People are always pestering me about whether my
stories are true or not. Well, this one is true, but
it is in two parts. Look for the time shift near the
middle of the story.
My new friend Jamie is almost a perfect match for me.
OK, she doesn’t have the depth of perversion that I
do, but she does have my openmindedness. It has been
a real pleasure getting to know her, and also having
sex with her.
A little more than a week ago, we arranged to meet for
more than the quickie we usually enjoy. I was having
a hard time in my life, and she wanted to give me
something special. Accordingly, I brought all the sex
toys I owned, and which were gathering dust through
disuse. My wife wouldn’t use them with me, so they
sat sadly idle. Jamie would change that.
We kissed hello and I secretly admired her new
haircut, then I showed her my toys. My toy collection
isn’t huge, consisting of a buttplug (size: large),
“ripple stick”, huge pink dildo, and a strap-on. I
showed Jamie all these things, then suggested she try
on the strap-on harness. The thing is unnaturally
complicated, so I helped her adjust it so that it fit
her.
This particular harness has a unique mount for the
dildo. There is a base that has a prong to attach
different toys. The prong-base uses snaps to attach
to the inside of the harness and the toys stick out
through a hole in the harness. I guess the general
idea is to allow easy changing of the toys, but mainly
I just noticed the hole because without the pronged
base you could see Jamie’s pussy.
I was kneeling and adjusting the harness straps when I
saw the hole and the cute clit that was visible
through it. It was a simple matter to lean forward
and give Jamie’s clit a friendly kiss. Then another,
then some slobber and another kiss. You get the idea.
The neat thing about eating pussy through the harness
hole is that my attention was completely focused on
Jamie’s clit area. I mean, the hole is maybe 1.5″
across? That was the extent of my attention, and
Jamie was soon moaning in that ultra sexy way she
does. I managed to suck some pussy flesh out through
the hole, but she came soon after that.
Jamie was open to anything more I wanted to do, but
actually asking to be fucked was sorta embarrassing.
I hemmed and hawed for a few moments, then asked if
she would do me. Of course she said yes, but she
needed to know how to do it because she was a virgin
in this respect.
I decided to start with first things first. I
loosened the harness and put the dildo through the
hole, then snapped it into place. Voila! Jamie had a
dick! It was a very different sensation for her, with
the heavy weight hanging from her front. She gripped
it man-style, waving it around. It was cute to watch.
Being oral in more ways than one, I showed Jamie how I
could deepthroat her new cock. That was fun for a
while, but time is always our enemy when we are
together. If I wanted to be fucked, I needed to get
that part going.
I told her I needed to be lubed up, because I wanted
her cock in me. I had brought some latex gloves, in
case she had a problem with the messiness. She
didn’t, and I bent over the bed as she grabbed the
lube.
The initial touch of her finger on my asshole was
electrifying. She was touching my taboo spot, and I
loved that mental image. Her finger was wet with
lube, and she pushed into me. Not really sure what to
do, she did it pretty damn well anyways. She fingered
me for a minute, until I asked her to use the ripple
stick on me. The ripple stick is a rubber dildo with
ridges that ripple down the shaft. It has a handle
that makes it easy to thrust, and is maybe 12″ long
and 1″ across at the widest ripple.
I am always too eager in anal sex. I never give
myself enough time, so the ripple stick hurt. It hurt
enough that I took control of it from her, and
inserted it into myself. Once it was in and I was
relaxed, she took over again. Oh fuck it felt so damn
good to have Jamie fucking my ass! Listening to the
brraaappp of the ripple stick’s ridges going in and
out of my hole was exciting as well.
I began to beg her to fuck me. Well, beg is maybe the
wrong word because she did it right away. She pulled
the stick out of my ass and inserted the tip of her
cock at my back door. Wow, when she slid it in it
felt so fucking good. I’m not sure, but I may have
moaned!
Jamie screwed me for a few moments with her cock, but
the angle was wrong. She was standing beside the bed,
and I was on my back, legs up. I grabbed a pillow and
wedged it under my bottom to make the angle better for
her. Then she began to truly fuck me.
Gotta say, the feeling of being fucked is like nothing
else. I mean, I wasn’t responsible for any of my
pleasure. Jamie did all the work, jamming her dick in
and out. All I had to do was enjoy it, and I did.
Feeling her hips slapping my butt was intense. So too
was the feeling that I was being so slutty, my ankles
in the air so she could penetrate me fully. It was so
wickedly wanton!
The other part that was exciting was seeing her
reaction. In short, she was smiling just seeing how
much I was enjoying it. She was studying me intently,
learning how much I loved having her cock in me. Her
acceptance of the act was uncommonly pleasurable to me
mentally. Later she told me she would fuck me again
just to see the expression on my face.
One odd fact about being assfucked is that while it
feels so good, I sometimes don’t get erect. Its like
those parts are disconnected somehow. But,
eventually, I get the feeling like I need or want to
cum. Bad. It took maybe five minutes of Jamie
screwing me hard before I was ready to explode, and
yet completely limp. So, I began to jack myself. In
about fifteen seconds, I was mighty hard.
As I felt my orgasm beginning to overwhelm me, I told
Jamie to keep her cock in me. I didn’t have time to
explain, but somehow just the exact opposite happened.
She fell out of me as I came (maybe I was
thrashing?), then couldn’t put it back in as I
convulsed. My entire ass spasmed and I shot a huge
load over my pubes and stomach. Then, I pretty near
passed out.
Afterward, as Jamie scooped up some cum and tasted it,
I explained why I wanted her in me. Like many women I
know, the pleasure of an orgasm is increased when
there is a cock inside that you can squeeze. Having
my asshole pried open by the dildo, and being able to
squeeze it, provide an even more intense orgasm.
As it was, we both laughed about the amount of cum I
had shot. That’s one nice thing about being strapped;
the amount of ejaculate is hugely increased.
Jamie gave me a washcloth, and I cleaned up the mess
on myself. Then, we parted ways, commenting as always
that we wished there was more time.
A few days later, I remembered I had a meeting the
following Friday (last Friday) downtown. It was about
a month after we had first met, and it was a good time
to spend a little extra time together. No need to go
to the office, and my meeting started at 9:00, so we
had more than usual time to spend.
We made a tentative date, but as things happen, she
was worried about her period. She is not exactly
regular in her cycles, which is how I came to eat her
cherry pie a few weeks earlier. She also doesn’t
flood (at least I haven’t seen her flood), so I don’t
have much problem sucking her still red pussy. A
little cleanup of the obvious bits, and I am happy.
Jamie though, was amenable to strapping me if she were
still on the rag. That got me all hot and bothered,
and I certainly hope that her strapping me is the
standard fallback plan for when she is OTR. Thursday
night, she was certain of it because her flow had
picked up again.
Thus I arrived, certain I was about to experience her
cock again. Overnight, though, her flow had ceased
altogether and she was clean as a daisy. To
celebrate, I immediately went down on her after
shucking my clothes.
I don’t know if I have mentioned this before, but
Jamie is waxed. Her pussy and pubes are completely
smooth. This is an incredible turn on for me, not
because I fantasize about little girls (YUCK!) but
because I love sliding my tongue on her smooth skin,
with no fear of gagging on pubic hair. Her hairless
state really activates my oral desires.
With the little extra time, I decided to tease her. I
have an idea of what she likes by now, so I carefully
measured out my pleasure for her. I’d lick that
smooth vulva of hers, then suck her clit until she was
squirming, then moved on. I let her excitement rise,
and then I would back away so that she was at a higher
plateau.
Her tension mounted until she was at the breaking
point. She literally started shaking before she came,
and was quite noisy when she went over the line. Her
squeals of pleasure as she came was very exciting,
with her bare pussy grinding up at my adoring mouth.
This went on for quite some time, as if she were
having multiple orgasms.
Finally, concerned, I stopped. She laid there,
nipples extremely erect and chest heaving. She was
glorious to look at. I felt like a fool for asking,
but I wanted to know if she had orgasmed. With a new
partner, you ought not take anything for granted,
right? She assured me she most definitely had, and I
moved next to her and we kissed until she was a little
more energized.
It was my turn, which makes me vaguely uncomfortable.
I get so much pleasure from giving pleasure, it is
hard for me to accept it. I knew Jamie is much like
me, and it would be selfish to not allow her the
pleasure of giving. So I leaned against the
headboards, watching as Jamie prepared to blow me.
Jamie is practically the only woman to ever have
sucked my cock. My wife did, once, before we were
married 16 years ago. Until meeting Jamie, I’d had a
long dry spell. Honestly, I wasn’t sure I would enjoy
it, and have been overly tense. Since then, I have
come to appreciate Jamie’s oral gifts.
This time was the best yet. Jamie fucked my cock with
her mouth, sucking enough to make me respond with my
hips. She was watching my reaction, judging what was
giving me the most pleasure. Locking eyes with her as
she had my cock in her mouth was extremely sensual. I
began to wonder if I would enjoy another snowball or
eating her cum-filled pussy more. It was a toss-up.
Soon, she began sucking my nuts. Wow! I had never
had someone do that, and it was plenty good feeling.
I began to moan despite myself. It felt wonderful!
Every now and then, she would suck my cock a little
more, then my nuts. I was in heaven.
Actually, I was only on the cusp of heaven. She
detected my hip thrusts when she was sucking my sack,
and dropped her mouth lower and lower. I desperately
wanted to feel her tongue on my asshole, but I
couldn’t bring myself to say so. When she did, I
thought I might spurt. It was a very close thing.
Her little tongue swirled around and around my
browneye, getting me oh-so-close to blowing my wad
again.
Suddenly, she stopped and moved up. She kissed me
passionately with her cocksucking and ass eating
mouth. Oh, that felt so amazingly erotic and taboo!
Exploring her mouth as she explored mine was super
sensual, especially as she swung her legs over my
hips, preparing to mount me.
After our early fuck sessions, we had developed a
plan. In short, Jamie was always going to sit on my
face afterwards so that the creampie would drain out.
Gravity would be our friend. Of course, I’d told her
how much I loved having her ride me cowboy so that she
could slide up and plant her glorious puss on my
mouth. So, having her ride me like this was an
indication of what was to come. Yum!
I warned her that she had got me really primed to
explode. She told me that it was OK, to go ahead and
fill her with semen. It only took a couple minutes
for me to do exactly that. After eating her, getting
sucked, and having my balls and asshole cleaned, I
gave up another big load.
My wife likes to stop immediately after, but Jamie
rode me until I was nicely deflated and was about to
plop out. She got this look on her face, like, “get
on your back and prepare to eat it, slut”. My eyes
went wide as I understood I wasn’t being given a
choice.
I flung the pillows out from behind my head, and laid
flat. Jamie slide forward, plopping her gooey cunt on
my face. She has a nice headboard, wide enough to
grip, and she used it to balance herself as I ate her
voraciously. The creampie actually came out quickly,
a hot stream of delicious syrup that almost scalded my
mouth. I gasped with pleasure, sucking her pussy.
I ate her for I don’t know how long, nor do I care.
Her bald, oozing pussy was my world and I was going to
suck her until she came again. When she did, she
ground her moist crotch-cleavage on my face. That
made me wish I was young enough to get it up and do
the whole thing over again.
Soon, I was dressed again and about to leave. As
always, I wished we could do it for longer.