After dating for a few weeks, it was clear this woman had some submissive tendencies that were not recognized by her. She typically responded to my gripping her hair, or holding her face firmly while fucking her mouth, by becoming tremendously excited. When we would talk about it, she was fairly assertive that she was not submissive – the suggestion that she enjoyed being controlled seemed unappealing to her. This was especially the case when it came to discussions about anal sex.
She had done it before and stated that she had no interest. Her experiences involved some pain and not much in the way of sexual arousal. Contrary to those sentiments, I had found that spanks and caresses of her ass cheeks and light fingering of her ass opening caused her to get very excited. It was as if the illusion of anal sex had appeal, but the actual act was unpleasant to think about.
One evening, I decided to be bolder and say that I was intent on teaching her to LOVE anal sex, and that her first lesson was going to be right now. Her response was to state back to me that she wasn’t interested – and that she didn’t want to try it. I obviously was not going to force her, and it appeared we were at an impasse. Then I stated what she really desired to hear.
“OK, let’s make a deal. Let me take the first steps using only my finger, and if it doesn’t thrill you, I will not do it anymore. And I mean THRILL you. if you do not cum because of my finger in your ass, then I’ll stop fingering you and not bring up anal sex again – deal?”
She was OK with that and allowed the experiment to begin. Her mind was made up though – she told me she wasn’t going to enjoy it and was only humoring me. That was the challenge placed in front of me. So, it was time to start the process. And that start began with her mind.
It was clear that she needed to learn that pleasure could come from the sensation instead of worrying about possible pain. Based on her submissive tendencies, my task was two-fold: I must do this painlessly, and I must keep her mind thinking of pleasure as I did it. If I did both of those tasks, she would enjoy anal.
First, she needed to be rewarded for her willingness. I started by slowly licking her pussy. I talked to her as tongue gently went to work. I gave her a mental image of what I would do with my finger shortly while I was pleasuring her. I wanted her experiencing pleasure while thinking about the words I said. I would make her cum a few times before I got started on her ass.
My tongue was gentle and slow as I slid it around her slit and clit area, making sure to slowly build-up her desire. My tongue occasionally flowed up and over the top of her clit as I continued the build-up. It wasn’t long before the long, slow, gentle tongue strokes I used began making her squirm. Her first orgasm happened as I started sucking on her clit firmly. The second when I inserted two fingers inside her while nibbling on her clit. She was very aroused and wanted more. I felt she was ready for my finger now.
I then lubed up my finger and placed it at her ass – softly caressing the entrance. I did not push in, but merely placed a consistent pressure against it while my finger caressed her. Then I started licking her clit again and continued talking to her.
“You know my tongue will make you cum again, right baby? You know you’ll make noise for me soon, don’t you?” And with that, I started tonguing her pussy like before – all the while having constant, but small, amount of pressure on her ass with my lubed finger.
“I won’t push my finger inside you. That isn’t how my finger will make it into your ass. You know how it’ll happen? Your ass will tell us both it WANTS my finger. You will crave my finger soon baby…very soon. And you’ll know because all by itself, without either of us trying at all, your ass will naturally open up to my finger. Without any effort, your ass will relax and let my finger go all the way in – as deep as it can go. You’ll see. Your body will WANT my finger deep inside it deeply. You’ll see…”
And then I licked her clit fast and firm. I wanted to make her cum again quickly. And she did. And as she came, her ass started opening ever-so-slightly. I was true to my word and did not push in further. I just keep the same slight pressure with my finger and waited.
“You see? No pain, Baby. None at all. Your ass is opening to me. It did it while you came. Can you feel it now? Can you feel that your ass is wanting my finger deeper? I’m not pushing. Ah, yes. Your ass is already inviting me deeper. Feel that? Feel how your ass is loosening up for me? That’s what I wanted. Just like that. And no pain. None at all. Am I right?”
As I spoke, she was still loosening up and my finger slowly entered deeper and deeper into her ass. I did not push at all at any time and she was starting to notice that not only was I right about there being no pain at all, I was also right that it was turning her on as it slide deeper. And, like a good girl, she told me so.
“God Jeff, this actually feels good to me. I NEVER thought it would feel like this. No pain at all, and I cannot believe it went in without you pushing at all. Amazing!”
When my finger was all the way in, I let it rest motionless so she could get acclimated to the feeling. Then it was time to get started on her having an orgasm with my finger in her ass. It was important that she cum with the feeling of something in her ass.
I started to make that happen by inserting a finger from my other hand into her pussy – deep. While keeping my finger in her ass still, I touched my fingertip in her pussy to the fingertip in her ass thru her membrane and let the pussy finger slide back and forth so she could feel the motion. She LOVED that sensation. So, I kept the rhythm going and slowly sped up faster and faster in her pussy until she came. Not hard, but she came. As she was, I used my habit of keeping the conversation going. Forcing answers verbally is a part of the mental aspect I was trying for.
“Oh, yes baby, that’s what I want. Cum for me now…that’s it…that’s what I wanted. Feel my finger in your ass baby? Feel it? It’s fully in your ass and you came. You like the feeling of cumming with my finger in your ass, don’t you? Tell me baby…you like it don’t you…”
“Yesssss…I liiiikkke..ittt…” she throated out as she was came. The emotional excitement in her voice as she tried to talk thrilled me.
Now it was time to get her to cum from motion in her ass. Once she had calmed down a bit, I told her I would keep my finger in her pussy still, and that it was time to move my finger in her ass – only she would be the one doing the movement. I would keep my finger in her pussy as deep as I could…but that I would keep my finger in her ass at the same location and SHE would move her ass as she wanted. If she wanted it to start sliding out, she should move that way, and if she wanted it deeper – just work it in.
It was awkward at first until we figured out how she needed to move, but we both got the hang of it. It was important that SHE be the one that moved and cause motion and not me. That way she had total control over her sensations. As she moved about, I asked her about any discomfort. and she always replied there was none. She kept saying how amazing it was to her that she was actually enjoying it.
Once she had done a few strokes in all the way and back out, I asked if she was ready for me to take over now. She agreed. And with that, she got her first finger ass-fucking. I made sure to keep my finger in her pussy in deep and pressed against her membrane, and then slid my finger in her ass back and forth fast and deep.
All of a sudden – without warning and for the first time in her life – she came from motion in her ass. The suddenness of her orgasm surprised both of us.
Afterwards, I told her that, so far, I had met my side of the bargain. Was she still willing to meet hers? She smiled as she said yes. She would let my fuck her ass.
And that is when I stopped. I didn’t touch her ass again for a few weeks. I simply talked nasty to her about it to build up the sexual tension.
After a few weeks, she started asking me if I was going to try and fuck her ass, but I never answered. She kept asking day after day – without the answer she expected. It obviously was on her mind a lot. I liked that.
Then one day, she just asked me for it. So, being a gentleman, I agreed – provided she properly “prepared for me.” I explained that I would know, for certain, that she wanted my cock in her ass if she arrived at my house having already lubed up. I’d know without a word what she wanted my cock for. Until then, I wouldn’t touch her ass.
The next evening, she came over again. I got hard immediately when she looked into my eyes and told me that she had prepared for me. I responded by telling her it was time for her to learn to enjoy my cock in her ass. I also told her that the first lesson would be very similar to the last lesson, and I was true to my word.
I started by placing the head of my cock at her ass opening instead of my finger. I kept myself still, merely applying pressure – and slight pressure at that. Then I put a finger in her pussy and started rubbing her g-spot, telling her again that I would not move my cock. I reminded her that, like last time with my finger, her ass would automatically open for me because it craved my cock. Her body wanted it in her ass. And again, like the last time, her body would tell her.
When she came on my finger the first time, her ass opened up a bit for me. As before, I kept still – knowing my head would pop inside her shortly. I didn’t push at all, and as I felt my head now inside her ass, I asked her if it felt OK. She said it felt, “different,” but that there was no pain at all. So, I remained still and kept up the slight pressure on her ass.
Over time, maybe 3 or 4 minutes, her ass opened up more and more, gradually allowing my shaft to slip deeper and deeper. I continued my talking to her as it was happening – causing her to moan out loud numerous times as she felt it.
“Feel that baby? Feel my cock sliding in? You love that already don’t you? You love that. I can tell by your breathing changes. I can hear in your voice the excitement for the feeling in your ass. Oh, you love this baby. Oh yes. Feel how deep it is getting in your ass now?”
When it was all the way in, I kept still. And like before, gave her ass time to get acclimated to the size difference in her ass. I said it would be up to her to move back and forth to start the ass fucking.
She was tentative at first, but gradually moved further and faster, testing if it was painful. It was not. Once again, she was amazed at the sensation and feelings she had. Once she had done a few strokes in and out deeply, I asked if it was time for her first ass fucking.
She said yes, and I fucked her ass long and deep. And she came. And she came again. And then a third time. On the fourth time, she let out a scream, so I slapped her ass hard while she came.
Then I told her, “This will be your favorite baby…you know that now don’t you? That this will be your favorite way to cum. You know that now, right baby?”
She replied with a deep, breathy, “Fuuucccckkkk Yyyeeesss.”