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when to let the freak out

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I recently had sex with a women I've know for a long time and really care about, we've known we like each other and get along great. She became available and I made love to her in the manner in which that terminology applies it was sweet and passionate as the mood seemed to dictated. But while in the act I was running ideas through my mind of what I wanted to do. She behaved in a way which suggested to me a lack of sexual exploration. In the end I resited urges to do things conventional morality wold wrinkle its nose at. Things fell apart for other reasons but after reviewing the whole thing I asked myself the question, "When is it ok to let the freak out?" In the case of a women you intend on seeing as more than a fling, do you introduce what you're capable of slowly, or get filthy right away?
“Things conventional morality would wrinkle its nose at.”

Olivia has a raised eyebrow and a little smile right now as she wonders how freaky you want to get with your new girl. Freaky means something different to everyone and since you didn’t specify it’s hard to know where it sits on the scale.

Ideally, when you find a prospective girl that has potential for going the distance with you, you aren’t going to want to feel like you’re hiding anything or holding back in bed. But every level of ‘freakery’ must be broached cautiously, especially if the girl appears to have conservative tendencies.

I recall this one time when I was younger and far more innocent minded that I was going out with a cool guy that seemed to have all the moves. We were on our third date and I had been wanting to take it slow. He had just cooked dinner at his place… lobster drawn with butter, candle-light, wine and chocolate cake for dessert. Pretty impressive for a 22 year old guy! Clearly he had pulled out all the stops. But somewhere in between dinner and dessert, and perhaps buzzed off the wine he proceeded to tell me quite out of the blue how he had various dildos in his bedside table that he liked women to insert into his ass during sex and how this was one of the only ways he could orgasm. I tried to smile serenely through it all as he seemed extremely comfortable with the topic and continued to get into more detail asking me if I would be cool with wearing a strap-on. Now what I was thinking at the time was… perhaps he might have wanted to wait until he got to second base before pulling that rabbit out of the hat?

The point is, everything outside of mainstream sex has its time and place and in most cases it should be gradual, depending upon the comfort level of your partner. If you happen to find yourself on a date with a porn star like Kristina Rose, chances are you can get your freak on before your pants hit the floor. But for a younger, inexperienced girl that you’re just getting to know and who might seem a bit sexually shy, you’re going to want to go a little slower.

How Freaky is Too Freaky?

Let’s consider the different levels:

1. Basic Sex – oral, vaginal, standard positions like missionary, doggy, cowgirl, 69
2. Upgrade to Basic – anal, rimming, facials, piledriver, dirty talk, light role-playing, rough sex
3. Kinky – handcuffs, rope, blindfolds, advanced role-play, light sub/dom
4. Freaky – watersports, humiliation, ballgags, nipple clamps, threesomes, gangbangs, DP, BDSM, strap-on, costumes, fetish play, bukkake, gokkun etc.

Now, it’s safe to say that on your first sexual encounter with a girl you really like that you can select anything off the menu from level one and shouldn’t run the risk of shocking of offending her. If you haven’t really talked about sex with her before and she doesn’t give off the impression that she is a sex in the bedroom, it’s best to gage things with her first before progressing to Level Two. Sometimes you are pleasantly surprised and can get there all within the same sexual episode, but if she seems awkward or uncertain, then don’t force things during the initial encounter.

After you’ve had sex, you should be at the stage where you have opened the door to intimacy and communication in general. After all, you have just been inside her. It’s license to have a real conversation about sex at this point.

I suggest doing some gentle probing (no pun intended) by asking about her sexual fantasies or desires. Act like your goal is to learn more about her likes and dislikes because you want to please and pleasure her and treat her like the goddess that you know she is. Your desire to learn about her needs will make you look like a very attentive lover and she should feel comfortable about opening up about things. If she turns red and says “I don’t know,” then you can start asking her guided questions like “have you ever tried anal?,” “have you ever had a tongue in your ass?”, “do you like being tied up?” and rolling right up the levels until you hit your desired level of ‘freakery.’

Once you ask her what she likes, she will likely ask you what your kinks or fantasies are in return. Women are usually very sexually polite this way. This is your opportunity to talk about what you're into, and what she would be willing to explore with you. Questions like "how do you feel about peeing on me?" or "can my buddies DP you while I am tied up in a corner watching, with a ball-gag in my mouth?" may seem shocking at first, but in the realm of a healthy sexual relationship you should be able to talk about anything. If she seems genuinely disturbed by anything you say and you feel like you've gone too far, you can always default by reassuring her that you're just talking in the realm of fantasies.

Now most of the time, you can figure things out just by exploring things together in the moment and it evolves without requiring any kind of overt Q&A period. But I’m assuming we’re dealing with a shy girl here so you might have to take the reigns in upping the kink level. She might be inexperienced but that doesn’t mean that you don’t have a potential sex-pot on your hands here. With a creative partner, many women blossom and can become far more adventurous than they might have imagined. She might even end up freakier than you!

Another suggestion would be to go to a Sex Boutique to check out toys, costumes and kinky paraphernalia together. Most of them are very couples-friendly these days. This will open up the dialogue as you gaze and gawk at the dizzying array of things you can add to your sex life. You can also watch some kinkier porn together to gage her comfort level with certain things.

From there you should be able to roll in whatever direction your sexual interests want to take you.

Now going back to your original statement about freakery and things that “conventional morality would wrinkle its nose at.” If I haven’t covered your particular flavor of freakery in this post (and provided its legal and within site guidelines) or you need more guidance then let me know and I’m happy to get more specific with my advice.
LOL, there are a lot of freaks here at Lush...self included. Before I joined the Lush site, I thought most of that was vanilla.

Somehow I almost feel, escalated!

This was the perfect thread to read, the first thing in the morning.
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
I hadn't thought of the nominclature. I wasnt even approaching freaky I guess I was thiking upgraded basics. But in the manners of kink and freak it shouldnt be a surpise and I take that advice in the future. In terms of how "out there" a person could potentially get it seems like I should have gone a little farther if I wanted to standout from her more conservative past lovers?
Well, you want to stand out from her conservative past lovers, but you also don't want to push things too quickly or it could scare her away. As my earlier post said... take it all in stages.

A great little upgrade-trick that a lot guys overlook is the sex appeal of a dominant man in bed. Growl in her ear, get intense, make her feel like she is the hottest piece of ass that you've ever had (even if in reality she is frigid and a total butterface). Take control of the situation and don't be afraid to be a little rough. This doesn't mean that you should go 'cave-man' on her, but trust me... women often respond in an instinctively primal way to a man that knows how to exhibit dominant alpha energy.

Sure we love the gentle lovemaking, and we're ok with the frat-boy sex routine after we've had a bit to drink, but a man with a confident intensity that can take control will always have us purrring for more.
Quote by allnight
I hadn't thought of the nominclature. I wasnt even approaching freaky I guess I was thiking upgraded basics.


Hey man, if you like to use feathers during foreplay...I think you're still in the upgrade basics area. Now if you wish to introduce the whole chicken, I think you're probably looking to go to step 9. Maybe 8.

Any of you other freaks care to comment? Or are you just beating off reading this thread?
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
Shouldn't one move into the freaky sex zone slowly, unless they tell you right away to let the 'freak out!" Then just do it!
Bust loose withe the thick rusted chains, the iron shackles, and the branding iron.
Get into bed then shout shout let it all out!
you know if you brought the freak out the first night she might just bug out

can ya wait until perhaps ya both feel comfortable with each other

say after the passing gas phase

just think after one night you need to give her a few more sessions...first...
Hell just tie her up & keep her that way until she gets use to it...
Don't try it at home or in front of your other half.
Anecdotally (is that even a word?)...

There have been a time or two where I have successfully 'let the freak out' in real life (as opposed to cybering online or talking to people online who have the same freaky interests). I talked about it probably the second time we hung out after we already had sex. Basically, I asked her whether she had thought about threeways. She mentioned she had thought about two guys and a girl. I told her I was interested in that (and was wanting to do that, but didn't know a guy buddy who was into that) and told her I would help her fulfill her fantasy if she found someone.

But that wasn't what I had in mind originally. I asked her about a ffm threesome and she seemed to contemplate the idea. In fact, there was a hint of intrigue at first since she talked about messing around with girls. I talked about it with her at a later date (we were sleeping with each other over a period of time and that initial openness seemed to help things) and we talked through some scenarios. Originally, she was squeamish about licking a woman but we talked about just having me and the girl concentrate on pleasuring her and removing the requirement of having her interact with the girl. She seemed to be more agreeable to that scenario.

Things ended before we could try out what we talked about but I think Olivia is correct. Introducing things as you get to know each other better is the way to go. The other thing that seems to work, too, (as this is not the only time I've 'let the freak out') is by being open and pouncing early (like after the first time you sleep together). If you don't make it known you have some kind of freaky nature, she's going to make the assumption you don't, and two months down the line might be too late to reveal that handcuff/ballgag fetish.
For me, it totally depends on the guy and the situation. Sometimes there is an overwhelming sexual connection with someone and especially if it's more of a casual or fuckbuddy situation, I'm more likely to let the freak out earlier on.
When a man makes me feel sexy and desired, when he's kind and courteous and respectful, I'm more willing to push my sexuality beyond the norm. And more likely to enjoy it.
As long as there's an active level of trust and you've discussed each other's desires, why not give it a go?