The Best Job Ever Part 2. (M/F) | 2016

For anyone wanting to read part one, it's right here

Just to give a little more info now, I'll introduce the key players, as I won't be referring to them by name too much in the story. All names have been very slightly altered to keep anonymity. Again, primarily because I am still fucking around with those involved and I really don't want to get fired.

Me: Micheal, Mike or Mick (whatever you want, I don't care). I'm 28 (at this point, actually 32 now) 5'11" and very very black. Originally English, but now living in the US.

My Boss: Rob, a fairly typical old money rich jewish guy living in Nassau County, LI.

My Bosses Wife: Marilynn, 41 years old at this point, Blonde, blue eyes, very curvy, a good solid C cup (fake, but still fucking great). A true bored Jewish housewife.

So, with that out the way I'll carry on. This was really the true beginning of the "relationship" that still continues to this day.

It had been around 4 1/2 weeks since the office party, new years had been pretty uneventful. I ended up spending it with my friends in Freeport, NY. I hadn't heard from Marilynn at all so I'd figured that it was just a one off thing when she was drunk as fuck. However, over the course of the week, leading up to my boss leaving for a weekend conference, I discovered from him that she had just got another parking ticket on her Mini (They had 4 cars overall: He owned a white Escalade and a jaguar, she owned a black Escalade and a mini cooper. All cars were insured on the company policy so I was cleared to drive any of them in a pinch),decided to not pay it (again) and had had her license suspended (again). He asked me if I minded running her around over the course of the weekend and that I could use the Jag if I wanted. I figured, what the fuck, I got to borrow his Jag for the weekend and could, at a push, use it to cruise for pussy with a couple of my boys.

That night he ran me back to his place from work so that I could pick up the Jag. He made me promise that I wouldn't take it back to Queens, so I had to stay with my friends again for the weekend. At around 7pm I got a text from a number that I didn't recognise. It turned out that it was her, telling me that she had Yoga with her daughter at 9.30am Saturday morning and that I had to get them at 8.45 am, so my plan of going out with the Jag was shot down before it even started. I basically set out to get a good nights sleep and get up early the next morning. Sometime later, after I got out of the shower, I got another text from her. Telling me that she wanted me to take her out on Saturday night too, she had booked a table at a restaurant that her friend owned and that it was cool and that my boss wouldn't find out. I was apprehensive, but knew I had to go along with it as she had me over the proverbial barrel after the car incident a month earlier. I replied with a simply "ok" and "see you at 8.45" before deciding to get an early night.

I woke up around sometime around 7 the following morning and made sure that I was to their house by 8.35 (a simple task as they only lived in the next town). I text her to let her know that I was there and she told me to come in and get a drink, as they weren't quite ready yet. I went inside, was amazed at how fancy this house was. She shouted down and told me that the kitchen was to the right and to make myself comfortable, so I went in and got myself a water from the fridge and waited at the breakfast bar. About 10 minutes later I heard them coming down the stairs and into the kitchen. To say that the view was a treat would have been an understatement. She was wearing black, cropped yoga pants, pink and white sneakers and a black and white sports top that really squeezed those C's into a nice shape. I also had to admit, for a 41 year old woman she had a fantastic body, although I had to assume that there was some moneys worth of work that had gone into getting it that way. However, what caught my eye was the girl who followed her into the kitchen.

She introduced her to me as Paige, her eldest daughter (at 19 at that point). To say Paige was stunning was an understatement. She had matching blonde hair and blue eyes, just like her mother. However her hair was pin straight and down below her shoulders. She was wearing the same cropped style yoga pants and a pink and black sports top. In her case I could very easily make out the outline of her nipples through the sports top and the yoga pants showed off her ass perfectly, even though it wasn't too "in your face". She had a perfectly flat stomach which really helped to show off her figure. I greeted her politely with a handshake at this point (didn't want to kiss her on the cheek at the first meeting, not cool to overstep boundaries, especially with her mother there). I finished my water off quickly and told them to get ready.

I don't recall a lot about the drive, as it was pretty uneventful. I learned a lot about Paige, how she was a raw vegan and had been since she was 17 (explained her figure much more). She was currently going out with a guy (can't recall what he did or his name though) and she was the eldest of the 3 girls that they had. She was a college dropout who was trying her hand at graphics design. I dropped them off at the Yoga place and said that I'd get some breakfast and wait for them. As they walked into the studio I remember snapping a picture on my phone and sending it to my friend just to show him what kind of day I was having before heading off to get some breakfast.

I picked them back up at just after 10.45 having been made to wait for an extra quarter of an hour as they talked shit with some of the other women in the class (a class that made me seriously consider taking up yoga, so many fucking MILF's it was unreal). Once they got back in the car I took them back home. Paige headed upstairs right away whilst Marilynn stayed downstairs in the kitchen with me. As soon as Paige left the room and was out of earshot Marilynn changed her attitude right away, back was the flirty MILF that i'd first met in the Escalade a month earlier. She flat out told me that she'd been thinking about when she'd get a chance to get at me again. I was understandably nervous, being in my bosses house with all 3 of his daughters upstairs, but I felt that familiar tingle in my cock as I had done previously in the car. (It should be noted, I had never been around a woman who was so direct and so to the point as Marilynn, I definitely found it a huge turn on to have this woman actively telling me how much she wanted to get her hands on my dick again). She told me to make sure that I was on time for dinner and that it would be worth my while. Unable to restrain myself from saying something I simply asked her "yeah, how?" She gave me a smile and just started to walk out of the kitchen, as she reached the door she pulled the back of the yoga pants down enough to reveal her arse, displayed perfectly with a little black thong, before leaving the room telling me to make sure I wasn't late.

When I got back to the car I text my boy again, telling him what the fuck just happened and then drove the Jag back to the place I was staying. The rest of the day kind of blurred past as I was supposed to meet her at 7 for an 8pm reservation. About a half hour before I left I got a text from her, one that I still have to this day, that basically included a picture message of her dinner attire (tight black dress, cut low at the front with an open back) and a very direct message to make sure that I clean my dick thoroughly. Again, I had to show my friend before heading out. I made sure to stop and gas up the Jag before heading over there as I didn't want to run the car to empty, especially if I was going to be railing the guys wife in there before the night was out, that's just rude. I got to her just after 7 due to a line at the gas station, she met me at the door. To say that she looked amazing in the dress was a given. It held onto every curve perfectly and she wore this little silver chain around her neck that had a section that draped down between her tits. It's tough to explain, but I could have got hard just from that alone. This woman knew how to dress to impress. She paired it with perfectly applied makeup and those manicured nails again that I recalled so well. I did get told off about being late and how she didn't appreciate being left waiting (I was literally about 3 minutes late). I apologised as I did the gentlemen thing by opening the door for her, as she got it she just casually grazed her hand over my crotch before letting me close the door.

The drive was uneventful (surprisingly) she didn't talk much, other than to tell me directions and every now and then ask me a question about my past in the UK). The restaurant was pretty fancy, we got a table toward the back and the food was excellent. Halfway through the dessert she told me that she had neglected to put any underwear on under the dress. Well, I could swear that someone put a viagra in my drink, because I was instantly hard as a rock. Once we finished dessert she paid in cash and gave me a smile, told me that she was going to the bathroom and that I should go myself before we left as it was a long drive back. I told her that I was ok, as I'd only had water (remember the no alcohol lifestyle choice) but she told me that I really should go. With a shrug I figured what the hell and followed her lead.

It turned out that this place had those single bathrooms as opposed to a room with a couple of stalls in each. So it was basically 4 single stall lockable bathrooms upstairs from the main dining room. When we got up there I headed for an empty one, figuring she would do the same. However she jammed her foot against the door as I began to close it, stepped inside and then closed the door behind her. Now I think it is important at this point to make mention that I am no virgin, or a girlfriendless nerd, I've had a lot of GF's in the UK prior to moving to the states. But this entire thing had my heart beating a mile a minute. Wordlessly she grabbed my belt and unzipped my pants. This time however there was no fumbling around, she grabbing my dick right away, gave it one little stroke inside my pants and then pulled it out, stroking the underside with simple backward strokes of her hand. This was also the first time that she kissed me. She certainly knew what she was doing. The kiss was perfect, perhaps one of the best people i've ever kissed, and she did the little thing at the end where she bit my bottom lip. Between that and the hand around my dick I was already halfway to takeoff. She kissed me again, this time I kissed her back too, a little less shocked. I hiked up the dress a little at the bottom, enough to allow me to get my hand up, I had to check if she was telling the truth. My fingers found a perfectly trimmed pussy, already a little moist. She gave out a little half moan, half shudder as I touched her and broke away the kiss. She told me that she hadn't had a man touch her there in over a year, including her husband. Now it was my turn to smile as I simply extended my middle finger out, rubbing it along her pussy before applying a little pressure and forcing it inside. She wasn't the tightest I've ever felt, but for someone who had birthed 3 kids naturally she was definitely tighter than I expected. She gave out a kind of half cough/grunt as pushed it in. I actually stopped to make sure she was ok, to which I got told to "not fucking stop". So I obliged and gave her as much as she could take. Within a few moments she was letting out these little sighs and moans, trying but failing somewhat to keep jerking me off. I didn't care though, I was already hard as a rock from the situation, her hand was just the icing on the cake. I could feel her getting wetter and wetter as I fingered her, every so often she would tell me "right a little" or "left a little" followed by a slightly louder groan. She hand one hand on my dick, the other resting against the sink, keeping herself up.

I have no idea how long this lasted, it felt like an age, but it likely wasn't, but she eventually grabbed my wrist with the hand that was originally on my dick and made me stop. I obliged and pulled my hand from between her legs. I could feel her juices on my fingers. She then used both hands to hike her skirt up around her waist and turned, placing both hands on the sink, presenting her ass to me, telling me that I didn't need a condom as she had her tubed tied after the 3rd child. By this point I was in do or die mode, and I certainly wasn't dying so I grabbed my dick by the shaft and let it to the holy land. Now, saying that she didn't feel too tight around my finger was definitely different to my dick. As soon as I pushed the head inside it felt like a tight, warm velvet glove around my cock. She let out a pretty loud groan and her knees buckled, causing her to lean down more against the sink. This actually helped as it gave me a better angle. We fucked like this for, in reality, probably only 4-5 minutes. She definitely knew what she wanted as she was kind of rolling her hips back against each thrust, making it go a little deeper each time. She came faster than I've ever seen a woman cum and much, much harder than I've ever felt too. It took everything within me not to bust my nut inside her when she came, but right after she slide herself off of me and immediately went to her knees, finishing me off with a few strokes of her hand and that perfect mouth again. This time however, when I came she didn't splutter, she took it all with a smile.

Afterward, she wiped herself down between her legs with toilet paper and then straightened up her skirt, checked her hair and reapplied her makeup again whilst I cleaned myself up and zipped myself away. She took the car keys and left the bathroom first and then I followed a few moments later. When I got back to the car she was sitting in the passenger seat waiting to go. We drove back, making small talk for the most part, she mentioned how she would speak to her friend tomorrow to make sure that Rob didn't find out that I'd take her for dinner (she made no mention of the bathroom incident, so I figured that was our secret. At least until now I guess, sorry Marilynn :) ). When I dropped her off at home she gave me a kiss in the car before getting out. She told me to keep and eye on my phone and that she would be in touch again. Then she got out and went into the house.

I drove the Jag back to my friends house, and was stopped by Nassau County Police on the way for driving whilst being black (it's a 1 1/2 mile drive and they got me during the 1 part where I didn't have a white person in the car). Unfortunately, this is something that would come back to haunt me about a month later, but again that's another story for another day.

TL;DR My boss left me to drive his old lady around for the weekend whilst he was away on business, she had other plans and made me a better offer.