Virgin, Slave, Nanny, Lover Pt. 11

I breathed a sigh of relief at hearing there would be no more anal. I stood as Jorge knelt before me and licked my not-quite-erect cock. I didn't want this to happen, but part of me rebelled as I desperately needed relief from the painful frustration of wearing a cock cage. The thought crossed my mind that he really was cute, and I could enjoy having a cute feminine persona suck me off, even if (s)he was in a man's body. I focused on imagining he was a woman. As soon as he took my cock into his mouth, I rapidly engorged the rest of the way.

Jorge pulled back, "See, he really does like me," before diving back onto my cock. Fuck, his technique was perfect. Better than any woman I've ever met. I moaned in pleasure. He was doing things to my cock that no one had ever done before, making me feel things I'd never felt. I couldn't help myself, "Yes, fuck yes, just like that," I whimpered, "Please don't stop. Please."

I feared he would stop and leave me frustrated simply because I was a slave, and he could. But he didn't. He kept going, driving me insane with exquisite pleasure. "Master, I'm going to cum." To my shock and delight, he doubled down on what he was doing as waves of pleasure crashed over me. My whole body juddered as I unloaded two days' worth of jism into his eager mouth.

He cleaned me off, and I collapsed to my knees. "Thank you, Master, that was amazing. You have an incredible talent."

Mistress Larissa looked horrified at my reaction. Master David, apparently deciding I had had enough, asked Larissa to send me to my room so I could process what had happened. I wished Mistress Larissa hadn't been in the room to see my shame begging Jorge to keep going.

I lay on my bed, suddenly overcome with anxiety and guilt. I had loved having a gay guy give me a blowjob. So what the hell did that mean for my sexuality? Was I Bi? One of my lesbian friends had told me every human being was Bi; some were 99% one way and others 99% the other way, but we were all Bi. But a gay friend had told me that there was no such thing as a Bisexual male; there were only men on the way to being gay who hadn't admitted it yet.

Then thoughts of Rocio came flooding back, and the sense of my betrayal overwhelmed me. Would she think less of me if she found out I'd enjoyed it? See me as a sissy? Would it put her off marriage to me since she was so pure in heart? I was so fucking confused; I had no idea what to feel.

That evening, Larissa briefly unlocked the door to my room and gave me a bowl of kibble and, to my great surprise, a blanket to keep me warm. I guess I had earned it. She left without saying anything. I was happy to have a way to keep warm but stopped short of feeling gratitude; she was just a Mistress I had to please to avoid pain and be released as soon as possible.

The following day, I gave her oral pleasure and then made her breakfast as usual; I was glad she didn't mention the previous day's events, as I was far from ready to talk about it. What was different was that I was allowed a mug of coffee. I guess this was another perk my obedience had earned. For that, I did feel some gratitude. However, it also made me wonder if she felt guilty over what she'd done to me yesterday.

That evening, she told me, "Slave, do you remember that David recommended that you be sent to a boot camp for a week to break you in properly as a slave?"

I nodded even as my heart fell and turned to ice. Larissa had no idea with whom she was dealing. She would eventually have to release me, even if she kept me the entire three years, and she had no idea the damage I could legally inflict on her as a billionaire. I could get her mortgage foreclosed and probably had enough networking contacts to get her fired. She would end up being enslaved if she didn't release me on time.

Larissa continued, "I phoned around to get advice and check availability. I'm sending you to a camp in the Blue Ridge mountains for a week; by the time you return, you will be able to pleasure my male guests with willingness and skill. Since you expected to be manumitted on Saturday, I thought that would be the most appropriate day for you to be shipped in a poodle crate to the boot camp. This is to help you understand that you are my property until the screwed-up sale is rectified."

"I expect you to return with a natural-born slave's subservience and eagerness to please. But, if you don't give up these foolish notions of being sent back to your sister before you've learnt your lesson, I will send you back to boot camp as often as needed until you have learnt them."

"To drive your legal status home to you, you will visit a tattoo parlour to be pierced for a Prince Charlie ring on the way to boot camp. They will send you on with one of the cock cages that attach to a Charlie ring; they hold the cock more painfully in place when you try to get an erection. Having a slave pierced is important in reinforcing that they have no control over their bodies."

"The deciding factor in sending you away was that I have been investigating your company's handling of slaves. I was appalled to find out you use native American kennels to avoid obeying the strict Massachusetts state slave codes. A couple of my High School friends were destroyed by bad slave owners; I've seen what happens when slaves are not treated like human beings. Maybe once you've been through boot camp, you'll understand that you need to make drastic changes to how your company treats its slaves."

I wanted to object; however, my walk around the kennels the day before signing the FINO contract had left me wary. I hated being treated the way Larissa had treated me, and there were similarities to how I treated my slaves. So I resolved to investigate building new corporate kennels when I returned to treat our slaves more humanely.

"One final thing, I have to go out of town overnight tomorrow, and I don't want to leave you locked in your room for 36 hours. So Maddy will arrive at 5 pm and take you home to be kenneled at her house. She'll bring you back sometime the following morning."

That night there were further changes in my schedule. Instead of riding a dildo gag or a strap-on tied over my cock cage, she unlocked my cage and rode my cock as Maddy had done on Friday night. The release of pressure from my balls was very welcome. No explanation was given as to why my conditions had changed for the better so much, and I knew not to ask.

***

Alan:

Mistress Maddy arrived, as promised, at 5 pm and took me to her house. Larissa had said I would be kenneled there, so I assumed she had a slave crate for me to sleep in. Instead, when we arrived, she took me to the master bedroom.

"Slave, my husband is out of town for a week, so you will take me on a date tonight. You are roughly the same size as him. First, have a shower; there are towels in the linen closet in the hallway. Then look through his clothes and find something suitable to wear. I checked with my insurance agent; he said that as a short-term FINO, you can drive my car. We have a reservation at L'Opussum at 6:45 pm. Tonight's special is Osso Bucco, which is one of my favourite dishes."

She left the room; I was confused by her behaviour. Of course, as a slave, I could not refuse her directives, but I also didn't want to have an angry husband coming after me at a later date. The shower was luxurious, a definite step up from Larissa's bathroom and using a kitchen skrubby sponge. I knew Mistress Maddy's husband was wealthy because he'd sent her to White Brier for a year, but this was opulent even by my standards.

I came down wearing slacks and an Armani jacket over a dress shirt with no tie and undone top button. The jacket fit precisely over my shoulders, but the chest was tailored for a more robust torso. Nevertheless, I felt excellent, like a man among men, dressed appropriately. After ten days as a naked slave boy, it was exhilarating. However, I had to keep it from going to my head. Regardless of the situation, I was a slave boy and needed to keep that in mind.

"Is this acceptable, Mistress?" I asked.

"Almost perfect; I know Larissa wants to keep your identity a secret, but there is no way you can take me out to a posh restaurant while wearing a BDSM leather hood! The photos would be all over social media within an hour."

She unlocked and removed it.

"Mistress, please, what if someone recognises this slave wearing a slave collar and photographs me? I'll be ruined."

"Well, we could claim you like BDSM games, and you are playing submissive to my dominatrix tonight, or would that be a bigger scandal?" She snickered. "As an ultra-short-term FINO, I think I can get away with removing your collar for the evening. It's not technically legal, but there is no way for anyone to know. Better still, change into a turtle neck, so no one knows if you are collared; that way, we are both protected."

She unlocked my collar, and I got changed again.

"There! Much better! Allons-y." She passed me the keys to her Lexus. When we got there, she directed me to use the valet parking; I offered her my arm like a true gentleman, and we walked in. The restaurant smelt terrific. It made me remember vacations in the south of France with Freja.

The memory was bittersweet. Nothing about falling in love with Rocio would ever quench the pain of Freja's death. Every day I grieved that my girls were growing up without their biological mother there to celebrate each milestone. Unless you've lost a spouse, it's hard to understand how two women can simultaneously occupy one's heart. However, my dead wife was no threat to Rocio as she simply wasn't there, and I knew Rocio made both of my girls feel loved in a unique way; she already shared a real connection with them.

We settled down, and Mistress Maddy directed me to order a bottle of red wine without waiting to see what we would eat. Knowing she would probably have Osso Bucco, I picked the 2010 La Gaffliére.

"Mistress, this slave is unsure of the rules. Does this slave have permission to chat normally over dinner, or am I still in slave mode?"

She snickered, "It won't be much of a date if you are using slave speech. Until we get home, you are my date, not my slave. So flirt with me and make me feel attractive. And no talk of Mistress, my name is Maddy. To keep the air of mystery, I'll call you Alexandre, you know, the author of the man in the iron mask."

I had to smile at that, "Hmm, I like the idea of Alexandre Dumas for my mysterious persona; it fits. Maddy, since we've already had sex, I'm guessing we will have more tonight."

"Much more," she quickly interjected.

"I'd love to flirt with you, but are you sure your husband won't come after me later if he finds out?"

She burst out laughing, "Finds out? That's funny. It was Gerald's idea. He knew Larissa was breaking in a new slave and that she was unlikely to teach a slave to enjoy slave sex, leading to a miserable slave. So he suggested I help out with your training; besides, he occasionally uses pleasure sluts when he's away on business, so it's only fair. Sex with slaves isn't cheating."

"Is there anything, in particular, you want to talk about?"

"Yes. Yes, there is. I disagree with what Larissa is doing to you. After you asked about White Brier last Friday, I talked to Larissa at length and got the whole story. She told me you signed a two-week FINO to your sister in return for being allowed to take your fiancée's virginity. I gather your sister owns your fiancée until the FINO is completed; then, ownership will be transferred to you. I also gathered that she is your children's nanny, and you are a widower. Is that right?"

I nodded.

"Larissa told me about the screwup at the slave processing centre. I had a huge fight with her over her intention to keep you longer than the two-week FINO you signed. I think it is immoral and likely illegal, but since she has the invoice stating she bought a slave with your SIN for three years, it will be difficult to get her to budge. She told me she plans to keep you for three months to teach you humility. I asked why that was so important to her, and she implied you triggered bad memories of past hurt. Is that also true?"

"Maddy, I own one of the major high-tech companies on the East Coast. She's incensed at how my company treats its corporate slaves. She's also angry that her father and brother suffered at the hands of insensitive CEOs offshoring jobs. So, yes, she really has it in for me. It seems to be personal for her to humble me."

"I understand that I need to ameliorate how I treat my corporate slaves; that much is obvious. They will be a priority as soon as I am freed. The irony is that for the first week, she treated me worse than our corporate slaves are treated; at least ours get blankets to stay warm at night to sleep well because tired slaves are not productive. They also get coffee in the morning to help them get up and be productive for their owners."

"The room she has me in is unheated; even with a blanket, I'm so cold I have trouble sleeping. For the first week, I got up and made her a pot of coffee; she then sat there tantalising me with it while I drank cold water from a dog bowl on the floor."

Maddy reached out and took my hand, "I'm sorry about your conditions, and I'm glad you've learnt something. I'll talk to her again about how she's treating you."

She talked at length about how she got enslaved, how her now husband bought her three-year indenture to be a pleasure slut. In the beginning, she was expected to have sex with all his friends, and sometimes it was literally a gangbang. If they went to a restaurant or a club, she was expected to pleasure everyone in his group. But, gradually, he developed feelings for her and started to dial back on letting others use her. It wasn't long before he told his friends he would no longer share her.

"When he told me I was going to White Brier Finishing School, I had no idea what to expect. I feared the worst of being turned into a sex-crazed bimbo. But WBFS isn't like that; the only sex students are permitted to have is with other girls, their owners, or their future husbands. It is run like a liberal arts college, and you graduate with a recognised degree."

"A month before I graduated, he proposed. He said I could be manumitted and we could get married. Or if I really didn't want him, I would serve the last year of my indenture as his pleasure slut and be available to all his friends again. I was already in love with him by then, and he knew it: his visits to the college to see me had been so romantic, and the sex had been mind-blowing. I didn't need a moment's thought to accept his proposal. Three months later, we were married." She snickered, "I needed those three months for my graduation brand to heal fully."

I asked her about sending Rocio to get a Master's degree there, but it would mean the children would lose their nanny for a year. She told me that she was grateful for all White Brier had given her, but it would be wrong to take the children's nanny away when they had already lost their mother. I concurred.

After dessert, Maddy told me it was time to go home and be her sex slave for the night. As soon as we entered the door, her tone changed, "Slave, strip but keep your boxer-briefs on!" The date was over, and I was back in slave mode.

She led me naked up to the master bedroom and turned the chair at her makeup table around, and told me to sit. Then, she handcuffed my hands behind my back and tied my ankles to the chair legs. Then, she said to my utter surprise and delight, "Let me show you, slave boy, what a White Brier Consort can do."

She lined up the stripper song, 'My Neck, My Back' by Khia, and hit play:

All you ladies pop your pussy like this

Shake your body, don't stop, don't miss

Still fully dressed, she did the most sensuous pussy-popping pelvic thrusts I've ever seen: her hips gyrated in circles even as they thrust forward. All I could imagine was her hips doing that on my cock. I thought I'd been turned on talking to her in the restaurant, but now my cock was straining to fill even further. Her body was fluidity in motion; I could only guess that she still did slave yoga religiously.

She undid and shed her skirt in a single well-practised motion and stepped out to show a lacy black thong beneath a very lacy black garter belt.

Do it now, lick it good

Suck this pussy just like you should

Her fingers slipped inside her thong, and she frigged herself in time with the music, alternating, palming her mons and making a V over her clit. It was mesmerising. For the phrase, suck this pussy, she pulled her fingers out of her thong and sucked them into her mouth, mimicking fellatio.

She spun around and started twerking for:

My neck, my back

Lick my pussy and my crack

She removed her top, revealing a matching black lace demi-bra, and spun around for the phrase, all over your face as she rocked her hips like she was riding a guy's mouth and moaned loudly.

All over your face and stuff

Slow head, show me so much love

The best head comes from a thug

At slow head, she slowed right now to half-time to the music, stood over my lap, and continued her sensuous imitation of a woman riding a man's face (soon to be my face, I guess; I couldn't wait). As her hips continued to roll suppley back and forth, she flicked off her bra in another well-practised move and started playing with her nipples. Her moans turned to mewls, and her face to ecstasy. She was a superb actress; this was an Oscar-worthy lap dance.

The dick good, dick big and long

Slow fucking 'til the crack of dawn

She squatted lower over my hip and started rubbing her vulva (still beneath her thong) up and down the underside of my turgid cock. I groaned; she could bring me off like this far too soon. She saw my panicked expression, smirked at the power she had over me, turned around, and started using her butt to run my cock. Just when I thought I couldn't take any more, she stopped.

She put her foot on my lap, pressing on my balls before lifting her garter to my face. Then, she said very huskily, "If you want me tonight, slave boy, you need to remove this." I rattled my handcuffs. She giggled, "No, with your teeth."

I don't know if you've ever tried removing a woman's garter belt with your teeth, but it is damned tricky; but, my motivation was even stronger. I was under orders from my fiancée to enjoy this as much as possible, and this was what I needed after ten days with Larissa.

I eventually got all four clips open, but I'm not convinced I didn't damage them in the process. She peeled both stockings off seductively. Then, after undoing the hook on her garter belt, she stood straddling me and told me to pull her belt down with my teeth. I'd be throwing $100 bills at her by now if this was a strip club.

"Now, my thong," she squatted on my thighs and thrust her pussy into my face. I grabbed the lace between my teeth as gently as possible and pulled as she slowly stood up. Mercifully she was slim and only 5' 6", so her weight was manageable - even so, my thighs were not used to the pressure. She squatted down again and leaned forward to kiss me. With all her weight on me, her dominance was complete, and I was at her mercy (never mind that my hands were still cuffed behind my back).

She dropped down and pulled off my underwear. She was sitting on my lap and resumed lap dancing as my cock rode the slit in her naked vulva lubricating further with each stroke. Just when I thought she'd impale my cock and ride me to orgasm, she stopped and removed something from her bottom drawer. It was an adjustable cock ring. She slipped it over my cock and behind my ballsack before cinching the tie hard.