Bondage Princess May: Boytoy Jay/Chapter 5

Index

• Chapter 1
• Chapter 2
• Chapter 3
• Chapter 4
• Chapter 5

After Jay, Kevin, and Ben cleaned up, Kevin got dressed in a pair of shorts and a tank top and went outside. Meanwhile, Ben got Jay ready for a trip to the clothing store. Since Jay was a very fresh slave for a little over a week now, he didn’t have any clothes to wear, or rather the right kind. Jay knew that he could fit in some of Kevin’s clothes; hell, he was wearing a set right now. But Jennifer insisted that they weren’t appropriate for him.

“Remember, Jay, that when we’re outside of the community, you are to refer me as mom.” Jennifer reminded him as they walked to the car in the garage. She made him sit in the back next to Ben, who was dressed in jeans and a t-shirt. After they buckled in, Ben leaned over and kissed Jay on the lips.

“Now behave yourself, Ben.” Jennifer mildly scolded when she caught him in the act. “We can’t let either of you getting too carried away in the middle of the store.”

Ben nodded his head and sat back up. Jennifer drove the blue BMW X5 out of the garage and carefully up the road out of the community. Jay looked out the window at the beach side with awe. When he was abducted from the foster home nearly a week and a half ago, he was in a large vehicle that was as big as a bus, but it had house stuff inside. His “captors” were very nice to him, and he never once felt fear for his life.

Jay liked this place much better than the foster home he was abducted from. It was a horrible place he wanted to forget as much as possible. The atrocities that happened there will not be discussed here; They have already been the topic for the 11 o’ clock news numerous times over the past decade, and despite the public knowledge about it all, it seems no one has yet to care.

“It’s amazing, isn’t it?” Jennifer asked. Jay snapped out of his trance and looked at her reflection in the rear-view mirror.

“Huh? What?”

“The beach. It’s your first time seeing it, right?”

Jay looked back out at the beach and the spectacular light show of the sun rays reflecting off the turbulent surface.

“It goes on forever.” He replied. “I don’t think I’ve ever seen anything so beautiful before.”

Jennifer smiled at him before focusing back on the road. They continued down the road for several miles until they came to a shopping center in a small town. They parked outside of a Kohl’s store, and when they all got out of the car, Jay could still smell the ocean in the air.

“Mis- I mean mom,” Jay stuttered, feeling a bit strange calling her mom.”What kind of clothes are we getting?”

“Oohh, the best kind for you.” She replied, pressing her hand against his back and ushering him towards the store. Inside the air-conditioned store, Jennifer escorted Jay and Ben down the aisle to the right-side of the store, keeping a firm hand on the square of Jay’s back.

“Uhhh, Mist- I mean mom, the boy’s section is back there.” Jay said, pointing behind him.

“I know, but we’re not dressing you up like a boy, now are we?” Jennifer whispered into his ear. Jay looked back at her with surprised and curious eyes. What did she mean by that? She pushed led him through the aisle of girls clothes and into the changing room.

“Ben, be a dear and find a room for Jay.” she said before heading back out. Ben grabbed Jay and pulled him into the stall normally reserved for disabled people. He seated Jay down on the bench and pulled off the young boy’s clothes. Jay was wearing a simple tight pink thong underneath, which kept his package snug and comfortable. Jennifer came back a few minutes later carrying several dresses in her arms.

“Here, boy. Try these on.” She said, placing them on the bench next to Jay.

“What? What are these?” he asked. “These are girl clothes!”

“I know. Don’t they look adorable?”

“But I can’t wear these! They’re girl’s clothes!” Jay protested.

“Oh? And why is that a problem?” Jennifer gave Jay a calm state, but he could feel the tension from her, which intimidated him into complying with her demand. He picked up the first dress and threw it over his head. Ben helped pull it down over his body and smoothed it out for him. Jay stood up and examined himself in the mirror. He blushed as he realized that, even though this was just the dress, he really did look like a girl!

“Well? What do you think?” Jennifer asked.

“I… I look very pretty.” He replied. “But it feels… very breezy.” He closed his legs, still feeling as though he was still half-naked from the waist down.

“You will get used to it, Jay. Now wait right there while I look for some other things for you to try on.”

For an hour and a half, Jennifer looked for things for Jay to try out, while Ben folded up and sorted the clothes they approved of and didn’t approve of. At the same time, Jennifer added a few bags of thigh-high stockings and panties to the stack. After Ben returned the dresses to the racks outside, they paid for the clothes and made their way back to the community. Jennifer parked inside the garage and she and Ben brought the bags inside the house.

“Good boy, Jay. Now take off those boy clothes. They are nowhere near appropriate for you.” Jennifer said as she and Ben brought the clothes into the house. Jay complied with her orders and removed the shirt and pants one by one until he was wearing only the thigh high stockings and the pink thong. He sat down on the couch patiently, waiting for her next order, if she had any. “Okay, Jay. I don’t have anything else planned for you today,” Jennifer announced. “So I think now would be a good time for you to go outside. Wait here, I have the perfect swimsuit for you.” She left for the bedroom while Ben got the scissors to cut the tags off the clothes. There was a long moment of silence in the room. Ben didn’t talk much, which was more obvious when Jay was alone in the room with him. He was a nice boy and was always good to him, but Jay sometimes just wanted someone to talk to.

“I found it!” Jennifer announced, bringing back the swimsuit. She held it up for Jay to see, and it took a while for him to understand its form. The swimsuit was mostly an organized assortment of strings that would hold it in place on the wearer’s body, but overall, it barely covered anything.

“Wh-w-how am I supposed to wear that?” Jay asked.

“Here, let me help you put it on. It is a little complex.” Jennifer waited for Jay to remove his thong, and she loosened some of the straps and had Jay put his feet through some of the loops. She brought the outfit up his body and tightened the straps around his shoulders. The bra section barely covered his nipples, and the straps converged on the square of his back in an X-shape. The straps were connected by a ring underneath the armpits, and another pair of straps went down his back, which Jennifer pulled down between his legs.

“AHH!” Jay gasped as he felt Jennifer grab his cock. She pulled the end of the strap up from between his legs – as the two straps converged into another ring on his tailbone – which spread his balls apart. On the end of the strap was a loop, and she stuck his cock through the loop and tightened it. The straps on his back pulled on the loop his dick was ensnared in, which caused him to sprout an erection.

“Look at how cute that is!” Jennifer cooed, tapping him lightly on the slit of his cock. “You look just like Mistress when she was your age!”

“What do you want me to do outside, Mistress?” Jay asked.

“Oh, nothing in particular, but I do want you to go around and meet other pets. Show them what a nice boy you are, but remember the rules, Jay. And to make sure you obey those rules, I’m sending Ben to supervise you.”

Ben looked up at the mention of his name.

“Yes, Ben. I’ll take care of the rest. You go and get ready.” Ben nodded his head and left for the bedroom. He returned very quickly wearing a tight black Speedo.

“Now you boys play safe, and be sure to be back before 5:00.” She said to both of them. Ben nodded and grabbed Jay’s hand and led him out the door. Right as they closed the door, the two ran right into Kevin, who smelled of sex and looked a bit wet. He took a good look at Jay and gave a huge grin.

“Hah! That suits you very well, Jay!” he said. “Where you headin’ off to dressed like that?”

“Mistress wants me to go meet the other pets in the community.” Jay explained.

“Heh, well I hope you remember what your rules are.” Kevin said. “I won’t be so good to you if I find out you break the rules.”

“I-I-I will obey the rules, Kevin.” He stammered, shuddering at the thought of Kevin torturing him again like he did yesterday. Kevin walked past them into the house, but not before giving Jay’s ass a gentle squeeze. Ben and Jay left the house and walked down the road to the beach. Again, he was alone with the mute Ben. He really hoped that there were people down at the beach he could talk to.

The rules Kevin and Jennifer mentioned regarded the rules specific to Jay. He learned them all the second day he began to live here. According to the rules, Jay was not allowed to have sex with any girls; only boys, and he could only be on the receiving end. The only exception to this rule was oral sex; he could give and receive oral to anyone. He wasn’t allowed to masturbate; someone else would have to make him cum, and only at their discretion. These were only the major rules. There were other rules that he didn’t commit to memory entirely yet, but he had them written down back at the house.

When Ben and Jay got to the beach, they found that it was empty. Jay looked around disparagingly. It didn’t look like there was anybody here. Ben suddenly tapped him on the shoulder and gestured towards the left of the beach near the sandstone cliff side. Jay followed Ben closely, wondering where he was taking him. When they got close to the face of the cliff, Jay noticed a small fissure on the side of the mountain, which Ben slid through.

“Ben, where are you going?” Jay asked. Ben looked back briefly and gestured him to follow. Jay complied, and as he slid through the fissure, he noticed that the ground and walls started to smooth out, almost like it was dug out by someone. He gasped suddenly as his prick tapped against the sandstone, which made it throb and the erection stiffen further. It was a really tight squeeze, and the lack of any appropriate clothing caused him to scrape up against the rough surface. Several feet into the fissure, the passageway opened up, and there was a small set of stairs and a short length of tunnel. When they both headed down the tunnel, it opened up to a large circular cavern, with benches carved into the sandstone around the entire length. It almost looked like the entrance to one of those fancy outdoor theaters, and Jay and Ben were the entertainment.

Inside the cavern, there was a large crowd of girls, all of them naked. They were either in pairs or groups of three, fondling, hugging, kissing, or grinding, and their passionate moans filled the empty space. The sight made Jay blush, and he hid behind Ben’s larger figure. Ben clapped his hands once to get their attention. A few of the girls looked up to see the two standing there, and they exclaimed in delight.

“Hey look, it’s Ben!” one of them announced, and a good majority of them – mostly the older girls – congregated around Ben and Jay. The rest simply ignored them and continued whatever lewd act they were committing with each other.

“Oh, Ben, I missed you so much!”

“Ben, where were you yesterday? It got wild over here!”

“Ben, who’s your friend?”

The girls bombarded Ben with a bunch of questions, not taking into consideration the fact that he didn’t speak. They obviously knew him, so it wasn’t like they could just fake ignorance.

“So who is the new boy?” The oldest in the group asked. She looked like she was close to 14. “Come on out, we won’t bite… hard.” The rest of the girls giggled as they sized up the two boys. Two of the girls pulled Jay out from behind Ben, and the next thing he knew, half a dozen soft smooth hands were feeling at his body. He felt himself getting pulled away from Ben, who tried to make a grab for him, but got accosted by the oldest girl.

“Ooh, look at how big the boy is getting!” One of the girls cooed, seeing Jay’s boner erect and stiffen.

“That’s insane! He’s nearly as big as Ben!”

“You’re such a lucky boy. Most boys your age aren’t as endowed as you are.”

Jay watched them in horror as they continued to fondle his body. One of the girls stroked his dick while another one cradled his balls in her hand.

“Haaaahhhh!” He moaned, trying to break their grip.

“Nuh uh! We’re not going to let you go just yet. Not until Laura loses her cock virginity to your large shaft!” A young girl, maybe a year younger than Jay, was positioned above him. She covered her face with her hands, blushing heavily at the prospect of letting him enter her body.

“Noo! Stop!” Max shouted. His sudden outburst made the girls pause. The confusion on their face was as subtle as a fireworks display.

“What? What kind of boy would just outright refuse sex with a bunch of girls?” one of them asked. “Are you gay or something?”

“Uhhh, guys?” the oldest girl called over. She was already impaled on his cock and slowly moving her hips back and forth to keep herself aroused.

“What is it, Samantha?” one of the girls asked.

“Ben here just told me that the rules don’t allow Jay to have sex with girls; only boys.”

“WHAT?! That’s a total gyp!” the same girl exclaimed, followed by a chorus of disappointed moans. “Now what are we supposed to do?”

“Wait a minute…” Samantha leaned down over Ben, still grinding her hips. It was very quiet in the cavern, save for the series of moans and the occasional yelp from the younger crowd of girls behind them. After a minute, Samantha sat back up and placed her hands on Ben’s chest.

“Well, apparently the rules prevent Jay from having sex, but not the other way around, if you get what I mean.”

The girls stared at her confusingly, trying to comprehend what she just said. The girl who exchanged words with suddenly had an epiphany, and she grinned mischievously.

“What’s up, Alice?” one of the other girls asked as Alice went to the back of the cavern. She rummaged through a cloth sack sitting on the backmost bench, and she came back holding a dark red double dildo in her hand.

“If Jay can’t fuck us,” she said, pushing one end of the double dildo into her pussy. “Then we’ll just have to fuck Jay!”

Jay’s eyes widened when he saw the girl approaching him, fake cock sticking out of her pussy like it was one of her own. The other girls exclaimed in revelation, and they all got up one by one and went to get a double dildo, too. One of the girls first took Laura over to Ben and Samantha.

“Here, you can have your first with Ben.” She said, sitting Laura down on Ben’s face. Ben held her down by her waist and began eating her out. Laura wriggled her cute butt around and squealed at the sensation of his tongue lapping away at her pussy lips. Meanwhile, the girls were crowding around Jay again, this time sporting double dildos and Feeldoes of various shapes and colors. Alice got between Jay’s legs while two other girls held his arms and legs down. She prodded the tip against his asshole, and slowly pushed it in.

“NNGH!” Jay grunted and instinctively his anal muscles tensed, clenching the dildo. Alice was still able to push it in, however, albeit with a little more effort.

“Wow! He has such a tight grip on the shaft!” Alice exclaimed, wriggling her hips around. “I can barely move!”

“So your Mistress is training you to be a gay boy?” one of the other girls asked, scooting over to Jay’s head. She grabbed the back of his head and pulled him onto her shaft. “Show off your sucking action, then!”

Jay did as he was told and sucked off the dildo, though he wasn’t sure what that would accomplish. The dildo violating his ass was stiff and unyielding, unlike Ben’s softer, but firm cock. However, it was a bit longer, and it was prodding against his sensitive prostate, causing him to arch his back upwards. The other girls crowded around him, each of them stroking their cocks. Two of them grabbed Jay’s hands and made him stroke off their dildos.

“Oohh! I can feel it through the dildo!” The girl Jay was sucking off moaned.

“I know, right?!” Alice sighed, her voice sounding a little shaky. “It’s rubbing so nicely against my clit!”

While the girls were busy having their way with Jay, Ben had his hands full with Samantha and Laura. He tensed as he felt Samantha’s tight pussy lips clenched his cock like a vice. He didn’t cum yet, as he was saving it for Laura. Samantha moved off of him, and he rolled over and picked up Laura in her arms. She was still blushing heavily from being licked in her most personal place. It was wet and very slick with his saliva and her own fluid, perfect and ready for his cock.

“Hyaaaahh! KYAAAAHH!!” Laura squealed as she slowly slid down onto his shaft. Since her Mistress already broke her in, her cherry was already popped, but Ben could tell this was the first cock she had inside her body. He sat down on the stone bench and held her close as he slowly thrust in and out of her. Laura let out little squeaks of pleasure, burying her face into Ben’s chest. From Jay’s position, he could see the affection Ben was giving to Laura. It looked very passionate and warm, and he wondered if that’s what he and Ben looked like together.

Jay’s focus came back to the group as Alice grabbed his little dick and began stroking it. He tried to clamp his legs together, but the girls on either side of him held his legs down and splayed open. As he could do nothing but suck and stroke off the cocks around him, he tried to enjoy it while he could. After all, this was one of the very few times he would probably be allowed around girls, which he admittedly liked. Their bodies were softer, more gentle than the rough strong bodies of boys like Kevin and Ben.

“Mnnhhh! KYAAAAHH!” Alice cried out as she came. Her vaginal muscles clamped the dildo even tighter, keeping them held together even as she tried to pull away. Jay’s tight asshole had a firmer grip on the dildo, especially after her vaginal muscles relaxed after her orgasm, and it popped out of her. Alice lay on the ground, her chest heaving with each breath and trying to recuperate from the blissful rush.

“Oohh wow!” she gasped. “That was incredible! His butt is so tight!”

“Alright, then. I’m next!” the girl Jay was sucking off now moved over between his legs to have a go with him. She grabbed the dildo still embedded in his ass and jerked it back and forth. Jay gasped and cried out in a combination of Heaven and Hell. The dildo was ramming repeatedly against his prostate. He tried to hold himself together, but to no avail, and he blew his whole load all over his chest.

“Woah, look at him go!” the girl between his legs exclaimed, milking his cock of every last drop. She licked the sperm off her hand and pulled the dildo out of Jay’s ass, and pushed in the other end of the dildo that was embedded in her pussy.

On the other side of the cave, Laura was trying to hold it together as well as Ben lay her down on the bench and continued to stab her pussy with his thick shaft. He moaned and grunted as he came in Laura, filling her up with his hot sperm. Laura let out a shaking breath and rubbed her stomach with her hand. She could feel his cum inside her womb, and it made her feel very warm.

“Ben, lift her up.” Samantha said, sitting down on the bench with them. She was stroking the head of a double dildo she slowly pushed into her womanhood. Ben did as he was told and pulled Laura up back into his lap, and already knowing what she had planned for the girl, grabbed her butt cheeks and spread them far apart, exposing her virgin asshole. Samantha pushed the end of the dildo deep into Laura’s ass, being careful not to hurt her. Laura drew in breath sharply and pressed harder into Ben. The dildo was so large! It was spreading her asshole open wider than she could have ever thought possible!

“Oohh! I’M CUMMING!!” Khana, the girl fucking Jay’s asshole now, squealed. Jay panted heavily. After cumming a second time in such a small window, he was exhausted, and his dick ached with every throb. He was done playing. He wanted to rest now, but he couldn’t ask them to stop, since his mouth was still filled up by one of the fake cocks. This torture continued for half an hour longer, with the other three girls having a turn with him. When they were finished, Jay lay in a daze surrounded by the exhausted bodies of the girls. Laura lay on top of Ben, still impaled on his cock and her head in a fog from her double orgasm. Samantha was also incapacitated, sleeping on the bench next to theirs.

After a long rest, Ben slowly pulled Laura off his cock and placed her next to one of the other girls before collecting Jay and carrying him back to the house. The assortment of strings Jennifer called a swimsuit was slipping off his body from the girls’ roughhousing. When Ben returned home, he lay Jay out on Jennifer’s bed and removed the swimsuit.

“Aww, did he get tuckered out?” Jennifer asked, peeking into the room. Ben turned around and nodded his head. He silently stepped out of the room with Jennifer and closed the door behind him.

“So did you two have fun out there?” Ben nodded his head in confirmation. “That’s good. I hope you’re not too tired. I want to have a go with you.” Ben shook his head and ran his hand through his hair. “Damn. Well, your mouth still works, right?” Jennifer led him into the living room, where she sat down on the recliner and spread her legs far apart. Ben didn’t need instructions from here, and he went down between her legs and began eating her out.