Cassandra’s New Life Chapter 6

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Hi my name is Cassandra, but everyone calls me Cassie…well at least when I am dressed as a woman.  Yes, I am a cross dresser and have been doing it on and off for thirty years.  I wanted to share my latest adventures that started to unfold on my sixtieth birthday.  I have had some wild adventures over the last thirty years, but have kept Cassie in the closet the five years before my big birthday.  I wanted to focus on other things as Cassie can be quite a distraction to my everyday life.  I really wanted to be Cassie full time and one of the positive effects of the pandemic, is it allowed me to retire from work with a big severance package and pursue what I really wanted.I have kept myself in shape as I got older through exercise and diet.  I am about 5’9” tall and weigh about 150 pounds.  Not svelte but a body that can definitely pass as a female.  Despite not dressing very often the past five years, I have maintained all of Cassie’s possessions (clothing, jewelry, etc.) and have added to my collection substantially.  I also made some changes to my body over the years including laser treatments to my whole body to eliminate 90% of any hair growth on my legs, chest, stomach, underarms and the private areas.  I have let my nails grow to make my hands look feminine and have had regular manicures and pedicures to make them shine. I stay tan all year round from sun bathing and tanning beds.I packed all of my feminine possessions into over ten cartons, three large suitcases and two wardrobe boxes from U-Haul.  I lined all the cartons with large plastic bags to make unpacking easier.  Over three days I loaded everything in my new minivan to prepare for my trip.  On a beautiful late spring day around 8 AM I left my home in Connecticut and headed to an apartment I rented in a suburb west of Boston.  It was a four-hour car drive to the place where my full-time life of Cassie would exist.  I dressed for my ride in a conservative but a little sexy outfit.  I chose a pink sweater (showing off my nice shaped breasts created with my expensive 34C breast forms that match my skin tone perfectly) with stretch khaki pants and a pair of ballets. isvecbahis I had a short black leather jacket featuring several silver zippers for ornamentation and wore silver bracelets, necklaces and earrings in my recently pierced ears.  I wore my short black hair wig, mascara and false eyelashes.  My last addition was a coating of bright red lipstick (matching the color of my nails) and a coat of lip gloss to complete the look.At sixty years old, I am not going to have all the guys stare at me, but I have found over the years, that almost all guys will try and pick you up if you give them the chance. I avoided the early morning traffic by taking some side roads and entered the freeway heading north. I got a few smiles from men in cars passing me and I delightfully smiled back. About half way to my destination I stopped to go to the rest room and get a fresh hot cup of coffee.  I pulled off the freeway to a busy road side rest area featuring lots of trucks and passenger cars.  After using the ladies rest room, I purchased my coffee and strolled toward the door to leave and a truck driver exiting at the same time held the door open for me.  I thanked him and gave him a big smile and as I walked towards my car, I gave him a good look at my wiggling ass as I walked ahead of him.  He quickly caught up to me and smiled. “You are a very attractive woman,” he commented.“Well thank you, what a nice thing to hear from a handsome man,” I replied. He did have a handsome face, very masculine.  He was about 6’2” with a day’s worth of growth on his face.  Maybe a little overweight, but he looked good in his tight jeans and white t-shirt with a denim jacket and work boots.  I decided to be a little more friendly and asked him, “Do you ever spend the night around Boston?  Because I would love to go out for a drink sometime.”He smiled and said he would be soon and would love to hook up.   We exchanged numbers and at that time I was beside my vehicle.  “OK, I look forward to it.”I felt like a school girl as I was so excited as I got back in my car, hoping I would have a date soon.  I was starting to get the itch to be a nasty girl again, hoping isveçbahis giriş to get a hard cock in my mouth soon!   But that was going to have to wait; I wanted to get to my new apartment and start moving in.  I had a guy that I hired through Craigslist to help with my unloading and unpacking and he was supposed to meet me at my place at 1:00 PM. I pulled into my new home around 12:30 and brought my overnight bag and handbag with me to the elevator.  My new place was on the top level (third floor) and as I exited the elevator it was a short walk to my new place.  I opened the door and I was so happy, it looked even nicer than when I rented it a couple of weeks ago.  It was a spacious two-bedroom apartment featuring a nice sized kitchen, a combination dining room/living room and a great balcony that held two chairs and a small table.  It was fully furnished including the master bedroom and guest bedroom.  The first stop was the bathroom to touch up my make-up and unpack the toiletries I had in my overnight bag.  I dropped my bag on my queen size bed and then I went to the kitchen and drank the rest of my bottled water I had for my trip.  My intercom rang and my helper announced his arrival; I buzzed him in and waited for him to arrive.Jorge (he pronounced as George) arrived soon thereafter.  I had only talked to him on the phone, so it was our first meeting in person.  He was a young Latino man about 5’ 10” with a build that showed he did a lot of manual labor or working out.  He was wearing a grey sweatshirt and faded blue jeans.  His skin was a bronze color and his face was narrow and featured a goatee and mustache. “You must be Jorge, so nice to meet you.” I offered my hand.  He gently shook my hand.  “Thank you for the job, Miss Cassie, where do I start?”I had a plan in place for him to unload my van and bring everything up to my apartment.  The office at the complex had a cart we could use for transporting and after me showing him my van and giving him a key for access, he started working immediately.  I told him it should be about four hours of work and we should be done by 5PM.  As he was unloading, I was planning isveçbahis yeni giriş a trip to the grocery store to stock my shelves.  As soon as he got everything out of the van, I took off to go shopping. It was about 2:30 when I returned and Jorge had made great progress.  He had all the boxes in the appropriate rooms and had unpacked my wardrobe cartons and hung all my clothes in the spacious walk-in closet in the master bedroom.  We spent the next hour unpacking and worked up a sweat.  Jorge had ditched the sweatshirt and was now wearing a blue tank top that showed great biceps.  I told him I was going to change while he finished unpacking the balance of my kitchen items. I slipped out of my clothes and put on a white sports bra and a pair of light blue running shorts with a pair of white sneakers. Since the kitchen and bathrooms were done, I asked Jorge to help me with my living room items.  It was only two boxes of decorations and entertainment items like CDs and DVDs.  I spent a lot of time bending over letting my shorts creep up my legs hoping Jorge would enjoy seeing my legs and the bottom of my ass.  Indeed, I caught him a couple of time stealing a peak as I bent over and also as he looked at my breasts filling out the sports bra. When the last box was done, I told him we were done for the day; all that was left was my clothes and personal items in the bedroom, which I planned to do myself.  I asked him if he would like a cold beer and he was thrilled as he had worked up quite a sweat.  We opened a pair of Coronas and I invited him out on the patio to enjoy them.  Looking over the riverwalk behind my apartment complex, we chatted about little things and I kept putting my hand on his knee to gauge his reactions.  When our beers were done, we stepped back inside and I gave him $150 for his work (about $50 more than we agreed). “Thanks, Cassie, that is very generous.” he said.“You are welcome!  I would love to give you something else as a tip,” I replied with a mischievous grin.I reached out to him with both arms and placed my hands on his hips. I pulled myself closer and gently slid my hands across his waistband so my fingers were wrapped around his belt. Feeling courageous and finding no resistance from him I started to unbuckle his belt and looked up into his eyes.  He smiled as I started unbuttoning his jeans and I pulled down his zipper.  

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