Date: Wed, 10 Mar 2021 23:12:41 +0000 From: S Hardman Subject: Play Ball teen tg category *None of this happened. It is purely fictional and between fully consenting parties. It's not real at all. If sex acts likek this offend you or if you are under 18 do not read. *Consider a Donation to Nifty.org. Play Ball There was that bounce of the basketball again. It brought about a conditioned response. Small beads of sweat broke out across my forehead. My stomach got butterflies. My mouth watered. My cock hardened. I felt a burning feeling of pure lust. I immediately went to the window. My window overlooks the driveway of my neighbor's house. I can see their garage and have a great view of the driveway hoop where the object of my desire spent a lot of time shooting baskets. It was the neighbor's teen son. If you looked at him you wouldn't know that he was a boy though. You'd have seen the prettiest femboy you've ever laid eyes on. Mark had shaggy dark hair and a thin feminine body. He really played that up. He wore a half shirt that was literally see-through. It was the shorts that really drew me in though. They were incredibly short and rode up on his hips and were so tight that they made that magnificent femboy fanny poke out and scream to be plundered by a cock, specifically my cock! I'd witnessed tons of his games from above standing in that window. I wondered if I was conspicuous and if he'd ever seen me. I tried to stay back especially when I extracted my cock and jacked myself to release imagining those sweet, sweaty long legs resting on my shoulders as I jackhammered that delicious feminine fuckhole. As he swished a jumper I became a sissy loving cum dumper! I turned away and once again felt the blood flush to my face with shame. I swore it off again but I knew later on when he did squats in the garage I'd once again take my place in the window with my engorged member in my hand. To describe myself you have to go back a few decades. I'm 51 and I've spent my life in oil and gas and I've put away lots of money. I don't want for anything so I live a life of leisure and frivolity. I play my video games and have invited women of all shapes and sizes into my home to sample. But over the last 10 years I have been exclusively a femboy pussy devotee. The long legs and smooth faces are so intoxicating. They give an attention to detail that is lost in the art of loving these days. They know all the right spots to touch and are eager to please. They love to dress their best and are horny all the time! My boner pills were getting used a lot that is until I fell madly in lust with the sissy neighbor. When I heard the garage door go up in a few hours I took my place at my perch. He picked up his hand weights and started doing squats. He wore his normal half shirt and as I looked closely I thought he was wearing girly panties. The back of them went straight up his back pussy and I got chills! The workout was extended and he must've bent over a hundred times. He was really working that ass. It was almost like he knew he had an audience. I was worked into a real lather when I exploded. I was going to have to wash those curtains. I was probably grunting and moaning. Hopefully he didn't hear me. He toweled off and so did I. A few days later as I was deep into a Call of Duty mission the doorbell rang. I frustratingly threw my controller aside and answered the door. There stood the object of my obsession in those damned tight shorts. I hadn't really seen this femme creature up close in a few years. The porcelain skin and full cock sucking lips were enough to make my stomach flip and my cock twitch. I mumbled out, "yes? Can I help you?" "I've noticed you enjoy my basketball skills. I was wondering if you wanted to play some one-on-one. I can't improve any more without an opponent and I want to get really good." The voice was cuter than I expected. The perfect amount of femboy lilt. Oh I wanted to play one-on-one alright just not basketball. "Sure, Just give me a minute to get dressed. Come in." He stepped past me brushing against my arm. It was so soft. I'm pretty sure he was wearing perfume and maybe a little makeup. He looked like a sissy lover's dream! I was going to have to let my hard on subside before I could reappear. When I did in my basketball gear he was on my couch with her long shapely legs crossed in an upright sissy position. It was going to be my spank bank image for later. The competition was pretty high for the first few games to 21. He won and then I won. For a sissy he was a great athlete. In the third game the style of game changed. When he dribbled the ball mostly he just backed into me crushing his sweet feminine ass into my crotch. It was strange but neither of us stopped doing it. It went on for a few minutes. I even grabbed those sissy hips and pulled them back into me. He giggled like a girl and then eventually we played the normal way again. My mind was reeling and it's hard to play when you're hard. I let him win again and when we were done that little femboy threw his arm around my neck and ran inside. I went and showered up and soaped up my cock pretending it was his delicate hands doing it for me. This quickly became a regular thing. We would play 3 to 4 days a week. When he got home from school he would text and we would meet in the driveway. Almost every time we played the `Butt Game' game always initiated by him. I called it the `Butt Game' only in my head. It started to dominate my thoughts. I imagined him more as a cheerleader in a little outfit than on the court with me. After the big game that little sissy cheer babe plopped down my shorts and gave my rod a wet tongue bath before retiring to the locker room for a celebratory butt pussy ramming! I would wake up in the dead of night sweating with a monster erection. Then he took it up a notch. He started inviting himself to play video games and hang out for hours at a time. Not only was he a beautiful femboy, he was the sweetest most charming person I'd ever been around. He was funny and smart with a sexy little walk and his giggling laugh was infectious. He explored my large Victorian home and found lots of interesting things from my childhood. Over the years I'd also collected quite a few things that were left by various one night stands or girlfriends. There were lots of jewelry and creams and clothes. I'd probably used some of the silkier ones to masturbate with. I hoped there wasn't dried cum all over them. He seemed very interested in them. He seemed pretty fashion savvy and even knew some of the designers and styles. I told him if he wanted to have them he could. He said, "No they should stay here. Maybe we can play dress up one day?" My ears perked up on that for sure. I wanted to see that really badly. I played it cool and said, "Sure whatever you want!" I was really becoming a simp for this little sissy unbeknownst to him or at least I thought. Then we went back to gaming. I had actually forgotten about it and I wasn't so obsessed with his boipussy for a while. On Friday 3 weeks later he came bopping through the front door. I'm glad I wasn't flogging the giraffe thinking about that sweet ass. I had done that a lot. He announced that his parents were out of town until the morning and he wanted to stay over. I wasn't sure what to do with this information but I agreed it could be fun. Besides how could I say no to the cutest little pouty face he gave me. I often stayed up all night playing video games or looking at sissy porn until dawn anyways. He came back over around 7 with a pretty full backpack. I was curious what may have been in there for sure. We played for a while and then he said he had to go to the bathroom. I kept playing but he didn't come back for a long time. In about an hour he appeared or should I say she appeared. Mark had his hair in the hottest little sissy pony tail. The sissy had his face made up perfectly. I guess someone had been practicing and had on a very sexy dress. He said she wasn't sure he should put on pantyhose or not. I stopped him quickly and told him that he should. He giggled and then disappeared again. When he returned he had on some white hose and red high heels that an old girlfriend had left. I had probably cum on them 10 times already. I was very careful to clean them and I was thankful I had. My dream was coming true. I now had the perfect femboy in my house looking like a model right next to me. I asked him what his girly name was when he dressed. We both knew it wasn't his first time. He said he was thinking about Marilyn but also Marcy. Marcy made more sense to me and I said so. It was settled she was Marcy. I will now be referring her to as Marcy the rest of the story and with she/her pronouns. I'll also be using that vision of her appearing like an angel as my spank material from now until forever! She sat next to me like a practiced girly boy. I think she just wanted me to look at her but not bother me. I went back to my game and she was like the perfect gamer girlfriend looking at her phone being supportive. It felt so natural and she was so graceful. It wasn't like she was a boy in a dress at all. I wanted to lean over and part her legs and make her my possession but I restrained myself. It was the first of many costume changes. There were skirts and blouses and bikinis. It was so hot. I loved the little bulge that was obviously super hard. Hell I was all sorts of erect all night, too. When she finally went off to shower I am pretty sure in hindsight that she left the door open on purpose. Oh my GOD! Her ass was a work of art. I have a fancy all-glass shower enclosure and she was in full view and she was magnificent. I pounded my dick with to that sight and blew a big load I had to clean up quickly. She appeared shortly with a see-through baby doll and some matching panties that hid pretty much nothing. "Good Night handsome!" She blew me a kiss and later I blew another load. That silky nightie didn't belong to any of my former partners and so she had obviously been buying her own clothes, too. I have no idea why I didn't take her pussy and make it my own right then. She practically threw herself at me. I guess I was thinking I didn't want to move too fast and spook her. I would regret that for months. When she left that next morning in her drab clothes she frowned and said, "Maybe next time you'll show me what you've been massaging behind that curtain while you watch me play ball! You are so loud when I'm working out, too. You don't seem nervous then. It's a real shame because I've been practicing! Some of those outfits I bought for your eyes only!" She winked and blew me a kiss and left with a giggle. I was kicking myself all day for not ripping the outfits off of that teen slut and destroying her insides with my ramrod! I did take solace in that fact that she was telling me that she was willing to open her legs and mouth whenever I wanted to take my load. I would be taking advantage of that in a few days or so I thought. She texted me and sent videos from that night the next day. It was something I treasured for the next little while because the doorbell rang. I rushed to the door but there stood her father. I expected her and to say seeing him instead was very disappointing is an enormous understatement. "Hey Rich, I know you're friends with my son and we need lots of support. We are going to do an intervention." I said, "What?! An intervention, What for?" He told me to come to the house where Mark was. I hot footed it over and there was an aunt and a couple of cousins and someone from a school called New Horizons Boys School. If I wasn't in love with a teen femboy I'd get a job there for sure from the description of it told to me later. She was looking for very forlorn. The school official dude started talking. He said Mark/Marcy's parents had found some a very concerning search history on his laptop. Searches like `how can I make a man happy?' `how to give oral pleasure to a man?' `how to be the perfect sissy?' and my personal favorite `how to prepare my slick sissy hole for a ramming intruder from a 51 year old man with a huge cock?' I thought for sure the cops would enter next and cuff and stuff me and I would never get to cuff and stuff that little sissy doll. Nothing happened except some serious resistance from Marcy. She said she would never be anything but a sissy fag and no boys school would change that. The guy from the school promised that she would change and they would see to it. I was suddenly so sad. After everyone had their say she was allowed 15 minutes to disappear upstairs to her room to pack and get ready to go. I feigned an excuse and went up to the bathroom. She found me as I got to the top of the stairs and pulled me into the bathroom. She threw her arms around my neck and buried her head into my chest and sobbed. I calmed her as quickly as I could because we were running short on time. She pulled it together and she said she was sorry. I told her she had nothing to apologize for and I looked into her gorgeous blue eyes. Our lips met in what had been coming for months. She began to drop her knees but I grabbed her up and told her as much of a dream that was for me that we'd surely get caught. She got a huge smile and quietly said, "You dream of me?" "Pretty much every minute of the day and night. I've wanted to pull your shorts down and eat that ass pussy since I first saw you!" With that she fell into me and broke into tears again. She asked if she could at least see my cock and give me a hand job but I rushed her out to get packed and rejoined the bunch of bigoted assholes in the front room. As she was getting into the minivan that was about to take her away I wanted to grab her in my arms and run straight to a bridal store and then haul ass to Vegas for a quickie wedding followed by a slow sweaty night of virginity vanquishing involving injecting my baby batter into the belly of the teen sissy who was also the love of my life! Alas I just waved as she gave me the saddest look I'd ever seen. My cock was very sad, too! It was also relieved that maybe I wouldn't be standing in that window pounding it with all my might quite as much. I was alone again. I did a lot drinking to fill some of the time. I also did punish my weasel plenty, too. I had pics and videos that she'd sent in a last minute attempt to get them off her phone in that time up in her room. She'd left her backpack of silky sissy items for me to take care of that night. We both thought she would be making use of them soon while I explored her sweet nether regions. I used the hose and nighties to massage my dick. It still smelled like her and the fabric against my phallus brought me some grunt inducing climaxes. That lone kiss lived on my lips and I longed for more. I fell into a deep depression. I began letting less talented femboys into my house. Some were terrible and some were adequate. The best was a sissy who was one of Marcy's best friends, Cory. Marcy only had sissy friends because people are terrible and would not risk their reputation being friends with a sissy! Cory was a catboy and that's not really my thing. More power to you if you're a catboy though! Luckily he didn't have a cat mouth. He had an incredibly talented wet sissy boy mouth. He showed up to commiserate about missing our sweet Marcy but that didn't last long until that little pantywaist catboy was lying naked in my bed. I didn't take his ass though. I wasn't doing that until I could do it with Marcy. That would've felt like cheating. Cory was a pro and I ejected lots of sperm onto his face and into her mouth. He loved it! It was going to be our secret though. I didn't want to make the love of my life jealous. She was able to write a few times. They were mostly how miserable she was but contact ended just a few weeks into her cloister! The misery lasted 4 months until a knock came on the door one day! There she stood, the object of my deepest desires. She leapt into my arms and our lips met. I pushed her back and told her we had to be careful. Why was she there? Was she staying? I told her I couldn't live without her. She said, "Calm down Daddy! My father has no idea we are anything. He thinks you are the best influence." I thought, "What a moron! He couldn't tell my terrible intentions for his sissy son as I ogled his ass every day during our ball games or as he was driven out of my sight that day?" I needed to know what happened. She said she would explain everything this weekend when she was staying over at my house. She kissed me again and said she'd text me and expect to make a porno with her that weekend! My dick sprang to attention! Friday night took forever to come and she had been teasing me incessantly. I was so ready to bend over this little bitch. She showed up around 7. She immediately wanted her backpack. I hoped I'd cleaned all the cum off of her stuff. I'd added a few surprises and she showed back up in one. It was a red camisole. She had on tan pantyhose and red high heels. We went up to the man cave. That was where I was going to explore her woman cave. She plopped on my lap and we started making out. My fantasy was right here on my lap directly against my engorged cock. I wanted to know why she was suddenly home. She had quite a story. The first week she was there she discovered the school was nothing but a boi pussy factory. She said her parents were idiots. Had they done even the smallest amount of internet research they would have seen the reviews. The school wasn't there to `rehab' anyone. It was a recruiting station. The staff and some of the older boys started taking bets the first day on who would `pop my sissy cherry.' I didn't let any of them near that. That cherry belongs to my Daddy, THAT'S YOU! I pulled her so close. I was happier than I'd ever been. She said she did now have lots of oral experience. That is what kept her and the other hundreds of sissies there out of trouble. She had sucked their way to straight A's and never attended any classes! But she was smarter than the other femboy floozies. She hacked the school computer and found hundreds of incriminating emails and blackmailed the Headmaster. She'd given him some masterful head by the way. She threatened to expose him and he couldn't afford to lose all that money and all that access to sissy pussy either! Sissy pussy makes the world go round! She was suddenly `rehabilitated'! "I have to just be careful not to google things like `How to get my throat choked by daddycock and still look like a million bucks' on our home computer! They took my laptop. Besides I'll get all the real world experience right here in your arms Daddy!" I laughed and then she said it was time! "I'm your little Cock Princess now. I will do anything you command. That is one lesson I learned at school. Sissies always do as they are told." She wanted to start with a lap dance. That was how they got the teachers to give the extra credit was to tease the Hell out of that dick before releasing the tension built up it. I wasn't sure. This was months in the making and my man meat was at its boiling point! I was hard as diamonds. I needed that fuck hole right then! She began stripping and dropped the camisole in my lap. I settled into it when she ran her hosed foot against my crotch but it was time to take control. She was so gorgeous. Her milky white skin and ass made me even harder if that was possible. I took her toes into my mouth and enjoyed the feeling against my tongue. After I had my fill I laid her down on the couch and worked my way up between her legs. I pulled down the front of her hose and extracted that little clitty cock and massaged it. She was whimpering and moaning and I knew I had my little teen cum sponge right where I wanted her. I was her master now! She quickly soiled her tummy with sissy spunk. It was time to split that sissy open and inject my love juice into her! Having this perfect tranny untouched fuckdoll at my fingertips was too much. She was writhing in lust with her eyes closed. She was practically begging. I had not really gotten to explore her body at all but now was not the time. She indicated she was ready and I pulled off the hose and positioned he legs on my shoulders. Her body was free of hair except for a little landing strip above her clit. I found out later that was in the rules at the school that all sissies needed to ladyscape every day. Her pussy was slick with my spit. I put the head at the entrance to heaven and started working it in. She moaned loudly and tried to push back and stop me. I was having none of that. Sissies need to be able to take their man's meat at any time. She was going to get the practice from the very beginning. I worked it deeper and she relaxed but continued to moan. I think she had learned that men love to hear their femboys moan. She then started begging for me to impale her. "Fuck me daddy! Fuck the man out of me! Pound me!" With that I got going. I piston fucked her tight sissy asshole with full authority. I went all in! I pounded her and she was almost screaming. The sound of thighs slapping had her moaning like a little Japanese sub sissy. I bit down and I hammered the maleness out of her. I came a bucketload into her girly bowels as I kept if buried. It eventually softened and popped out. She kissed me for a long time and said, "I am so in love with you big daddy. You're my king and I knew it would be amazing but never knew it would be this good." "Oh baby sissy Daddy is going to drive his dickwagon into you a million more times! We are just getting started tonight. Now clean me up with your mouth." She got right to work and licked me spotless. In an hour I was ready for round 2. I started exploring every inch of her sissy body including her soiled asshole. It smelled heavenly. I then started at her toes and worked my way up and around that clean tight sexpot. She was worth the wait. I wasn't waiting anymore. I injected another load into her horny bottom and before we fell asleep she showed me her mouth skills. She was very skillful indeed! When we awoke I bathed her in cum in the shower and then let her go home for the day. Our kiss as we left was the most sensuous we'd ever had. I was in love with a teen femboy. This continued every few days for a few weeks and then I needed some downtime. I was exhausted. We didn't see each other physically from Sunday until I walked in from some daytime drinking on Thursday. I heard some movement upstairs that I recognized as heels on my wood floors. I went up to find a gorgeous pouting fem goddess in a blue dress and tan pantyhose and open toed black fuck me heels lying in my bed. "I'm so mad at you, daddy!" I was definitely confused. I asked why. "We sissies have rights you know. We have to right to have our little fuckholes filled with man dick at all times. I haven't been fucked in days. I need it and I demand my rights as a sissy fuckdoll to be filled with your cock and to drink my fill of you seed." I actually looked up the Sissy Bill of Rights and it mostly consisted of the right to be stuffed with cocks in their mouths or assholes all the time. The overriding theme was that their Daddy had the final say in all matters of their lives. I howled with laughter and reminded that unlike her I was not a teenager and I needed a few days to recover. I then promised to spend the entire weekend fucking her. She demanded to have my dick in her mouth right that instant in the meantime. I complied and painted her face and I'm sure I Lewinsky'd her blue dress. We were in absolute bliss. The problem was she was still expected to be a regular boy at her house and I missed her at night. We needed a solution. I needed access to that hot sissy pussy whenever I wanted. That little sissy belonged to me and we both knew it. She longed for my cock when she was without it. I longed for her sweet fragrant tight ass pussy, too. I was over at their house quite a bit, too. Those idiots were oblivious that I was pounding their sissy son or so I thought. That sissy was a horrible tease. I had dinner over there at least once a week. She'd wear hose or stockings under her pants and slip off her shoes and rub her hosed foot in my lap. She even bounced up and down on my cock in her room when they thought we were playing games. We were definitely playing games but mostly playing ball. She was playing with my balls. I eventually had to formulate a plan. I took Richard, her dad, aside and flat out told him that I wanted to buy his son. I was addicted to that sissy. He didn't act all that surprised. He's heard plenty of noises and seen plenty of ass play on the court to be in the dark. He knew I was playing hide the missile in the meat cave with this little bitch boi. It turned out he was just jealous. I then had the perfect plan. Let's get this guy a little side piece of sissy slut pussy and some spending cash. The fat mom didn't need to know. I offered $30,000 or $15,000 and access to a femboy fox. He took the latter with very little fuss. I was glad I didn't have to kidnap the little limpwrister and hold her in sexual servitude. I was holding her a lot more in servitude in my bedroom, on the kitchen table and in my car. If I wasn't bending that little bitch over the arm of the couch then she was ejecting my nut on her lips and chin. I was in sissy heaven. We found a pretty virgin little sissy for Richard. Her name was Cherry. She had a short little red bob haircut and some serious dicksucking lips. I was actually jealous. I'd been with her a few times orally and always enjoyed myself. Her bottom was ripe for plucking. Marcy and I got married in a little home ceremony with Richard and 7 other little sissies. It turned into a weekend long orgy. The beauty of having a teen sheboy for a wife is that they are constantly trying to make an impression. They remember what it was like to feel like a girl but be a boy. That means they are constantly dressed the way you like, clean, shaven and ready to fuck. They fear losing you or even disappointing you. You don't perpetuate this but you do use it to your advantage. It makes for one hot sissy babe in heat. We have brought Cory into our bed on numerous occasions. I know where my bread is buttered though. So does my sissy wife. I keep her in constant chastity. Her only cum comes from sissygasms. I love to make her nut on her flat tummy. I'll allow her some hormones eventually but no boob or bottom surgery. I love my femboys with small bumps and panty bulges. I absolutely love blowing my wad on her girlish back when I pull out of that fantastic boipussy. Her little caged clit bouncing up and down while riding me will never get old. I love my little basketball sissy. Whenever I hear the sound of the basketball I still flush a little. The response in automatic. She still loves to Play Ball. As a matter of fact she was under the desk as I wrote this story playing ball with my balls.