This week’s theme “Orgasms” and the questions are brought to you by Naughty Tashamber.
Jack’s Answers
1 – Do you remember your first orgasm? How old were you? Tell us about it.
I remember quite vividly my first orgasm, or at least the first orgasm that I achieved consciously (if not deliberately) and was able to identify as such. I was twelve years old, and very aware of my budding sexuality. I had started masturbating several months before, and knew it felt good, but wasn’t sure what an orgasm was. I knew they existed, of course; I’d read the word in a number of places, but I had no idea what they felt like, and I didn’t realize that touching myself included an endgame. I just thought I was supposed to do it until…well, until I got bored, I guess. (It should be noted that it wasn’t something I did very often, owing to fear of being caught, and ostensibly my own Catholic guilt.) The first time I masturbated to orgasm, I was staying with my aunt and uncle while my parents were out of town. It was late at night and I was in their guest room. I don’t know what I was wearing and if I got naked or merely whipped my cock out of my pajama bottoms. I also have no idea whether I had any visual stimulation or just thought about naked girls, though I suspect the latter. I used the typical up-and-down stroke that has served me so well in the twenty-four years since, and when I climaxed I remember being puzzled by the intensity of it all. I enjoyed it, obviously, but it was over as quickly as it had begun, and I wondered exactly what had happened. I didn’t realize that the sensation was in fact orgasm until sometime after the fact, and it felt so good that I figured that it was probably bad for me. Incidentally, I believe that it was my first orgasm that made me realize that all the religious doctrine I’d experienced in my short life had to be wrong, or at least wrong for me. Up until that point, church was merely annoying and an unwelcome break from my weekend. But once I acknowledged the fact that the Catholic faith considered something as pleasurable – and harmless – as masturbation to be a sin, I knew I could never look back.
As anyone who’s read the Bible knows, bad things happen when you look back.
2 – What is your favorite way to orgasm? (Sex, g-spot/p-spot, oral, etc).
There’s no way I can narrow this down to a single favorite way. I’m inclined to say oral sex, but while the sensation of Jill’s skilled mouth coaxing me to orgasm feels so good that words cannot describe it, the fact is that I don’t always get off from oral sex. On the other hand, orgasms from vaginal sex are very exciting as well. And I’ve never had an orgasm from masturbation that I found disappointing in the least.
3 – Are there any ways you want to experience an orgasm but haven’t yet? (oral, p-spot/g-spot, with or without a vibrator, squirt, etc).
Yes, I want to experience an orgasm with many of our sexy female followers and online friends. Doesn’t matter how, exactly – I’m open to manually, orally, vaginally, or anally. I just want to cum with you.
4 – Have you ever had an orgasm in your sleep?
I don’t believe I have. I’ve never had a so-called wet dream, or experienced any of the familiar sensations of orgasm while sleeping. I don’t know why this is, exactly; my mind is almost always on sex, and it is frequently to sex that my subconscious drifts when I am asleep. While I dream of sex very often, and am frequently conscious of physical pleasure in said dreams, I generally wake to find myself rubbing against the bedsheets, and don’t usually do so all the way to ejaculation.
5 – What is the easiest/fastest way for you to have an orgasm?
I’m going to say masturbation, as even when Jill is not around I have two hands that are always up for the task, and hopefully I always will. Of course, when Jill is not around, my daughter generally is, and although she is very capable to keeping herself entertained while her Daddy takes care of his physical needs, she prefers that I remain where I can see her. Come late morning when I find myself in my bedroom with a fantasy and an erection, she usually notices that I’m missing before I can get off, and comes calling.
It is not unlike this.
6 – How many times a week do you try to reach orgasm?
Try? Maybe fifty. Succeed? Far fewer. As my daughter has gotten older she doesn’t nap much, so I am less likely to be afforded the privacy necessary to masturbate. As I said in my answer to #5, when she is playing or reading quietly and I decide to sneak off to pleasure myself, she will invariably not only notice that I am missing, but often she will come look and find me. Additionally, given a structural irregularity in our bedroom door and doorjamb, we have yet to find a commercially-available door lock that will fit and thus keep her out of our room. Additionally she has no trouble opening the bedroom door despite the child safety doorknob cover we’ve placed on it. On the other hand, Jill and I have been having sex four or five times a week on average, and in most cases I am always successful. When I’m not it’s once again our kid’s fault; I am convinced that she has some sort of moral objection to her father’s orgasms. But if I am ever forced to do without my orgasm because we’re interrupted, Jill always makes it up to me.
7 – Have you ever had an orgasm at the same time as your partner? Who normally cums first?
We sometimes have simultaneous orgasm during sex, though it’s never planned. It isn’t something we require because we both enjoy and want to appreciate the other’s orgasm without having to focus on our own at the same time. Typically when it happens we are aroused so intensely by the sight, sound, and feeling of the other’s pleasure that it triggers our own climax. Generally speaking, however, Jill cums first. I’ve always been pretty insistent that my partner gets off before I do. It just seems like common courtesy, doesn’t it?
8 – Can you have multiples?
I have had multiple orgasms once, and it was the weirdest feeling ever. Don’t get me wrong, it was totally hot and intense, and I’d love to do it again. But I wasn’t expecting it, and wish I’d known it was coming so that I could have enjoyed the experience more than I did. But I do not require multiples to enjoy sex; just knowing that Jill is capable of having multiple orgasms is sufficiently gratifying for me. I, on the other hand, have a very short refractory period (when I have one at all) and can fuck for hours, time allowing.
9 – How long does it normally take you to reach orgasm?
Depends on what’s happening. If I’m masturbating it can take as little as a couple minutes, though I prefer to take more time. If I’m having vaginal or anal sex it can take anywhere from a few minutes – I’d say ten on average – to forty minutes or more depending on the position we’re in. Not to brag, but I’ve never been the sort to cum quickly. And I imagine that some of my previous lovers have probably found that annoying.
10 – Have you ever faked one?
No. This seems like a difficult thing for me to do, being male. I can probably fake an orgasm if I had to for some reason. But faking ejaculation would be much more difficult.
I guess it’s more convincing if she’s blindfolded.
Jill’s Answers
1 – Do you remember your first orgasm? How old were you? Tell us about it.
I don’t remember my first orgasm, but I do remember having a lot of orgasms at age sixteen. This is probably because it was the first year that I had a room to myself. Growing up in a large family with a lot of siblings, I had always shared a room up until that point. But at age sixteen I masturbated on a regular basis. I would usually lie in bed at night and read Penthouse Forum. I had found my brother’s collection in his room, and he never seemed to miss the one issue I stole. Or maybe he just didn’t want to tell our parents that he was missing an issue of Penthouse Forum. I would get comfortable in bed, slip off my panties, and touch myself as I read with one hand. The magazine was just the right size to hold with one hand while my other was free to slide in and out of my pussy or make wonderful little circles on my clit.
2 – What is your favorite way to orgasm? (Sex, g-spot/p-spot, oral, etc).
It depends on my mood. My favorite way to have an orgasm is probably with Jack’s mouth on my clit. If I want to cum quickly it’s Jack’s mouth and a vibrator on my clit. If I want to feel as if I might explode into a million pieces, it’s Jack’s fist hitting my G-spot. Guaranteed squirting orgasms!
3 – Are there any ways you want to experience an orgasm but haven’t yet? (oral, p-spot/g-spot, with or without a vibrator, squirt, etc).
I have had orgasms in all of the above ways. I’m pretty fortunate to have an open-minded partner who loves experimenting with different ways of making me cum. In fact, Jack was the first person to find my G-spot and make me squirt.
But he might not be the last!
4 – Have you ever had an orgasm in your sleep?
Yes! I consider myself very lucky to have orgasms in my sleep pretty often. My dreams are often sexy to the point that I feel physical pleasure. I love waking up from an erotic dream to find myself soaking wet and my body convulsing with orgasm. It is so incredibly hot.
5 – What is the easiest/fastest way for you to have an orgasm?
The easiest/fastest way is a tie between being fisted, and having both Jack’s mouth and a vibrator on my pussy.
6 – How many times a week do you try to reach orgasm?
I try to orgasm at least once a day, so usually between seven and ten times a week. The orgasms can come from hurried masturbation in the shower or with a vibrator before bed, to long, hot, passionate lovemaking with Jack. Obviously I frequently have more than one orgasm each time, so I usually have more than seven or ten orgasms per week.
No smart-assed comment. I just wanted to show off a little.
7 – Have you ever had an orgasm at the same time as your partner? Who normally cums first?
Yes, Jack and I sometimes experience simultaneous orgasm. Jack almost always makes sure I cum first, and sometimes it is at the expense of his own orgasm if the baby wakes up before we are done. And even when we cum simultaneously, it’s usually my third or fourth orgasm.
8 – Can you have multiples?
Yes I can! I have multiples frequently, usually when being fisted by Jack, or when using a vibrator. I love the fact that Jack can read my body so perfectly that he usually knows when I want to have another orgasm, as opposed to when I am overstimulated or spent.
Unfortunately he never seems to know when we are overdrawn.
9 – How long does it normally take you to reach orgasm?
I don’t know that I have a “normal” timeframe between cold start and wet, orgasmic finish. When I’m aroused and ready to go I usually take about ten minutes, though I can do it quicker if I am in a rush, such as when I’m masturbating in the shower before work. I have been known to take up to forty-five minutes if I can’t seem to focus, if I am distracted, or more often if I am just trying to hold off in order to build the orgasm.
10 – Have you ever faked one?
Not with Jack. There’s no reason to fake it with Jack, obviously, and at any rate it won’t work out well for me to condition him to put forth less effort than I need to get off. On the other hand, other guys I’ve had sex with weren’t very good, and in those cases it was just more enjoyable to fake it and get myself off later.
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