(R/18+) Outercourse: A Confession and Guide

Warning: Contains mature themes.


It was a rare opportunity.

The sort that only came perhaps a handful of times a year.

I found myself with an upcoming weekend when I had zero responsibilities, neither with work nor with family (note: I’m not married, don’t worry).

Deep in my gut I knew I had to make the most of this opportunity; after all, you know damn well that I’m an opportunist as you may have figured out from my previous confession here.

I was going to take the chance to have another staycation, locking myself up in a hotel room for the weekend all by myself, shut off from the world. I was expecting to spend it alone, since it was such a last-minute thing. I thought it’d still be fun; I could jack off and fuck my Fleshlight, and I could do it as loud as I wanted to.

I decided to take a chance anyway and post an ad on Craigslist. This was right around the time before they took away the Personals section. I didn’t expect a reply, but I believe that you never know what you might get.

Then I got a reply. It was a girl who was coming to KL to catch the premier of The Avengers before it played in her state. Her idea was to take a bus to KL, watch the movie, linger around a mall somewhere and take the last bus of the day all the way back.

As we got to talking, something funny happened, something that tends to happen when you run into a fellow Craigslist frequent lurker. She said something that rang a bell, and I immediately realised that this was a girl I had contacted before. We never met or anything, but we did have quite a lot of phonesex and sexting in the past until we stopped talking for a few months to a year.

I reminded her of who I was, and at that moment, the arrangement was pretty much confirmed since we both had a history with each other.

She was apprehensive about spending the night with me, but I told her that since there were no other takers the offer was hers to accept or reject. I also reminded her that I was more than willing to take the weekend solo.

This is something that the women in my life understand, or at least I try to get them to understand: I would very much love to have them with me, to participate in the festivities, but if they weren’t there I’d still be capable of having loads of fun with myself.

I don’t believe in the concept of having ‘blue balls’.

I’m cumming, with or without you.

But I digress.

She gave me her word that she’d decide, at worst, by the night before the staycation. Lucky for me she decided to go through with it anyway, and the next thing we knew, we were both locked away in the serviced apartment.

I brought lube and I brought my toys. This young fresh grad (I have a thing for girls in their early 20s…..and for girls in their late 20s and 30s and 40s as well, to be fair) brought with her a cute backpack with her toiletries and a change of clothes.

Prior to this moment, there was a period when she was nervous because she had a condition that she wanted to put in place for our staycation. Probably the only rule she had, and that was she did not want to be fucked. She was a virgin, and she wanted to keep it that way, but she was so scared to tell me. She thought I wouldn’t entertain her if she took that off the table.

I laughed my ass off when she told me that, right before she asked, “Do you still want me to stay with you?”

After I composed myself, I calmly informed her: “There are plenty of other ways I can have my fun with you, even if you won’t let me fuck you.”

She, and now you, were going to eventually learn what I meant by this.

Hopefully you’ll be able to take a few lessons away from this for when your own situation calls for non-penetrative sex. Since I’m trying out this whole new confession/guide format, the following will not be in any particular order.

After all, the entire weekend was a blur of one orgasm after the other, so I couldn’t even put this in sequence even if I wanted to.



As with all my encounters, we started off with a lot of heavy making out, cuddling, and groping. It kicked off in the living room/dining area of the apartment but I then moved it to the bedroom so that I could sit on the comfy chair and have this girl on her knees before me.

My pants found its way to the other side of the room pretty swiftly, and the thing I loved about this girl was her unfiltered enthusiasm about consuming my cock whole. Intermittently, she voluntarily deepthroated me. I was impressed; not only did I not have to ask her to do it, it showed me that she had quite a resilient throat on her. This signalled that her throat could take quite a bit of rough treatment.

Taking this into consideration, I got up from my seat and slowly inched towards the bed. I moved slowly because I wanted her to keep my cock in her throat as she moved backwards, still kneeling on the floor. The room was dark and the only thing she could see was me, so I guided her backwards until her back was firmly pressed against the side of the bed. Perfect position, too, since I could admire her (and myself, I’ll admit) in the full-length wardrobe mirror to my left.

With my hands firmly grasping her head, I started to treat her mouth as more (or less?) than just a mouth. Her mouth was simply a part of her body that I chose to fuck.

I started slow, letting her sync up with my rhythm, but my intensity and my motions started to pick up a bit of speed; I withdrew a little, and then gave her a lot more. Gagging, coughing, drooling all over her chest; she didn’t bother trying to clean herself up, and that made me like her even more. Nothing turns me off more than someone who stops mid-fuck to wipe her chin; this is sex, not breakfast. Let yourself go and enjoy it.

I remember feeling like an absolute pornstar as I watched myself in the mirror to my left, thrusting into her head while her hands tried to find something to hold on to for reassurance like my thighs or the bedsheet behind her head.

I kept going until I was ready to have my first orgasm, and when that time came I pulled my cock out and pulled her hair back and to the side so her left cheek was presented to me. That was where I loudly and unapologetically shot my first load of cum, and as is my signature more I dropped to my knees and kissed her with it all mixed up between our lips.



This girl had a decent pair of titts (not that I mind small tits, for the record). This made it possible for us to engage in titfucking as well; either with me sitting on a chair and her squeezing my cock between them, or with her laying on the bed and me kneeling on top of her.

With my knees on either side of her chest, I could park myself where I needed to be as I groped her tits and squeezed them together. Naturally this requires lube to be done effectively, though saliva is good enough (Bonus points if you use lube + saliva; that’s the best mix).

My favourite part of titfucking? I’m close enough to lean down, hold her head and kiss her on the forehead.

Or spit in her face, depending on the vibe of the moment.

This act also puts you close enough to stimulate her as she stimulates you; her breasts are right there for you to fondle (the right way, hopefully), her nipples are there for you to tease, while her neck and hair are both close enough for you to grab and control.

As you can see, titfucking checks a lot of boxes.



Frottage basically means to grind against someone. Being such a generic action, it could be done with just about any bodypart of another person.

In the case of my staycation, there were moments when the girl wanted to be the one to grind against me. For her, it was walking right on the edge, since she was grinding her pussy hard against my throbbing cock, careful to make sure I don’t accidentally penetrate her. She was moaning at such a high pitch, I presume because her grinding was not only stimulating her pussy but also her clit. All of this was external, but it was still physically pleasuring the both of us.

In some movies, you may have seen some men do it with female armpits. There are many cute names for this particular act, but the premise is pretty straightforward: lube up her armpits and get her to squeeze hard around your cock as you thrust in and out. I’m not a big fan of this myself because this position does not allow you to engage in proper eye contact, and because you’re too far to properly grope or stimulate any important parts of her body. In other words, I’m not a fan of pitfucking because its too one-dimensional.

In my case, I decided to surprise her by fucking her between her thigh gap. We were watching TV half naked between rounds, enjoying Nasi Lemak burgers, when I saw how amazing her round ass looked right there in front of me. An idea clicked in my head, and since we were in staycation mode I didn’t exactly have to wait for permission.

I mounted her from behind, and with my lubed cock I slid it down right into her thigh gap and started fucking it like it was any normal part of her I’d fuck. At that angle, I was not only grinding against her ass cheeks and part of her thighs, I was also grinding against her asshole and probably her pussy as well. Stimulating her at multiple points, presumably in such a way she’s never experienced before, caused her to react very strongly.

The best part of hittin her from behind like that is that its similar to fucking her in the same position: her ears, her neck, her shoulder were all within reach. I could, and did, moan into her ear and sink my teeth into the side of her neck.



Here’s what most people don’t realise about feet. Our feet have arches, yes? So what happens when you put two arches together like the image above.

Take your time. Think it through.

If you’ve figured it out already, I’m proud of you. Now you’re following the same thought patterns as I do.

During this staycation, I didn’t get to fuck the girl’s feet because she wasn’t comfortable with the idea. Not only am I not one to force or beg, I had plenty of alternatives to play with instead. Having said that, if you’re in a position to use this, I suggest you should.

Have the man slide his cock between your feet and get him to hold them together with his hands (It’ll be far too tiring for you to do it yourself). You could be laying on your back in one of those yoga-like poses where he can fuck your feet while maintaining strong eye contact with you (and he might be able to reach and spank you a little from where he’s standing).

Alternatively, this could also be done while you’re on your stomach with your legs up in the air.

Quite frankly, any position in which you are able to place your feet flat against each other can be used for this. The only thing you need to ask yourself is where are you going to let him cum? If you’re on your back, for instance, he could probably unload onto your ass, your back, or the back of your head if he’s really getting into it.

Ass Eating


There was one of the moments we shared where she was alternating between jacking me off and blowing me. Somehow, I rolled over and got onto my hands and knees because I wanted her to play with my cock from behind. As you may have seen from my last confession, I kinda like being milked.

Put a man in the doggy-style position and milk him, ladies!

But I digress again.

In any case, I’m a big fan of eating ass (assuming the ass looks tasty enough), though I’m usually on the giving end.

I’m assuming my ass must’ve looked like a snack to her at that moment in time (I do keep myself waxed on a monthly basis), because as I was on my hands and knees moaning at the wall feeling her jack me off, I was hit by something I did not expect.

I felt a tongue. I felt lips. I felt an entire mouth wrapped against my ass.


“Holy shit, this bitch is eating my ass”, I thought to myself

I deliberately voiced out my thoughts. “Holy shit, you’re eating my ass. I can’t believe you’re eating my ass.” I wanted her to hear me describe what she was doing to me. I felt her giggle against my asshole and at that moment, the level of pleasure shooting up and down my spine multiplied tenfold.

That is the very reason why I usually do it to other people, but to have the tables turned against me and my own secret weapon used against me, I swear to god the neighbours must’ve heard me groan like a wild animal.


At the end of the weekend, she left the building, got on a bus and headed home to the other side of the country and I went home to the other side of town. The both of us left pretty satisfied, and respecting her wishes, I did it all without ever having to penetrate her the way she asked me not to.

What I hope you walk away from this article with is the understanding that sexual energy and pleasure can be shared between two people in more than just the traditional ways. My personal philosophy is simple,

If the both of you cum, and if the both of you are able to share that experience, then that is what sex is all about. Positions, methods, fetishes, those are all finer details, but what’s important is that it is an experience shared between at least two people.


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