here is when the strange thing happens. I was only two blocks from the hotel and a police car pulls over as I am walking down the side walk. I stopped to see if they were stopping for me, and sure enough a police officer steps out of the patrol car and approaches me.

“Good evening.” He says

I am a little surprised and suddenly very nervous. I am barely able to squeak out in my feminine voice “Good evening, officer.”

“Ma’am I am sorry to bother you, but we have had calls of a lot of prostitution in this area. By no means am I considering you to be a prostitute, but this is probably not a good area for a woman to be walking by herself, if I may say, especially dressed so provocatively.”

I was a little unsure of what to say, so I kept quiet and thought about the situation. I decided very quickly that I had done nothing wrong and thought the best thing to do was tell the truth. The worst thing would be to lie and get caught lying and spend some time being questioned. As I started to explain my story, I looked at the policeman more closely. He was a fucking stud! He was about 6’ 3” tall with a big chest and very strong. I would guess he was 28 to 30 years old.

He was looking at me still waiting for a response as I took a very deep breath. “Officer, thank you for the warning and you are correct I am not a hooker. I know my outfit is a little suggestive, but that is how I dress all the time.” I finally was able to utter.

“I can offer you a ride somewhere, as long as it is close by.” He replied.

Another deep breath; in through the nose, out through the mouth. I looked at his chest and saw a name tag that read Walters. “Well, Officer Walters. You see, I mean…ok, here’s the story. I am not really a woman, I am a cross dresser, a man that dresses and acts as a woman. I was walking down to the adult book store.” I said as I pointed in the direction of the store.

I could tell that I caught him off guard and that he was not sure how to reply. I could tell he was now the one thinking and when he spoke next, I thought he was stalling for time to decide what to do next. “May I ask your name?”

“Legally or what I would like you to call me.” I asked

“Whichever you prefer, you are not under arrest or even being questioned.” He replied.

“Cassie.” I said.

“Cassie that is a pretty name. Do you live in the area or are you a visitor?” He asked

I was wondering where this was going as I saw cars slow down to watch Officer Walters questioning me on the sidewalk. “I am a visitor; I am staying at the Days Inn.” Again I pointed, but this time in the opposite direction.

He looked me over with his eyes and I started to feel more comfortable. “I have an idea; let me give you a ride back to your hotel. I get the idea you might have a fun time at the book store, but I think you are going to be in a bad situation on this street, especially if you stay out late.”

I didn’t hesitate in replying. “Sure, I trust you and I don’t want to get hurt.”

Before I finished replying he was already headed towards his car and clearing off the passenger side of the front seat. After moving his paperwork and other items, he motioned me to sit down and then closed the door behind me. I watched him walk in front of the cruiser and enter on the driver’s side door. He had a very handsome face and I was really starting to get horny, thinking of sucking his cock.

He sat down and smiled at me and pulled into traffic. He made a U-turn in the middle of the street and within 30 seconds he was pulling into the entrance of the Days Inn. “Where should I drop you off?” He asked.

“Down at the far end of the hotel.” I said. “It was very nice of you to do this, I am just sad that now, I won’t have any fun tonight, Officer Walters.”

“Please call me Barry. Can I tell you something of a personal note?” He asked.

“Of course Barry, you are my knight in shining armor tonight, te hee.” I laughed.

He pulled in the parking spot I motioned to and then he gave me a sign to be quiet as he spoke into his microphone attached to his uniform at the chest. “This is Walters in F352; I will be out of communication for the next 10 minutes.” He smiled to me as he finished saying this.

“10-4 F352” A reply came over the radio.

“They think I am going to the rest room or taking a personal break.” He said to me as he opened his door. “Let me walk you to your room.”

Again I admired his shape and now had been able to see all of his features. He had a very sharp pointed chin and had a good amount of black “stubble” on the chin and cheeks. He had a masculine nose with deep brown eyes and short black hair. His hands were enormous and his biceps were very pronounced, I thought he could pick me up in one hand. I was noticing all the features as he walked in front of the car and opened my door. He extended a hand to help me out of the car.

I pulled out my room key and inserted it into the lock on the door to enter the hotel. I felt him breathing down my neck behind me and a very subtle touch on my shoulder. I was getting more excited by the second and I shook my ass a little as I strolled down the hallway to my room. Unfortunately the walk was short and I thought Barry would leave once I opened the door.

“Too bad you are on duty and can’t come in for a drink.” I said as I opened the door to my room.

“I don’t need a drink, but I will come in if you will let me.” He said.

I barely had the door open and he grabbed me from behind and lifted me into the air. “You are the sexiest CD I have ever seen, and you are hotter than most of the girls I have been with.”

He spun me around and kissed me flush on the lips. My mouth opened immediately and I felt his tongue shoot inside my mouth. He engulfed my mouth and the kiss went on and on, I never wanted it to stop. I could feel his rough new beard against my smooth skin. His hands were all over my back and sliding down lower to my ass. As our kiss continued, I felt his hands lift up my dress and slide underneath me to feel my exposed ass cheeks.

Our kiss finally stopped and as he lowered me down and held me close, I could feel his hard cock straining against his uniform pants and against my belly. “Cassie, I have to leave in a few minutes, as I can only be out of contact for about ten minutes. “

“No problem Barry, I specialize in quickies.” I said as I dropped to my knees.

I unzipped his trousers as he undid his gun belt. I couldn’t wait to taste his cock and to swallow his cum. Within ten seconds his trousers were around his ankle and I was sliding down his Jockey boxer briefs to the same location. His dick sprung out like a jack in the box as soon as I slid his shorts down. It was my idea of a perfect cock; about seven inches long and pretty thick. As I took a hold of it for the first time, I thought, how lucky am I? Why he is here with me, but before I could take the thought any further I slipped my tongue on the underside of his beautiful penis and had my first taste.

My biggest turn on is to make someone else cum, whether it is man or woman. I was going to try and make this awesome hunk of man cum in my mouth very quickly. He was fully aroused, so after my first lick I put my lips around his manhood and quickly swallowed his entire cock. This resulted in a very loud moan from Barry and him placing his hands on the back of my head.

I pulled off of him and said. “Fuck my mouth baby, I want you to gag me and cum inside me.”

Then I went right back to work on his monster. He was thrusting his hips and pushing my head down on his cock and I did gag a couple of times, but I did not stop as I could feel his explosion coming. It only took me about ten full plunges down on his cock until I tasted the first shot of cum hit the back of my mouth. Yummy, I thought as Barry shoved his cock hard into my mouth and held firmly to the back of my head with his hands.

My mouth was filled with man juice and I eagerly slurped it down my throat. I deliberately left some in my mouth and as he pulled out, I let a trickle of cum seep outside the corner of my mouth. When Barry looked down at me, I licked the few drops from my face and then softly stroked his cock to insure I had every last drop of his cum inside me.

I was in 7 th heaven, but I knew my lover was leaving. I guided him to the bed and had him sit down on the edge. I went to the bathroom and moistened a wash cloth and brought it and a hand towel back to the room. I gently washed off the lipstick off of his face and then dried him off. Next I took a deep slurp on his cock with my mouth to insure I had all of his cum inside me and then I washed his cock and balls with the wash cloth and then dried him off. Lastly I lifted his balls and licked his asshole and stuck my tongue inside it to see his response. After ten or fifteen seconds, he pushed me away, but I returned with the wash cloth and towel to clean and dry him.

When I finished cleaning him up, I helped him pull up his shorts and trousers and watched him put back on his belt. “You know Cassie; that was fantastic. I might have some time after work later to come back if you like?”

“Oh, baby! Please do, I love your cock; maybe you can fuck me next time.” I said eagerly.

“Well that is not until 2 AM, that is over four hours from now. “ He said.

“No problem, if I am sleeping just call my cell or knock on the door, I will still be dressed and ready for you.” I replied.

“What will you do until then? It really is dangerous to be out there walking by yourself.” He said.

“You are right. Tomorrow I have a few friends coming by, so maybe I will just rest, but I would love more cock, te hee.” I said.

“I have a friend on the force that may be available. I know he would want to come by if he can.” Barry said.

I guess I don’t have to go on with the rest of the dialogue, as obviously I wanted his friend to come by. I gave him my Cassie cell phone number for his visit later and hopefully to hear from his friend. When Barry left he kissed me good bye and I was pouring another martini before his engine started. I cleaned myself up taking a quick shower and putting lotion and powder all over me before redressing in my same outfit.

I sipped my martini and then I decided to set up my secret cameras. As I told you before, I spend almost a year buying new things to make sure when Cassie came out to play she could play the way she liked. I was going to use the camera tomorrow for my in room visits, that I will tell you in another tale, but since I might have one or two visitors tonight, I certainly wanted that captured.

My cameras were very small, smaller than a web cam that you would attach to a computer. I attached one to the top of the picture above the head of the bed and another above the picture above the TV on the opposite wall. They would record onto a box that was inside my briefcase, it cost a lot of money, but the shots were amazing. I would love to watch them later, as it is so cool to watch myself get fucked, especially by strangers.

I barely had them hooked up when my cell phone rang. It was Barry’s friend Ty and he wanted to come over in ten minutes, he just finished his shift and wanted to come over right away. I agreed and couldn’t wait to have him arrive. I poured myself another martini and sprayed some perfume on me. I was now feeling pretty drunk and Cassie has been known to get pretty wild when she is tipsy. I brushed my hair one more time and touched up my lipstick.

“Crap.” I said to myself as I looked at my martini glass and it was almost empty. “What the Hell?” I poured another cosmopolitan and really felt drunk.

There was a knock on the door and I eagerly answered after peeking through the peep hole. I saw a big black man at my door….”Who is it?” I asked

“It’s Ty, Barry’s friend.” A voice said.

I opened the door and saw Ty. He was older than Barry probably mid thirties and much heavier probably 250 pounds. He was not tall; I would guess 5’ 9” and pretty fat. His face was very handsome, very dark with dark eyes and short curly hair. He was very anxious to get inside.

“Come in baby.” I said as I motioned him inside.

He jetted inside and I closed the door, he looked at my bottle of vodka and asked if he could have a small drink. I poured him a shot of vodka on ice served in a fancy Days Inn Styrofoam cup. I did a little spin in front of him and looked at his beautiful eyes.

“So, do you approve?” I asked.

He chugged the vodka and said. “Oh you are fine, baby. I only have a short time I can spend, are you ok with that?”

I nodded yes and he set his drink down and guided me to the bed. He was so dominating and I loved it. He slid me down on my back and started kissing my face. I accepted his tongue as it slid into my mouth and he started to tongue the roof of my mouth. I was so turned on as this big black man was on top of me and I knew he was all mine.

His cock was already hard and I could feel it through his jeans as he kissed me and started to move his hips a little so that his bulge was rubbing on my leg. After he finished kissing me, he stood up and took off his polo shirt, tennis shoes and jeans. He was wearing no underwear and he had a massive cock, at least eight inches and wide.

“Oh, baby. Bring that dick over here to me!” I begged.

I changed position so that I was lying on my back, sideways on the bed and let my head hang over the side. Ty saw my position and stood right in front of me and fed me his cock into my mouth. I struggled to get my lips around him, but he shoved hard and I swallowed almost half of it. I turned my head slightly and felt the rest of his cock slide into my mouth and partially down my throat. I was getting face fucked by a big black cock, can anything be better? Ty continued to grind me for about two minutes and then I felt him pull out. He pushed me aside and lay down on his back on the bed. I immediately went to work licking his balls and asshole while I stroked his big fat dick to keep it hard. My tongue and hand were doing the trick as I knew he was getting more excited.

“Come on sweetie, suck my big cock again. I want to see you take that whole thing in your mouth. “

I looked into his eyes and then raised my head to get a good angle on his cock. I also knew the camera above his head was going to get a great angle of me blowing him. I went down him and swallowed his whole dick in less than three seconds. Then I started acting like a plunger going up and down on his shaft at full speed. I made slurping sounds every time I came off his cock and put a smile and look of bliss on my face.

“Fuck baby that feels good.” Ty said as he pulled my head down on his cock to increase the power of this face fucking. “I am going to fill your mouth with a big huge load of spunk.”

“Please baby, give it to me.” I said in between sucking.

He pushed me off his cock and had me lay crosswise on the bed. He straddled his face with his knees and then fed his cock to me again. This time he had lots of leverage and really started pounding me. His big balls were slapping against me chin as he thrust his huge cock in my mouth. I could sense his orgasm about a second before his first shot of cum. It was thick and creamy and more than a mouthful. I swallowed gladly but he pulled out when I was full and then he stroked more cum out of his cock and it shot over my cheeks and forehead. After swallowing his load, I went to work on the clean up and sucked another couple of cum balls from his shrinking cock.

“Fuck baby, you are fucking good! You can suck my cock anytime.” Ty said.

“Thanks honey, I will suck it anytime and boy would I like to have your soldier fuck me silly.” I replied.

“Oh, I am baby. You see my old lady doesn’t give me any pussy, so I am ready for a good fuck too.” Ty said.

My eyes lit up and I immediately started stroking his cock to try and get it hard again. I guided him back down on the bed, so that I could go to work with my mouth to get him excited. He handed me a wash cloth from the bedside table so that I could wipe off the cum on my face, but I didn’t stop licking his balls and cock while I cleaned up. I could see a slight growth in his cock and could feel it getting firmer. My ass is very tight (so I have been told), so I knew I would need to get him very hard. I must have sucked him for over ten minutes until he was rock hard again and getting antsy about getting some pussy.

I rose up from his cock and then I spun around so that I was facing the foot of the bed and gave a smile to the camera. I slipped off my dress but left on my bra, panties, thigh highs and heels. I applied a little KY to my asshole and lowered myself so that my ass was lining up with the tip of his nine inch dick. I held it in my hand and guided him into me. Slowly at first until I had the head of his cock inside me and then I crazy Cassie took over.

“Fuck me!” I screamed as I slammed my ass down and took the remaining eight inches in my ass.

“Fuck me!” I screamed again as went up and down on his tool.

I rode up and down ten or eleven times, as he held on to my hips with his huge hands. He was throwing me down on him as he thrust up meeting my plunges. My mind was blank, except for pure ecstasy as Ty fucked my man pussy.

“Ty, come fuck me harder.” I said as I pulled off and knelt sideways on the bed. He got behind me and shoved his cock inside me again.

He had all the leverage now and started shoving his cock deep in my ass. Over and over he continued to pound my ass. I knew he was going to last awhile, as he had already come once. I was almost blacking out at times as his big cock filled my ass so fully. I was on my knees, but now I collapsed on my hands allowing him a direct plunge. He pulled out his whole cock except for about one half inch and then got full leverage by pushing his body up to get a perfect angle. As he started to shove down, I pushed up to meet his powerful thrust. His cock went in so deep; I thought it was going to come out my stomach.

“Fuck, yes! Shove that big cock in me!” I screamed. “I want you cock give it to me!”

Ty was now really fucking me hard and fast. I was bucking as fast as I could to get the maximum penetration of his cock. I was going crazy, craving more and more cock. I don’t know how long he fucked me but it was at least fifteen minutes of hard ass fucking.

“Cassie, where do you want me to come?” Ty asked in an out of breath voice.

“Come all over me baby.” I replied. “Shoot all over my chest and face.”

“Ok baby turn around I am going to pull out.” He said.

I barely had a chance to spin around when the first shot of his cum hit me in the face. He shot more of his cum over my bra and bare stomach and I eagerly licked up the goo on my face and used my hand to sop up the cum on my stomach.

“You are some kind of good fuck baby.” Ty said.

“You got one great cock, Ty.” I replied.

It only took about five minutes for me to wash up Ty and for him to get dressed; he walked out the door around 1:15, a great 45 minutes or so of sex. I was totally fucked up from the martinis and feeling so sexy from my boy’s attention that I was on a great high.

I took off my clothes and took a shower to clean off the cum that Ty had left all over my body. I got out of the shower and put lotion all over my body. I brushed out my wig and reapplied all of my make-up. I hung up my dress and put my dirty bra and underwear away. It was close to 2 AM and I was hoping Barry was coming by for round 2. I slipped on a red lace lingerie number that was very sexy. It had two narrow straps on my shoulders and was a see through lace that held my small breast forms. It went down to about an inch above my belly button, where it ended with garter straps. I had on red lace panties with a sewn in gaffe.

I pulled out a pair of red silk stockings and pulled them up and attached them to the garters. I went to the closet and put on my red patent pumps with 4” heels. I stood up and looked in the mirror and I looked so sexy I wanted to fuck myself. I decided another martini was in order, but I was out of ice. I slipped on a black pea coat over my lingerie and walked down the hall towards the ice machine. I didn’t think I would see anyone in the hallway as it was 1:45 AM so I didn’t bother to button the coat I just left it open.

However as I was walking back a door opened down the hall and a man stepped out of his room and turned to my direction. He was wearing shorts and a t-shirt and was carrying his ice bucket. When he saw me his eyes became as big as oranges. I did not bother to cover up, just kept walking and when we were a few feet apart, I nodded to him and said good evening.

“Hey sexy, what’s going on?” He asked.

I looked at his shorts and could see he was already getting a hard on from just seeing me.

“It appears something is going on in your shorts.” I said. “Maybe I should do something about that?” As I placed my hand directly on his crotch. “Let’s go back to your room and let me take care of that for you.”

I grabbed his hand and let him back to his room. I set down my ice bucket and slipped off my coat as he shut the door. I reached over and slipped my hand inside his elastic waist band as he kissed me on the lips. I felt his tongue slide in my mouth and I eagerly sucked on his tongue as my hand found his cock. It felt like a nice six or seven inch cock and was already rock hard. I broke off the kiss and slid down to my knees as I pulled his shorts down to his ankle. I stroked his cock with my left hand and I lifted his balls up with my right. I started to lick underneath his balls and worked my tongue up the crack of his ass. He was leaning back against the door for leverage as I reamed his ass with my tongue. He started to moan as I stuck the tip of my tongue in his asshole and I could taste him with my mouth. Slowly I worked my tongue in and out of his ass and stroked his cock at the same time. He was moaning louder and was now sliding down the door to try and get my tongue further up his ass. I stopped my tongue action and let him slide down so he was sitting on the floor and I took my hand off of his long cock and I replaced it with my lips. I licked the tip of his cock like it was a lollipop then I licked the entire length of his shaft. He started to reach for my head to guide me on to his cock.

“Suck my cock you fuckin’ whore.” He said.

I obeyed his command and took the tip of his cock in my mouth and slowly slid my mouth down his delicious shaft. I went down very slow with my mouth wide open and then when I had his whole length in my mouth, I closed my lips around his base and rose up sucking on his cock the entire time I raised my mouth. Then I plunged down on his cock so that my lips were touching his balls and I stayed down until I heard a moan from the stranger.

He pushed down on the back of my head so that I could continue to hold the position of his cock buried in my mouth and throat. When he released me I started going up and down on his cock faster to create more friction. I tasted the first bits of pre-cum in my mouth and then the explosion started. A salty and fruity glob of cum hit the inside of my mouth and spread throughout my entire mouth. I gobbled up every drop and finally I sucked every drop of cum from him.

“Damn, that was a hell of a bj. Thank you.” He said.

“My pleasure!” I said as I licked my lips and stood up.

He also rose and I grabbed my coat and my ice bucket and went to the door. “I am in room 118, my last name is Finn, call me tomorrow if you are around.” I said as I walked out the door.

When I entered my room, my phone rang and it was Barry. He said he had to work late, so he would not be able to come by. I thanked him for all of his help and told him to call me tomorrow night as I would be having some people over, but there was always time for him.

My day was over, so I decided to have a good night cosmo. There is nothing like a martini chaser to a hot load of cum! Well tomorrow would be another day, and it is an even better story!

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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