Chapter 2

It felt odd to be figuring out what to wear before going out to fuck Jennifer. It had been a long time since I’d dated, and even then, however optimistic I might have felt when the night began, it’s not like I ever knew with 100% certainty that a first-date would end in a home run. The thought put a spring in my step as I met Jennifer in the hotel lobby. Her mood, by contrast, appeared tense—she avoided my gaze, and bit her lower lip as I walked over to her. Was she having second-thoughts? Beforehand, I had guessed she would feel honor-bound to pay for the room, since I was doing her a ‘favor’; but now (whether from shame? distraction? fear of discovery?) she didn’t offer to. Instead, after an awkward greeting and moment of silence, I headed over to the reception desk, while she remained by the elevator. Key acquired, we rode up without speaking, unlocked the door, and went in.

Jennifer had dressed for the evening in a dark wool business-suit, with a knee-length skirt, and antique-white boat neck blouse. Her attire pointed toward a cautious, rather than seductive, mode of engagement on her part, I thought. Still she looked stunning. She opened up her purse and took out a bottle of lube, setting it on the bedside table. Then she put the purse down and stood next to the bed, hesitant, looking at me. I returned the gaze. She seemed unsure what to do next.

After another awkward pause, I figured I would have to be the one to initiate physical intimacy. I moved over and embraced her. Her body was stiff. I ran my fingers through the back of her hair, stroked her back, and then shifted position in order to kiss her. Her lips met mine, just for a moment, and then she pulled back, clasping our hands together in front as she detached herself from the embrace. “James,” she said, with a tone of husky, muted determination, “I think it’s really important that we keep some boundaries here ... So neither of us gets confused. We have a thing we need to get done, and I think we should focus on that.”

Now I thought I understood what was going on in her mind a little better. Clearly she was trying not to think of me as a romantic partner, or this as an erotic liaison. As such, it was important to her that this affair remain businesslike, that I stayed firmly in the category of ‘friend,’ and (most important) that she could tell herself with conviction that she was not cheating on Pete, not really. “Of course Jennifer,” I fudged, “we both understand that we’re not here because of anything improper between us. We’re friends, and the reason we’re here is to help you with your marriage and with getting your family started ... Really, if you think about it, it’s no different than if I was your doctor, say, or a therapist ... So ... as a friend who’s here to support you ... how would you feel most comfortable doing this?”

Without saying anything she released my hands and stepped back a few feet. “I’ve read that, um ... you know, from behind, is the best for fertility. So I think we should do it that way.” In her mind, apparently, this cryptic pronouncement was enough to clear up any remaining confusion. And so, with that said, she began undressing, following a cadence that was more functional than alluring. She kicked off her flats and unbuttoned her jacket, sliding it off her shoulders and folding it over the back of a chair. Next she unzipped her skirt and stepped out of it, folding it atop the jacket. Where her crotch peeked out below her blouse, I caught a glimpse of cream-colored silk panties—elegant, but not revealing. Even underneath, it seemed, she had dressed cautiously, desiring to appear attractive and professional, but not suggestive or overtly erotic.

Then, sans formalitè, she stepped right out of the panties, and there was the pussy I’d been fantasizing about for a good three years. It was well worth the wait. On one key question, if I had ever had any doubts, they were now dispelled: she was a natural blonde. Granted even on top she was a dark-honey hue, and then a shade deeper at her crotch, but still undeniably blonde. She had trimmed her pubic hair but left a substantial wedge in place—a delightful thatch which beckoned me to run my fingers through it, and brush my face against it. She stood there with her knees together. True to her farmgirl appearance, her thighs were not slender and spindly, but rather well-built and muscular. Sadly, this meant that, for the moment, most of her pussy remained shut away between them. Still, with the arrow of her pubes pointing the way, my cock took comfort in the knowledge that it would be getting acquainted with her hidden depths before very much longer.

Her next move shocked me—all the more so because her manner of undress, up to this point, had been about as modest as was possible under the circumstances. As I was still just beginning to unbutton my shirt, she turned, and without looking at me, knelt on the bed, and went down on all-fours, legs slightly apart, ass facing the side of the bed nearest me. My God, she was being direct about it! This was taking businesslike to the extreme (not that I was complaining). One minute we had been colleagues and friends, and the next she had gotten down on all fours and opened her cunt to me like a bitch in heat. Like a farm animal, docile and waiting to be bred. My cock had been on a bit of a roller-coaster ride—stiffening when we embraced, shrinking slightly when she pulled away, engorging at the site of that enticing hint of pussy. Now it was rock-solid. I don’t think Taylor had ever revved my prick up quite so quickly and completely (though I can’t say it was through any fault of hers).

I shrugged off my clothes in a blur—shirt, tee, shoes, slacks, socks, boxers. As I struggled to disrobe, Jen remained there on hands and knees, looking toward the far wall, pussy on display, waiting patiently for my cock to enter her. Before approaching, I gave myself a beat or two to capture a mental image that I could later replay. Like her thighs, her ass also had a little meat to it, and her hips were wide, giving her a delightful rounded heart shape from behind. Her skin down here was a pearlescent white, a few shades lighter than the antique-white of the blouse draped over it. The shirt did cover her lower back and a good bit of her ass, but beneath the blouse’s hem, her pussy was well and truly on display. One of the sorrows of monogamy is not getting to enjoy the full diversity of female genitalia. I marveled at how different Jen’s folds and curves were from Taylor’s (and yet both so irresistible). Jennifer’s ample pussy lips and clitoris were a succulent ruddy-red with earthy undertones, which coordinated well with the freckles on her face and arms. Despite her accessible posture, her pussy remained closed. Still, she did seem to have a large clit, since a fair bit was sticking out between her lips. Good, I thought, that will give me something to work with in getting her aroused.

One thing was bothering me, however, which was how much of Jennifer’s body remained covered up by her top. “Jennifer,” I put in, quietly, “I’m a little worried some semen might get on your blouse. We don’t want to leave any traces—maybe it would be safer to take that off.” This logic apparently made sense, so she got back up on her knees (damn, I did hate to miss even a second of that rear-view) and, unzipping the back, pulled it over her head and laid it on the pillows at the top of the bed. Her ivory-silk bra matched the now-discarded panties.

From behind, Jennifer’s midsection appeared trim, her back strong and straight, her skin pale and smooth. Jen’s shoulder-blades traced delicate lines, and below them the ridge of her spine was just visible. I tried to scope out her breasts as well as I could from this angle (it’s amazing how one can know a woman for years, and still have important questions about the exact size and configuration of her bust). In Jennifer’s case, it appeared that although her tits were not what one would call large, they did have a pleasing bit of heft to them. As she lowered back down on all fours, I got at least a glimpse of how they dangled within the cups of the bra. I desperately wanted to get her out of that bra, but I didn’t want to push my luck. And, after all (I reminded myself), I was about to plow my dick into this woman and impregnate her, so I really shouldn’t quibble too much about the details, should I?

“OK, I’m ready,” she said quietly.

I approached her from behind, laid my hands lightly on her hips, and maneuvered her closer to the edge of the bed, so her feet hung off. Personally I would have loved to stretch her pussy apart and impale her on my cock, right then and there. I probably would have cum in about five seconds. But even I was sensitive enough to grasp that a more subtle approach was called for. So instead, I laid one hand on her ass, and reached between her legs with the other. She gave a barely-perceptible flinch at my first touch down there. It didn’t take long to confirm that she was not, in fact, at all ready. Her pussy remained closed up tight, and as I nudged my index finger gently between its folds, she was dry. Clearly matters thus far had been entirely too businesslike.

“Jen,” I said softly, “we won’t be able to make a baby if your body isn’t prepared, so I’m going to help get you ready. Remember that there’s nothing wrong with what we’re doing. It’s no different than when you have a medical examination—there’s nothing immoral about that. And we’re doing it all for the well-being of your family. So just relax your body and let it respond ... OK, I’m going to start by massaging your back. As I do, think of Pete. Imagine that it’s Pete’s hands on your back.” Personally, I would rather have eclipsed Pete in her mind at that moment (just as I would soon be eclipsing him in her womb), but I figured thinking of her husband would help assuage the feeling that she was being unfaithful, and calm her distress.

To reinforce the words, I slid my hands upward along her back toward her shoulders. Without replying, Jen lowered herself prone on the bed, her feet and shins hanging off, arms at her sides. Her face was turned away from me. I don’t know what she was thinking, but my guess was that she felt a certain amount of relief. Although she had been trying to maintain a kind of symbolic fidelity to her husband, I’m sure she also understood that the kind of sex she had planned would have been cold and impersonal, and probably painful. I think she was grateful to me, therefore, for taking charge and sparing her the emotional cost of such a remote and transactional coupling.

I would have liked to have some lotion for her back, but I hadn’t planned that far ahead. I figured that using the lube for this would probably be weird. So I just massaged her muscles gently, letting the touch of skin on skin work its magic. I kneaded the tense knots in her neck and shoulders. I pressed my palms against her shoulder-blades, and moved them with a slow, firm, rhythmic circular motion, first outward and down along her upper arms, and then back toward her centerline. Little by little, I let my fingers and thumbs walk southward, toward her lower-back and the pleasant rise that ascended toward her ass. Just before the massage descended to undeniably sexual territory, I switched to her legs, and started the return journey, slowly massaging my way upward from her calves, until at last I was caressing the backs and insides of her thighs to within a couple of inches of her pussy. I could sense that Jen’s body had become much more relaxed, and could almost hear her mental conversation as she prepared herself, physically and mentally, to take me inside.

Without saying anything, I pressed gently but unambiguously against the insides of both thighs, and she parted her legs slightly. Now I did doused my fingers with lube, and gradually inched them into the gap thus revealed, gently and slowly massaging her inner thighs, ranging tantalizingly close to her pussy without yet touching its outer folds. Not wanting to break into her inner dialogue, I continued to work silently. Evidently things were moving in the right direction, as her labia and clit were becoming puffier and redder, and the lips themselves had begun to relax and part slightly, with a sheen of moisture visible.

These cues suggested that it was finally time to engage her in a more overtly sexual mode. I began by moving to the creases of her thighs, allowing my fingers to dive ever deeper between Jen’s legs, and to brush gently over her pussy lips, just now and again. Then, slowly and gently, I pried her open slightly, and began running two fingers along the soft inner surfaces of her labia, first on one side and then the other. Although lube remained necessary, Jen was at least a bit wet, and her flesh seemed willing to respond. I stroked her clit for a while, tracing tender but assertive circles with a gradually increasing pace and pressure. Jen’s sensitive skin responded to the touch, and her breathing became audibly heavier, as I worked to overcome the inhibitions of her mind using the sensations of her crotch. Sensing success, I began to caress the folds of her pussy with slow-building intensity, spreading it open and preparing it for my prick.