Chapter 8: Monday

When I woke up, my first awareness was of something going on down where my legs joined my body. It took a few seconds before I realized that there was a mouth on my cock. I pulled the sheet back far enough for me to see Jen’s curly brown hair kind of bobbing up and down where my cock would normally be found.

It seems that Jen has decided that we should spend this final morning together doing sex stuff. I was OK with that.

She turned her head so I could see her face, and she could see me. “Hi, Dave.” Then she resumed moving her mouth up and down my cock. She’d also mastered the milk-and-twist motion that we had practiced before.

“I put some coconut oil on your cock – I hope that’s OK?”

I managed to sigh that it was marvelous.

She took her mouth off me, although she didn’t stop with the milking motions.

“I was hoping we could start the day with you fucking my pussy. I’m sorry I didn’t ask first, but you were sleeping so nicely and, well, I wanted you inside me, so I thought that ... maybe you wouldn’t mind.” Here, she was simply putting me on. She knew that I wouldn’t “mind” in the least.

This was nice. This was different from the times before. This time, I didn’t have to think about “teaching” Jen, or being concerned about her reactions, and Jen didn’t need any teaching now. This was no longer a girl who was curious about sex and had an inappropriate crush on a wildly age-inappropriate man. This was a young woman who was taking both the initiative and the responsibility for her sexual pleasure, with a man she cared for. This time, she knew what she wanted, and what it was like, and how to do it, and I was able to just lay back and enjoy – to enjoy the experience of her warm mouth and her soft-but-increasingly-skilled young hands – and to experience the feelings she had toward me.

And Jen’s increasingly capable ministrations were having the desired effect on my cock. From first waking up, to the initial thickening, to a soft erection, to a serious hard-on, Jen was preparing her lover for the sex that she wanted.

She paused, to assess the situation, it appeared. She seemed pleased with results so far. In fact, her look was almost a look of approval, as if she were saying, “There!” to herself.

She raised herself from me and crawled up the bed to reach the little bowl of coconut oil that seems to have become a permanent fixture in our − our – bedroom. She dipped three of her fingers in the oil and made them into a cup. Then she carefully moved her cupped fingers to her pussy made sure a goodly amount of the oil remained there. Then she used what was still on her fingers, plus what was dripping out of her, to be sure that my cock was fully lubricated and ready to enter her without any difficulty.

Before she quit, she gave it a quick, firm squeeze and smiled at me. I smiled back.

Then, as we had practiced several times before, she spread her legs enough, centered herself over my cock, and lowered herself so the lips of her pussy perfectly enfolded my cock which she had so thoroughly, lovingly prepared. The touch of her soft membranes, with their coating of now-warm oil, was electric, and my cock twitched just from that first contact. I lay there and waited for her to go on.

She put her hands against my shoulders and shifted some of her weight onto them, then started to slide those slick lips back and forth on my slippery cock, sometimes using short strokes, other times, longer ones. Sometimes she would press against me, other times, she’d lift her weight a bit and just skim along the underside of my cock. Strangely, these light, feathery strokes aroused me more than the heavy ones. I think I could have closed my eyes and just ridden this sensations to a fine orgasm. But I knew that if I gave in to this temptation, I’d be cheating Jen – and myself – out of much more pleasure.

I was pleased to see that Jen had learned “the lesson of the clitoris,” and that she was making sure that her clit was rubbing along my cock for most of her strokes.

So, let me try to give you the picture. I am lying, comfortably, on my back, Jen’s weight – and sex – on top of me. My hands are on her hip bones, not so much helping her as simply riding along with her movements. My eyes are closed, for the most part, but now and then I open them, to look at Jen’s face, and to take her little breast puffs between my fingers or to put my hands over them and gently massage. She smiles when I do this. Also, her look is no longer one of concentration, or of concern over whether she is doing things “right,” as it was the first times. Now, it’s a look of pleasure, and confidence – and love.

And without asking, she decides that now is the time. She lifts herself up, then surely and efficiently lines my cock up with her pussy, moves it back and forth a few times with her fingers to get it seated in her entrance – and lowers herself onto me, taking all of me that she can into her in a single plunge.

The feeling is incredible. First, it is warm − so warm. And slick. And caressing. She is both caressing and tight. I reach around her shoulders and pull her down to me, and we kiss. And it’s warm, and soft, with a little tongue play, and a lot of nibbling lips, and then I let go and she sits up again and begins to ride me. She knows how to move her pelvis back and forth, and the rocking-and-sliding motion that ensures that her clit enjoys frequent contact. Feels pretty good to me, too.

I pull her down again, and I gently squeeze her bottom lip between my teeth while I reach back and grab the cheeks of her ass and squeeze – not hard, but firmly. While my hands are back there, I put my middle finger at the base of her pussy, to give her a little extra stimulation down there, but also the get it moist with her juices so I can slide, then massage, her sweet little asshole.

She moans a little moan, and she speeds up the sliding-rocking motion of her hips. Meanwhile, the feel of her puckery asshole on my finger tip sends something like a shot of electricity to my brain. I bring my finger to my lips and moisten it with my spit, then move it back to her ass to finger her even more. I do this again, but this time, I hold the finger in front of her mouth. She immediately moves her head and takes my finger, covered with the juices from her pussy and asshole, into her mouth, where she cleans it with her tongue, then leaves it with a fresh coating of her spit to lubricate her anus once again. This lewd act causes me to get even harder.

And with the thickening that comes from this, Jen’s feels even tighter – and also hotter − to me, and I get concerned that I might be hurting her young, still relatively inexperienced ... her cunt. I look in her eyes and ask, “Are you still OK, Hon?” She smiles. “OK. In fact, way better than OK.” A wave of affection – okay, love – seems to wash over me.

She says, “I think I’m ready ... I can cum now, Dave. Are you ready to cum?”

No sarcastic remarks this time. “Whenever you’re ready, my darling.”

She smiles again. Then she takes a hand from my shoulder and lowers it to her pussy and begins to stroke her clit with purpose. I watch her, for the cues. Closer. Then she closes her eyes and throws her head back. And then she makes a couple of jerks with her pelvis on my cock, and I know that now is the time. I close my eyes, tune out everything but the sensations I am feeling, put my finger against her anus one more time – and let myself go.

After my first two or three contractions, she falls forward on me, and I wrap my arms around her, and we lay there, holding each other as I feel the last of my jizz squirting into her. I don’t know how long she and I will be able to cum like this, me into her. Who knows? It might already be too late. We can deal with that. I know we can.

With her head ... her hair against my chin, her cheek lying against my chest, “Dave...”

“I know, my darling, I know.”

And then, “Are you hungry, Dave? I’m hungry.”

Yup, I’ve never had a relationship quite like this one – as honest and uncomplicated. And it dawned on me: that’s Jen. She’s a young woman who is extremely intelligent and observant, but whose mind is completely free of all the debris and pollution that most of us acquire over our lives.

I pulled on my “best” track pants and sweatshirt, and Jen once again put on the blue tights and red ski pullover. I think in truth she would have preferred to wear something fresh, but she knew how much I liked how she looked in those. Besides, she hadn’t spent that many hours actually wearing them!

We brushed our teeth – together, quietly sharing this simple act – and washed up a bit, and then we went out to the kitchen. I spoke first and asked Jen if she would make her scrambled eggs like she did our first morning together. She smiled, and then, unexpectedly, touched her hand to my cheek for a moment.

Now that she knew where things were, Jen got her preferred skillet and scrambled the eggs with customary efficiency, while I made coffee, toast, poured the juice, and set out butter and jam and Tabasco.

The eggs were perfect, of course, maybe even better than the first time, but we were kind of subdued. Jen talked a bit about school and seeing her friends and things she had to do, but it wasn’t with her typical enthusiasm, like her heart wasn’t really in it. I was silent, mostly, just acknowledging Jen’s remarks. We had to do something about this.

“Hey, I have an idea – let’s do some laundry.”

“Great!”

We cleaned up the breakfast dishes and utensils and headed for the bedroom to round up the various sweat clothes and other items we’d been lounging around in (during those times when we weren’t “otherwise engaged”) – plus the single pillow case that we had used during yesterday morning’s anal activities − and tossed them in a plastic laundry basket. Jen said, “Can you help me strip the bed?”

I stopped what I was doing. I thought for a moment. I said, “Maybe we could leave the sheets...”

Jen was puzzled. I sat down on the bed.

“I – I think I’d like to have ... how you smell ... around for a little while.”

It finally dawned on her what I was saying – not just the words, but what I was really saying.

She smiled sweetly at me and said, “Pervert.” Then she sat on my lap and put her arms around me, and we just held each other for a while. Then she kissed me on the tip of my nose, and we got up, grabbed the laundry basket (together), and headed down to the basement.

Of course, we didn’t have that much, but Jen separated while I measured out the detergent and softener. She put the first load into the machine and set the controls, pressed “Start,” and we headed back upstairs.

Jen took my hand and said, “Y’know, Dave, since all our clothes are in the laundry” (they weren’t) “maybe we should get back in bed for a while?”

How can you not fall in love with someone like that?

We shed our minimal clothing and slid under the covers (it was still January). As usual, it was Jen who took the lead.

“Dave, can you fuck me in the ass again like we did yesterday morning?”

Again, coming out of that shy stage quite nicely. Actually, I’m really proud of her, feeling comfortable with taking the initiative for her own sexual desires.

“Yes, I think we can. In fact, I think I’d love to fuck you in the ass again, just like we did yesterday.”

I almost went into hysterics when she replied, “Goody!”

But we both got serious after that. Jen lay on her side, ass against me, her top leg jackknifed upward. Once again, I used my finger to introduce a liberal amount of the coconut oil into her rectum and around her asshole, then a generous glob of the anesthetic hemorrhoid crème, which I lovingly massaged into her anus. Then back to the coconut oil, which I used to make sure my already stiff prick was completely lubed and slickery. Then, I put another dollop of the anesthetic cream on my finger and began massaging Jen’s anus, to get it relaxed and loose and ready for ... whatever.

“Dave – I think that’s enough – I’m ready now.” In other words, a genteel version of, “Stop fooling around, Dave, and stick it in me!”

With Jen’s head resting on my left arm as she bent herself into a hairpin position, I reached down with my right hand to guide myself in, but instead, I met Jen’s hand, which grabbed my prick decisively and rubbed it back and forth against her asshole.

I decided that maybe the best thing for me to do was simply provide the pressure and let Jen guide the process. And before I knew it, I heard a slightly pained, “Oh!” and the knob of my cock had popped through Jen’s sphincter and into her ass.

I didn’t move, still thinking that Jen would be the best judge of how things should go. I didn’t move, and she didn’t move, but then I felt her kind of squirming around, and I guessed she was trying to get used to the intrusion, or perhaps get a little feeling from moving it around inside her. Then, I felt her pushing back against me.

“Now, Dave, but go slowly, OK.”

I steadied us both by holding onto her hip, and she stayed stock still while I gradually pressed against her ass. Fortunately, there was so much coconut oil on my cock and inside her ass that there was no friction.

And it was incredible! My well-lubed cock, slipping through that tight ring, sliding along that incredibly warm, oiled channel, caressing my cock with its velvet lining every millimeter I moved. And holding my Jen.

When I was about half way in, Jen said, “Can we rest?” I just stopped, savoring the multiple sensations while Jen adjusted to whatever she was feeling.

Then, without saying anything, she began to move back and forth, and with each move, she took my cock a little bit more into her divine rectum. And she continued, until the point where I realized that my balls were nestled up against her ass. I was balls-deep in Jen’s ass!