The Awkward Man Cummeth

Awkward can be sexy. Its cute.  And to let you in on a little secret, I'm a mother, and a lady, and sometimes I enjoy some sensual, intellectual, cute sexy intimacy to go along with the athletic, sweaty, physical and emotional boundary stretching fuckfests that so many of my guy friends like sharing with me.  Okay, and some of my gorgeous lady friends.  And another okay, it's my idea to have a sexual throw-down all out orgy about as often as it's my lovers' idea.

 

But back to awkward.

 

Everyone at our public relations agency knew Matt wasn't getting any at home.  He was 48 years old, married around twenty years, one child in high school, and another child in junior high.  He was under a ton of financial strain at home as he married a woman used to the "good life" and he was trying to live a life of luxury on what was more like upper-middle class money.  Nothing wrong with what Matt was making, but it didn't match his wife's budget.  She was, we surmised, withholding sex as either punishment for not meeting her financial demands, or as a financial incentive for him to earn more.  Poor guy.  Why don't American women fuck their husbands more?  Then again, maybe if they did, the men might not be quite so interested in fucking me.  So to all the icy shrews here in America, thank you. Your cold bed is my hot pussy's gain.

 

But Matt never did anything inappropriate to follow up on his crush on me. Oh yes, it was clear that Matt had a crush on me.  (Smile)

 

How did I know about the crush?  Dolly knows.  Matt's eyes, that was the giveaway, they were all over me, in the lustful way that makes Dolly wet, blush, feel warm and hot & sexy.  Oh I love when I have captured a man's attention, even as my thirties began to exist more and more only in my memory and rear view mirror, I always appreciate being included in a man's dirty sex thoughts. So yes, Matt was a married man nearly a decade older than me, henpecked at home, yearning for release and to feel successful (and he was successful, he was good at his job, decently handsome, witty, and client's loved him), which made him definitely the type of man I love sharing my body and bedroom skills with.

 

Surprisingly, our inevitable coupling started over a donut and a pizza.  No, not at the same meal. That would be way too many carbs.

 

There was a public building demolition, and our office tower had a great view.  I think a new mixed-use development is what is being built on the site of the non-descript, hideous 1960's low rise office building, which must have been state of the art during the Kennedy-Johnson years when it was built and opened, considering the prime real estate it occupied. 

 

Matt was the partner hosting the viewing party.  Donuts and Dynamite, that was his theme.  Cute.  Witty.  He stuck his head in my door on one of my rate days in the office catching up on billing and paperwork, and asked if I'd be at the party, was I bringing any guests, as he didn't want to run short of donuts.

 

"Not my thing, Matt, watching the implosion, but thank you for organizing."

 

Poor Matt, looked disappointed.  He must look like that at home a lot, I thought.  Goes home after a job well done, and gets criticized that his house isn't as big as someone else's, or the cars aren't' as new, or the vacation destinations aren't as exclusive.... we all know men who are getting treated this way, don't we?  Well, my inclination is often to think, "I'll bet a good rollicking Dollification would be just the ticket to cure that man's blues."

 

I replied to his crestfallen look with my Dolly smile (love my dentist; keeps smiles gorgeous and eats pussy like he's been locked in prison for a decade, so well that his quick-shot premature cumming is never a let-down.) and told him, "Don't worry, Matt, we'll bond, just not over a donut or dynamite."

 

Did I see a cock twitch in his trousers when I said, "we'll bond"?  Don't know, because Matt doesn't dress in tight slacks like a Millennial and his tailored suit had pleated pants so his cock was tastefully not on public display via bulge or outline through the fabric.  Matt was cute and had class.

 

But apparently me telling him that he and I were going to bond left him momentarily speechless.  That was my first flirty line to him in the three years since he'd joined my family's agency. I know, such self-control from Dolly Jewel, who knew? *Wink!

 

"Tell you what, Matt; I'm out doing my morning runs when they blow up old buildings around here, but sometime after work you can show me the video, maybe over a glass of wine?"  And I might have winked as I said the word "wine".

 

He smiled and I saw his Adam's apple bob.  "Uh, yeah, sure, that'd be great, um, so I'd better, uh, have a great day, Dolly."

 

I confess I was thinking about Matt later that evening, just a bit of the time, on a Dolly date with an accountant who was a more dynamic business man than Matt but who was awkward with condoms.  When I saw him flustered, I thought of Matt.  Then I said, "no worries, lover" Mr. Dynamic but condom-challenged, and proceeded to lick his momentarily less than dynamic cock back to full readiness, place the condom on myself this time, and then I rode that wonderfully restored cock until he reached his back-arching, toe-curling, "oh fuck" exclaiming orgasm.  Yes, thinking of him, Mr. Accountant during the actual cock-riding and condom-filling part of the Dolly date.  Ah, all in a day's work.

 

So then the day before Thanksgiving, I was not traveling, it was my year with my children for the holiday under the terms of my divorce decree so we were home, together, with my parents, my siblings, my nieces and nephews, some  stray boyfriends or girlfriends of my older nieces and nephews, and since the major aspects of the meal, namely the turkey, was being catered I had time on Wednesday, the day before the holiday, to swing by the office and again, enter some updated billing and other information into our computer systems.  Why did I have time that Wednesday?  I have to admit that even though I've had fancier caterers for other events, the commercials that are ever-present on television in Florida throughout the holidays from Publix won me over, and shopping at Publix IS a pleasure, and we order the turkey and some of the sides for Thanksgiving Day from our local supermarket.  I do the healthy sides myself though. 

 

There were three of us in the office. Me, Matt, and Lisa, our receptionist, a sexy twenty-four year old with a virile twenty six year old boyfriend (saw him at last year's Christmas Party, thought he'd make a yummy appetizer, and asked his age.  Was dipping my manicured finger into his drink to steal an ice cube, then placing that manicured finger seductively on my tongue while standing inappropriately close to yummy boyfriend, wearing a décolletage- emphasizing dress wrong?  And our receptionist, Lisa, watched and then stepped up, handed me one of the two glasses of champagne she'd retrieved from the bar, and said, "I see you've met Chad, Dolly.  We should all go out sometime, would you like that, Chad?"

 

I just sucked my finger, the last trace of Grey Goose and lemon from yummy boy's drink and stolen ice cube tasting like sexual victory at that moment.  Lisa winked.  She and I have flirted and perhaps more.  *Wink.  But the point of telling you this is that Chad was tongue-tied and I thought it so cute.  I'm thinking back to that since lately I've been finding Matt to be cute in his awkward, tongue-tied condition as he has the desire to want to fuck me but hadn't done anything to make it happen.  At least not up to that point.

 

So there we were, Lisa, Matt, and me, the day before Thanksgiving.  Matt suggested we bring in a pizza for lunch.  Lisa wanted black olives and mushrooms.  Matt suggested pepperoni, but said he wasn't "an olive guy".

 

I said I'd brought a little quinoa salad and thanked them but that I was passing on the pizza.  I also said, "But Matt, if you're not an olive guy, what do you do when you have a martini?"

 

"I don't drink martini's, Dolly.  But um, uh really, no pizza?  I can switch to just cheese if you didn't want pepperoni?"

 

Awww..  A man altering his pizza toppings for me.  I slept with boys in college over lesser gestures than that.  No comment on whether I did so in high school, too.  *Wink!  (Lots of winks today!  Such fine memories my life of pleasure has provided!).

 

"You two enjoy the toppings you want.  Order two pizzas, take the extra home, charge it to the firm, you'll need the extra as the something to eat during the earlier football game before your turkey dinner begins, tomorrow.  And leftover pizza is kind of sexy, don't you think, or is it only sexy when you're having cold pizza after spontaneous sex leads to an unplanned sleepover?"

 

Definite cock bob in Matt's pants.  Day before the holiday, so we were all casual, and Matt was wearing blue jeans that fit snugly.  Nice butt, Matt.  He was doing 5k's of late, and bringing the finisher medals into the office.  Again, cute, even though finisher medals for a 5k cheapen ever real runner's effort.  Even 10k finisher medals seem overly indulgent to the generation who have taught their children that everyone gets a participation trophy.

 

Sorry, off my soapbox.  I got this body from training my ass down to its level of fitness and fuckability, my flat abs from saying no thank you to pizza and donuts... 

 

So Matt and Lisa split a pizza, not taking me up on ordering two, and I brought my quinoa salad into our break room to join them.  We talked about our Thanksgiving plans.  Mine involved a distance run in the morning, and then making some of the sides involving squash and green beans only with healthier ingredient swaps from the traditional, fat-laden recipes.  Damn, here I am back on my healthy eating soap-box. 

 

Lisa was also wearing jeans.  Sexy, skinny, painted on, wouldn't you like to lick my pussy and fuck me hard kind of jeans.  I always get a picture in my mind of Chad going to town on Lisa. She smiled. Did she know what I was thinking?  Maybe.  After all, it was an actual memory, not a lusty desire imagined.  That Christmas party suggestion she'd made, that I mentioned earlier in this blog, well it led to watching the Orange Bowl that year from a suite in Joe Robbie Stadium (that was its original name, and Daddy still calls it that.  Technically its Hard Rock Stadium now)  with Chad and Lisa, then deciding three quarters and however many drinks they'd had (love that luxury box catering, you know?) and we Uber'd back to my place since my children were with their dad and after I straddled Lisa on a sofa and deeply kissed her, raising her hands to my breasts and then we started humping and soon enough clothes were on the floor and Chad was helping and I asked to be their fluffer and so, so HOT to watch Chad slam a winning load home bareback into his girlfriend, the lovely orgasmic squirting Lisa, and then getting to clean Lisa up and enjoying Chad's tasty cream pie on my hands and knees while Chad earned All American pussy eating honors from behind me and then I wrapped him in a condom and rode him while Lisa licked his shaft on his pull-backs and then my clit and my taint and God Damn that was hot sex...

 

So anyway, day before Thanksgiving, as sexy Lisa was finishing a slice and a salad and Matt was finishing a second slice, no salad (just can't deny a man a second slice when the pizza is good, and it looked great, but I'm not in my mid-20's like Lisa so I pick my spots for carbs and with Thanksgiving the next day, I was saving my carbs for that meal), and Matt said to me, "Dolly, when you said no thank you to donuts and dynamite, you said we'd bond but not over donuts, and now you've said no to pizza. Maybe this boy needs to take a hint."

 

Okay, that was more pathetic than cute or awkward, so I decided it was time to get him back to awkward.  And I knew saying something suggestive would do it.

 

"Matt, what if we bonded while eating something all natural, healthy, sweet and fresh and zero calories?"

 

"Um, sounds great?" He was confused. What I'd described didn't exist, at least not at Publix or any other grocery store during the holidays or inside the break room. "So what do you plan for us to eat that fits that description?"

 

"Why, Lisa, of course.  Leese, are you up for that?"  At which point Matt shock-sprayed his Coke Zero out, having been completely caught off guard, which was hysterical.  I knew the answer to my question, though Lisa hand'nt known the timing.  She asked me not long before that fateful Wednesday, "Dolly, when are you going to share your built for fucking body with Matt, he's in more dire need for mind-blowing sex than any other white man I know," and I'd replied, "Very perceptive, Lisa, how about you join me when I fuck him and we make it our own dirty little secret from Chad?" 

 

She'd considered it, then looked at me and put a hand on my knee as she said, "I've never slept with a married man, I guess there's a first for everything.  And why not with Matt, he needs it and he's such a good guy I know he won't be a stalker or anything, okay, yeah, and I get to do another three way with you, Dolly, yeah, I'm in!"

 

Oh the sparkles in her eyes!  Oh the mix of terror, thrill, and victory in Matt's!  Oh the wetness in my pussy, remembering this girl's mouth and hands on me, and how amazing it was to combine how she made me feel with a man's cock also bringing me to Pleasuretown.

 

Matt still hadn't answered when Lisa took his hand and helped him stand, and she kissed him lightly on the lips, no tongue, wrapped her arms around his neck and told him, "No one else will know, Matt, just us three, please trust us and say yes, there's no one else here and if you don't Dolly and I won't have a cock to share while we fuck each other's brains out."  Damn that girl could dirty talk.  She lowered her hand, and with slender, elegantly French manicured fingers rubbed the bulge in his jeans.  Matt's hands found their way to her hips, and I joined them, standing behind Matt, my D-cup tits pressed into his back, and I lightly nibbled on his neck.

 

"We'll send you home without any scratches, hickeys or marks.  But we do plan to empty your balls."

 

Lisa and I each took one of Matt's hands and walked him to my office.  We were in a high rise.  We had great views.  No one else was in the office.  It was perfect.

 

And it WAS perfect.  Pleasing Matt while on my knees, all while his eyes were on Lisa, slowly smiling and stripping for him.  Turquoise lacy underwire bra and matching thong, and no tan lines once those sexy underthings came off and were draped on his shoulders.  Usually I'd be annoyed to have a man pay so much attention to another woman while his dick was in my mouth, but Lisa is hot and the whole almost-spontaneous nature of this tryst was so exciting.  With my travel schedule and appointments for Dolly dates, I have a helluva lot of scheduled, planned, sometimes even choreographed sex.  Today we were winging it.

 

I didn't bring Matt to the mountaintop.  I slowly pulled from my lips his hard tool, an average six inch pecker, which truth be told is a fine size for sexual pleasure and why do guys get so hung up on being seven or more?  Hey, if I'm NOT massively sore from an eight incher making my pussy its own personal dwelling, I'm probably more in the mood for more sex later on.  Make sense?  "Did you want to strip my clothes off me, Matt, only fair since Lisa and I got to strip you."

 

He fumbled every single snap, button, zipper and hook.  His hands were shaking.  Lisa commented on  it as if he was decorating a Christmas tree, and I disagreed because if he was putting clothes ON me, it would be like decorating the tree, but stripping clothes OFF was more akin to taking the tree down, removing ornaments. Soon we were all nude, fully, no heels or anything, and Matt was savoring my tongue and Lisa was stroking his cock while tasting me, and then we swapped so she could kiss Matt and he tasted second-hand Dolly pussy.

 

I handed Lisa the condom and she playfully wrapped him, then we arranged Matt on the furniture, stopping to look and considering the layout as if we were interior decorators, and then we decided I'd mount first, reverse cowgirl, and Lisa kissed Matt, first on the mouth, then on the underside of his scrotum, then she tweaked my nipples and licked my clit while Matt thrust upward, and after all the stimulation that sexy slut and I had provided, I'm really proud that we got five minutes out of Matt before he popped.  He stiffened, he cried out, "Oh Fuck!  Dolly, fuck! Lisa, mmmm, shit, God damn, oh my God."  His body heaving for breath under me.  I dismounted, and we did some three way tender cuddling.  He started to tell us that he'd never done this or that, but we cut him off.  "Today is no questions asked, no secrets told or to be told.  Today you are ours, and when you go home you belong to your family and none of this will ever be found out or affect anything.  You deserve this." 

 

Then after a while, it was time for more. Lisa spoke up first.

 

"Now how about you lick my pussy, Matt, like Dolly said.  And while I'm just a B cup, that does make me all natural as well as zero calorie, and yes, fresh sweet and delicious like Dolly promised you." 

 

I stuck out my tongue at Lisa because she emphasized "all natural" when she said that to Matt. 

 

"Don't show me your tongue unless you're going to use it on me.  And first Matt gets to use his tongue on me.  Finger me, Matt, feel how wet I am for you."

 

Damn, girl, there she went again, that dirty talking young hot slut was going to steal my heart!

 

She laid back, actually reclining into me behind her, and Matt went down on her.  I loved how her back felt against my skin, my nipples brushing her flesh, as I squeezed her tits, and she turned her neck so that she and I could  kiss, and her nails raked my wide open thighs that were outside of hers and Matt took his time and eventually Lisa added her fingers on her clit to his efforts and it was so cool to hold her while she came and then Matt shocked us both by pulling out, pulling off his condom and shooting his cum on her sexy flat tummy. 

 

"That's so fucking hot, using me for your cum slut." Lisa said in between her post cum scream gasps for breath.

 

I didn't ask permission, I simply slipped out from behind Lisa, moved around and licked Matt's cum from Lisa's tight body.  I showed his seed, on my tongue, to both of them, then snowballed Lisa with a slobbery, cummy girl-kiss that will long be remembered.

 

Now, Lisa and I probably could have kept going all the way until the Thanksgiving Day parade started the next morning, but we didn't want Matt to be late and to be subjected to questioning by his shrew, er, I mean his wife.  "Matt, go ahead and shower, here's my pass key to the fitness center, we don't want you wearing our sex scents when you get home, go shower.  You've got your family waiting. 

 

"Uh, oh, right, yeah, that makes sense."  Still stammering.  He started, took a few steps, and I called after him, "but maybe go to the swag closer and grab a t-shirt and shorts to wear down there, don't get your clothes dirty but putting them on while you're still coated in our sex scents,  but then again you can't ride the elevator naked like you are right now, Tiger.  Then leave the tee and the shorts with me, I'll take them home and launder them and add them to my trophy drawer at home, and only the three of us will know.

 

And yes, Lisa and I fooled around while he showered and he came back sooner than we realized he would and walked in on us sixty-nining, which isn't my favorite position with a lady but it was fun and Lisa suggested it, and my thought as I said "sure" was "since I seem to be in the habit today of making my subordinates' sexual office fantasies come true today, why not?"

 

So that's my "Matt the nice awkward married man" threesome office sex story. Hope you enjoyed it, lovers.  Now send me emails and let’s make Dolly dates and build some memories that will be just between you and me.  And maybe Lisa, too, if we get lucky.

 

Now, if you're wondering, did Matt and I ever fuck again, the answer is "yes".  But Lisa didn't join us any of those times. 

 

 I offered to recruit her, but Matt told me, "Dolly, fucking Lisa was great, I'm not going to lie, but Dolly, I have nothing in common with a young girl like her, and you and I have common life experiences, perspectives, we've been married, we're parents, homeowners, tax payers, whatever, Even simply being old enough to remember when the second George Bush got elected and we didn't know for weeks how it was going to turn out, all because of our neighbors up in Palm Beach County and their butterfly ballots and hanging chad, it's nice to have small talk and feel like I'm with someone I could actually be with when we have our private time.  With Lisa, it’s just fucking, and sure it was amazing fucking, but  while I know you and I aren't a couple, it’s amazing to feel like we're a couple when you do make time for me.  You feel like a girlfriend to me when we hook up.  I don't want to get divorced Dolly, so don't take this the wrong way, but I love you, I mean, I love what you do for me, I love how you make me feel about myself, and I can't ever thank you enough".

 

So sweet, so well spoken.  Then Matt showered and went home. That conversation about how he preferred me as his GFE to Lisa was during a hotel room fuck Matt and I shared one time when our client prepaid for his hotel and then had a last minute cancellation of his trip. On that occasion, the client called and said, "hey, if you can use a hotel room for whatever, go use mine".  Funny how I took that as an invitation to fuck my fuck buddy. Funny too, only after he left did I realize ... Matt didn't seem awkward any longer.  It seemed fucking me and bringing me off and generally experiencing pleasure and happiness that Dolly dates deliver cured Matt of his stammering and awkwardness, and he seemed so confident now.

 

And confidence is sexy, too.

THE END

Purely fictional fantasy for your reading pleasure!

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