Masturbated in front of a woman

a masturbator wrote:

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In my 29+ years since I first brought myself to an orgasm, the amount
of times I have jacked off in front of another woman could be counted
on one hand with enough fingers left over to hold a cigarette and
maybe even my television remote control. :-)  And, to be honest, those
few times were not under the best of circumstances…that’s a long,
sad story I will avoid telling for now, especially since what I’m here
to write about is much more pleasing.

To give some very brief background from posts I made in the original
OS…when I first discovered this group, I had recently made the
decision to be a “solosexual.”  I found that I was not happy in a
recent relationship because I was much more sexually fulfilled
bringing MYSELF to orgasm than doing so inside a vagina.  And, at
times, I was having difficulty ejaculating inside a vagina at all.

I have kept in contact with that “last woman” over they past couple of
years.  In fact, we even had a brief encounter during my disastrous
trip to Las Vegas earlier this year where, because we did not have
contraception, she satisfied herself by rubbing against my leg and
pelvis, and then she satisfied me with a hand job (although I had to
finish).

For various reasons, we were corresponding via e-mail while we were
both at work this past Wednesday and I got into a seriously horny
mood.  I decided to get a Jacuzzi suite at a nearby hotel.  We had a
great time pleasing one another for a couple of hours in all kinds of
ways.  She had already reached three orgasms sitting on top of me and
rubbing her clitoris against my erect penis, and I was now on top of
her near the end of this just plowing away and feeling great.  I
almost popped inside of her but just couldn’t do it — about half was
my already stated problem of only being satisfied with my own hand,
but another half is that I am still suffering from the tiring
aftereffects of the shingles.

I was so winded (and a bit sore) that I just had to stop and rest.  We
had a lot to talk about on various subjects and, for whatever reason,
I decided that I could and should start to open up to her about all of
the things I have talked about here and on my blog.

I am leaving out a great deal of detail and other issues here in order
to not be more boring than usual. :-)  But, on the subjects of
interest here, I ended up telling her over the space of 1 1/2 to 2
hours about my need to please myself, my deep want to do that while
enjoying pornography, how far back my history goes with those things,
my difficulty in ejaculating with anything besides my own hand, and on
and on — basically, the whole nine yards.

At least for now, it seems that I have a much more special woman on my
hands than I first thought about two years ago.  Not only was she
totally accepting of everything I told her, but she said that she
thought that’s what I was like even before the first time she
expressed interest in me.  Best of all, she doesn’t seem to have a
problem with any of it.

We spent this whole conversation totally naked.  Then, I finally got
up the courage to start doing it right in front of her.  She watched
as I lubed my penis with a blob of Albolene.  The, I got in my usual
stroking position on my back and began to rum my penis.  Through all
of this, she held me, kissed me, rubbed in all kinds of great-feeling
places on my body, all while I was totally naked in front of her,
stroking away just like a schoolboy.

One of the “problems” I had with her in the past was that she was not
very vocal in any way during sexual contact.  Some kind of verbal
feedback, whether actual words or just moans and grunts, is something
that I really need as I have aged.  So, I tried as best as I could to
verbalize some of my thoughts without making the whole thing seem like
a real-life phone sex session.  I started slowly and, in time, she
began to respond.  I was telling her how good it felt to do this,
especially in front of her.  She began to respond with whispers of how
it was OK for me to want to masturbate…that she wanted me to do
it…that it was natural…that she wanted me to feel good.

I am greatly shortening everything that happened, especially since
some noisy guests kept slamming their door just about every time I was
about to ejaculate.  But, I eventually got to a point where even King
Kong wouldn’t have stopped me, especially when she whispered that it
was OK for me to cum in front of her.  And, ejaculate I did with a
volume and force that I don’t normally experience these days.  It felt
so wonderful and satisfying, and with little of that usual post-orgasm
sleepiness or regret that we often experience.

After cooling down, we did try to get some sleep because we did have
to both be at work the next day.  But, after two hours of trying, the
noise and other discomforts of the room just wouldn’t allow it.  I
started thinking deeply about what had transpired, and I started to
get hard again.  As we all know, there’s usually no better sleep aid
than to have an orgasm.  So, I started rubbing on her and eventually
finger-fucked her into another orgasm.  Now that I had “paid my dues,”
it was my turn again. ;-)

I again lubed up in front of her and went at it.  On this second time
around, I noticed that she spent a lot more time actually watching me
stroke instead of looking into my eyes (which was also quite arousing)
or burying her face into my body as she licked or sucked all kinds of
places to make me feel good.  After some more of that (plus
interruptions thanks to paper-thin hotel walls), I again exploded
right in front of her…naked…playing with myself.

I can’t tell you how wonderful this was for me as somebody who has had
so few one-on-one masturbation experiences with either sex.  At this
point, I have no idea where this will go.  Will she get tired of it
even if I always satisfy her first (even with penetration)?  Will she
get jealous or offended if she ever sees the extent of my porn
collection?  Will I get tired of HER since I like such a variety of
porn and fantasies?  I guess that only time will tell.  For now, I’m
going to play it cautious — both in the name of my mind AND my
still-recovering body.  Whatever happens…wow…a real life
not-paid-for naked woman held me, touched me, and told me all the way
through that it was OK while I masturbated in front of her…and I
will remember that and masturbate over it until the day I die.

I hope that at least a few of you made it through all of that and
enjoyed reading about my experience.  I would love to hear similar
ones (either male-to-male or male-to-female) as well as any thoughts
and/or suggestions on what I should do or expect if I get more
frequently involved in a relationship where I am allowed and even
encouraged to continue my beloved masturbation and pornography habits.