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Ok, well just to clarify, by 'whipping' do you mean using a single-tail whip (like Indiana Jones' bullwhip) or do you mean using a flogger, like a cat-o-nine-tails? A single-tail is extremely hard to use safely. It is not something you use on a live person without having practiced with it for a very long time (I once read a dom who said that if you can't use a single-tail to flick off a light switch on the wall, you're not ready to use a single-tail on a person). Single-tails used improperly can be extremely harmful to the sub; they can rip skin open, leave blisters and bruises, and leave the user with tennis elbow. They require a lot of space and a clutter-free environment. So, if you were hoping to jump right into playing with a single-tail, DONT. I'll assume you mean a flogger and not a whip.
If you have an erotic toy store in your city, browse its selection of floggers; a good flogger is balanced just behind the knob at the top of the handle (the knob from which the tails emerge); a balanced flogger will not tired your arm as much. Look for one with soft leather tails; as a beginner, you don't want tails made from harsh materials that will scrape the skin. The Newcomer's FAQ has a note about basic flogging safety, so make sure you read that. Another point; good flogging is mostly in the wrist, not the elbow or the shoulder. Lots of arm swinging will tire you very quickly, so practice figure 8s and other wrist flicks with the flogger. (By the way, I'm not super-experienced in flogging, only done it 4-5 times, so don't take me as the expert in the field.)
Flogging has a sort of old-style quality to it; it seems like something out of centuries past. So flogging scenes lend themselves nicely to pseudo-historical scenes. Maybe you're a witch hunter and she's an accused witch. Maybe you're a cruel nobleman and she's a kidnapped peasant girl. Maybe you're a Roman patrician and she's a runaway slave girl. Maybe you're a priest and she's a young woman who has confessed to impure thoughts. Maybe you're a Nazi and she's a captured spy.
Start the scene by role-playing the reason why she's being punished; that will get you both into character. Strip her naked and fondle her or humiliate her (if she likes humiliation), and call her a few names; basically do the foreplay to get her aroused. Erotic pain is much easier to manage when the sub is already excited. Then tell her what you're going to do to her; that will heighten the tension. Heighten it further by showing her the flogger and slowly running it across her skin. Tell her you're going to give her 10 lashes as her punishment. Tell her that she has to count each lash out loud. Then bring the flogger up and down gently, striking either her ass or her shoulders (but not her neck or her lower back). Make the next one slightly heavier, but not much, and gradually build the force of the blows.
But this is a beginning scene, so the point here is not to pound her back as hard as you can; the point is to introduce her to flogging. Beginners sometimes thing the whole point of flogging is to hit as hard as possible, but it's not. Force has a role to play, but a major part of the effect of flogging is the repeated stroke on the same body part. What feels completely ok with one hit becomes harder to manage with 10 on the same spot. (Try it yourself. Take a ruler or a crop and slap your forearm with it repeatedly; you'll quickly start to feel a sting build up.)
If, after 10 strokes, she's ok, tell her that she's going to get another 10 strokes, maybe on another body part that's safe to flog. One way to assess how she's doing is to work a safeword into the scene. Let's say you're the witch hunter and she's the witch. Tell her that whenever she needs the flogging to stop, she is to say "I'm a witch!" (If you're a priest, the safeword is "I repent"; if she's a runaway, "I'll never run away again". Agree to this before you start the scene.) That way, when you flog the accused witch, she can beg you to stop and you won't. After 10 strokes, ask her, "are you a witch?". If she says "no", you know she wants to keep going. If she says "yes I'm a witch" you know that she's had enough. If she uses the safeword, that's the end of the flogging for the night. Move on to something more gentle, like intercourse, or cuddling. Don't move on to another type of pain play; for your first scene, make the flogging the climax of the harsh phase of the play. You need to ease her into pain gradually; those mild first few scenes will help her find pain arousing (especially if you precede and follow it with more vanilla play like fondling or oral sex), and it will make it more likely that you'll eventually be able to progress to heavier pain down the road. Perhaps part of the scene is that if she confesses to being a witch, you will reward her (by giving her some form of sex play that she particularly likes, whether that means you going down on her or her going down on you). Knowing that she gets to control when the scene ends (by deciding when she wants to use the safeword) may make her feel more confident that she'll enjoy it.
Another important point: a good dom never does something to a sub without knowing what it feels like himself. So if you want to explore flogging your gf, you should let her flog you once or twice. I've found this principle to be one of the keys to becoming a really good dom; it will stimulate your imagination, help you see the scene through the sub's eyes, and will help you avoid going too far.
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