I let him cum on my face, and other things I did on Saturday night (Shenanigans)

I’ve written this post three times now. Turns out when you write a post on WordPress on an unconnected iPad then connect it, it deletes. This is not the first time it’s happened to me. Sigh. I’d like to think the first two drafts were better writing with more nuances. Oh well. At this point I just needed to hammer it out. Enjoy the bluntness.

If you haven’t read any of the posts about him, you can start here.

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I hadn’t seen P/ShenanigansΒ in 10 months or so. The game playing was too much for me to bear. I’ve told him goodbye more than any other man I’ve slept with.

Why? I wrote a lot about it. He was, in some ways, a perfect “Friend” with Benefits. I didn’t see any relationship potential with him at all – and therefore was able to simply enjoy the moments and the sex. When it came to the sex, was he the best? No, not by a long shot. That award still goes to NIM, unfortunately. Why is it always the emotionally unavailable ones? But the sex with him was good.

I stopped writing about all the times he reached out to me, and the brief dance back and forth we would do, before one of us said “mercy” and we stopped again.

I unhid my dating profiles on Plenty of Fish and OK Cupid a few weeks ago, and put up some new pictures. Shortly afterwards I heard from him on POF: “Your new pics look great btw, wow. Very nice :)”

I simply responded “thank you”.

To which he countered “are you free tonight?”

I paused, and sighed. And thought for a while how I was going to respond. Prior to his calling me to tell me about his failed date, the last thing I’d said to him was to not bother reaching out until he learned something.

Asking directly if I was free was different for him. The reality was, I was free. I had no plans. I’d had a great experience with Jason the day before. I had no dates and no real prospects, other than the crazy Italian who I knew only wanted sex. I said:

Yes, I happen to be free – why?
Him: I have to see you again, Ann. It’s been too long.

Every time prior, the moment I said I would see him, he would then turn around and pretend he was thinking about it, and would ask why I wanted to see him. He needed that ego boost and it was exhausting.

And of course there was the infamous discussion about never bringing wine because I wasn’t his girlfriend. Frankly I’m tired of men who won’t bring a bottle of wine if I host, or who won’t take me out for a drink or – gasp – dinner. I was curious whether he would be consistent with his past behaviour, so I asked “what were you thinking for tonight?”

Him: A glass of wine and a catch up chat.
Me: Sure let’s do that. What time and where?
Him: Your place at 6?

On the one hand, an earlier date was new and I liked it. But there was no damn way he was coming to my place as a starting point. So I said “how about this newish bar near my house that I’ve been meaning to try?”

And miracle of miracles, he said yes.

Our date was on.

We sat for more than 2 hours over drinks and dinner. I had forgotten how young he was, and how occasionally uncomfortable in his own skin he seemed. I had forgotten the insecurity he manifests and that he doesn’t command a conversation. But I can have a conversation with all but the most reticent participants.

It was an alright dinner date, all things considered. I invited him back to my place. We sat on the couch and I waited for him to make a move. Finally I asked him why he hadn’t, and he responded that he sometimes liked an aggressive woman. Right. Feeling magnanimous I proceeded to give him a blow job that he will hopefully remember forever, given the touching and other things that went along with it.

When I couldn’t stand it anymore I took off my lace panties and mounted him on the couch where he sat. I forgot how big and hard his cock was. The reality is that he’s very tall, very good-looking, has the stamina of youth, and a great cock. He’s not a particularly giving or talented lover otherwise – and he’s gotten by on those other assets.

I was able to make myself cum rather quickly – and the muscle memory kicked in for him and he remembered what I liked and tilted his pelvis that certain way. It felt fantastic. I then turned myself around – he loves my ass – and rode him that way as well.

He then took me over to a side chair and told me he wanted to fuck me over the chair, which we did. Then he said he wanted to take me on my stairs, so we did that too. It was almost as if he’d had fantasies about both those things and he had been waiting for the opportunity.

Then we went upstairs and had sex every which way for about an hour – including anal, which he had wanted to try for a while and definitely didn’t have much experience with. As I was riding him again he suddenly said “oh god Ann I have to cum” – which was bad timing on my part as I was working my way toward an exquisite orgasm but I figured hey, why be selfish. He then asked to cum on my face.

It’s worth noting if I haven’t already, that I have NEVER let a man do that to me. I told him so and also mentioned I hear it can sting. He suggested I close my eyes and he’d aim lower.

I honestly don’t know what made me agree, but I did. I certainly have no issue saying no to things I don’t want to do. Perhaps it was the innocent and hesitant way he asked. Perhaps it was also knowing that he hadn’t done it before but he wanted to explore, and I liked being the one to let him do that.

So the next thing I had my face hanging off the end of my bed as he stood before me. When he came, I started to laugh because there was so much of it, everywhere – we both giggled about that as I went to my bathroom and towelled myself off. And yeah, the cum in my eye stung.

In response to my inquiry whether he liked it, he said he did, but he also felt it was degrading to me and he didn’t like that part. It’s probably the most honest thing he’s ever said to me.

I wasn’t quite finished so asked him if he would lend me a hand. He said no – and I remembered the selfish lover part again. He suggested and toy and then told me he didn’t have much experience with toys. So I showed him some vibrators and dildos – picking the Hitachi Magic Wand and my favourite dildo. He wanted to watch. I can bring myself to orgasm that way very quickly, especially after having so many already.

But he got bored and after watching me for a while, went to my bathroom to clean up. Although I felt great, I really didn’t want to continue while he couldn’t be bothered to hang out or even participate.

When I told him such, he said that he felt since I was insatiable it wasn’t like I would ever be satisfied.


I explained to him that my pretty much always wanting more didn’t mean I wasn’t satisfied. It occurred to me that it was likely one of his issues – he’s used to women who blindly do what he wants, don’t challenge him, and who he can best in bed.

We wrapped up our evening and I asked him what he wanted of me – he said to hang out on occasion. I told him I would think about it.

Sometimes, I just want to know exactly what I’m getting, even if I know I can have better.

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84 thoughts on “I let him cum on my face, and other things I did on Saturday night (Shenanigans)

  1. I find myself up early, my kids asleep and Will taking the time for a rare wake-up workout and very aroused (I hope he finishes soon!!!

    Shenanigans seems quite intriguing. He sounds like he could be taught to be more giving. He seemed to enjoy cumming on your face (something that Will has never asked of me or that I am interested in). If he felt it was degrading, why wouldn’t that translate into wanting to help you? Oh yes…youth. Duh.

    I am learning through Will that desire to be generous and giving has to come from within. That’s what happened with my husband. He figured it out entirely on his own!

    • I don’t have much hope that he wants to be taught – it is a fine line with insecure men. There aren’t many ways I can suggest he could be better, without him taking it as a criticism.

      • Tell me about it. I couldn’t bring myself to tell Will what I wanted from him. Thankfully, he read me and wanted to be more for me. Imagine my surprise when he first went down to be generous with me after he came! The doors were kicked wide fucking open! OMG! πŸ˜€

    • Glad you liked the third writing attempt!!

      There are selfish lovers and honestly it is one of the reasons I don’t much bother with younger men – I find men around my age are much more giving lovers.

      • Well, I’m just an old romantic, maybe past the time for giving since there isn’t anyone in my life at present… but with the age, I realize I can’t do what I used to. Then again, I always felt it was better to have quality than quantity… I do pay attention.

        • Well yes, my dear, I do know that. I’ve experienced lovers this past year from their early 20s to probably 60. So I don’t have to wait to be your age to know that older men are way better lovers generally. πŸ™‚

          • I need have my caffeine before I comment. I seem to see things through my limited and narrow experience. Can we trade places for a day or two? I would love a taste of what you experience. Early 20s to 60? Hmmmm. ;-D

    • I can honestly say I can’t see letting that happen again…maybe a rare occasion, depending on the person. I also realize that part of my being willing to say yes was because he was curious. I was relieved he didn’t really love it.

  2. Wow.

    Y’know, as someone who has watched porn since he was was too young to be watching porn, I have to say that I never been a fan of the “facial”. That was something seemed to start appearing the early-2000’s (before that the cumshots were usually in the breasts, or the butt if it was doggystyle). Seeing a woman with cum all over her face does nothing for me, and it does seems like a degrading act. And I’ve often wonder what effect this sort of thing (and porn in general) can have on the young men grow up watching this stuff before they actually sex, how it may warp their expectations, because I’ve never heard of a woman who actually likes that. Many may go along with it, but I can’t imagine what would actually be enjoyable about it, from the woman’s perspective.

    • I absolutely think that porn has made it more of a “thing”… I don’t ever recall it being a discussion or a question before I got married.

      There was a great Ted talk on sex that brought this specific thing up – that basically it’s a porn act and it’s degrading and not something women like. That guys who watch porn are getting an unrealistic expectation of sex.

      It didn’t please me at all. I don’t like the idea of submitting to something I think it degrading. It did nothing for me. I know he was happy I let him try it but he also didn’t enjoy it all that much.

      It was a stark contrast to the Dog Trainer – for whom it was a “thing” – he really got off on it. And I flat out refused to let him do it.

      • Will has NEVER hinted at wanting to do this and I think that if he did, I would give it considration because of where we have been going in our marriage in our openness. I view it as degrading, but in light of what he does with his cum, there *could* be a sensual aspect to my husband’s approach. We don’t like to “waste” any of his cum, so he is rather thoughtful about placement. πŸ˜‰

          • Well, it is a rather different for me. I want him to cum where he wants. I love watching him enjoy the next steps which always leads to more fucking. He gets so turned on by doing that, it is like a natural dose of the blue pill…he is ready for more action!

          • No…but if I did let him shoot it there, he would. But, he is a dear and licks it up everywhere else. He has an entire blog dedicated to it.

      • I LOVED that Ted Talk too Ann….anyone and everyone should watch it. What we fantasize about is erotic. Men (prior to porn viewing) go over in their minds how the conversations will unfold, how they will kiss you first, what your skin will feel like next to theirs, how you will smell, how you will react to their caress, the way your eyes will look into theirs…..not how to degrade a woman in order to feel sexual arousal. Making women cry, rape scenes etc. are not healthy sexual interactions with women. It’s just not. And that Ted Talk explained it better than anything I have ever heard before.

    • Yeah, I don’t get what the appeal of it is either. In fact, it typically ruins a good porn video for me. Nothing worse than jerking off during the last minute of a movie while the guy on screen is jerking off too.

  3. I thought the best sex was always with someone you’ve made an emotional connection with? Are you saying the opposite is true? I’m out of the game, anyway. What’s the diff.

    Feeling magnanimous or feeling manipulated?

    What’s up with cumming on a woman’s face? When did that become a thing? I think it’s disrespectful. I blame porn. What’s it going to lead to 10 years from now? Dumping on her?

    Here’s what I remind me of: Last year, on a lark, I read The Richard Burton Diaries, which turned out to be an awesome page-turner. In one entry, around the late 60’s, he described coming across a couple having sex. He said the woman was, “masturbating him with her mouth.” It was such a clinical way to put it that it sounded like it was the first time he ever came across it. I’m that guy now. I’m that clueless guy stuck in the past.

    Happy landings.

    • Yes, the best sex is absolutely when there is an emotional connection. But I can have pretty damn good sex without it.

      Not manipulated at all, actually. In contrast to the Dog Trainer, who was trying to bully me into doing it. And with him it was a firm “no”. Someone who tries to bully and manipulate me will get my full-on Alpha don’t fuck with me kind of response.

      So this was different.

      That’s such an interesting phrase in the Richard Burton book. I don’t think you are clueless and honestly wouldn’t wish being single on anyone… assuming you have a good marriage and a healthy sex life. But dating sucks.

  4. I will say I’ve let the Russian do that maybe two or three times? Each time got cum right in my right eye. Lol! It isn’t something I enjoy and I’m sure he got the hint after the last time. I found it a little degrading and I would much rather him cumming on my ass, boobs or even stomach. I know for him it’s just a visual and dominate thing. Thankfully he hasn’t asked if he could in a few months!

    • That’s what I don’t like…that it’s such a dominance thing. The face, specifically.

      I’m actually not a fan of someone cuming anywhere except inside me. But I know some guys like the visual so am okay with it on occasion. But I much prefer the intimacy of staying connected.

      Glad to hear he’s not asking regularly!!

      • I definitely enjoy having him cum inside of me (we have yet to do that without a condom) instead of on me. It really is much more intimate and allows for some cuddling afterwards.

        I have two main reasons why I prefer it that way: 1) If I’m on top I can easily continue fucking him till I have an orgasm since he stays hard for a while afterwards and 2) I’m not lying there awkwardly waiting for him to wipe me clean.

        Men. Such funny creatures though!

        • Hey! I resemble that remark! Indeed, we are strange creatures (have you seen what we have between our legs? *That* is strange!).

          When you do progress to having him cum inside of you sans condom, there is an entirely new world that opens up IF he has an open mind about it. Being generous AFTER an orgasm is something that required a lot of motivation for me to overcome my resistance to my own stuff.

          #2 (on your short list) is something that can BE THE FUN with him being generous with you. It is all part of the erotic and arousing fun that “comes” with that activity.

  5. How in the world did I miss this post? Ann, you have been withholding, my dear. πŸ˜‰

    No, Savannah’s right, I wouldn’t ask to cum on her face for the reasons cited here. It just looks degrading (whether the women who allow it actually feel that way or not). The idea of it doesn’t really do anything to arouse me – there are so many other, more arousing activities that can be enjoyed instead (your gag reflex aside).

    Shenanigans has a lot to learn about what lies ahead of his orgasm. One and done is such a low standard to accept. The very reason I created my blog is for guys like Shenanigans to read (as well as the women they are with). Learn from my mistakes!!

  6. Right. Where do I begin?
    I agree that it’s not cool that he didn’t stay with you while you were playing. I guess that’s youth thinking that playing with a toy is you masturbating and feeling left out, rather than think that him watching may have such an arousing power over women.
    About the coming on your face. I guess I am the only one who thinks differently. I guess I don’t watch enough porn to have it associated with disrespect.
    I had a man do that to me once (I still have to write about it, it was such a powerful experience, not necessarily the coming on my face, but the whole experience).
    This is the time when I realized I really would like for a man to take over, to lead, so that I could just let go. It is strange to explain. HE did dominate me that day, and I loved it. And when he asked me to kneel before him and open my mouth and he came aiming for my mouth, I was in such a state that I just did what he asked without thinking twice. I don’t regret having done it for a minute.
    Sadly, he had to rush out the door and it was our last sexual encounter for a looooong time (he was moving out of town a few days later), so there was no licking or any other type of fun play afterwards, but I had never felt as respected during sex as with this man. I have felt respected during sex since, but it was a first time for me.

    • That sounds like an interesting experience and I look forward to reading about it!!

      I like being dominated (as you know) but there is a limit to what I will accept and submit. I also completely agree that in the moment things can be very different.

      • One day, when life becomes boring, I’ll write about it πŸ˜‰
        For now, I have enough matter for at least 3 posts, and that’s not considering the ones that have been in draft for a while πŸ˜‰
        I guess that the experience was different for me because a) I didn’t know yet I liked being dominated; b) I had no experience in what is domination (I had never read a sex blog, hadn’t even read 50 shades, to show you how little I knew!); c) I don’t watch porn and have no idea of what is expected, so I just took it in my stride. None of it got into my eyes as he was aiming for my open mouth, so I didn’t have the sting of that, and really, I didn’t see a difference between him coming on my open mouth rather than in my mouth, wrapped around his cock. It did feel a bit weird for an instant, but I was way more annoyed at the fact he had to go so quickly afterwards than by him coming on my face πŸ™‚

  7. I’m thinking of the right response… He’s the type of guy you know you just need to be done with but sometthing always has you agreeing to that one more meeting. I had a lover like that, but he let me down because his life was “complicated”. That shit gets so old.

    On another note, i let my recent lover cum on my face. A first for me that I keep meaning to write about.

    • Perhaps there is something in the air – I look forward to reading about it!!

      And yeah, he is kind of like that. But it had been almost a year so I felt pretty good about my ability to resist!

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  9. A wild post, and this guy certainly comes across as selfish by not helping you out — after you accepted his request to come on your face. That you gave him that gift should’ve made him want to return the favor in pleasing you back.

    Facials are definitely a porn thing, and I wonder if doing it would even occur to guys if it wasn’t for porn. After seeing porn, I admit that I’ve been aroused by seeing facials — but I don’t want to try it in real life. Coming on breasts is much sexier to me, less degrading, and less likely to hurt by getting in her eyes. Sex is supposed to be about both people’s pleasure.

    Thanks for the tip about the TED talk. I haven’t seen that, and I’ll have to check it out.

  10. A memorable evening, for certain, filled with highs, lows and sticky firsts. I applaud your moxie and honesty, Ann.
    You’re a special lady. Don’t ever change, please?

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