I left the hotel feeling great. I got laid, got a job and made a new friend! I slipped on my ballets and placed my high heels in my bag to make my walk back easier. Like I said it was a short walk from my apartment to the hotel down Main Street, the major roadway in this suburb. My apartment was about ten short blocks away (just half a block from Main) and the ten blocks featured shops, restaurants and a couple other hotels. The street was pretty busy for a late afternoon with people walking and chatting while enjoying the beautiful warm spring day. I decided a cocktail was in order, so I stopped at a restaurant I was familiar with from previous visits. I changed into my high heels and walked in. The place I decided on (Big Jake BBQ) featured barbecue foods and other basics with a large bar that seated around twenty people.
The restaurant itself was not a sports bar, but kind of had that feeling with several televisions and a very casual environment. It would get crowded after five (from my experience) but at this time of day there were only three others at the bar and only about five of the twenty or so tables occupied. I ordered a Grey Goose martini with a splash of cranberry and a large glass of water. I slurped down the water and I could still taste a little cum residue that I swallowed earlier from Chris the hotel manager.
As I sipped my martini I started to drift off in my thoughts, remembering how I got to this place in my life. I was raised by a single mom with two older brothers. I was born Morgan Cassius Finn, and my middle name was the inspiration for the name Casandra. My oldest brother and my mom had passed away and my other brother was only in contact on rare occasions. I was raised in a small town in California and upon graduating high school, I moved to Arizona to attend college. That was where I first experimented with cross dressing, but never in public and only a few times in the privacy of my bedroom.
My financial situation forced me to work while in college and soon I had been promoted to a wholesale rep for a large company based in Tempe, where I rented an apartment. I had so much success that I quit college halfway through my junior year. Within five years I was a sales manager and bought my first home that I still own today.
When I was thirty, I married a woman two years younger than me, but our marriage split up after only a few years. She remarried and sadly passed away two years ago in a car accident. After my divorce, my life was pretty normal, lots of parties, nights out in bars, entertaining clients and always on the prowl for picking up women. On rare occasions, I would dress as Cassie, but I was not passable and did not make the effort to achieve that level. At forty, I moved back east to Connecticut for a great job opportunity, which until a few months ago provided me with lots of money and success. I bought a house twenty years ago in Connecticut and just put it on the market after moving to my current apartment a couple of days ago. My real estate agent believes I will almost quadruple my original investment.
In my previous job I traveled extensively, primarily domestically, and would stay in hotels. I would bring a suitcase of sexy women’s clothes, makeup and wigs and practice my crossdressing skills. The more I practiced, the more confident I grew. My collection of clothes, accessories, wigs and toys continued to grow. I started going out on walks and even went to stores just to be in public in the Cassandra persona. I became Cassandra on social media - Facebook, Flickr and “in the day” My Space.
I hooked up with a few other cross dressers and attended a couple of parties and that is when I got hooked. I was addicted to the feeling of dressing feminine and the power to make men cum. I started posting Craigs List personal ads asking for guys to come meet me in my hotel and let me suck their cocks. It got to the point that I enjoyed sucking guys and getting fucked as Cassie more than I did getting laid as Morgan, the guy. However, this addiction was taking over my life and I decided to concentrate on making enough money to be able to make this change a permanent reality. The change to being Cassie full time.
So, the last six or seven years, Cassie had been behind the scenes. Only once in a while would I dress up, primarily to practice my makeup skills and to determine which looks were best to pass as a girl. Between my investments in real estate, 401 K and retirement funds, I was set up for life and had the finances to go as far as to have the surgeries to become a female. In the short term I could start my transition which began yesterday by becoming her full time and tomorrow I had an appointment with a doctor I had conversed with to start the process with hopefully hormones and learning the timeline of a permanent change.
So, tomorrow was another big day; I had my doctor's appointment and I was also going to get my Massachusetts driver's license. I thought with my name as Morgan, it was a name that was OK for a man or a woman and I would have my picture taken in full Cassie mode and would help my process to make a full change to female. My plan was to live the spring and summer in my new apartment in Massachusetts and my fall and winter in my home in Arizona, which I recently had renovated and expanded to be an updated semi-luxury home.
Well enough with the boring details, I snapped back to the present and realized that my martini was empty. I ordered another drink and while it was being made, I went to the restroom. I still get a thrill using the Ladies' room, squatting in the stall and afterwards checking out my face and hair in the mirror. I did a slight touch up pulled down my skirt to be sure it covered the top of my stockings and returned to the bar. A more crowded bar now; I was so much in a day dream thinking of the past that I did not notice that the bar was seventy-five percent full.
I was minding my business almost done with my second cocktail when I noticed a man standing beside me. “Excuse me, I hope you didn’t notice me staring at you, but I have been watching you for about five minutes trying to figure out where I have met you before. Then, it came to me,” he said.
My eyes studied him for a minute, he was shorter than me and a little stocky, but I did not have a memory of him. He continued by saying that we hooked up over five years ago at a hotel down the street. He said he answered a Craig's List ad from a hot cross dresser that wanted a quickie in her hotel room. I knew this was bound to happen, (running into someone I fucked) - as I told you earlier, I was pretty slutty a few years ago and had countless hookups or quickies dressed as Cassie. He told me I looked even better now than I did a few years ago and offered to buy me a drink.
I could hardly refuse, so a fresh martini was delivered and he continued talking about our history. “I was telling the guys I was with and they did not believe me that you were a CD and that I hooked up with you. If you like you could join us.” He motioned to a high four-top table in the bar where three other guys were sitting and chatting while watching us.
“Well, I don’t want them to think you are a liar, so sure I will join you,” I replied.
We strolled over to the table together and one of the guys dragged over a fifth chair. I was introduced to them all. Marc was the one I had met before and the others were Julian, Brad and Patrick. All were about the same age; I would guess late forties and each had a different build and look to them. We started chatting about general things, but they made it clear that they were impressed by my appearance.
I was scoping out the situation, trying to figure out where this was going when Marc (sitting on my right) started pawing at my right leg with his left hand. Soon I felt another hand on my left thigh that belonged to Julian. I did not notice that Brad had gone to the bar and he returned with drinks, including another martini for me. As he gave me my drink, he slipped his arm around my waist from behind and whispered in my ear. “You are one hot girl. Marc was pretty lucky to hook up with you.” At this point I felt a brush between my legs and looked down to see that Patrick must have slipped off his shoe and was now rubbing the inside of my leg with his stocking-clad foot from across the table.
I looked at my watch and saw that it was nearing six. I had lost all my inhibitions due to the attention I was receiving and the almost empty fourth martini. “Well guys, how about we go back to my place for some quick fun, I am sure Marc remembers the rules. Quick fun for everyone and then off you go.” I slurred the last part of my sentence due to the cocktails.
It was a unanimous yes from the boys and I jotted down my address explaining that I would have to buzz them in when they arrived. I told them to give me a fifteen-minute head start. I slipped on my ballet flats and headed to the exit. I nearly ran home to get ready for the group. Upon arriving, I slipped on my white patent pumps and freshened up my face and hair. I brought out a box of condoms and a large tube of lubricant and placed them on one of the end tables that were on each side of my three-seat sofa. A few minutes later there was a knock on my front door as they must have been let in through security.
“Just a minute,” I called out. I placed a bottle of champagne on the coffee table and set out some glasses and strolled to the door. All four guys were there and I could tell they were anxious to come in and get started. They walked in single file and I sized up the posse that was in front of me.
As I said earlier Marc was short and a little stocky - about five foot eight with dirty blond hair and weighed about 180. Julian was the largest about six feet tall and was overweight probably around 240 pounds with black hair and a mustache and beard. Brad was tall and lanky and also had black hair and a beard. Lastly Patrick was a tall blond that weighed probably all of 150 pounds.
My heart started to race and I had to come up with a quick strategy on how to handle this situation. I told all of them to strip and sit on the sofa naked, except for Marc, who I directed to open the champagne and take the honors of pouring. “I hope none of you are driving,” I asked. Julian replied for all of them and said they were all from out of town except for Marc and that they planned on using Uber for the night.
I took off my black patent belt, took off my blouse and raised and rolled up my skirt so that it almost looked like a sash around my waist. I stood in front of the men in my matching white panties, bra and garter with my nude stockings and white patent shoes. My skirt was now bundled around me just above the top of my panties. Julian was the first one naked and he sat down in the middle of the couch with a semi-hard big cock that was calling my name. I knelt in front of him and immediately started licking his balls while stroking his huge cock that grew to at least eight inches. Patrick and Brad were now naked also and sported semi-hard dicks as well, each about six inches and not very thick. They flanked Julian on each side as I took Julian’s cock in my mouth. It tasted delicious as I sucked and licked it. I paused and looked into his eyes and then swallowed the entire length into my mouth and throat.
