Surprise at Girls Night Out
Cassie's Encounters in New Jersey
Surprise on Girls Night Out in New Jersey
I explained in an earlier story that my life took a strange turn when I turned forty. I had not been cross dressing for many years, but I had the urge again to bring out my alter ego and the urge was stronger than ever. I really prepared for Cassie, short for Cassandra (I also go by Sandy) by taking a year to buy all the things I needed and get into great shape so I could wear sexier outfits.
Sorry to all of you faithful readers that know all about me, but for those that are new here are the details. I am 5’9” tall and now weigh about 165 pounds. I have green eyes and pretty shapely legs. I am a straight male with no interest in men, but that all changes when I dress as Cassie. I become the cock craving slut, wild woman that I wish I could meet when I am dressed as a guy. Cassie loves to drink, in the old days I used to do drugs and smoke cigarettes, but over the past years I have stopped those vices, except for the drinking.
The past three or four months have been fantastic dressed as Cassie, I have had great experiences insuring that she is going to be around for a lot of years to come. I will share some more stories of my great experiences and look forward to telling you about the ones to come. However, this is a story of an experience that was different for me. I really try not to believe in coincidences, but after this experience, I changed my mind.
The internet is the greatest thing for all of us closet cross dressers (CD’s). We are able to connect with people like us and people that like us. In addition we can set up dates or arrange evenings out with our friends. My job results in me travelling extensively and this is where and when Cassie comes out to play. This particular experience took place during a trip to New York City where I had several business appointments over three days. That left the nights free and Cassie was going to have some fun.
I flew into Newark from the West Coast on a “red-eye” and arrived at 6 AM on a beautiful Tuesday summer morning. I grabbed my luggage and took a shuttle to my hotel in Secaucus, New Jersey. Secaucus is located across the river from New York City and I stay at hotels there sometimes because they are so much less expensive than staying in the city. Well, in this case there was another reason for staying there, which I will explain later.
My room was great for the same price that I would get a small box room in New York; I had a one bedroom suite in New Jersey. I spent a few hours sleeping in my room so I wouldn’t be tired for the whole day. In the afternoon, I did all my work for the day and was wrapped up around three. The hotel shuttle took me to a shopping center where I did some shopping (I always shop when I travel) for Cassie. I picked up a very sexy skirt, a camisole, a gold handbag and some gold necklaces and earrings. I also went into a costume store and bought a sexy outfit that I would only wear for indoor entertainment.
When I got back to my room it was 5:30 and started to get ready for my evening. My friend Julie (another CD) who I met on line and had partied with before was driving up from her home in Central New Jersey and going to meet me in my room at 7 PM. Around 9 PM we were going to meet some other CD’s at a bar they meet at regularly a few miles from the hotel. I mixed myself a drink, for those of you that are new to Cassie, a cosmopolitan martini is my drink of choice and stepped into the shower. After I dried off and applied lotion and powder to my body, I slurped the rest of my martini and started putting on my make-up.
I only put on a light amount as Julie was fabulous at make-up and she was going to put on the final touches. I slipped on my ivory 34B bra (with a pair of breast forms inside) and a pair of matching lace panties with a gaffe stitched in to hide my small penis and threw on a short black silk robe. My favorite wig was next, it is a beautiful jet black wig that goes about three inches below my shoulders and features long flowing curls at the end, otherwise perfectly straight with very subtle bangs in the front. I mixed another martini and Julie arrived before my first sip.
Julie is hot with a capital H. She is 32 years old and is about 5’ 6” tall; she was wearing her favorite hair; a blond wig that is very curly and long. She was carrying an overnight bag with all of her clothes on her left shoulder and a big tote bag in her right hand. We kissed at the door and I let her in watching her stroll across the living room in her short denim skirt and black tank top. I had never seen her wear anything other than high heels and today was no exception as she wore a pair of white patent stiletto heels pumps and a pair of white lacy ankle socks. Yes, she was a slut just like me and that is one reason we hit it off immediately.
“Well, are you pouring me a drink or not?” She asked sarcastically in her very feminine and sexy voice.
She loves cosmos too, so we are a pair to behold when we are out. Anyway, I won’t bore you with our conversations and catching up as we got ready together. Let me tell you about the evening ahead; tonight was girls’ night out at a bar inside a hotel a few miles away. This has been a meeting place on Tuesday nights for CD’s from New Jersey and surrounding areas for about a year and a half. I had gone on one occasion, the first time I met Julie in person.
For those of you who are not familiar with the CD community there is a wide variety of personalities and we each approach our dressing differently. When you attend an evening like the one we were going to, you would see all of those personalities and approaches represented. Some girls will be totally passable and some not at all, the majority somewhere in between. Some will dress very sexy, some very matronly, again the majority in between. Respect for all of us is my philosophy; some girls don’t have the time or money that I have had to make myself look more feminine, therefore I appreciate what they do to be able to express themselves.
Why I bring this up is that Julie and I were going to make a splash tonight. We were going to dress up very fancy and very sexy and some of the girls will resent us, but the majority would be fine. Usually about thirty of us showed up and there were always a couple of girls dress sexy and provocatively. Well by the time we were ready to leave at 9:00 Julie and I had finished off four martinis and were feeling very tipsy. Well, you have to kill the inhibitions off somehow!
Julie wore a strapless black dress featuring a silver chain halter that wrapped around her neck. It went down to almost her knees, but had a slit up the right side that almost went to her hip. She wore black fish net stockings and black patent pumps that had to be four or five inches tall. She wore silver accessories including bracelets, long dangling earrings and an ankle bracelet. She carried a black clutch handbag that matched her dress. I was in ivory from head to toe; my dress was asymmetrical featuring one strap that came over my left shoulder and it left my right shoulder completely bare. I wore ivory stockings that required a garter belt and they were made in a material that made them sparkle. My shoes were three inch ivory sandals that featured clear rhinestones matching the fake diamond necklace that hung between my breasts. My make-up was perfect thanks to Julie (as was hers) she wore pink lipstick and matching pink nails, while I went for red lipstick and nails including my toes which could be seen through my stockings with my sandals. I used all of my new gold jewelry and added a couple of bracelets I had packed.
We grabbed our light weight jackets and our handbags (mine was a little larger than Julie’s and featured ivory sequins) and stepped into our taxi waiting for us at the front door of the hotel. We turned a lot of heads strolling through the lobby and I thought, why are we going out, when we could get lucky here?
We arrived at the hotel and strolled through the lobby to the bar. It was a very good sized bar for a hotel and it featured a rectangular shaped bar with seats on all four sides. There was a small dance floor on the other side of the bar and a disc jockey played most evenings and always on Tuesdays. There were a mixture of people at the bar, but our friends were near the dance floor on the opposite side of the room. Julie and I took off our jackets and carried them as we walked across the room. Several of the other customers were checking us out as we walked by and I am sure that most of them were trying to figure out what the deal was with the unusual group of women hanging out near the dance floor.
Some of the customers knew about out meeting on Tuesdays, as they were regulars or had stayed at the hotel before on a Tuesday night. Other came because there were CD’s here and they wanted to be with us and then there were the customers who just happened to stop by for a drink and be in a bar with about 25 CD’s…these were the ones that were probably thinking…what is going on?
Julie and I said hello to our group and ordered drinks. Several girls were dancing together and a couple of guys were dancing with genetic girls (GG’s). I had to go to the bathroom, so I asked Julie if she needed to go and she agreed to join me. We walked back through the bar to the entrance and around the corner to the bathroom, before we walked in the door; Julie grabbed my hand and led me to a corner.
“Cassie, you are so fucking hot, why didn’t we just stay in the room and play with each other?” She asked before kissing me.
We wrapped our arms around each other and kissed deep and passionately. I felt her slide her hands under my dress and grab my ass and pull me closer forcing her against the wall. Our kiss must have lasted about thirty seconds and when we broke it off we turned around and literally bumped into a woman about 5’4” tall with red hair.
“Wow! You two were really going at it.” She said with a smile. She then licked her lips and said “I hope I see you two in the bar, we could have fun together.” She walked away towards the bar.
Julie and I both watched this little hottie walk away shaking her ass in her very tight jeans. I was in state of shock as I knew who she was. In all the many times I had gone out in public, I had never seen someone that I knew in my ordinary life. Her name was Sheila and she used to work for a company I worked for about three years ago. She was a store manager for an outlet store we had in Secaucus, and now she was in a bar obviously drunk and was flirting with Julie and I. When I told Julie, she laughed and she told me not to worry, she would never recognize me.
When we returned from the restroom, we passed by the table that Sheila was sitting and I winked at her and she smiled back. There were three guys and one girl at her table (some standing, some sitting) and she watched Julie and I all the way as we made it back to our group. I ordered another cosmo and while I was drinking and chatting with a t-girl named Irene an older man around 60 asked me to dance.
I agreed and we stepped on the dance floor now about three quarters full with a combination of couples. The song was a slow song by Rod Stewart and my companion was holding me tight and talking gently into my ear.
“What is your name darling?” He asked.
“Cassandra, but call me Cassie.” I replied. “How about you?”
His name was Dan and as soon as he said it, I realized I knew him also. What are the chances of me being 2,500 miles away from home and run into two people that I know in the same bar? Even stranger they both were hitting on me!
I knew Dan would not recognize me, as he was really drunk. He was pulling me very close to him and I could start to feel a subtle bulge in his crotch rubbing against me. Dan was a close friend of my brother who lived in Connecticut and I had met his whole family one time on a visit to see my brother. I figured this could be fun, so I decided to see where I could take this.
I pushed myself against him as we danced and whispered into Dan’s ear. “I like you Dan. Are you going to buy me a drink?” I asked.
“Sure baby, let’s go to the bar.” He said.
As we broke off the dance I casually brushed my hand against his crotch, so he wasn’t sure if it was intentional or accidental. We walked to the bar and sat about thirty feet from the group of girls, I winked at Julie and motioned her to join us.
“Do you mind if my friend Julie joins us?” I asked.
Dan didn’t mind at all and within a couple of minutes he had a blond on the stool to his right and a brunette on the stool to his left both slurping down fresh cosmos. We made small talk for awhile and ordered another round. He always had at least one hand on Julie’s or my thigh and we occasionally rubbed his thigh or gently held his arm when he made a joke or comment. We found out he was staying upstairs and this was his only night in town.
“So Dan, would you like to have a drink in your room with Julie and I?” I asked.
“Sure, let’s order one to go. Bartender, two more Grey Goose cosmos and one more Tanqueray and tonic.” Dan said.
We left the bar, but as I passed Sheila’s table I stopped and told her we would be back and asked if she would be here for a while. Confirming she would be there, I went back and joined Dan and Julie. We took the elevator to the seventh floor and I held Dan’s drink as he pulled out his key and opened the door. We walked into his very standard hotel room and Sheila sat down her drink and I sat down Dan’s and mine.
“Cassie, come help me touch up my face, okay?” Julie asked.
“Sure, honey.” I replied. “Dan we will be right out.”
We stepped into his bathroom and discussed our strategy. We decided to pretend we were hookers and would try to see how much he would spend to be with us. I thought it was a great idea. We both peed and fixed our make-up adding a fresh coat of lipstick. We slipped off our dresses and hung them on a hook on the back of the bathroom door. We were like total opposites, me in my ivory bra, panties, garter, stockings and shoes with black hair and Julie with the same items in black with blond hair. Since her heels were much higher than mine, we were almost the same height. We sprayed a splash of perfume on each other and we both slipped our breast forms (she wore small ones like me) into our handbags before we strolled out the door.
Dan was sitting at the desk in his room typing on a lap top when we came into the room. He turned and his eyes almost popped out of his head. We picked up our drinks, clinked our glasses together and then drank our cosmos in one big drink. We sat down the glasses and Dan walked up to us with a very noticeable bulge in his pants. He slipped his left arm around Julie’s waist and his right hand around mine and we took turns exchanging kisses with him. I knew he was closed to passing out, so we needed to hurry.
“How badly do you want us, baby?” Julie asked as she subtly rubbed her hand on his crotch one time.
“You girls are so hot; I want to fuck you so bad.” Dan said.
“Well how much will you give us?” I asked as it was my turn to rub his crotch.
“I guess I should have known you two were hookers.” He said as Julie started to kiss his neck and unbutton his shirt.
“Come on baby, let me play with you.” Julie said as I started guiding him to the bed.
Dan was a pretty big about 6’2” and weighed over 200 pounds, but looked younger than his age. He was handsome with straight salt and pepper hair, moustache and from the feel of it a nice sized pistol in his pants.
“Let me see how much I have in my wallet.” He said as he tried to pull it out of his rear pocket while being semi mauled by Julie and I. “How about $100?”
“Oh you can do better than that.” I said and started to undo his belt buckle, now that Julie had his shirt completely unbuttoned.
“Ok, $140.” He said when I had just pulled off his belt and we had guided him down onto the bed.
“That’s perfect!” Julie replied.
I stood up and turned off the lights leaving only the desk light on as Julie collected the money and put it into her purse. Julie slipped of Dan’s shirt while I slipped off his trousers and socks. All that was left were his boxers and we could already see a nice sized cock springing out of the fly of the boxers. Julie pulled them off and as I climbed on the bed and started to kiss Dan passionately. His tongue exploded into my mouth as he was incredibly horny as was I. I let him explore my mouth while I sucked on his tongue, he darted all over my mouth with his tongue and I could feel my body getting more and more aroused. I felt his hands behind my back and struggling to remove my bra. I reached around and snapped it off and let him peel it off me while we still were lip locked.
“I am sorry, I am so flat chested.” I said.
He didn’t seem to mind as I lowered my chest to his mouth he took my left nipple and sucked on it gently at first then harder and harder, nibbling on it and then using his hand to squeeze my chest and make my breast bigger so he could suck more of my tit. I moaned as Cassie has very sensitive breasts and the slightest attention turns me on so much.
I glanced over my left shoulder and I saw Julie licking the inside of Dan’s right thigh. She seemed to be going from thigh to thigh with tiny kisses and licks and when she switched legs she moved closer and closer to his crotch, which I could really see clearly for the first time. Dan had at least a seven inch cock with a beautiful purple head and a huge set of balls that looked to be filled with delicious cum.
It was very hard to do as it felt so good, but I pulled away from Dan’s attack on my chest to join Julie down below. She had just reached the top of his thigh when I brought my mouth to hers. We kissed each other on the lips; barely an inch from Dan’s swollen cock.
“That is so fuckin’ hot girls. You are two fuckin’ hot whores.” He said.
We broke off our kiss and I let Julie have first crack at his cock while I started on his balls. I lifted his bill sack and started licking the underside of his nuts. Julie started with a gently stroking of his shaft while I started sucking his balls one at a time very gently to insure it would not hurt at all. Julie started kissing the tip of his cock and slowly (with Dan pushing the back of her head) took the first inch of his cock inside her mouth.
“Yea, baby. That’s it suck my big cock!” He said.
Julie held the base of his shaft and was slightly stroking it as she started to slide her mouth down on his dick, ever so slowly. I was so hot watching her, I was ready to start playing with myself but instead I let go of his balls and grabbed a pillow from the top of the bed as Julie slipped in another inch of his cock into her mouth. I slid the pillow underneath Dan’s lower back to give some elevation to his mid level and as Julie took another inch of his cock in her mouth, I lifted his balls and started to work on his ass.
By the time I had started my first tongue probe of Dan’s ass crack, Julie had fully engulfed all seven inches of his cock in her mouth and he was getting more aroused. Thank goodness he had drank so much or I think he would have already shot his load, I know I would have. When I started licking his asshole and stuck my tongue tip inside his puckered ass he started bucking his waist resulting in him fucking Julie’s mouth while I tongue fucked his ass.
I didn’t want him to shoot his load before I had a chance for fun, so I motioned for Julie to kiss me. She gave him about six or seven up and down piston like sucks on his cock, taking the whole length of his cock then pulling off and then back down before removing her mouth and kissing me. I am sure she could taste the remains of the ream job I gave him in my mouth, while I could taste the juices of her mouth, his sweat and pre-cum in hers.
We never rehearsed anything like this, so after the kiss I whispered some directions to her and she winked in acknowledgement and understanding. Julie then rose up and placed a knee on each side of Dan’s stomach and unsnapped her bra. She lowered herself down so that her chest was in Dan’s face and he took the bait and started to attack her tits the way he attacked mine earlier. I heard Julie moaning in pleasure as I stepped off the bed and took of my panties. I removed some KY jelly from my bag and lubed my ass while opening a Trojan condom packet.
Dan was still rock hard when I slid the condom on his cock and I slid on the bed with my ass back to back with Julie’s.
“Dan, you got me so turned on, I want you to fuck me in the ass.” I said.
I held his cock in my left hand and lined it up with my lubed butt hole. I was so fucking hot; I couldn’t wait to have this big cock deep inside me. I struggled for about two seconds to get his huge purple head inside me, but as soon as he entered me, I knew I had to have him fully buried inside me. I held my cock and balls in my right hand against my stomach and Julie removed herself so he would have a full view of entering my ass.
“Fuck me baby.” I screamed.”Fuck me hard!”
Before I finished saying it I slid down his cock as hard and as fast as I could and everything in my world went blank. It was a high I can’t get enough of, the sensation of a cock deeply buried inside me! Thoughts ran through my brain in a millisecond. Pleasure, bliss, ecstasy…but a second later I was back in the present and needed that feeling again, so I rose up and slammed back down on him again. I can’t even remember what Dan was saying as I slammed up and down on his cock, but I knew I was in heaven fucking his brains out. I started feeling him trying to time my thrusts so he could meet me resulting in him going deeper inside me causing me to scream out in pleasure.
I couldn’t stop screaming. “Fuck me baby, fuck my fuckin’ ass. Fuck my ass with your fucking cock. Don’t stop fuck me. Fuck my ass!”
I saw Julie come to the foot of the bed and take my camera out of my handbag (now you see why I carried a bigger bag than her) and shoot a picture of me riding his cock.
“Fuck baby I am cumming!” Dan screamed.
I rode him even faster so that I could get every last thrust while he was still hard, but Julie motioned for me to get off. I slid off his cock and Julie ripped off the condom and went down on his cock with her mouth to drink up his cum. He shoved the back of Julie’s head down on his cock with his hands as he exploded into her mouth. Cum was coming out the side of her mouth, but I knew she got almost all of his juice. I had slipped my panties back on and Julie walked up and kissed me sharing a good part of his cum during our open mouthed kiss.
We then both gently went down on his cock taking turns slurping out the last drops of his big load enjoying every last drop of his man chowder. I wanted him again, but he was getting tired and already I could see he wanted to doze off. We kept him awake and were able to get him half hard with our constant sucking of his dick and Julie slipped a condom on him while I let him play with my tits again.
“Oh baby, I am so tired.” He said.
“Julie needs your cock too, baby.” I replied.
It took her a minute or so, but she was able to get his semi rigid cock inside her and I moved out of the way. Julie was facing him front wise and she was pivoting her hips side to side like she was using a hula hoop. I knew she was doing this to keep his cock inside her as he was not fully hard. Her balls were resting on his stomach and her thin five inch cock (about an inch longer than mine) was pretty hard. I grabbed my camera and started taking pictures. Then I switched to video mode and took some movies before Dan knew what was going on. I took off my panties and slid right beside Dan’s head who was trying to keep his eyes open.
“Dan, look at how hot she is.” I said. “Don’t you want to suck her cock?”
I pulled up his head and shoulders and put his right hand out so it touched Julie’s cock and then he woke up.
“What the fuck?” he asked as he pulled his hand away.
He tried to stop, but now that he was awake he was also enjoying the feeling of getting fucked. Julie was gyrating now even faster and I could tell she was enjoying the pleasure.
“Oh baby, you are getting harder, I can feel it. Come on fuck me baby.” She said.
Now she started grinding forward and back and Dan was now fully awake and starting the thrust back.
“That’s it, I can feel you, cum for me baby, cum hard in my ass pussy.” She moaned.
I was still filming the whole scene and capturing the beauty of Julie and the confusion and pleasure of Dan. I couldn’t take any more sitting on the sideline, so I slid down the bed lying on my side and took Julie’s cock in my mouth as she continued to shift forward and back on Dan’s cock. I was shocked but all of a sudden I felt Dan’s hand reach over and grab my hard cock and start to stroke my cock up and down. Now we were all getting attention and Julie was really starting to feel his cock get harder, because now she started riding his cock up and down. I was shocked to feel Dan’s hand continued to stroke my cock. He may have thought he was dreaming.
“That’s it, stallion. Fuck your whore, fuck her hard.” She said.
I slid Dan’s hand off my cock and I shifted position so that he and I were almost in a 69 position. However instead of sucking his cock I started back on Julie’s and let Dan take mine in his mouth. I don’t think he had ever done this before, but it sure felt good. We were starting to find a rhythm as Julie rode his cock in her tight ass up and down while Dan bucked his hips upward to maximize his cock inside her. I was timing my thrusts into Dan’s mouth with his thrusts and my mouth met Julie’s thrusts so that her cock was buried in my mouth. We were like a machine in perfect timing, until we heard the magic words from Julie.
“Oh God, Oh God. Cassie I am going to cum so hard.” She moaned.
I pulled my cock out of Dan’s mouth to give Julie my full attention.
“Fuck! I am cumming too!” Dan panted out.
“Ohhhhhhhhhh yes. Ohhhhhhhhhh yes!” Julie was screaming.
I felt her orgasm approach and I stroked the base of her cock to get a full load of her cum inside me. Dan exploded at the same time inside Julie’s ass and he moaned in pleasure. I knew I was about to cum, so as Julie hopped off of Dan I pulled her off the bed and had her stand spread eagle at the foot of the bed with her hands and upper body on the bed itself. I shoved my hard cock deep inside her and heard her scream in pleasure. We loved fucking each other and I wish I could last longer for her, but it only took me about ten powerful thrusts until I shot a full load of cum inside her.
She got off the bed and came to me and we held each other and kissed passionately. We looked at Dan who already looked asleep only two minutes after his orgasm. We went in his bathroom and cleaned up and got dressed. We picked up our things and then Julie pointed at the condom on Dan’s cock. I told her to turn the video on and I pulled it off and sucked his small load of cum out of it into my mouth. I am such a fucking cum whore!
I knelt beside Dan and said to him “Dan, do you have a tip for Julie and I?”
Julie looked into his wallet and he had at least another $200 in it.
She showed me the cash and I said “Dan do we get another $100 tip?”
“Yes, go ahead take it; I just want to go asleep. Take the money.” He said.
“Ok thanks!” I replied. “Oh be sure to say hi to Carrie your wife and your two daughters Lilly and Kelly.”
We were at the door by the time he realized what I said. We heard him open the door but by that time we were in the elevator. We laughed the entire ride down, but were fully content. Our strange encounter took only thirty minutes and now it was back downstairs to see if Sheila was still in the bar, but that is a wild story for another time.