Bondage Princess May

For the past three years, May had the same babysitter, a bubbly teenager named Labelle. After knowing her for so long, May was very upset to see her leave for college. She didn't understand why she had to leave, that the college she lived at now was too far away to continue babysitting her.

Today was the day she'd first meet her new babysitter, Mandy, her mother, called her down at the usual time before she went to work. Downstairs in the living room, sitting on the love seat across from her mom was her new babysitter. May thought she'd also be a teenager like Labelle, but she was a bit older. Much older, maybe, than her mom, but it was hard to tell. She had a medium bob haircut that was as black as oil. She wore a black dress that sent down to her knees, with open toe heels. She gazed at May with deep blue eyes that were inviting in a strange motherly way, but not quite.

"Ooh, your daughter is much more adorable than what you described!" the woman swooned.

"May, this here is your new babysitter, Miss Bethany."

"Please, just call me Beth." the woman corrected.

"Miss Beth. I know you want Labelle back, May, but she's just not available." Mandy said. "Beth is really nice, though. Just give her a few days and I'm sure you'll grow to love her!"

"Not to worry. All kids love me." Beth said, smiling. It was a warm smile, but May felt that there was some other emotion behind it. If there was, she couldn't identify it.

"Okay, I gotta go run some errands." Mandy said. "Be a good girl, okay? Momma loves you." she came over and gave May a hug and kissed her on the forehead before heading out the front door. There was an awkward silence that filled the room after she left. May clung to the wall leading down the hallway, studying Beth intently. The older woman continued to smile at her.

"So what do you like to do?" Beth asked.

"Umm... I like to watch My Little Pony." she replied. "I also like to play with these doll playsets."

"You had me at My Little Pony. That is so adorable! I've never actually been into ponies, myself, but I've babysat a few kids who just adore them! Tell me, which one is your favorite pony?"

"Uhm, well, I kinda like Fluttershy the best." May replied. "She's so nice and she loves animals!"

The two continued to talk about ponies and similar topics until Mandy returned. The more May talked, the more open she was to this new babysitter. She wouldn't replace Labelle - nothing ever could - but she was disappointed to see her go once all was said and done.

"You have a most wonderful daughter." Beth said as Mandy paid her. "I can't wait to babysit her again."

"Oh don't worry. We'll have plenty of need for your services." she replied. Once Beth had left she turned her attention to her daughter.

"What do you think of her?" she asked.

"I really like her!" May replied. "She's really nice, and we talked a lot about My Little Pony!"

"Well that's good. I plan on hiring her full time."

May let out a squee of excitement and gave her mom a tight hug. Beth might not be able to perfectly fill the hole Labelle left, but she was a good replacement, and probably the best they were going to get.

• * *

Beth adapted quite well to their schedule. She was always interested in what May did and what she had to say, and before and after Mandy went to or returned from work, the two adults engaged in meaningful conversation. One day, Beth pushed the conversation to the subject of May's father.

"I don't mean to pry, but it's just that I've never seen any sign of any hubby around." Beth said. "Is he still around?"

"It's... an unpleasant topic to think about." Mandy said, pouring herself a glass of iced tea.

"Oh, sorry." Beth said. "You don't have to share if you don't want to."

"No, it's fine. I want to get it off my chest. Well, it was largely due to my own stupidity, I guess. I met him in college, he was studying to become an investment banker. I met him not too long after he got this offer from a stock trade company. From what he told me, it was a pretty sweet deal. He left college to pursue this job, and we continued to date. Looking back on it, I realize that he didn't see any real romance in our relationship. It was all a game to him. The fancy dinners, the gifts... it wasn't so much about the gifts as much as it was him flaunting these gifts at me. He hit it big and he was basking in it."

"That sucks." Beth solemnly replied. "So where did May come into this?"

"I was still starry-eyed by all the gifts. I wanted to marry him. I thought his reply was genuine, but in hindsight, he was so blase about it. I should have noticed it sooner. I wish I could go back in time and slap some sense into my past self. We didn't even get married when I got pregnant with May. He was long gone by the time she was born."

"You mean she's never known her father?" Mandy shook her head.

"She doesn't need to be burdened by such a thing." she replied.

"So what happened to him?"

"Some pretty serious fraud charges. He got greedy and tried to steal from the company. Turns out one of the biggest rules in his world is you don't try to bite the fish that can bite back. Now he's serving time in white collar prison."

"Ow, that's terrible." Beth replied, resting a hand on Mandy's thigh. "Have you ever tried looking for a new boyfriend since?"

"Not really, no. I've been more focused on providing a living for me and May. Besides, what guy's gonna want to date a woman with a bastard daughter?"

"Hey, that's not cool." Beth said. "Marriage is a pretty archaic and overrated concept. It isn't right to May to have that unnecessary detail about the circumstances of her birth inexorably tied to who she is."

"You're right, I'm sorry."

"So do you ever plan to tell her about her father?"

"Maybe when she's older. A seven year old girl doesn't need to be bothered with such a terrible history.

"Thank you for listening, Beth." Mandy said, wrapping an arm around the other woman. "It felt good to vent about it."

"Glad I could help."

Truth was an incredible burden to bear. For Beth, she bore the burden of many truths, most of whom she'd grown accustomed to their weight over the years, but Mandy's story was a particularly heavy one for her. It shouldn't have been; there were many sadder stories she's heard before. Maybe it was because May was affected before she was even born. Most other kids in her line of work were victims later in life; dads beating up their sons to "toughen them up", or ravaging their daughters to satisfy their lusts without actually loving them. It was enough to break your heart.

Beth returned to her quiet home. She sat down in her thinking chair, thinking everything over; all the variables, considerations and most importantly, who she would affect with her actions. What was most important over all else was May's happiness. As she had done many times before, Beth would see how May would respond to her "love". If she accepted it, great, if not, it was an easy fix, and May could return to her life untraumatized and unaffected by her encounter.

• * *

Beth continued to babysit May for several more weeks. Over time, she opened up more to the small girl, sitting with her while they watched TV, helped her with her homework, and even cooking dinner on nights that Mandy had to work or run errands.

May quickly warmed up to the older woman as well. While she continued to miss Labelle, Beth was a great replacement. She was strict and kept to a schedule like a machine, but sincere when it came to listening to her about her day, what she liked to do, and her problems with homework. She mentioned her new great babysitter to her friends at school, and discovered that she was quite the rarity, as was Labelle.

After school was let out that day, May returned home as she usually did. When she knocked on the front door, however, the person to answer ws Beth and not her mom like she expected.

"Hey there, little one, Beth greeted, kneeling down to give May a friendly hug." How was your day?"

"It was fine. Got an A+ on my math test!"

"Oh really? That's excellent! Your mom will be so happy to hear that!"

"Speaking of which, where is she?"

"She got called to work. She said she'd return by dinner time."

"Okay!"

"so I get the rare responsibility of making dinner for both you and your mom!"

May smiled and gave Beth another hug.

"I'm gonna go do my homework now!" she said.

"Okay, then. I'll bring you a refreshment in a moment." Beth said. May scurried upstairs to her room, and Beth went to the kitchen. She pulled out a glass and poured some ice and lemonade into it. Next, Beth pulled out a small jar from her purse containing powdered lemon balm. She scooped a small teaspoon of the mint and mixed it in with the lemonade.

Beth nonchalantly brought the finished drink upstairs and placed it on a coaster on May's desk, where she was working feverishly on her homework.

"Thank you!" she said gratefully, though she didn't touch the drink until a few minutes later.

"So it begins." Beth thought to herself. She sat down on the bed and watched May as she continued working on her homework. The lemon balm Beth added into the lemonade was a natural sedative and useful for problems with anxiety or sleeping. As the minutes passed, the balm began to take effect. May's head was drooping and she repeatedly shook her head, trying to stave off "exhaustion".

"I'm feelin' kinda tired." she said, yawning.

"You must be exhausted from school." Beth said. "Why don't you take a nap?"

"O...okay." she said, yawning again. May slid off her chair and came over to the bed and plopped down over the covers. Beth stood up and stroked May's head.

"Rest well, little one." she cooed.

• * *

May didn't know for how long she slept, but she still felt a little drowsy and groggy when she woke up. The blinds were drawn shut, and it was still daytime outside based on the light that still crept through the cracks.

"Did you have a good nap, little one?" Beth asked. Her shadowy form stood at the doorway. The room seemed darker than it should have been. May couldn't make out any of her features.

"A little. I need to finish my homework, though." May replied.

"Now hold on a minute. You should take a moment to recuperate."

"Okay..." May said. Beth walked over and sat down on the bed next to her. She wrapped her arm around her and pulled her close.

"Come sit on my lap." she said gently. May complied, and she crawled up onto Beth's lap so she was seated on one thigh. The babysitter felt strangely warm, and her clothes were a little too smooth and not at all like they felt earlier. One of Beth's hands coiled under May's butt, which felt oddly sensitive and ticklish, causing her to yelp and jump slightly.

"Hnnh, that tickles!" She giggled. The shock was enough to jolt her out of her spell and made her more aware of her surroundings. The first thing she noticed was that both of them were completely naked. Maybe it was because she just woke up, but she wasn't as shocked or surprised as she may have been otherwise.

"Why are we naked?" she asked.

"It's more relaxing this way." Beth replied. "It's important to remember what it's like to be naked. This is the way nature intended."

Beth situated May so her legs were straddling the older woman's hips. Her rather large breasts were right in May's face. She tried to ignore them, but Beth seemed to only bring more attention to them, the way she held May's head close to them. She knew it was impolite to stare, but this close to her bosom, it was all she could look at!

"What do you think?" Beth asked.

"Huh?"

"Do you like being naked?"

"A little, I guess. It is a little exciting."

"I bet your mom doesn't allow you to be naked, does she?"

"No, she doesn't. She says a proper lady keeps her clothes on."

"Well, it is important to maintain your modesty while in public. But, while we're alone together like this, there's no harm in stripping down naked."

Beth scooted further back onto the bed and laid down with May so she was on top of her babysitter. Beth's hands stroked May's back like she was a cat. The little girl's head rested on Beth's incredible chest. The were remarkably soft and warm, and they warped under her weight. Given their current situation, May wondered if it would hurt to feel them.

Beth said nothing as she sat up on her chest. She planted her legs on other side of Beth, careful to not place too much of her weight on the woman.

"These are really big." May commented. "Bigger than my mom's."

"Every girl has different size breasts. Once you turn around twelve or thirteen, you'll develop a pair of your own, too."

"Can... can I touch them?"

"Go on ahead. It feels really good if you touch them right."

May reached out and grasped one soft orb in each hand. Amazingly, they were even softer against her fingers. Her thumbs prodded the nipples, which erected quickly under her touch.

"It's rather of polite to you to ask for permission before touching." Beth said. "It's rude to touch without permission."

"I'm a good girl." May said, continuing to gently squeeze her boobs.

"Yes you are, May. You're also making me feel really good." Beth's face was flushed a light pink, and her breathing was starting to get heavy. "Do you want to feel good, too?"

"Yeah! But... I don't have boobs like you." May said disappointingly.

"That's no problem at all. There are plenty of ways to make a girl feel good."

"I wanna feel good!" May exclaimed.

"Then lay back on the bed and I'll make you feel better than you've ever felt before."

May climbed off of Beth and crowded to the head of the bed. She laid down, resting her head on the pillow. Beth crawled up to her so her head hovered just above May's stomach. Gently, she grasped her upper thighs and spread them apart. She gazed at May's plump virgin labia.

May instinctively covered her crotch with both hands. She watched Beth intently with a look that conveyed both curiosity and a little bit of fear.

"Kindly move your hands, honey." Beth said. "Otherwise I can't make you feel good.

"Mom says this is my private place." May said. "She said I'm not supposed to show it to people."

"Then this will be our little secret, okay?"

"O-okay." May slowly removed her hands, granting Beth full access to her pussy. She lowered her head further down until her lips were mere centimeters from her young peach. May could feel Beth's breath on her cooch, and she squirmed around, giggling from the ticklish sensation.

"Here we go, May." Beth said right before she stuck her tongue out and dragged it up the young girl's slit. May let out a high-pitched cry of shock that very quickly turned to one of joy.

"HMN! That feels so weird!" May exclaimed. Beth lashed at her pussy repeatedly with her tongue, prodding and teasing her sensitive slit. May's legs trembled under Beth's grip. This sensation was unlike anything she ever experienced. She could feel the blood rushing to her face, and a powerful ticklish sensation between her legs was rapidly building up.

"Whablbl-ngh!" May tried to say something, but the only thing that came out was a string of gibberish. Beth hummed with approval and continued her treatment. She used her thumbs to spread May's labia apart, and she jammed her tongue inside and rolled it around. May pounded the bed with her tiny fists, but there was no strength behind it. It was more of an involuntary reflex from the pleasure.

May's flavor was a light lemony taste. Beth was amazed at just how much girl juices she was leaking out. She was quite the natural at this, ore than any kid Beth discovered in a very long time. Trained properly, she would become the perfect little nymph, same as how Beth started out.

May's eyes rolled in the back of her head and her limbs twitched violently as she had her first orgasm. Her vaginal muscles contracted around Beth's tongue, and she squirted her sweet love juices into the woman's eager mouth. May had such an intoxicating flavor, Beth was nearly getting drunk off of it! She was most definitely a keeper; she was very open to the idea of sex, and she didn't protest even once.

"Uah... hah..." May panted heavily as she came down from her high. Beth looked up at her. May's hair was slightly dishevelled and her eyes glazed over. She wore a stupefied expression on her face, one of a freshly fucked virgin. On the face of a little girl, it was a sight that rivaled any work of art, even if it was more taboo than the Forbidden Fruit.

"Did you enjoy that, May?" Beth asked, moving to a seated position.

"That felt really good!" she exclaimed. "I've never done this sort of thing before!"

"This is called sex, when you touch yourself down there to feel good, but that's just one way of doing it."

"There are other ways?" May asked, her eyes wide and gleaming.

"Certainly! If you want, I can show you more ways to have sex."

"Yeah! Yeah! I want to have sex!" May said cheerfully, bouncing around on the bed.

"Okay, then. First, lemme show you something." Beth spread her legs apart to reveal her crotch. However, instead of a vagina, she was sporting a thick cock. May's eyes widened though it was more out of curiosity than fear.

"Woah! I didn't know you were a boy!"

"I'm not, but then I'm not a girl, either." Beth explained. "I'm somewhere in between. We're called hermaphrodites, but I prefer futanari, or futa for short. Basically it means I have everything both genders have."

Beth laid back and spread her legs apart. Along with her penis, she had a marvelous set of balls with skin as smooth as silk and tight as a drum. With one hand, cupped them and pulled them up. Underneath was her pussy, defined by equally smooth, plump lips.

"Wow, that's really cool!" May said, leaning in to get a better look. "If you had kids, would you be a mommy or a daddy?"

"That depends on if I'm the one gets pregnant or gets someone else pregnant.”

"What do you mean?" May asked.

"Where do you think this goes?" Beth asked, gesturing to her cock.

"I don't know."

"It's meant to go in here." Beth patted May between her legs, and to drive her point home, she dipped a couple of fingers into her cooch. May gasped and clenched her muscles together involuntarily.

"Haaah!" she shivered. "That feels so weird and... so good!"

"Do you want to have sex for real?"

"Yeah!"

Her enthusiasm was admirable. Beth laid May back on the bed and knelt down over her, the woman's cock resting on the child's stomach.

"Okay, then. First thing before we begin, you have to get me ready. Grab my dick like this and move your hand up and down it, like so." Beth demonstrated by jerking herself off for a few seconds, careful to stop before she got an erection. May had to discover that under her own power.

"Okay!" May grasped the cock in her hand and stroked it as Beth instructed her. It was quite warm, she noticed; warmer than Beth's fingers or legs. As she massaged and jerked it, as if it were some type of alien life form, swelling up and straightening out in defiance of gravity. In this new form, it looked like a completely different entity. The foreskin didn't entirely cover the head, and underneath, May could see the bare head, almost glowing hot pink.

"Why did it get big like this?" May asked.

"When it does this, that's called an erection. That means it's ready to go inside you."

"Is... it all really gonna go in?" May asked. "It's rather big..."

"It'll fit, don't worry." Beth assured her. "Now just relax."

May relaxed her muscles as best she could and watched as Beth spread her legs apart. She rubbed her cock against her entrance, which caused her to twitch violently as it rubbed against the sensitive pink button just above her entrance. How has she gone this long without knowing the special ticklish area down there?

Beth probed May's pussy lips with her fingers again to get her all nice and lubed up for the plunge. She was leaking her sweet juices everywhere, creating a large growing damp spot on the sheets just underneath her ass. Most definitely, once they were done here, the bedsheets would need to be washed.

Once May's young pussy was nice and swollen from the arousal. Beth guided her cock to the girl's entrance. The lips parted easily under pressure, and the head popped inside. May grunted as she felt a new and truly unique sensation in the core of her body. She could feel a mild buzz from the shaft rubbing against the sensitive nerves both in and outside of her body. At the same time, there was also a slightly discomforting, but oddly fulfilling feeling in the pit of her stomach. It was not unlike the feeling one would have after a full hearty meal, but at the same time it was worlds different.

"How are you doing?" Beth asked coolly.

"It feels really weird, but good." May replied.

"I'm going to push it in even deeper now." Beth pushed forward with her hips, inching her dick ever so slowly, deeper into May's love canal. She could feel the head pushing in the thin membrane that was her hymen. Beth had been through this stage more times than she could remember. All the girls reacted pretty much the same, and unfortunately there wasn't anything she could do to help May prepare for the pain of getting her cherry popped. she had a code to live by, and Painkillers would violate that code.

There was a sudden twinge of movement on Beth's part as she fragile membrane was torn apart. She sunk several inches in further, stopping when she struck against May's cervix. The little girl let out a high-pitched cry and her body locked up with pain. Her vaginal muscles were tightening around Beth.

"U-u-uhh!" she whined, her voice trembling. "That hurt!"

"Give it a moment. The pain will subside quickly." Beth assured her. To help drown out the pain, she gently and lightly massaged May's clit with her thumb. Her sharp breathing quickly subsided as the pain faded away.

"Sorry about that." Beth said. "Nature has a terrible sense of humor, and our first time ever doing this is a painful introduction."

"Is it always painful?" May asked, still recoiling from the sting. It was a sharp and precise pain, like a needle injection, and like a flu shot, it was over before she knew it.

"Feeling better now?" Beth asked.

"Yeah... my mound still feels a little sore, though."

"Then let me help you with that." Beth moved her hips back and forth very slowly as she continued to prod and massage May's clit. The little girl's expression soured at first as she felt the sting return briefly, but it quickly went away to be replaced by the same kind of intense feeling that engulfed her body when Beth ate her out. It built up, same as it did before, but for some reason, this time the sensation was so much more intense. It might have been because Beth put her boy thing inside her, but she didn't really know since she never did this sort of thing before.

Beth pulled May up onto her lap. Her hands rested on the girl's ass as she bounced her up and down on her dick. May's muscles constricted around her, making their thrusting motions a bit more difficult. She rested her head against Beth's large rack and hugged her tightly.

"It feels... really nice." she sighed contently. "I feel so full and warm."

"It gets better." Beth assured her. Her fingers dug into May's ass, which made her squeak from the ticklish feeling. Her fingers inched slowly inwards towards her asshole. May was so focused on the glowing ball of pleasure in her pussy that she didn't realize what Beth was doing until her fingers probed her tight pucker.

"AH!" May gasped. "B-beth! That's a dirty place!"

"Maybe, but it's also a very sensitive spot."

Beth's index and middle fingers dug into her asshole, trying to claw their way past the sphincter muscle. Getting her asshole spread open outside of her body's natural functions was an incredibly alien experience for May. she could feel the digits inching in all the way up to the knuckles. It wasn't painful, but she could definitely feel her muscle being spread apart.

As she squirmed about on both her fingers and her dick, May felt something else entirely new. Something about getting her ass plugged up an intruder made the feeling in her pussy even more powerful. At the same time, having her love canal filled up also made her asshole feel even better. It was almost paradoxical how they amplified the already overwhelming tickle feeling May felt in the core of her body. Even if it was dirty, getting her ass plugged up along with her girl hole was the most wonderful thing she ever experienced.

May's grip tightened around Beth, counting for arms and vaginal and anal muscles, as she hit her second orgasm. This one, however, was so much more intense than the previous one. So intense, in fact, that May couldn't even think about how intense it was. Her first double orgasm numbed her mind and reduced her to a whimpering, vibrating marionette on Beth's lap. What limited capacity her consciousness currently operated at knew it was the most blissful and amazing thing she ever experienced in her short life.

May's vaginal muscles felt heavenly to Beth as they tugged at her in all the right ways. She held May close and let out a long contented sigh as she shot thick ropes of her sperm into her pussy. The way May's muscles contracted around her the whole time in a milking motion, it was almost like her pussy was eager to drink up every last drop of Beth's baby batter!

As she came down from her high, Beth rolled over and laid down with with May resting on top of her. Beth could feel her heartbeat reverberating between them. May's quickened breathing was slowly simmering down. A few minutes later, she stirred back to consciousness and pushed against Beth's grasp to sit up.

"Mnnh... what was that?" she moaned, stretching her arms and arching her back. "That felt so good!"

"That feeling is called an orgasm." Beth explained to her. "That's what happens at the end of sex if you do it right."

"I feel... a little warm and tingly in my tummy."

"That's because I had an orgasm, too. I put my love inside of you."

"Hee hee hee, that rhymes!" May giggled. "What do you mean by your love?"

"It's... hard to explain, but I filled up this special room inside your girl part with a thick warm white goo. It's what boys make when they orgasm."

"Ohh... is it dirty?" May asked.

"Not at all. It's a lot of things, but dirty is not one of them."

"Can you fill me up with your love again? I really liked it!"

"Later, honey. My boy part needs to rest for a bit, plus I still have to make dinner."

"Okay. I'm kinda feeling a little tired, anyways."

"Sex does take a lot out of you. Go ahead and rest, honey."

Beth removed her fingers from May's ass and gently extracted her cock from her fox hole. Her labia was spread far apart and the hot pink hole oozed Beth's sperm, thick as maple syrup.

"By the way, May, remember that this is a secret thing between us." Beth said coolly. "Don't tell anyone about it, not even your mom."

"Okay." May said, curling up into a ball, still naked, before drifting off to sleep. Beth left her in that state and dressed herself back up before returning to the kitchen. Mandy still had another two hours at the office before she returned home, and Beth would have all trace of their activities cleared away by then. She had many more plans in store for May. Today she merely introduced her to a larger world.