Chapter 10: Orgy.
I have no idea how long it was until the van stopped. The assorted tracks of females moaning blurred into each other, and I wasn’t able to fully pay attention to what was happening.
Eventually, the van came to a stop, and Donna once again got into the back. Instead of releasing me, however, she merely sat on my chest and grabbed the MP3 player. She wore a wicked grin as she stopped the “music” I’d been listening to.
Much to my surprise, Donna reached down and removed my gag, although with the headphones on, talking seemed pointless. She then flipped her latex skirt up over my face. I felt her hand push down over my nose, and as I opened my mouth wide to breathe, she positioned her pussy on it and sat down.
She released my nose then and slid the skirt back, so that she was looking in my eyes.
All of a sudden, I heard Donna’s voice coming through the headphones. She’d recorded a track just for this?
“Sweetie, remember when I said that I had a fantasy I’d been dreaming about for years? Well, I’ve had guys lick my boots before, and I’ve certainly had guys eat me out. So those weren’t exactly fantasies, where they?”
Even though there was a pause, I couldn’t answer. I suspected that her previous experiences hadn’t been quite as bondage-heavy — even at twice Randi’s age, Donna seemed more innocent — but I was more concerned with what she had in mind now.
“Jane said that you’d also drank her pee. That’s one of my longest-held fantasies.”
I wanted to protest, since yesterday, I’d at least had a sponge gag to control the flow. Here, I had Donna already sitting on my mouth. There was nothing I could do.
I felt Donna’s thighs contract, and a steady steam of piss hit me. After a few seconds, my mouth was nearly full, and Donna lifted herself slightly and again pinched the latex skirt over my nose, allowing — forcing — me to swallow and then to open my mouth again.
She repeated the process six times. Throughout, I wondered at the irony that even though I had this gorgeous woman sitting with her vagina on my mouth and peeing into me, I still couldn’t see her naked, thanks to the leash holding my head and the latex skirt.
Donna never took her eyes away from mine. It was clear that she was as turned on by the look in my eyes as anything else.
When Donna finally let up, she placed her vagina over my mouth one last time and played another track on the MP3 player. “Now lick me clean!”
I suspected I had her shaved pussy clean in only a few seconds, but not surprisingly, she had me lick until she’d had another orgasm.
She then slid off, removed the headphones, and unattached the hooks at my leash and heels. Of course, with the full bondage ensemble, I was still basically stuck.
I heard the door open, and three pairs of hands helped pull me out of the van. We were in yet another house garage. It took me a second to get my bearings, but I remembered that Jane had been street parking before. Where were we?
“I know what you’re wondering,” Jane said. “I do have a garage, but if I’d pulled in here on the first night, you might have gotten a bit suspicious.”
I looked around, and aside from the washer and drier and the usual utility shelves one would expect in a garage, there was also what appeared to be some sort of modified stockade device, as well as a cage and a few other items. Even before the knowledge I’d gained over the last few days, I’d have realized that something was up if I’d seen those.
“Don’t worry, sweetie. I’m not planning on using anything here. Yet.” All three of them were grinning.
“Now, let’s see what you look like.” Jane walked around me, examining everything Donna and Randi had done. She squeezed the hobble skirt over my cock, oohing when the girls explained the layers of Spanx they’d put over my cock to restrain it. She swatted my ass when they mentioned the dildo, sending a jolt through my body.
She finished looking over me and said, “I love the heels you chose.” She looked me in the eye when she said so, and seemed to be waiting for a response.
“I didn’t exactly choose them, Jane.”
“Don’t be silly! I’ve been watching you for months, remember? You always would steal glances at my feet. I thought it was a foot fetish at first, but you didn’t seem to care if I wore sneakers or mary janes. So I played around a bit. You seemed to get more distracted when I was wearing higher heels. And you nearly walked into a wall on the day I wore platforms! “So tell me again that this is what you wanted!”
She had me. Of course, it wasn’t what I’d wanted at all, but I did find her attractive when she wore these heels.
“I wanted these shoes.”
“Good boy. Now open your mouth.”
I knew that there was no point in resisting. She put a bit in my mouth and wrapped the gag around my head. I thought the gag was small at first, but then she started pumping it, and I realized that it was inflatable. After three or four pumps, my mouth was pretty full.
“This is your punishment. Not just for disagreeing with me, but for forgetting to call me by my proper title.”
Crap! I’d forgotten to call her “my queen.”
I tried to say, “I’m sorry, my queen.” It came out more like, “I auugy y een.”
“I could almost understand that.” She gave one more pump, filling my mouth entirely.
The girls giggled, and Donna grabbed the leash and led me — slowly — inside.
They took me into the bedroom and pushed me onto the bed, attaching my leash to the headboard. Jane had changed the sheets, and I was on top of a leather-topped mattress.
“Did you two take lots of pictures?”
“Oh, we got plenty,” Randi said. “And lots of video, too. His entire transformation has been recorded.”
“Great! And you hopefully had some fun with him, right? The girls laughed, while I could do nothing but lie face down on the bed, immobile.
“Now let’s get changed for the next part, okay?” Instead of hearing them leave, I heard the sound of clothing being removed. Of course, I couldn’t turn around or move to see any of the changes.
If I’d had any doubts that they were doing this to tease me, they were shattered when I saw Donna’s latex cheerleader skirt thrown onto the bed past my head. This was followed by the rest of her clothing, as well as the clothing that Randi and Jane had been wearing.
After a few minutes, I felt a weight on the bed, and Jane crawled onto my back. She reached around my head and placed the familiar pair of goggles over my eyes.
“Much as I love how Randi bound you, we do have to make a few changes. Don’t worry about the shoes, though; they’re staying.” Oh joy.
The girls stood me up and moved my cuffed hands from my thighs to my collar. They then removed the hobble skirt, although the chain on the shoes kept my legs mostly together. They next rolled down the slimming panties. Horny as I was, the constant pressure of the panties and the skirt meant that I was only at about half mast, and before I had a chance to grow again, I felt my cock and balls again sealed in a pouch.
I was leaned over something — a chair back, I’d guess — and felt the dildo slowly removed from my ass. The ladies followed this by sliding a new pair of panties onto me. The final steps involved removing my sweater (unlocking my wrist cuffs first, of course), and then wrapping what felt like a tube top around me.
They had me stand up, and then removed both the goggles and the horrible inflatable gag.
The sight that greeted me was the mirror, and not a whole lot had changed. The top was a tight leather tube top, which hugged the fake breasts well and made them seem real. The panties were black, of course, and were crotchless, allowing my cock-pouch to show through.
But when Jane turned me around, I was blown away. All three ladies were wearing matching leather dresses, which hugged their hips, showed a nice amount of cleavage, and ended inches shy of their knees. They also had black stockings, and amazing black buckled knee-high platform boots, all with sharp heels. Other than lipstick in varying shapes of red, that was it. Simple, and gorgeous.
Jane grinned. “You like what you see?”
How could I not? “Yes, my queen.”
Jane smiled. I’d passed that test, at least.
“Wouldn’t you like to have sex with all three of us at the same time?”
I knew the question was a trap. But even if I’d had a choice, I’m not sure I could have given a different answer. Randi, short, plump, and more experienced at a barely legal age than I was a decade later, had a propensity for cruelty that worried me. Jane, my crush of so long, was utterly devious. And Donna, at least ten years older than me, seemed to view playing with me as a new, liberating experience. But the thought of being with all of them still got me excited.
“Yes, my queen.”
They all smiled. “Of course you do. Get on the bed and kneel!”
It was tough with my heels and my hands bound, but I managed it.
“No, move over a few inches.” I figured that Jane was messing with me, but I did so. It’s tough to shift without putting your hands on the mattress!
When they felt I was in the right place, Randi and Donna got on each side of me and wrapped a pair of straps around my shins, right below my knees. I felt a click, and realized that they’d somehow attached my knees to the bed.
Jane grinned. “One of the great things about leather, sweetie, is that it’s easy to put hooks and eyeholes into it.”
They followed this up by attaching a chain to the back of my panties — where I guess another hook had been added — and to the headboard. Randi then hopped off the bed, grabbed the leash, and threaded it through a hole in the mattress. With a grin, she started pulling on the leash, and thus pulled my head and upper body down. Since my waist was stuck facing straight up, I didn’t have much room to move, and soon found myself in the classic doggie-style position as Randi secured my collar to the mattress at the edge of the bed. Once my head was locked into place, they removed the chain from my waist, but in the position I was in, I couldn’t move.
Things got even stranger next. Jane pulled a small leather ottoman about a foot in front of me, took my left hand, and secured the cuff to a stud on the ottoman. She repeated this with my right hand, but added an extra twist. She took a condom and slipped it over both my index and middle fingers. She then slipped three more over them, wrapping a rubber band at the base to keep them tight. A little flesh-colored adhesive tape held my other fingers shut.
The ladies stepped back to admire their handiwork while Jane took a few more pictures.
“You know what the best thing about this is, sweetie? Every single one of those clips and buckles is hidden out of sight. Of course, we still have one thing to hide.”
With that, Donna kneeled on the ottoman, the skirt falling over my hands. She reached under and guided my double finger into her. She was wet enough that I glided right in, as she gasped.
Randi stepped between my arms. I wasn’t surprised in the least that when she lifted her skirt, she was wearing what appeared to be the same panty/strap-on combo she’d used earlier. “I bet you missed this,” she said as she slid into my mouth. I didn’t in the least, but couldn’t so anything about it.
Finally, I heard Jane get up behind me. I wasn’t surprised to discover that my panties had a hole in the ass for easy access. I felt the lubed tip of whatever strap-on Jane was wearing brush against my hole.
“Oh, honey, I forgot to tell you what Donna wrote on your ass. It says, “fuck me here, and has arrows pointing right to your asshole. Isn’t that cute?” With that, she slid into me, using a phallus that was certainly bigger than the one they’d taken out not that long ago.
For the next hour, I was their fucktoy, as they pumped my mouth and ass, and rode my fingers. They would occasionally switch positions, with all of them getting a turn at each “station,” Fortunately, Jane switched to a different dildo when she pumped my mouth (“because you’ve been so good,” she told me), but it was still humiliating and extended. I’d swear that the dildos got bigger with each woman.
The two older ladies eventually tired out (well after I did), but Randi, who’d been taking a turn reaming my ass, wanted to try one more thing, and Jane agreed to help.
Randi stood out of her panties, leaving the dildo stuck in my ass. She then wanted around to her initial position in front of me, turned around, and knelt over the ottoman. This placed her gorgeous leather-covered ass just inches from my face.
Jane sat next to me, her leather-clad body brushing against mine.
“Randi wanted to give you a special treat, so since you’ve been so good, we figure you’ve earned the right to see her ass.” Randi lifted her skirt, and there was, indeed, a nearly-perfect ass!
“Tell her what you think of it,” Jane whispered in my ear.
“It’s an amazing ass.” I wasn’t lying.
Randi giggled. It was exactly the sort of giggle I might have expected from a girl her age flirting at a party, but in her case, I knew she had something planned.
Sure enough, she slid the ottoman backwards, pushing her ass towards my face. At the same time, Jane held my head straight and guided my lips right to Randi’s asshole. “You know what to do,” Jane said. Given no choice, I went to work.
I soon felt hands at my collar, and realized that Jane had clipped my collar to Randi’s thighs and removed the clips from the bed. I was trapped licking her asshole until they freed me, with my nose pressed against the top of cheeks my only source of air.
Periodically, Jane or Donna would push against my head, making sure that my tongue was deep inside of Randi. After three loud orgasms, Randi finally decided she’d had enough, and I was released.
Jane undid most of my restraints, leaving only my head in place. The others got their clothes, and also picked up a bunch of mini-video cams. “We should have lots of fun editing these, ” Randi said. Jane hugged each of them goodbye, and each leaned down to give me a kiss on the cheek.
“I’d kiss you on the lips, but I know where your mouth has been,” Randi giggled.
“Thanks, sweetie,” Donna said. “Come into the salon anytime you need a touch-up.”
Once Jane walked them out, she came back in and sat on the bed.
“Now, let’s get you cleaned up.”
Chapter 11 — Take a breath.
The routine this time wasn’t too different from the last few times. I was once again led into the bathroom, chained and showered. Jane spared me the analingus this time, though, and when I was clean (and still naked), she led me back into the bedroom, where she tied me down again.
“I need to run a few more errands, and I’m pretty sure you’re worn out. Why don’t you take a nap? This should give you some sweet dreams.” With that, she slid a pair of panties over my head, with the crotch landing right over my nose. As she walked out, I tried to think about where my situation was headed, but Jane had been right; I was just exhausted, and even with her intoxicating smell in my nostrils, I fell asleep in minutes.
I woke up to the sound of the door slamming later. I had no idea how long had passed, but I certainly felt refreshed. I heard Jane’s heels click across the floor as she approached the room.
“I hope you had a good nap. I bought some really nifty stuff.” With the panties over my head, I couldn’t quite see her even as she sat down on the bed. She leaned forward and wiggled her fingers in front of my face. She’s clearly had a salon treatment, and now had very sexy black fingernails.
“You like? Of course you do, silly! I do pay attention to how you react to me at the office, after all. Whenever I wear black polish, you can barely take you eyes off of me. More than usual, that is.” She giggled and ran the tip of her index finger across my bottom lip.
She sat down on the bed, and I heard the sound of her heels dropping. “I also got a pedicure, of course.” She stretched one shapely calf out over me and wiggled her now-black toenails in front of my face.
“Don’t think I didn’t notice how much you liked looking at my toes, either. Every time I’d wear open-toe shoes, you’d keep staring at my toes. And you’ve got some sort of attraction to weird polish colors, too. When I wore the blue polish last week, you practically walked into a wall staring at me!” It was true. And her current black pedicure was just as enticing.
“Why don’t you show me how much you like it?” Jane moved her foot down to my mouth, rubbing her big toe against my lip. “Kiss my toe.”
I did so, giving it a light kiss.
“Now kiss the rest of my toes!” She slid her foot along my lips until I’d kissed each digit. She the slid the big toe back to the center.
“Now, suck my toe!” She bent her foot slightly and slid the toe over my lip and into my mouth. I licked it tentatively.
“No, suck it like it’s a tiny little cock!”
I did as Jane demanded, sucking and licking the toe for a few minutes. After a bit, I felt her shift the rest of her foot against my mouth, and she shoved the second and third toes into my mouth as well. I sucked and licked, but before I knew it, she’d shoved her entire front of her foot in my mouth, and was bracing her other foot against the back of my head. Jane’s feet were not large, thankfully, but the entire foot was every bit as wide as some of the dildos she’d had me suck. Her toes had a slightly musty taste to them, but for the most part tasted clean.
“I told you I had plans for other gags. Using my foot’s one of my favorite ones. It keeps you quiet and it keeps me entertained.” Her breath was becoming ragged at this point, and I suspected she was actually going to come from my attentions. I couldn’t tell if she was also masturbating while I sucked, or if it was just the toe action itself that excited her, but either way, she soon came.
She then got up and walked away for a bit. With her heels off and my eyes still somewhat obscured by the panties, I wasn’t sure where she’d gone, but in a few minutes, she came back to the bed and slid the panties off my head. She also placed a curved pillow below my head. I did finally get a glimpse of what she was wearing, but was surprised to see that it was a rather conservative full-body dress.
“Disappointed, sweetie?” Jane had obviously caught my reaction.
“Of course not, My Queen.” I figured that even if she saw through the lie, remembering her “title” would help.
She smiled. “Mmm. ‘Queen,’ indeed.” She reached down and grabbed something, and fiddled with the pillow. I couldn’t quite tell what she did, but I felt a soft cushion against my neck, and my collar was locked into place.
“Do you know what ‘queening is, hon?”
“No, My Queen.”
“Well, I’ll explain it to you in a bit. But first, let me go change into something more appropriate.”
She walked away, and a few minutes later, I heard heels clicking on the floor as she approached. She stopped just out of range, and with my head effectively locked into place, I couldn’t see her.
“You saw me in lots of leather yesterday, but I decided to go a little more extreme today.” Jane lifted her foot and showed me the sexy black leather high-heeled ankle boot she was wearing. “I’d know you liked this even without watching you at work. There’s not a guy on the planet who wouldn’t be turned on by these.”
I could also see the bottom of what looked like leather pants, but it wasn’t until Jane climbed on the bed and straddled my chest with her knees that I got to see what she was really wearing. It was a full leather bodysuit! It hugged every one of her curves, swelling at the breasts and showing off her hips perfectly.
Jane grinned through her bright red lipstick. “You like it, I’m guessing?”
“Yes, my queen.” I said. She’d already glanced behind her and seen how hard I was.
Jane stood up and walked around to the head of the bed, leaning over me. “You know, you always told me how much you’d enjoyed that summer in England. Do you remember when we talked about all those words that mean different things? like ‘Bobby’ and ‘boot’ and ‘lift?’”
As I nodded, she got up on her knees on either side of my head. With the strange pillow device restraining me, her knees weren’t touching me, but I still had a great view of how tightly the catsuit hugged her ass and crotch.
Jane looked straight down into my eyes. “Care to take a guess what ‘queening’ means over there?”
As I opened my mouth to answer, Jane quickly lowered her crotch right onto it, silencing me.
“It means ‘face-sitting,’” I heard her say, as she filled my mouth with her leather-covered crotch. “And I think you’ll find that leather is a little less forgiving than the lacy cotton Randi wore!”
With that, she shifted so that her ass settled right on my nose, and for the second time that day, I found myself unable to breathe. My senses were dominated my leather. I could feel it, taste it and smell it, and all I could see was Jane’s leather-clad back.
I felt myself starting to go a bit dizzy, either from the lack of air or the smell of the leather, but before I could lose consciousness, Jane shifted forward enough to allow me to breathe through my nose.
“Wow, Randi was right,” I heard Jane say. “You really are into this.” She leaned forward and gave my cock a squeeze. I’d remained rock-hard throughout. I tried to protest that I was not a fan of “queening,” but with Jane’s crotch still on my mouth, no words could come out.
“Oh, that felt nice, even through the leather! But I think we could have even more fun!” With that, she spun herself around again so she was once again seated on my chest. It felt good to finally work my jaw muscles a bit.
“That contraption over your head is a custom-made smotherbox. I think you can guess the point of it!” Jane ran her black-painted fingernail along my lip as she talked. “It allows me to keep your head still so that I can cover you whenever I want. But let’s add something to it, shall we?”
With that, she slipped a leather blindfold over my eyes. I felt her shift around, and even though I couldn’t see it, I knew that I’d be smothered again soon. Sure enough, I felt her settle down and cover my mouth and nose again.
Jane repeated the process a few times, spacing things out at different intervals, so I was never truly sure when she’d cover me again. The fourth time, she pulled a particularly mean trick, and just as she pulled away and I was about to inhale, she sat right back down, and I found myself inhaling nothing but leather. I was afraid that I’d actually lose consciousness that time, but she pulled off in the nick of time. Even with the blindfold on, I didn’t doubt she was grinning.
Even as I got used to grabbing a breath whenever I could, Jane added another item into the mix. As she settled on my face again, I felt her playing with my nipples, pinching and flicking them. And all of a sudden, I felt a burst of pain. She’d put nipple clamps on me again! These were definitely tighter than the ones she’d used earlier, and the pain made me shout into the leather mound over my mouth.
From Jane’s squirming, that was exactly what she’d wanted, and she spent the next few minutes both smothering me and flicking my nipples and adjusting the clamps, indirectly using my mouth to give her pleasure. There were moments when I was afraid that she’d forget how long she’d been sitting on me, but it was only when she finally orgasmed that things really got tense. As she shuddered, she pressed her ass firmly into my nose, nearly breaking my nose.
Jane finally slid off and turned around. After removing the clamps (which, after a fresh burst of pain as the blood rushed back in, was a relief), she asked me, “how are you doing, sweetie?” I couldn’t see her eyes, but she did sound concerned.
“Honestly, near the end there, I was afraid you were going to break my nose.”
“Oh, I’m sorry, hon! I hadn’t even though about that, but sexy as the leather is, it doesn’t really offer a lot of give. Hold on — I think I’ve got a way to fix that.”
With that, she slipped off the bed, and I heard her heels click away. When she returned a few minutes later, I didn’t realize it until she’d climbed on the bed. She’d obviously removed her shoes. I felt her kneeling above me again,
“Open up,” she said. I knew better than to resist, but was shocked when I felt the contact of flesh against my lips. It took me a second to even process that she’d lowered her very naked and wet pussy over my mouth. And by the time I realized the implications of that, she leaned back, embedded my nose in her crack. It wasn’t thankfully, buried in her asshole, but closer to the top of her crack. The skin did have a little more give than the leather, although breathing was still a challenge.
After yet another orgasm, she shifted around, sitting next to me on the bed.
“You know,” she said, “the pants weren’t the only thing I took off.” I felt her lean down and rub against my cheek. It took me a second to realize what I was feeling, but it was her nipple!
She rubbed it against my lip, and I strained to take it into my mouth. Alas, I was secured down tightly, and couldn’t.
“Oh, poor boy. So hungry for it!” Even with the blindfold, I knew she was grinning as she said it.
She slowly teased me, rubbing her nipples around my mouth and against my cheeks, never letter me taste them. After a few minutes, she relented and lowered one breast to my mouth. I sucked in her nipple and heard her gasp in pleasure. After a few minutes of my attention, she switched to the other breast. Then, just as I’d gotten completely caught up in the joy of the moment, Jane shifted forward, covering my nose with her breast!
Even as I struggled for breath, I knew that biting down on her nipple would make things worse, not better.
After a few seconds of my pointlessly struggling, Jane lifted herself up. “I’m sorry, sweetie! I guess I just got caught up in the fun!” I heard the teasing in her voice, of course. Not that I’d ever doubted she’d done that on purpose.
She leaned down and gave me a quick peck on the lips.
“But that’s enough of that. Let me just get changed, and then you’ll have to make a choice.
With that, she walked away, leaving me blindfolded and confused.
Chapter 12: Decision
I heard Jane walk back in a few minutes later, and braced for whatever new torture she had planned. Much to my surprise, she untied me, removed the smotherbox, and even took off my collar. She slipped the blindfold off and sat next to me as I sat up.
She was wearing a pink sweatshirt and jeans, and had switched to a pink lipstick. I wouldn’t go so far to say that she looked wholesome — not after the last few days, and she still was wearing tall heels — but the look was certainly closer to what I’d grown used to from her at work.
“You don’t have to use my title for the next few minutes. I need to ask you something.”
I wasn’t sure how to react. Was this some sort of trap?
“Okay,” I said.
She smiled at my cautious tone. “Remember how I said that if you were good, you might get an orgasm? And get to see me naked? This is where you get to make that decision. I like you. And I’ve known that you’ve had a crush on me for a while. But I’ve got special needs, as I think you’ve figured out.”
She lightly brushed her fingers against my cock, which had been at half-mast, but instantly sprang to full attention.
“And I think it’s clear that, no matter what you might think, at least a part of you is enjoying this. So I want to make you an offer. You’ve got two choices: First, you can leave here tonight. I won’t stop you. If you do that, I’ll pretend this weekend never happened. I’ll smile professionally at work, but you’ll never have another chance to be anything more than a co-worker. And if you’re thinking of telling anyone what happened, I doubt they’ll believe you, but I’m pretty sure you wouldn’t do that.” She smiled again, and I realized it was true.
“The second choice is that you agree to be my slave.”
“What does that entail?”
“First, you move in with me. To the outside world, we’ll be just like any other couple. And we will be a couple; I can’t keep up this level of activity every day!” She grinned. “I like you because of our conversations at work about movies and books, so you’ll still have free time to read and see friends. And I wouldn’t dream of doing anything to interfere with your job.”
“As for what I will do to you, I don’t want to spoil all the surprises, but I think you’ve figured out that I like bondage a lot, and dressing you up, and a lot of other nasty stuff. I’ll do everything I’ve already done to you, and some stuff you haven’t even thought about. But I can make a few promises: First, you’ll have at least one orgasm a week. Second, the only people I’ll ever share you with are Randi and Donna. Third, nothing that’ll damage you. I’m not saying you’ll never get spanked, because you know that’d be a lie. But I get off on control, not pain. Make sense?”
“And finally, you’ll never be bored.”
She grinned, and I smiled back. Whatever else I could say about the last few days, I was certainly never bored.
“So, how long do I have to think about it?”
“Oh, I know it’s a big decision. How about ten seconds?” She grinned.
I wanted to protest. I still wasn’t sure how I felt about being Jane’s pet. On the one hand, she’d had me do some stuff that appalled me. On the other, she was still one of the most attractive women I’d ever known, and I couldn’t deny that even as I thought about the last few days, my cock was still hard.
“Okay, I’m yours.”
Jane smiled and hugged me. “Oh, I’d knew you’d agree!”
Her thighs brushed against my hard cock, and I slid my arms down Jane’s back, planning to finally reveal her wonderful breasts, but she pulled back
“Hold on there! What did you think you were doing?”
I was confused. “I’m sorry, Jane. I thought that you’d said that if I agreed, well, you know. . . “
“Oh, that’s you’d get to see my tits and fuck me?
Jane smiled. “Oh, I love that you’re still that innocent. I wasn’t lying, of course, but those will happen on my terms. Kneel in the middle of the bed!”
I did so.
Jane stood up in front of me. With her heels, my face was level with her breasts, but I barely had time to notice how tightly the sweatshirt hugged her before she commanded me to look up into her eyes.
“Now, pet,” she said, taking something leather out of a bag, “this is my ownership collar. If you earn the right to wear this, you’ll wear it whenever you’re not at work, and it’ll let anyone know you’re mine. If you want it, beg me for it!”
“Please, My Queen,” I said, looking earnestly into her eyes, “may I wear your collar? I’m begging you to let me be yours, and for you to use me.”
“That’s a start. Do you understand that if I take you, I’m going to use you only for my pleasure, however I see fit?”
“Yes, My Queen.”
“And that if you wear my collar, you give up your right to question me, to fight me, to do anything I don’t feel like?”
“Yes, My Queen.” I was excited, but also scared.
She smiled, leaned down, and softly kissed me on the lips. Even as I got lost in the kiss, I felt her wrap the leather around my neck. It didn’t feel much different from the old one. She also attached a leash to it.
“This is the same type of collar as the other one.” As she said this, Jane kneeled on the bed and slid around behind me, whispering the words in my ear. “But it’s got the words ‘Jane’s Pet’ on it. If you’re good, I might let you see it.”
As she talked, she attached my wrist cuffs to each other, then had me shift so that I was sitting instead of kneeling, with my feel facing the end of the bed. It was tricky, but I managed it. Jane promptly attached my ankle cuffs to the bed, then stood on the floor in front of me.
Before I realized what was happening, she had kicked off her shoes and started wriggling out of my clothes. Alas, she wasn’t naked, but was down to a black bra and a pair of peach panties that tied on the side.
She kneeled on the bed and slid a bit forward, sitting right in front of my hard cock.
“Your begging earned you the collar, but you’ve got to work a little more to see my tits and especially my amazing pussy.”
“Just tell me whatever I need to to, My Queen.”
Jane smiled. I’d clearly said the right thing.
“Well,” she said, pretending to think. “I do think I can give you a consolation prize.”
She turned around and leaned forward until she was on her knees, her gorgeous ass sticking up in the air.
“You’ve never been very into politics at work, but you could make me very happy with some ass-kissing right now!”
As she said it, Jane tugged lightly on my leash, and I took the hint and leaned forward. It was tough, with my hands and feet immobilized, but I was able to kiss her left ass cheek, and then her right.
“Sweetie, only friends kiss each other on the cheek. Kiss me in the middle.” I did so, smooching the center of her panties.
“Okay, you’ve earned your first prize.” With that, she untied one side of her panties, letting them fall to the side and revealing her asshole. I was barely two inches away from her ass, and not far enough back to see her pussy, alas.
“See! You’re finally starting to see me naked! Now, give it a real kiss, honey. With tongue.”
I leaned in and repeated the actions she’d taught me in the shower. As I stuck my tongue in, Jane pulled the leash forward, and my tongue was driven all the way in. I was able to roll my eyes upward enough to see that Jane had tied the leash around her waist, effectively sealing me to her.
As I licked, Jane pushed against me, slowly bringing me back to an upright position, then pushing me down so I was flat on the bed, my tongue still stuck in her asshole. She sat firmly on my face, and even though my bound hands under my back made me uncomfortable, I knew that I had to focus on satisfying her. I thrust and licked with my tongue for what felt like hours, but were likely only a few minutes, and then felt her shudder. She untied the leash and slid off my mouth, but slid her panties on before I could glimpse her pussy.
“You’ve earned two more rewards,” she said. She then took off her bra, and I lost track of that what she was saying.
“Like what you see, sweetie?” She grinned. Her breasts were as perfect as I’d expected, and my erection was now painfully hard.
“Now, you get to make a choice again. Do you want one orgasm tonight, or two?”
I blinked. Had I misheard the question?
“Two, please, My Queen.”
“I thought so. Let’s work on one of them right now.” She reached under her skirt and untied her panties again, letting them drop to the ground. With a grin, she straddled my crotch and guided my cock into her pussy. She was wet and clearly excited.
“Needless to say, lover, you get to come when I say you do,” Jane said, as she started to ride me. My hands beneath my back made me uncomfortable, but not enough to slow me down, alas. I could feel my orgasm coming, and watching Jane’s beautiful breasts bouncing only hastened things.
“My Queen,” I panted, “I’m not able to hold it in much longer.”
“It’s okay, my pet,” Jane said, even as she continued to ride me, “I give you permission.”
The words had barely left her mouth when I came, shooting inside her again and again. I’d been teased and aroused more times that day than I could count, and I must have spurted more than ten times.
Jane collapsed and nuzzled my neck. “It’s okay, lover. I knew you wouldn’t last long that time. But you pleased me, and you earned your next prize.”
She slid off me, and quickly removed her skirt. Beneath it was her gorgeous pussy, with the hair neatly trimmed and demonstrating that she was, indeed, a natural blonde.
“See, you got your prize, and are finally allowed to see me naked. Was it worth the wait?”
“Yes, My Queen.”
“Now, let’s have you earn your next one.” Jane slid up the bed towards my head. “Open wide.”
As she dropped her pussy onto my mouth, I tasted my come as it dripped out of her. She rode my face long after I’d eaten all of my come, having me tongue her to two more orgasms.
She finally lifted herself from my head. “Yeah, I’d say you earned that second orgasm tonight, sweetie. I can’t even count how many times I’ve come today!”
With that, she slid down and took my cock in her mouth. I’d thought I’d be too sensitive after the previous orgasm, but my body responded to her tongue, and soon I was hard again. It took longer this time for me to come, but I still doubt I lasted more than a few minutes. Much to my (pleasant) surprise, Jane actually swallowed all my come this time.
As I lay there gasping, I felt her doing something around my cock, but before I really had a chance to wonder what was going on, I heard a click and felt something tighten around my now-flaccid member,
“Just a basic chastity belt, sweetie. I told you you’d get at least one orgasm a week, but this makes sure I get to determine when!”
“Now, let’s get your ready for bed!” She took me to the bathroom and allowed me to quickly use the facilities and shower before guiding me back to the bedroom. The belt meant that I’d had to pee sitting down, but wasn’t too uncomfortable. So far.
Jane stood me in front of the bed and stood behind me. She had me hold onto the footboard of the bed and lift my legs one at a time, and I felt her slide heels over my feet. These were much more severe than anything she’d used before — my feet were practically vertical! There was also clearly a platform, as I was now much higher than before.
I felt Jane sliding something up and over my head, and soon found myself looking through a pair of eyeholes. Even before I could question her, she forced something leather into my mouth and locked it into place. She turned me around, and looking in the mirror, I saw that I’d had a tight-fitting leather hood placed over my head. Only my eyes remained uncovered. My feet were stuck in black patent leather ankle boots with a ridiculous platform that had to be at least four inches, and another four inches of heel. I saw little locks ensuring I couldn’t get out of them, not that I suspected I’d get the chance.
Jane spun me back around, and with the heels, I nearly stumbled. I felt her attaching my boots to the bed, and with a gentle push, I tumbled onto the bed. The heels and the restraints kept my legs on the ground, and made my ass jut up into the air.
I felt Jane hop on the bed, and wasn’t surprised at all to feel her lube my ass. That was followed, of course, by a dildo, easily as big as the ones the girls had used on me earlier today. Once that was in, she stood me up, turned me around, and rechained my ankles.
“Enjoying this, sweetie? I figured you might actually want to watch me restrain you this time.” Jane hadn’t bothered getting dressed after the shower, and I could gladly have just watched her.
She grabbed a large leather item whose purpose I couldn’t quite figure out and wrapped part of it around my neck. It had a collar that covered my other one, and which attached to a piece of leather that ran down the center of my chest and spread out to cover my abdomen. Once she’d finished wrapping it around me, it covered my stomach and throat, but left large openings around my nipples. I’d guess that it was designed for a woman, given the size of the openings, which clearly were meant to expose the entire breast.
Even though I could see what was happening, I hadn’t figured out exactly what was going on until Jane had me slide my right arm into a leather sheath. As she got behind me on the bed and pulled the sheath around to my back, I realized that she’d placed me in a straitjacket! Although this certainly wasn’t like anything I’d seen in the movies. She repeated the process with my left arm, locking both arms into place.