Disclaimer! None of this is real, and for the love of Atheism, please don’t try to replicate any part of this. It’s purely fiction, and I don’t want to be held responsible for the actions of some idiot asshole.

            This is Chapter 2 of Bondage Princess May. Special thanks to Ikataii for her characterization of Mistress Beth.

Bondage Princess May

            Chapter 2: From Max to May

“Now, you’ve been such a messy, bad boy.” Beth scolded. “Wouldn’t you rather be a girl forever? I’d still have to spank you if you were bad, though.”

            “Y-yes…” Max answered truthfully, feeling her cock rub against his asshole. “But I can’t… it’s wrong to act like a girl.” He rested up against her, trying to keep the cock from going in his ass.

            Beth lay him down across her lap and bent down to kiss at his lips. “I can make you a real girl, if you want, but you’ll have to promise you’ll be good and do what I want you to. I’ll also be able to fuck you in places other than your poor ass.”

            Max thought about it for a while. What would his mom say about him being a girl? What would his girl name be? Would he like being a girl? If he didn’t, would it be reversible? “I… I don’t know.” He said. “I mean… I want to… but…”

            Beth kissed him again and smiled. “If you don’t like it, I could change you back, but you’d still have to do what I say. If you want to be a girl, this is your chance, alright? Otherwise, you’ll just be a boy wearing a dress.”

            “Then yes.” He said, responding to that last part. “I want to be a girl.”

            Beth sat him down so that her breasts were pressing against his back. She hugged him tightly and slid her hands up over his chest. It softened and budded slowly under her fingertips, turning into young breasts. Max gasped and felt his chest slowly expand as if he was being inflated. Soon a nice pair of tiny breasts appeared on him, which was about an inch bigger than they used to be. Beth smiled and slid her fingers over one nipple, then reached down and pressed at the tip of his shaft. It slid back into the boy’s body and formed a tight, virgin slit.

            It was at this point that Max actually showed any pain. He cried out and convulsed in her grip, feeling his cock disappear, followed by a peculiar emptiness grow inside of him, below his stomach. Finally, Beth turned him around and kissed him on the lips, her hands slowly running from his face down his body and finally his legs. Max kept kissing Beth, feeling his body change underneath her hands. She finally broke away from the newly formed girl’s lips and smiled. “There we go. Now you’re a pretty, real girl. How does it feel, pet? Do you have a name you’d like to use?”

            He, or rather, she, didn’t know what to say. “I… I don’t know.” She answered, her voice higher pitched. “Can… you please name me… Mistress?”

            Beth smiled and pulled her close, then kissed at her forehead. “How about Jill?” She suggested, stroking the girl’s back. “You look like a nice, cute little Jill to me.”

            “Umm… how about… May?” she asked, cooing from her Mistress’s touch. For some reason, she felt a lot more sensitive now.

            “May? So close to your old name? Hmm… that actually sounds good! That’s just one latter change for your mom to get used to. Oh, how could I forget?” Her fingers ran through May’s hair and drew it gently out until it grazed her shoulders. May inclined her head as her hair was extended to properly match her new body, which was a bit slimmer than when she was Max, and while feeling no penis between her legs was odd, it felt very right.

            “Th-thank you Mistress!” she exclaimed. “it feels… perfect!”

            Beth laughed softly and pulled the girl close to her body, petting at her softer hair and kissing her forehead. “I’m glad you like it, pet. I’m very, very glad you like it. Now, do you want to be a good girl for Mistress and give her your side of the deal?”

            May looked up at her Mistress. “S-sure… what is your side of the deal again?” May ended up forgetting in the commotion of having a girl’s body.

            “You agreed to be a good girl and let me use you like one.” She said, grinning darkly and bending down to kiss at her pet’s lips. “Lay back down on the bed. I’ll make you a nice proper woman.”

            May leaned into the kiss briefly before breaking away and lying down on the bed. She instinctively spread her legs apart, and covered her miniature breasts with her hands. “Like this?” she asked.

            “Yeah, just like that.” Beth climbed above the girl and began stroking at her shaft, bringing it to full hardness before May. “Now, I need you to relax.” She told May. The head of her member began pressing tightly at the girl’s entrance, wedging its way into her. May tried to relax, but suddenly tensed up as her cunt was penetrated by the woman’s cock. She moaned as it spread apart her virgin lips and rubbed up against some kind of resistance within her. “OH! Mistress!” she cried out.

            “Mmmnn… good girl, May.” Beth moaned, placing her hands on either side of May’s body. “This next part is going to hurt a bit, but it’ll pass. You trust Mistress, right?” she kissed her on the forehead and paused for a moment as if waiting for an answer, but before May could, she thrust forward quickly, piercing through the girl’s hymen. The little girl cried out in pain as she felt like she got stabbed in the crotch. Her limbs thrashed underneath Beth. “OWWWWW!!!!” She screamed. “MISTRESS!!! IT HURTS!!!”

            The stronger woman grabbed May by her shoulders and pinned her against the bed. “Relax, May. You have to relax. It’ll pass shortly, I promise.” May nodded her head, slowly relaxing her body as the pain subsided. Beth breathed hard over the girl and moaned with each little movement she made. “You’re so tight. It feels wonderful.”

            “Is… is tight good?” May asked. “I hope I’m a good girl, Mistress…”

            “Tight is very good. You’re squeezing Mistress’s cock nicely, pet.” She ran her fingers gently through her plaything’s hair and kissed her on the cheek. “You’re a very good girl.”

            May smiled as she was complimented by her Mistress. She leaned up as best she could and kissed Beth on the lips, turned on more now that she was a girl. “Please… make me a wonderful woman, Mistress…” she whispered.

            “I will, pet. I’ll make you my perfect little plaything.” Beth said before slowly pushing deep into the girl. She kissed May deeply on the lips, tasting her deeply and held her tight.

            “Th-thank you, Mis-ah! AH! AH!” May moaned each time she was pumped into. Beth’s huge cock bulged out her stomach with each thrust, and the feeling of her pussy walls gripping the shaft inside her only accomplished in arousing her even more. “It feels so good!”

            “I’m glad you like it- ahhhnnnn… May.” Beth began thrusting harder and harder into the girl, her breathing quickening. May couldn’t do much but try to hold Beth as close to her body as possible. Her hips rocked back and forth with each thrust, and her clitoris stuck out, erect.

            Beth clutched May and rolled them both around so that now the Mistress was on the bottom and May was sitting on her lap. She continued to thrust upwards into her tight pussy, her own breasts swaying back and forth.

            In this new position, May tried to thrust down in attempt to drive the cock deeper into her. A strong feeling fell over her, and her pussy lips grew slick with her own cum. She let out a loud cry of pleasure as she had her first orgasm as a female. Unlike her male orgasm, this one seemed to shake her very core.

            Beth leaned up and kissed May on the lips as she game down from her feminine climax. “Nice, isn’t it, coming in waves like that?” she panted. “You’re a very good girl. I’ll help you come again.” She slowed down her thrusts into the girl. Suddenly, her hips bucked up hard into May, ramming against the back of her womb, and she moaned out loud with her own pleasure.

            May’s eyes opened wide as she felt something warm fill up the cavity in her body. “O-oooooohhh! This warm feeling!” she exclaimed. “It’s soo… Mmmm! MMMNNNN!!! IT’S SO GOOOOOOOOOOOD!!!” The feeling of being filled up with sperm caused her to have another orgasm. Beth held her close, continuing to pump hot sperm into her pet’s young cunt. She gently pet May on the head, who fell up against her Mistress’s chest after her orgasm ended.

            “I’m so happy you like it, pet.” Beth cooed. “I’ll be doing it to you a lot in the future. Well, then, what should I do with you next…”

            May looked up into her Mistress’s eyes. “I love this feeling… it’s so… right…” she nuzzled against Beth’s chest, her head resting on her large breasts. “Can you please teach me how to act properly like a girl?” she asked.

            Beth thought about it for a few seconds. “Hmm… I’d just have to decide where to start…” she tapped lightly at her chin and pondered about what to do with the girl.

            May slowly pulled off the shaft, feeling a weird emptiness in her. “How about… you dress me up like a girl?” she asked. “And then show me how a girl is supposed to act?”

            “Well, your dress should still be fine. Why don’t you put that on with these?” Beth reached over and picked out a pair of white panties, then handed them to May. “I’d say a bra too, but you haven’t quite the breasts for one.”

            May took the panties and slowly put them on. It felt rather unique having the fabric rub against her pussy lips. She then grabbed the dress and put it on as well, surprised at how well it fit now. “How do I look?” she asked her Mistress, spinning around for her.

            “You look very pretty, pet.” Beth slid up from the bed and bent down to kiss her gently on the lips. “Let me get dressed and we’ll go out shopping.” She quickly pulled on the black lace panties and bra, followed by the simple black dress that she had been wearing before.

            “When can we go back to mom?” she asked.

            “After we go out and you practice being a good girl, I’ll take you home.” Beth answered.

            “And what about shoes?”

            “Hmm…” the woman stepped into her closet and dug about, tossing pairs of children’s shoes aside. “Aha! Here’s a good pair. Nice simple flats that go well with your dress.” The shoes were pink shoes that had one strap with a golden buckle; a very nice match with the dress. May put on the shoes and tried walking around.

            “I can move pretty well in these.” She said. “Are we ready to go now?” Beth nodded and slipped on a pair of low heels, then held her hand out to May. “Let’s go out. Anywhere you want to go?”

            “You said we were going shopping.” She replied. “What are we going shopping for? Clothes?”

            “Yep. We should get you some more outfits, if you going to be a girl now. Most of your boy clothes won’t work anymore.” She answered, leading her out to the car.

            “Y-yeah…” May walked out with her, feeling a bit weird with a draft blowing between her legs. “Why are you doing all this for me, though?”

            Beth helped her into the passenger seat, watching May’s movements and making notes. “Well, I’ve always wanted to have kids of my own, but I don’t really have the time.” She responded. “I figure I’ll be kind of like that nice aunt that spoils you instead.”

            “O-ok… but I wonder what mom would say?” she said, buckling her seatbelt. “What If she doesn’t let you near me again?” Because the door was already closed, May had to repeat this when Beth came around to the driver’s seat.

            “I’ll explain things to her.” Beth answered. “We’ll have to keep some of the things we do a secret, though, okay? I don’t think she’d understand.”

            “S-some things? Like what?” she asked.

            “Like you can’t let her know that we have sex, understand? She won’t want you to see me anymore, and then we can’t have our fun, pet.” She reached over and ruffled May’s hair, then put the car into gear and pulled out of the driveway.

* * *

The drive was only about 10 minutes before they pulled up in a parking lot outside of a department store. As they were climbing out of the car, May suddenly had a thought.

            “Oh, Mistress, what should I call you out in public?”

            “Just call me Aunt Beth.” She said as she led the girl inside. They silently walked to the girl’s section, where Beth smiled at the rows of lovely clothes spread out before them. “See anything you like, May?”

            May looked about the shelves, checking out some of the clothes. Among the ones she chose were swimsuits, dresses, skirts, shirts, and of course, underwear. Beth helped her with picking out some of the outfits. Some she even threw in without even consulting May.

            Once she was carrying a healthy amount of clothes, Beth led the girl off to the dressing rooms in a back corner of the store and stepped into the large stall in the back. “Here we go. Why don’t you try these on and make sure they fit?”

            “Ok.” May took off the dress and her shoes and began to try out each one of the clothes. She tried different combinations of everything to see how she and Beth liked them. “How does this look, Aunt Beth?” she asked, currently wearing a one-piece swimsuit.

            “It looks nice, May. Here, let me get a better look.” She said, pulling the girl onto her lap as she sat on the bench. Her fingers traced along the edge of the swimsuit, checking its fit, and feeling tenderly at the girl’s skin.

            May looked back at her Mistress. “What are you doing, Beth?” she asked, feeling her hands adventure across her body.

            “Just making sure it fits alright.” She said aloud, and then whispered, “and getting another good feel of you, pet. I couldn’t resist anymore with you looking so adorable.”

            May shivered in pleasure, feeling her sex drive burning up again. “Mistress… are you really gonna…?” she asked.

            Beth chuckled and rubbed her petite breasts. “Don’t worry, I’ll just rub at you a bit, pet. This is something you should get used to as such a lovely little girl. Boys will want to do this all the time.” Her fingers dipped down and pressed softly at May’s slit, coaxing a gasp out of her mouth. Slowly, May grinded her hips against Beth’s hand.

            “Mmmnn… it feels… good…” she whispered, resting up against her Mistress. Beth licked at May’s neck and held her tight. “You know, they sometimes have cameras hidden in the fitting rooms. Someone might be watching us right now.”

            May suddenly panicked and tried to pull away from Beth. “Mistress… we can’t… someone will find us, and we could get in trouble!”

            She held her pet tight and chuckled. “Come now, if you got to watch this, would you want to interrupt it?” she pressed her fingers tighter at May’s entrance and licked her lips. “Besides, isn’t it exciting thinking that we could get caught?”

            May continued to struggle, but she suddenly had this hot feeling building up in her. It was as if she was actually getting turned on from the idea of being seen through the camera. “Please… make me cum…” she whispered, spreading her legs open.

            “That’s a good girl. You should always fight it at first. It makes Mistress happy when she sees you give up.” She whispered. She pulled the bottom of the plain one-piece swimsuit aside and slid a finger smoothly up into the girl’s entrance.

            “AH! Haaaahhhh…” May shivered violently as the finger poked into her pussy. “I’m glad I could make Mistress happy…”

            “You make me very happy, May; very, very happy. You’re my favorite pet.” She said, nipping lightly at her neck as she pumped faster in and out of her.

            “Mmmmmm…. MMMNNNN!!!” May’s pussy squeezed Beth’s fingers as she came, wetting them with her juices. “Mistress… I feel good again…”

            Beth pulled out a couple of wet wipes from her purse and pressed them at May’s slit to prevent her from leaking on the clothes, then licked her own fingers clean. After all, she didn’t want the girl to make a mess of her new swimsuit.

            May looked up at her Mistress, panting lightly. “Mistress… do you like these clothes?” she asked, kissing her on the lips.

            Beth laughed softly and petted her on the head. “I do, pet, I do, but it seems like we’re forgetting something… ah, I know. Pack up your things and we’ll go pay for them. I know another shop to go to.”

            May nodded and took the swimsuit off and got into her normal dress. She picked up the clothes and carried them out of the dressing room back to their shopping cart. Beth breezed them through the checkout and back into the car in several bags.

            “Well then, let’s get going.” She climbed into the driver’s seat, and May sat down in the passenger seat. “Where are we going now?” May asked.

            “A special sort of store. I have an agreement with the owner. He makes custom clothes, though his fittings are a little… unconventional. You’ll be a good girl for him, right?” she smiled warmly at the girl and pet her on the head again.

            “Ok!” she answered, smiling. As they drove down the street, May looked around for any signs or places that might look familiar to her. Nope… she has never been here.

            Beth pulled into an alley and parked outside of an unmarked door. “Sam’s in here. Come on, little pet. We’ll get you something nice.”

            May hopped out of the car and walked inside, keeping close to her Mistress, uncertain about what lay on the other side. The shop was dimly lit by bare bulbs hanging over harnesses and leather slips adorned with cuffs and collars. “Sam, I’ve got a new pet to be fitted!”

            “Fitted?” May asked. “Is this another clothes shop?”

            Sam came out from the back of the store, a large solid man wearing a leather vest and pants, and nothing else. “It is, little lady. Got a design in mind, Beth?”

            “Oh, I don’t know. Something pretty. See anything you like, May?”

            May looked around at the different outfits. Some of them had pieces that looked like dicks in the vaginal region. Hmm… maybe Mistress would like her in one of those? “How about this one?” she asked, pointing at one.

            Beth laid a hand on the back of her head. “Well, I like that concept, but the panty alone doesn’t make much of an outfit. Hmm… how about that one combined with this one?” she pointed up to a design with a short leather skirt and a simple leather bra.

            “Would you like that, Mistress?” May asked.

            “I would. We’ll get you the skirt and top and a nice little harness to hold a dildo inside you.”

            Sam chuckled and stepped up to them. “Sounds good. Come on with me, young lady, and we’ll get you fitted.” He held a hand out to her. May looked back at her Mistress first. “Is it ok, Mistress?” she asked.

            “Go ahead, dear. Be a good girl for Sam, okay?” she patted may softly on the back as Sam kept his hand held out.

            “Ok.” May grabbed the man’s hand and was led out of the room into the back of the shop. “So… are you going to need to take my measurements?” she asked.

            Sam nodded and picked up a loose measuring tape. “Go ahead and take that dress off… May, right? I’ll need to get some really accurate measurements.”

            “O-ok…” May slowly let the dress drop down around her ankles. She stepped out of it, as well as her shoes. “Like this?” she asked, covering her breasts in embarrassment.

            “That’s a good start, but I need you to hold your hands out to your side. Remember, your Mistress said to be a good girl.” He knelt down before her and flipped open a small notebook in his other hand. May slowly lowered her hands, letting the man see her entire body. Even though she used to be a boy, she couldn’t help being embarrassed being eyed up as a girl. Around guys, she felt vulnerable.

            Sam licked his lips, justifying May’s nervousness, and stretched the tape under her breasts, then over the nipples, and made a couple of notes on the page. “You’re a lovely girl.” He complimented. “Your Mistress is a very lucky woman.”

            “Th-thanks.” She answered. “I… I love my Mistress…”

            Sam slid the tape down her arm from the shoulder to her waist, made another note, and nodded. “You’re a good girl. I’m sure you’ll take very good care of her.” He reached around her waist and took another measurement, then over the slight swell of her hips.

            “Umm… don’t you mean the other way around?” she asked.

            “Hmm? Oh, and vice versa, but if I know Beth, you’ll be well trained to serve her within a month.” He chuckled softly and slid the tape from the floor up to her slit, then rubbed lightly at her entrance. The feeling suddenly caused May to try to step back, but she remained where she was. “Umm… what are you doing?” she asked.

            “I’m getting your measurements and checking how wet you are.” He answered. “I’ve got your inseam, now we need to see how big you are inside.” He reached out for a strange, clear dildo that was attached to a cord and a ball at the end. May’s eyes widened and she really did step back this time. “Umm… where exactly are you going to put that?!” she asked.

            “Inside you, May. I need to know how big of a dildo to put on your outfit. Don’t worry, I won’t push it all in.” he grabbed her wrist and pulled her forward again. “Now relax and spread yourself for me. I need to get a good measurement.”

            May slowly nodded and spread her legs wide open. She tried to relax, but the thought of the dildo made her weary. Sam slid it in quickly and smoothly until he felt the shaft press against the back of her walls. May gasped as the shaft slid into her. Sam bent forward and nodded, and then made a note of the dimension. “Alright, now for girth.” He began slowly inflating it by squeezing the ball. “Let me know when it starts hurting.”

            It was pretty big as it was, even though he didn’t begin to inflate it yet. “It’s so big…” she whispered, looking at the cable that ran from the pump to her cunt. Sam kept inflating it slowly and watching her face and her slit to see what her reaction would be. His free hand reached out and petted her gently on the head. “Good girl.” He said.

            May felt the dildo slowly increase in side inside of her. She gasped as she felt her womb expand, making a nice little bulge in her stomach. Her face bore the expression as if she was receiving pleasure from it, and to some extent, she was.

            “Amazing.” Muttered Sam. “Most girls would have been done by now. Hmm… tell me when it starts being too much, okay?” he began inflating the thing faster and reached out to gently run his fingers across the bulge appearing on her belly. May suddenly shivered as she came from the pleasure in her body. It felt unique being filled like this. After a while, however, it began to hurt. “Ah! Ok ok! It’s starting to hurt now!” she cried out. At this point, it looked like she was a few months pregnant.

            Sam’s eye twitched slightly as he stared down at the inflated dildo after pulling the thing out of her. He measured around it and blinked slowly.

            “Beth can’t even take one that big.” He muttered. “Do you want me to make the dildo that goes in you this big, dear?”

            May fell to her knees, gasping for air. She really only let Sam do that once she was feeling pleasure.

            “N-no… I want to have it a little smaller than Mistress’s dick.” She moaned, rubbing her pussy lips again. “I –ah! I don’t want her to be smaller than it! OOOOHHHH!” May came again, her pussy lips dripping wet with cum. Sam licked his lips again and released all the air from the dildo, grinning. “Well, I’ll feel a little inadequate after that, but damned if you didn’t get me going, girl. Now be good and lay back for me.” He began pulling down his pants. May nodded her head and laid back, looking up at the man a bit nervously. Her pussy lips were somehow still tight as they were when she was turned into a girl several hours ago. “What are you going to do?” she asked.

            Sam shoved his pants off, his large shaft springing free, bigger than Beth’s. “I was thinking I’d do this.” He pressed his wrists down over her head and thrust his cock into her like a battering ram, thinking she’d be loose after being stretched, and cried out sharply in lust. May cried out in pleasure and pain. Sam thrust in a little too hard into her, but at least she was lubed up with love juice from her recent orgasms. “Mmm… Aahhh! What are you doing?!” she cried out. “I’m Mistress’s pet!”

            “She shares her pets with me. It’s part of why I’ll make her clothes.” He breathed over her like a bull in heat, and began thrusting faster and deeper into her. “Oh, damn! You’re so tight!”

            The girl cried out in pleasure as she was pumped harder. Her stomach bulged out with each thrust. She came again after a few more thrusts, leaking pussy juice everywhere. Sam groaned with the feel of her pussy walls squeezing his cock and he dug his fingers into her shoulders. His own release washed fast over him as he pumped thick, hot seed up into her small body.

            “Fuck… so good… you should come back and get lots of nice clothes, slave.”

            May lay there, in a state of ecstasy as the man pulled out of her. Finally, she came back to consciousness, and she sat up, the cum spilling out of her. Sam was busy putting his pants back on and looking over his notes briefly. He nodded and waved dismissively at the door. “Ok. You can head on back to your Mistress.”

            May nodded and put her clothes back on, heading back to her Mistress in the shop. “I’m back.” She said. “Is there anything else you want to look at?”

            “No, dear, though I’ve found another nice little treat for you.” She answered. “I’ll show you in the car.” She offered her hand to May, who grabbed it and was led out of the shop and to the car, but not before Sam sent a wink her way.

            “What is it?” she asked, sitting in the passenger seat. Beth sat down in the car and pulled out a leather collar with three D rings placed evenly at the front and sides. Dangling from the front ring was a tag that read “Property of Beth”.

            “Something nice to show other Masters and Mistresses who you belong to.” She answered, smiling darkly.

            “Property of Beth?” May asked, reading the tag. “And… what do you mean by… other masters and Mistresses?”

            “Well, other people keep little pets like you. I’m so proud of you, how could I not show you off?” she pet softly at May’s hair. “Don’t worry, if you don’t want to, you don’t have to play with them.”

            “No… I’ll do what Mistress wants… will you put the collar on me?” she asked. Beth smiled and nodded, then reached out and wrapped the collar around May’s neck and buckled it closed. “It looks lovely on you, pet.” She said. “We’re going to have so much fun together. Well then, where should we go next?”

            “Um, can we go back to my mom?” May asked. “I bet she is worried about me…”

            Beth nodded and started up the car, but paused before pulling out of the alley. “You know, you haven’t told me where your house is.”

            May told her the street name that she lived on. While she said this, she suddenly realized something. “But… my mom’s not going to recognize me… how will we show her that it’s me?”

            “I’m sure she’ll recognize you. You look pretty much the same, dear, just a little more… feminine. And if she doesn’t recognize you, well, I don’t know your old middle name, or her maiden name, or what songs she sang you to sleep with, and I imagine other people don’t either.”

            May nodded her head. “I guess not…” she whispered. “I wonder what she would say about this, though…” She looked up as they drove up to her house. "Here it is." she said. "That house over there.

End of Chapter 2