The Life and Times of M.X.

We got in her car and drove off, after a while entering a not so nice part of town. She parked and led me to a shop called, "Sempiternal lust". The shop window displayed an impressive collection of dildos, vibrators and other sex toys. With reddened cheeks, I entered the shop. To my amazement, the gorgeous blond girl behind the counter greeted my stepmother by calling out her front name. Had she been here before? I'd never expected that. And then my stepmother spoke.

"Hi, Lisa. Listen, this is my stepson, M[...]."

"Hi M.," said Lisa. I managed to pull my gaze away from her perfect breasts, but it was just in time. You see, she was wearing a tight black tank-top which revealed the exact shape of her firm breasts -- and they were so beautiful: not too large, not too small, and so... firm. I mean, she wasn't wearing a bra, and her breasts were not the least bit saggy. And, due to her choice of not wearing undergarments, I had a splendid view on her hard nipples, which poked through the stretchy fabric.

"H-hi," I stammered, turning even redder.

My step mom spoke again, "Lisa, M. is a good boy -- generally speaking. However, lately he has some issues with... well, a leaky toy, if you get what I mean."

Lisa smiled at me and said, "Well, if you lack a girlfriend, but have enough hormones for two, life can be difficult..."

My stepmother sighed and said, "I know. But he has some size issues as well. Why don't you tell Lisa, honey? You know, about your little problem?"

I sighed, closed my eyes, and stared at the floor when I whispered, "I have a small cock."

"Speak up, honey, she can't hear you; and please be so courteous as to look her in the eyes when you address her."

I clenched my teeth and said, "I-I... I have a small... cock."

I looked up at Lisa. My cheeks felt like they were on fire, and my penis in fact felt smaller than it had ever felt before.

Lisa smiled and said, "Well, I have the perfect solution to your problem. Well, part of problem, that is. Only surgery can mend the size issue. Please, get into that fitting room over there and take off your clothes. I'll be with you in a moment."

I got in the little fitting room, closed the curtain, and took off my clothes, feeling very embarrassed. I sighed and waited. I couldn't overhear the whispered conversation between my stepmother and Lisa; all I heard was, "3000". While I was pondering the significance of that number, suddenly the curtain was yanked open.

Lisa stood in the opening. Now I could see the lower part of her body as well, which had been hidden by the counter up until now. Her black tank-top revealed her navel and her taut stomach. She was wearing a tight fitting, stretchy pair of grey camouflage trousers, which showed off her beautifully curved hips. She seemed to be in her early twenties. This was one gorgeous girl alright.

She giggled and said, "I see I'm beginning to turn you on. Well, we can't have that. Here, let me put this on you."

She kneeled in front of me and started to fumble with my penis. I bit my lower lip, trying everything not to get a full-blown erection; the situation was humiliating enough as it was. I noticed how Lisa clipped a ring around my balls and the base of my penis. Then she rubbed some baby lotion on my penis, and shoved it in a clear, curved, plastic tube. She aligned two little rings, put a little padlock through, and snapped it shut.

She got up, and stood really close to me for a moment, visiting my eyes with her beautiful green ones. She put her right hand on my chest, and softly caressed my balls with her left hand. She winked, and that was the signal for my cock to get hard. It sprang up -- and it was trapped. My penis strained against the clear plastic, but it was futile, I couldn't get an erection while wearing this thing, no matter what.

And then Lisa took my hand and walked me over to my stepmother again.

"I think this should do it. Whatever happens now, M. won't get this off. Only the Keyholder will be able to unlock him. Here."

And Lisa gave my step-mom two small keys.

"Well, honey, how do you like that? Your little dicky is safely locked away, so that you won't be able to give into temptation when it comes. And it will come, honey, it will. Now, this here is the ChasteBoy-3000, and as Lisa said, you will not be able to take it off. Only I will. As I promised, once a month I will take care of your ejaculation for you. But no more autonomous wanky-wanky for you. I warn you here and now: if I think you've done something wrong—anything—I will extend your period of chastity with a day. So from this moment on, you will obey me. Do you hear me, honey?"

I nodded and said, "Yes, Mom."

"Good, then get dressed."

As I walked back to the fitting room, two leather-clad, presumably gay guys entered the shop and smiled at me. One of them said, "I got one of those, too. You're in for a good time, darling..."

I sighed. While driving back, I could think of only two things: that damn chastity belt and that incredibly cute girl Lisa. When we got home, I walked inside, slightly awkward. It would take me some time to get used to wearing this thing. My stepmother had explained to me in the car that I still had to wear the butt-plug as well. In fact, she had bought a slightly bigger one than the one I'd been wearing up until now, while I was getting dressed. She had actually made me pull my trousers down in the shop, and had borrowed some lubricant from Lisa. While the two leather studs were watching, she inserted the plug into my rectum.

Well, anyway, I now had to get used to a bigger butt-plug (this one being about two fingers wide, and slightly longer than my middle finger) and to a chastity belt (which, hurrah, I didn't have to wear when I had physical education).

I had never felt so humiliated in my life as on that day. However, things were about to get worse. Even worse, that is...

CHAPTER III

Days passed, with me wearing a chastity belt and a pretty large butt-plug on a daily basis. One Sunday afternoon, Dad was fishing with some buddies, and my stepmother told me to come into her room. There, I was forced to strip.

She smiled and commented, "Good boy, wearing your belt and plug, and shaved neatly."

This shaving was quite a problem, because, when wearing the chastity belt, I couldn't shave. So every time I showered, she took the belt off and actually watched me shower. How she explained this to Dad, I don't know, but somehow she did. So she watched as I shaved myself, and how I washed. She explained that it was better not to shower with the belt on; although it was stainless steel and plastic, for matters of hygiene this option was best. Of course, being a "naughty boy", I had to be watched to make sure I didn't play with myself while showering. But anyway, on with the events of the day.

My stepmother told me to close my eyes, and I complied. When she told me to open them again (I didn't have the nerve to peek, because that would only result in more days being added to my period of chastity), my eyes grew wide. Mom had a cock.

Well, not a real one, of course. A leather harness around her waist kept a dildo in place, and what a dildo it was. It was so realistic, that I really had to look twice to make sure my stepmother wasn't a guy in disguise.

"Honey," she said, with that devilishly innocent voice of hers, "today, you are ready to learn the next skill a little loser boy needs to master. Do you know what it is?"

I shook my head.

She smiled and said, "It has to do with being on your knees."

I frowned and shrugged.

My stepmother giggled and said, "It's... cock sucking!"

I cried out, "What?! Cock sucking? Who the hell do you think I am? Or better, what do you think I am? I'm not gay!"

My stepmother shook her head, "Silly boy! You don't have to be gay to suck cock. You just need to have a mouth. Come on, admit it, you've thought about sucking off another man before. You've dreamed about it: kneeling and taking that big, juicy piece of man-meat in your mouth and sucking it until hot seed squirts out."

I shook my head and said, "Um... no, I haven't. Not once. Listen: I won't do this."

Mom sighed and said, "Listen, honey, this is for your own good. I've told you so many times before: you have a small dicky. And boys with small dickies have only one purpose in life: to serve others. Now, I present you with a choice. You are chaste for nearly two weeks now. In fifteen more days, it'll be the first of the month, and I was planning to let you ejaculate then. But if you're going to be a bad boy, maybe I'll postpone it a couple of weeks. So what's it going to be, honey?"

I sighed. And kneeled.

My stepmother stepped in and said, "Now, listen, honey. I know this is difficult for you. All these years you've had to pretend you weren't turned on by cocks, but I've known it -- all along. So don't worry anymore. From today on, you may suck cock. Now, because you do not have any hands-on experience, haha, note the clever pun, there, I'll guide you through the process. What you have in front of you is a realistic six inch strap-on dildo. Of course, it's only six inches, so it's not really a 'cock'. But as you're endowed with a similarly small dicky, I ought it wise to start with this size. Okay, step one. Grasp the shaft with your right hand, yes, just like that. Now, softly stroke the balls with your left hand. Hm-hm, that's right. Now, start licking along the ridge. Maybe you remember that this is a very sensitive spot, but I don't know, it's been a while since your last orgasm, hasn't it? Haha... Yes, pay special attention to the fraenulum, you know, that sensitive little band at the base of the head: flick it with your tongue, yes, just like that! Well, now I want you to lick around the head for me. That's right, lick it. You're doing just fine. Now, a nice personal trademark: kiss the tip. Yes, go ahead, kiss it. Excellent! And now, let the head slide into your mouth. Good boy. Wow, you can take it in pretty deep already. Are you sure you haven't sucked cock before? Really? Well, then you're just a natural, honey. Excellent. Yes, move your head up and down over the shaft, but don't just bob up and down: I want you to suck that cock in deeply. Coat it with your saliva; just like that!"

In the past few weeks, the term "embarrassment" had taken on a whole new meaning for me. I was shaving my manly pubic hair. I was wearing butt-plugs. I was wearing a chastity belt. I was denied orgasm. As if all of that wasn't bad enough, I was now... sucking cock. My cheeks were burning with shame. How could I have let this happen? There was no way back now. To the contrary, I entered deeper into this crap every day. I wanted to sigh in defeat, but I couldn't, because my mouth was stuffed with rubber cock.

"Yes, honey, you're doing pretty good. But do you know what? Here, stop for a moment. Wow, do you see that? You've coated my cock with saliva! That's a very good boy. However, you're not sucking a lollipop, here. What I want you to do now, is take this cock in all the way. That means it'll go down your throat, therefore, we call it 'deepthroating'. Can you do that for me?"

I shook my head, "No, I can't. I'm sorry, but it's too big for that, Mom."

She giggled, "Nonsense, honey. Porn stars can deepthroat real cocks, eight inches, nine inch ones, maybe even bigger ones. Are you telling me you can't even take in these pathetic six inches?"

What my stepmother didn't mention here, was that the problem was not just those six inches of length. Being a dildo, this thing was thicker than most cocks. Well, thicker than my own six incher, anyway. I sighed, and started to suck again.

"Very good, honey. Now, pay attention. If something goes down your throat, there are two major issues. The first is a gag reflex: you'll want to gag to get the intruder out. Reflexes can't be suppressed, after all, they are involuntary reactions to external stimuli. However, you can learn to ignore and overrule reflexes. So when you get the feeling you have to gag, I want you to swallow. Swallowing will make the sensation go away. The second issue is that of choking. Even with something down your throat, you can breathe, although it seems impossible at first. The trick is to breathe through your nose. Very slowly, with a lot of attention. Then you'll be just fine. Now, let's try it, honey. Take it in deeper."

I complied. I actually could take it in a little deeper than I'd been doing up until now. And then my stepmother started to make slow, controlled thrusting motions with her hips. She gently pushed the dildo farther inside my mouth. I immediately gagged, and panicked, but she grabbed my head with her hands, and whispered, "Careful, honey, remember now, if you gag, swallow. Here we go again."

She thrust again, and I swallowed. To my amazement, it worked. I felt the dildo enter my throat a little bit. I nearly panicked again when I couldn't breathe, but I stayed calm and breathed through my nose. That worked as well. Farther and farther the rubber cock slid down my throat.

Tears started to well in my eyes as my stepmother thrust rhythmically in and out of my throat. She smiled and said, "I know, honey, you get tears in your eyes when you deepthroat. Even I have that problem, but don't worry, you'll get used to it."

She thrust in and out, and I sucked her cock. After the eternity of twenty minutes, she said, "Okay, that's enough for now, I think." Gently, she retracted the strap-on dildo from my mouth. It was dripping with saliva. My stepmother said, "The saliva from the back of your throat makes excellent lubricant, did you know that? You should remember that for future reference; it might come in handy when you and your girlfriend make out and... oh, that's right," she giggled, then continued, "you're a little boy without a girlfriend. Well, it might come in handy some day, don't you think?"

I said, "nuh."

I wanted to say, "no", but no words came out. I looked at my stepmother, who was getting dressed. She nearly gave me a hard-on, by the way. She wore a frilly red thong and matching bra, a short yet classy skirt and a slightly transparent white blouse. God, what a fine body for a woman her age (hey, I was eighteen, for me anyone thirty-something belonged to the elderly).

My stepmother smiled and said, "Oh, I forgot to tell you that. Your throat will be sore for the rest of the day, and most likely tomorrow as well. You see, that dildo kind of forced its way in, and it may have irritated your throat a bit. Never mind, honey, it's not permanent, and, haha, you'll get used to it. I'll just write you a little note for school tomorrow, explaining why you can't speak. Why, I'll do it right away. Just a moment honey."

She sat behind her desk and scribbled a note, which she then read out.

"Okay, I've written this: 'Dear Sir/Madam, / Unfortunately, M. is unable to speak due to throat ache. Yesterday he gave his first blowjob. Well, to be honest, he actually sucked off a small strap-on dildo for me (and also attached to me, by the way). I think it was worth it, though: he really seems to like sucking cock. He's not gay, though, he's just learning skills to compensate for his lack of manhood. / Kind regards,' and then my name. Do you think that will do?"

I stared at her in disbelief. She couldn't be serious about that.

She was silent for a moment, and stared at me. And then she started to laugh.

"Hahaha! Oh my God, the look on your face! No, honey, even I am not that bad. I just wrote that things were a little rough on a party we'd given. Hahaha. Did you really think I'd let you hand that in? Am I that wicked?"

I was silent for a moment, smiled, and then rasped, "To be perfectly honest, Mom, yes you are."

CHAPTER IV

And so it went on. Every time my Dad was out, she made me suck her strap-on cock for at least fifteen minutes. I was still wearing the chastity belt, eagerly awaiting the first of August, when I would be allowed to come. I never thought I'd long for orgasm this desperately, but I did. And then, finally, it was the first, which just happened to be a Sunday this month -- Dad's fishing day.

My stepmother called me, and I eagerly entered her room, a smile on my face. She was smiling too, and said, "Today's the big day, honey... You get to ejaculate today. But I don't want you to do a quick wanky-wank. I'll assist you in the process. Please undress for me. Yes, that's right. Now, please put you hands behind your back."

I heard a soft click -- Mom had cuffed my hands. She took out the key to my belt and took it off. It felt great to be free. Of course, I was free during my showers, but now I knew I would come. My penis responded by immediately getting rock hard.

"Well, well, your little dicky is rising to the occasion, I see! Honey, I want you to lie down flat on your stomach. Yes, that's right. Now, I'll just put this blindfold on you. Very good."

I was on her bed, my penis feeling like granite. I noticed how my stepmother started to apply lubricant to my anus. She massaged my rectum very gently, which felt fantastic. I started to drift away, and focused on the pleasure.

My penis went soft again, because it did not get any attention. And then, ever so slowly, her finger entered me. She let it slide in and out of me at a very slow pace. The feeling was amazing; it felt like someone was tickling me very softly from the inside.

My stepmother took hold of my penis and pulled it backwards, between my legs. I felt how it touched something cold, and I startled slightly. She giggled and whispered, "Don't be afraid, honey, I just let your little boyhood rest on a saucer, so that you can be a good boy afterwards and lick up your sperm. After all, I know you love the taste of seed."

I started to say, "No, I d-" but she whispered, "Shh, honey, be silent and enjoy the moment."

She started to slide her finger in and out of me again. Slowly, gently, caressing. I felt a drop of precome flow from my penis, and I sighed softly. This felt great. Mom went on and on, and then she slid in a second finger. It was a tight fit at first, but she told me to relax, and that indeed helped. I was enjoying the sensual anal massage, and then I suddenly gasped.

Strange sensations coursed through my body.

"You like this, honey? I'm rubbing your prostate, now. You remember, I did that before while I was jacking you off. Today, however, I'll show you one of its nicer features..."

It felt great -- a little strange at first, but great. The sensation I felt resembled the urge to urinate, but it was different somehow. And then my stepmother started to massage my balls very gently. I sighed as I felt another drop of precome flow from my penis. I was blindfolded, of course, but I tried to imagine what my penis would look like, now. The head was probably coated in that clear, sticky precome fluid.

Slowly, my stepmother built up the pace, keeping the pressure on my prostate at a continuous high level. Now and then, I felt a drop of precome flow from my penis again. It really felt great. However, the massage went on and on, and I was getting slightly impatient. I gently wiggled my butt to make a statement, but my stepmother just kept massaging my prostate.

And then, at last, after at least three quarters of an hour, she giggled and said, "Did you like that, honey?" I felt her pick up the saucer and put it on the nightstand. Then she said, "Please get up honey, it's finished."

I carefully got up (being blindfolded and handcuffed doesn't really help in getting up from a soft bed, you know). Mom took off my blindfold and said, "Did you like that?"

I nodded and said, "Yeah, it was amazing. I've never felt sensations like that in my life. Absolutely amazing."

Mom smiled and said, "Excellent. Well, I'll just put you in your belt again."