Cassie's Dream Date 1 free porn video

So, I'm sitting in Starbucks drinking a latte and watching the tight asses of the male college students who work there, and dreaming of taking one home, when this 40 something guy comes over and sits down at my table. Listen, I'm hot looking and only 30. I don't date old guys. Truth to be told, I can't keep a boyfriend. First, not many guys can handle a supermodel. Second, those guys who think they can are scared off when I reveal that I'm a non-op transgender. That means I have a functional penis and expect to keep it. It freaks them out and I rarely get sex, let alone another date. I politely try to ignore Mr. Old Guy by folding up the newspaper that I spread across the table to avoid having anyone sit with me. But, he's not taking the hint. "Hi, I'm Roger," he says. I look over. He seems very familiar. "Hi." "I'm sorry if I disturbed you. But, when I saw you I knew I needed to come over and say hello." I look at him. "Do I know you?" "Roger Wilson. I wrote 'Love, lies, and lust'," he says. Bam! I knew he looked familiar! "Oh, sorry. I LOVED that book!" I exclaim, schoolgirl giddy. The book, about a transgender girl, explores her attraction to men and her difficulty in finding the right guy. It was on the NY Times best seller list for a year. TG's such as myself consider it a revelation that taught men that we were women. "I figured you probably read it." He said with a smile. "My name is Cassandra, Cassie for short. Why did you think I read it?" I asked "You know I couldn't just dream up that story. I've developed a knack for spotting special girls." He said, his smile broadening. I frowned. "Am I really that obvious?" "No, on the contrary. You look so good I'm sure you could pick up any guy in this place, even the married ones sitting with their wives. I just have this uncanny radar." I giggled. "Have you had success in finding your Mr. Toma (the eventual 'good guy' in the book)?" he asked. "No, not at all. I can barely get a third date," I confessed. "You're beautiful. You can't be having problems finding men," he consoled. "Finding, no. Keeping after revealing my secret, yes," I sighed. "You're picking up hot straight macho guys, aren't you?" "Yes, that's my type," I confessed. "You're dooming yourself to failure. The macho types are afraid of being called gay. The hot ones are interested in being only with hot women. And hot macho guys tend to spend too much time in the gym and not enough time reading, so they have no conception of what a TG woman needs. It's a bad combination," he explained. "So, I should look for sensitive, averagely attractive, and intelligent guys like yourself?" I said with a laugh. "Exactly," he said with a smile. I smiled back, then blushed. I don't think he caught the blush, because my hispanic skin is a dark tan, but I hope he did. There was an uncomfortable pause. "It was nice speaking to you today," he said, as he stood up. DON'T GO! my brain screamed. I extended my hand to shake his, my tongue tied in knots. He leaned over and took my hand softly in his. "It was a pleasure to meet you Cassie," he said softly. I wouldn't let go of his hand. He looked at me as I struggled to come up with something to say and stared at him blankly. "Cassie, Can I have my hand back?" he whispered as he leaned closer. I quickly stood up and threw my other arm around his head, giving him a one armed hug. "Thank you!" I whispered loudly into his ear as I released him. As he recovered and leaned back, I noticed he was reaching into his pocket. He produced a pen, clicked it to pop out the point, and then took my hand, turned it palm up, and wrote his phone number on it! I was completely in shock now. "Call me if you'd like to go dancing," he said with a smile. My brain clicked into gear. "No need to call. When can we go?" I blurted out. "Do you ballroom? Salsa? Or techno?" he asked. "I live to Salsa" I said, a little hip wiggle completing the answer. "Tonight? We can go to Pedro's," he asked. "Perfect!" I said. "Do you want me to pick you up, or would you feel safer meeting me there?" he asked. "Give me your pen," I said. He gave me his pen, and I wrote the address and my cell number on the palm of his hand as he laughed a hearty laugh. This guy was fun, even if he was 20 years older than anyone I ever dated. "Would you like to do dinner first, or just dancing?" he asked. My goodness! The guy was charming beyond belief. "Dinner would be lovely" I said. My previous dates could barely afford to buy me a drink! "I'll pick you up around 6 then?" he asked. "6 it is!" I said with a broad smile. We hugged again, and he was off. I watched out the window as he got into a Ferrari and drove off. I sat and finsihed my latte, daydreaming about meeting Roger later. I only had six hours to prepare for the date by the time I got home! I took a long COLD shower. Just thinking about going out with this guy excited me incredibly. I powdered myself. I put on my favorite perfume, Ralph Lauren Romance. My best panties, tucking myself in tight. I did my hair, cursing having had it in a ponytail when I met Roger. I was grateful for having done laser hair removal on my face years ago, but checked for any stray hairs anyway. I shaved my legs, even though they didn't need it. I did my arm pits for good measure. I put on my favorite dancing dress, cut all the way up to my hip and down all the way to my navel. My breasts, implants of course, were shown to their full glory. It was 5:45 when I realized that I had no appropriate purse! I was in a panic until I realized that this guy wouldn't allow me to pay for anything. I slipped a $20 bill, lipstick, mascara, and the key to my apartment into the world's tiniest red sequined purse, and put on my red dancing shoes. Roger showed up at 6:05. Truth be told, that extra 5 minutes caused me to nearly have a breakdown. I was SURE he wasn't coming. His knock on my door was a welcome relief. He hugged me and led me out to the waiting car. It was some kind of Rolls Royce limo, I think. His driver was holding the door open. You could have knocked me over with a feather! "I thought it would be best to have my driver take us, so that we don't have to worry about the Ferrari parked outside of Pedro's. I made reservations at The Palm at the Four Seasons. The food there is excellent." he explained. I climbed in. The car was lovely and huge inside. Roger climbed in next to me and held his hand out. I put my hand in his and smiled. He was already smiling. The trip to the Four Seasons was, oddly, over before either of us said anything to each other. We just looked at each other the whole time. It felt like he was staring into my soul. Dinner was very expensive, very good, and quite long. When we were leaving at nearly 9pm, there was a Frank Sinatra song playing in the lobby: "Fly me to the moon". Roger took my hand and swung me around, putting me into a ballroom waltz grip. "Do you waltz?" he asked. "Not well," I replied as I began to move to the beat. "You're doing rather well," he said, as he pulled me a bit closer. I mentally counted and stepped. I had a bit to drink at dinner and was quite happy to not be falling. I pulled him closer so that our hips touched. I figured if I started to fall, he'd be able to catch me easier. We danced for a minute or so. I became aware of his hand on my butt. I looked at him. He was smiling. I smiled back and put my hand on his butt. We continued dancing, having a GREAT time, laughing like teenagers over both our missteps. The song ended. He gave me a kiss on the cheek. "You are truly lovely." he whispered to me. I swooned. I hugged him. "Let's go, before the concierge tells us that the lobby isn't for dancing fools," he said. He produced his cell phone and made a call to the driver. By the time we had reached the sidewalk, the car was coming out of the parking garage. As we stood there, he leaned over and asked, "Do you always lead?" I must have looked puzzled because he added "You were leading while dancing." "I'm used to leading," I said. "Fabulous!" he said as he opened the door to the car and held out his hand for me to get in. When we were both in the car, he hit a switch and the panel between us and the driver appeared. Neither the driver, nor anyone else, would know what was said or done in the back of the car. "Cassie, I don't know if you understood my last question." "About leading?" I asked, wondering what was going on. "Robert Frost said that 'Dancing is a vertical expression of a horizontal desire.' Do you lead in the bedroom, as well?" Roger asked. My head pounded. I wasn't sure what to say, so I told him the truth "Usually." I looked straight into his eyes. He smiled a little smile. His eyes were bright blue. "What is your criteria for 'usually'?" he asked. "I don't really have one. I guess it's about whether my partner is more in the mood to play leader than I," I said, hoping I wasn't screwing this up, and cracking a nervous smile. "Listen, if we get to that point, I have to tell you that I'm both leader and follower. But, I do have one rule. The person with the biggest dick is going to play the top role." he said, very sincerely. I smiled, thinking that the latina wonder in my pants isn't that huge. "But, I have to add, I've only played bottom for one girlfriend," he said, smiling broadly. I smiled as well, and then leaned over and kissed his lips. A moment later, the car began to pull away and I ended up half on top of him. My hand instinctly reached out to steady myself and it came down right in his lap. I couldn't have aimed it better had I tried. He wrapped his arms around me, continuing the kiss. I didn't move my hand from his bulge. Well, actually I did, a little. I felt his member through the pants. We continued to kiss. His hands were feeling my ass, and it was good. We both gasped for air as we hungrily swapped tongues between our mouths. I began to squeeze his erection in time to his squeezing my ass, held in by the stretched fabric of the dress. I half expected the dress to rip open, given the long slit up the side, but it didn't. I don't know how long it went on, but suddenly Roger arched his back and thrust his hips at me. I had, apparently, jerked him off through his pants. He fell back into the seat, breaking the kiss. I let his member go and leaned back. He breathed heavily. "Sorry. You're SO hot!" he said. "Now we'll have to cut the date short, because I can't go to a club with wet pants." "Couldn't we get you another pair of pants?" I asked. "Would you mind?" he asked. "No, not at all. Actually, I was thinking you should just take me back to your place anyway. Just being with you in the car has made me incredibly horny," I said boldly. "There, leading again!" he exclaimed with a laugh. I laughed. He pushed the intercom button and told the driver to take us to his house. "Roger, how long will it take to get to your house?" I asked. "About 30 minutes," he replied. "Then you need to take off those pants. Otherwise, they'll be permanently stained," I said. "I'm ok," he replied, a bit embarassed. "No. Your suit is silk. You get it wet and it's destroyed. I'm not going to let you ruin a good $500 suit." I stated firmly "It's a $1000 suit," he said, looking down, even more embarassed. "Then those pants are coming off," I said, as I sat down on the floor. I removed his shoes while he removed his belt and unzipped and unbuttoned his pants. With a flourish, I yanked them down to his ankles, then pulled them over his feet. I folded them and put them on the floor on top of the shoes. "Turn on the light," I said. He turned on the light and I was able to see that his underwear, boxer- briefs, had a large and growing wet spot. I turned to the pants, feeling them. They were dry. "The pants are dry, thankfully. But, you can't put them on over wet underwear. You'll have to remove those in order to put the pants back on when we get to your house," I said. "That's not necessary. I can walk around my house in my shorts if I want," he said. "And have the chauffer think I'm some kind of slut? No way. You're putting your pants back on," I said. "How about I wrap a towel around myself?" he asked, growing more embarassed. I reached up and grabbed the boxer-briefs with both hands. "These are coming off." I said as I yanked them down. He lifted himself up a bit to let them come completely off, and off they came. His cock, somewhat flaccid and quite wet, bobbed in his lap. He was clean shaven down there. "I'll need a few tissues to clean you up," I said, examining the scene. He handed me some tissues from a built-in dispenser and I began to wipe the area dry. "Lift up a bit," I asked, so that I could wipe his cock. Taking hold of his cock with one hand, I began to wipe the shaft of the drying come. As I neared the head, I realized that I was acting like his mother, not his lover. So, abandoning the tissues, I licked the head of his cock clean with my tongue. He gasped a bit as I took the head of his cock, which was beginning to stiffen, in my mouth, to suck out any come that remained. He scooted forward, sitting on the edge of the seat, his legs splayed around me. I began to lick and suck his cock over its full length. His erection grew hard. I had no problem getting all of him into my big mouth, although the head did have to be in my throat. His smell was intoxicating. I moaned a bit, enjoying the feel of his cock in my mouth. He moaned back. I couldn't have him coming twice in 15 minutes. He's an older guy, and probably wouldn't be able to get it up again if I did that. So, I stopped, pulling his cock from my mouth with a "PLOP". "Awww..." he said. "The point was to make you clean, not to pop your cork." I said, wiping the excess saliva from my chin. "How is my make-up?" "It looks like you just gave me a blow-job," he said with a laugh. "Crap!" I exclaimed as I looked into one of the little mirrors built into the pillars. "Tissue!" I commanded him. He handed me a tissue and I wiped my dripping mascara and lipstick off. Finding my little red purse, I carefully applied new lipstick. But, I couldn't do the mascara because the car was on a rough road and I didn't want to risk poking myself in the eye with the brush. "Better?" I asked. "Yes. Lovely, but you were lovely with it, as well," he said. "Put on your pants lover-boy," I said, looking down at his now soft cock. He put on his pants. I again sat on the floor and helped him with his shoes. By the time we reached his home, he was all dressed. He folded up the boxer-briefs so that the wet spot was on the inside and put them into a pocket. When we exited his car, it was if nothing had happened in the back seat. His house, seen in the twilight, was large. No, it was huge. The chauffer dropped us off at the front door. There was no garage to be seen. It must have been one of the buildings we passed after we came through the front gate. As we walked to the door, it opened, a tiny and very pretty asian girl dressed in a french maid's outfit standing nearby. She said nothing, just did a small curtsey as we walked past into the entry way. It was magnificant, 2 or 3 stories tall, marble columns and floor, with a large curved marble staircase that seemed to float in space. Roger must have sensed my wonderment, as he took me by the arm. "This is the grand hall. To the left is the parlor, my office, card room, and ball room. To the right is the music room, the dining room, the day room, the kitchen, and the servant's rooms. Straight ahead, through the glass doors, is the indoor pool. Down those stairs is the game room... "Roger, where is the master bedroom?" I interrupted. "It's upstairs, to the right. There are 5 other guest bedrooms up there, as well as 2 maids rooms, a nursery, and a work-out room up there as well..." he said as I kicked off my dancing shoes, hiked up my skirt, and began a race for the stairs. He was taken by surprise, but was quickly on my tail, about 5 steps behind. By the time I reached the top of the stairs, he was further behind. I turned right, saw double doors open to a large bedroom and raced in, pulling my dress over my head and flinging it off onto a nearby chair as I leaped onto the bed. The bed was one of those tempurpedic foam things and my tall, model-thin frame was absorbed into it as I landed. Roger appeared at the door, a bit out of breath. I sat up. "See anything you like?" I asked, waving my boobs at him. "Oh, yes! They're perfect!" he said as he came closer. "They giggle!" "And they sag, like real ones," I added, holding out my hand in a STOP sign. "This is a no-clothes zone. Strip!" I commanded. He had his coat, tie, and shirt off in record time. His erection was a tent pole in his pants. He was down to his socks when he started coming forward. "Socks!" I pointed. He stopped to pull off his socks. As he straightened up, I got up and came over to him. I was still wearing panties. I reached out and grabbed his cock, which was rock hard, and gave it a squeeze. "Nice," I said as I kissed him and pulled him close. He squeezed my butt, then tried to pull down my panties. I pulled his hands away, broke the kiss, and said, "Not yet." He looked sad. I turned, pulling him by his cock, and brought him to the bed. "Sit," I commanded He sat, and I knelt between his legs. I brought my breasts to his cock and rubbed it between them. He leaned back and sighed heavily. I continued for a bit. He was enjoying this so much that I was sure he was going to come prematurely. So, I stopped and switched to giving him a good deep throat. When, after a few minutes, he started forcing my head down, I knew he was getting close again, so I stopped. I went back to using my breasts, but hadn't given him enough unwind time. He came, spraying my chest and neck with his warm sticky white offering. When he stopped coming, I leaned back so he could see his master work all over me. I giggled my boobs, causing the come to move around. In my best porn star impersonation, I even wiped come off my breast and licked my fingers. "Wow!" was all he could say. I licked his cock clean of come, and sucked what remained inside out. When I stood up, I leaned forward to give him a kiss. Unlike most guys who would be repulsed by being kissed by someone with come all over their lips, mouth, and chest, he was receptive. The kiss was long and sweet. I was laying on top of him. He grabbed my ass again. "You have a thing for my ass, don't you?" I whispered. "You've got a nice one," he replied. "Why don't I give you a better view?" I whispered as I got up and turned around. "NICE!" he said as I walked to the still-open double doors and closed them. I then walked around and picked up his clothes, bending over with my butt facing him each time. I deposited his clothes on the chair with my dress. Facing away, so he could look at my butt, I carefully untucked myself without revealing anything, then pulled down my panties. "WooHoo!" he yipped as my panties hit the ground, revealed my perfectly formed, heart-shaped ass. My own cock, now free, was rapidly inflating to its full length. I put my hands over it, turned around, and quickly returned to the edge of the bed. Roger was smiling. "Shy?" he asked. "A bit," I said. "No worries," he said sweetly. I opened my hands and my now erect cock fell forward. "I don't even need a ruler to see that you're leader." he said, breathlessly "I don't know Roger. I think we're about the same size," I said. "No, you're a lot thicker than I am," he said, reaching out to hold my cock. "Yes, definitely. And probably longer, as well." He squeezed it a few times. "Can I suck on it?" he asked I moved forward, putting my cock in front of his face. He didn't wait for an answer. He began to lick up and down the length of it. "Oh..." I said. "Mmmmm....." he hummed, as he took the head into his mouth. His technique wasn't all that great. It was obvious he hasn't been doing a lot of cock sucking. But, the zeal in which he approached the task was admirable, and it was also obvious that he was enjoying it as much as I was. He gagged when it hit the back of his throat, but kept going. I thought he could become a great cock sucker with just the right girl, me, to give him some pointers. After 10 or 15 minutes, I made him stop. His teeth were slowly making me sore. "So, what's your favorite position?" he asked. "I like cowgirl because I can look into your eyes," I said honestly. He scooted up the bed and opened the night stand. Inside was a large pump bottle of lube, half empty. He pulled it out and rollled onto his back, holding his legs in the air with his hands. "Roger, wait a second. Why is this bottle half empty?" I asked. "I use it on my maid," he said. "You fuck your maid?" I asked. "I'm training her," he said. "Training her to do what?" I asked. "To be a proper 1950's housewife," he replied. "Why?" I asked, all thoughts of sex lost. "Didn't you notice?" he asked "Notice what? That's she's pretty?" I replied "She's a ladyboy," he said. "Oh. Really? She's gorgeous! But why a 1950's housewife?" I asked. "In the 1950's, women cooked, cleaned, and attend to their husbands. Today, women go to work. Only rich men can have a stay at home wife. And rich stay at home wives don't want to be bothered to properly attend to their husbands. So, I have a business where we find young ladyboys in Thailand, train them for two years to be maids in an almost convent-like atmosphere, then bring the prettiest and most obedient ones to the US to get the rest of their training. I typically like to have a girl here for two years to properly train her before sending her to her final employer." "Roger, that's insane!" I replied, my erection nearly gone. "Not so. Think about it for a minute. These girls would become street hookers at home to pay for their plastic surgery. Now, they can learn a trade, get free plastic surgery, and, for a lucky few, escape Thailand entirely for a much better life in the west," he said. "A better life as a maid?" I asked. "A better life as the maid who shares her employers bed and is showered with plastic surgery, gifts, and, perhaps, money to bring their parents and relatives over," he said. "And you get to fuck these girls for years as training?" I asked. "They need to be beautiful, obedient, and know how to fuck like rabbits in order to make it here with my clientele," he replied. "So, your clients pay you to train/fuck their maids? Sounds like a dream job," I asked, completely incredulous. "Of course, $250,000 per girl. I can only train one at a time, so I have associates who also train, but they get less because my girls are top of the line-the most beautiful, obedient, and loving, and I'm such a good trainer," he replied. "I can't believe I'm hearing this," I replied. "Get her up here. I want to talk to her," I commanded. "What are you going to say to her?" he asked defensively. "Before I give you the fucking of your life, you nasty pig, I want to make sure the story you just told me is true," I said in my best Cruella Deville impersonation. He rang the servant bell. I sat down next to him on the bed, still naked, waiting for the maid to appear. He put his hand on my knee, but I slapped it away. I wasn't sure I wanted him to touch me. It didn't take long. The maid, An, appeared in less than a minute. "An, tell her where you sleep," Roger said. "An sleep in this bed with master," An replied. "An, tell me what this is for," Roger said, holding up the bottle of lube. "Lube for love making. Roger use it every time. An order it in case of six bottles from grocery store every month," An replied. "An, tell Cassie how we make love," Roger said. "Roger taught me proper oral skill so that I not gag when his big dick in my throat. He break in my virgin ass. He now showing me different positions for ass love making," An replied. "An, did you have lovemaking session with Roger today?" I interjected. "Yes. This morning. I woke up and began to give him blowjob, which I do every morning. He woke up and change to 69. I come first, as usual. I cannot hold back. He then love make in my ass from behind, doggie style?" An replied. "Yes, that's doggie style," Roger said. "An, you see I am like you?" I asked. "No, you bigger," An replied with a giggle. "Yes (laugh), bigger. But we both have woman parts and man parts, yes?" I asked. "I have girl parts and little boy parts," An said. "Would you take off your uniform and show me?" I asked. Without any hesitation, An removed her uniform. She had very nice, if small, breasts. When she untucked her penis, it was already hard. Small, even for an asian, her penis was, nonetheless, quite attractive. "An, turn around," Roger commanded. An turned. "Doesn't she have a great ass?" Roger asked me. "She's got a great figure," I replied. "An, come sit on Cassie's lap," he commanded. "Roger..." I started to say, as An plopped herself down on my lap and began wiggling her butt against my cock. It started to grow hard. "Roger..." I started to say again, as An took my hands and put them around her. Instinctively, I reached up to feel her small breasts. Her nipples were hard. "Cassie, An likes you," he said. My cock was fully erect now, pressed between An's butt cheeks and my stomach. It was beginning to strain. "You ass love An now?" An asked, riding her butt over my erection. "You very big. You ass love An very good. An will scream orgasm." she said in a sing-song. I could only say, "Yes." "An, on your back. Cassie will show you a new position, called Cowgirl. You will like it very much," Roger said. An got on the bed and pulled her legs up, exposing her hole. The deep brown ring around it showed that Roger had used it regularly. Roger squeezed some lube into the general area, and offered the bottle to me. I liberally coated my iron pipe with lube. "An, Cowgirl is like Missionary, except your feet will be near the shoulders of your lover. For that reason, your feet must be very clean when you do this." Roger said, as I positioned myself at the entrance to An's ass. "An, I'll go slow," I said, as I eased my cock to her opening. An nodded as if she understood and pulled her butt cheeks apart with her hands. I bore down. The head of my latina wonder began to ease into her ass. In a moment, I felt the head pop all the way inside. An made no noise, no sound, but her mouth was wide open, and her head tilted back. I pressed on, my cock travelling up inside this girl's tight ass. I could feel her rythmically pulsing her sphincter, not to push me out, but to give my cock a playful squeeze. After another moment, I felt my cock head hit the end of her colon. "Ugh. You very big. An very full," An said breathlessly. "An, is she bigger than me?" Roger asked. "Yes. She bigger. An's opening very stretched. Feel good," An replied. "An, I'm going to show you now the Cowgirl position and start moving. When I do that, I will not stop unless you say RED. Only say RED if you are in great pain. Ok?" I said. "An say RED if in great pain. Ok," An said. I straightened out An's legs, bringing her feet up to my shoulders. Her calves rubbed my breasts. I began to move my cock. Roger came close and put An's hand on her own cock. She held it as it involuntarily spasmed and sprayed come each time my cock head went past her prostate. An began to moan. I was getting more and more excited, moving my cock in and out of her slowly, trying hard to not tear or hurt her. Roger began to play with An's nipples, causing her to moan loudly. An's hand began to pump her wet cock furiously. I built up my pace. An orgasmed. Her come hit my chest, her chest, and Roger's hand. I couldn't hold back from the excitement, and blew my load deep in her bowels. I could feel it being blown around my cock, her hole being so small. I stopped moving, my cock embedded deep inside her. We were both out of breath. "You go again?" An asked. "No, I need to rest," I replied. "You go again tonight?" An asked. "Yes, but with Roger," I replied. "An sad. You very good love maker," An said. I blushed. "I try. I'm going to let your legs down now and take out my cock. Remember RED if in great pain," I said. "An ready," An said. I eased myself out. An's ass was covered in lube and my come dripped out of her. There was some blood too, but Roger said that it wasn't enough to worry about. When I released her legs, she rolled over onto her stomach. Her cute little ass looked quite fuckable. I could see Roger's client loving this girl. She was just the right mixture of beauty and cute wrapped into a body that said "FUCK ME!!!!" An turned over onto her side. "You take shower with An?" she asked. I looked over at Roger. "Cassie would love for you to bathe her," Roger said. An hopped out of bed and trotted to the attached bathroom. I could hear water running. "Give her a few moments to clean herself off, and then join her in the shower," Roger said. "Oh, by the way, she's usually frisky in the shower, so be prepared." "Frisky?" I asked. "She dances and wiggles and generally gets you excited so you want to fuck her again," he said. "So, you've made her into an insatiable sex addict?" I said. "That's generally my goal, but this one is over-the-top. I suspect it's because she's so young," he said. "How old is she?" I asked. "Her passport says she's an 18 year old female, but I think she's really 15 or 16. When they send over young ones like that, they're almost always kids that they got before they had any serious sexual experience. Throw 2 or 3 years of maid training, where any sexual contact gets you thrown out of the training program, and you end up with a girl that just wants to fuck constantly when she arrives here." he said. "I see. So, I just fucked jail-bait? Great..." I said. "According to her papers, she's 18," Roger said. "You implied that you've had a number of these girls?" I asked. "I have, on occasion, had to send girls back because they were disobedient, or WAY too young, so I've probably trained 14 or 15 girls, of which about half have graduated from my training," he said. "You should go get your shower now." I went into the bathroom, which was larger than my bedroom, and stepped into the shower. An was there holding a bottle of body wash and a wash sponge. The water running off her nipples drew attention to them. The water running off her long hair caused me to look down and see she had an erection. I came closer to her. She began to wash me, starting at my shoulders and working down my front. When she got to my breasts, she put down the body wash and used one hand to hold my breast while the other softly cleaned it with the wash sponge. My nipples were rock hard when she finished. I turned around when she got to my waist and she did my back and butt. She then knelt down and cleaned from my feet up. As she closed in on my cock, it bobbed with a good firm erection. She said nothing. Abandoning the wash sponge, she used her hands to wash my cock and balls. By the time she was done, I was nearly ready to pop. She stood up. "You like to wash An now?" she asked. I wanted to bend her over and take her again right there, but instead, I said, "Yes, I do." I followed her playbook, except that I didn't use the wash sponge at all. I used my hands. I began with her long hair, and followed it down to her breasts, back, butt, legs, and finished with her cock. After her cock was very clean and fully rinsed, I kept stroking it, pretending that I was still cleaning it. She was holding onto the handles in the shower, her orgasm approaching. I wasn't going to deny her, but I wanted her to not just pop quick. So, I stopped and said "Let me show you something girls with big breasts can do." as I put soap between my breasts and put her cock between them. As I stroked her cock with my breasts, she watched me intently. I knew she was getting close again when she closed her eyes and began to moan. As soon as she arched her back, I held her cock tight in my hands, pointing the stream of come onto my breasts. When she was done, I stood up and brought my breasts to her face. "You've made a mess young lady. You will clean this up with your tongue," I said. She came out of her daze to see my come covered breasts, which she then cleaned off expertly, using only her tongue. I think she spent more time than was necessary with my nipples, but maybe it's because my nipples are so sensitive. When I left the shower, Roger was there with a towel. I didn't even get to dry myself. His towel work was impressive. My cock literally ached for release when he was done. "Roger, is this counter-top strong enough to support your weight?" I asked, pointing my rock hard cock at him seductively. "I don't know. But, the sling in the attached room is..." he said, pointing out a door I thought was a closet. I grabbed his hand and pulled him towards the door. When I opened it up, I was shocked to see my fantasy sex room. The room was smallish, but had mirrors everywhere by the floor. A sex swing was prominent in the center of the room. The swing had its own built-in holder for a pump bottle of lube. A set of knobs on one wall suggested there might be closets behind. As I stood there, Roger climbed into the swing. An was there to help him, strapping him in place. When she was done, he was immobilized, his ass pointing at the door. I went over to him. He was a bit too low for me. "Roger, is there a way to raise you up a few inches?" I asked. "An, could you show Cassie the control board in the closet?" he asked. An opened one of the knobbed walls, which revealed another whole room next to this one. She walked in and pushed a button. Roger went up. "That's good An," I said, when Roger's ass was directly aimed at my throbbing cock. Ignoring An, I made liberal use of the lube. I was in a zone as I pushed my cock into Roger's ass. He grunted at my roughness. I plunged deep, seeking relief from my throbbing latina wonder. I needed to come. I began to fuck him hard. He stroked his cock, grunting or moaning at each of my inward thrusts. I noticed An, off to one side, but my focus was on pumping my come into Roger's ass. I was literally fucking the shit out of him, and he seemed to enjoy it. He came. His come arched out of his cock all over his chest. I kept pounding him. I began to call him names like "sissy", "pussy boy", and "sperm catcher". He cheered me on, telling me to fuck him harder. An came closer. She had a video camera and was taping me ravaging Roger's ass. "You like?" An said to Roger, pointing the video camera at his face. "God, it's great!" Roger replied. An pointed the camera between us, so you could see Roger's very distended ass wrapped around my fat cock as it plunged in and out of him. "You like?" An said to me, bringing the camera up to my face. "He takes cock well," I said. An moved the camera to my bouncing breasts, then down to my cock pounding Roger's ass, then lower, so you could see the lube dripping off us onto the floor. "Will be sore if you don't lube him," An said. "I'm almost there," I cried out. A moment later, I plunged deep and came in Roger's ass. I held the straps of the swing for dear life as I pumped his ass full of my come. When I finished, my legs were weak. An was right there with the camera, to record the withdrawl of my cock. "Look how long and fat her cock is. She gave master a good ass love. We watch to see her come drip out," An said as I stepped away. As the head of my cock cleared Roger's ass, my come began to drip from his ass. An zoomed in on his distended sphincter and the white cream dripping out onto the floor. She turned the camera to Roger's face. "You have fun?" she asked. Roger, still catching his breath, nonetheless was able to say, "I need to marry that girl!" An got a shot of my slightly droopy cock, dripping with lube and come, and then turned off the camera. We unstrapped Roger and helped him down. An help weak kneed and wobbly Roger to the shower. I took a quick look in the "closet", which was actually the same size as the mirrored room. In it were a number of special pieces of "furniture". Low tables with straps and adjustable heights, gyno tables, a vaulting horse, a small tampoline, many different types of swings, chairs, crosses, and some pieces that I just can't describe. I hurried back to the bathroom, and joined An and Roger in the shower. An, again, washed both of us to a state of excitement. This time, however, Roger allowed her to orally attend to us. Neither Roger nor I came, but we enjoyed An's lack of gag reflex immensely until her throat got sore. An left the shower a minute or two before us. When Roger and I exited, she was nowhere to be seen. We toweled each other dry and went back to the bedroom. An had changed the sheets on the bed. My dress and Roger's clothes were hung in a walk-in closet. She was wearing her maid's outfit. "Will there be anything you need before retiring?" An asked in a very professional way. Roger turned to me. "Would you like a cocktail before retiring?" "I've already given you the cock in tail," I joked Roger giggled. "That you have. And An got it too. I guess that will be all An. Why don't you come back in an hour and tuck us in?" he said to An "Yes, master," An said, curtseying and then leaving the room. I turned to Roger. "I thought she slept with you every night?" "She does. But, she needs to dry her hair from the shower, and that takes an hour. Basically, I was telling her it was ok to join us when she's ready," he said. "I get the impression that she likes it when you have guests," I asked. "I don't have guests. In fact, you're the first bedroom guest I've had for years. She's just likes a stiff one," he said matter-of-factly. I chuckled. "I need to get in bed before the air conditioning makes my nipples hard and my cock tiny." "Too late!" he yelled as he raced towards the bed, with me in hot pursuit. We both hit the bed, laughinng, and rolling around. Eventually, we crawled under the covers to snuggle. When he was behind me, he stroked my cock or touched by breasts. When I was behind him, I squeezed his ass or his cock. Eventually, I fell asleep with him in front of me, like a pair of spoons. I woke up briefly to An climbing into bed next to Roger. She had on some kind of red lingerie. During the night, I felt a mouth around my cock, but I was too tired to care or to come. Later, I briefly woke to find An gently sucking on my nipples. The next morning I awoke with a raging morning erection and a full bladder. I went to the bathroom and sat down like a lady to pee. After some time, my erection subsided and I was able to drain the snake. When I went back into the bedroom, Roger was just getting out of bed. As we came close, he reached out and gave me a hug and a good morning kiss. I felt his hand on my cock. He put it next to his. "I'm leader now," he said laughing.. "Give me a moment to get hard again!" I laughed. "I'll help you with that," he said, continuing to massage my cock and kissing me on the lips. A little tongue-play and a few minutes later, I was as stiff as a board. We compared erections. Mine was definitely thicker, but he was a little longer. I called it a tie. He suggested that he be leader then for the next 12 hours, because he wasn't the previous 12 hours. That sounded ok to me, so I agreed. Roger went off to the bathroom. I returned to the bed. An was up, and offered to relieve my Roger-induced erection. I told her I was no longer leader, so she'll need to ask Roger. We both smiled and laughed, since we know that Roger would do whatever we wanted, really. An got out of bed. Her red lingerie was a teddy that fit her shape perfectly. She was, in a word, fuckable. Her small nipples were visible through the lacy fabric, and they called to me. I'm not normally one to go for other women, but this girl was everything anyone could ever want. I called her over, and pulled her into the bed beside me. It didn't take by a minute for me to rip the teddy off of her and devour her nipples with my tongue. My hands went to the teddy's velcro crotch, ripping it open to get to her small, yet sturdy, package. She wasn't even tucked when the velcro released her cock. It sprang free, fully erect. I stroked it with my hand, then moved my tongue from her breasts to her cock. I took it fully into my mouth. She gasped. I knelt over her, my ass in the air as I frenched her little asian cock. It was delicious. Just the right size. An excellent shape. Almost completely naturally hairless. I didn't want to let it out of my mouth. I felt the bed move. Roger was behind me. I could feel his cock touching my leg. It was wet. His fingers touched by hole. They were wet with lube. Two went in. I continued to suck on An's cock. Two went out, replaced by his cock. It stretched me nicely and travelled unrelentlessly up my bowels. In truth, I enjoyed the feeling of Roger's cock in my ass. It felt like it belonged there. That is, until he pulled out and shot tabasco into my open ass. It burned. His cock went back in. It was painful. I made noises around An's cock, still holding it deep in my ass. An clamped her hands over the back of my head. Her cock jumped and flexed in my mouth. I could taste her sweet come hitting the back of my tongue. I swallowed. My ass, still on fire, was being fucked wildly by Roger, who saw An coming. And then, my ass was no longer on fire. Roger flooded my ass with his come, which killed the burning tabasco. He leaned down. I collapsed flat onto the bed, still impaled mouth and ass on An and Roger, respectively. When An's erection was gone, despite my attempts to keep it alive, she let me lift my head. I yelled out, "Who is going to suck the massive load of come out of my cock?" And, with that, everyone in Starbucks knew that I was a transgender who likes to daydream the impossible dreams. As I ran out of Starbucks, completely embarassed, I looked at the phone number written on my hand. I have a date tonight with Roger! Stay tuned for part 2 of Cassie's Dream Date! Does Roger really have a limousine, a driver, and a ladyboy maid in training, or was this all just wishful thinking by Cassie?