One of Tracey's "things" is to enjoy sex with strangers.  it is encouraged by both her husband and me and one of the tasks i have assigned her is to keep a diary of these missions. 

Here is march 09's

It was an unusual evening, filled with odd surprises, but on the whole I
would have to say that I enjoyed myself immensely.

It was a Tuesday evening and I had spoken to him on the phone the night
before, finalising arrangements, coming to an agreement on what our mutual
expectations were and which of these might be attainable, so I was not
completely unprepared for what might unfold. Or so I thought.

From our discussions, I had surmised that the man I was to meet for coffee
that evening was approximately 50, greyhaired, and probably fairly largely
built as he was a chef, and self-proclaimed lover of food. I was not far
wrong, but I'm getting ahead of myself.

The agreement was that we would meet at the marina for a drink, then if we
clicked, go for dinner, and if during dinner we decided that the other was
not really our "cup of tea" that we would politely call it a night and go
our separate ways. That was the plan.

We were to meet at 18:30. I had finished work, bathed, washed and styled
hair, shaved all of the vital parts, trimmed a few others, dressed in three
different outfits, settling for a mid-length skirt and semi-transparent
black blouse with heels and bare legs.

By 18:25 I was driving just slightly faster than I should have been, but not
recklessly. I was queasy with nerves, as I had been all day, running on an
empty stomach because I didn't trust myself to keep anything down, but
driven by adrenalin and probably a little cortisol.


Finally, at 18:28 I pulled up at the marina and found the place which S had
directed me to. It was quiet, but not unpopulated, and I felt reasonably
safe in the company of these strangers. For a moment I felt as though they
all might suspect why I was there and imagined various looks of shock and
derision on their faces, but of course realised that this was merely my
imagination. Of course there was no way that they could know.

As I approached him, he turned to greet me, a look of genuine surprise on
his face, but a reassuring smile as brought as the proverbial Cheshire's. I
could not help but smile in return, despite my sudden trembling. I had to
sit down immediately, for fear that my legs would buckle beneath me. He must
have seen this as he reached out to steady me and guide me onto my seat,
which was a bar-stool.

We greeted eachother with a kiss on the cheek, demurely, with not a hint of
the lasciviousness which had tempered our preceding conversations.

He had pre-ordered a glass of wine for me, which I gratefully sipped at
while trying to regain my composure and think of polite conversation which
might be appropriate for a meeting like this. I had no idea. The whole set
up was so foreign to me.

The harbour lights helped to steady my nerves slightly and calmed me enough
so that I started to relax and enjoy myself. No pressure. If you don't like
him, you can thank him for the drink and politely go home, untouched, and no
worse off for the excursion.

I noticed then how he was staring at me and couldn't help but laugh. He was
kind enough to say he couldn't believe I had arrived, nor that someone like
me would be in a situation like this. Presumably he meant he didn't think
someone like me needed a situation like this in order to have sex, but then
I didn't need to. I wanted to. I craved it.

And so, a few drinks later we were talking freely and laughing quite a bit.
A touch of his hand to my leg, or a brush of the hand on my back... small
gestures, but the signals clear...

Finally, he asked if I was happy to proceed to dinner and I agreed. That was
when he informed me that he had arrived not via his own vehicle, but via
taxi, and that he could either get to the restaurant in the same way, or by
driving with me. A cunning plan indeed. I had to laugh at this, but agreed
that he should travel with me.

It was then that he leaned across to me and whispered an instruction to me
which took me completely by surprise. In fact, I was so astonished, I didn't
know what to do, so I simply complied. I took a walk to the nearby ladies'
toilets, closed myself into a stall and removed my panties. The black satin
ones which I had deliberated over. I returned to S, and as requested, gave
him the bunched up underwear, suddenly fearing he would hold them up on
display for the other patrons.

Fortunately, he did no such thing, but instead sniffed at them momentarily
before placing them in his pocket. Few things could have surprised me more.

I didn't know what else to do, so I laughed and led the way to my car.

We got in and I started driving, needing to follow his directions, as I
didn't know the area well that he wanted to go to. As we drove, he reached
over and started running his fingers up my neck. That simple touch in my
heightened state of awareness sent me into an instant state of arousal. I
made a point of focussing on my driving, for fear that I might kill us in a
moment of distraction. It appeared that he almost wanted an accident to
happen, because he wasn't content to leave it at that, but instead, started
to touch my breast, lightly tweaking my erect nipple through my sheer
blouse.

His hand then moved to my thigh, and snaked its way to my vulnerable venus
mound, and the rapidly warming area beneath it.

Without the security of panties I felt extremely vulnerable and found myself
wondering what kind of mess would be incurred under this kind of attention.
Two fingers slid just inside me and I could feel the extreme moisture which
they met there. He raised those fingers to my mouth, and in my state of
arousal I did something I had never done before. I sucked on them and tasted
myself. Despite my bath, and great attention to cleanliness, due to my
arousal, the smell to me was extremely musky and heady, but the taste was
surprising in its sweetness and I was pleasantly surprised to find it not
unpalatable.

Although I would never had thought it would, this act increased my
excitement, which was no doubt the desired effect, and when S suggested
skipping supper and heading for his place, I did not offer any resistance.

A few minutes later we were there. I followed him into a quaintly decorated
room in a place accurately described as bohemian. The atmosphere was an odd
mixture of old tuscan style and new world minimalist.

We stood just beyond the threshold simply kissing, for the first time
tasting eachother, tentatively at first, but gradually warming in intensity.

My hands seemed to move of their own accord, exploring this new body, as his
did mine. More than once I shivered lightly with anticipation.

I moved away slightly and slowly removed my blouse, his eyes on me. I didn't
rush as I removed my bra and let it fall, but I made no move to remove my
skirt as it was the final item I had on. Without taking his eyes off me he
undressed and then undid my zip and let my skirt skide down my legs.

I felt exposed, but not uncomfortable, to my surprise.

He took me by the hand and lay me back across the bed where I expected he
would lay with me and kiss and caress me as we had been. Instead, he moved
to the foot of the bed and spread my legs. Down on his knees, he began to
lick my pussy, a very pleasurable sensation at first, but he was not gentle
in this and soon the pain overcame the pleasure. It took all of my
self-control not to grab his head in a vice between my legs and hit him over
the head, but I managed to ask him to be gentler and slow down, which he
tried to do, to his credit. For a moment I had feared that this was in fact
a psychopathic woman-hater who had lured me in with the sole intention of
biting my clit off, but in retrospect I realise it was probably partly his
love of pain (only when exacted on his nipples) and my indication that I
enjoyed certain types of pain without him knowing my threshold that lead to
this situation.

Following my pleas he did attempt to be gentler, but this roughness
underscored many of the night's activities. Fortunately, this did not ruin
things completely and much fun was had on both our parts (he has confirmed
this since, so it is not merely my wishful thinking for he does not seem to
be the type to say so just for the sake of politeness).

After some further attention to my nethers, he at last came up for air and
insisted that I cum, which I managed to do with some urging from his fingers
in my pussy.

Not wanting to leave him untended, I made a move towards him, but he held me
at arms' length and instead asked me to take out the toys which he had asked
me to bring with. I had included a few random items, from a small novelty
whip, to a set of leather cuffs, but the one item which I had packed
specifically for him was a set of metal nipple clamps. I had brought these
because he had indicated how much he enjoyed having his nipples twisted and
tweaked during sex.

As soon as he spotted these he asked me to apply them, which I did very
carefully. I had expected them to be too much for him as they were extremely
tight clamps, with tiny sharp teeth (something I am still convinced is a
manufacturing flaw), but he enjoyed them immensely, requiring very little
extra stimulus from me to bring him to orgasm.

A few moments later, when I would have been ready to continue playing, he
invited me to shower with him. We shared a fairly uneventful but pleasant
shower, and dressed as he indicated we should go for dinner. A little
astounded that he was content to leave it at that, I dressed and followed
him to a nearby restaurant where he ordered for us and we shared a tasty
meal, chatting about past experiences, life events, and general topics.
Still perplexed, I waited for him to indicate that dinner, and the evening,
were over, particularly as he looked quite tired and a little sleepy.

A crowd arrived boisterously then, among them a few obviously lesbian
couples. Having learned that I am somewhat interested in, though
inexperienced with, women, he began to encourage me to go and talk to them.

I laughed at the idea but then two of them came over and gave us shooters,
one of them being quite friendly with me. After a lot of encouragement I
decided to go up to the bar where they were congregated and ordered some
drinks for us. They took a while to arrive so I was able to listen in on
some of the conversation, and they began to include me. The friendliest one
was actually a straight, recently-divorced woman, so we ended up chatting a
bit, her askind a lot of questions about what I was doing there.

Eventually I lost my nerve and returned to our table, where S had appeared
to fall asleep. Once again, I thought, well that's the evening over. I
finished my drink, with him dozing, and finally I couldn't stand the sight
of one of the women wiggling her bum to the music and asked if we could
leave. I followed him back through to the room, and began to pack away my
belongings. He was stripping off, but I was sure that was just because of
the intense February heat and humidity.

After a few moments, he came over to me and started to kiss me. It was a
slow kiss, but not a goodbye kiss. His hands moved to my breasts, which he
massaged slowly before removing my top again.

Shortly afterwards we were again naked, lying on the bed. We kissed and
fondled eachother languidly, in no hurry, exploring bodies with our mouths
and hands. S began to lick and suck my clit again, inserting two fingers
into my pussy, finger-fucking me slowly. He found my little rough inner spot
and began to apply pressure. The pressure was a little too hard, and the
pain washed over me in spasms again, mingling with the pleasure. Given a
choice I would not have had it so rough, but he seemed intent on playing
that way. He gradually switched to merely finger-fucking my pussy, two
fingers, then three. I felt him apply lubricant, and felt the forceful
pressure as he tried to fit a fourth, screwing his hand around in me. I have
to admit that this was quite pleasurable, if sometimes a little
uncomfortable and he was only satisfied with his work once I had obtained
several orgasms. Finally, he withdrew and allowed me a few moments to catch
my breath. He had expressed an interest in having his arse played with
during intercourse, so I applied some lubricant and gently teased him with a
finger as he was prone on all fours. Standing behind him, my leverage was
good, and as he grew more excited by the play he started begging for more.
Without thinking, I picked up a large dildo, smothered it in lube, and
gently inserted it, only just in, then almost out, easing him into it. I
gradually increased speed and force, turning it slightly as I withdrew, then
leaned forward and started massaging his cock without stopping and it was
barely a minute before his body was convulsing with an orgasm any girl could
be proud of. I removed the toy as he collapsed and left him to recover for a
few minutes.

Fairly sure that this would definitely be it, I was rather surprised when he
suddenly came back for round three. I have to admit I have never received so
much oral sex in one night, nor have I played for that length of time
without ever experiencing penetration, but he was content not to go there,
so I did not make an issue of it. He administered more oral attention to my
pussy, and when I had cum again, I lay on the bed between his legs and
sucked him to an orgasm which proved too much for him as he almost instantly
fell asleep after that.

I helped myself to a very necessary shower, got dressed again, and woke him
to let me out.

All in all, it was a lot of fun, and certainly something different for the
books.

He was kind enough to send an email saying he'd had a good time and I might
hear from him sometime.

XXX