I’m a sucker for a guest blog that melts my heart as well as my knickers, and this week’s guest delivers exactly that. A beautiful story of first time anal fingering, with a glimpse into the blossoming trust and intimate dynamic between the writer and his partner. Please give a warm and sexy welcome to OldManOnAJourney, I am so grateful to him for sharing this gorgeous experience!
First time anal fingering – “I trust you”
A nice Saturday. We walked, sat, kissed, walked some more, and talked. We spoke about sex and kinks, and eventually landed on a wooden bench in a sunny spot, and on the subject of anal. She said it didn’t work for her, she had tried, and I nodded. I recently learned that one can simply accept what other people say, and I find it a beautiful concept.
I must have looked a little amused or thoughtful when I nodded, though, and she probed. We don’t really know each other yet.
So I told her that the women I have had sex with had all wanted to try it, and all but one loved it. A lot. So, interesting to see someone who does not!
She then made a half joke along the lines “well, you wouldn’t want it? Right?” and I confessed that I definitely have fantasies about being fucked. I am not sure whether I’ll have the actual willingness to go there, or whether I am even brave enough to try. She asked more questions, and we explored what was going on in my head. I had never told anyone about it in that much detail, I think.
This woman is helping me be myself. Glorious, really.
I was at hers for the first time a couple of days later. On the way to her bedroom, she asked whether I was afraid of what might happen in there, and I told her that I trusted her. I said it, and I felt it: a flood of ‘wow!’ and ‘I do!’ and ‘that’s sexy as fuck!’ in my head. It was a little shock, almost physical. I remember repeating it, “I trust you”, trying it on, and knowing that I meant it. I remember feeling super calm, utterly safe.
We kissed on her bed, both naked. She stroked my back, kissed my neck, and I ended up rolling onto my belly and just letting her explore.
She spent time kissing my shoulders and neck, her hand on my hip, then got more excited and grabbed my bum and started grinding against my leg. When she asked “can I use that oil again?”, I thought she wanted to use it on herself because it helps her come harder, but she said “… for you …” and I kind of said “YES!” before I’d even thought about it.
So she did. I felt the oil drip on my arse, then her fingers going down between my cheeks, searching, stroking, then probing a little. I felt her hips against my leg, her pushing and her grinding, a little more urgent now. I heard her breathing, and a little noise she made when her finger went in.
I let her do it, and I felt how I settled into it, how I let go. Lying on her bed, naked, spread out with my face buried in the sheets. I remember how I slowly noticed that this had not been on my bingo card for 2025 or any time, really. I remember that I was curious.
“I trust you!”
This woman was getting off on fucking me. I remember feeling sexy. I think we were both equally surprised, curious, eager.
She ended up fucking me with her finger, then two, at some point three, me relaxing more and more and then arching my hips up and pushing into her hand. She was still grinding and moaning, and I kept pushing into her more. I moved my hips around, felt how I felt more open, more accessible, more willing. I wanted to be open for her, wanted her fingers to stretch me, fill me, wanted her to fuck me. I squeezed her fingers, heard her little gasp when she felt that. It was all so right! It was so sexy! She almost came. I would have had an orgasm with her if she had.
I think that was the sexiest moment I have had in a stupid long time, and the sexiest I have felt, maybe ever. Primal. Sexy. Right. I went into mumbling into the sheets at some point, about how I was now sure, how this had done the step from “in my dreams” to “OMG, I want to be fucked, I really do!”, and occasionally telling her that I wanted her to fuck me. Like properly. More. I don’t think I was very coherent.
A little later, I was lying between her legs, kissing, licking, tasting, touching, soaking up her moans and her movements, amazed at how violently she comes, and I was still groggy happy from being fucked earlier.
I hadn’t known it was possible to make a woman come while smiling like an idiot.
Afterwards, she told me that she was surprised how much she had wanted to fuck me once she had realised she was going to do it, and I had another rush of good, warm feelings when I told her “I want you to fuck me properly!”
A couple of days later, and I cannot stop thinking about it, and looking at strap-ons and advice on the Internet. I like the one from a UK supplier that basically says: “if you are not sure about your looks with a strap-on, ask your partner whether you can blindfold him, so you do not have to worry about him looking at you. Plus he might find it sexy!”
I think I would!
I know that I will find out.
