Where Do I Turn Now?

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Middle-aged woman confronts her "tendencies".
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fessee
fessee
4 Followers

From when I was young, I was always aware I was different. When I was a teenager, I and several girl friends located the stash where my brother kept his Penthouse magazines. While they looked at the nudes and thought how boys would be turned on if only they looked like that, I was turned on just by looking at the nude women.

Many years later, I was at an international business conference on a Greek island. Like most European conferences, this one had meetings morning and evening with the afternoons free. The beaches were extremely inviting, and as usual in Europe, topless. I, as well as many of the women attending spent the afternoons on those beaches, amusing ourselves chuckling over the Americans, the only ones too shy to shed their tops. After dealing with business on the first day, I met a Swedish woman, and we shared drinks that evening in the bar. Over the few days we were there, we talked about ourselves, my marriage (happy and sexually very fulfilling) and her quite uninhibited sex life back home.

On Thursday afternoon, after time at the beach, I returned to the dressing rooms to shower, and change back into clothing suitable for dinner. I stepped out of the shower, completely naked, and ran headlong into my Swedish friend. She took my shoulders in her hands and came toward me for what I though would be the Euro two-cheek kiss. Instead I found her lips directly on mine, her body pressing against me. Every woman knows and understands a kiss that is just an instant too long, one that carries with it an invitation. I was so startled that I didn't react.

Her eyes looked directly into mine, and she held me more tightly, and again our lips met. This time her tongue swiped across my lips, and still in a daze, mine responded. I was really aware of only one thing however, and that was the press of her bare breasts and particularly her stiff nipples against my chest. I have hugged many women, have kissed many, but never before had I felt nipples against my own bare breasts. It electrified me, my knees were weak, and I distinctly recall feeling the familiar tingle between my legs. I pulled away. I was scared, both of her, and more particularly, of myself. I almost ran to where my clothes were, and got out of there as fast as I could. I tried to forget what had happened, but couldn't, and that night, in bed, my fingers quickly found a warm, wet place, that felt very good indeed. Were these "proper" feelings? I thought not.

A few days later, I was back at home, and cuddling with my husband. We are very open with each other, and I told him exactly what had happened, including my reaction, and admitted to him that the invitation was there. To my astonishment, he replied "so why didn't you go for it? You've always had a thing for women, we've talked about it enough, why did you chicken out?" Goodness, even my husband knows I have these strange feelings.

On an internet meeting place, I had become friends with a woman 20 years my junior, named "Amy". She was into spanking, admitting early on that it was her favorite masturbation fantasy. My husband and I have a wonderful sexual relationship with a fair amount of role-play, dom/sub, and spanking. Amy was just beginning a relationship and I was able to give her a lot of hints and ideas as to how she could develop the same kind of fun and games with her new boyfriend.

Over the course of several months, and protected by the aliases and unknown locations of the internet, we became more and more uninhibited in the things we did and said. I learned everything of her new relationship with Jack including (for her) the magical first time she had gone over his knees with her panties at half mast. You could say I tutored her in ways to manipulate her man sexually, and she got all A's in the course. I actually gave her a how-to on oral sex, something that remarkably enough she had never done at age 28.

As we went on growing in our anonymous, but intimate friendship, we progressed to little "challenges" as we called them. You must get your husband/boyfriend to kiss your toes. You must masturbate in bed without waking him up. No panties under a miniskirt. Wake him up with a blow job. Get him over your knees and give him a spanking. In each case, if one of us succeeded and the other did not, a penalty was inflicted. There were bets too, mostly on sporting events, and the loser would have to tell the husband/boyfriend that they had a bet to pay off, strip to panties and bra, and perform oral sex. Believe me, our men, never complained! Finally, a bet on the Super Bowl required the loser having to ask her husband/boyfriend for anal intercourse.

As the relationship continued, more and more I was the older woman giving advice and how-to's to the young one. I became her "auntie", threatening her more than once with a spanking for her bad behavior. In fact, once when she had admitted drinking too much, flirting with a guy, and doing some heavy necking, I "made" her ask her boyfriend for a good hard spanking – which she did. And got. And enjoyed. In fact, it became apparent very quickly that Amy liked hard spankings, just with the hand applied to the bare bottom, but nonetheless much more than just a few lovetaps.

We had no secrets, we talked about our sex lives, including some of the domme things I do with my husband. We also discussed masturbation and discovered among other things that it is something we both do quite often, and that we both have favorite fantasies – "old reliables" as we called them. Hers revolved about school scenes, where she is caught doing something naughty, usually with a boy, and must report to the headmistress for punishment.

Throughout the eight or ten months of correspondence, we never revealed anything more about ourselves than our aliases; we had no idea of where either of us lived, only that I was a 48 year old mother of two grown children, and she was a 28 year old nurse, going out with a doctor. I knew she was small and slim, she knew I was taller, middle aged, and gravity had already set in.

Then one day that I mentioned I wouldn't be writing for a few days, because I was to attend another business conference, this time in San Diego. Immediately I got a response saying she lived only about 30 miles from there, and suggesting we meet for "drinks, dinner, and whatever". Wow! Now what?

I went to my husband and reminded him of the conversation about the Swedish lady and asked him if he thought I should risk meeting this "Amy". Although he teased me terribly about what might happen, he said "sure, why not?" After some further to-ing and fro-ing, we agreed to meet in my hotel room at 4 pm on the Friday afternoon after the conclusion of the conference. In an aside, she asked that I bring with me not only the paddle I use regularly on my husband, but also some of my domme clothes since in the small town she lives in, none of these are available. My husband even suggested I bring a deck of cards in case we wanted to play strip poker!

I arrived in San Diego and attended the conference from Mon-Fri. On Friday, I was late getting back from lunch, and so nearing 4 o'clock I was still dressed in business attire, a two piece suit, creamy blouse, nylons and no-nonsense heels. At exactly 4 pm came a knock at the door. I opened it, and my heart did a little flip-flop and I felt a stirring between my legs.

Amy turned out to be tiny, very slim, very pretty, and with shiny black hair pulled back in a pony tail. But that was not what caught my attention. She wore a plain white blouse, buttoned right up to the neck, a plaid kilt which ended at mid thigh, dark blue knee sox, and tennis shoes. In keeping with that, she wore no makeup of any kind. She was dressed as a schoolgirl, and a penitent schoolgirl at that. She was in her fantasy role. She never once looked up. With eyes cast down, she handed me a letter and said Mr Jameson (who?) said she was to hand it to me. I read the letter.

It said that Amy had been found in the boy's bathroom, hiding in a stall where she could peep out at the boys at the urinals. It recommended she be expelled immediately, or if not, that she be punished severely. I might add that the letter from "Mr Jameson" was written in a dainty, feminine hand.

I ordered her in, and asked if this was true. She seemed near tears as she admitted that it was in fact true, and when I asked her why she would do such a thing, she replied that she liked to see "little boy's wee-wees". I took on the role of the dominant headmistress easily. I berated her for what she had done, and informed her expulsion was the only answer. She of course pleaded to be spared the humiliation of expulsion, and I explained the only alternative would be severe punishment. I explained that she could expect a spanking of 100 smacks, the maximum naughty girls could receive in our school. I also pointed out that while only boys could be paddled, since she had been caught in the boy's bathroom and was peeking at boys, she would be treated to a session with the paddle as well.

For the first time she looked up, and I could feel her eyes roam up and down my body. "Please Ms Fessee" she said, "I won't do it again." But the idea of severely spanking her was already exciting me. My "tendencies": was spanking a woman sexually arousing me? The answer was scaring me. The answer was yes.

I removed my jacket, and rolled up my sleeves. I sat on the corner of the bed, hitching my skirt well up my thighs, and said "get over here, young lady!" When she got to me, I ordered her to lift her skirt up to her waist. She did and revealed in keeping with her schoolgirl role, baggy white cotton underpants. By the time she was across my knees, I could feel moisture in my panties. I ordered her to lift up, and I pulled the underpants down to her knees.

Her bottom was exquisite. Olive colored, perfectly round, with two dimples at the top of her cheeks. I continued to tell her how bad she was and began the spanking. Alternating cheeks, waiting several seconds each time to allow the sting to build up, and delivering each stroke with a sharp wrist snap. Within ten spanks she was squirming, and by twenty moans were heard. And then miraculously, little Amy transformed from a role playing little girl to a woman becoming sexually excited. As the spanking went on, she began alternately pressing her body into my lap and raising her bottom to await the next stroke. I became aware that her leg movements were calculated to raise my skirt higher up my thighs. Finally she began to grind her pussy against my leg.

The one hundred spanks flew past, her bottom coloring to a deep red from her dimples down to that most sensitive place, where the thighs and bottom meet in a deep crease. Tears flowed. Little goose flesh stood out across her bottom, and here and there were darker spots which would undoubtedly become small bruises. It was obvious when I finished that she was highly aroused, and I told her to go and stand in the corner with her skirt held high and those underpants down round her ankles. I opened my suitcase, removing the leather paddle that is one of my favorite toys. I looked at her bottom, beautifully colored, and noted that she had furtively moved one hand down to touch herself. I must admit that I also slipped a hand down the front of my skirt, and checked the humidity. It was nearing steam.

I pointed out that she still had a paddling to endure, and that it would be the highest severity level boys could receive, twenty on the bare bottom. I knew she would really feel it when I paddled her. And I knew something else as well. It was decision time. My husband had said "go for it". and Amy was clearly in a highly excited state. For many years I had wondered about my own tendencies, I had been inflamed by my Swedish friend, and now my future sex life stood half way across the room displaying her reddened bottom and rubbing her pussy.

I went for it.

Very calmly, I unzipped and removed my skirt, hanging it up neatly. I did the same with my blouse. I considered the pumps and stay-up stockings but decided to leave them on. I had on a matching sky blue lacy panty and bra set, and before continuing with Amy I took a quick look in the mirror. I liked what I saw. I ordered her to step out of those ugly underpants and to come over. When she turned round and saw me, her eyes lit up, and I noticed her tongue slide back and forth across her lips. At that moment, she was every woman I had ever fantasized about. As she approached, she made no effort to lower her skirt. She was showing me her pussy; she knew it, I knew it, and dammit, I was enjoying the show very much.

I bent her over the end of the bed, lifted her skirt onto her back, and tapping the inside of her thighs indicated I wanted them open. When her pussy was clearly in view, I took the leather paddle and said simply, "count them". We were no longer playing ittle schoolgirl/headmistress roles, we were two highly aroused women playing out a domme/sub game.

I paddled her slowly and hard, five at a time. With each stroke, a leg kicked out, and sobs were released. However, after about a dozen, it was hard to say if the sounds I was hearing were moans of pain or groans of pleasure. After each five, my hand roamed over her bottom, ostensibly warning little Amy about her bad behavior, but really to ensure she would be able to take the full twenty. I also loved the feel of her soft, and very hot, bottom. Once I allowed a finger to touch her backdoor, and was rewarded with a soft groan. This time there was no doubt it was from pleasure. Glancing down, I could see the glistening moisture on her pussy lips, but not waiting to spoil what was to come, I did not touch her there.

When she sobbed "twenty, thank you Ms Fessee" I shoved her onto the bed on her tummy, full length and still sobbing. I quickly retrieved a jar of cold cream from the bathroom, sat beside her on the bed, and put a large gob on each cheek. And began to rub it in. And became more and more aware that my own panties were now soaking wet. I leaned down and kissed her cheeks. My hand slid down her crack, and without saying a word, she spread her legs.

My fingers slipped into her pussy, and for the first time in my life, I felt another woman's wetness. She responded with groans to every touch while my fingers explored her lips, her opening, and then the nubbin of her clit. In only a minute or so, and again without saying a word, she flipped over onto her back, her skirt at her waist, and her legs splayed open. This time I would not be the chicken I had been on the Greek Island.

I laid down between her legs, and began to kiss the insides of her thighs, moving slowly higher and higher. She had a thick black bush, more hair than I had ever seen on a woman, and around the opening it was already glistening and noticeably wet. I kissed upwards toward the top of her legs, and the thought went through my mind of all the dead fish jokes about the smell – in my life I have only ever smelled my own. Her perfume was becoming stronger and I found it simply irresistible.

Finally I planted a kiss, right on her lips. Then another. I ran my hand over her bush, and was startled to find how soft and fleecy it was, compared to my own. With two fingers, I opened her wide. I had never thought about this, but many more men than women have seen a pussy from up close. My fingers traced her outer and inner labia, and I found her to be softer and more velvety than my own middle aged sex. I was surprised at how small her clit was, again I have no experience except my own. The visual images of her pussy will be with me for the rest of my life.

Seemingly without my even thinking about it, my tongue slid up and down her lips, then penetrated just a little and explored. Of course I knew everything I would find, what woman doesn't? But the excitement of feeling, smelling, and tasting another woman, of feeling the velvety lips with my tongue, experiencing the perfume, and then tasting her feminine juices – it was all so new, and so terribly exciting. My tongue found her clit and I tried to reproduce the things my husband does to excite me. Gently flicking it left to right, right to left, then up and down, and up and down.

When I knew she was close to climax, I stopped what I was doing and heard "f'rChrissake, don't stop now". I began what he calls the "long, slow" that always takes me over the top. With the lips spread wide, the flat of the tongue (not the tip) is placed over the opening and then moved upward very, very slowly. In this way you can know exactly when it is going to get to the clit and anticipation helps build the emotions. On arrival, it moves so slowly that there is a long time (seconds!) of constant stimulation, ended by a little flick with just the tip. Enough to do it to me, and enough to do it to her too.

A half hour later, with the help of her schoolgirl backpack, we dressed in normal casual clothes and went out. We had our drinks, and our dinner. After dessert, I asked he how she was going to get home – thirty miles away. She looked at me, smiled, and said, "I'm not going home. I'm spending the night with you."

Completely in a daze, we returned to my room, and she said simply "I want to see you naked. Take your clothes off." And I did, feeling more naked than I have felt before with men. She had me turn slowly in front of her. She remarked on my shaved pussy, my breasts – much larger than hers even if sagging these days – then had me turn and bend over. Frankly, I expected to feel the paddle across my bottom but instead of hard leather, it was her soft and delicate fingers stroking between my legs.

I started to say something, but she simply said "hush!" Her finger found my clit, and I started to flow again. She paused and said "don't move". I heard, rather than saw, her strip off her clothes. She called me to the bed, and we got on top of it, naked. Our bodies found each other, and our lips found each other, and then our lips found each other's other lips, and we made love. Over and over.

I no longer wonder about being "different". Or what my "tendencies" mean. I no longer wonder if I can be turned on by a woman. I no longer wonder if I am bisexual. I know the answer. Yes, I am. But, where do I turn now?

fessee
fessee
4 Followers
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