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.