Chapter One
“You can’t be fucking serious.”
I looked at Jessica. My stomach was already tight because I was so nervous but I pressed on anyway because there was no reason to waste time on a relationship that had no future.
“I told you I was serious. Now it’s your turn.” I waited expectantly.
She looked down at the object I had placed on the table. Maybe it wasn’t a conscious choice, but she had hidden her hands under the table so she wouldn’t be tempted to touch it.
I knew I was dumping a lot on her, but what was she expecting? We were six weeks into a fairly intense relationship and if she wasn’t going to participate in my kink then I wasn’t going to waste any more of my time on her.
The cock cage on the table between us was expensive. For the amount of money I had spent on it, it wouldn’t be a stretch to consider it a work of art. I had often wondered how much time Michelangelo had spent on sculpting David’s small, soft cock in his famous statue. It was probably less time than had been spent on the surgical steel containment device.
“I don’t think I can touch that,” she said finally.
Disappointed, I looked at her face. Her eyes were wide open and projecting shock. My eyes were drawn to the little birthmark on her right cheek. It was an imperfection that was both sexy and intriguing to me.
With a sigh, I stood up. We were in her apartment. I had given her the I think we need to talk about our relationship line to get the conversation started.
She had been nervous. I don’t think that telling her about my kink had helped. Nor had demanding that I know what her kinks were.
“Then I don’t think we’re going to be able to continue on,” I said. “I knew I was into this since I was like...I don’t know...sixteen? Eighteen? I want you to be completely in charge of my cock and if you aren’t willing to do that...let’s just part as friends, okay?”
I picked up the cage from the table and started to make my way out of the place.
“Anal!” she suddenly blurted out.
I stopped in my tracks.
“Excuse me?”
“Anal,” she said. “I love anal sex.”
“We haven’t had anal sex.”
“I know...I’ve been trying to stop...and maybe if you are wearing that cage...maybe I can stop.”
Though I had stopped walking away, I now froze completely. I just wanted Jessica to be my keyholder. Now she was talking about keeping me inside the cage just because she didn’t want to have anal sex?
“We’ve never had anal,” I repeated, mostly for myself because I was confused.
“I know. And I want to keep it that way.”
“Most women don’t have anal sex,” I said, though that seemed self-evident.
She grimaced in a way that was somewhere between embarrassment and pain. “Yeah. I do. I did. I don’t want to do it any longer.”
“Well...that seems like a simple request.” I’d done anal with other girlfriends. It was a nice change of pace from the usual vaginal and oral, but it had to be the right circumstances to make it worth the effort.
“Have you worn that thing before?” she asked me.
I looked down at the cage in my hand. “Yeah. I have. With a couple of girlfriends.” I didn’t go into detail. She didn’t want to hear more than that I was sure.
“If you wear it, we won’t have anal sex, right?”
“If I’m wearing it and you’re my keyholder, I won’t be having sex at all. You can still have sex.”
She looked blankly at me. “What? You think I’ll be fucking other men?”
My heart skipped a beat and I found myself thinking If only! But that was a step too far right now. “No. No...of course not,” I lied. I sort of lied. Wanting her to do it wasn’t the same as demanding that she do it. “I mean we can have oral and manual sex. That’s sex.”
“Manual?”
I had already partially fried her brain so it wasn’t a question out of nowhere. In response, I held up my hand. “Fingers. I can make you cum from manual manipulation of...of whatever you want.”
“Oh.”
The curiosity was killing me. Maybe I’m part cat. “Why don’t you want to have anal? And I’m going to point out that I wanted to know what kink you like to do. Not one you don’t like to do.”
“I love anal,” she said with more enthusiasm than I ever would have guessed.
“Ookaayy…” I carefully approached the table and sat down. In the back of my head I was hearing my college roommate’s advice, Never stick your dick in crazy! Never stick your dick in crazy! This happened after he had been dating Juliana, a particularly hot girl who wound up spray painting his car bright pink because he talked to another girl in his chemistry lab. But it was the best sex of my life!
I often wondered what happened to Mark after college.
“If you love anal, why don’t you want to do it?” Jess hadn’t struck me as particularly religious or uptight about sex or anything, but maybe this was the first red flag that I was seeing.
“I love anal,” she repeated, her eyes getting a dreamy look. “When I have anal, I have the best orgasms. The best. Ever. Nothing else compares.”
I felt a little emasculated. Sex with Jess had been fun and wild and I thought rather great. But she was saying the best orgasms she had were from anal.
I hadn’t even put a finger up her ass.
“So sex with me has been...adequate and now you want to avoid having better sex,” I said carefully.
“No...I just want to stop having anal,” she tried to explain, but she was lacking in her actual explanation.
“Why?” I especially wanted to know why because, as much as I liked Jessica, I didn’t want to be the only man she had sex with who didn’t get to have anal with her.
Of course, if I was wearing my chastity cage, she wouldn’t be having sex at all.
Except manual or oral.
With me.
If she wanted vaginal—or anal—she’d have to go elsewhere for it.
I was hoping she wanted to go elsewhere...and let me watch.
But first steps.
“Why what?” she replied.
“Why don’t you want to have anal sex if it’s what you really like?” I asked her.
“I could ask you the same thing.”
“I’ve never been fucked in the ass,” I said quickly, though I realized right away that was the wrong thing to say since she apparently loved it. “Not that there’s anything wrong with liking anal. I’ve only ever done it a few times.” I kept the details vague. Two women, Josie and Mandy. Josie wanted to try it because her gay best friend said she had to. Getting out of that relationship was easy. Mandy and I did it three times; each time she was completely drunk.
“Well...it’s a lot of fucking work and...and it’s disruptive.”
“How so?”
She sighed. “I’m not meant to have a cock up my ass. No one is.”
“Yeah, but you like it. You said you like it.”
“I like it at the moment...but then the next day it’s not so great. There are a lot of complications afterwards.”
“Oh. You mean santorum and pain.”
“Not pain. Mostly soreness. But it’s messy too.”
“Right.Well. I don’t see much of a problem here. Do you?”
Jessica held her face between her hands, elbows on the table, wondering what the fuck she had gotten herself into. “I guess not.”
“Great. So you’ll agree to be my keyholder and I agree not to fuck you in the ass?”
“Sure. Why the fuck not?”
We celebrated by doing exactly what we shouldn’t have been doing.
We each had a shot of tequila to start things off. That was a bad decision.
I showed her how the chastity cage worked.
“Why is it called a chastity belt?” she asked. “It’s not really a belt. It’s more like a hollow steel banana.”
“It’s not called a chastity belt. Those are made-up things from the Victorian Era. No one every actually wore one.”
“Oh. Okay.” She took another shot of tequila. That was probably a good idea now that I couldn’t think straight. “So why do you like wearing this?”
I had disassembled the cage. It was sitting on the bed between us. It’s really just a few pieces. The main part was a curved solid metal shaft with the end for my head an elaborate pattern of bars left open end so I could pee. The base ring that goes behind my balls to hold the whole thing in place. The lock and key on top to keep me locked up. There are a couple of spacers that are permanently affixed to it because it was sized exactly for me. That’s it.
“I don’t know. I just like the emotional feeling of having someone else in charge of my cock. Probably because I had a fucked-up childhood.” I didn’t want to get into that now. Let’s just say my parents divorced when I was young. They both had multiple marriages after they divorced each other. Multiple affairs that I knew about which meant there had to be multiple affairs that I didn’t know about. I had witnessed, accidentally, more sex in real life than any teenager should see before, after or during the apogee of internet porn.
“Do you want to tell me details—?”
“Nope,” I cut her off quickly and took my second shot of tequila to wash away the memories. “But once I started wearing cock cages, I started liking the feeling of them on my junk.”
“Okay,” she agreed. “I think I’m drunk enough now to put it on you.”
“Great!” We were both a little drunker than we realized. There was a lot of fumbling around as I showed her what to do. I took off my pants and underwear but left on my shirt. The trick was to get the base ring in place without pinching any skin and then slide the shaft on without getting too bent.
“Now I know why you shave your balls and trim your pubes,” she commented. Apparently I was the first guy she had ever been with who shaved his balls. What type of sheltered love life had she been living?
“You shave your pussy,” I pointed out.
“I leave a landing strip. And it’s so I don’t have curlies hanging out when I wear a swimsuit. Or a thong.”
“I’m going to point out I find your landing strip sexy.”
“Thank you.” She had been manipulating the lock and key and once she figured it out she let out a little cry of triumph and displayed the key to me. I smiled at her. My cock, despite years of training in private, tried to get hard, but naturally I couldn’t since it was surrounded by unyielding metal.
Grabbing my armored junk she shook it back and forth a little. “I’m in charge of your little dick now,” she crowed.
“It’s not little, I complained to her. “I’m perfectly average. Five inches long is perfectly average.”
She sniffed a little. “Don’t I know it. You, Michael my dear boyfriend, are perfectly average. Five inch dick. Five foot nine. Brown hair. Average looks.”
“Average looks?” I protested, but she went on.
“Medium build. Average weight. I bet you even have an average shoe size.”
“I wouldn’t know.”
“I can look it up.”
“I’d rather try out the second half of our agreement.”
“What second half?”
“I go into chastity. You hold my key. I don’t fuck you in the ass, but I do oral and manual on you.”
She brightened and took another shot, this time directly from the bottle. “That’s right. Let’s see if your average tongue lives up to your average cock.” She started struggling out of her jeans, flopping around on the bed. “Can you make me cum just with your mouth?”
“And fingers,” I added.
“Right. And fingers.” She managed to get her jeans off without too much trouble. Her panties were askew on her hips. They were bright blue with a thick white elastic waistband, high cut, but not a thong. Jess flopped back on her pillow and spread open her legs which actually prevented me from pulling off her panties. The top edge of her pubic hair was just barely visible from how they were partially pulled down.
Pushing her knees together with my hands I moved up her body and kissed her. “You can’t fuck me if my knees are together,” she told me.
“I can’t fuck you if I’m wearing a chastity cage,” I reminded her.
“Oh. Right.” She giggled. She was drunk. So was I. A little. At least I didn’t have to worry about whiskey dick. Pulling down her panties for her, I exposed her pussy and this time when she opened up her thighs she displayed her pretty little pussy to me. Her labia were already dark pink. I could see a bit of wetness on her protruding lips. I wanted to dive in right away and start feasting, but she sat up and started struggling with her shirt and bra. It was more like a camisole than a bra because Jess had small tits.
I liked small tits on women.
Actually, I liked any tits on women. I’m not that picky.
But I preferred smaller ones. Call me crazy.
And call me a little drunk, because I was.
Once she was sufficiently undressed, from the waist down at least, I pushed her down on the bed while she continued to skirmish with her camisole. When I put my face between her thighs, she got distracted and eventually stopped trying to remove her remaining clothing while I slathered all my attention on her pussy.
I was already familiar with her intimate anatomy and what she liked. Since Jess was already wet, I just ran my tongue along her open lips to get her taste and then I focused on the little pink pearl sitting atop her slit. A little tongue work and then some firm licking followed by sucking it into my mouth had her crying out for more.
Jessica was a vocal woman in bed. She had trouble shutting up. Either she was moaning with pleasure or running her mouth telling me what to do or how to do it or she was just talking dirty in general. So she was either “Oooh...ummm,” or she was commanding me, “Fuck me harder. Faster! More intense!” or it was a string of filth, “Stick your tongue up my cunt. Suck on my clit. Ohh...fuck I love it when you do that!”
At least she liked sex.
I once pursued a girl in college, Janice, who was beautiful and charming and everything a person could possibly want in a partner. Except when we got into bed, she played the role of starfish and just laid there.
Still, for all my mouth work on her pussy, it wasn't enough for Jess, not tonight. That wasn’t a problem for me, however. I had other options.
While I continued to lick and suck her sensitive little button, I inserted a pair of fingers in her pussy. I didn’t realize it at the time but my pinky was resting near her back entrance. No big deal. I was a little drunk; she was a little drunk. When you get down to it, you’re close to all those parts of the anatomy. I wasn’t purposefully trying to cause problems.
Reaching up inside her, I find the little bump that really gets her going. I hadn’t made her squirt yet by stroking her g-spot, but that only encouraged me to try harder. Knowing now how much she liked anal sex, maybe I was wasting my time with that particular tactic.
Still, I wasn’t going to give up in the middle of sex right then. Not unless she told me to stop. She didn’t. I kept going, sucking and licking and stroking.
Her thighs closed on my head, trapping my hand, as she came. Her entire body tensed up and quivered as she first groaned and then shouted out, “Fuck yes! Fuck!”
While I didn’t think she was going to crush my skull with her thighs, the way my arm was trapped was painful. Luckily her orgasm passed after half a minute and I left her panting and wet.
“You can take your finger out of my ass now,” she told me.
“What?” Unconsciously I jerked back my hand that had been between her legs just as I realized that my pinky wasn’t exactly up her ass, but it was resting against her anus. Had been resting against her anus.
I wasn’t sure if she had liked it or not.
“Thank you,” she said.
I wasn’t sure if she was thanking me for pulling my finger out or making her cum or both.
It didn’t matter.
“You’re welcome. It was my pleasure.”
She reached down and grabbed my metal-covered cock. “I don’t think it was completely your pleasure,” she told me. “You didn’t get to cum.” I liked how she asserted her authority over my cock. It was exactly what I wanted.
“That’s the whole idea. I don’t get to cum except when you decide.”
“What if I decide I want you to fuck me right now?”
I shrugged. “Sure. If that’s what you want. But you need to lock me back up when we’re done. I can’t guarantee I’ll be able to get it up, though.”
“Why’s that?”
“Whiskey dick.”
She laughed at me. “More like tequila dick.”
“Whatever.”
“Do you want to fuck me?” she asked. Her fingers drifted down to my balls. They were more vulnerable than the rest of my manhood. At this point she was just caressing, but I didn’t put anything past Jessica.
“Yes, but no.”
“What?”
“Yes, but no.”
“I’m a little drunk,” she said, making an understatement, “but I’m not that drunk. Explain.”
I continued to let her fondle me. I felt so vulnerable. “The whole purpose of chastity is denial. Denial to me, service to you. I’ll make you cum however you want: fingers, mouth, toys, or cock, if that’s what you want. I’ll make you cum whenever you want.”
“Interesting…”
“Some couples where the man is in chastity go months without PIV sex.”
“I don’t want that!” she declared.
“Okay, but can we go for a week?”
“No sex for a week?”
“No, I don’t get to be released for a week. You can have sex whenever you want.” I left it like that. I should be involved in her having sex, but I didn’t have to be.
“So next week, I get to take off your cage and do whatever I want?”
“You can do whatever you want, whenever you want. I’m in your power.”
She liked that. She squeezed my balls hard enough to leave me gasping.
“Did you like that?”
“No,” I grunted. “But if you liked it…”
“You’re turning into a pussy,” she told me.
“I just know what I like.”
We went to sleep in her bed, me in chastity, her completely naked. It was a good start.
Chapter Two
I woke up with my cock trying to get hard. Morningwood is the worst. It had been a while since I had worn my cage overnight and it still took a little getting used to it. My rolling over with a painful groan was enough to wake up Jessica.
“What? What’s the matter? Are you dying?”
Apparently my groans alerted her to my distress.
“No. Not dying. Just a bit of pain. Got to get used to riding the horse again.”
I rolled over to face her. My cock was only slightly swollen now. The head was visible through the lattice and while it wasn’t dark purple, which would have alarmed me, it was dark red.
She grabbed my cock and examined it. “That doesn’t look safe.”
I let out a little half-chuckle. “I’m used to it. Sort of. It’ll go soft soon enough.”
“When’s that?” she asked.
“When I get away from you and take a cold shower.”
With a knowing smile, she leaned over and kissed me. I could feel the warmth of her body and my cock was unsure of what it wanted to do: go soft and get the rest of my body comfortable or get hard and tell me to go fuck myself...and maybe Jessica as well.
“You said I could have sex anytime I wanted,” she said softly, letting the bedsheets fall down to reveal her body. I couldn’t help but stare at her tits. They were gorgeous, especially the left one where she had a silver barbell through the nipple. Earlier she had told me she had gotten it done with friends and after the first one she had chickened out on the second.
I sort of liked that she was semi lopsided. It was sexy.
“Yes…”
“And I want to have sex,” she finished for me as if she were explaining her needs and emotions to a child.
“Okay,” I readily agreed. “What do you want me to do? And please don’t tell me that you want to take off the cage. I really want to go a week before I take it off. I need to prove something to myself.”
She affected a look of insult. “I would never dream of doing that. But I did wake up horny so…”
In response I started to move down her body, happy to put my face to her pussy once more.
“No. Not that.”
I paused halfway to my goal.
“What then?”
She rolled over and reached beneath her bed. Dragging out a rather large shoebox she threw off the lid and revealed a small collection of sex toys. I saw at least three dildos, several bottles of what I assumed was lube, a silver toy that had to be a butt plug (and I wanted to ask her about but held my tongue) and a paperback book that could have been anything since I could only see the back cover.
Jessica grabbed the medium sized bright blue artificial phallus and, unexpectedly, handed it to me. “I woke up craving cock this morning. Since yours isn’t working right now, you’ll have to use this one.”
Flopping back on the bed she spread her legs open and raised her knees giving me easy access to her pussy.
“Lube?” I asked her politely.
“Please.”
I reached for the shoe box, which I now realized had to be a boot box, and grabbed one of the bottles. In the process I flipped over the large paperback. I wasn’t the least bit surprised to read the title. Anal Pleasure and Health.
There was no time to quiz her on her desire to have her ass used for sexual purposes. I flipped open the top of the lube, squirted some along the length of the vibrator and then drizzled some on her pussy.
She wasn’t wet, not yet. Or at least not that I could see. That didn’t stop her horniness, it seemed.
“Go slow at first, and then towards the end you’re really going to need to pound me,” she instructed.
“Can do.”
It felt a little strange introducing the head between her lips, but I found the correct angle and pushed it into her slowly.
“Mmmm,” she moaned. “Nice...go slow.”
I moved from between her legs to her side, and holding the vibrator in my right hand, I started to slowly move it in and out of her pussy. Laying on my side I could kiss her, which was nice, and I could lean down to take her nipples into my mouth, which I also did, savoring the left one more because it was pierced.
She lay back and let me do what I wanted, but unlike Janice the starfish, she gave me all sorts of feedback with moans and motions and, of course, instructions. “Faster. Turn up the speed. Faster! Harder.”
Faster and harder were her favorite words. It didn’t take that much time for me to get her to the point of orgasm, but my arm was getting tired. I started to understand why women wanted powerful vibrators that they could ram in their pussies. A halfway decent one would only take too long for them to get off before their arm muscles gave out.
For some women at least.
Abruptly she screamed out her pleasure and grabbed my wrist, preventing me from continuing to fuck her with the dildo, though I tried. I was certain what she needed was another little push to give her a second orgasm, but she fought me too hard and I stopped.
“That was fucking incredible,” she complimented me. “I think I could get used to this, keeping you in chastity.”
“I hope so,” I fervently agreed.
“It’s probably just the endorphins talking, but I want to make you cum.”
“That’s not possible, baby,” I assured her.
“I still want to do it.”
“Perfectly natural, but I’ll be okay. Just think about what it’ll be like when you do free me.”
“It better be fucking mind-blowing,” she told me.
“I hope so.” I grunted as I got up and went to drop the vibrator back into the boot box.
“Don’t!” she cried out.
“Why not?”
“It needs to be washed first. I don’t want a fucking infection from dirty sex toys.”
That seemed reasonable to me so we went to the bathroom where she instructed me on how to wash the vibrator. Using the bathroom sink was fine, except my encased cock kept hitting the edge of the vanity while I stood there, working naked.
“You look funny with a metal cock,” she commented, watching me from where she perched on the edge of the bathtub.
“You ever been fucked with a metal cock?” I asked her, grinning.
“No, but I’m willing to learn,” she smirked. “But seriously, I’ve looked at metal dildos and they are expensive.”
“Uh-huh,” I absently agreed as I dried off the vibrator with the towel she handed me. “What’s up with that book I saw in your little pleasure chest?”