I remember the first time with an almost crystal clarity. My first taste of a bit of leather. Like any other adolescent boy I had fantasies of bedding quite a few of the girls I knew. One of these fantasies concerned a young lady by the name of Diane, whose last name shall go unmentioned.
Diane was a very pert young lady, very active, always smiling. Brown hair in a short style that actually did wonders accenting her face. She had full, pouting lips and gray eyes that sparkled like moonlight on the ocean. I used to just stare at her body when it seemed no one was paying attention. I would dream of how she looked nude, which wasn’t really hard because of the clothes she wore. Nothing really revealing but enough to let you know that she had a body that perfectly complimented that beautiful face. I know she stood 5’6″ and I would have guessed that she was about a 34B-22-34 or somewhere there about.
I never would have assumed that I could ever have a chance to even date Diane, much less have sex with her. She never seemed to date any of the guys in the group, always saying she was seeing someone and that was pretty much it. It seemed all the guys we hung with (and I’m sure a couple of the girls) tried to ask her out, but each met the inevitable “No.” Now I know I’m not the greatest looking guy in the world, far from it, I think my only attraction lies in my lunacy. So after seeing these guys shot down there was no way in hell I was going to risk asking her out on a date, she never seemed to really notice me anyway so I figured I would just keep worshipping her without her knowing.
The funny thing about the whole situation was that most of the time we were all together. I won’t go into specifics but there were never less than 8 of us and sometimes maybe 12 to 15 just going out and doing things together. We’d go dancing, shoot pool, swimming or whatever there was to do to pass the time so the guys that had asked her out were there, the problem was they wanted it to be just the two of them and that’s where she drew the line. She didn’t want to be with any of us but she loved hanging out with all of us.
So one night we got together to go out and shoot pool and there were about 9 of us and we were all having a pretty good time. I noticed Diane flirting with a couple of the guys at the pool hall, but then that’s what we all did. We’d see which of us could hook up with someone and leave with that person. Diane never really played that game, always leaving alone or getting a ride from someone in our group if whomever she had come with had left with someone else. She always seemed to laugh about the game and never actively participate. Until tonight, suddenly she was playing, and playing well.
Well through attrition via the game and sickness (some of us couldn’t handle our liquor) Diane and I were the only ones left. She had been giggling and smiling with the last of the flirts as it were and didn’t notice everyone else was gone. I was getting pretty tired and it seemed obvious I wasn’t going to be leaving with anyone so I went over to Diane and asked her if she was going to be able to get home okay. The guy chimed in saying he’d get her home. Diane looked around and asked where everyone was. I smiled and nodded and she knew where they all were. She asked me to hold on and told the guy she had to go. They exchanged numbers and she gave him a small kiss on the cheek and joined me for a ride home.
In the car we talked a bit and she remarked that this was the first time she could remember being in my car. I smiled and said yeah, I thought it was the first time. We shared in some idle chat, and then she asked me why I had never asked her out. I mumbled a little and said that basically everyone else had asked her and she had turned each one of them down, so I figured I’d save myself the embarrassment, that and the fact that she had a boyfriend. I commented that it was a boyfriend that none of us had ever met but a boyfriend none the less. She asked if we thought she had been lying about this boyfriend of hers. I let her know that we all just accepted it as far as I knew and that none of us had ever questioned it before.
Then the bomb dropped. She said that she had been seeing someone, but that it had ended the weekend before. He had gotten a job out of town so him and his wife and family had left. I sat there amazed. She had been seeing a married man. And worse, a married man with a family. She asks me then if I think any less of her. I look into her pretty gray eyes and all I can say is that I could never think anything bad about her.
We pretty much cease the talking until I get her home. I notice the house is completely dark, no outside lights on or interior lights. She smiles and says no one is home. Then she asks if I’d like to come up. I don’t even answer, I just shut off the car and open my door.
We go into the house and she just stops at the front entrance and she kisses me. Nobody’s fool, I kiss her back. She takes me by the hand and leads me up the stairs to her room. I can’t believe what’s happening. I’m here with Diane and we are headed up to her room. I’m dreaming, that is the only explanation for what is happening here.
Then the next bomb. She sits me down on the bed and says she has something to tell me. I’m all ears as she explains that the man she was seeing introduced her to some things that she would never have thought of before. Seems this guy was into some serious Sadomasochism and Bondage and Discipline. He liked to tie her up and punish her for stuff and she in turn learned to like the same things. She seemed pretty sure I wasn’t going to spill what she had told me but did seem concerned that I might not want to join her for a new adventure. She needn’t have worried, I hadn’t really thought of doing anything like this before but I was sure she couldn’t really hurt me so I was almost eager to see what might happen.
She showed me a locked box that she had hidden under her bed and pulled the key from the chain around her neck. She opened the box and I could see a whole mess of stuff in there that looked kind of scary. She took a little bag with her into the bathroom, telling me to not look into the box and that she would be back soon.
When she came out of the bathroom, I thought I would die. She was wearing like 4-inch stiletto healed black leather shiny boots, black fishnet stockings with black crotch-less panties, a black garter belt and the kicker, a black nipple-less bra. I couldn’t believe my eyes. Her skin was like fine ivory totally in opposition to the color of night she dressed herself in. Her nipples a wonderful pink with very wide areolas. She walked over to the box and when she stood from it again she had two sets of handcuffs, something that looked like manacles and something small and black. She smiled and asked if I was still willing. I was a little worried, but yes, I was still willing.
She came over to me and put her lips to mine, darting her tongue in and out of my mouth, slowly, almost painfully teasing. I put my hands to her beautiful bare nipples and she slapped my hands away. She stepped back and gave me a look that spoke volumes. She was going to be in control and I was just supposed to enjoy it. She spreads my arms, putting them out to the sides and then she starts undressing me. Now I’m naked and she’s looking at my dick. I like the look in her eyes and I smirk, she smiles and I again take notice of the objects she’s pulled from the box. She flicks her wrist and I feel a sharp pain on my cock. She hit me with what looks like a short baton. Diane is really into this pain stuff and hurting, she’s scaring me a little. She tells me to lay face down on the bed and spread my legs and arm. She puts the handcuffs to my wrists, cuffing me to the bedposts. She then uses the manacles to chain my legs to the bed. I’m lying face down and prone. I pray to God that she isn’t going to do anything too freaky to me.
She starts by climbing onto the bed next to me. I feel the heat of her pussy on my back as she sits facing my feet and she starts playing my ass. She’s slapping my ass and for all the discomfort I can’t do a damn thing about it. I can feel my ass growing hotter and hotter as she spanks me. Then she gets up off me and I feel the cool air on the wet spot on my back from where her pussy was dripping. She stands up and bends over, kissing my ass cheeks and slowly rubbing them all over. Then she bites me, my cheeks and she bites them hard. I can feel the tears and the anger swelling. She is horrible, first kissing then biting then kissing then biting again. I can’t tell what she’s going to do next, be nice or be mean.
She squeezes my ass with both hands then drops down and puts her tongue in my asshole. I can’t believe she did that. I’m fucking tripping that she would do something like that. She uses her tongue to fuck my poor virgin asshole and I don’t know if I hate it or love it, all I know is that my dick is hard enough to break stone. Then she takes that damn little rod and replaces her tongue with it in my ass and I’m starting to strain against my shackles. I’m telling her to stop, to please stop. I don’t want this, please just fucking stop. She stops and pulls it out and I sink into the bed, finally able to relax.
Then I hear her.
“It’s worse when you fight!” That was what she had to say to me after yanking that fucking rod out of my ass. All I can say in response is “Fuck you, you crazy bitch.”
She doesn’t move for a second and I try to get my head around so I can see her and when I do, she’s looking at me like I just did the wrong damn thing. She gets up off the bed and I can tell she’s going back into the box. Then I hear it as it slices through the air and smacks her hand. I look and she shows me the cat-o-nine tails. No! No fucking way. She wouldn’t, and just as I think this I feel that first bit of leather strike my back and ass. She starts hard but slow and she’s asking me what the fuck I called her. Who the fuck did I think I was to be calling her a bitch. As she thinks about this she beats me harder and harder until the tears aren’t just swelling but running down my face and the anger has me in it’s grip. I can feel the welts rising on my skin and I’m fighting her the best I can, which isn’t very good at all considering I’m still shackled. She stops and I again begin to wonder what she’s doing. Then I feel the coolness on my back, at least until it touches the highest of the welts on my back then the burning begins. She’s pouring alcohol onto the streaks on my back and I scream. She just keeps pouring and I keep screaming.
I’m lying there with tears from my eyes flowing down my face and onto the sheets. I’m not crying aloud, but I’m suffering and I’m totally pissed. I’m just lying there, mad and not really thinking about what else might happen to me. I’m wondering at what level the pain doesn’t come anymore.
She turns out the lights and the only light is coming from her. Or more specifically the candle she’s carrying. This I’ve heard of, candle wax. Then I feel it on my ass cheeks and it burns. I tighten my ass and I don’t let her hear me cry.
She takes the candle away from my ass and she turns the lights on. She comes over to me and I can feel her loosening the shackles on my legs, then she takes the cuffs off of my hands.
I can’t believe the pain she’s caused me and here she is, cool, calm and collected. I stand in front of her and I’m looking at her and she is looking at me almost defiantly. I lose my damned mind. I slap her and she falls to the floor. I reach down and I pull her up and throw her on the bed. I have this anger in me but I can’t direct it. I slap her again and again. Her face is reddening and she looks up at me and she smiles. I don’t want her to enjoy this, I want this to hurt and she’s smiling. I grab her garter and rip it from her body, then I take the panties from her and I look at her and I know I have to fuck her. I slam my dick into her pussy and she looks at me and moans. She licks her lips and she tells me to fuck her like a man. Quit being such a pussy little boy and fuck her like a man would, hard and mean.
Damn it I want her to suffer. I turn her over and I slam my dick in her ass and she screams. No niceties here, no lubricant, no slow going, I just shoved my rock hard cock into her asshole. She’s telling me no now, she’s crying and squirming, trying to get out from underneath me and I stand strong and hold her there and fuck her ass fast and hard. Then I notice the handcuffs are still attached to the bedposts and I put her hands into them and close them. Now I’m in control.
I stop fucking her and I get off and I see that she’s kicking her lags so I manacle them to stop all that straining and kicking. Then it’s my turn in the box. I find a whip with this big fat handle and I look at her and smile. I bring it over to her and I start working that big fucking handle into her pussy. I get it up into her about 6 or 7 inches and I stop and I just leave it there. Every time she squirms I hear her moan. Then back to the box. The lighter and the candle. I drip candle wax onto her ass and I see her squirm and I know that handle is hurting her and with each move she is in ecstatic agony.
I blow out the candle and I get back up on top of her and again slide my dick into her ass. But this time as I fuck her I bite her back and her neck and ears, I pull her hair and I stroke it in as deep as it will go. She’s crying and she moaning and I feel the urge to cum. I start stroking faster and harder and she’s screaming now. I want to cum and I’m trying hard to make her know it.
I cum and I pull her by her hips and I don’t let go. I can feel the whip hanging from her cunt and it’s still lodged up there pretty deep. Then after I finish shooting all my cum into her ass I drop back down on top of her and it feels like the whip gets driven up into her pussy just a little further.
The anger, like my cum seems to have just shot out of my body and I realize what I had just done. I slowly pull the whip handle out of her pussy and I unshackle her legs and take the cuffs from her wrists. She’s laying there face down and she isn’t making any sounds. I’m a little scared that I did something really wrong. She slowly pushes herself up from the bed, her hair falling down her face so I can’t see it. She turns to face me and she’s smiling. She tells me I have a knack for this and that with her…tutelage, I could become very good.
Diane was the first to take me on such a journey and I have been on many since, but she introduced me to the many painful pleasures of the flesh. She was the first to call me a night demon but as it turned out, she would be far from the last.