Getting the Job Done

by Stacey Zackerly

  Then there were the one-night-stands I had picked up in a bar, usually near closing time. For the price of a drink or two, and maybe a little light conversation I ended up spending the whole night with those ladies. There was even the girl I met at an outdoor rock festival who gave me head in a portable toilet. I have no idea whether the music turned her on, or she was high on something, or she was just the kind of girl who liked to give strange men blowjobs in a Port-a-John. I never learned her name but I never forgot that BJ.

  As a man it was always taken for granted that you wanted to get as far as you could possibly go as soon as possible with any woman you had a shot at. It probably sounds crass and stereotypical but it had proven to be pretty damn true in my experience. A truly successful date for a man ended with him getting his dick wet. Obviously a lot of women operated from a different playbook, otherwise everyone would be fucking everyone all the time, and the world would probably be a much happier place.

  Of course it didn't really matter what other people did, or what they thought. If for some reason I found myself wanting to have sex with Brent than I should probably do it. I just wished that I had some female friends to discuss the subject with. I didn't really want to get a reputation as the apartment complex slut, and I didn't really want Brent to get the idea that I was looking for a boyfriend, and I knew that I should probably call the whole thing off. If you're worried about drowning it's probably best to avoid going in the water as much as you can. On the other hand a nice Italian meal, with someone else picking up the check, sounded very pleasant and appealing. Having paid for many a meal in my time I didn't feel guilty at all about perpetuating the old custom of letting the man pay. It was just a chance to redress the balance a little, as far as I was concerned.

  What to wear was another of those questions that plagued me. I tried to rack my brain and think about what women wore on dates with me but I had to honestly admit that it hadn't really made much of an impression on me, unless the skirt was unusually short or the top unusually low-cut. They seemed to always look nice and were incredibly well-groomed, unless they were going for the "fuck it, this is who I am, I don't need to impress anybody" look, which was of course designed to impress people by how "hip" and "genuine" they were.

  For a moment I thought I had stumbled on the secret by just trying to wear whatever I would have wanted to see a woman wear on a date, but I realized that would probably be a fishnet body stocking with nothing on under it and maybe some thigh-high boots or stiletto heels, so it didn't look like that was going to be a good rule of thumb to base my fashion choices on.

  If it sounds like I was sort of obsessing over this simple little date I definitely was. It wasn't just my first date with Brent, it was my first date as a woman, after all, and that seemed like kind of a big deal. Of course the more I stressed out about it the more likely it was that the evening wouldn't go well so I managed to calm myself down as much as possible and tried to just keep an open mind.

  I ended up choosing a red print dress with a black jacket over it, black handbag, black shoes, and sheer black stockings. The dress showed some cleavage, without showing too much, and it was a bit on the short side, but not too short. I actually felt kind of pleased with myself for being able to come up with something that I thought looked very nice and showed a bit of my body without looking like a truck stop prostitute.

  I was already pretty good at choosing and applying makeup and with my hair and nails done professionally I felt very pretty as I checked myself in the mirror one last time before Brent called for me. I found that I liked feeling pretty, which was something else for the notebook. Now obviously just about everybody likes to feel attractive, whether they're male or female, but feeling pretty was definitely something that I had never desired before. Being called a "pretty boy" was usually a very disparaging comment that implied that you didn't look masculine, which suggested that you were probably gay. Nobody had ever called me that, and they weren't likely to have done so, but if they had I would probably have kicked their ass. That would have been a major insult. Now I was quite happy to be pretty and hoped that Brent would think that I was too. Since he had already called me beautiful without seeing me all fixed up I was pretty certain that I had nothing to worry about in that department.

  The restaurant turned out to be just the kind of place I liked. It was kind of small, kind of old, kind of dark, and slightly shabby compared to modern chain establishments, but the atmosphere was warm, the portions generous, and the food fantastic. Brent looked very sharp in his sports coat and slacks outfit and I appreciated the fact that he had dressed up a bit for the occasion. People tend to be too casual these days I thought. It's nice to do some things where you look like you put some thought or effort into it.

  The conversation was basically a continuation of what we had started on the sofa and I tried to open up a little bit more. Naturally I still had to be careful about things since I had never done any typically female activities like selling Girl Scout cookies or being a cheerleader or anything like that and I guess Brent kind of picked up on that.

  "Sounds like you were a bit of a tomboy," he said with a smile as he poured me another glass of wine.

  "You could say that," I replied. "I think I sort of grew out of it."

  "Well I never would have guessed it based on the way you look now...so smart and sexy and feminine."

  "I was definitely a late bloomer," I said quite truthfully.

  "I love what you did with your hair, by the way."

  God this guy was good, I thought. He obviously knew a thing or two about women. He listened really well but wasn't shy at all about speaking up, was good with flattery without going over the top, and seemed totally relaxed, comfortable and confident. It was funny but I was definitely judging him more from the perspective of a man studying another man's technique than as a woman sizing up her date as a potential love interest. Maybe that was sort of a defense mechanism. My brain trying to remind me that I wasn't exactly what I appeared to be.

  I also found that the more we talked the more comfortable I became around him and yet the more nervous that made me because I felt my resistance weakening. He was good at getting me to laugh, or getting my pulse racing a little when he gave me a compliment. I knew beyond the shadow of a doubt that he wanted to fuck me, that he had wanted to fuck me from the day we met, and had been doing whatever he could to get me to the point where I wanted to fuck him ever since. I knew that men would do or say whatever they thought would work to accomplish that goal and figured that he had probably said exactly the same things to who knows how many other women he had brought to this place, or somewhere like it. I knew all of that but I also knew that I wanted him to touch me. I wanted to kiss him again. I wanted him to hold me. I could decide after that if I wanted anything more.

  "The night is still young, as they say, shall we keep the ball rolling?" asked Brent once we had finally left the restaurant.

  "What did you have in mind?" I inquired, knowing full well exactly what he had in mind.

  "Whatever you think. There's still time to catch a movie, or we could go for some coffee, or take a walk or something," Brent suggested.

  "You know I haven't seen your apartment yet. You've seen mine plenty of times but I have no idea what yours looks like. Maybe we could have a drink or something, unless you've got something to hide," I joked.

  "No I've already stashed all my dirty laundry under the bed and I'm not running a meth lab in there," he replied with a grin. "I'm sure I could scrounge up something for us to drink, although I seem to be missing two wine glasses."

  "We can always stop and pick them up on the way, if you want. We do live just down the hall from each other," I pointed.

  "I'm sure we'll manage without them."

  I was quite sure that he was correct about that.

  CHAPTER 5:

  His apartment was surprisingly neat and well-decorated, I thought. Not the typical bachelor pad. Certainly not the kind of bachelor pads I
had always lived in. Yet it was still masculine. There was no question that this was a man's apartment. It was just a man with a little taste who wasn't a total slob.

  Brent fixed a couple of drinks and soon we were chatting on the sofa again, although this time it was his sofa in his apartment and we had come here after being on an official date. That kind of elevated the stakes in my eyes. Whenever I got a woman back to my place that usually implied that she was at least open to the idea of fucking, and more times than not that's what ended up happening. I figured Brent had the same impression and I knew that I was going to be tested on it at some point.

  The kissing started pretty quickly. I don't think either one of us finished their drink, and I don't think we had a whole lot more small talk to get out of the way. He made the first move and I responded favorably. When he tried to put his tongue in my mouth I let him. Then I put my tongue in his mouth.

  It probably sounds pretty ridiculous to hear such mundane details about such a routine thing as two people kissing on a date, but these were all firsts for me and therefore magnified in their importance.

  I had taken my jacket off so my arms and shoulders were bare and he had a much better view of my cleavage. He hands found my bare skin quickly enough and I liked the way it felt. My skin was so incredibly smooth and soft compared to what I was used to. It also seemed more sensitive in a way. Someone touching my shoulder would never have seemed terribly erotic before, but it kind of sent a little shiver of excitement down my back now. And when he started kissing my shoulder, and then my neck, and then under my ear I got the distinct impression that I was getting turned on.

  It seemed funny to me that I wouldn't just automatically know whether I was horny or not. As a guy it was pretty much instantaneous and there was incontrovertible proof growing hard in my pants. Now I felt sort of like a car with a weak battery where you kept turning the key and thinking that it was close to starting but never really being sure until it finally turned over and you heard the motor running.

  I wasn't sure how to touch him. I know, I know, that must sound stupid, but I didn't really know what to do with my hands. I had made out with girls countless times in my life, but like their wardrobe choices I couldn't clearly recall all of the details from their perspective. I put my hands under his arms and on his back, and I sort of let my hand explore his chest a bit, and I got a hand on his thigh but I still hadn't moved to touch his crotch or anything.

  "We could go in the bedroom if you'd feel more comfortable in there," Brent suggested, perhaps sensing that I wasn't being quite as responsive as he might have hoped.

  "Okay," I replied softly.

  Brent escorted me to his room and I gave it a quick look around, just to be polite, but when I turned back to face him I was in his arms again and this time he was much more forceful. We had been kind of lightly touching and caressing but now he held me tight and pulled me close as we kissed very deeply. His hand got under my skirt and cupped one of my butt cheeks while his other arm was around my waist.

  Then, very casually, Brent took the straps that were holding my dress up and pulled them down, pulling the whole top of my dress down in the process. The dress had a sort of belt thing around the waist and I unfastened it. After a few shimmies of my hips I was able to make the whole thing fall to the floor, which felt like an incredibly sexy thing to do.

  He had taken off his coat when I did so while I danced my way out of my dress he took off his shirt. Now I was clad in my bra and panties and my thigh high stockings and shoes. Brent took me forcefully into his arms again and the kissing resumed.

  I'm sure I will have plenty to say about tits along the way but for now I will just comment that it feels kind of funny to have something that big sticking out in front of you while you're being embraced tightly. It was hard not to be aware of them. It was especially hard to not be aware of them when I felt my bra being unfastened and realizing that I was about to be naked from the waist up.

  At that point things moved pretty quickly so that we both ended up on top of the bed. I was down to my panties and stockings, and he was down to his boxer shorts. In a reclining position, with so much bare skin available, we did a fair amount of rolling around with our kissing and caressing.

  His hand got between my legs and started rubbing me through my panties, and I guess when I offered no objection he put his hand inside my pants and began to finger me. While that was going on below he was sucking my nipples up top. This was probably the point where I had no doubt that my motor was now running hard and strong. I actually admired the man for his seeming appreciation of the value of good foreplay. I confess that I have not always been quite so patient. When I was a horny man I was pretty much obsessed with alleviating that horniness in a timely fashion. I don't think I was a terrible lover by any means, but I do admit to having times where I was probably in too much of a rush to get inside the woman's box without worrying enough about getting into her head first.

  "Leave your stockings on," said Brent during a moment where his mouth wasn't full of tit. "They're incredibly sexy."

  I read a couple of things into that simple sentence. First, he was telling me, not asking me or even making it sound like a suggestion. Second, he obviously thought it was time for me to take my panties off.

  I wasn't terribly used to being told what to do in bed, although there was a girl named Shauna Marcum who kept yelling at me to stick a finger in her ass all the time. Of course that was always when we were already hot and heavy and a woman is more inclined to make demands like "faster," "harder," "deeper," and so on.

  There was still a little thought in my mind that maybe we could just do what we had been doing for a while longer and then call it a night but as I said before my motor was running pretty hard now and I had a feeling that neither one of us would be totally satisfied by just getting to first base, or second base, or whatever base we were currently occupying.

  I pulled my legs back, which immediately made me feel totally exposed and vulnerable, then wiggled my panties off and tossed them aside. Before I could put my legs back down Brent had gotten between them and he held my legs up by the thighs as his head disappeared down below.

  It was kind of a shock to realize how wet I was already, but my panties seemed positively soaked when I pulled them off. That seemed kind of creepy, like I had pissed my pants or something, but that obviously wasn't the case. I knew that my pussy would get wet when it was aroused, and I had felt it when I was masturbating, but I think the surprise was that I had gotten so moist long before Brent had even touched me down there. I guess my body was telling me that I was really turned on before my brain had totally gotten the message.

  Brent licked my pussy and I really enjoyed it. That's kind of a simple statement but having not had a pussy for long I had no idea if he was especially good at it or it just felt especially good to have it done.

  It must have been pretty obvious to Brent that I was as ready and willing as I was probably ever going to be because he suddenly stopped licking and yanked his shorts off rather quickly. My legs were still in the air, even without him propping them up, and he hurriedly scrambled to get between them again but for an obviously different purpose.

  "Let me see it first," I suddenly blurted out.

  Brent gave me the biggest, most wicked grin I had ever seen as he came over and kind of gently sat on my stomach. His dick was of above average size, I would estimate, though probably not bigger than my own had been, and it seemed terribly hard and was kind of twitching a little as it pointed straight at me.

  "Do you approve?" he asked rather proudly.

  I found myself reaching out and touching his cock with my hand. It felt incredibly warm and it was definitely throbbing. It didn't really freak me out to touch it, perhaps because I had touched my own so many times. What did freak me out was the idea that he was about to put it inside me...and that I actually looked forward to that happening.

  "Not bad...not bad," I teased. "Now let's see what you ca
n do with it."

  CHAPTER 6:

  The first thing Brent did with it was put it in my pussy. I had received instruction on masturbating technique and I felt that I was a fairly accomplished practitioner by this point, so I knew what a penis shaped object would feel like when inserted into my vagina. What I didn't know was how radically different it would feel to have a real penis inserted into my vagina by an actual living human male. Cock + Pussy = Fun was a fairly well-established equation, but I never would have guessed how much fun it could be for the one with the pussy.

  I seemed to be making a very strong case for the argument that said that even a totally straight male would find it possible to tolerate, or even enjoy having sex with another man if his body had been "hotwired" to think it had always been female. I was still conflicted, there's no doubt about that, but it had been a surprisingly easy path from the idea of being totally repulsed by the thought of ever touching another man in an intimate way to pulling my legs back and accepting his cock inside me. And in all honesty my apprehension had probably been more from the fact that I was technically a virgin and didn't know what to expect.

  As I looked at Brent, straining away as he pumped me between my legs, I thought he looked rather sexy. He wasn't terribly well-built, or anything, but he was fit enough. In the construction business I was used to being around some pretty muscular, hard body type men, often with shaved heads and tattoos, just like the stereotype you might imagine. I had been pretty buffed out myself.

  Brent didn't seem like the kind of guy who would be shirtless, in a hardhat, swinging a hammer on a roof in 100 degree heat, but I thought he might look kind of cute doing it. He was certainly starting to work up a sweat as he hammered my pussy, but I really didn't think a hardhat was probably necessary, unless he had some really crazy shit in mind that I couldn't even begin to imagine.