The Best Job Ever Part 4. (M/F) | 2016

For anyone wanting to catch the previous parts here is Part 1 and Part 2 and Part 3

To clarify, I have a lot of detail in these as I am able to elaborate from the original private online journal entries that I was creating at the time, that really helped me remember details about major events. From the point that I began working for them I became very close with my boss and did a lot of personal IT things for him too (such as building computer, setting up TV's, cable boxes etc) so I spent a lot of time at their house and got to know the entire family really well and saw the kids grow from teenagers into adults in most cases.

Here are the key players, as before, names have been altered as there are still things taking place at this point.

Me: Micheal, Mike or Mick (whatever you want, I don't care). I'm 29 (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.

My Bosses Eldest Daughter: Paige, 20 years old, 5'7", around 110lbs, Blonde, Blue eyes like her mother. College dropout and a health nut, very trim and in perfect shape, a solid B at an estimate.

My Bosses Middle Daughter: Lindsey, 18 years old (only just at this point), 5'1", Jet Black dyed hair, bit of an emo kid, about 115lbs, nicely curvy in all the right areas.

My Bosses Youngest Daughter: Mehgan, 15 years old.... I ain't no Pedophile, enough said.

We'll pick up in July 2010: After kissing me outside of Dunkin during a moment of god knows what Paige kind of avoided talking to me at work for a few days. Which was very difficult as we were wrapping up the project for a client at the time. I still had to finish the coding, but she had just about finished the GUI for it. I hadn't really heard much from Marilynn either after our last encounter, I was too concerned as she usually let me alone for a week or so after we met up. I discovered, from the owners son (who had been tasked with telling everyone) that my boss was throwing the annual July 4th summer party at his house this year and that everyone from the office was invited, being a complete masochist I figured that it wouldn't be awkward in the slightest to be around his wife (the woman that I was regularly banging ), his eldest daughter (who had previously kissed me) and his second eldest daughter (who I had been told previously had commented that she found me cute) during a summer pool party... What could go wrong right?

The party was hellishly fun, the alcohol was kept to a minimum and Marilynn and Rob seemed to put on a good front for everyone. There was a lot of bikinis and scattered ass near jailbait ass around (his brother has 2 sons and 2 daughters, one 17 and one 19. Both fine as fuck). So sufficed to say that a fun time was generally had by all. I spent a lot of time in the pool playing games with people, including Lindsey who seemed to enjoy hanging out with me (thus driving home exactly what Marilynn had told me previously). However, I wasn't planning on getting fired, so I kept it strictly platonic throughout. That was of course until about 2 hours in when Paige turned up. I'd been going through a lot of things in my head about the events at Dunkin (romantic location, I know) and I figured that I actually kind of liked Paige, like a lot more than I expected to. I saw her come out, grab a drink and then head back inside the house. I excused myself, grabbed a towel to dry myself off a bit and then headed into the wetroom at the back of the house where she was sitting. It turned out that she was trying to get things done for the project as she was running a little behind after deciding to change several of the screens within the GUI. Nothing major for me as the code was sound, just move a few locations around, but for her it was a ton of work. I knelt myself down beside her and looked over her shoulder and she showed me the new designs. Now to be fair to this girl, her talent had evolved tenfold in the time since she started working for the company, although again that could have been a biased decision based upon my burgeoning feelings for her.

We spent about 10 minutes chatting about the design before sinking into one of those pretty awkward silences. She looked like she wanted to say something but wouldn't so I just pretty much came out and asked her. "So what about the other night?" She gave me a smile, but also said that she wasn't sure what happened and that it just kind of happened and that she didn't dislike it but..... before doing a classic taper off to nothing. Of course, not being an idiot I knew what the but was (colleagues, I work for her father and I'm 9 years older than her). I told her it was cool, wished her the best on getting the designs done and headed back outside. I spent the rest of the day back in the pool acting the fool and generally having a laugh before heading home.

A few days later at work my boss called me into his office. Paige was already in there at the time, so Immediately I thought that I was done for, (not for fucking his wife though, but for kissing his first born). However it turned out that the client wanted us to take the software to a conference and present it to the board at said conference and that we'd been spending 3 days in Boston, driving down there from NY and driving back together. I didn't even need to look at her to sense the way she was feeling, I could just tell. He told us that we would be leaving in 2 days and would be staying over the weekend. With that we filed out and went out separate ways.

2 days later, I was driving the Mini down to Boston with Paige in the passenger seat. It's not a short journey from NYC to Boston, so we had plenty of time to avoid the main topic of conversation and just bullshit for most of the drive. During this time my opinion of her changed completely. Prior to working with her I would have called her a pretty vapid, vacuous health nut with very little personality and I would have been wrong. After a point, we stopped for a drink and to swap places so she could spell me with the driving. During the stop she went off to the bathrooms to change as it was pretty hot in the car. She came out with a little pair of short swimming shorts and a spaghetti strap top on. There were a few guys checking her out as we left, which made me smile a little. The rest of the journey was filled with just bullshitting and cracking jokes before we arrived in the early evening.

We'd been put up in a hotel in the Theater District of Boston, there was no tacky instances of "only one room available so we had to share". We had two very nice rooms on two different floors. We agreed to meet up for dinner after we freshened up. I went and took a shower, and I will freely admit to stroking one out whilst thinking of the way her ass looked in those shorts. We met up and hung out for the meal, then walked back to the hotel and went to bed early as we had the presentation at 10am the following morning in the Downtown area of Boston. She had said she was feeling nervous as she hadn't presented before, but I told her we'd be fine as I'd done things like that before.

The next morning I went to meet her, we were both smartly dressed (me in the 2 piece suit and tie, her in a nice little black dress and heels and some very well applied makeup. She had put her hair up and it really accented her eyes and her face perfectly. To say that we killed the presentation would be an understatement. We nailed it so completely that they ended up wanting to use again another for another 2 projects later in the year. She did awesome during the presentation too, all nerves went out the window. When we were heading back to the hotel we agreed that we should celebrate tonight. She called up her dad and told him the news and he told us to book a dinner and she could pay on the company card, so we did. We headed back to the hotel to decompress after the conference presentation and relax, she called down to my room and told me she had made reservations for a place for 6. At 5.30 I went to her room to get her, she had dressed very casually for the meal, a grey pencil skirt, heels and a thin little blouse that was cut a little lower at the front. We walked to the restaurant and enjoyed what was a very good, and to all accounts very expensive, dinner. Afterward we decided to celebrate by hitting up a club too, fortunately the area we were in had a lot of clubs, so we found one on my phone and headed there.

The club was pretty full (it was a Saturday night after all). It was at this point that I realized that Paige was actually a really good dancer, little slutty at times, but a really good dancer. She was a grinder for the most part, I didn't mind though as it gave me a real chance to "paw" her a little. As the drinks flowed the inhibitions gave way a little and I wound up grabbing her ass, when she didn't object I gave a little squeeze to make sure she knew it was there, she gave me a very dirty smile and just kept dancing against me. We spent a fair few hours at the club, alternating between alcohol (one of the few times I allowed myself a drink in celebration) and water to keep us hydrated. After a point however we wound up leaving and decided to get a taxi back to the hotel. She had become very giggly during the taxi ride, she was pretty well sloshed by this point though. I'd only had a couple and had balanced it out with a lot of water to keep myself as sober as possible. At one point in the cab she wound up kissing me again, completely out of the blue. This time though it was pretty different, I could feel a need behind it. She pulled away with another giggle before kissing me again, now with extra tongue. My feelings being what they were, I obliged and we wound up making out in the back of the cab (sorry cab driver, tacky as fuck and not usually me).

When we got back to the hotel, I paid the driver and we headed inside, she was holding onto my arm as we got into the elevator. Once the doors closed she kissed me again, although this was almost more of a pounce as she pressed herself against me and knocked me back against the wall. The kiss only lasted a few moments as she broke it off once the door opened to my floor. She simply took my hand and walked out of the elevator toward my room. I followed, growing increasingly intrigued by the second (didn't want to hope, but you never know). I opened the door and let us both in, she immediately went into the bathroom and closed the door (I figured, when you gotta go, you gotta go right?) I sat down on the bed, took off my shoes and threw my jacket down on the chair. I head the toilet flush, but when she came out she was only wearing a flesh coloured bra and a black thong. I remember the look on her face perfectly as she was kind of nervously chewing her lip as she stood there. When I motioned her over she came to me. I immediately grabbed her ass and pulled her toward me. I kissed her stomach below the belly button and then further down, kissing over the front of her thong. I felt her shiver a little as I planted kisses there, but I just gripped her ass a little tighter.

Figuring that I shouldn't wait too long incase she changed her mind I went to work, I inched down the front of her thong and revealed (much to my surprise) a shaven haven, respect (Ali G quote ftw). I remember looking up at her with a raised eyebrow, to which she just shrugged. I immediately pulled her thong down and she stepped out of it. I pulled her down onto the bed next to me and rolled her over onto her back, rolling myself on top. I felt her squirming a little beneath me, I held myself up over her and kissed her again, I felt her lift up, pressing her pelvis against mine. I slowly kissed down her body, over her breasts still covered by the bra and down her belly before beginning to eat her out.

She was definitely more vocal than anyone I'd previously been with. almost everything I did elicited a moan. She certainly wasn't as directional as her mother, but I'd already learned a lot of what I needed to know. Very quickly she started pushing up against my mouth, grunting and panting and grabbing at the sheets. Now, I love pleasuring a woman and hearing her reaction (see Part 3 for my feelings toward that), but I was also dying to get my dick sucked. I pulled away, she gave a bit of a frustrated sound for a second before she saw me fumbling with my pants. I wound up pulling my pants down and throwing them with her underwear, swiftly followed by my boxers. She smiled when she saw what was in store for her, I had to assume that I wasn't her first black guy given the way she looked at my dick. I grabbed her again, maneuvering her into a 69 and went back to work. I don't usually do 69 that much to be honest, as I like to see what is going on. But there is definitely something to be said for the feeling of unexpectedness that came with wondering when she would start. I felt her hand around my shaft, then followed by her mouth around the head. To say that she sucked dick good would be an understatement. I swear she could have sucked the chrome from a tow hitch. I can usually last pretty well with oral unless the situation is overwhelming (see part 1), but between her groaning with it still in her mouth and the general level of oral skill that she possessed I was tapping out. She spun around and got to her knees. Very quickly after her bra was off, as was my shirt. She had a fine sheen of sweat over her already and her hair was pretty messed up (given how pin straight it usually was). She gave me a look that I can only describe as pure lust as she straddled over me, telling me that she was on birth control but I couldn't cum inside her (we had no condoms as neither of us planned this, so beside my better judgement I went along). Hell, I just wanted to hit this pussy, by this point I truly didn't care if it was in her, on her or somewhere in her presence as long as I did indeed cum. One hand went beneath her and around my cock just above my balls, she gave it a tight squeeze which actually hurt a little and then lowered herself down onto me. I swear to god, she had the single tightest pussy that I've ever had the fortune of being inside, I just held on and enjoyed the ride, one hand on her ass and the other groping the tits. We were at it for what felt like a long while, what started with cowgirl went through a little missionary (not a huge fan of this position, kind of boring), spoon, reverse cowgirl and ended with doggy. Due to how tight she was I had to take a couple of very short breaks between positions, usually just after she came, to desensitize myself a little (that shit does really work). She was incredibly vocal throughout the entire thing (tacky loud hotel sex ftw), to the point that at times I thought she was a little too vocal that it came off sounding like a cheap porno. When I finally let myself go I wound up coating her lower back and ass. Being a gentleman I was the first to stand and get her a cloth to clean herself off. She took it into the bathroom and showered to clean herself off. I followed suit and cleaned up, couldn't help but remember that just over 24 hours previously I'd been stroking one out to the same image that I'd just partaken in. when I came out of the shower she was laid in the bed, watching TV like everything was normal.

She opted to stay the night, and initiate another session just after we turned off the lights. (i've never fucked in the pitch dark before, it was pretty hot to be honest). I was laying on my side with her facing away from me just talking to each other when I felt her hand reach back again, stroking her fingertips along my junk. She formed her hand around my cock and inched herself backwards slowly until I could feel the swelling head against her asscheeks. At one point she grabbed the shaft again and pointed it down between her legs, the head rubbed against her fingers and I felt her shiver a little. I took the lead and slide my arm over over, pulling her back slightly, she bent her legs forward a little and helped me back inside. Again, we fucked like this for about 20-25 mins I think (I was pretty much spent after earlier, so I was good for a pretty long while at this point). We ended when she came again, this time she just rolled over, kissed me and then turned back around to fall asleep. I backed off a bit and then fell asleep pretty quickly myself.

We woke up pretty fucking late on Sunday, we didn't have much to do other than to check out and head home. We ended up having sex again in the morning in the bed, and then again in the shower when I was cleaning up and she came to join me. She left to go back to her room and pack her shit up, I got everything ready to go and we met downstairs to check out. During the first part of the drive back she slept a lot, then I did the same when it was her turn to drive. Before we got back onto LI she made me promise not to say anything to her Dad yet, that she would speak to him first. I had figured that she was just looking for a one night thing, not something more, but I wasn't going to argue. I couldn't figure out how I was going to break it to Marilynn though. You know, I legitimately liked Paige, I didn't really want to be fucking her mother whilst I was going out with her. She dropped me off at my friends house before heading back herself. I got one more kiss (I had asked to see her tits one more time, but a kiss will do) and she left. As I settled down for the night, having filled my friend in on the details, she sent me a text. It was a very tasteful, but also very hot semi-naked selfie (i got to see tits again! Yay!).

The rest of july was spent pretty much sneaking around wherever we could as she couldn't figure out how to tell her father. I still hadn't heard from Marilynn, so I hadn't had to bring anything up yet either but August was about to hold many surprises both good and bad.