Chapter 14

My heart had jumped into my throat when she walked up carrying her tail. I knew she had given me no reason to doubt her love for me, but the scars from both of my ex-wives betraying me were hard to get past. Her smirk at my relief when Katherine explained made it clear she knew what I was thinking, but it didn’t make me feel any better about the pain I had to be causing her.

“You need to stop worrying about her leaving you,” Julien said as we watched the girls getting set up for their yoga class. I saw his faint grin as I turned to him in shock. “I have a lot of practice in reading people. It’s almost a requirement for training new pets, but the looks you both have are easy to read. My stepmother used to get the same look you do whenever father was around the pets. She always worried he would get tired of her and want to start playing with the pets again.”

“The look in her eyes when she sees you is even clearer. Addison looked at me the same way before asking my father to make her my pet,” he told me. “Your kitten would do anything you asked, just to stay by your side. She enjoys her other playmates, but she would never consider leaving you.”

“I’m aware of that on one level, but my doubts still crop up sometimes. I don’t exactly have the greatest track record with women wanting to stick around,” I replied. “She is slowly getting me past it, mostly by always being there when I start to worry, but it has been hard. I’m also a bit worried about being able to spend enough time with her, with the way she’s basically throwing the other pets at me.”

“I wouldn’t worry about that either. Your kitten seems to have no problem letting someone know when she wants attention. From the sound of it, she has been enjoying herself more than you have so far. Just relax and enjoy yourself, I’m sure she’ll let you know if she’s feeling neglected,” he chuckled. “I would be more concerned about my other pets wearing her out. They all seem quite eager to spend time with your girls.”

“Felicia was a bit eager herself,” I laughed in reply. “We should get back to Marta’s schedule for school though. As much as I enjoy listening to music, I know very little about making it.”

Our conversation drifted through the pros and cons of the different classes available for Marta at the conservatory. I was surprised at how much information he had, even when he admitted that Anna had found it for him. We had worked up a viable schedule for her degree program that would have her finished with it in two years unless class availability was changed, and we’re working on possible postgraduate options when our conversation was interrupted.

“Excuse me, Master, but Paige said I would find you here. You told me to come to find you after I got back to discuss what I would be doing.”

I turned to see Marta standing behind us, and I could tell she was a bit anxious. She was looking at Julien, but her eyes kept sliding to me and I could see the hope there.

“Of course, my pet, we were just talking about your future,” Julien told her. “Come have a seat and we will discuss what I expect of you, then I’ll leave it to your new Master to go over his expectations. Alonso has agreed to claim you, so you’ll be returning to Italy with him to continue your schooling.”

Marta’s eyes lit up and she threw herself into my arms. “Thank you so much, I promise I’ll try to be a good pet for you. I know I shouldn’t be asking for favors, but would it be possible to see my family occasionally?”

“We’ll discuss that possibility later,” I told her. “I imagine we can arrange for your family to visit if you do well, but we still have some other things to go over.”

She looked back at Julien and blushed before dropping to her knees between us. “Sorry, Master, I got a little excited when I found out Alonso would be claiming me.”

We were interrupted again as Elizabeth knelt down in front of Marta. “I don’t mean to interrupt, Master, but we have finished our workout and I know Felicia would probably like a shower now. With you being busy, I was hoping I could get permission to wash her for you.”

“I think she would enjoy that,” I replied. “I’ll have to ask you to see if someone can wash Kiera as well, as she’s not allowed to bathe herself either.”

“Of course, Master, I would take care of her myself, but I’m sure someone will volunteer to bathe her while I take care of Felicia,” she said as she got up and walked back to the yard.

I turned back to see Julien’s smirk. “What can I say; I enjoy playing with my pets while I wash them.”

“I completely understand, as I regularly enjoy showering with the pets. I just don’t get to do it every day or I would never get any work done,” he replied as he looked over to Marta. “I only have two rules for you honestly. You’re going to have a lot more freedom than most of my new pets, but you chose to become a pet so I doubt you’ll have any issues following your Master’s directions. Alonso doesn’t particularly like the idea, but he has agreed to punish you if you make it necessary.”

“The main reason I’m sending you to live with Alonso is so you can continue your schooling. I had intended for you to do that here, but it’s not possible at this point,” he explained. “With you being sent out to school, I have high expectations for your performance. We received updates on your marks, and you have been an exceptional student, so keeping your marks above ninety percent should present no difficulty for you. Anything below that will result in a punishment. Do you have any questions about my expectations?”

“No, Master, I’ll do my best to meet your expectations,” Marta replied. “I’m looking forward to being Master Alonso’s pet, so he should have no reason to punish me for not behaving. I can’t promise to keep my grades that high, but I’ll do my best.”

“I’m sure you will, my pet, and I’ll leave you in Alonso’s capable hands now,” Julien said as he stood up. “I need to make sure Anna, Kayla, and Mandy got their office work completed before I start Sonia’s initiation.”

I chuckled as he walked away. Sonia had insisted on being initiated the same way Julien’s other pets were claimed to earn her own outfit. When he had explained that his pets received a spanking on their first day, she had tensed up and I thought she would back down. Julien assured her that the first spanking his pets received was light, and more geared to discover if they enjoyed that form of play than an actual punishment. She looked around the room, realizing all of his pets had been through it and agreed, asking if they could do it this afternoon.

“Umm, Master, did you have rules for me as well,” Marta asked, pulling my attention back to her. “I know you said we would talk about the possibility of my family visiting, and I was kind of wondering what Master Julien meant when he said you were going to claim me. Are you going to be the one who ... Umm ... Fully claims me?”

“If you’re asking if I’ll be the one who makes you a woman, the answer is yes,” I reply. “Although I won’t be claiming you the same way Julien would. His usual schedule would be to have your initial punishment done the first day and then introduce you to vaginal and anal sex the next day. I’m not exactly into spanking, so I would prefer to put that off until after I have taken your virginity. I also won’t be introducing you to anal sex right away, as I’m not as young as he is, and trying to do both today would probably wipe me out for the night.”

“I don’t mind waiting, Master, especially for the spanking part,” she replied. “Felicia got me looking forward to trying anal sex, but I don’t mind waiting. The anticipation will just make it better. You didn’t mention any rules you have for me though.”

“Well, I’m fairly new at this Master business, so I don’t have any rules set up,” I chuckled. “There are a couple of rules I’ll have to enforce, simply because I know what Julien expects of his pets and eventually you’ll have to return to the island. The most obvious being you’ll have to address me as Master. As a new pet, you would normally be punished if you forget, but I’m more likely to just remind you until it becomes a habit.”

“The other one you have experienced to an extent when you gave me a blowjob after I had sex with Periwinkle on the jet. Julien expects his pets to clean their partners after sex. I guess the only real rules I will have for you are basic stuff. What you are wearing now will be fine for around the house, but we will have to get you a tail. I also expect you to take care of your basic grooming, although I will enjoy helping you with that regularly, I won’t have time to do it every day as Felicia and Kiera are not allowed to bathe themselves.”

“I actually have a small plug inside me now, Master,” she replied. “I was told Katherine would have a couple of outfits and my tail ready for me soon, but I should start wearing the plug to get used to it. It’s a little uncomfortable, but not bad. I’m more excited about you claiming me. I guess we’re waiting for your other pets to join us before we get to start that though.”

I could hear the disappointment in her voice as she thought we would have an audience for her first time and had to correct her. “We’re waiting for them, but they won’t be joining us. Sonia is going to be with Julien for a bit, and Felicia will be taking Kiera out so we have some time alone. We just need to see if they need anything before we go back to our cabin.”

“We should address your other request while we wait for them though. I don’t see an issue with your family coming to visit you, as long as they arrange it ahead of time,” I explain. “You need to make sure they understand that you’re still a pet though, and the fact that you’re in Italy instead of the island doesn’t mean you’ll be coming home to them.”

“I’ll make sure it’s clear to them before I invite them to visit. My parents weren’t exactly happy with my decision, but they did accept it. They should be happy that they can at least visit me, as they weren’t expecting to see me again for a few years. I think our wait is over though,” she said as Felicia and Kiera walked up.

“Excuse me, Master, Sonia wanted me to tell you she would be busy for a while, but we should go on with our plans without her,” Kiera said. “If you were serious about not wanting my sulky, I would like to return it to the Stables, but I was going to have Felicia and Sonia take turns riding on the way so you had alone time with Marta. Sonia said she didn’t mind missing it and would see us in the courtyard when we got back, so I was going to take Felicia for a ride then see if one of the trainers can bring us back if that’s alright with you.”

“That’s fine, my dear, we can get your harness and bridle on, then get you hooked up to the sulky before I take Marta back to our cabin. Are you going to be alright making the trip though,” I asked. “You did say you had a hard time with the sulky because you were so small.”

“I appreciate that you’re concerned for me, Master, but it will be one of the easiest trips I’ve made. When you told me it was my choice this morning, I had to think about it as I’m not really used to having a choice,” she told me. “That was when I decided that I did want to take them for a ride. I never thought I would have a Master who gave me the freedom to make my own decisions, and they were the ones who chose me to be your pony, so I wanted to thank them.”

I glanced over and saw Felicia was dressed, so I smiled up at Kiera. “Very well, little pony; let’s get you ready to take my kitten for a ride.”

Kiera pranced ahead of us excitedly as Marta and Felicia curled up against me for the walk back to the cabin. It only took a couple of minutes to get her harness and bridle on before we were back out the door. On the way to the trainer’s cabin, Kiera slipped the bit out of her mouth and looked back at me.

“Master, I thought I should ask before I go to the stables. With Felicia getting a larger plug for her tail, did you wish for me to ask for a larger one as well,” she asked. “My current one is barely larger than the one she had, but I know they have larger ones available.”

“Felicia is getting a larger plug because she enjoys anal sex and the larger plug will stimulate her more,” I explained. “I know the ponies are never taken that way, so I’m not sure you would feel the same way. We should probably wait and see if you enjoy that kind of stimulation before we look into a larger plug for you.”

That shy smile came back and she blushed a bit as she replied. “I know I enjoy the stimulation, Master. I have never had anal sex, but I have always enjoyed having my tail in and some of the trainers have started playing with our tails during breeding. It always makes me cum harder, so I think I would like having a larger plug.”

“You should have lead with that, little pony,” I chuckled. “If you feel you would enjoy it, of course, I want you to have a larger plug, but it will be the only thing in your bottom until after we return home. I want you to meet Sonia’s husband. He’s going to be one of your lovers, but I would like you to consider allowing him to take your anal virginity as well.”

“I don’t mind waiting, Master, but I’m a bit confused,” Kiera replied as I started setting up her sulky. “We’re not supposed to know about it, but the trainers all get excited when they get a virgin. Did you not want to be the first man to have my ass; I thought you said it was sexy?”

“You do have a very sexy ass, and I would love to be your first, but I don’t want to be greedy,” I explained. “Sonia wanted to give me her anal virginity, and she convinced her husband to go along with it. He was very considerate of her desires, and I wanted to thank him for the beautiful gift they gave me. I won’t be taking either you or Marta’s anal virginity until after we return home, because I hope one of you will be comfortable enough with him to allow him to be your first. The final decision will be up to the two of you, but I wanted to leave the option open.”

“So you would like one of us to offer him our anal virginity because you got to take his wife’s, but you won’t be upset if we can’t,” Marta asked. “You’re making it our decision because you know we would agree if you asked or told us to do it.”

“That’s exactly it, my pet. I don’t wish to force you into something you’re not comfortable with,” I replied. “The same way I told Kiera I wouldn’t make her pull the sulky again and she had to decide if she wanted to offer the girls a ride.”

“Speaking of rides, come here, little kitten, and take your seat,” I said, holding my hand out to Felicia. She stepped into my arms and kissed me, rubbing her lithe body against mine. Pulling back from the kiss, she licked my cheek before setting back into the sulky and gingerly taking her seat.

I stepped up to Kiera and kissed her before stroking my finger along her cheek. “Will the trainers at the Stables give you any problems, my dear? Should I have one of the trainers here call ahead?”

“No, Master, by now they’ll all know that you’re my new Master. One of them will release me to speak as soon as I arrive so I can relay your instructions,” Kiera told me. “I know I don’t need to wait, but it will be easier than explaining and make me more comfortable. There should be no problems returning the sulky or getting my new tail, and we should be back in the courtyard in about an hour.”

“Very well, my pet, have a fun trip, and I’ll see both of you in the courtyard later,” I told her as I patted her pert little bottom. She let out a quiet whinny before slipping the bit back into her mouth and prancing off, pulling my kitten behind her.

Marta stepped up and took my arm as we watched them leave. “Kiera is beautiful, Master; will I be playing with her as well when I go home with you?”

“Yes, I guess that would be the only other expectation I have for you. You seem eager to explore your sexuality, so I doubt you’ll object,” I told her as I started leading her back to the cabin. “Once we return home, and the question of your anal virginity is resolved, I expect you to give yourself freely to a select group of people. My home has turned in to a sexually open place and most of your future lovers are living in the house. You are already familiar with Felicia and Sonia, as well as Kiera. Sonia’s husband and father also live with us and will be two of your lovers, as well as her grandmother, who it is safe to say won’t be.”

“Her entire family lives with you,” she asked, a bit confused.

“It’s a long story, but basically they all work for me now. Sonia is my housekeeper, her husband is the groundskeeper, her father is my driver and her grandmother is currently the cook. It started with her father almost thirty years ago and over the years as they needed help, I ended up hiring all of them, but they’re more like my family now,” I explained. “I’m sure you’ll hear all the stories over time, but I should tell you about the rest of our group.”

“Felicia’s son and daughter-in-law came to visit us over Christmas. Well, they came to visit Felicia, but were unaware that she had become my kitten and ended up staying with us,” I told her with a grin, remembering their visit. “One of the reasons they were visiting was to tell Felicia that they were moving back to Bari this summer. Her son is a teacher and was offered a position at one of the local colleges starting next year. His wife is a modeling agent but does most of her work over the phone and online so she can work from anywhere. With their son getting ready to move out on his own now, they wanted to be closer to Felicia, so he accepted the position. I was going to offer them the guest house for as long as they wish to use it.”

“That is very nice of you to let her family stay with you, Master,” she said hesitantly as we entered the cabin and she sat down on the bed. “I don’t know how to ask this, as it’s a delicate subject, so I will just come out and say it. It sounds like there are some unusually close family relationships in your home, will I be expected to be that close to my family?”

I could feel the discomfort coming off her in waves and had to clarify. “It’s a delicate subject for most, and I can see you’re not comfortable with it. Simply stated, no, I don’t expect you to have sex with your family. Sonia and her father are close but have no interest in that kind of relationship. Felicia wanted to initiate a more intimate relationship with her son and daughter-in-law. I told her I would support her decision, but it was entirely her choice.”

“Thank you, Master,” she said with a sigh of relief. “I love my parents, but I don’t really want to get to know them like that. I guess I just assumed that Sonia and her father were sexually involved from the way it was described and thought you would expect the same from me when my family came to visit.”

“No, that’s one of those decisions I would never make for you,” I replied. “You won’t have much choice on who your lovers will be, but that one will be completely up to you.”

“I won’t object to any other lovers you wish to give me to, but that one would just be too weird,” she told me as she glanced around the room. “I guess I do have one other question though. Master, were you planning to breed me? I only ask because I’m not on any kind of birth control yet and I don’t see any condoms.”

“Not for a couple of years as we want you to finish your degree before you get pregnant, and we will be getting you on birth control before we leave the island. I’ll probably take you in tomorrow morning,” I told her. “I imagine you are asking because you don’t want to wait to lose your virginity, but you also don’t want to take the chance you could get pregnant?”

She blushed a bit as she nodded, causing me to laugh. “Don’t worry my pet; I can’t get you pregnant because I’m sterile. That’s one of the reason’s Sonia’s so eager to get Kiera home. I can’t have my own children, so she plans on her and Kiera giving me several children to dote on.”

“I wouldn’t mind bearing a child for you, Master, even if you weren’t the father. I was just worried about being able to keep my grades up to the level Master Julien expects,” she replied. “We can worry about it after I finish my degree, but maybe we can spend the time until then practicing?”

I could see the eagerness in her eyes as she pulled the ends of the little bow between her breasts. It was the only thing holding the flimsy wisp of lace on her body, and as it came undone, she pushed the garment off her shoulders exposing her perfect little breasts.

“I believe you’ll get plenty of opportunities to practice, my pet. I’m sure both Bernardo and Teodoro will be begging for a chance to play with you once they see your luscious little body,” I told her as I slipped my shorts off.

Her hands went straight to my cock as she gazed up at me with her big brown eyes. “May I start with what I’m familiar with first, Master? I loved the feeling of your cock in my mouth and the taste of your cum I got when we were on the plane. I would like to try to do it all by myself this time.”

Remembering her first blowjob, I was tempted, but looked down and shook my head. “You have no idea how tempting that offer is, my dear, but I want to make today all about your pleasure. I know it’s going to hurt when I take your cherry, so I want to make sure you’re as ready as you can be. Just lay back and let me enjoy you for now.”

Her eyes lit up as she laid back on the bed, stretching her hands above her head and arching her back to present her breasts to me. Their perfect half-orange shape held even with her flat on her back, and her hard, prominent nipples were as big around as my fingertip, sticking up half an inch from her silver dollar sized areola.

She moaned when I bent down and ran my tongue around that delightful point before sucking it into my mouth. I had been dying to get my lips on her nipples since she first undressed on the plane in Rome, and I had tried on that first day after lunch, but she had begged me to stop. She admitted that her nipples were extremely sensitive and my kitten had made her climax just sucking on them but if I did it, she would want more than she was allowed to have.

I was enough of a gentleman to stop at the time, but her body was being freely offered to me now and I wanted her burning up with desire before I split her virgin flesh open. With the rest of the afternoon to play, I took my time licking, sucking, nibbling and pinching her hard nubs. Taking my time to experiment, I found she responded best to either a light tracing around her areola or my teeth sinking into her nipple and pulling it away from her body.

After pushing her through a couple of orgasms just playing with her breasts, she was begging for more and I started kissing my way down her body. The heady aroma of her arousal was filling the cabin and wanted to run my tongue over her maidenhead one last time as I savored the sweet, tangy flavor of her virgin pussy. I doubted her taste would change, but I found that thin barrier highly erotic.

She spread her legs wider as I moved between them, offering me access to her most intimate areas. Running my tongue over her puffy outer lips, and noticing how wet they were, put a smile on my face. Light pressure from my fingers on the sides of her slit opened her up, exposing the object of my desires.

I ran my tongue around her inside of her lips before tracing over her maidenhead to the small opening that led deeper. It was so delicate that even a strong lick would have ruptured it. I wondered if that would be easier on her but knew that was not what she desired. I just hoped that it being so thin would make it less painful on her when I did take her.

I kissed my way back up her body and her arms settled around my neck as she looked up into my eyes. “Is it finally time to get rid of that little piece of skin you are so fascinated with, Master? I almost wish I could keep it, just to make you happy, but I want to feel you inside of me more. I’ll try to find other things for you to be fascinated with.”

“Every part of you is fascinating, my pet, but yours is the first virgin pussy I’ve ever seen. I promise I’ll be just as fascinated with it after I have had you,” I replied as I ran the head of my cock over her hard clit. “I’m just a bit awed that I get to be the first man to fully enjoy your beautiful body.”

“When you were in picking out your pony, you remember how happy I was when you came out? That was because Elizabeth and Amanda had just told me that their Master was going to offer me to you,” she moaned as I continued dragging the head of my cock over her swollen pussy lips. “I was excited by the thought of living with you and Felicia because I had so much fun with you both, but more excited by the idea that you would be the one to make me a woman finally. I’m more than ready for you. Please, Master, don’t make me wait anymore.”

I could hear the pleading tone on her voice and the head of my cock was thoroughly coated in her juices as I pushed it between her lips. She winced when I felt that thin membrane tear, allowing me deeper access to her body. I stopped with just the head inside of her, trying to allow her a moment to adjust when her ankles locked behind my back and pulled me deeper.

“I need you all the way inside of me, Master,” she moaned. Not wanting to disappoint, I slowly pushed inside of her, marveling at how tight she was until I felt the faint patch of hair over her pussy ticking my groin.

“So much better than my fantasies,” she murmured before opening her eyes and looking up at me. “That didn’t hurt nearly as bad as I thought it would. Just a bit when you first started, and it’s a little sore right at the entrance, but you feel amazing inside of me, Master. If you start off slowly, I should be okay.”

I nodded as I started rocking my hips, giving her slow, shallow strokes. She was so tight that I didn’t think I could go much faster even if I wanted to. Keeping up the slow strokes, I felt her pussy go from almost painfully tight to deliciously snug after a few minutes, so I started taking longer strokes.

Her pleasured moans told me she was enjoying the greater stimulation, but the velvety grip of her pussy was pushing me to climax far faster than I would have imagined. Balancing myself on one elbow, I slid my other hand up her body to grasp her breast. Rolling her nipple between my fingers, I pinched and pulled it away from her body.

Her sudden gasp turned into a low sultry moan as her already tight pussy clamped down on my cock like a vise. I stopped, unable to move for fear of hurting her, but the intense pressure helped stave off my climax.

“Oh fuck that was good,” she moaned as she came down from her orgasmic high. She had relaxed around me, so I started stroking into her again when I saw her wince and stopped.

“Are you alright, my dear,” I asked. “Would you like me to stop?”

“I’m sorry, Master, but I’m really sore now,” she said, almost in tears. “It was feeling really good, and that was the most intense orgasm I’ve ever had, but it’s really aching right at the entrance of my pussy now.”

She groaned as I slowly pulled out of her and glanced down, noticing there was very little blood. “I don’t think you should be this sore so soon. I’ll ask if Steven can check you tonight, just to make sure I didn’t tear something. Going from a little sore to intense pain is not normal.”

I saw her blush suddenly and look away. “I may have understated how sore I was earlier, Master. It just felt too good to stop. There wasn’t much pain when you took my cherry, but you really stretched me out. It doesn’t look like I bled much, so I think it was just more than I was ready for. Can we wait until tomorrow, and mention it to the doctor if I don’t feel better? I have to see him for my birth control anyway, and it’s a lot less sore now that you’ve pulled out.”

“If you are sure it’s not hurting too much we can wait until your appointment tomorrow morning, but I want you to have a full exam when we go in,” I told her as I settled on the bed next to her. “I don’t think I’m big enough to have put you in that much pain.”

She smiled as she curled up against me and reached down to stroke my cock. “I don’t have a huge pool to base comparisons off of, but your cock is the thickest one I have seen. I can’t even get my fingers all the way around it and I could with the men on the jet. You just need to go easy on me the first few times and stretch me out until I can take you easier. I need to take care of you now though because I feel bad that you didn’t get to cum with me.”

She slid down my body and started licking her juices off my cock before crawling between my legs and smiling up at me. “I’m supposed to clean you up after sex anyway, and I would be even more embarrassed if you came in here to take my virginity, then walked out with a hard-on still.”

Unlike her first attempt, there was no hesitation as she quickly engulfed the head of my cock. I groaned when her cheeks caved in and I could feel her tongue fluttering along the underside of my cock. After a minute of steadily bobbing over the top half of my cock, her right hand came up to stroke me as she looked up at me again.

“I got some advice from Amanda,” she told me. “I want to try some of the things she mentioned so just lay back and enjoy it while I experiment a bit.”