Office Sex, Sex Confessions

Sex Confessions #39: I Got Drunk with a Coworker

Hello all,

You now know about my slacker work life, my having sex in my bosses office, and soon about a crazy nite of drugs, alcohol, and girls that will hopefully be posted here soon.

A word before we begin; In response to a reader that complained about how long my posts are; well, If you just want a short footnote paragraph detailing my exploits then you should look elsewhere; I don’t like to gloss over anything and I want whoever reads about my exploits to understand and envision the experiences as if they were there too.

This means including every minute detail about said experiences. I like to write and I have the time to do so. For the longest time I have kept these experiences to myself and this is my chance to let them go. This is as cathartic for me to write as it is enjoyable for some of you to read.

That being said, let’s proceed……..

The following is one of the “bad” ones that I’m really not sure about how I should feel and really just want to get this off my chest….

A few weeks ago I was working (yes I sometimes DO work) with a female coworker of whom I was fairly acquainted with on a friendly basis.

We’ve hung out together before with other people from work a few times and have been sent outta town together on a few training trips by our respective dept’s and though we’ve always gotten along and had a good time, nothing romantic or sexual has ever happened between us.

Not that I wouldn’t do her; She is cute, about 5’7, brunette, 30, nice body, not “too” anything. I just never got the idea that she would ever be attracted to me and she is always bitching about her boyfriend always dumping her. (which he seems to do on a fairly regular basis.), in other words; I was in the “friend zone”.

The thing about her is that we always end up platonically talking about freaky sexual shit (this is an important factor regarding the point of this story). It always turns me on but we talk about it in such matter of fact terms that it seems that she only tells me this shit because she thinks I wouldn’t screw her because she knows I know that I’m not her type(she’d pretty much made that clear).

Ok, so back to the basics; we were working via email on a project together and pretty much having a good time talking about what we would rather be doing with our lives when she mentioned that she had an interesting idea for a podcast and was looking into pursuing it but doesn’t want to say what it is because she’s afraid of it being stolen.

Now me being the sexual deviant that I am and knowing that she is somewhat freaky (more on that later)immediately assume that it has to be something of a sexual nature.

She has told me more than once that she and her boyfriend have taken pics of each other doing each other and I was thinking that she was getting into porno somehow. SO I badger her telling her that whatever it is, it couldn’t be worse than anything I’ve done (wink,wink).

She doesn’t agree to tell me until I promise to discuss it with her over drinks after work and I’m buying. So the whole rest of the day I’m thinking “WTF is this girl up to?” and it drives me crazy!Finally quitting time comes around and we agree to go to a lounge I like to take girls when I think I’m going to get some.

It’s a nice Martini lounge with nice jazz, low lighting, comfy chairs, and bartenders who know my name, what I like to drink, AND who always give me a discount and pour heavy due to my habit of being a great tipper.

So we are chilling there having a few drinks and small talking about how our day was when I just say; “look, you’re killing me here, WHAT is this idea you were talking about!?”

She has another drink and says, well I won’t spoil it for her by blabbing it here but suffice to say that it had NOTHING to do with what I thought and I pretty much felt like an asshole for thinking what I was.

So the convo turns from her ambitions back to her and her personal life, specifically her shitty love life……yippy.

So after listening to her drone about, in this order, her brother who used to like to beat her up regularly and used to like to sneak into her room when he thought she was asleep and then rub his dick all over her when they were teenagers (gross), her mother’s funeral, and something that she thought everyone knew about that was being gossiped about concerning her, a business trip, and another co-worker.

The topic as always shifts back to our respective sex lives; she tells me about how her sometimesex is a porn fanatic who’s bisexual and wants to share her with another man, or I should say how HE wants to share another man with her (?!), how she’s afraid that the woman that they had a threesome with is after him for herself, and skinny dipping while camping with friends then having an outdoor orgy with said friends and how everytime she’s had anal sex she’s never realized it until she woke up the next day with a sore ass.

Now at this point we’ve had a few drinks and are both a bit buzzed when she asks me what I meant earlier by her not possibly having done anything worse than I have?

Well I’m no angel and I tell her about some of my sexual (mis)adventures. What really seemed to catch her eye was when I told her about the time I went to a swingers sex club here in town. I told her what went on and about how wild it was and I could tell by her questions that she really wanted to go.

I took the initiative and ASKED her if she wanted to go to which she said yes. Now this started a whole new slew of questions from her about the place and what goes on there.

I told her everything I saw and did and even made up some shit because it looked to me like she was getting turned on!

So things are going good and I ask her if she wants to go outside for a smoke, (ganja). She goes gaga over this because she never figured me for smoking weed and we go outside to partake. I didn’t have a lot on me but had more at my place and asked her if she wanted to come over to smoke some more. She was interested in the weed (it was the purple) and readily agreed so we went back inside, paid the tab, and took off for the short walk to my pad.

During the walk the buzz kicks in and she breaks out her ipod, puts her arm in mine, and sticks one earphone in my ear while putting the other in hers so we can both listen to the music on the way home.

We get to my pad and I pack a bowl and we talk some more……….about frikk’n music! That’s ALL she keeps talking about until she sees my video camera.

She asks about the kind of stuff I like to film and if there is anything dirty on there?


ME: “like what and that depends on what you consider dirty”

HER: “what, are you on here with girls? Is there a pic of your thing?”

ME (laughing off her question about my “thing”): “naahhh, I take boring pics, mostly of the city. Why?”

HER: “Just didn’t want to see anything I wasn’t supposed to is all”

Now I could have said something clever like “who says you ain’t supposed to?” or something like that but we were both drunk/high and all I could do at the time was just laugh.


She THEN says;

“Huh, I’ve never seen a black one before, except in the movies”

Me (being black, (yeh thass right, surprised?) I’m thinking I’m on to something here): “Well then you’ve probably seen some of my work!”

(I have NO idea what I’m talking about)

ME/HER: nervous laughter

Just then her cell rings and the conversation indicates that she will be leaving soon; whoever she’s talking too is trying to get her to come join them so I’m thinkin that I have a once in a lifetime chance here and rack my brain to figure out a way to interest her in staying; at this point the weed, the wine, and the nature of the conversation has made me fucking HORNY as hell, especially her last comment about “not seeing a black one before”.

So sure enough she gets off the phone and says that she is going to have to go soon and thanks for a great evening. I’m like, whoaa, I was just about to pack another bowl!

Howzabout it?

SHe’s like ok and we sit on the couch and talk some more, this time i gear the conversation back to more of a sexual nature, mainly about pornos cuz I know she likes them and I have a few……..hundred (nahhh, just kidding). She tells me that her and her (ex) boyfriend made a couple and that they liked to enjoy watching them together so I lie and tell her that I had made a few myself and that’s what I really meant by my earlier remark. She’s like, wow, cool but still mentions she is getting ready to leave soon.

Ok fellas, moment of truth here, I DO NOT RECOMMEND THE FOLLOWING COURSE OF


SO She’s about to leave and I’m horny as hell, we finish the bowl and I ask her when she wants to go to the sex club, she says this friday, (it was wednesday).

I agree and we proceed to make arrangements to put our names on the guest list via internet. I was too stoned and kept fucking it up so she said to let her do it. I was sitting in the computer chair and had to stand up to let her use the keyboard, thing was, I had a full on boner, rock hard and pup tenting my pants!

Now this was in plain view and she couldn’t have missed it. She got on the keyboard and put us on the guest list then what happened next is sort of a blur but I DO remember her looking at me and saying that she should probably go.

I ask her if she is sure and then, for whatever reasons;



I remember her saying “don’t!” and backing away while making a motion to cover her eyes but it was too late; Mr. Happy McHardon was out there for her viewing pleasure….or displeasure.

Oh god.

So there we are, me sitting there with my huge member pointing to the ceiling, well actually it kinda tilted to the side in her direction.

I was terrified at the realization of what I had just done. I figured, “Oh shit, at the best she’ll just talk about this at work, at the worst she’ll leave and come back with the cops to which, honestly, I would just tell them the honest truth;I was raised on pornos and that’s how I learned sex was initiated.

She just kind of stared at it in shock for a few seconds……. then to MY amazement slowly approached me for a closer look! She examined it for a few more seconds then said that she would probably climb on top of that at the club…….but NOT here in my pad.

Chastened, embarrassed, and still somewhat turned on by her casual interest, I hastily mutter out an apology while putting him back in and explain to her that it must have been the weed, booze, etc, and that hanging out with orgy people has distorted my sense of propriety when it comes to sex.

I also tell her that it turned me on incredibly that she would want to come to the club with me and that I couldn’t help myself.

She just laughed and, here is what really fucks me up, somewhere along the line, for whatever reason, she tongue kissed me and then said it was cool and to then walk her out.

So I walked her out to the train and she left to go meet her friends. I went back and laid awake all nite wondering who at work she would tell about what I did. I was even more worried when she emailed me the next day cancelling our trip to the club.

I emailed her back apologizing again to which she said to not even worry about it, here is a paste of the e-conversation;

— “C”wrote:

> hey d. i think i’d rather experience my first time at a party where i can have a drink and smoke a little…just to loosen me up…maybe the next party? i’ll be back in the bay next saturday(**** for training all week). is that cool?



note- (At the bar, I had mentioned that the people that I went to the sex club with like to have orgy/parties at their house and that since there was no alcohol nor smoking at the club,those house parties were more fun than the club)


On 3/23/06, “D” wrote:

> Yeh, no worries. I definetely wouldn’t want you to be uncomfortable, ESPECIALLY in this type of situation and the house parties are probably the best thing for your first time since they’re pretty mellow and relaxed.

>Just let me know when you are ready and I’ll plan accordingly. Hey, I had a great time last nite hangin with you and hope I didn’t go over the line, I’m just crazy like that and I guess tht’s why I roll with the types of crowds that I do.

>Anyway, I’ll be back in the office tomorrow but if I don’t see you before then, have a nice trip and let me know what you want to do when you get back!

> Peace,


> D


“C” wrote:

i had a lot of fun too…and i wasn’t worried about it.WOW you have a huge purple penis!!!

but the next house party…i’m so down…and up…and any other way i would be.

see ya tomorrow…i’m sneaking out early to enjoy some friday though…shhhh!

She then followed this up with the following;


On 3/23/06, “C” wrote:

> and don’t ever tell.

(attached were two very clear pics of her sucking her bf’ off!)


followed by:

> On 3/23/06, “C” wrote:

> > ps.

> > because you showed me yours…

(attached being a pic of her bare spread ass, anus and all, and another, a pov shot of her bf eating her out)”


Now I love and appreciate these pics and on one hand it relaxes my fear that she would tell anyone what I did for what I suppose would be her fear of me letting these pics out, and trust me; there is NO mistaking that this is her!



on the other I’m afraid that she might not just give a shit either way; she knows that some people at work already think she is a freak and she’s cool but not all “there” and .. Like I’ve said, I’ve left her alone since she returned from vacation and she hasn’t emailed or called me either since.

I really don’t know what to say, and the night in question happened almost two months ago now. We had a brief run-in in a hallway once last week but I didn’t say anything about that nite and neither did she.

She is away on another business trip but when she gets back I’m thinking of giving her a call just for closure.

So there you have it dear readers; an exploit that I’m not too proud of but it happened and I learned from it. I’m just glad that she was cool because I lie awake thinking of how else it could have turned out.


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