Vacation of Life

By Paula

Published on Aug 2, 2007

Transgender

I woke up later in bed alone when Rosa called to me. "Senorita" I opened my eyes and looked at her. She was very pretty and was smiling at me. "Senorita, Tony wants you to meet him out at the pool for breakfast in a half an hour." I said OK thank you Rosa and rolled over on my back. She winked at me and blew me a kiss as she left. I through the covers of me and went to get out of bed when I realized how sore I was. My muscles ached all over from all the sex last night. My ass was very tender too but somehow felt good. So that what girls felt like when they were fucked real good. If it was I liked it. I stood up and began to stretch to loosen up and when I stretched my legs in a semi split position Tony's cum ran out of my ass and down my leg. I decided it might be a better idea to stretch in the shower. I went to the bathroom and started the shower and brushed my teeth while the water got hot. I stepped in and the hot water felt good on my aching body. I stretched a little but was short on time so I took care of the important stuff. I washed my body and my hair. Now I know why girls bitch about having long hair. It takes forever to wash. I used a douche to clean my pussy and my sensitive ass and jumped out of the shower so thankful I didn't have spend any time shaving. I toweled off and brushed my hair out, sprayed myself with perfume and went to the closet to find a bating suit. There were several but I choose a solid black bikini. I put it on and was again amazed at how beautiful I was. The top was very skimpy and covered my nipples but my breasts hung out both sides. The bottom was a thong that made my ass look great. I put on a pair of black open toed sandals with a 4" heel and threw a black sheer robe on and headed out the door. I went down the stairs and smiled as I thought about how comfortable I was in the heels and being a girl. I walked to the back of the house and through the sun room which opened to the pool. Tony was sitting at a table reading the paper and watching the news on a flat screen TV. I went up to him and said "Good morning handsome" and kissed him on the cheek. "Did you sleep well Danielle?" "Yes I slept like a log. Thank you for a wonderful night. You were amazing." "You were wonderful too. You are a natural." I just smiled at his compliment. Rosa came walking in with a tray of food. There was a little of everything. Lots of fruit, biscuits and gravy, pancakes, eggs, bacon, sausage, coffee, juice and milk. "Help yourself" Tony said. Rosa handed Tony a cup of coffee and set plates and silverware in front of us both. "Coffee Senorita?" "Yes please." She poured me a cup and put the sugar and cream in front of me. "Will there be anything else sir." Rosa said. "No Rosa. Thank you." Rosa left and Tony put his paper down and surveyed the tray of food. He started serving himself some generous portions of everything and told me that we will have breakfast and then talk some business and then take a dip in the pool. He was very business like this morning and I was a little offended after the passion we shared last night but said nothing about it. I helped myself to eggs, bacon and some biscuits and gravy and milk. After breakfast Tony told me that I was into him for about $50,000.00 and that I would earn $1000.00 a day for each day I spent as his girl and there would be other ways I would earn the rest of the money. He explained that I would do some escort work for him but only with very rich powerful men who would wine and dine me and treat me like a queen. I frowned a little at the idea of being whored out and he warned me not to cross him because he could and would make my life miserable. I just nodded as he continued. He said he would be out of town the next couple of days and Rikki would be looking after me. I fought the urge to jump up and down but was beaming inside at the thought of being with Rikki. "You have my permission to please Rikki in any way like you did with me." I smiled big and said "Thank you honey." He just laughed. "I will be back on Tuesday and have party to attend that night so you will need to go shopping and by and evening gown. Something in red, sexy but elegant." No problem baby." I told him that I had reservations at my hotel and for a cruise to the Caribbean that needed to be cancelled. He told me he had already taken care of the hotel and that I would still be going on the cruise with Rikki and Margo. I asked how I would be able to travel with a male passport. He told me not to worry. He reached behind his chair and pulled out his briefcase, opened it and took a couple of credit cards out, a drivers license and a passport and slid them across the table to me. The credit cards were in Danielle's name. The drivers license and passport also said Danielle and had my picture on them and both said female. I must have had a bewildered look on my face because he said "Its amazing what being filthy rich can get you." "You must have some good connections to get this done so quickly." I said. "I do" was all he said. Then he told me that my main responsibility during my time as Danielle was to keep myself in shape and sexy and to do whatever he asked to keep him happy. He again warned me not to cross him and I agreed to be on my best behavior. He said very good and said it was time for a swim.

I stood up and removed my robe and watched as Tony walked to the pool and dove in. I flipped off my shoes and strolled over to the stairs walked sexily down the steps into the water. I dove under water and swam across the pool to where Tony was and popped up in front of him. I was a very erotic experience swimming in my new body, completely hairless with big breasts and long hair flowing down my back. He reached out and pulled me close to him. He leaned against the side and put his hand on the back of my head and kissed me. I felt his tongue enter my mouth and it felt wonderful to have him being passionate again instead of all business. I felt my breasts flatten out on his chest as he pulled me closer and I felt his cock hardening against my stomach. We continued to kiss and I wrapped my arms around his neck and just enjoyed the feeling of his tongue in my mouth as his lips massaged mine. I instinctively spread my legs so he could rub his cock on my clit. He was hard now and had his hands on my ass pulling me into him an was moving my ass up and down so my pussy was rubbing the entire length of his shaft. I was really getting turned on and could feel my pussy getting juicy. This went on for a couple of minutes and then I felt his hand come around to my pussy an slide my thong to the side to give him access to my love nest. He dropped his suit to the bottom of the pool and wasted no time sliding inside me and it felt so good. I felt so full as he slowly slid in and out of me. He was taking his time and enjoying my hot wet pussy. I was sucking on his tongue as he worked it in and out of my mouth. He moved away from the side of the pool enough for me to wrap my legs around him and draw him deeper into me. That gave me leverage to move my ass around in a circular motion and work his cock from every angle. I knew he was loving it from the look on his face. We stayed like that for a half an hour or so. His hands were no longer on my ass. I knew what he liked and was moving my ass to please him without his help. He found my breasts and massaged them roughly pinching the nipples and making me moan bringing me closer to an orgasm. He was a master at reading and pleasing woman and when I was on the verge he pull his tongue out of my mouth and said "Cum for me baby" and shoved his tongue back in my mouth and pinched my nipples hard and began bucking his hips pressing deep into me. I was squirming around on his cock and pressed into him so my clit was rubbing him and erupted with a wonderful orgasm. I tried to pull away from him to scream but he held my head and kept my lips pressed to his and fucked my mouth with his tongue. I bounced up and down until my orgasm subsided and just hung limply perched on his rod. He finally pulled his lips off mine and "Now its my turn but I don't want a mess in the pool." I knew what he wanted and it was fine with me. He just gave me one hell of an orgasm and I wanted to satisfy him completely and really wanted to suck his cock and swallow his delicious seed. I slid off his cock and he sat up on the side off the pool. I slid up to him and pushed his legs apart roughly and pounced on his cock like it was my last meal. I kissed the head and opened my mouth and took him deep into my throat. I used my hand on his balls and aggressively sucked him. Wanted to suck him. Needed to taste him. He felt so good in my mouth. So natural. I put my hands on the edge of the pool with my arms straight and used the my buoyancy in the water to slid up and down on his cock. It felt like doing pushups only with a cock in my mouth. When I bent my arms he slid deep into my throat and when I straightened them he slid out. I worked him over loving the feeling of power as his sighs of pleasure grew more and more. His cock was so hot and his veins were swollen and I could feel his pulse on my lips and tongue. I knew he was getting close so I took him all the way down my throat and massaged him with my throat. I pulled back a few inches and went back down and continued this way until he moaned loudly and began to cum in my throat. "Aaaaaaaaahhh." I pulled back because I want to taste his cum and not let it just shoot down my throat. He shot another big load and I enjoyed every succulent drop. I had become very fond of the taste of cum in such a short time but I think part of the reason I enjoyed it so much is what it represented. My power over men and the satisfaction in knowing that I was very good at pleasuring men. I milked him until he was empty and then licked him clean. "Damn your good girl." "I'm glad you think so because after all you created me." He slid back into the pool and slipped his trunks back on. He said that we needed to do some laps to stay in shape so we did. I swam almost every day back home but it was much different with the body I had now. I felt great gliding through the water. The water flowing through my breasts and over my smooth crotch was very erotic and the fresh taste of cum on my tongue made it even more of a turn on. We finished our laps and toweled off and sat back down at the table. Tony and I picked some at the tray of food and talked a little about the area, his club and other things he was involved in. He said it was time for him to get ready and that I could lounge around the pool for a couple of hours be needed to be ready by 3pm for Rikki to pick me up. He told me that Rikki and I would be going to check on his sugar cane crop and for me to wear jeans and boots because sometimes there were snakes around. I shuttered at the thought but nodded OK. He stood and kissed me on the cheek and said see you in a couple of days and walked away. I watched him as he left realized why I woke up sore. He was one big strong guy and he had his way with me. Some visions of last night popped into my head and all I could think of was how I hoped Rikki was as good a lover as Tony.

I laid around for a while taking a dip or 2 when I got hot. And then fell asleep in a lounger. I was awakened by someone running there hand up my inner thigh. I opened my eyes and Rosa was sitting on the side of the lounger in a white bikini stroking my leg. "Hola Senorita" she said. "Hello Rosa" I said. "You are very beautiful Danielle." I started to say thank you but Rosa leaned down and kissed me pushing her tongue between my lips. Her hand was roaming my hips and ass. Her lips were soft and her tongue tasted like strawberries. I felt her nails being dragged across my bare skin and it was a very exhilarating feeling. She pulled up and took my hand and said "Swim?" She led me to the pool and she slid her arm around me as we walked down the steps into the water. We both took a dip and played around for a little splashing each other and laughing like girls do. Then she ducked under water and swam toward me and came up in front of me. She was very close to me and I felt her hands on my hips. They flowed up my waist and cupped my breasts as she leaned in and kissed me again. She played with my tits and nipples but in a different way than Tony did. More playful but yet more sensuous. She let 1 hand slid down between my legs and began rubbing my clit through my thong. I made a sound like Ummm and she pulled her head back and said "You like." I nodded yes and she slid her finger under my thong and ran her finger along the full length of my pussy lips. Then she began to nibble and tongue my ear and neck. Her other hand found its ways under my bikini top and she grabbed my nipple with her thumb and forefinger and squeezed but just enough to make me squirm. She seemed to know just how to manipulate my nipple to get me hot and wet. Her finger slipped into my pussy easily because I was so wet. Then there was 2 fingers. I rocked my head back as she continued to kiss and suck my neck and I felt so turned on. No wonder lesbians are so happy together. They no just how to touch and please each other. I hadn't noticed but she had walked me across the pool to the steps and pushed me slowly down on the steps and laid on top of me. Her fingers were still inside me and she slid my bikini top to the side exposing my nipple and wrapped her lips around it. She sucked and nibbled on it as I began to moan and squirm more vigorously. I squirmed further up the steps and she followed. I sat on the top step and laid back totally under her control. She alternated her lips between my nipples as she continued to finger me. Then she began to work her way down kissing my waist and belly button. Then my hips and inner thighs. I felt her fingers slide out of me and she slid my thong down to have access to my pussy. She wasted no time going down on me and I felt her tongue lick my pussy and then slid inside me. She pressed her face into me as her tongue darted in and out. She was humming her sighs and it was driving me crazy. She spent the next 20 minutes eating my pussy, taking me to the edge and backing off. She knew exactly what to do because each time she brought me closer and closer to an orgasm before she would back off. Both of her hands were on my tits and nipples the entire time and it felt wonderful. Then she brought her hands down and spread me wide and started to devour my clit. Her teeth had my clit locked in place and her tongue was working overtime brushing up and back on it then side to side. It was only a minute or so before I was cumming. I grabbed her hair and tried to pull her away but she held me firm with her teeth and continued to make me cum. I was floundering around as she kept me in a constant state of arousal and worked my very sensitive clit until I passed out. I was woken up from La la land by her splashing water on my face. "You OK Senorita" Rosa said. I didn't speak. I just nodded my head yes as she held her hand out to help me up. I sat up to regain my composure and splashed a little more water on my face. She had pulled my thong back up while I was out so I grabbed the handrail and stood up on wobbly legs. Rosa said "Its 2 o'clock and Rikki will be here at 3 to pick you up so you better go and get ready." "Yes thank you Rosa" I said. "No thank you Senorita" she said as she cupped my ass and kissed me. She took my arm in hers and we walked into the house together. She pecked me on the cheek again and headed for the kitchen as I went up the stairs to get ready for my hot hunk Rikki.

Next: Chapter 7


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