[MF] booze, coke, anal. fucking my 60 year old boss

So this happened when I was working in the mailroom for a big real state firm. I was 22 years old. I worked in retail and hospitality ( waiter), but this was my first “real job”. I come from a lower middle class family. There was never any money for continuing my education so I bounced around shity job after shity job to help fund my associates degree.

The mail room had four full time employees including me. The building we worked in had four floors and we were in the basement. Each one of us had our own floor that we were in charge of. I had the top floor, this department basically dealt with rentals. Listing available apartments, collecting rent, showing apartments. The busiest time for me was the end of the month when all the fucking rent came in ( this was 06-07, digital payment was not what it is today). Anyways, I had to individually place all the rent checks in these file folders, then give the files to the manger. She would always make me sit at her desk and read the checks out loud to her as she entered them into her computer… It was a long process.

The manger was a women. She was right around 57-60 years old. She was skinny but toned. She took care of her body. Her hair was not dyed, her blonde was fading to a silverfish color and she would most often wear it down. She wasn’t very well liked by her department due to the fact that she was pretty demanding, and at times very confrontational. She dressed well, always wore suits with and high heels. She always really nice to me. when I would bring her the checks, (if she was ready to enter the data) she would tell me to sit we would bullshit for a bit and sometimes flirt.

The company had just closed a deal on a 500 plus unit building that they were planning on renting out. She played a key role in acquiring the building for the right price and all the other bullshit that comes with a multi million dollar deal. Anyways, the executives and all the mangers had a lunch party to celebrate. She got pretty bombed. This was apparent to me when I dropped her mail off at the end of the day. It was a Friday, she was in a good mood and she was drinking out of her coffee cup. She normal doesn’t drink coffee that late in the day.. She told me about the party and how she was keeping the buzz going and she told me to try her coffee with a giggle. As soon as i put if up to my face I could smell that it wasn’t coffee. I took a sip and It was pure vodka. I coughed and laughed and said something like I support this 100%. Before I left she told me that she had rented out a bar a few blocks away for the office and extended the invite. At first I declined, being the mailroom boy, but then she said something along the lines of ” there has to be at least one person at the party who likes me”. I let out a nervous laugh and reassured her that she is liked and some other bullshit, and eventually agreed to stop by for one.

Being lowest man on seniority in the mailroom my job at the end of the day was to go floor by floor picking up all the outgoing mail. I’m always the last person to leave and I’m usually there an hour later then everybody. I finish up and head to the bar. I told myself it would be for just one.

as I was pulling Into the bar, the parking lot was empty and I figured I missed everyone. I walk in and the bar is empty, I see the area that was rented out. It had those aluminum food trays, and they looked like they had been barely touched. I look over at the bar and I see the manger drinking alone. I tap her on the shoulder and she was happy to see me. She gave me a hug. It was strange, it almost looked like a sense of relief had fallen over her. She told me that not a lot of people showed up and the few that did had already left. I could tell she was bummed. But she said she payed for 3 hours of open bar so I better start drinking. I nervously laugh and order a drink.

We end up drinking till the end of the open bar. In that time we covered everything from my professional goals, to my dating life, to her two failed marriages. The bartender reminded us that the open bar was over and then she looked at me and asked if I wanted to keep bar hoping. I was pretty drunk and told her I don’t think I could drive and she agreed that we both shouldn’t drive but that she would pay for a cab and that she would also pay for my cab home whenever I wanted to call it a night. I agreed.

We get our cab and we are on our way to bar when she pulls out of her purse a little baggy of coke, and a pack of parliament cigs. I’m in shocked and I start laughing at the situation. She says something like don’t be a bad boy and tell on me and proceeds to pour some coke into the raised filter, she does a quick bump and then lights the cig. She then gives me a look, implying if I wanted some and my brain said no but my gut said yes. I take my bump and have my smoke, I can feel the coke tingling my face and my buzz is amplified by the nicotine. I’m feeling great.

We get to the bar and people working there all seem to know her, I ask if she is a local and she says she lives a block away and comes here after work regularly. We don’t sit at the bar, we sit at a booth. We are having a good time. Every 45 mins or so we would go out for a bump and a smoke. Time gets away from us, and before I know it its 3 am and the bar is closing. We leave, outside I flag a cab and about to get in when she tells me that she promised to pay for it and goes into her purse, and tells me that she has no cash but if I come back with her to her place she will give me the cash, and she was only a five min walk. I decline but she insist, she is not very subtle, and grabs my hand and pretty much drags me away from the cab. She links my arms as we walk back to her place.

She owned a condo in a three flat brick building, in an expensive part of the city. She leads me up the stairs to her apartment. I can’t believe this is happening and I am nervous, we get into her condo and she tells me to sit and offers me a drink. I nervously say only if you are gonna have one or some dumb shit. She says of course and that she will be right back with the money. I’m sitting on her 5 thousand dollar coach sweating from nerves. When she reappears I knew that I wasn’t gonna be leaving that night.

She comes out of her bedroom in a short red silk robe. I knew she wasn’t wearing any thing under it by the way it griped her tight thin body, also her nipples we rock hard. She pours some wine and hands me the glass. The cab fair is non existent.

One thing leads to another and we are passionately sucking on each others faces. She straddles me and drops her robe. She is completely fucking naked and dry humping the shit out of me. I am sucking on her b cub breast and kissing her neck and she is grinding the shit out of me. There is just one problem I can only maintain this half chub bullshit. She slides down to the floor and pulls my pants off. She starts swirling her tongue on the head of my cock, followed by spitting on the shaft and stroking it. I have never been so turned on but I still could not get a hard. She starts giggling and says I know what you need, she get ups and goes to the bathroom and returns with a little blue pill. She tells me coke and hard cocks don’t mix and hands me the viagra. I take it, and she continues to suck and jerk till finally I am fully hard. She starts choking her self with my cock and I can tell she is tearing up by the way her eyeliner is smearing. She pulls away after her first attempted at a deepthroat coughing. Once she catches her breath she tells me she wants it in her.

She is older, so down there needs a lot of lube, she pours about half a bottle of astroglide on her pussy and the left over lube she strokes my cock with. She bends over her bed in the doggy position. I slide my fat cock into her pussy, and it’s a tight fit, she is moaning and I slowly push deeper and deeper till I am all in. She screaming and tells me to destroy her pussy. I start going full thrust, and she keeps yelling harder between moans, after awhile she tells me she wants me to fuck her ass with my big cock and she pulls away. She flips to her back at the foot of her bed covers my raging cock with the remaining amount of lube. She pulls her legs up, and is holding them with her hands reveling a tight little asshole and a red pussy that I just destroyed, I grab my cock and I get the head in, she is moaning. I grab her ankles and I start to push my cock into her tight asshole. She cums again and soon after that I am cuming. I tell her, and she yells cum in my ass, and I can feel my cock pulsating in her ass and I let out a moan, i pull out and she is flexing her asshole and I can see my load pooling out of once was her tight ass. We lay next to each other and share a cig before we both pass out.

That was the night i fucked my 60 year old manager.

Source: reddit.com/r/gonewildstories/comments/63mydx/mf_booze_coke_anal_fucking_my_60_year_old_boss