Taking Matters Into my Own Hands – Masturbation Kink of the Week

Masturbation – Kink of the Week
It’s the year of the Orgasm around here so it only fits that I sit down in earnest and talk about Masturbation. Something I’ve not really done very much (writing about it that is). I’ll start with the questions Molly has posed as part of the topic then see where the mind goes from there. For all the things I can and do write about Masturbation in terms of my own practices has never been much of an area of literary focus for me. It has gotten little more than passing mention until a recent post. Yet as you’ll see it has factored into my own sexuality; that of my partners, and so many other parts of my sex life for as long as I can remember. It’s almost certain that writing this will cause me to pause, reflect, perhaps laugh, and at times be deeply uncomfortable with what I’m sharing. It seems so very personal but that may be tied to youthful misconceptions on the topic. So taking matters into my own hands let’s get this novella of self-pleasure (and the mishaps) masturbation has led to started.

Are you a regular wanker?
I love this question! And starting off on a humorous note. I am a fucking massively huge wanker in many people’s book. As for my actual wanking well that depends on the time period although masturbation is certainly part of my sexuality and sexual routine. Working from now backwards to once upon a time. Given my theme for the blog this year I have seen the amount I masturbate compared to the past two or three years increase in order to hit my 3 orgasm a week minimum target. In a lot of ways it’s made me a better more patient lover when with a partner so that’s a good thing. Not that there’s anything wrong with the occasional hard fast just need to cum grudge fuck. So why the slowdown in the preceding years? In part I’m sure it was age, some of it was lack of time, and a general frustration with my actual sex life/partner. Just about everything involving sex mad me angry rather than stimulated and enjoyable. (A post on what else changed seemingly for the better will come out next week.) So perhaps some insight into why I picked three orgasms a week. Three is the number that (historically) keeps me from being on edge and a sexually frustrated asshole. Generally speaking I have good control when playing with an established partner and the ability to last. It’s also a manageable number given a variety of options in a busy life..

When did you first start masturbating?
The first time who knows? Like most males I knew I liked having a penis fairly early on. As for using it for any form of pleasure (other than writing my name with piss in the snow) with any regularity and purpose was around 11 (and in the 5th grade). In those days my early my masturbation fodder was of course my class mates. By 13 I could Jerk Off (nearly) endlessly…and did. Three or four times a day at points for days (or weeks) on end. It was well into my 20’s. It wasn’t uncommon and always it was based on based on how sexually active I was elsewhere. More than two days without cumming and it was time to take matters into my own hands. For the most part even with daily sexual activity I would still use masturbation two or three times a week for additional sexual releases.

Was it a wonderful discovery or a shameful secret? “Maybe you were bought up in a environment where you were taught that touching yourself was ‘devils play.”
I’m not sure it was shameful but it was certainly a secret (at first). While the concept of it being a sinful action never came from home the good Catholics around me made sure we knew that “any type of sexual pleasure that was not open to the possibility of conception and within the confines of a marriage was a sin.” So of course that made it all the more appealing. Yet looking back self gratification was the punch line of endless jokes about hairy palms, going blind, and something the mentally ill did.

In retrospect there probably was an element of embarrassment that kept it from being a topic of conversation during those years. Still I didn’t lie awake at night worrying that blowing my load into a tissue was going to get me a hotter place in hell. I never thought I’d go blind but a few times did think I might wear down the head of my penis. Of in the best case scenario end up with a huge callous on the underside of the head. No I’m not kidding, I had wondered/worried about that at a few points.

How did this effect you and your exploration of your self pleasure?
It really didn’t. Other than being somewhat discreet and it not being a topic of open and honest conversation even with sexual partners and friends my self exploration and masturbation morphed and changed. It included using various lubricants to keep from getting sore/raw. At first Vaseline and at times huge amounts of it. Then was the discovery of KY lube first used on me for a hand job by a girlfriend that got added to my own arsenal. As my sex life became more regular I would jerk off into condoms, as a way of trying new brands and seeing how they fit and felt before using them with a partner.
Sheik were always a favorite. Durex had some great one and at the time Trojans felt like your dick as in an inner tube. Thankfully they have gotten much better.
Do you like to use sex toys when you masturbate? Maybe you have a favourite toy or maybe you prefer the joys of your own hand/fingers and nothing else.
My own hand is by far the preferred method. I’ve become more particular about lube type (Sliquid followed by Astroglide because they have one use travel sized lubes) if given a choice but not so much so that it’s a requirement. On very rare occasion I’ll add a bullet vibe on my balls for extra oomph. It does increase the intensity of my orgasm just like when the same tactic or a hand is used for additional stimulation during other sexual acts.
Over the years I’ve masturbated with a number of different sex toys; most of them are not at all noteworthy and all but a few were gift from partners. Here are a some examples.
Penis Pump for Masturbation
The very first was a penis pump from a college girlfriend. She bought it a porn shop on a Friday night so you can imagine the quality but back then it felt adventurous. The pump occasionally (maybe 3 times) saw some solo play. Mainly she liked to watch me use it and was fascinated by both the size change in my cock as it hardened and also my orgasm. Literally it was almost a question and answer session every time. More of a play by play rather than taking dirty but no complaints.
Pocket Pussy Jerk off male masurbator
Another lover gave me an old school mouth themed masturbator to use when she’s “not available to blow me”. It was fine but never a favorite and the cleaning and storage of that damned jelly thing and other pocket pussy themed jerk off toys are probably why I’ve never even seriously considered a Fleshlight (which has to be an improvement).
Magic Wand Vibrator Penis Head Male Masturbation attachment
Just this year I’ve added some male third party attachments that go on the Doxy I bought for the Blonde. It was done on a whim based on a short video clip on Tumblr and really as an act of cynicism. I expected to be underwhelmed at best but have to admit they feel awfully damn good and produce ball draining orgasms no matter how much or how recently I’ve cum. Toy wise these are by far my favorites ever with the “Vibrating Head” being favored over the “humming bird” model. Eventually I’m hoping to find silicon versions of them some point.
Does masturbation feature in your relationship?
My Primary relationship it really doesn’t. In fact it’s something that has never really been discussed in detail and makes her feel deeply uncomfortable. I blame religion and the shame it carried in her youth. It’s a nod and a wink kind of thing. Masturbation has/does at other times feature as part of the relationship with other partners. More so theirs than mine.
Is watching your partner getting off is seriously hot or something that makes you uncomfortable?
Hot? Yes! Seriously fucking hot. So rather than retell history here are two examples. Watching Her Cum from a few years back and another partner who briefly re-entered my world in Spanked and Self Gratification. Watching my partners get them selves off really works for me, it can have a D/s component to it, teach me about how they like to be touched, how they react when they are near the edge, and when they go crashing over it into that ecstasy that is an orgasm.
Or course it doesn’t end there. Looking ahead I have a few scenes that will feature my partner’s masturbation in front of me that will hopefully get played out. The settings are picked. The build up’s planned and the toys arranged for (or identified). It turns me on just thinking about what I’ll get to see, and learn about them as they get themselves off in a variety of ways.
Alternatively how do you feel about being watched?
This one is a mixed bag. And that is based on mixed experiences I’ve had when being watched. Penis Pump girl was fun and harmless. I was young and in peak shape so you could watch me doing anything at any time I could have cared less. Add to it that I’m not a CFNM kind of guy. A lot of guys are and get off on that which is great for them.
A Neutral Masturbation Experience
One partner liked to suck me hard, have me masturbate to the point of release and then would take my cock in her mouth and then get off on vigorously swallowing my cum. I neither really liked or disliked this and at times thought it was a bit inattentive on her part. Yet there was some internal narrative in her head that was never shared but made it hot for her so I’d play along. Oh did I mention I got to have an orgasm so who could blame me?
Positive Being Watched Experience – “Cum on me Here”
Mutual Masturbation counts right? She was a bit of a “cum junkie”. Yes an impolite term but her words not mine. She would strip and tell me “Cum on me here…” the location always changed though stomach seemed to be most popular as she would try to time her own orgasm shortly after mine. Excluding ears and nose at one time or another I came on about every of her and much of that was masturbating while she watched.
Negative Experiences of Being Watched – I have been asked to be watched and had a few react negatively when they did. Not my kink that’s for sure. Frankly bothered me then and even now when I think about it. Who knows what they were wanting or expecting? At the time I was young(ish) and it turned me off to the idea of being watched while masturbating. Watching my partners is much more fun for me and always has been.
What do you think about when you masturbate?
What do I think about? You! My partners, what we’ve done and what I want to do to (or with) them. My kinks play a big part of all of my sexual out lets. I think about what turns them on, what makes them cum, what they let me do to them because it gets me off. Equally important is probably telling you what isn’t thought about, Nothing that is pure vanilla, if it pure fucking and not true kink it’s hard and fast. Heaving breaths and bodies colliding with ample lust filled force. But mostly it’s kink or kink related sex.
Is there a favourite, orgasm guaranteed, fantasy that you like to think about?
Continuing with the answer above. Spanking is a go to for my orgasms. She is bend over bared and marked, She quivers at the thought of another swat, can barely take it but does to please me, to test me, or to see if I can break her will to take everything I will put her through. There are always others but the go to ones always involve her submission to me in some way. shape, or form. Whether waiting for me under a table to finish so she can orally please me, letting me edge her time and again until she begs to cum. You get the idea
Do you like to watch porn, or maybe you prefer the stimulation of the written word?
It’s a mix of everything but mainly my own fantasies. Look i write a sex blog so porn is like coffee in the morning, pretty normal.  Not surprisingly BDSM, Bondage and Fetish/Spanking Porn is a fairly regularly consumed item for me but I don’t watch it specifically to masturbate to but can be a go to thing for me there is a bank of scenes I can replay in my mind if and when needed.  Now Fucking to Porn is something I like.
Wow that’s a lot of words. 2256 prior to the postlude to be a little OCD about things.  At the end of it all, taking my own practices and sexuality out of it I can’t help but think about how much better adjusted our world would be if people were taught to accept and embrace normal healthy behaviors like masturbation rather than clouding them with shame, guilt, and other negative feelings.  How much more fulfilling our interactions with our partners would be from the beginning if we understood out bodies, needs and wants better…of course also learning to communicate them  as well.
I’ve asked myself the question why don’t i write about masturbating as more than a passing reference prior to this? Is it tied to hidden feelings of shame? Unlikely at this point in life. Is it because of a cultural Taboo?  Perhaps but again unlikely. I’ve come to the conclusion perhaps incorrectly that once we are adults we take charge of our sexual desires and needs, sometimes in our 20’s, sometimes in our 30’s or 40’s but for those of us that are lucky enough it happens.   and I tend to believe part of that is understanding your own body through masturbation and everthing that accompanies it.

This is a double MeMe post so Click the banners below to see the other Kink of the Week and Masturbation Monday Posts


The Hatless Stranger's Sexual Fantasy

The Hatless Stranger’s Sexual Fantasy

First Up The Reality of what Happened
Its late afternoon after a 500km drive into what can only be considered Eastern Europe.   I’m by all accounts a stranger in a strange land but have wonderful hosts. I don’t speak the language, literally not a single word.   Not that it would stop me from tying to pick up a few of the basics along the way.   After speaking to a room that stared at me blankly for an hour where my humor, intellect and every damn thing else was met with blank stares fell to people who I would later learn where too shy to speak to me.
After all I cut a terrifying image everywhere I go. Ok so not really but have been told by friends, acquaintances and strangers countless time apparently I have a presence about me. The response is typically something about me being a handsome devil.   I mean the devil part; the handsome bit is just a way to soften the evil overlord just waiting to be conjured. Any how the session wraps. I thank everyone and begin making plans for the evening.
I get to go out with my new local friends and an old buddy who knows about my proclivities. We are both some form of ladies men (male whores, perverts or whatever), with different interests. His are a bit more traditional   In comes a man with two women one of which is a dead ringer for the original model from Spanking Teen Jessica. It was an odd reaction to see a person and realize they are literally the doppelganger for a kink model whose videos you watch but my poker face rarely betrays my thoughts and holds true. My buddy pops right up and introduces himself, a big smile, hand extended type A Hi, I’m X! Nice to meet you”
Panic strikes her like she is trapped with a set of terrifying monsters about to kill her in a slow painful way before devouring her soul with cappuccino for dessert. Truly there’s not a better way to describe how afraid of us she appeared. Being fairly in tune with those around choose to introduce myself with a soft wife and slow gentle movements. Her discomfort is palpable. Later I’d learn she’d never met a Brit before and had never spoken to an American. A concept that was in fact terrifying to her because as a rule they are generally a shy culture with westerners, have little spoken contact in English although read and write in that tongue daily. I can’t shake the image of the onetime model she so strongly resembles. And make a joke about apologizing for being a bad American by not wearing a cowboy boots and hat. With that she smiled; somewhat sheepishly, held my gaze for a second before looing down again. Her body langue realizing momentarily. It was obvious that was exactly what she expected when the trotted her in to meet the “visiting American”. Sorry to disappoint but in the end I’m just another hatless stranger.
Food from an after the fact sexual fantasy. It’s roughly 28 hours later, in a different city. I’ve been away for four days and hadn’t cum in five and was at the point of needing to. There were no arrangements for a tryst or lover of any type in the next 8 days. It was time to take matters into my own hands given that situation (and three orgasms a week quota for the year). The thoughts began as they often do, they went to people I’m involved with or have been. My cock stiffening. Then they usually start to drift to acts either with some of those people or countless acts that are locked in my mind. Not this time the fantasies started to drift to a combination of the long ago spanking model I had watched in videos but then she faded and turned very specifically the young woman I had met. Sure spanking fantasies often factor into my orgasms this one was different. It was stranger but one I had met. A very uncommon thing for me to think of. My wank fodder isn’t random people…interesting in its own right.
Her shyness danced in my fantasy as a form of submission, thoughts of taking a heavy and severe paddle to her petite athletic bared bottom swam in my mind. Her now glowing and pain filled butt tensing waiting for another cruel swat and upon the last one she could possibly have taken lowering my zipper, unceremoniously lubing her rim and the head of my cock before fucking her ass. Driving slowly and deeply into her time and again then it was inevitable that it would lead to roughly that tight hole of hers. My hips pounding against her marked and bruised ass from the paddling as the pace of the fucking increased. She fingers herself to orgasm as pain dances with pleasure. Her tensing and bucking harder against me makes me cum.
Postlude – Often I get lost in my own head. Not just with sexual thoughts but intellectual pursuits and reflection in general. This piece is somewhat different because for all the varied things I write about, including so many things that get me off with others, acts, kinks, body parts and motions there is no memory of me writing about a specific fantasy I masturbate to let alone one that for whatever reason was truly unique and random in those moments. It is a topic I’ve largely kept to myself and left unexplored here. It feels in a way overly personal to be sharing, too much of a look into my head however in the same breath somehow seems overdue.
Note: timing is an ironic thing. This post was written literally on April 29th and scheduled for May 2nd.  On the First  Molly announced Masturbation as the Kink of the Week so i’ll be writing on the topic again shortly.