Chapter 2

From that day forward, Lindsey and I get together as often as circumstances permit. Also from that day forward, Lindsey has demonstrated that her difficulties in having orgasms have completely disappeared. In fact, when we’re together, almost anything we do brings her to at least a mild orgasm. If I kiss her neck or nibble on her ear, she trembles in a telltale way that says she is coming. Caressing her arm or the small of her back produces a similar result.

We have also experimented in every way we can think of – and the result has uniformly been fantastic. Hmmmm – there’s that word. Does this sound like a fantasy to you? I don’t blame you if you are having such thoughts. But it’s all true. There is a recurring fantasy that I have regarding my darling, sexy Lindsey. If this story leads in that direction, it will be clear when I am departing from simple recital of actual events into the realm of fantasy. But unless I tell you a scene is a fantasy, you can accept it as being quite true.

For now, though, there is plenty in my memory that interests me – and that I hope will interest you as well. Here is a memory from fairly early in our relationship.

At least a third of the time, the first insertion of my cock into Lindsey’s willing and eager pussy follows her swinging her leg over me, straddling me and sinking down with her pussy engulfing my cock. She will stay with this cowgirl position for a long time, sometimes moving her body up and down so that my cock slides in and out, sometimes rubbing her clit forward and backward against my tummy (or actually against what is called my pubic bone, which is apparently a bit more prominent on me than on most men – or maybe it’s just that I have less flab there). Or she will vary the forward and backward movement with circular or side-to-side movements. No matter what she does, she orgasms almost continuously, or at least with one orgasm following rapidly upon another, though with varying intensity. While she is doing that, my hands are in fairly continuous motion, caressing her arms, her thighs, her breasts or her tummy, squeezing her nipples hard the way she likes, or inserting a thumb against her clit to give it a pressure that even exceeds what she is able to achieve by pressing it against my pubic bone.

The fact is that she enjoys any position so thoroughly that it is hard for her to get motivated to change it. What used to happen pretty regularly was that Lindsey would continue in the cowgirl position for such a long time that she would start to get cramps in her thigh muscles. So, upon sensing that such a cramp might be imminent, I will initiate a shift.

The shift on the particular day that I am remembering at this moment involved pulling her upper body down on top of mine so that her breasts were pressed against my chest, and straightening her legs so that they were alongside mine. The advantages of this position are numerous. I could kiss her mouth, her neck or her ears. I could caress her shoulders, her back or her ass. I could grab her ass and press her body against my groin. So it’s a delightful position in many ways, even if it results in less penetration than the straight cowgirl posture permits.

While we were in this position and I was caressing her ass with both hands, I noticed that her ass cheeks were spread wide. This seemed to invite me to caress the area between her cheeks, which I proceeded to do, moving my fingers in circular caresses closer and closer to her asshole. When my fingers finally reached that spot, which was lightly lubricated by pussy juices that had spread there when she was in cowgirl position, Lindsey’s moans and pants accelerated and took on new urgency. The level of her urgency increased even more when I inserted one finger a half inch or so into her asshole. So I pushed my finger further in, about three inches or so, and then slowly slid another finger in, meeting with some resistance from the tightness of her sphincter muscle, but also producing clear indications from Lindsey, faster movements and louder moans, that she was enjoying this new kind of penetration of her body.

After continuing a little while like this, I said to her, “Next time I’m going to bring some KY and fuck you in the ass. Would you like that?”

Her reply was a quietly whispered “Ye-essss.” She sounded shy and demure, as if in wonder at her own temerity – or perhaps at mine. But it was clear from the way she now rotated her ass around my two inserted fingers (and at the same time her clit against my pubic bone) that she was excited by the prospect of having her asshole penetrated by my cock.

The next time we were together, I brought a tube of KY and put it on the bedside table. Lindsey’s eyes widened when she saw it; but otherwise she didn’t react at all.

We started out, as we usually do, holding each other close and gazing into each other’s eyes. I lightly kissed her neck, and felt her quiver with the first of the many orgasms she would have before we finished that day. I then nibbled on her earlobe for a bit, then thrust my tongue into her ear, which made her gasp and quiver some more. I had grasped one of her nipples between thumb and forefinger and now squeezed hard. At this point, Lindsey’s gasps, moans and panting told me that her orgasms were increasing in intensity. I took her other nipple in my mouth and sucked on it hard, then moved my back teeth over her nipple and chewed it lightly, while continuing to squeeze her other one.

Lindsey’s tummy is an erogenous zone that produces sensations almost equal to those she experiences from stimulation of her breasts. She had been having medium orgasms from my sucking, nibbling and squeezing her breasts. Her orgasms continued at the same level of intensity when I began nuzzling, kissing, licking and lightly biting her tummy. Meanwhile, her legs were spread wide, opening the way and inviting attention to her pussy. While continuing to kiss and nibble on her tummy, I began caressing her thighs near her pussy, and then laid my flattened fingers over her pussy and pressed downward, stimulating her entire pussy while not penetrating her at all.

At that point, the intensity of Lindsey’s orgasms increased and she began to moan and pant. She also reached to grab my cock and began rotating her body to try to get her mouth on it. I rolled onto my side and moved my hips toward her mouth to make it easier. She rolled onto her side as well, then lifted her leg to allow access to her sweetest spot as I made a trail of kisses and light nibbles from her tummy to her hip and then to the vicinity of her pussy.