This story is for 'Squeeze Girl' who wrote about her Private Anal Pleasures on May 24th on SoloTouch. She asked about other girls who enjoy anal fun.
A quick note about myself. My name is Lee, I'm in my 40's as well, married, and a big beautiful woman. I have long, curly black hair, green eyes, and am proud of my ample DD cup breasts.
My first encounter with anal sex occurred when I was fourteen. I had been playing with myself for several years, but always hid it well, and felt guilty afterwards. Growing up I heard my mother rant about 'those sex perverts' and had the notion that 'good girls don't do that' and 'sex is nasty'. So it's no wonder I grew up with a guilt complex.
Anyway, I was in the hospital for something, and had to have several enemas. The nurse who gave them to me would come in, and rub my naked ass to 'calm' me. She would then lube her finger, and rub it in a circle on my anus. Despite the fact I was sick, I was surprised to find myself getting aroused. I found myself actually enjoying the feeling of the nozzle sliding up my ass. Afterwards, when I was really kinky I would rub my anus with one hand while doing my pussy with the other. While I'd have a great cum, I always felt guilty afterwards.
My life and attitudes changed during my senior year in high school. My dad got a job working for a company where he had to travel, working out of town for months at a time. I convinced them I was old enough to take care of myself (I'd be turning 18 in October) so off they went. It's kind of amusing now, but at the time I was even too shy to get naked and masturbate while the sun was still up. I actually waited until the sun went down before I decided it was OK to pleasure myself.
It was an odd time, I would spend my evenings naked, masturbating. I even went so far as to use things like carrots and cucumbers up my pussy and ass. The morning after a good ass reaming I would feel really guilty, and swear never to do it again, and not touch myself for several days. Inevitably I'd return to it.
My attitudes received a needed overhaul when Helen moved into the neighborhood, a few houses down from me. Helen was a divorcee in her early 40's. Like me she was on the chunky side, with short greying hair. Maybe it was just because Helen and I both lived alone, but for whatever reason we became good friends. As time passed we became open with each other, talking about anything and everything, including sex. Helen was also not shy, she had no problems changing clothes in front of me, letting me see her in her undies or even naked.
Helen taught me a lot, but the thing she really drilled into me was that sex, and hence masturbation, is not 'dirty', that good girls DO do it, and that anything you do to yourself or with another consenting adult is perfectly OK.
It all started one November Friday evening. I had walked down to her house, and was visiting when it started raining. Really pouring. Helen invited me to spend the night, offering to have a fun 'pyjama party'. I accepted, and we continued to talk and chat. As the evening went on, Helen said it was time for the pyjamas, let's go get comfy.
Once in the bedroom she stripped down, and told me to do the same. She began rummaging in the drawers, going 'no, no...not them...' Finally she turned to me, and said the hell with it, we both sleep naked, might as well be comfortable. She told me to lose the panties (the only thing I still had on) and let's go back to the living room. I was a little nervous, but Helen had seen me nude before while watching me dress, so I tossed my panties aside and followed her out.
We sat on her sofa, talking about all sorts of stuff, eventually turning to sex and masturbation. I wound up confessing to her my attitudes, and even my anal sex guilt/pleasure issues. She held me as I cried, assuring me I was not a 'bad girl' and explained that whatever I did was OK. I wasn't hurting anyone, I enjoyed it, so why feel guilty?
The speech made me feel better, but it didn't convince me, and I think Helen could tell. It was then that she did something I will be eternally grateful for. She showed me how to be guilt free.
Taking me to the bathroom, she got out her enema bag. The whole time she was talking, saying how much she enjoyed it, how sexy it was, how great she felt, and so on. She took me into the shower and slid the lubed tip up her backside. While it was there she was rubbing her pussy, talking the entire time saying positive things about how wonderful it was she could enjoy herself that way.
She came noisily, moaning and groaning. When she stopped shaking, she told me how great that was, and thanked me for sharing the experience. I was shocked at how she was able to enjoy herself so openly and guilt free in front of me, but aroused at the same time. I knew I wanted to be just like her.
Helen pulled the enema nozzle out, and said 'your turn!' She spun me around and pushed me over, and began massaging my ass, then my anus. I was so turned on, I never stopped to think about what I was doing, I was just living the experience. After a few minutes of fingering me, Helen slid the nozzle inside me then pulled me up and told me to play with my pussy.
I did, with her standing beside me, saying soothing, encouraging, sexy things the entire time. It didn't take long before I came extremely hard, so hard my pussy actually gushed! Helen pulled the nozzle out, talking the entire time. Her words made me feel good, as she spoke of the wonderfulness of our bodies, how great it was we could give ourselves that much pleasure.
After showering we went to her king-sized bed, where she got out her toys. She demonstrated, then let me use many of her sex goodies, including vibrators, dildos, and butt plugs. We masturbated many, many times that weekend, using toys in all of our holes. She got me to admit, verbally, out loud, that I did indeed enjoy masturbation, that I did indeed enjoy having things up my ass. It was incredibly powerful, to hear myself, my own voice admit my deeply held, inner most passions.
Over the rest of the winter and into the spring we grew close. Helen taught me many more sexual techniques for self pleasure, and we explored our bodies in a lot of different ways. She taught me to really enjoy the taste of my own pussy, a taste I enjoy to this day. She showed me how to masturbate in different positions. On my knees, back, doggy style, face down, face up, standing, squatting, any way we could think of.
We had always been huggers, holding each other after a good cum, but one day I just leaned over and gave her a passionate kiss. After that it became normal for us to greet with a hello kiss, and give a kiss upon departing.
We also, after months of my begging, finally had a weekend of full blown girl girl sex. Helen had always been cautious, limiting our sessions to mutual masturbation with limited touching. Mostly just hugs, although I did enjoy a good hug with our breasts and plump bellies mashing against each other. Finally after months of my asking, we spent the weekend using dildos on the other, and doing whatever else we could think of.
Shortly after this Helen, in her wisdom, told me I had 'graduated', and that she felt I was ready for a life of guilt free masturbating. She said I needed to start dating boys again and be with kids more my own age. At the time I was hurt, but in retrospect she was right. I think she sensed I was becoming too emotionally attached to her, and that I needed someone more my own age to last me into the future.
I will forever love Helen, for the gift she has given me. She not only told me, but showed me that it was perfectly OK for a woman (or a guy I guess) to bring themselves pleasure, or to have any kind of pleasure with another consenting adult. After that I was able to masturbate, day or night, using all of my body holes, guilt free. To this day I happily enjoy stimulation in my pussy and ass.
Helen was right too, I eventually found a nice guy and settled down. He was a bit straight laced to start with, but I was able to bring him out of his shell. but as this has got too long, I'll make that another story.
I last saw Helen back in 1990, I had returned home for a visit. I slipped away from my family to walk down to her house, and as usual we greeted each other with a warm hug and kiss. I was distraught to see all the boxes, and found Helen had retired and decided to move to Ohio to be closer to her grandkids. I was grateful for the chance to tell her one last time what a difference she had made in my life, how she had opened up a world of pleasure to me.
Helen, if you happen to see this, you know that I'll always have a special love for you.