Everything here is fiction.
Ryan Is a fictional character with a little bit of me in him.
This is a repost from my story over on Xhamster and all work here is my own sick twisted creation.
Please let me know what you thought, people seem to like this story on other sites so I thought you would too.
This is my second story. Its about a guy and an older she-male. Enjoy.
This is my second story. Its about a guy and an older she-male. Enjoy.
Honey, TG nympho, discovers a whole new genre of sex
“Hey get up!” call Jennifer from the bottom of the stairs.
“Don’t make me come up there and get you up myself” she called again.
John didn’t want to get up. Out all last night drinking, made it real hard for him to even lift his head off the pillow. Why did he have to make that bet anyway? You see, Jennifer was real good friends with Ms. Edwards across and the street and she needed help this morning cleaning out her basement. Bruce (John’s twin brother) was the one grounded for hitting a ball through her attic window and was the one who would be helping her clean. John was pissed for making that bet, Bruce even knew John always like a good bet. Why did those fucking Colts have to lose? Now he was the one who had to get up at 5am to go over to Ms. Edwards.
“John!” call Jennifer one last time.
“I’m up, I’m up” “just give me a moment”
So, John got up and headed to the bathroom to get ready, but not before he punched Bruce in the arm as he slept in the bed next to him. Only to pissed John off even more, Bruce just rolled over and told his brother to have a get time cleaning and went back to sleep.
“What a fucker” he thought to himself as he walk into the bathroom and hit the light.
John looked across the room the mirror above the sink. There he saw himself 6’and in good shape, nothing extreme, he was average for an 18 year old with shaggy brown hair. He had his share of girlfriends, but he just ended with the last one about two months ago. As he looked down he could see his 9” hard cock poking through his boxers just wanted to be jerked. As he was about to rub one out he mother open the door to the bathroom.
“John?” “are you…”
“Mom?!” John yelled. “What are you doing in here?”
Jennifer froze, not being able to move or speak. All the blood running from her face turning it white. Again John tried to ask what his mother was thinking, coming into the bathroom.
“I’m so-rr-y” was all she could get out before she turned and walked out to her bedroom.
John looked down to see that his cock was even harder than it was before his mother walked in. Did he get turned on by being caught; even more that it was his mom that caught him. John looked at his watch and saw that it was ten to five. “This is going to have to wait till later” and he finished getting dress and headed to Ms. Edwards’ house.
“Hi, John” answer Ms. Edwards as she opened the door. “Why are you here and not your bother Bruce?”
“Long story short, Ms. Edwards” “I lost a bet and now I have to help you” John answered.
“Well lets get started, we don’t have all day, and call me Mary” replied Ms. Edwards.
So, John followed Mary to the basement start cleaning. As the morning went, John moved boxes and swept the floor and moved the boxes back. Mary unpacked some to see if there was anything that she could get rid of or give to the local school. As she would bent down to pick up a box John would look down her low cut shirt or look at her ass in her tight pair of work-out pairs. Mary caught him here and there but didn’t make it know that she saw him looking. Unknown to John, Mary was not your normal women nor was the singled woman she seemed to be, but was in a relationship for quite some time with someone John knew very well, but didn’t like to have other people knowing that because most people in that town did not see it as being right. This special someone was the only one in town that really knew Ms. Edwards, but that was going to changed after today.
“Well, John, we have been at this for four hours now” “why don’t you take a break as I get us some drinks” said Mary.
“Thanks” replied John.
Mary headed up the stairs to make the drinks. As she walked up the stairs all John could do was look at that ass as it moved from side to side. John’s cock was at full attention when Mary reached the top. He had to jerk his cock bad now. After his mother this morning and now Ms. Edwards, he needed to rub this one out. John headed up the stairs to find the bathroom. As headed down the hall as he walked down the hall he heard faint sounds and could see a light coming from a room that the door wasn’t closed all the way. He slowly creped up to the door as he heard low moans coming from behind the door, John look into the room only to find Mary sitting on the edge of the toilet rubbing a thick cock and biting down on her lower lip. Never has a man done this to her, never as a man made her so horny and she needed jack off so badly. She was getting harder and harder, as her balls started to twitch. John couldn’t believe it. Ms. Edwards had and cock as big as his but had to be two inches thicker. He only had seen a shemale on line and never believed them to be real. Now there was one just on the other side of this door jerking her cock. This made John even hornier, he couldn’t explain it but she was turning he on. John slowly dropped is pants and started to stroke his dick. Mary was going at it hard now, licking her fingers of one hand as she stroked the shaft of her cock. John’s cock was rock hard as he pumped away at it. Never had he seen a sight like the one in his short life. Her cock was so thick and her balls so clean, not one hair was there. Mary kept her area very well clean all the way back to her sexy asshole. Mary was going at it for some time now with her eyes close and moaning load. Stroking her cock and pulling at her balls, she never noticed John outside of her bathroom jerking his cock.
John could feel his cock grow as he was about the shoot his load all over the door frame.
“What do you think you are doing” came a voice from behind.
John could feel a hand now on his shoulder and turn to see who it was. For the second time today John was caught by his mother with his cock in his hand. Now this time Jennifer was not feeling sorry for her son being caught jerking off.
“What are you doing” she repeated herself.
“Uhuhuh uhm” was all John could say.
Looking Jennifer still doesn’t know what came over her, but she couldn’t take it anymore. She grabbed hold for John’s cock and dropped to her knees. She looked up at our son, licked her lips and drove her mouth onto his cock. She was so horny that nothing could have stopped her. She needed his cock; it was the only thing she was thinking about all day, since she saw it first this morning. Jennifer started to go deep on his cock, sending it all the way down her throat. John was in heaven now totally forgetting about Mary on the toilet stroking her own cock.
Back in the bathroom Mary was stroking her dick like never before. She was on the edge of cumming when she heard sucking noises and opened her eyes. She stopped jerking cock and just looked out the door to see her lover sucking the boy, that cause her to become so turned on, big cock. This was the hottest thing Mary had every seen, she got up and walked to them.
“Hey Jenny, what do I have here?”
Jennifer looked up to see her lover standing behind John rubbing his chest. John didn’t know what to do; this was too much for him. Jennifer on the other hand knew that this may be the only time she could have this naughty experience with one of her sons and her lover. Jennifer reached out and grabbed hold of Mary’s cock and stuck it in her mouth. She stroked John’s dick as she bobbed up and down on Mary’s. Then she would switch and suck John’s dick and jerk Mary’s cock.
John stopped thinking and just let his cock do all the work. He turned to Mary and kissed her on the lips. She returned the kiss and pushed her tongue pass is lips and into his mouth. With one hand John reached around and squeezed her ass that was so firm. Mary broke the kiss and whisper in his ear if he wanted to take this to a level of exotic high. With his mother’s lips wrapped around the base of his cock, he moaned out a yessss! Mary put a hand on Jennifer’s arm and bought her to her feet. She than lead both on them to her bedroom and pushed John on his back to the bed. Jennifer resumed sucking her son’s cock and Mary crawled her way up John’s body. She looked down at John and said that you don’t have to do anything you don’t want to. Just say the word and we will stop, we both want to make is enjoyable for you. “Are you ready” With and nod from John Mary lowered her cock to his mouth. Now John had never sucked or thought about sucking a cock before. He knew he was straight, but the high he was on at the moment made him open his mouth and welcome her cock into it. John’s mouth was not used to the thickness of her cock and he could feel his mouth being stretched from the size. He started to gag on the cock as Mary pushed her dick slowly into his mouth. After a couple of minutes John started to get the hang of it and started to work on her cock like any good cocksucker. As John sucked Mary’s dick, she turned and lower her mouth onto his and now they were in a 69 position sucking each other cocks. John never saw his mother leave the room and return, but as he was sucking Mary’s cock; Jennifer lifted his legs and put some cold liquid on and around his ass. John was too into the moment to know that Jennifer was about drive a pink strap-on into her son’s ass. Mary pulled her cock from his mouth and got off him but without removing her mouth from his cock. John looked up just in time to his mother enter his asshole with the dildo. Jennifer very slowly eased the pink dick into her son’s ass until it was three quarters of the way in. The pain was hardly as great to the feeling of his own mom fucking him in the ass. This was all new to John and he loved every moment of it.
Jennifer pulled the strap-on from his as and moved to the side so Mary could replace her cock in his ass. Before she put her dick in him, she had him roll over onto his hands and knees and get on the bottom of the bed. Mary now standing at the foot of the bed lined her thick cock up to his newly sherry popped asshole and slowly pushed inch by inch of her cock into it. After she was all the way and held it there for a bit for his ass to relax and take the size of her cock. She removed about half of it and slammed the whole thing back into his ass. Now picking up pace Mary want full on John’s ass, fucking it hard and deep.
“You like being a naughty boy, don’t you” said his mother as she position her ass in front of John’s face.
“Now be a good little boy and lick you dearest mother’s asshole.” “Lick it good and you will be rewarded nicely”
John drove into his mother’s ass licking away. It was a lot sweeter than he thought it would be. He licked and licked and pushed his tongue in her rose bud. He could feel her fingers hitting his chin as she fingered herself and he worked her asshole with his tongue, all the wild being fucked from behind by Mary.
“I want you to suck mommy’s cock now son as I suck yours” Jennifer told her son as she reposition herself under John.
Jennifer grabbed hold of John’s dick and pulled it into her mouth as John lowered his mouth to her pick cock standing upward to him. As Jennifer was sucking her son’s cock, she would from time to time stop and lick Mary’s cock as is slide in and out of John’s asshole. John knew he was going to cum soon and tried to hold off for a little longer. Mary was close too and knew were she was going to blow this load. She had John turn and rest is face next to his mother’s as Mary jerk and last to pumps on her cock and exploded all over John’s and Jennifer’s faces. John took some of his first cum into his mouth and licked some more off his mother’s face, it was salty but very good. When Mary was done she told John to cum in her ass, so John got behind her and pushed his cock in. He only got one good fuck and he emptied his balls deep into Mary’s ass. After Jennifer told him to lie back down on the bed and Mary crawled on top. Mary got her ass right above John’s mouth and told him to open. John did and Mary pushed all his cum out of her ass and into his mouth. Next Jennifer told John to come over and give some of the cum to her. John crawled to his mother and kissed her passing the cum from his mouth to hers.
“Wow!!!” John moaned out after finishing the kiss to his mother. “You too are the hottest chicks I have ever been with.” “I need to come over here and help you clean more often Ms. Edwards.
Mary sat on the edge of the bed rubbing John’s cock as it slowly went limp. Jennifer looked at Mary and told her that we need to get together like this again and if Bruce is packing what John is than there will be enough meat for everyone. Mary agreed with Jennifer let out a little moan as John was sucking the last bit of cum from here softening cock. With a pop John looked up at Mary and said that he could easily take Bruce into coming over for some hard labor…
To be continued.
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Sorry for the reduced content recently! I was sick. Should be all right again now 🙂
New feelings, new lifestyle, leading to a new lady-man partner dominating me….
My name is Ryan and I just finished up college, I was a bright, hardworking and had my whole life ahead of me.
Dress as a school girl and have sex with my two room mates
sometimes strangenessi s where the heart is
A prostitute gets kidnapped and finds love in the oddest of places
This is my second story so yeah it still kinda sucks, sorry it took so long to put on here I’ve been busy and stuff. Anyway, my apologies for any grammar mistakes and whatnot if you find any. And yes, I know it is still kinda short, the next one I make will be a lot longer. Please comment to tell me what is wrong with it so I can fix it in the future and stuff, thanks.
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As soon as I got done drinking her piss the door bell rang.
“You stay right here and I’ll be right back slave”
While she was gone I took a look around her house. It all looked pretty normal and not out of the ordinary. I also noticed the clock… 10:30 A.M!! That’s all?! It feels like 3 P.M! When I started thinking about how in the hell it is so early my mistress came back, with another chick! Well, I think so anyway. She could be another shemale for all I know. And she was just as hot if not hotter than Mistress Melissa!
“Slave, I want you to meet Stacy. She is going to be helping me make you our little play toy. So the same rules apply to her as me, got it?”
“Yes mommy I understand…”
“Good boy. Now please Mistress Stacy like you please Mommy”
Mistress Stacy began undressing as mommy sat down on the couch and began rubbing on her cock. Mistress Stacy was a shemale! I knew it! Anyway, she sat on the corner of the bed naked now and stuck out her leg.
“Greet me slave”
Wow, d? vu… I began kissing and sucking on Mistress Stacy’s toes and foot moving farther and farther up her leg. As soon as I got to her 9 inch cock I bobbed some of it down my throat and continued kissing on her body. When I got to her tits I began alternating between them suck and biting on her nipples, and they tasted great!
“Oooh yeees bitch suck on my nipples you little slut”
She pulled me up to her face and we started making out in the some-what passionate-like kiss. All I could feel was her tongue invading my mouth all over, and it felt great! But for some reason she pulled away.
“You certainly know how to please me slave, and I will give you a reward for your great job. I will let you fuck me if you start to call me your sissy instead of Mistress, deal?”
“Deal!”
“Good boy, now fuck me until you cum in my ass slave!”
Sissy bent over the bed and I had the most perfect view ever of her ass just sitting there begging for me to come and fill it with my cock. I started to slowly slide my dick in because her ass was unbelievably tight.
“Oooh fuck yes slave fuck sissy harder!”
As soon as she said that I just started pounding her ass with my cock going all the way in till my balls bounced off her cheeks and then pulling all the way out and slamming back into her, and she must have liked it from the way she was moaning.
“Oh fuck yes sissy I’m cumming!”
“Oh holy shit slave yeees goood boy! Oh my God yes! I can feel your cum hit the walls of my ass yeees!”
I squirted a couple more times and pulled out. Sissy bend over the bed with her cum filled ass and shook it in my face.
“You made a very big mess in Sissy’s ass slave! Clean it out or I will punish you!”
I got down on my knees so I can lick her easier, spread her cheeks, and started to dig in.
“Oh hell yes lick all of your cum out of Sissy’s ass you nasty little slut!”
She kept shoving her cum filled ass in my face harder and harder, and it actually tasted pretty good! But why I was having fun cleaning out Sissy’s ass, I felt something touch the tip of my ass. I looked back and say Mommy trying to slide her cock down my ass!
“Just sit still I know you like this slave”
It was a really tight fit and I could feel every single inch of her cock pump in and out of my ass and it felt sooo good! Once she finally got in all the way she just went wild in my ass, pumping in and out so freaking fast it was unbelievable!
“Oooh my fucking God yes slave! You are so fucking tight you little slut! Oh my God I am going to cum so fast! Holy crap I can feel every inch of your ass squeezing on my cock!”
Mommy just kept pounding at my ass for a few more minutes and then Sissy got up and turned around and shoved her huge cock down my throat face fucking me. It felt so good getting a cock rammed up my ass and down my throat at the same time I swear that they were going to meet each other inside me! Then by some weird coincidence both Mommy and Sissy started to cum inside of me at the exact same time!
“Fuck yes bitch! Swallow Mommy’s cock down your ass! Gobble all of your cum down my ass you little fuck slut!”
When they both finished cumming they pulled out of me and walked away and just left me there with cum dribbling out of my mouth and ass.
“We’ll be back in a few minutes slave…”
I just sat there and wondered what they were going to do next… I waited for maybe 10 minutes until they both came back, and they had a dog with them… Oh God, I don’t think I like where this is going…
I have thought about bestiality before but never on me… I hope to God it’s going to be for them and not me, but I’m probably wrong….
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Leslie and Cal two people alone find each other and begin an affair
Little Lisa
(…in a world that isn’t but ought to be…)
Chapter Two
Lisa ran the last 3 blocks to school. She hadn’t taken the time to put on her panties and her little prick bounced up and down beneath her skirt the whole way. She’d hoped some park perv would’ve sucked her off but the fat old man didn’t seem to have much interest in her tiny uncut prick. She tried to remember how many times she’d jerked it up hard listening to her mommy getting ass-fucked last night but it was all a blur… she hadn’t shot her load then and she hadn’t shot it since and her little cherry balls felt like water-balloons.
A carload of High School boys passed yelling obscenities and gesturing out the window but she paid them no mind. Mr. Dexter was out watering his flowers like usual with his fly open and his prick poking out like a dog’s wet nose but she just smiled and waved and kept running. The school bell rang before she got there… she dashed up the steps and burst into the first floor girls lavatory. A bio-girl named Nanci was leaning against the sink puffing on a cigarette. She took one look at Lisa and chuckled.
“Who’d you blow?”
Lisa looked in the mirror. A flaky crust of dried cum streaked her jaw and forehead and her hair hung in thick stiff strands… the old man had wiped the last of the cum out of his pubes with it.
“Hold it..” Nanci said reaching over plucking a long grey pube off Lisa’s cheek. “What’s this? A souvenir? And look at your hair girl… ugh! It smells like some guy’s dirty butt..”
Lisa grabbed a handful of hair and smelled it… she started to cry. Nanci quietly put down her cigarette, wet a paper towel and sponged it through Lisa’s hair and told her to clean her face. Lisa was mortified but touched at the attention. Nanci was a grade older and Lisa didn’t know her that well. She blushed and washed her face.
“A-ah needed lunch money.”
“I guess you did. Where’d you go, the park?”
“Un-huh.”
“Were there many pervs?”
“Just one, a fat old man..” she started but Nanci finished her sentence “..’with long grey pubes who stuck his short fat dick in your mouth and pumped his cumload all over your pretty face and hair’. Ever notice how much cum pervs pump out?.. why their cumloads are always so big?.. it’s ‘cause they’ve been jerking on their cocks for hours, maybe days without unloading before they find some sweet little nasty slut to spurt it on. Nothing like bathing in a 5-day load of perv jizz to overwhelm a gurl..” She giggled and took a last drag on her cigarette and tossed it into the toilet of an open stall. “C’mere..” She dried Lisa’s face and ran a brush through her hair and helped her with her makeup, even loaning her eyelash brush. Lisa was thankful for the kindness… she was already 10 minutes late to her first class.
Nanci was a Puerto Rican/Greek mix bio who’d started puberty early. She had creamy brown skin, yummy pear-shaped tits she liked to show-off at the slightest provocation and thick black wavy hair that hung to her shoulders and jounced when she walked. The only thing marring her young exotic beauty was a big Greek nose that jutted out of the middle of her face like a beak.
“Papa says for my 16th birthday he’ll pay for a nose job,” she’d say. “I don’t know whether to believe him or not… he likes shooting his cum up my nostrils too much..” and she’d open her eyes big and snort and pretend to gag then buckle over with laughter.
She had an unruly tangle of thick curly black pubes that she complained about all the time, saying how she had to shave it every day because her Papa and brother hated lapping their tongues on stubble. She’d lift her skirt and pull her panties to the side showing all the girls gathered in the lavatory her swollen stubbly light-brown cunt.
“Look! Can you believe I shaved it just before bed last night? What a hassle..” she’d groan.
Lisa liked her. Most bio-girls were so two-faced about their sexual experiences, and they were all a little snotty about tranny gurls, sensing a strange competition they had no control over. But not Nanci. She didn’t have any qualms about sharing every detail about her sex life, and age and grade didn’t matter to her a bit, she never pulled rank on any girl no matter how old or how experienced she was or what she had between her legs. She understood what was expected of a young slut and happily delivered the goods without a fuss. That’s why she was a favorite with her teachers and always got good grades whether she studied or not. If she needed an ‘A’ on a test she’d go to her teacher’s office after class and earn her ‘A’ on her knees or bent over a chair.
“There! You look almost presentable..” she giggled. “Your first period teacher is Mr. Richards, isn’t it? What are you gonna tell him?”
“I don’t know! He’s sure to make a scene about it,” Lisa fretted.
“Where do you sit?”
“Front row, a couple of seats to the side of his desk.”
“You’re one of his bridesmaids! No sweat girl, he’ll make some rude lewd comments, he always does, it gets his dick hot and puffy… keep your panties in your purse and flash your pretty clitty at him every chance you get, don’t worry, he’ll quiet up quick. I had Mr. Richards year before last… he’s a major panty-pervert and basically harmless, likes staring at all the girls crotches and beating off into a pair of dirty undies after class… his top drawer is full of them, all stiff with his cum! I gave him a pair of my panties right off… I wore ’em for like two weeks solid so they’d be nice and smelly and caked with pussy ooze, he likes that a lot. He sat me in the front row too and I gave him split beaver shots every single day. Unless he’s gotten more depraved and daring that’s all he really wants. I sailed through his class with an ‘A’ and didn’t have to suck him off or anything, not once! ‘Course, sitting there everyday with my hairless pussy pie open to the breeze wasn’t exactly fun in winter… my cunt ’bout froze!”
Nanci seemed so worldly, so wise. The two of them had never spoken more than a few words to each other and Nanci wasn’t really a member of Lisa’s group of friends. She was a loner, kind of a free agent. Sometimes she’d hang with those in the bleachers for a day or two then float into the orbit of one or another of the main bio-girl groups. But she didn’t seem to fit in with them much either… most of the bio-girls were phonies and back-biting liars and Nanci didn’t mince words and she didn’t suffer fools. So she floated from group to group and stayed by herself a lot, which seemed to suit her just fine.
“Say gurlfriend, are you wearing padding or are you budding real boobies?”
Lisa looked down at her blouse. The top button was undone giving Nanci a clear shot of her loose trainer and tiny breasts.
“My mom’s been giving me estrogen. My boobs just started growing a few months ago.”
“Nice! How’s your ‘package’?”
“My what?”
“Your cock and balls, hon… how’s your sausage and meatballs?”
“Okay, I guess. It tingles and gets hard all the time.”
“You spurting yet?”
“Un-huh… lots!”
“Oh yummy! Show me!”
Lisa hiked her skirt up to her belly-button. She was all a-twitter hoping Nanci might want to wrap her voluptuous Latin lips around her stiff little prick and suck it… it’d only take a pull or two for Lisa to start spraying cum like a firehose. Nanci squatted in front of her and peered intently at her tiny dangling piece of pink meat… she didn’t say a word, she just stared at it this way and that. Lisa flushed red and and her cock started to tingle and swell… no girl had ever made her stand at attention while they stared at her clitty like that. She laughed nervously and Nanci looked up.
“What??” she asked.
“I just realized it’s easier showing my clitty to some pervert I’ve never even seen before than you..”
Nancy smiled and stroked her fingers along Lisa’s swollen shaft tip to balls. She rubbed her little cherry balls and peeled back the foreskin and tongued her piss-slit deep, then swallowed Lisa’s cock whole and drew off it slowly with her lips clamped tight. Lisa groaned and shivered and her legs started to wobble… she grabbed the sink counter with both hands to keep from crumpling to the floor. Nanci’s hands danced warm up the back of Lisa’s tender thighs and clutched her plump round cheeks and opened them wide.
“Umm… such a nice soft ass..” she cooed rubbing her hand up and down in Lisa’s moist crack. “Can you see in the mirror?”
Lisa turned enough to see the light brown up her deep crack turn to hot pink around her bulging hole and it was puckering in and out and she realized she was hyper-ventilating. Lisa thought her knees would buckle as blood rushed hot to her cock.
“Umm… such a responsive young gurl… with such a nice plush ass..” Nanci cooed. She kneaded Lisa’s butt cheeks slow and cat-like before giving them a burning slap. She flicked her tongue at Lisa’s balls then glanced up at her impishly with her mouth poised open. Lisa’s little dicklet quivered and sweat broke out on her forehead as Nanci circled her tongue round and round the tip. Lisa was sure she had a quart-load of cum to spray strait down Nanci’s throat.
“Works just like it should..” Nanci said with a grin and rose to her feet. “Tastes good too, your precum is yummy..” She looked into Lisa’s eyes for what seemed like an eternity gripping her tiny stiff prick. “Bet you thought I was gonna suck you off, didn’t you?” Lisa blushed and stammered a response.
“Ah… I was k-kinda hoping..”
“It’s verrry tempting hon, but I already swallowed my Daddy’s load before school and I’m due to swallow Mr. Jenkins load in 15 minutes, and that’s before lunch! No wonder I’m putting on weight! Maybe we can work out a trade. I just love having my ass eaten real deep..” she said with a wicked grin, then added “You’re going to be very popular with the boys AND the girls Lisa..”
Lisa beamed. Nanci gave her pulsating cock one last squeeze and let it go, then bent over the sink and checked her makeup in the mirror. Lisa’s head was swimming. She knew she was in the lavatory but she wasn’t sure why. When she came to her senses and glanced in the mirror she was still holding up her skirt with her little prick sticking strait out. She was sure she’d never make it through Mr. Richard’s class without it spurting hot cum like a volcano. She dropped her skirt but her prick still pushed out the fabric. She lifted it again and smiled hoping Nancy would take pity on her and pull her into a stall and suck on it a little more. But Nanci wasn’t interested, she just stared in the mirror arranging her hair and practicing coy young girl glances. She covered her lips with bright red lipstick, rolled them together and pooched them out.
“Time for me to earn an ‘A’ for this afternoon’s math quiz. I’m on ‘pay-forward’ with Mr. Jenkins..” she giggled. “Don’t forget to clean your knees..” she said and sashayed out the door with her skirt swaying. Lisa heard the click-click-click of her half-heels receding down the empty hallway outside.
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TT (?)
I had a secret, I wanted to be with a tranny. A shemale. A ladyboy. A chick with a dick. I don’t know why, but it’s something I wanted to try. Don’t get me wrong, I’m not gay and I didn’t want some guy wearing lingerie. I wanted someone I could believe was a legitimate woman, who just happened to have a dick. So here’s the story of my exploration.
(I had a membership with an adult “dating” site. I wasn’t too serious about it, mainly just used it to watch videos and look at pictures that I could believe came from a real person. I had traded emails with one person on there, she was a very large black woman. She also had huge tits. I never met her but we traded lots of text messages, mostly sexual in nature. We talked a lot about how she would love to be the first to make me fall in love with the so-called chocolate pussy, and how much she wanted my white chocolate cock in her ass. We even explored the idea of buying her a strapon and having some deviant fun but the time was never right. One night she texted me, she was horny, and wanted to cum but couldn’t go anywhere. I asked her what I could do, expecting some sexting and pics of her masturbating that would get us both off. Instead she sent me a message telling me to jack off thinking about her and send a picture of me cumming. This was a new level for me, and I wasn’t sure how to get the pic at first, but I finally figured it out. So I sent her the pic as soon as I had it, soft dick in my hand, and cum all over me. By the time I was cleaned up with my shorts back on I had a reply. She said I was a good boy, and she came really hard seeing my cum shooting up out of my hard dick like that, imagining I was shooting on her tits. She attached a pic of her licking her huge glistening dildo, I jacked off to that later. Maybe we would have to make the time right some day. But that’s a different story, and I need to stop rambling and get back on track.)
So, I had finally decided I was going to start looking at the *tranny* section, and when I did the results covered the spectrum. From gay guys who figured they had a better shot advertising there, to “women” wanting relationships with straight men, only 1 dick in that relationship. I clicked around for a while, exploring what was out there, and finally started sending emails. I would tell them that I was a straight man looking to experience a shemale. I got a few “thanks but no thanks” replies, and more than a few of my emails were never returned. However, I did get some positive replies, mostly from crossdressers, but a few from the “gifted” women I sought. I did trade some emails with a few of the crossdressers, their talk of being balls deep in a straight ass did turn me on a bit, but mostly we chatted and they jacked off to me.
One day I logged in and saw I had a message from a member with private settings, I never emailed then. But when I clicked on the message I saw she had attached pictures along with a message expressing interest in being my first experience. She was stunning, blonde, nice big tits, and an ass that would take your breath away, exactly what I was looking for. She was wearing panties in all of the pics and seemed to enjoy hiding her secret from me.
We chatted for a few weeks, trading some more pics, but I never did see her take the panties off. And from the frontal shots I was starting to doubt her credentials, but either way I couldn’t stop now. Within a couple days of the first text we were texting each other all day, talking about all sorts of things, sex talk fell by the wayside for a while.
A few weeks later I had a unexpected day off, on a Friday even. This was unprecedented for me. I texted her in my excitement, and without thinking accepted her offer to come over that evening. I even went out and bought a gallon of juice, supposedly the pineapple made cum taste better, I wondered if she was doing the same. As the hour grew nearer I started to realize what I was getting myself into, and it showed in my texts. She asked if I was freaking out, and when I replied that I didn’t think I could touch a cock or ass, much less return any pleasure she reassured me we would take it very slow, and no reciprocation was necessary. So I packed an overnight bag, including extra condoms and a small bottle of lube, just in case, and started getting ready.
I knew she liked hair on a man, just not a hairy dick and balls, she didn’t like hair in her mouth, so I trimmed back the undergrowth before hopping in the shower. She had gently asked me to make sure my asshole was clean, out of politeness, and I understood and hoped she did the same. Squeaky clean I got out and dried off, then pulled on the clothes I had picked to make a good impression. Boxer briefs to show off my package and ass when the jeans that did the same came off. Leather belt to add to the suspense when she sarted undressing me, and a semi-tight t-shirt/A-shirt combo to accentuate my upper body. All on top of my cleanest pair of boots and topped off with a light spritz of cologne and my Mossy Oak hat.
I pulled into her driveway with just enough time to take a deep breath before grabbing my bag and going to the door. She opened it just as I got there, and she was simply gorgeous, she obviously put even more effort into the first impression than I did. I stepped inside, saw the shoes lined up and took off my boots as she took my bag and set it aside. With the boots off she was a bit taller than me, and I stood there unsure what to do until she took my hand, spun me around, sighed deeply and then led me to the couch. She explained that she hadn’t planned dinner for another 45 minutes so that we would have time to talk and get me comfortable with her. She complimented me on looking nice, and I did the same, blushing a bit the whole time.
We sat on the couch quietly for a few minutes, me fidgeting nervously and her running her eyes up and down me. Finally she turned on the tv, a good sitcom was showing, and snuggled into my chest. I was frozen until she pulled my arm around her shoulders, putting my hand on her breast. It was firm, the nipple was hard, and through the T-shirt I could tell it was very soft, I started to get hard, and my jeans started getting a little tight. She must have been waiting for it because she started stroking my cock through my jeans, running her fingers from bases to head and back, feeling the girth, and playing with my balls a bit. We sat there like that until the show ended, and all through the next, I was still too nervous explore the rest of her body, and she didn’t want to rush anything. As soon as the credits rolled on the 2nd episode she squeezed my cock and bounced up, exclaiming that it was time for dinner. She swayed over to the fridge, and offered me a beer which I gladly accepted, but before she handed it to me she explained her rule about drinks: Before each drink you had to remove an article of clothing. I agreed to her rules and, feeling bold, pulled off my T-shirt leaving me with my undershirt still on. With a nod of approval she handed me my beer and grabbed one for herself. She popped the top and moved to drink but I stopped her and reminded her of the rule. She giggled and winked, saying she was just testing me, and did a little dance as she pulled off her socks then took a swig of the beer. She set her beer down and handed me 2 steaks from the fridge, corn on the cob in foil, along with salt and pepper, she took the spatula and a large plate as she led me out on the porch to a charcoal grill. She started the coals as I opened the steaks and sprinkled a dash of salt and pepper across the tops. While we waited for the coals to finish we both finished our drinks, she went in and got 2 more before reminding me of the rule. Not wanting to completely reveal the major erection I had I pulled off my undershirt, with a wink she followed with her shirt giving me an amazing view of her D cup tits sitting in a half cup bra. My jeans were suddenly getting very tight.
The coals were ready by now, so I stepped up and laid the steaks and corn out with a sizzle, as she moved behind me and started caressing my body. Her hands roamed up my arms, over my shoulders, down my back and back up, around to my chest and down to the bulge in my pants. She gave my hard cock a squeeze while whispering in my ear that she couldn’t wait to taste it and my cum after she felt it deep in her ass. I had to concentrate very hard on the steaks to keep from ruining dinner. Then her hands moved around, grabbed my ass, and she whispered that she would love to be inside my tight firm ass if I would let her, strangely my dick jumped a little at this. She only stopped exploring my half-nude body long enough to drink her beer. We both finished our drinks just before the steaks were done, and carried in the food and trash, she set the table while I unwrappd the corn and washed up.
When I came back from using the bathroom she was drinking another beer and holding one for me, but she hadn’t removed any more clothing. I mentioned this and said that I shouldn’t have to strip as a penalty, she countered that I agreed to the rule but she would give me a lap dance after dinner. I could tell she wouldn’t budge so I pulled off my jeans and sat down beginning to serve the food, she had put our plates beside each other on the table. She set down her beer, reached around behind her and her bra dropped to the floor. I stared as they bounced, sagged slightly, and settled on her chest. I could tell they were fake but they were just the right amount o firm and perky with a real looking sag and bounce. Amazing. She laughed at my expression and sat down, crossed her legs and relaxed as she said it was my turn. I sudenly realized I only had two more articles of clothing before I would be nude, I grinned as I had an idea. I went back to the bathroom, and took off my boxers, walking back in just my jeans I tossed them to her. She laughed and said we should eat before it got cold.
We ate fairly quietly, our mouths were busy chewing, but we stared at each others bodies the entire time. I was captivated by the slow rise and fall of her tits, and how her nipples were hard from the attention. She split her attention between my shirtless torso, and my still, for now, clothed groin. By the time we finished our meal we both realized how silly we looked and laughed for a good 5 minutes. We cleaned up the table, and she grabbed another beer, I held out my hand for one but she said none for me, if I had anymore I would have a hard time getting hard enough to fuck her face and ass. I nodded, and asked if that was the case should she be drinking, she asked if I really wanted her to be hard, I nodded and said I wanted it all. She smiled and said that a big hard dick being shoved down her throat and up her ass always got her hard. I smiled and asked which piece of clothing she would be taking off, she told me to go wait on the couch and I’d find out.
Once I sat down I heard her voice frm the kitchen telling me to find something on tv, and once the tv was on she turned off the lights. I surfed around and saw that she had some porno channels, I found a good one with two hot trannys fucking a chick. She must have seen what I was watching because she laughed and told me not to jerk at all, she didn’t want me cumming without her. I sat there for a few minutes watching the chick getting railed hard by two dicks, when I heard a noise and looked over to see Teri crawling towards me wearing nothing but some black lace boy shorts. She crawled between my knees, and started licking my nipples, working her way down my body and opening my jeans until she wrapped her lips around the head of my cock. I groaned in pleasure, after all the build up the warmth and wetness of her mouth was amazing. As she started taking me deeper she pulled my pants all the way off, when they came off she deepthroated my dick, her tight throat almost made me cum but I pulled her head off and sat there panting. She looked hurt and asked what she did wrong, so I told her that I had to stop her or I would have came, and I didn’t want to yet. She giggled and said that if I was going to enjoy tonight I had to let her be in charge, then she swallowed my cock again. As I watched her bobbing up and down, twisting and pulling her nipples, I came, she swallowed all of it but the last squirt, which she held in her mouth. When I was done and she had sucked the last drops out of me she stood and turned around, pushed her panties down, and sat next to me. I looked over and smiled, her cock was just above average in size, completely shaven, and somehow looked very feminine. While I was staring she spit my cum into her hand and started jerking her cock with it, I was speechless. She saw my expression and laughed, then said that any minute now I should be ready to go again, this time deep in her tight ass, the beers were a special brand that reduced the time between orgasms, and increased semen production. She sighed and said that now I could give her hard cock and big creamy loads all night long, and sure enough as I sat there watching her stroke her cock mine grew hard again, she fondled my balls and told me they were just as big as last time. I asked her what would happen if I had another beer, and she said that my cock probably would stay hard and my loads would get bigger. Her voice trailed off as she scampered into the kitchen, returning with an open beer, while I chugged it she led me up to her bedroom and bent over the bed wiggling her delectable ass.
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“You’ve just go to remember to let the right one in.”
Suzy learns how hooked she is
This is my first story. Hope it’s good.
Young Boy Dreams to Become Women
Ever since I could remember Dave and I were friends, we were like brothers and we spent a lot of time together. My parents were both doctors and always worked long odd hours. Which meant I would be home alone most of the time from the second I was old enough.
Once dave and I started high school things were different I basically moved into dave’s house his mom Katharine insisted at least during the school week and I didn’t mind. I mean you don’t say no to a woman like Katherine.
She was a rather tall at 6”2 for a woman, which wasn’t surprising dave was 6”4 and she had this hour glass figure that made her 42dd tits and robust ass manage to look even sexier. But it was all trumped by her beautiful face and olive complexion, she was sent by god and ooo boy was I grateful.
I had moved into dave’s house in freshman year of high school and it was great his mom was the best she had always treated me like a son, she gave me something that for most of my childhood had been missing. As for dave’s dad we don’t really know what happened to him whenever dave brings it up she swells up with tears and leaves the room. He never investigated futher.
About half way through senior year is when it began dave was an above ordinary sport talent and college scouts had been visiting the house for some time. Katherine and I all though pleased we didn’t want to see him go away to school. Dave was the smart one I had gotten into the local community college and planned to live with Katherine for the rest of my life, trust me once you saw her tits and ass you would be hypnotized to.
Dave was leaving town he was going to spend 2 weeks visiting schools around the U.S. I on the other planned my break to be pool side in dave’s backyard. But what these 2 weeks had in store was beyond my comprehension.
I came back from the airport with Katherine we had dropped dave off. When we got inside Katherine went to go change and I told her id hop in the pool for a quick swim. I jumped into my trunks and was chilling in the water before you could blink.
While I was floating around I looked up at Katherine’s window she was top less her massive perfectly shaped bouncy tits were free. My 5 inch dick swelled from the sight I hoped she didn’t know that I was looking at her. Still in the pool I stroked my cock for a couple of minute cuming all over my swimming trunks.
I cleaned up and hurried up stairs to my room, Katherine was still standing by the window, I just couldn’t see the smirk on her face. The rest of the night went on without a hitch dinner was nice we talked about the day she obviously missed dave.
That night I went to sleep thinking about the marvelous tits I saw before I wanted to see them again. I pulled out my dick and started jerking off again dreaming about Katherine. I thought I had heard something by the door so I quickly stopped and went to sleep smiling through the night thinking about those magnificent tits.
The next morning I woke up a little later by the time I crawled out of bed it was almost noon still sporting my morning wood I stumbled to the bathroom but the door was locked. I knocked and I heard her from inside “one second sweetie” I waited dancing from having to pee so bad still not comprehending that I was fully erect waiting for my best friends mom to get out of the bathroom.
She finally opened the door and walked straight into me poking her leg through my shorts. A little embarresed I took 2 steps back and i noticed she was staring at my dick I blushed said “im sorry” and scurried by her to pee. I didn’t even realize she was in a sexy bikini her ass barely fitting inside and her tits like wild animals couldn’t be contained.
After my piss I cleaned up changed and made my way to the kitchen for a bowl of cereal. Katherine was outside cleaning the pool she looked so hot standing there the sun glistening off of her perfectly shaped body. I quickly ate and changed into my swim trunks which still had some residue from yesterdays incident in the pool.
When I got out there Katherine was laying down sunbathing her bikini straps were undone. She called me over “would you be a dear and put lotion on my back?” I stuttered my eyes fixated on the undone bikini straps, I caught my self and quickly said “sure”.
As I massaged the lotion into her back I could feel my cock coming to life, I thought to my self ooo god why now seriously. All of a sudden I felt a hand wrap around my dick. Holy shit what was happening she lay there on her stomach slowly playing with my 5 inches, she didn’t move or say anything I didn’t know what would happen next, i continued to massage and so did she.
I was starting to lose control her massaging my cock was driving me crazy when the convulsions stopped I had cum all over my bathing suit again. She finally rolled over tits fully exposed right there infront of me perfect in every way. She giggled “I know you’ve been dying to play with them.” She was right I had been since I was 6 years old and met her.
I just smiled shyly and moved away, I had never been with a girl yet alone a woman, lets just say im more of a playboy penthouse kinda guy. Even though I dabbled in some kinkier stuff like some BDSM porn and even some Dominatrix stuff I was still pretty useless around women.
Katherine smiled so softly and asked me “what’s wrong havn’t you ever seen a real woman’s tits in person?” she grabbed my arm forcing me to take a tit in my hand. She was much stronger than me and my small weak frame not that I put up much force. As I massaged her tit I grew more and more curious I moved my other hand in to play with her other tit.
I was playing with her nipples massaging her tits it was a dream come true. I moved in the my tongue sucking her hard pointy nipples swirling my tongue. She was moaning loudly now and I was harder than ever before.
I went in for a kiss and she grabbed my head and shoved her tongue down my throat kissing me ever so passionately. I knew I would never be able to say no to her, if I did she could just over power me but that was beside the point that I wouldn’t want to say no to her.
I continued kissing her and playing with her tits for minutes her skin tasted so good and her lips were soft and smooth. She finally stopped and looked at me she asked “do you wanna go for a swim in the pool or for a swim in my bed upstairs?” I didn’t know how to respond for the past life time I had been thinking, dreaming about this moment. “the pool first” I retorted.
She smirked at me “ok have it your way” and without hesisitation jumped into the pool. I ran after following her in, we met in the pool embracing for the first time with our full bodies. She took me into her arms they felt so strong and safe it almost felt weird like something was different.
We continued floating around when she looked me square in the eyes her arms wrapped around my waist. It was something she had hid from me and dave for sometime now “dave is adopted, and im not a hundred percent a woman”. Slightly taken back by this I tried to push away but her grip was to tight “let me go!” I demanded.
Before I could think about what was happening she picked me up out of the water I was only 140 pounds and scrawny. She covered my mouth and sat me down on her lap, “im not going to hurt you sweet heart I love you like son. But you showed me yesterday when u jerked off to me in the pool that you loved me differently. So now ill show you how I love you.”
I was still flabbergasted by her comment “but what do you mean a hundred percent woman?” that’s when she took my hand and lead me inside I was so confused. We made our way to her bedroom where she sat me down on her bed and stood in front of me still half naked her tits hanging their in all their glory.
She turned around showing me her amazing ass and started to take off her bikini bottom was this it would my dreams come true not only would I have sex but it would be with dave’s mom, awesome. As she bent over I thought I saw something drop from between her legs but I couldn’t make it out but didn’t think twice her ass had me hypnotized.
As she turned around she said “this is what I meant by not a hundred percent.” And there it was Katherine had a dick a huge dick actually it must have been atleast 8 inches soft holy shit what had I gotten myself into.
I squirmed back onto the bed but before I could do anything she had grabbed my ankles and pulled me closer. I was torn on the one hand its my dream come true but on the other hand now she had a cock that was atleast twice as big as mine if not bigger.
She pulled in closer easily discarding my bathing suit her dick hanging there, “don’t be scared I wont hurt you I promise” I didn’t believe her “its ok sweetie we can go slow” and with that I was in the air she had picked me up I wrapped my arms and legs around her as an instinct, and that’s when I felt it between my ass cheeks it was big and warm comforting almost I wanted it to stay there I felt safe strangely enough.
She lay me down on the bed and kissed my neck and my lips her passion felt raw and I was enjoying the feel of her now semi erect cock by my ass it felt phenomenal. She whispered in my ear “do you like what im doing love” her cock resting between my frail small ass cheeks, I knew I didn’t have a choice in the matter “I do love it maam it feels good keep going”.
With that she had her cock right next to my mouth “open up” she said without a thought I opened my lips and slid her thick semi hard cock in to my mouth. Inch by inch she worked her cock into my mouth without saying I willingly accepted it. Her snake tasted salty and sweet her cock was like an amazing lolly pop salty and sweet. I swirled my tongue trying to fit as much as I can in my mouth.
Her hips swung more ferociously I was deep throating her 11 hard inches were tickling my throat, it felt so amazing. I was loving my first cock I wanted more I wanted it other ways I was lost in the pleasure of the moment.
She pulled out of my mouth and looked into my eyes she had that look. She kissed me on the lips again I could feel her cock pressing against my stomach, my cock throbbed to a hard on but there wasn’t time for my dick now there was this amazing snake in front of me that I wouldn’t have thought of more than an hour ago. I wanted it inside of me I wanted to feel it I rolled over shoving my ass into the air displaying it for my new lover.
She patted my ass caressing it and stopping in between my cheeks to massage my ass holver e it would pucker and twitch at her touch. I wanted her dick I wanted to feel it in my ass I moaned to her touch and pushed into her finger as it came closer to my hole “give it to me! Just give it to me!” I demanded. “no no love your not quite ready for me yet”.
She reached into her nightstand pulling out a 8 inch dildo. With my ass still in the air she positioned my head between her legs she took out the lube and moistened up my hole she put her dick in my mouth and I immediately went to work and so did her dildo it felt so good in my ass. Both of us were moaning so loudly now her cock in the back of my throat and my ass hole blooming to her dildo.
After about five minutes of this her hips were spasming with each swirl of my tongue around her shaft. Her hips buck and I tasted her sweet cum for the first time it was like a rush of excitement. Her legs wrapped around my head and she forced her cock all the way in the cum rushing down my throat.
I pulled my mouth away and made sure I liked off any remains from her dick. As she pulled her dildo out of my ass it was still blooming gaping with excitement in hopes of what was next to come. But she rolled over and put her arms around me “it’s a good thing Dave is gone for two weeks and it’ll be just the two of us”. It was music to my ears we spent that night wrapped in each other I felt so warm and comfortable in her arms.
When we woke up the next morning I was exhausted and my throat hurt slightly from the night before and my ass was a little sore. I thought she was still asleep but her smile told me differently, her hand grabbed my ass and I felt her nails dig in “you know your ass belongs to me now dear don’t you.” I smiled it was a dream come true.
We showered and spent the day by the pool but that’s another story.
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