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ashtonboi99 · 3 years
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“Is making love to me really like being with a girl ?” he asked
“Your body is soft and petite and curvy, your demeanor and body language is very passive/receptive, which could also make you a bottom if it weren't for how small you are down there. Also I can tell you love the foreplay, kissing and fondling etc. And you love being eaten out. Even your sounds are feminine… and of course, your attire.” The matter was settled
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ashtonboi99 · 3 years
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Ashton came by to see his new friend Karl after school. When he arrived, Karl was relaxing by the pool, wearing only a pair of modest trunks and displaying his muscular body.
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“Hop in,” shouted Karl.
“I’d love too,” Ashton replied, “but I don’t have a bathing suit.”
“I thought of that!” Said Karl. He grabbed a little pile of fabric and sauntered over to the meek sissy boy. Karl flashed his handsome smile and said, “this will look great on you.” Ashton looked at what he had been handed, confused… it was a girl’s two piece bikini! The boi turned bright red, and Karl just smiled. “C’mon… no one will see… it will be funny.” Ashton couldn’t resist doing anything that tall, strong, handsome boy asked. He slinked to the changing room, embarrassed, but also thrilled that Karl was paying attention to him.
“Karl?” He asked sheepishly a few minutes later, “I need help!” Karl poked his head into the changing room. Ashton has standing there, wearing nothing but the bikini bottom, and clutching the top in front of his chest. “Can you tie it?” Asked the little beta boi. Karl smiled and walked around the boi and tied the back of his bikini top. The boi was tiny, smooth, and with just the right amount of curves. Ashton didn’t have the bony body of a teenage boy, he had the smooth, curvy body of an adult woman. Karl placed his strong hands on Ashton’s hips, and Ashton exhaled, leaning back against him.
“You look gorgeous,” said Karl, and he gave Ashton a little kiss on the neck. Ashton’s entire body turned red at the feminine treatment, but he loved it and it felt so unexpectedly natural. Karl rubbed his hand gently across the front of Ashton’s bottoms. “Mmmm” he murmured in approval. He turned the boi around to face him and planted a firm kiss on Ashton’s pouting pink lips. Ashton melted in Karl’s arms, receiving the kiss exactly the way a girl would.
Suddenly, Karl scooped up the petite angel in his arms and carried him to the pool. Ashton giggled and cooed at how strong Karl was.
To be continued…
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ashtonboi99 · 3 years
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Mike liked his outfit, but he was uncomfortable not having any pockets. He had to leave his wallet and phone behind, he would be almost totally at the mercy of his date! But Adrian said he would take care of everything, and he seemed so sweet and gentle.
The feeling of the leggings against his freshly shaved legs was exhilarating, ad was the anxiety of going out in such a feminine outfit. But Adrian said he liked femmes, and Mike wanted to please him. He hoped the sweater and legging combo was feminine enough. He would be happy to become more feminine, but didn’t want to go overboard at first.
He looked down at his flat crotch again, debating about stuffing. If Adrian really liked femmes, then the flatness wouldn’t be a turn off…. But presumably he expected Mike to have some kind of a bulge… even a little one. But Mike’s never had a bulge, even in these tight leggings that left nothing to the imagination. His legs looked so slender and feminine, and his bottom was so plump. All those ballet classes had really given the boy a feminine shape.
Thinking about Adrian was already making Mike’s clit wet. He was glad he had put a sanitary pad in his panties! He was a little sad that he couldn’t wear a tampon on his date, but he wasn’t sure how he would explain that to Adrian, if things went that far.
The boy powdered his face, put on his lipstick and mascara, and coiffed his androgynous hair. He was a vision of femboy gorgeousness, and he was eager for Adrian to get him pregnant tonight
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ashtonboi99 · 3 years
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Jasmine’s punishment was to wear a panty liner to remind her she was a real girl.
Buying it was humiliating, and figuring out how to actually wear it was confusing and humiliating. What was surprising m was that it didn’t really bother her once she had it on. It reminded her of when she stuffed Kleenex in her panties to absorb her excess precum. She was slowly beginning to understand that she really was a girl who dressed like a boy.
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ashtonboi99 · 3 years
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This week Ashton can wear panties every day, shave and moisturize her legs with scented lotion, and practice doing her makeup. She can also find a youtube tutorial about makeup to learn new techniques. Girls love doing that.
Touch herself however she wants, but only through her panties. She can only call her private parts her clit or pussy and has to sit down to pee.
And she has to wear a bra and send Daddy a picture of her cleavage every day
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ashtonboi99 · 3 years
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Ashton felt.... strange. Here he was, an ostensibly cisgender boy, wearing a binder and a packer, like a trans boy.
The packer felt wonderful. He had special FTM underwear for it. The packer slid into a pocket in the front, effectively replacing his own, small penis. The packer was the smallest size available, but at 3.5 inches, it was still larger than his own little penis unless it was fully erect, and even then it was close. His balls felt a little pinched by the underwear, but other than that, the whole thing felt pretty cool. He had a bulge for the first time, and simultaneously had confirmation that his own sad little member was not a real dick. He effectively had to sit down to pee, which he usually did anyway.
The binder was another matter. It was tight and uncomfortable, even though he barely had breasts. He couldn’t forget he was wearing the binder, not even for a second. And he was constantly concerned someone might see it. If a stranger saw it, they would clock him as a trans boy. If it was someone he knew, the situation would be even more awkward. He couldn’t take his shirt off, which meant a whole lot of activities were now off the table.
The whole experience was awkward, embarrassing, and uncomfortable, but he loved every second of it. Only his Daddy knew his little secret, which made the whole thing even more exciting.
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ashtonboi99 · 3 years
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Adrian was behind the counter when the twink boi came in.
He had come in every day this week! He would order a drink in his soft voice and smile at Adrian, blushing. The boi definitely had a crush. Today he wore a little hat over his perfectly coiffed hair.... clearly overdressed for coffee, he had a thirst for something else.
Adrian wasn’t sure of the boi’s name, or even his pronouns. It could actually have been a lesbian, or a gay boy, or maybe a gay trans boi... or a lesbian trans girl... all Adrian knew was that they presented like a tomboy and he wanted to fuck any hole he could find.
He also knew that the twink boi now had a bulge, and had not had one yesterday...
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ashtonboi99 · 3 years
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A boi and a princess
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ashtonboi99 · 3 years
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Adrian looked at his Princess, proud of her. When he first met her, she was attempting to pass as a boy, and failing. Her masculine ego had been overcompensating for so long, she didn’t know any other way. Then one day he slipped a buck sleeve over her tiny clit, and she finally understood she didn’t have a penis. After her ego was broken, the feminine poured out, breaking like a tidal wave over both of them. Turning her into a woman was fun. But turning her back into a boi would be even more fun
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ashtonboi99 · 3 years
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Part 3
“Poor little thing,” said Adrian, “let me show you.” He bent down and took the boy’s tiny hand and placed it on the wet mess in the boy’s crotch. “With your size, you want to rub it, try between your thumb and knuckle.... good boy.” As Ashton started pleasuring himself for the first time, Adrian unzipped and his giant, 9” dick flopped out. Ashton’s eyes were closed, so Adrian slapped the little faggy face with his dick.
Ashton gasped, and then his eyes grew in shock at the size of Adrian’s massive dick. “Stroke it,” Adrian quietly ordered, one hand rubbing Ashton’s hair. With his left hand on his own tiny situation, Ashton help his stepdad’s giant cock in his right hand and inexpertly began to jerk it.
Adrian loved the feel of Ashton’s soft, tiny hand on his giant cock. The petite boy could barely get his hand around his stepdad’s girth, which was larger than Ashton’s own dainty wrists. Ashton looked up at his Daddy, his eyes and mouth open wide in lust, shame, and surprise. Adrian brushed the boy’s tiny hand away and guided his giant member towards the boy’s inviting lips.
Adrian slowly inserted the head of his giant cock into Ashton’s mouth. The boy stopped playing with himself so he could place both hands on Daddy’s dick. Adrian tried to be patient, but he was so truned on by this little faggot that he couldn’t hold back. He grabbed Ashton’s long, flowing hair and started face fucking the boy. Ashton gagged and his eyes watered as he struggled to take a dick is his cocksucker lips for the first time. Such a massive dick made it even harder. Try as he might, he just couldn’t handle it.
Adrian pulled out, leaving Ashton gagging and chocking. “Daddy.... please ..... stop...” the boy whimpered, his tiny body physically overwhelmed, and his submissive nature equally overwhelmed. He began to crawl away.
“Guess we’ll just try a different way.” Adrian grabbed the boy by the hips from behind and easily picked him up and threw him on the bed. Ashton couldn’t have weighed more than 90 pounds. “A little faggot girl like you needs to learn to finish what they started.” Adrian peeled then cum stained leggings all the way down, revealing Ashton’s lower body. His slender legs were completely hairless and quite pale. That lingering baby fat made his silky smooth, alabaster legs incredibly feminine and gorgeous. His thighs were creamy and inviting, and his butt was a perfect bubble. Contrary to the sad little nothingness in front, from behind Ashton was.... a goddess.
“What are you doing, Daddy?” Ashton whined.
Adrian grabbed the boy’s cast off underwear, soaked with precum. He wadded it up and gently placed it between the boy’s lips. The docile bottom accepted this new humiliation without the slightest resistance. “Shhh, baby, it’s okay.” Adrian then got a lacy bra out of his fiancée’s dresser and slipped it on the boy. “Oh that’s perfect.”
Adrian moved the boy with ease, placing him on all fours on the bed. The boy offered no resistance. He was a plaything, Daddy’s toy boy.
Adrian put a little lube on his finger and slipped it into Ashton’s hole. The hole was tighter than Adrian could ever have imagined, and Ashton moaned and whimpered, biting down on his wet gag. “Oh this is going to be good! Well, good for me.... it light hurt... a little.”
Adrian rubbed the head of his massive cock around and against the opening of Ashton’s hole. The sensation was enough to almost make the boy cum, and his little precum faucet continued to ooze. But the hardness of Adrian’s cock against hole seemed to make Ashton less stiff. Knowing it would be penetrated, his body was retreating into fully feminine submissiveness.
Adrian pressed the head in and Ashton screamed into his gag. “Relax, Tiny. Don’t forget to breathe.” Ashton did as he was told and Adrian went slowly and was gentle, breaking in the boy.
Finally Adrian could not hold back, and he gripped the boy’s hips and started pounding him. Ashton screamed, moaned, gasped, and whimpered, his tiny body shuddering with every move of the huge cock. Adrian slammed against the tiny boy, forcing every inch of his huge member in, pulling it almost entirely out, and them plunging back in. Every molecule in Ashton’s body felt penetrated. It is possible that no one has ever been as thoroughly and completely fucked as that teen sissy boy was by his sexy step dad.
Ashton’s eyes rolled up, and he spit out the gag for air, and his ego disappeared as his entire body became a sex toy for his new Daddy. He couldn’t think, he couldn’t even feel, he just took his pounding and moaned like a whore. Every second he wanted to ask Daddy to stop, but he didn’t... he wanted Daddy to keep going.
Adrian’s fingers dug into the boys delicate hips, and he balls tightened and he fucked the little faggot. Ashton was tighter and sexier than his mom, and every bit as feminine. Adrian reached around to the boy’s front to pleasure his son, but really just couldn’t find anything to get hold off. He sort of fingered the area for a bit and then gave up, focusing on his own pleasure. His veiny nine inch cock hadn’t had this much pleasure in years. Ashton’s hole was truly amazing.
Finally, Adrian felt that familiar surge, and without any warning to Ashton, he started cumming. He shot load after load into the boy, ropes of white, sticky cum breeding the little faggot, filling his virgin hole. When Adrian finally pulled out, cum was overflowing and gushing out of Ashton’s hole. Ashton collapsed on the bed, completely annihilated, and Adrian scooped up the streams of cum. He smeared it on Ashton’s face and fed it into his mouth. He rubbed his hands on the tiny body, it was as if every inch of this little boy was covered in Adrian’s cum.
Adrian flipped the boy over on his back. Adrian’s cock had softened to a semi-erect state and was down to a mere 7 inches. He pushed his dick against Ashton’s private parts, causing the dazed boy to whimper even more. Adrian poked against the mound with his dick and came again, another massive load of cum totally covering Ashton’s genitals. Adrian fingered the mess, just a giant puddle of cum between the bottom’s legs.
Adrian looked at the clock. It was 9:45 am. As he looked down at the pitiful sex slave he had just mare, he smirked and said “I guess I know what I’ll be doing this week.”
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ashtonboi99 · 3 years
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Part 2
“Oh... umm, yeah...” said Adrian, embarrassed for the boy.
“Will it ever grow, Daddy?” The boy was sniffling a little.
Adrian stood and gently kissed his smooth cheek and held the boy close in a tender embrace. Adrian’s growing dick was pushing against the boy’s tummy.
“Well.... there are ways to maybe get it to grow... a little... and not every guy needs to be big...” Adrian was becoming flustered and horny... he wasn’t gay, but he wanted this boy!”
“What kind of ways?”
Adrian reached down and tenderly held the boy’s genitals. He tugged, rubbed, rotated with the most gentle pressure. “Little exercises like this, honey.” The boy moaned at the gentle touch, clearly he was a total virgin. His moans were feminine, he sounded like his mom did in bed... actually, he sounded hotter, and more feminine.
As Adrian’s large hand worked Ashton’s androgynous package, Ashton became very, very wet. Adrian’s hand quickly became covered in the sticky goo. He lifted his hand and brushed it against Ashton’s pretty lips, spreading the boy’s precum around. He slipped his fingers in the boy’s mouth, one by one, and the fifteen year old instinctively closed his eyes and sucked on the large fingers as if he had never wanted anything else in his life. Even Adrian’s pinky was easily larger than Ashton’s little cum mound.
Adrian massaged the boy’s crotch with one hand while the boy sucked the fingers on the other hand.
“Mmmm, I think that being small....well, tiny.... won’t be a problem for you, honey. You’re a bottom.” Ashton smiled as he sucked the fingers. At the word “tiny,” his face twinged as if in shame, but Adrian also felt him pulse in his other hand. “Yes, tiny,” he repeated, this time squeezing the tiny member, sending a shiver of electricity from the soles of Ashton’s tiny feet to the tip of his head.
Adrian continued to alternate which hand was in the boy’s wet, warm, welcoming mouth, and which hand played with the boy’s private parts. As he moved, he rubbed and caressed the boy’s soft, tiny body, leaving gleams of precum on the boy’s smooth skin. Ashton punctuated the air with effeminate, breathy little gasps each time Adrian pulled out of his mouth.
“I think I finally know what to call you.... Tiny,” Adrian said with a smirk. Ashton opened his eyes and gave Adrian a smile... the sort of resigned smile of a submissive boy who is used to being humiliated.
Adrian pressed on the boy’s delicate shoulders, and Ashton easily slid to his knees. He was eye to eye with the massive, throbbing bulge in his stepdad’s pants. “Kiss it, Tiny,” Adrian ordered in a firm, confident voice.
Ashton began to mouth the bulge through Adrian’s pants, oblivious to anything but his growing cocklust. His own junk remained exposed, throbbing and oozing pitifully in the air.
Adrian slipped off his shoe and pressed the boy’s mound with his foot. Jesus, even My toes are bigger than him! He thought. “You can play with yourself, honey,” Adrian said.
Ashton looked up at his new mentor. “I never have... I don’t know how to...” he said, shame filling his adorable face.
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ashtonboi99 · 3 years
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Part one
Adrain looked at the clock. 8:30 am.... the minutes were going so slowly. He has an entire week alone with his new stepson-to-be. The two had nothing in common. But with his fiancé gone, there was no one to watch the boy. And since he had no friends and Adrian was between jobs, the two were going to be stuck together the entire time.
Adrian was excited about his upcoming marriage. His fiancée was everything he could hope for in a partner. Well, except for bringing along a fifteen year old son. Adrian wasn’t sure he ever wanted to be a dad, and he definitely didn’t want to be a stepdad to a teenage boy.
Of course, Ashton wasn’t much of a boy. He was 5’4” on his tiptoes, with long, soft hair that framed his feminine face. His body was petite and soft. He had a narrow waist, maybe 26” or 27” and no muscle mass at all, except for his big womanly butt. A little baby fat made his appear even more effeminate, and his voice hadn’t changed yet. He sounded like a girl on the phone, and had a beautiful soprano singing voice. People who called the house always mistook him for his mother, and you would make the same mistake if you saw him from behind. He wore skin tight skinny jeans, and sometimes even leggings. He usually wore a hoodie over them, a little oversized but at the same time almost fitted. The entire effect was that the boy looked like a stereotypical teenage girl.
Adrian was roused from his ruminations by a gently knock on the door. There she, err... “he,” was now!
“Hello?” Asked Adrian. He had e the bedroom, relaxing, and was a surprised to see Ashton.
“Umm, can I talk to you about something Mr. Adrian?” The boy was so timid his own shadow could beat him up.
“Sure, what is it.... sport?” Adrian always felt awkward making small talk with his androgynous soon to be step-child. He had tried all sorts of nicknames, and none of them seemed to fit.
“Well, it’s kind of personal, but I’ve never had a man to talk to about it...” Ashton was squirming and blushing. “I’m worried I am not growing enough.”
“Oh that’s okay!” Said Adrian, standing up from his desk and crossing to the boy. Adrian stood 6’2” and he towered over the tiny boy, who he could scoop up in one hand. “Guys come in all kinds of shapes and sizes, and I bet you will get a little taller by the time you finish school.” Adrian removed Ashton’s hoodie, leaving the boy naked from the waist up, “plus, we can bulk you up a little,” Adrian said as he playfully pinched Ashton’s bicep-less arm, which cause the boy to emit a girlish giggle. Adrian noted that the boy almost seemed to have small breasts developing.
“It’s not that,” he said, after recovering. “I know i’m short.... I’m worried about.... down there” Ashton’s timid eyes looked down, and Adrian looked at the boy’s crotch. Even in leggings, there was nothing there. Not even the slightest hint of a bulge. Adrian had never given it any thought before, but now he was shocked at how flat the boy was. His own impressive cock seemed to twitch slightly... wonder what that’s about? He asked himself.
“Oh, umm.... well everyone is different, and I think most guys are a little shy.... you probably aren’t.... that different..... son....”
“But... dad.... daddy...” the boy started softly, his pink lips trembling and his blue eyes watering... “I AM different....I don’t know how to explain it...”
Adrian was rapidly becoming horny, he HAD to see what the boy was talking about. “Well let’s take a look then.” He forcefully moved the boy to a different position. Then Adrian slipped to his knees and put his large, powerful hands on the teen’s small hips. The boy was like a delicate toy doll! Adrian tugged and rolled down Ashton’s leggings, and couldn’t believe what he saw...
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ashtonboi99 · 3 years
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ashtonboi99 · 4 years
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ashtonboi99 · 4 years
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