Date: Fri, 22 Jan 2021 18:09:46 +0000 From: S Hardman Subject: RICH LITTLE SISSY teen tg category *This is totally fictional. None of this happened. It contains explicit sexual acts and if this offends you do not read. If you are not of legal age do not read this. *Donate to Nifty.org. This site is so awesome. RICH LITTLE SISSY I'm an accountant. I work in an office and I do what accountants do. Accountants do dull work in dull surroundings. That's why the job offer was a little surprising and a very welcome change to my dull life. I didn't truly know how it would affect my future. When I say the client that called is wealthy that's a serious understatement. He's not CEO of a Fortune 500 wealthy, He's owner of a Fortune 500 company wealthy. This family owns a chain of grocery stores that span the globe. He rang out of the blue and said he had a proposal. I'd done some side work outside of my firm for him so I had really gotten to look at his financials closely. He was disgustingly rich. He called and said he had been impressed with all the work that I'd done for him and truly trusted me. Some of the numbers were a little shady but not uncommon and I was definitely intrigued. He said I'd really only have to work a few days a week at the most and he'd triple my salary. I suddenly became very interested. He needed all his possessions catalogued and recorded for posterity and then valued for auction someday. Could I come for a meeting? I could! Two days later I arrived at the biggest house I'd ever seen. It was bigger than any house I'd even seen on television on an estate the size of Rhode Island. I was greeted by his personal assistant. He showed me into an enormous office and I greeted Mr. John Ream. I had only ever talked to him on the phone. He was a gazillionaire but he always called personally because he preferred discretion. He was very pleasant and after describing the work which honestly sounded a little time-consuming but very easy. He then took me on a tour. We started in the vault. The vault was just a big warehouse in the basement that held his archives, artifacts and priceless documents. I would work there some days and in the house on other days. I said I'd do it and I would start the following week. As soon as the firm heard I was leaving they'd want me out quickly. He said I'd hardly ever see him. He'd be on the road a lot of the time. He said I would see the maid staff that comes every other day and would also see Doll. I thought to myself, "Doll. That's a unique name. Who is that?" He led me to what I'd describe as a drawing room and said let me introduce you to Doll. He called someone on his cell and told someone to come in and meet me. In few minutes someone glided into the room. I am pretty sure my jaw dropped. It was the most gorgeous little girly boi I could ever imagine. This little sissy didn't walk, this little sissy floated. I felt my guts seize up. I have an addiction to sissy bois and I'd be alone in the same house with this one for months, maybe even years. She sat right next to me and stuck out her feminine little hand. I grasped it as the smell of her perfume intoxicated me. Her smooth hand and girlish arm mesmerized me. She had a perfectly made up face. She had a short boy haircut and girlish legs. Her little pink lips looked like they could suck a bowling ball through a garden hose. She wore a dress that came to the middle of her delicious thighs. When she spoke it was like an angel was speaking but I know a devil when I see one. My voice stuck in my throat as I eventually squeezed out a hello. I said I was Tommy Dickson. She giggled at how disconcerted I was and said, "Hi Tommy. Oh Papa. He seems so nice. Yay! Oh Tommy I can't wait to get to know you." She put her hand on my leg and then ran out. She wasn't fat but she wasn't rail thin either. She was perfection as I watched the most beautiful pert boi pussy bottom I'd ever seen disappear from sight. It was one succulent apple. Mr. Ream laughed and we talked some more. I don't remember what we really talked about because I couldn't get that little sissy angel out of my mind. I slept very fitfully that night. How was I going to function in an environment with kryptonite like that? I am a notorious bussy hound. I would have to figure it out. On Monday I put in my notice at my firm and was asked to clear out pretty quickly. I was a little sad to leave friends I'd worked with for 15 years but the other job was so much more attractive in several ways. I notified my new employer I'd report to work on Wednesday. I wore a suit for the first day and showed up to the secluded mansion. It literally took 15 minutes once you left the road to get back to this place. There were 3 checkpoints where you had to enter a code and another keypad to get in the side employee entrance. This place even had a helipad. I entered the study office that had been assigned to me and dropped my gear. I had a desktop computer there and I would also use a laptop. I then went exploring. It was up to me where I started and how I categorized things. I was trusted and I had a system already in mind. I really wanted to catch a glimpse of Doll but I started in the basement vault and walked the shelves. I figured I'd start there because I thought it would keep my mind off of the gorgeous femboy that was in the house alone with me. I didn't see maid staff that day but the place still looked immaculate. I then made my way upstairs. I started to see a few girly pieces of clothing strewn around on landing and down the hallway. There a skirt here and stockings there. I think she was used to people picking up after her. That's when I caught sight of a trap dream girl in the 4th room down the enormous hall. There she was laying across her bed completely nude. I started to make my exit when I heard, "Oh Hey Tommy! I was wondering when we'd meet again. I've been looking forward to it." She donned a robe but not that quickly. She enjoyed making me nervous. I saw her perfect body for the first time with her little dangling boi clit exposed. She had alabaster skin. I could tell she really savored my discomfort. She was finally covered but I couldn't make a sound. She giggled and said, "You're going to have to talk to me some time. I hope you don't mind. I am always so alone. I can't wait for us to be best friends." I found my voice finally and said, "Me too. I was just trying to figure out where to start all of this." She giggled again and said what her dad was doing was stupid and I should take my time with it. "Milk the old man for all you can get. You are way too overqualified for this job anyway. I hope you'll start in the house so we can see each other. I get so bored laying here all day." She then told me all about herself. She had recently graduated high school doing it virtually and had turned 19 last month. She was working slowly on her college degree. She didn't really have any plans to be in the family business. She wanted to be a writer. She was taking classes online. "I'm hoping you can help me with some of my work. I am just not great in math and accounting and that's your specialty. Isn't it?" I agreed that it was. I even worked up the courage to ask about the name Doll. She told me after her mom left and got a huge divorce settlement she had decided to stay here with her dad. Her mom didn't really like that her only son was a sissy dick lover. She said it just like that. It made a sheen of sweat break out on my forehead. She told me when she knew she was a sissy since she was very young. She'd found some discarded pantyhose and a sheer slip and had tried them on. She'd jacked off in them against the smooth fabrics and had been hooked. She had made a really sticky mess. She loved every minute of it. She was so open with her words. She was also enjoying making me squirm, too. Eventually she had bought her own clothes. It was easy with the internet and the fact that she was filthy rich. Her given name was Robert but she had asked her mom to call her Stephanie. Her mom just wouldn't do it. After her mom left she said her dad treated her just like a girl. Men always favor their daughters and he began calling her Baby Doll. She shortened to Doll. It was getting so easy to talk to her. It was a little strange that all she wore the whole time was that thin see-through robe but my hardened dick didn't mind. I got out of there while doing very little work that day. She told me to bring clothes and an overnight bag since it would make sense for me to stay in one of the many guest rooms most of the time. It had taken an hour and a half to get there that morning. The thought of me staying alone with that sissy boi at night in the house alone was exhilarating. I tempered that though. I didn't want to get fired from my job for getting caught fucking my boss' sissy son! That was only quality piece of ass though! I arrived early with my suitcase in tow the next morning. I parked myself in the large study and got to work. I set up a spreadsheet and after about an hour when I was about venture into the vault Doll came bounding in a tiny t-shirt and tiny panties that barely held her gurl cock. She pouted, "Why haven't I seen you? I was waiting for you up in my room. I get so lonely and I thought you'd come talk to me. Let's make a rule. You have to come and see me every morning and give me a hug. With that she threw her arms around my neck and snuggled into my neck. Ok deal!" She stuck out her hand and I shook it. She then ran out and back upstairs. I was beginning to see that she was kind of a rich little spoiled brat but her warm body next to mine felt so good. It was intoxicating. I was already addicted to this glorious sissyboi. Besides she smelled like a flower and I wanted to put my stamen into her pistil! So my daily routine was to run upstairs every morning. Sometimes it was a quick hello and others we talked for two hours. I helped her with her school work. I only stayed overnight in my guest quarters on the ground floor a few nights a week. She said she didn't want to disturb my privacy so she rarely visited. I really wanted her to visit. I am not sure if she knew my private time included looking at pics of her on my phone I'd taken and pounding my pud to them. She had asked me to take a few for her at times and I always used my phone so I could looked them later. I made videos of her, too. She was a natural sissy poser. I only saw her dad maybe once a month. He was very nice and we would meet and talk progress. He didn't really care how long it took. I'm not sure he cared at all. One morning after I'd arrived I headed upstairs. She wasn't in her room but I heard humming coming from her bathroom. I couldn't help myself. I crept over to the doorway which was partly ajar and peeked in. She was toweling off her gorgeous legs one at a time and then she bent over to continue and I caught sight of her beautiful boi pussy. It was so clean and inviting. I almost made a sound of excitement but I quickly backed up and pretended I was just coming into the room. "Uh Hey Doll. You here?" She came out with the towel wrapped around her and leapt into me. "Oh Tommy, I'm so glad to see you. I've got a test later this morning and I need you. God I need you!!" Nothing feels better than a fresh clean femboy in your arms! Hearing she needed me was nice, hearing it was because of schoolwork was less nice. Ha. So of course I helped and then got back to my work. In the afternoon she came bounding into my study and plopped down on my lap. "I passed!! I got an A on my test! All because of you" She kissed me right on the lips. I was a little shocked but it felt like a spontaneous response and frankly wonderful. She was so playful all the time and then I realized she was in a baby doll nightie and didn't have on any panties. She said she wanted to read her book in here with me if that was ok. She was lonely and promised to be quiet. I didn't care. I was making a bunch of money from her dad for doing basically nothing. So we sat and she was quiet for a while but eventually she got bored with her book and started chattering. She was just so cute and being around her made me warm inside. I realized I had moved past lust to love. I was in love with this little sissy minx! That was painful for me as I figured it could never happen. That night I dreamed about her in my guest room. She came in the dark of night and shed her nightie and climbed on top of me. She was completely bare and our warmth rose. Our cocks grazed against each other. She whispered that she wanted me to pound her butthole as she gripped both of our hardened tools together and begged for it. Her hand slid up and down our slick cocks. I sat up and turned her around and as I was about to sit her down on my girth she disappeared. At least I think it was a dream. I soaked the sheets in sweat. I was now a sex crazed man who had one desire. It was so close and yet so far away. She was such a tease it was painful! I was really distracted but I tried to work through it and continued on with the project. One day in the early evening I came up from the vault to find a man sitting in the foyer beside a stuffed full-sized grizzly bear. He was a middle aged guy in clothes that were more appropriate for a guy half his age. He was about my age but he wore a gold bracelet. He looked up and said, "You must be Tommy. I'm Jack." I shook his hand and was said it was nice to meet him. I was about to ask who he was when Doll glided down the grand staircase. She was in a sparkly short dress and it was low cut to showcase her itty bitty titty bumps. She was in tan pantyhose and had black open-toed high heels in hand. She plopped them on the marble floor and then put each gorgeous foot in one and made a real show of it. "How do I look Tommy?" She did a spin as I told her she looked beautiful. God she looked good. She said thanks and looked at Jack and said she was ready to go and they disappeared out of the door. I was a little stunned initially and then I got pissed. I had no right to be mad but I was. I finished up for the day and drove home. It was the weekend and I didn't return to the house until Monday. I didn't see her and I was still mad so I didn't visit her and went straight to work. In a few hours I heard her calling my name as I was kneeling down in one of the aisles of the vault hard at work. She found me and glided around a shelf. God she looked good! She was in a tight shorts and a half t-shirt that said Femboy Hooters and was really showing off her little bulge. She pouted, "Why didn't you come up this morning? I missed you! You were gone all weekend!" I said I was busy. I eventually got to the point after some small talk. "How was your date Friday night?" She snorted and said, "What?!" She then started laughing uncontrollably. When she gathered herself she giggled, "With my uncle? My Uncle Jack? Haha. He wishes. That perv has been wanting to violate my pooter since I first showed up in a dress and pantyhose as a teen boy at Christmas dinner. No! No! Gross! We had a charity ball that happens every year for trans youth. He probably took one of those poor unsuspecting sissies home. If I didn't know any better I'd think you were jealous. Don't worry baby! I only have one best friend Daddy!" I stammered and she enjoyed watching me dangle. She grabbed me around the neck and kissed my neck. She told me that she had a special dinner for us tonight at 7. "Don't be late and dress up a little." I flushed red as that plump little ass disappeared from sight she blew me another kiss. She was a little sissy brat!! I tried to work the rest of the day but my head was spinning. I was so distracted! Later on I heard music coming from the courtyard pool so I made a stroll by those windows trying to act casual. She was laying out on a towel in the tiniest pink bikini with her little bulge on full display. I took it in but quickly vacated before I was busted ogling this little tight trap. I tried to get back to work but it was useless. Eventually I just went to my room and started to get ready for our dinner. At 7 I went to the dining room. Doll floated in 3 minutes later looking like a sissy lovers' dream. She was in a little black dress, tan pantyhose and red Fuck Me heels. She had on little girly white socks over the hose that drew my eyes to her delicious silky legs. She was really playing up the slutty sissy look. That tight little ass was so sexy! In this smaller dining room where we usually ate she always sat at one end of the table and I sat at the other end with about 10 feet between us. She sat in the chair right next to me this evening though. "Hi Tommy. I've been looking forward to our date all day." I looked at her with raised eyebrows and said I had as well. I didn't make a big deal that she said date. It made me all warm inside and my rod stood immediately to attention. The first course of soup came after we had been poured some wine and then she told the servants to go home. "I'll be serving the rest of the meal to my Tommy." I was intrigued. After they left and we finished our soup she went out to the kitchen and brought out salad and bread. When she reappeared her dress was conspicuously gone. She presented the course in just her bra and pantyhose with the socks and heels on. Her excitement couldn't be hidden shown by her sly smile and hard little gurl penis. It was so cute poking out in her sheer pantyhose. I just smiled and played along. It was difficult because my fantasy was coming true. Then she brought out the main course for me. This time her bra was gone. He smooth creamy little breasts were exposed. She only ate the salad as I devoured my Chicken Cordon Bleu. It tasted amazing. She said, "Now it's time for the palate cleanser," and she disappeared. She quickly reappeared and presented a raspberry sorbet in a few minutes dressed in only the hose and white girly socks. She sat back down next to me and ran her foot up the back of my leg as we finished. When we were done she made a scene of licking her spoon. Then she stood and took each sock off and tossed them into my lap. She moved around to me and had me turn my chair. She sank to her knees and unzipped my fly and extracted my cock. I'm not a huge guy but my cock isn't small. She gasped as she gripped it. "Oh daddy. What a wonderful surprise. I was going to do this dinner later in the week but when you got so jealous this morning I knew the time was right. I had to let you off the hook. I need your cock and you need my little sissy mouth, don't you? You've been wanting me to suck the cum out of you for months. You poor baby!" She pouted out her bottom lip as she finished her tease. I nodded vigorously as she sank her lips over my member. The coldness of the sorbet was a strange feeling but as she began to move up and down the shaft it warmed quickly. She moved up to my purple head and then she sank it to the back of her throat. I pressed the back of her sissy head and made her gag a little. She was a pro though. She had obviously been training her throat for this moment. She came up and then kissed the head sensually and moved down the shaft planting little baby kisses as she went. She arrived at my balls and took them into her hungry mouth. The feeling was one of the best I've ever had in my life. My balls were full and I was ready to explode. She reached down into her hose and started pounding her little peepee as she loosely worked my man stick with her girly fingers. It was heaven. "When you saw me at the pool today did you hope and dream that I'd be sucking your big daddy dick later Tommy Bear?" I was a little embarrassed she'd seen me perving over her but it didn't stop me from saying, "No but I wanted you to for sure! You fucking beautiful sissy." She started working us both with more grip. Suddenly I tensed and shot a huge load on her sweet face as she creamed her hose. She grinned a megawatt smile and scooped whatever she could gather of both of our seeds and sucked it into her mouth with fingers of both hands and swallowed it down. "MMMM There's my delicious dinner daddy! Ok honey. See you in the morning." She got up and left me panting and stunned but very happy. The following morning after one of the best sleeps of my life I wasn't waiting any longer. I rushed upstairs for our morning appointment. When I entered her chambers she was on all on her bed with her back arched ready for action. She knew what time it was. She was not wearing a single piece of clothing. Her pert butt was staring at me and inviting me in. It had been slicked up with massage oil and off to the side was a tube of lube and a dildo. This was my official invitation. She turned and beckoned me with her eyes. I was ready to violate that virgin asshole! "Good morning daddy!" She blinked her big beautiful eyes. I quickly ripped off my clothes and my erect cock popped out of my jockeys. I hugged around her waist and pushed her down flat. She had prepared for me and I inhaled in her sweet hole. It smelled like a rose. I explored it with my tongue and she started moaning and wiggling. I worked it for a while but my hardened cock was ready and prepared to go all in. I pushed her body into the bed and parked the head at the entrance. It had been readied and I entered the lubed up hole. I sunk it slowly and she was moaning loudly. "Take my virgin boi pussy Daddy! Rearrange my guts baby! Fuck this sissy. Make me a girl! Fuuuuckkk!" That last word landed as I shoved my tool into her boi pussy all the way to the hilt. I started pumping harder and harder. I pulled her up to her knees and grabbed her shoulders and rammed her back into me. She was screaming and loving every moment as the last of any masculinity she retained was smashed to a pulp. I filled her up with my meat and then I flipped her over and put her legs on her shoulders. I looked her in the eyes as I grabbed her little cock and started playing with it. We locked lips and tongues and I gripped her little princess pecker tighter. In a minute she exploded on her own tummy right as I shot my wad deep into her boi bowels! We collapsed and she laid her head on my chest. We were covered in sticky jizz. The maid had a real job ahead of her. We fell asleep with the intense sleep of newfound love. We were now connected in a way I had only fantasized in my wildest dreams. When we awoke she beckoned me to her bathroom with a sweet finger and took me into the biggest shower I'd ever seen. It was amazing with multiple water nozzles and a hot tub. She kissed me and our tongues intermingled. We warmed under the water and my cock began to harden. She made dirty suggestions in my ear. We explored each other for a long time. She cleaned me and I cleaned her. She then put one hand and against the steamed glass and the other slicked up her pussy with a soapy cloth. She announced it was time for round 2. "Take what's yours now daddy! Pound my little pussy!" I then lined up my rocket on the runway and plunged it deep into her airplane hangar! I maneuvered in and out and then grabbed her hips and thrusted in and out for long time until I blew my batter deep into her again. It felt better than the first time if that was possible. We cleaned up and then dried and I went off to work. She pouted and threw a little shit fit. "Dadddddyyy! Don't leave me. I don't want to go." God she looked good. I had to work though. She didn't understand. What a rich little sissy brat! That night she slipped into my bed with a white nightie and stockings on and we made love again. It was so warm when I awoke with her across me. That routine continued for several weeks until she informed me that our room was almost ready. I'd seen workers going in and out for a while but didn't realize that we were moving in together in another part of the house. "Oh silly we can't live in that tiny room. Besides our weiners need to be together all the time. They're in love!" What a brat! The room that I was in now was bigger than any apartment I'd ever lived in but the new room was bigger than any house I'd ever lived in. She said it would do for now. I didn't really know what she meant by that. When I asked she just giggled. We had an entire wing to ourselves. The East Wing was very private and we explored every inch of it sexually. The maid had to clean up a lot of our collective splooge. We fucked all the time. I was breaking in her boi butt all for myself! I was also getting a lot done on my project but she didn't want me to leave some days so I didn't. One day about a month after our first erotic forays into anal fornication in our new room I said I had lots to do that day. She said, "OK enough of this. You're done with that stupid crap! I can't believe you haven't realized what's going on. Don't you get it? My father bought you for me. You're my version of The Toy. I saw him doing a virtual meeting with you one day last year and wanted to know more this sexy older man. I thought you were so hot. I have been looking for a Daddy ever since I was a little teen sissy. I saw you and I knew I had to have you. I told my father to buy you for me with the pouty look that you can't resist either. We keep wondering when you are going to figure it out. He wasn't sure but the first day I met you in his office I knew you would be fine being my daddy. You were so tongue tied. It was so cute. You are a femboy addict obviously and more specifically you're addicted to me. Then as we spent more time together I knew you were falling in love with me. I love you too Daddy! The house we'll move into on the compound is 5 miles up the road. It's enormous. Now quit doing that dumb job and get back in our bed where you belong!" I was flabbergasted. I had wasted many months of my life on a project that this sissy brat and her complicit father didn't even really want me to do. It was a ruse to trap me into falling for this little spoilt sissy. I was so mad and I started screaming and raging. She started blubbering and I told her I was going to finish it that week and go. I was done! I retrieved my stuff while she begged me not to go. I got a call from her dad's assistant in a few minutes. I didn't take it. Over the next week I worked quietly while seething. She'd appear out of nowhere and she looked better than I'd ever seen. Her dresses barely covered her sissy stick and she tried to talk sweetly or pout. She resorted to begging. "Please don't leave me daddy. I love you!" I didn't budge. I took all my meals back in the guest room. I finished out the next Wednesday with my final report that I put on Ream's desk. I immediately vacated the premises. It took about 2 weeks to calm down. I started having dreams about her and I would wake with a start and I have to admit I cried a few times. I was having withdrawals. When you leave an exquisite piece of sissy pussy like that there will be a time of depression and loss. I started to really miss her and her smell and quite frankly her mouth, her incredible mouth. I received an email telling me what an perfect job I'd done on the report and how I'd be on the payroll for the next 3 years and how sorry Ream was. He said that Doll was inconsolable and would I please reconsider. I thought on that for several days and then I finally saw the light. I had had a dream that we were married and it was our wedding night and I'd bred her sweet hole. When I awoke I couldn't take it anymore. I had had the dream scenario and I had let my stupid feelings blow it for me. I saw how insanely short sighted I'd been and I called her immediately. She answered on the 2nd ring. "Tommy?! Oh Tommy. I'm so sorry. I was so stupid. I should have been honest. I love you. Please come home to your little femboy mama!" "I'm coming baby. I have been so stupid, too. I love you!" When I saw her she threw herself into my arms. Our makeup sex was mind blowing. Also my cock got blown as well. We fucked so much the next few days in multiple rooms. The help was pretty used to seeing us in compromising positions. It wasn't strange for a maid to enter a room where I was dick deep in her delicious sissy boi butthole. We spent days in bed and then I made a big decision. I wanted to marry this sweet little teen sissy. She, of course, said yes! We had a June wedding in the gardens of the main house. We moved into Dickson Manor and now my only job is being the husband to this luscious femboy princess. She's now my queen! She graduated college and does some freelance writing like she wanted. For the first few years she hardly ever had clothes on. I live an incredibly full life. I get to wake up to that tight boi pussy every morning and pound it raw every night. I made some changes to her attitude to limit her rich little bratty behavior. We set some ground rules going forward. She actually occasionally has to do housework and help raise our kids. Yes, we have kids. It was easy to get a surrogate when you're as rich as we are. She gets locked in chastity for months at a time where she is only allowed to have sissygasms. When it comes off she is on her knees begging me for release. I have the last say in her decisions now. She occasionally messes up and gets bratty or calls her dad to tell on me. I punish her immediately and nip that in the bud and slip it in her butt! I am the head of our household and so this rich little sissy has to obey me. I am her big rich Daddy now!