My first full day of my new life was fabulous and day two has started out with a bang.  A morning run sandwiched by blow jobs to two different men was the best way to start a new day.  I was savoring the memory of sucking off the security guard Greg and looking forward to the rest of my day.  It was still early but I could tell from the morning sun it was going to be a very warm day in Boston.  I decided to take a quick rinse off in the shower and go up to the rooftop pool to rest in the sun and enhance my tan. 

I finished my shower and slipped into my swimwear.  I chose a black two-piece bikini with bright polka dots for the morning sun.  I wrapped a white sarong around my waist and packed a tote bag with some suntan oil, a magazine, a beach towel, my cell phone and a snack.  Black flip-flops and my oversized tortoiseshell sunglasses completed the look.  I made myself a tall vodka and orange juice to sip, as I am a big believer in day drinking.  I left the apartment and took the one flight of stairs to the rooftop.

The pool was not large but it had a large sundeck complete with lounge chairs and patio tables with umbrellas and chairs.  The gym was also on the roof adjacent to the pool.  You could see inside the gym as it featured floor to ceiling glass panels to allow workout warriors a clear view of the pool. Next to the gym was a sauna, which I planned to use some mornings to sweat out the toxins from any late-night bar adventures.

There was no one in the gym and only one couple sitting by the pool. They were sitting at one of the patio tables and they looked up and said hello to me as I sauntered over to a lounge chair about ten feet from them.  I laid out my towel, removed my sarong and got settled into my chair.  It felt glorious just lying in the sun in my bikini; I felt like a real woman!  I could hear the conversation between the couple next to me and discovered the woman was leaving to run errands and wouldn’t be back until after noon.  As I rubbed my tanning oil over my legs, stomach and parts of my back (the parts I could reach), I noticed the man stealing glances at my tan body laid out on the lounge chair.  My top showed off the full breasts as my forms looked as natural as a real set of tits.

I rolled over on my stomach and noticed if I turned away facing the opposite direction of the couple, I could see them clearly through the reflection in the windows of the gym.  When I completed my change in position, I noticed the woman leaving the table and walking towards the stairs, obviously leaving to do her morning errands.  This left the gentleman by himself and gave him the opportunity to openly stare at my backside.  He was clearly enjoying himself as he was staring and appeared to be rubbing his crotch as he was eyeing my form.  I spread my legs a little further apart enhancing the view of my legs and inner thighs which must have been to his enjoyment as he increased his crotch massage.  Once I was sure he had to be getting hard I slowly sat up and picked up the drink off the table next to my lounge chair.  I took a big swig of the potent screwdriver and stood up and approached him.

“How rude of me not to introduce myself; my name is Cassie,” I said as I offered him my hand.

I was standing only a few inches from him and could clearly see his hardened cock through his swimsuit.

“Ralph, Ralph Wilson is my name,” he spoke.

“Well Ralph, are you enjoying the scenery?” I asked as I shook his hand. “It appears you are.”

I looked directly down at his crotch, bent over and placed my hand right on the lump in his swimsuit. 

Ralph appeared to be around my age with greyish hair.  He had on a white tank top that read St. Petersburg Beach, red swimming trunks and sandals.  As I removed my hand and rose, he stood and towered over me; he was at least six feet four inches tall and very thin. 

He took the drink from my hand and put it on his table.  Then he extended his arms and wrapped them around me, placing both his hands on my ass cheeks and pulled me close to him. His body pressed against mine I could feel his hard cock pressing into my stomach as he lowered his head and whispered into my ear.  “You like the feel of my big hard cock, Cassie?” 

I slid out of his grip and made a 180-degree turn bent over at the waist and raised my ass so it pressed right into his loins.  “I would like to feel it up my ass, Ralph.”

“Let’s go to the sauna and you can have all nine inches in your sexy ass,” he spoke.

I stood up and walked to my chair grabbing the tanning oil as he followed me to the sauna. It was a short walk and soon we were inside and the door locked.  Ralph took me in his arms and pressed his lips on mine. His tongue immediately shot into my open mouth and he explored my tongue with his as he grabbed my left tit with his right hand.  We broke off the kiss and I knelt before him and I took off his swimming trunks.  The sauna was dimly lit but I could clearly see his monster cock rock hard in front of me. I squeezed out some oil from my bottle into my hands and then I massaged his cock with both hands lubricating it thoroughly.  It seemed to grow even longer and I think his nine-inch statement was quite accurate.

I turned around and placed my hands on the bench pulling down the bottom of my bikini being careful not to show him any of my balls and dick.  A girl becomes an expert at this move with so much experience.  I felt his hard dick almost immediately start to grind into my tight asshole and his circular movements of his big cock started to break the barrier and I felt the tip start to slide in. 

“I knew you were a cock slut the minute you walked out to the pool.  You little fucking slut, I am going to fuck your ass, but first you better beg for it,” he said.

“Fuck you Ralph, you want this ass, so bad…now fuck me!” I answered.

He pushed a little harder and with a loud pop I felt his head enter my ass. “You like that you little cunt? You want me to fuck your tight ass with my big cock?”

“Yes, baby.  Fuck me hard and fast,” I begged.

He grabbed my waist with his hands and thrust deeper into me.  His big cock spread my ass wide open and I moaned in pleasure as I felt his hot cock fill my love canal. “Yes baby, give me that cock, shove it all in!” I screamed.

Again, he thrust his hips and now his dick was at least halfway in and going deeper.  He pulled back and then shoved even harder and his cock went deeper yet.  I waited for his next thrust and I bucked my hips and thrust back at him to get him deeper inside me. The timing of my thrust was perfect as it met his thrust and his whole cock went firing inside me as I felt his groin hit my ass cheeks. He continued his assault on my ass slamming his huge cock inside my ass over and over. 

Deeper and deeper he went, sending my pleasure to new heights.  He was grunting as he slammed his cock in, like a pile driver filling me up.  The sounds of his grunts, my screams of pleasure and his waist slapping into my ass made for a spectacle of noises suitable for the best porn video. Without warning he groaned even louder as his cock erupted inside me, filling me with a sense of warmth from his hot cum. The release of his first shot did not slow Ralph down as he continued to slam me with his cock and more juice shot deep inside me.  He slowed down his pumping and came to a stop with his long cock still inside me.

“Fuck, that was hot!” he muttered. “I love a surprise like that.”

He slowly withdrew his cock and I quickly pulled up my bikini bottoms and tucked my semi-hard penis out of sight.

“You made my morning special, Ralph,” I replied.

We exchanged very few other words as he pulled up his shorts and I unlocked the door and we stepped outside.  He told me he was going to get cleaned up before his wife returned and we agreed that we would try to hook up discretely again in the near future. I returned to the pool and relaxed on my back, enjoying the sun and feeling a small amount of Ralph’s cum oozing out of my ass into my bikini. 

I must have dozed off in the sun as I woke up in a daze in the warm sunshine. I was still alone at the pool and gathered my thoughts for the rest of the day.  It was a little after noon and I had a meeting scheduled for 3:00 PM.  My meeting was actually an interview that I set up about three weeks ago while I was working at the office of my former company.  As I mentioned earlier, I used to visit this area frequently when visiting the home office for meetings.  On my visit three weeks ago, I spoke to the manager of the hotel I was staying at about a part-time job in the future once I relocated permanently to the area. I disclosed my plans of transitioning into a woman and told him that I was hoping to find part-time work to help meet people and to get myself into a social environment.

We spoke about fifteen minutes and I outlined to him my plans of moving and starting the process of taking hormones to enhance my change.  He was candid also saying he was concerned about my appearance and if it would be uncomfortable for his customers and staff if I truly did not look like a real woman.  I told him we should set up a time for me to come back and I would convince him it would not be a problem.  Now that meeting was less than three hours away and I had to prepare my appearance for the interview.

After eating my snack and relaxing for another thirty minutes in the sun, I gathered my things and returned to my apartment.  I stripped out of my bikini and sarong and rinsed out the bikini bottoms that now had a good amount of dried cum in the crotch.  I put a load of delicates in the washing machine as I had built up a good number of soiled panties, sleepwear and my bikini from all of my sexual escapades of the past twenty-four hours.

I ate a small lunch while my clothes were washed and also laid out my outfit for my interview.  I wanted to wear an outfit that was similar to the uniforms worn at the hotel by the staff, but I wanted to make the outfit as sexy as possible, while making it somewhat professional.  I chose a white, long sleeve, button-up blouse, a short black stretch skirt, black patent wide belt and black patent pumps with three-inch heels. Then I chose a matching white bra and panties (my white thong gaffe), a white lacy garter belt and sheer nude stockings.  I went with all gold jewelry, bracelets, necklace and rings.  

I retrieved my long black hair wig that reached halfway down my back and I brushed out the wig and laid it on my bed next to my clothes and accessories.  I gave myself another enema to be fully clean and then stepped into the shower and scrubbed my body clean.  A thorough lotion application and a long makeup session followed my shower.  I slipped on my outfit leaving the top three buttons of my blouse undone to give a full look at my cleavage. I admired myself in the mirror, thinking that I looked ten or fifteen years younger than my true age of sixty. Oh, and yes, I looked like a real woman! I decided to wear my ballet flats and put my heels in my bag and would change just before my arrival at the hotel. 

I left my apartment at 2:45 and made the ten-minute walk to the hotel.  Just before entering, I slipped on my heels and strode inside the entrance with a lot of confidence, but a slight touch of nervousness.  I approached the front desk and met the woman behind the front desk.  She introduced herself as Jodie, and I told her I was Cassie. She was a woman about forty-five years old with blonde shoulder-length hair.  She was also wearing a white button-up blouse but hers had the logo of the hotel above her left breast.  She had nice breasts, not large, probably a 34B and firm.  She was very tan and looked more like she was from Dallas than Boston.   She told me Chris was expecting me and that she would take me to his office, which turned out to be behind the front desk.  As I walked into the office, I saw the look of shock on Chris as he obviously did not expect me to look like this.  I stopped about two feet in front of his desk in the small office and did a slow spin to show off my whole body. 

“That can’t be you…I mean, oh my God, you look amazing,” he said.

“Hi, Chris.  Let me introduce myself, I am Cassandra, but you can call me Cassie,” I offered.

For about two minutes he kept rambling on and on about how I looked and that he would never have recognized me.  He told me that I was hired for the position of part-time desk clerk.  I would work Tuesday, Thursday and Friday from noon to five in the afternoon.  On Friday I would be working with Jodie, but the other days I would be on my own.  She had the same shift as me on Monday, Wednesday and Friday. He mentioned that he had done research and that his company was thrilled if I would be hired as it would help them with their hiring practices, as I would be considered trans-gendered.  I would start Friday, so I could learn the ropes with Jodie.  He discussed details on some general procedures including dress code, punctuality, customer service and basic requirements.  Once he was done, he asked my size for tops as they would provide two blouses and two polo-type shirts for me.

He left the office to retrieve the uniform pieces and I couldn’t resist trying to seduce him for a quickie.  I knew he loved to pick up girls as I had watched him in the past when staying at the hotel, flirting with women.  I unbuttoned another button of my blouse to leave almost my whole bra exposed and also pulled up my skirt so that it left the top of my stockings and bottom of the garter belt exposed as well.

He returned shortly and when he entered his office, I spun my chair around to show off my wardrobe adjustments. I unbuttoned another button of the blouse as he closed the door to his office behind him and I spoke. “Do you want me to try those on now?”

Before he could answer, I slipped off my belt and skirt and finished unbuttoning my blouse.  He stepped forward and put both his hands on my tits and squeezed gently.  “Wow those feel real, and you are so fucking hot.”

I rubbed his crotch as he felt my tits and started unbuckling his belt with my other hand.  Within a minute I had his pants and underwear around his ankles and had my tongue on his hardening cock.  I stroked the base of his shaft as I slid my mouth around his hard dick.  He was hung very well — a wide seven-inch dick — and I savored it as I took his full length in my mouth and into my throat. I stretched my mouth as wide as I could to fully encapsulate it in my mouth.  I spent three minutes sucking and slurping his cock as my saliva drooled out my mouth leaving a trail from his cock head to my lips as I pulled my mouth away. 

Reaching in my purse, I grabbed some lube and spread it across his cock and then slipped some in my ass as I pulled my thong to the side.  I placed my hands flat on his desk as I turned around and stuck my butt out towards him. He moved closer to me and aimed his cock at my butt hole and grabbed my waist to gather leverage.  Chris's wide cock took about two minutes to finally break through and enter me.  I wanted to scream out in pleasure as I felt him enter me, but I restrained myself to not make noises. 

He must also have been trying to keep our sounds to a minimum, as he slowly pushed forward to guide his cock deeper inside me.  I gently thrust back to help him get deeper penetration and I felt him successfully get inside me inch by inch.  His gentle force made my pleasure gradually increase as did his speed of shoving his cock deeper.  On his next push his dick was fully buried inside me and he held that position as I turned and looked over my shoulder. 

Chris had his eyes closed as his hips were pressed against the cheeks of my ass with his rod completely encapsulated in my man-pussy. “Oh baby, your hot cock feels so good,” I whispered. “Fuck me slow, keep fucking me.”

He pulled his dick about halfway out and then gave a gentle shove forward to fully enter me again.  He repeated this about five or six times, gradually gaining speed.  We fell into a perfect rhythm of his pushing forward and me backward so that our fuck was giving us maximum pleasure and depth. I started to moan quietly and felt my pleasure reach new levels. 

“I am going to cum, Cassie, where do you want it?” he quietly uttered.

“Let me taste you, let me swallow that big load of yours,” I replied.

He gently withdrew from my clean ass and I pushed with my hands to stand up and then I turned around and went to my knees.  I grabbed his thick rod with both hands and guided it to my eager mouth.  Again, I stretched my mouth as wide open as possible to be able to handle his wide cock and wrapped my lips around the swollen head of his dick.  Stroking the base of his cock, I only needed about thirty seconds of slurping his dick until the first jet of hot cum shot out of his cock into my mouth.  I slurped and swallowed as the second and then third shot of his man-juice escaped his dick.  I continued to stroke and suck on his cock to get every last ounce of his cum and eagerly swallowed every drop.

I won’t bore you with our follow-up conversation and clean-up, but it was only a couple minutes later that he escorted me out of his office and welcomed me as our newest employee.  I strolled out to the front desk and stopped to talk to Jodie. 

“Well, look at you Cassie!  You have a glow to you; I hope Chris treated you OK,” she said with a wink.

“It was the most fun interview I ever had. He said we would be working together, hope you like to have fun too!” I countered.

“He can be fun; I think we might just get along famously,” Jodie said.

We exchanged phone numbers and planned to get together after her shift on Thursday for drinks.  I guess I am going to have my first girls' night out! 

To be continued....