I first got introduced to toying with myself in my early teens (13).This was when I was beginning to play with myself, as most young teens do, finger wise, and then I found and used my mums vibrator on every occasion I could get!
I have already shared a couple of such times with you all on here.
The skills I learnt early on in my sexual development are the ones that I later found gave me the chance to enjoy myself with the men I have had in my life.
Much of my "schooling" in these early years came from videos I, and Tony watched together.Watching the actresses and the amateur wives on film toying with themselves. Such sights gave us great times and I learnt how to please myself, and the men in my life by watching and copying their "sexploits" on film.
Tony (my elder brother) especially liked to watch me bring myself off with either mums vibro or a bottle up me, his cock would get extra hard as he watched me intently and both he and I would often "multi cum" during these sessions...
He could spunk up two or three times in a lengthy sex session and I am able to "cum off" several times as well.
In particular I became very adept at balancing on the vibrator or bottle, in a squatting position. Often using some adhesive to make it stay in place, or having Tony or whoever I was "fucking around with" hold it in position.
This meant I could really "fuck it up me" deeply, by bouncing up and down on it, and at the same time manage to get my hands on Tony's cock or another of my boyfriends cocks to suck and wank it off, as he stood in front of me.
The result was always a massive cum for me. My fanny juice leaking down onto the bottle top and sides, or all over the length of the vibrator, and Tony always unloading a huge amount of his spunk into my mouth or onto my face.
We had fun like this for the years between me being 13 and 16 at home, then we continued our fun in Tony's new flat when he left home, when I was 16, and he was coming up to 20.
The privacy we had for those years meant we could spend a lot longer exploring and the sessions would sometimes be several hours long. Giving us time to really have fun and be less worried about being caught or exposed.
These sessions nearly always included watching videos and later DVDs, both of us getting turned on so much by not just our actions but by the sights and sounds accompanying us as we sucked, licked and toyed for ages.
The fun in his flat in these later years intensified, and that is another experience altogether!
As far as the toys are concerned, I had, by the age of 16 tried an array of vibrators, bottles, aerosol cans, hairbrushes, kitchen spoons, an assortment of handles for tools( screwdrivers, hammers etc), and of course had begun my love affair with fruit and veg.
I started off with the usual bananas and small carrots then obviously tried cucumbers, much smaller than the larger ones I was to later get so fond of...
The shape of these veg/fruits have always had me wondering if they have always been used as "natures sex toys" ... have women for thousands of years plunged them into their wet, eager cunts, having as much enjoyment as I get from fucking themselves with them?
Most of these things were small in size, to start with, compared to some of the later toys I would, and can use, my young cunt obviously just beginning its journey on my sexual life's path.
As well as the fairly regular fun we had, I was also introduced to how much it turns men on by watching women/girls play with themselves by:
A) Toying in front of and for other boyfriends of my own age I had at the time...
( I always carried on with Tony even when I was with every boyfriend/partner/one night fun guys until I was married to Mike).
I would be asked often to " fuck myself" with a toy or veg for many of my boyfriends whilst they watched and I willingly did so.
B) by the older lovers in my life: Mr R being someone whom I have already mentioned, the randy old Asian shopkeeper and of course Eric my first regular, senior partner.
It was definitely Eric who awoke my more kinky side. I guess you could say he was my mentor in many ways, and he was the one who introduced me to the larger toys and objects, and of course to having regular multi cocks to play with.
Eric was the one to increase the size of my own vibrators, taking great pleasure in seeing me use the larger ones to stretch myself open with and encouraging me to try and...
"take a little bit more length" ... and to... "fuck yourself a little harder Anna" ... with all of these dildos and vibrators on each occasion.
My young tight pussy was being "trained" to take ever increasing sizes of toys and objects, Eric delighting in "slutting" me up as he called it.
He regularly bought new ones for me to try, and he absolutely loved shopping with me for them in local adult sex stores etc. The thrill I guess, was of knowing that the shop attendants knew exactly what I was going to do with them, that I was going to be using this toy on myself for a much older mans pleasure, and Eric got excited very much at that thought.
(This is the very reason I love buying the veg, fruit etc, I use from the young shop workers in the local stores I frequent. Always dressing as provocatively as I can when doing so : short length skirts or mini skirts, high heels, see thru blouse or blouses with the buttons undone as much as I can get away with.Trying to get the young men's attention and get their cocks hard ... The younger they are the better!)
We would have regular sessions with me being encouraged to work myself up by starting off with a small toy, and then progress through the sizes until I was either plunging a huge toy or veg into myself, or either Eric or one of his friends was furiously fucking me with it.
I would end up shattered by the end of these sessions, and my young fanny was getting a regular and good pounding either from cock or toy.
I would often be "well gaping" or "stretched open" at the end of such sessions and Eric loved the sight of my cunt when it was "splayed wide and wet".
Eric's friends were also regularly invited to watch me "perform". This taking the form of me wanking, fingering and toying myself to many orgasms as they watched and then later as they all joined in on the fun. Most of these nights saw me red raw form the pounding I took and subsequently covered in cum from the guys.
More often than not my hole would have been filled by an assortment of vibrators, fingers, occasionally fists and of course wine bottles during a normal one of these nights fun.
After I had finished drinking my wine, as the guys drank their whiskys and beers, the anticipation in me would build up as I knew what the the outcome of the evening would be. I knew that the bottle I had finished would soon be up me and I again participated eagerly for their and my pleasure.