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. 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 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 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.  

“Sit down Jorge, make yourself comfortable,” I told him motioning towards the couch.

He followed my directions and once he was seated, I went down on my knees in front of him.  I pulled down his jeans and saw his already semi hard cock in his white briefs. That cock needed to be set free and I was the one for the job. I pulled his briefs down to his ankles and slid up on the couch on all fours next to Jorge. He leaned over and pulled my face gently to his and kissed my lips while my right hand wrapped itself around his growing cock. The kiss was short but sensuous, but my mouth needed to be somewhere else.

I started stroking his cock gently, watching it grow and harden.  It was a big cock, around seven inches and not circumcised.  I peeled back the extra skin and started licking the delicate head making him squirm in his seat. I opened my mouth and started to swallow his hardened shaft using my tongue to lick his length and increase his pleasure.  I was so horny I could not wait any longer and slid my mouth down on his pole relaxing my throat and taking his whole length so that my nose was deep in his black pubic hair. Slowly I raised my head then lowering it, soon I was repeating this motion rapidly slurping noisily as I sucked his cock.  Jorge put both hands around my head and helped my piston like motions of sucking his cock. I felt a drop of liquid, probably pre-cum in my mouth and could feel the pressure of his cock getting ready to shoot.

“Here I come, Cassie…I am going to fill you up with my hot cum! “

True to his word his first squirt hit my throat and I eagerly swallowed it down as the next jet stream erupted.  My body was sizzling I was so turned on as my man kept jetting cum in my mouth.  It must have been days since his last orgasm as my mouth and throat were full of his man juice.  I kept swallowing and sucking until I had digested each and every drop of his fantastic cum. I licked my lips and sat up with a big smile on my face. 

“Wow, thank you, that was the best blow job ever!”  Jorge panted.

“You have my number anytime you want to stop by and get another one, just send me a text and if I am free… I am all yours,” I replied.

“Really?” he asked.

“Of course, I will be disappointed if you don’t take me up on it,” I replied.

Jorge left and I was in a great mood…only a few hours in my new life and I was filled with a full load!  Being in a mood to celebrate I poured a vodka martini (with a tiny splash of cranberry) and started unpacking my bedroom supplies.  My first box held my wigs and the forms to keep them in perfect condition.  I had four other wigs in addition to the one I was wearing. A short hair one in dark red/brown color, a dark red/brown shoulder length that I could style with bangs, an identical blonde version of that one and a very long black hair wig that went half way down my back.  I placed them on their forms and lined them up on a shelf in my walk-in closet.  I finished organizing my second suitcase of clothes and accessories when I realized it was 6:30 and the only thing I ate since breakfast was the glorious man chowder from Jorge.

The main reason I chose my new location was due to my familiarity with the area.  My old company was located about two miles from my new apartment and I spent many nights in local hotels and knew all the restaurants, bars and shopping areas.  Therefore, I knew the perfect place to call and have my dinner delivered.  I called my favorite restaurant for salads and ordered a salad with seared scallops and an order of fries. 

While waiting for dinner, I completed my unpacking the last suitcase and changed into a short red nightgown with red panties and no bra.  I covered up with a matching silk mid-thigh length robe. I slipped on my fun slippers that were really low heel slides with red pom-pom on the clear vinyl upper.  It felt good to be all moved in and I made a second martini to sip. 

Then I went into my “toy” drawer and pulled out my medium sized butt plug.  I knew that I would be pleasuring myself in bed tonight and I wanted to be all stretched out for my big eight-inch vibrating dildo.  I slid a little lube on my plug and some on my asshole and then slid my plug in all the way to the hilt.  My cock immediately started to rise and I tried to relax so that my manhood would not be seen through my panties.  Although I was not well hung (about 4” when hard) it was big enough to show if not tucked away carefully in a gaffe or slid up behind me.  Soon I was tucked away and sashaying through my place to keep my butt plug snug in my behind. 

I heard a knock on the door and thought it must be my dinner delivery (someone must have let him in at the security entrance).  I went to the door and saw a young man that couldn’t be more than eighteen or nineteen years old. Dressed in sweatshirt and sweatpants and a black beanie hat, he was a very cute young boy! I invited him in and told him to put the bag on the dining room table while I got my money.  The total was $24.00, and I pulled some cash out of my purse.  As I was doing this, I was trying to give him a little pose of the back of my legs and ass by stretching on my tippy toes to reach my handbag.  As I turned around, I caught him trying to take a picture of my backside.  I walked up to him and gave him $30 and came so close to him he had to back against the table.

“So, you want a picture of me?”  I asked.  “Don’t deny it.”

I could tell he was embarrassed, but I did notice slight tent growing in his sweat pants.  “Well, I will let you take a picture, but it will be the picture I want you to take. Now pull down those sweat pants.”

He didn’t say a word but he nervously slid down his sweat pants and to my surprise he had no underwear on and his mildly erect dick appeared.  It wasn’t very big; I imagine about five inches but it still looked delicious.  I grabbed his cock gently and stroked it a couple of times and it was getting very hard.

“Now listen to me, I want you to face fuck me with that cock of yours and tell me before you cum,” I ordered.

“Yes lady, I will do it,” was all he could say.

I went down on my knees and took ahold of his cock with my mouth and sucked on his swollen member.  I reached around and grabbed his ass and pulled him into me.  He started gyrating his hips and shoving his cock down my mouth and throat.  It felt wonderful taking this young man’s dick in my mouth and was now able to feel his balls slapping me underneath my chin. It couldn’t have been more than two minutes when he said, “I’m cumming!”

I stopped sucking and pulled back. “Shoot it all over my face, cover my face with your cum.” 

I closed my eyes and opened my mouth and felt hot jizz hitting my face on my nose, closed eyes, cheek and even in my mouth.  He kept spurting out cum and I felt my whole face must be covered.  Then I opened my eyes and told him to take a picture of my face covered in his white goo.  He quickly picked up his phone and started taking pictures.

I stood up and slurped up as much cum as I could with my tongue and then wiped more up with my fingers and licked it off. Then I went back down and sucked all the rest of his juice out of his cock.

“Now you have a picture of your dirty cum bag customer. You can show it to your friends and brag about this cock sucking slut who loves to take your juice all over her face.”

I stood back up and kissed him on the cheek as he pulled up his pants.  “Thank you, that was great,” he told me as he left.  I went to the bathroom and washed up. I took all my make up off (and the residual cum) as well as picking some cum out of my hair.  “What a fucking slut you are, Cassie!” I said to my reflection in the mirror.  I put a light powder coat on my face to keep my face a little feminine…with this little amount of make-up I am certainly passable in dim lighting, with a little lipstick and rouge, I would be fine in almost any lighting and since I was alone, I did not need the lipstick and rouge.

Dinner was calling and so was the rest of my martini.  I ate dinner while browsing e-mail and websites on my lap top.  After cleaning up and rearranging a few items around the apartment I thought it was time for bed, after all it had been a long but wonderful day.  I looked at my watch and saw it was 9:30, so I went to the bathroom and was preparing to take off my breast forms when my phone buzzed. I picked up my phone to see who was texting me. 

I read the message. “Hi Cassie, it’s Jorge.  If you are still up, I would love to come by, I can be there in 30 minutes.”

Oh Boy!  What a day!