Diary of An Unrepentant Sex Addict

Tuesday, June 21, 2005

Every Velvet Glove Fits Differently

Over at Overworked & Underf*cked, she asks her male readers (or lesbian readers, if they want to participate), to talk about their feelings on the feelings from within a vagina. How can I turn down such a request?

(She also wants us to focus on the vaginas, not the women attached to them. I'll try my best.)

Be it mental, physical or (most likely) a combination of the two, there are few sensations that stand out in my memories like the feeling the first time I penetrate a new lover. It's like the breathlessness you get from the first kiss, combined with the electricity you feel the first time she takes your erection in her hand, added together then raised to an exponent. From the first grazing of my glans on her outer labia, to the first full, balls-deep thrust, my nerve-endings are sending to my brain a series of memories I'll treasure long after the relationship itself (if there was one at all) has ended. This isn't to say that I remember all of my nearly 90 first-times (though to be fair, I also count oral-only encounters, so not all 90 or so qualify anyway). Truth is, not all of them were that memorable. The majority of the ones with sex workers weren't. But there are some that bear relating. Because the sex of an aroused woman is like a warm, velvet glove that grips with the most exquisite of caresses, and no two gloves are (or were) the same.

ML was my first, ever. And being first, there was nothing before her to use as a basis for comparison, so my memories of that glove are highly romanticised and wholly intertwined with the memories of her. Still, I remember every detail and aspect of that evening like it happened yesterday. From the angle of entry, to the embarrassingly-short time it took me to finish. She was on the pill, and AIDS wasn't a household word yet. I have the (now) rare priviledge of remembering my first time without a condom in the picture.

LL (see the previous entry), I remember very well. I didn't know she was a virgin at the time, but I do remember feeling a wonderfully strong grip. I naturally go slow on the first entry, just to prolong the joy, so luckily I didn't go in too hard or too fast. I like to savor the feeling, from the tip past the head down the shaft to the base, until I'm fully in. That first time, I remember her muscles clamping at the base when I bottomed-out that first time. LL had a stronger grip than I remembered ML having. I was more experienced, so I didn't orgasm in the first 30 seconds, but not for lack of opportunity. The gentle-but-insistent clasping around me could have finished off a lesser man in mere seconds.

JB was the first glove I got to enjoy for a protacted period of time. Our first time was nervous and circumspect, as we were in her mom's house at the time, not entirely sure mom wouldn't get home early. We didn't plan well, and no condom was used. After our second time, I came to my senses enough to ask her if she was on anything, and we started using condoms from then on. JB had a very slender, almost boyish figure and I think that contributed to the feeling of her. With her, the pressure from the glove was pretty much the same from just inside the opening all the way up the cavity. When she gripped me, the feeling was consistent along the full length of my cock, from the head down. Only at the very opening was there a stronger grip.

The next truly notable was PC, the person I ended up with for nearly five years. She was far and away the most experienced lover I've ever had, and it really showed in her muscles. She particularly liked to be on top. She wasn't the first lover I had to be on top, but she really knew how to use it. PC is unusual in that I don't remember the first time so much as the set of really stellar lovemaking sessions. She could literally make being inside her feel like you were getting blowjob.

Once I moved to California, as I've mentioned before, I discovered the joys (and convenience) of commercial sex. Few of those were worth recalling, at least in this context. Some of the women really rocked my world at the time, but didn't plant the kinds of memories I'm thinking of now.

But then EW came along. We ended up fucking the night we met. Not the first time that's happened, but the first time it happened and the relationship actually lasted. What I remember most about being inside her, was that she got wetter than any woman I'd ever been with. (She's since learned how to have a female ejaculation during sex.) All that moisture made the glove feel much softer and silkier. I also remember that my usual effort of going slowly for the initial entry was foiled by her grabbing my hips and pulling me in hard and fast.

So, out of the scores of gloves I've tried on for size, it's no surprise that no two were alike. No doubt that a good part of my addiction is simply addiction to the feeling of having that softness, that silkiness, enveloping me. Some gripped like a hand, some clamped like a vise. Some gently coaxed my orgasm out of me, some ripped it hungrily. The only thing I know for certain is that in order to make a definitive judgement, I must have more research.

(And in case anyone is wondering, I am in the market and mood for a new first encounter...)




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