I hope you enjoy reading this story as much as I did writing it! Many orgasms were spent producing the various parts of the tale. I sincerely hopy you can't get through it without taking matters into your own hands!
Good or bad, please vote. Feedback, either anonymous or not is, as always, very appreciated. Everyone who appears in the story is a legal adult.
"May I sit here?" I looked up, somewhat surprised to see Debra standing at my booth in the deli where I had stopped for lunch.
I had met Debra through her best friend from childhood, Lisa. Lisa and I had been lovers for several months after I had met her when I had stopped to play the knight in shining armor, by offering her some assistance one fine day when she was stranded on the highway due to car trouble. I had thought it would be a few minutes of goodwill invested helping a beautiful (she was!) damsel in distress, and perhaps getting her phone number in the process, or if not, still getting to feel good about having helped out, and then I'd be on my way. As it had turned out, I had ended up spending most of the rest of the afternoon driving her hither and yon getting multiple problems solved and so, once finished she took me out for dinner and drinks. From there we ended up in her bed, not that I had been even slightly averse to that ending!
After that, we were together practically every evening and slept together nearly every night, either at her place or at mine. Since we were together so much it was natural that I would meet her friends and vice versa. So of course I had met Debra and her boyfriend George early on. We had partied together, gone clubbing together, played cards and other games, and watched sports on TV in the evenings or on weekends in each others' homes. We had even spent a couple of weekends at the beach and a couple more camping together. George and I had become pretty good friends and had spent some time doing guy things, like puttering in my shop and hunting together, too.
But Debra and I had really hit it off. When we went out to a club, George and Lisa would dance together because Debra and I both would be ready to dispense with the dancing fairly quickly while neither of them ever could get enough. So Debra and I would stay at the table and talk while George and Lisa danced. We never ran out of things to talk about, either. She was intelligent, well read, funny, and fun to be with.
I knew Debra recognized the attraction, too, but even though there was often quite a bit of sexual innuendo and many double entendres we never did anything about it. You just don't hit on your girlfriend's best friend or, in Debra's case, on your best friend's boyfriend. Not if you have any class at all and Debra is a total class act. Except that it isn't an act. She was just naturally classy.
She is a redhead, too, even her eyebrows and eyelashes, though they were paler, more like strawberry blonde often with a slightly greenish cast, kind of like the copper was getting a patina. She had very deep green eyes. Some of the innuendo had even run to teasing about whether the hair was red elsewhere. (George had privately assured me that it most definitely was, though Debra had only left it to imagination, never even hinting one way or the other, only saying "wouldn't you just like to find out?") Besides, now George had become a very good friend of mine and Debra was his woman so that was that.
But, still, even when we were all riding somewhere together Debra and I would find ourselves talking mostly to each other while Lisa and George spent most of their time talking with each other.
While Lisa, who was a brunette, was quite beautiful, Debra was a stunner. I should admit right now that I'm an ass man. Lisa's was gorgeous but Debra's was a walking wet dream. Yeah, I was attracted to her. Both women had nice sized breasts, not huge, not tiny. Lisa's were a bit bigger, Debra's a bit firmer and higher. Being an ass man, I don't care much about breast size, though I do prefer that they not be so big they are in the way and I don't particularly want them to be flat, though I have a more relaxed definition of what constitutes flat breasts than many men. I don't mind itty bitty titties at all. Shape is much more important to me; I like 'em fairly firm, not baggy. But I'm still an ass man, thorough and through. Show me a really nice ass and I'll probably never notice the breasts.
Anyway, I liked to look at both women. But in truth Debra and I had more in common than Lisa and I did.
Lisa had encouraged Debra and me to dance together on several different occasions and we had actually given in once and danced a couple of dances. The second one was a slow number and we had fit together perfectly. When it ended we were just about to kiss without even being conscious of it. After that we had declined to dance together again, fearing what might come of it. Both Debra and I knew without it ever being said that under other circumstances we would fall into the nearest available bed together without even the need for discussion.
I was head over heels in love with her, and I know the feeling was mutual. Oh, well.
Hey! Question? Why is it head over heels? Shouldn't it be heels over head? As in; upside down? Well, she probably wasn't any good in bed anyway. Sure, Right! Sour grapes. I admit that I fantasized about her. So what? Do you ever fantasize about someone who isn't your partner? So you mind your own fantasies and I'll mind mine.
As time went on Lisa and I began to have some issues. I'm not very inhibited sexually, while Lisa was very much so. To begin with, only once did I see her nude with the lights on. Oh, I got to see her body regularly, but only because I have excellent night vision and neither of our bedrooms were completely dark at night. Since I am very visually oriented I always wanted to turn on the lights or make love in the daytime but Lisa wouldn't hear of it. We only showered together once, slightly tipsy and in total darkness, though I suggested it many, many other times. But Lisa always locked the bathroom door. I never do and seldom even closed it when we were alone. She never came in, though.
Further, at the risk of being overly blunt, I really, really like to eat pussy. In fact, I like it so much it could almost be a fetish. Well, Lisa wasn't really comfortable with it. She didn't want me to do it unless she had a couple of drinks in her. But she always came like gangbusters whenever I went down on her. I had also tried to coax her into letting me clean her up after sex a few times, ala creampie, but that was totally out of the question. She said it was too nasty. "Why would ANYONE want to do that?" From that you might guess that a blowjob was also out of the question. She would kiss it but would not take it in her mouth under any circumstances, even when she was thoroughly drunk.
Anal sex? "Filthy." Vibrators or dildos? "Unnatural." Bondage? "What is wrong with you?" And my personal favorite kink, spanking. Now you might think that an ass man would love to spank a pretty hiney and you'd be absolutely right. But even more, I like to be turned over a soft lap and get my own tail reddened. Or over the arm of a chair or couch, or the edge of the bed, or a pile of pillows, or a table; well, you get the idea! It turns me on in a way that nothing else quite does. When I get well spanked my nipples, which are normally just something to keep my chest from being boring, become very sensitive. The nerves somehow connect directly to my dick and almost my whole body becomes one big erogenous zone. I guess I have deep psychological issues. But they are generally fun psychological issues so why should I worry about them?
So of course I worked a bit harder on the spanking thing with Lisa. My birthday conveniently came up about six weeks after we got together. Lisa threw a really good party. But when I tried to get her to give me a playful birthday spanking she declined saying, "That is for kids! Grow up!" She wouldn't play even when I told her it would be fun. I had tried a couple more times slapping at her bare bottom trying to get her to slap back but, no dice. Needless to say, when her birthday came a few months later, she flat out refused to consider a birthday spanking, even fully clothed. But she was well aware of my spanking proclivities. It is the one thing I never gave up on, mentioning it often, one way or another, sometimes subtly, often not.
But she did like sex and there was plenty of it, just that it was all vanilla, nearly all missionary position, and I only got to dive the muff when she had at least a couple of drinks in her. Even though I was frustrated, the sex was still good as far as it went. It just didn't go far enough. So I was becoming increasingly restless, noticing flirting from other women more and more as time went on and responding to it more and more, even looking for opportunities to initiate a flirt myself.
Then one Tuesday evening when we had planned on sleeping at my place, Lisa got there nearly an hour ahead of me. When I arrived I walked into the bedroom to find her sitting on the bed with my "toy box" sitting next to her and the sex toys it contained spread over the bed. This "toy box" normally lived with several other similar, but much more innocent boxes on a high shelf in the walk in closet in my bedroom, not hidden, but not labeled and not casually reachable either. A stool was required to get any of them down. The folding stool was, of course, standing in the closet when I got home, having been moved from its usual position folded up behind the spare bedroom door. I had mentioned in passing during times when I was trying to get her to spank or play other games that I had toys, but never where they were kept since she had never expressed any interest.
"What is all this?" She asked in a quiet voice.
"Sex toys." I replied. "They haven't been out in months so I'm wondering how they got on the bed."
"I guess I got curious. Why do you have them?"
"Well, they are fun to play with once in a while."
"Oh." A long pause. "What about these? They don't seem to be sex toys." She waved to a pile of wooden kitchen utensils, rulers, a large paint stirrer, ping pong paddle and several other items that made decent paddles.
"Paddles. I've told you I like spanking. The leather stuff is also for spanking." I indicated a cat o'nine tails, a tawse, a leather belt, and a couple of other leather floggers and slappers, many of them homemade. I hesitated, decided to be blunt. "If I'm doing a self spanking, I generally use the wooden stuff because the leather is hard to control, but if someone else is doing it I really like the leather stuff."
"Oh." She picked up a length of silky smooth braided white nylon rope and a pair of handcuffs and held them up and raised her eyebrows.
"For bondage. It is fun to be tied up and helpless while someone you trust pleasures you. It is also fun to tie someone else up and pleasure their helpless body. There is a blindfold somewhere in there too."
She just said "Oh" again. Then; "I guess I know what these are for." Indicating a couple of butt plugs, some realistic dildos in various sizes, a waterproof vibrating wand with an egg shaped end, a string of anal beads, an ordinary bullet shaped vibrator, and a pair of douche/enema/hot water bottle sets.
I didn't say anything.
"Do you really put these inside you?" holding up the larger butt plug.
"Sometimes..., not in a long time now, though. I doubt I could get that one in right now. It's been too long and it is pretty big."
"Is there someone else?"
"Then what about these?" She held up a black garter belt, bra, panties, and stockings.
"Oh. An old girlfriend who moved away gave them to me a few years ago after she dressed me up in them a couple of times."
"Why do you keep them?"
"It was fun. I looked really silly, but it was still fun to kind of slip into a woman's clothing, body, uh, you know... psyche."
"So, I guess these go with the outfit?" She held up a couple of strap on harnesses, both with dildos mounted. "You want to be a woman?"
"Nope. I like being a man. But I think everyone gets curious now and then as to how the other side feels. Besides, it was just plain fun. Recreational sex doesn't have to be the same old boring stuff, you know."
I realized as soon as I said it that it was a mistake.
"Boring! Is that how you think of our sex life?"
"Of course not! But there is absolutely nothing wrong with expanding the play to include other possibilities."
"You think sex is play?"
"Wellllll..., yeah. Don't you? After all, we aren't trying to make a baby. What else would you call it?"
"I guess if you look at it that way..."
"Well how else would you look at it? It's fun, it makes you feel good, it is relaxing and enjoyable." Play! Is there a different word that fits better?"
"That just specifies what kind of play it is. Play is the broader term that takes in recreational stuff like games, sports, and, of course, sex; Things that relax the mind and work the body."
"Um..." she sat there, frowning, obviously considering it. Finally she dropped the lingerie back into the box. "I need to think about this. Would you put this stuff back up? I'll go start supper while you do that and get your shower."
"Uh, OK." I watched her leave the room and let out a long breath as I heard her enter the kitchen. I started tossing stuff back into the toy box at random. Usually I try to organize it at least a little, but not this time. I just quickly loaded it up, put it back up on the shelf and put the stool away. I took a quick shower, dressed, and joined her in the kitchen. She is a pretty good cook but I do not recall to this day what we had that evening. We sat at the table and both made some effort to discuss unimportant minutiae relating to the day's work. Then we cleared the table, did the dishes and retired to the living room to watch a previously recorded program. When it was over she reached across me, picked up the remote, flipped the TV off, and said, "Bed time?"
She was a wildcat in bed that night. To begin with she left one of the gooseneck reading lamps that are clamped on the head of the bed turned on. She did turn it around to where most of the light was blocked because it was very close to and facing the wall, but it was on! She undressed and spun around, giving me a good look at her nude body, before crawling up on the bed. I stripped quickly and joined her, taking her in my arms and kissing her thoroughly while running my hands all over her body. When the kiss broke I raised myself up and feasted my eyes on her luscious body. She spread her legs wide and said "I know what you want to do. Go ahead." She let me go down on her despite not having drunk anything stronger than iced tea. After a thundering orgasm she said "Do that again!" so I did.
And again! I was in heaven. Then she pulled me up and guided me into her. She was sopping wet. As soon as I was buried to the hilt, she rolled me off her and continued to roll until she was on top, then she sat up, all without letting my cock escape from her clasping pussy. I can last a long time in this position so she rode me to a couple more massive orgasms. Then she rolled us back over, locked her legs around me and said, "Fuck me! Hard!" She had never, ever used this word within my hearing before this. So I did fuck her hard and this time we both had huge simultaneous orgasms, gasping, moaning, and screaming in ecstasy.
I collapsed on top of her, reached down and pushed one of her legs down, took her in my arms and rolled to the side, my rapidly softening cock managing to stay planted in her pussy as she rolled to where she was half on top of me and half on the bed. I pulled her other leg back up across me so I wouldn't slip out of her and she reached up and turned off the light before we both fell asleep, me with a hand cupping her soft bottom. I remember thinking just as sleep overcame me that I should have showed her the toy box long ago.
Lisa was not in the bed when I awoke the next morning, but I could hear the sounds and smell the smells of breakfast being prepared. I brushed my teeth, splashed water on my face, slipped on a robe, ran my fingers through my hair, and went to the kitchen. She was fully dressed for work and was just slipping the plates onto the table. "I was just getting ready to come get you." She said. "Don't want to be late for work." Nothing was said about the previous evening until we had cleared the table and started the dishwasher. Then she said, "Sit. We need to talk" as she pulled out a chair. I turned one around and sat leaning my arms on the chair's back, facing her.
She sat there looking at me then, finally, opened her mouth to speak. "Uh, I don't know how to say this very well, but uh, I don't think we are very compatible sexually."
"Huh?" I was thunderstruck. This wasn't what I was expecting at all in view of last night's romp in the bed.
"Well, I kind of knew that you were into some kinky things; you've hinted enough, but after seeing all that stuff, I realized that there was no way I was going to be able to have anything to do with it. It is perverted. You're perverted, I think. For me sex isn't a game to be played different ways. It just isn't." She stood. "I've already moved all my stuff to my car. I'll gather together all your stuff that is at my apartment and get it to you by the weekend. Here is your key." She laid the key on the table. "I've already gotten mine off your ring. I'm sorry it didn't work out. Bye." And she left. Just like that. I had not even uttered a single intelligent word.
Presently I remembered that I was going to be late for work so I called in and left a message that I'd be late, I had some personal business come up. That was no lie but it sure was an understatement! I slumped back down, despondent, and ran it over through my head. I must be dumb, because I sure didn't get it. She had been less inhibited than I'd ever seen her last night and now, THIS?
That evening after I got home from an interminable day at work, I found a message from Lisa on the answering machine advising me that she had gathered all my stuff and that she was going out of town very early Saturday morning but she would put the box on her patio before she left. I was also told that I should not try to pick it up before she left. Since there was nothing that I would need before then at her place, it was no big problem, though I would have liked to see her, even though I knew it would be pointless.
I nursed my bruised ego for a couple of days before deciding that she was absolutely right, we were not sexually compatible and this would have happened sooner or later. Probably not much later, I admitted to myself in a moment of honesty. After all, I had already begun to actively and seriously flirt with other women before this happened. She had just taken the step firt. Too bad that the last night hadn't been a portent of better things to come, but since it hadn't, there was no use crying over spilt milk.
A friend of mine, Will, called the next evening and asked if he could borrow my pickup truck on Saturday after lunch because he had bought a mechanic's toolbox that was too big to fit in his car and he needed to get it home. He wanted to trade vehicles for the afternoon so I wouldn't be left without transportation. I told him he could do better than that; I'd come along and help since I had nothing else to do.
So, late Saturday morning I went by and picked up my stuff from Lisa's patio and then, rather than go back home for lunch when I'd just have to come right back to go to Will's place, I went to the deli. And Debra happened to find me just finishing lunch, which brings us back to the beginning.