I [M] encouraged my officemate [F] to let her BF finish on her face … then later I did too.

TL:DR: I encouraged my office mate to let the guy she was dating finish on her face … then I did it too.

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Tara and I were in grad school together and shared an office — basically they’d put 4 PhD students in what was one professor-sized office.  She and I often found ourselves there alone together and became very close friends over a few years.  We were both in our early-30s and I’d been married for a few years with a very happy marriage.

The story really starts when she and her long-time boyfriend broke up.  They’d been dating nearly 10 years, and I think it basically ran its course, but it’s still traumatic when such a long relationship ends.

So as part of our friendship, I was consoling her and helping her through the end of her breakup. Just the usual telling her how great she was and letting her know it’ll all be okay.  Then as she started dating again, I was kinda giving her the “guy’s” perspective on dating since she hadn’t really dated in 10 years  … which led to giving her the guy’s perspective on sex.  Tara was definitely not inexperienced, sexually, prior to her long-time BF, but things are different at 30 than in your late-teens/early 20s.

It was clear she was enjoying being single and dating (and sleeping around) and she’d even tell me about some of her hookups — which I definitely enjoyed hearing about.  But it was just fun conversation, totally platonic.  It was also clear that she really loved giving oral sex and took pride in her talents. She even mentioned that she could usually deepthroat.  A few times she said how she’d blow a guy on a first date, even if she didn’t foresee a second date, just because she really loved doing it and showing off her abilities.

I know that every guy loves blowjobs, but I **really** love blowjobs, so her enthusiasm for giving was hot to hear about.  I was definitely living vicariously through the guys she was hooking up with.  My wife was still giving me head — but it sounded like Tara was both the more talented and more eager cocksucker.

It was clear during these chats that we had a lot of other things in common sexually, too.  She tended sub, I am pretty dom.  We both loved dirty talk including finding some name calling hot.  She loved big guys, etc.  The things she loved were the things I loved to do. So as you can imagine, most times when I masturbated during this time, I was thinking of Tara.

This went on for a while, her dating different guys and telling me some of her tales and sometimes asking advice or the guy’s perspective.  Of the men she was dating there was one, Dave, who seemed to be easing into boyfriend territory, and we were chatting one day about this guy and she said “Do many guys like to finish ON their partners?”

Now Tara was pretty sexually experienced, so this question kind of confused me — just because I assumed sexually experienced women knew most men liked to do this sometimes.  So I said, somewhat confused,  “Um – yeah — why do you ask?”

She explained that every time they had sex, Dave liked to pull out, take off the condom and finish on her — usually her butt or stomach/boobs depending on the position.  I explained that Yes this is very common for guys , especially if you’re having sex with condoms because cumming in a condom sucks.  I also mentioned that I was surprised she ask that — because most guys find seeing their cum on a partner pretty hot. I was surprised this was new to her.

She said “Oh — [her ex] pretty much just finished inside me or in my mouth every time.  He really liked finishing in my mouth even after sex.”  She was killing me — that’s my favorite.   Then she said “Do you often finish ON Rebecca (my wife) — and like where is your favorite place?”

I said “Yes, we don’t use condoms anymore, so I finish inside her most of the time, but sometimes it is really hot to see it on her, especially when I think I’m going to cum a lot.  And I kinda do it everywhere depending on the position.  You know, her butt or boobs.  But honestly my favorite is probably finishing on her face.”

Tara said “Oh my god! Are you serious?!”

And now I’m thinking “Fuck, she probably thinks I’m a misogynist or something.”  So I start to backtrack a little and try to explain. She realizes what I’m saying and cuts me off “No!  No!  I think that sounds SUPER hot …. do you think Dave would want to do that with me?!”

I laughed, hard, and probably fidgeted a bit to cover my growing erection and said “Yeah, if he loves cumming on your boobs all the time I guarantee he’d love an invitation to finish on your face …. but i think you should be careful …because you’re clearly enjoying being single and playing the field right now … and if you tell him to finish on your face, he might propose.  And I’m not sure you’re ready for that sort of commitment.”  She laughed and we started talking about something else.

So fast forward a week or two, and we’re in the office alone together and she said “So I saw Dave again last night … “.  She explained, laughing, that they went out and when they came home were having sex and she was riding him and when she thought he was close, she said “Tonight I don’t want you to cum on my tits — I want you to cum on my face.”  And apparently he just came — right away, right there, in the condom.  He told her how hot that was – and he definitely wanted to do it, but he needed a little more warning next time!

So Tara is laughing telling me this — and she clearly learned how hot Dave thought it would be. She was clearly one of those women who took pride in doing the little things to turn a guy on and make him cum extra hard.  And no doubt she was loving the effect these stories had on me. I tried to keep a poker face, but her stories were turning me on more and more.

A few days later she called me, fortunately my wife wasn’t home at the time so I could chat freely, and she said she and Dave had gone out the previous night … and this time she wasn’t taking any chances in getting to experience her first facial.  She said she was blowing him and made sure early on to say “Remember, you better finish on my face this time.”

So I say “Did he?!”  She said “Yes … alot!”.  Me:  “How was it for you?”

I’ll never forget what she said next.  She said “It was incredible. It was so hot!  Do you think a guy would want to finish that way every time!?”  Instant erection.  I laughed and changed the subject lest I say something I might regret.

I mean women who love sex are hot.  Women who love cock are hotter.  But women who love CUM? The hottest!  And here was my adorable office mate telling me how much she loved cum.  No one would’ve guessed this.

It wasn’t a coincidence that  night when my wife and I were having sex that night I left the bathroom light on for a little light and gave her a facial.

One more story before the story gets to Tara and me together.  As I mentioned, Tara was seeing a few different guys during this time and really enjoying her freedom and exploring and all the attention.  Another guy she’d told me about was a guy I played basketball with sometimes, kinda of ni the fringe of our circle of friends.  Tall, lean, really good looking guy — I remember he had an amazing jumpshot.  He had a girlfriend but had been hooking up with Tara on the side — I learned from her that the GF was a bit prudish.  This bit, by the way, occurred after her first facial with Dave.

She told me how they were out in a group one night, including his GF, and their favorite basketball teams were playing each other and he made a joke that they should make a bet on the game.  Tara whispered to him when this GF wasn’t  nearby, “How about the winner gets to cum on the loser’s face?” She told me his eyes lit up and he accepted the bet VERY quickly … and an hour later he won the bet.

Tara was telling me this after the bet, but before he could cash in, since they were out in a group that night.  Apparently he’d told her on the phone later that was a huge kink of his, but his current GF would never let him.  So he was very much looking forward to when he’d cash in on the bet.  A week or so later she tells me they hooked up … and apparently he’d been “saving up” and gave her an absolutely enormous facial.  She even told me how they went into the bathroom together so she could see herself in the mirror and how hot she thought she looked with it dripping from her face to her boobs.  She was killing me!

Still it had all been platonic between her and I. Just two really good friends swapping stories.  Until our friend Jeff defended his dissertation.

Grad school can be pretty grueling and we all grew pretty close doing our PhDs together, so it was a big celebration anytime one of us would successfully defend.  So when our friend successfully defended that afternoon, as usual he went out to dinner with his dissertation advisor that evening — but then a bunch of us students would get together to really celebrate.

Since this was a weeknight and she knew we’d be out late, my wife told me to go without her.  Plus she’d definitely have more fun home alone than just having to listen to us rehash  war stories and inside jokes.

The bar where we were meeting was close to Tara’s apartment, so the plan was I’d just park at Tara’s (who my wife knew well) and she and I would walk over together to join everyone.  My wife has never been the jealous type, so this was no big deal.

We met up and partied and celebrated for 3 or 4 hours, having a great time with friends we’d known for 4 or 5 years.  Then at the end of the night I walked Tara back to her apartment to drop her off and get my car.  We were chatting, both a bit (or alot) buzzed, and I told her how much fun I’d had getting to know her so much better this semester.  That I really valued our friendship and it’s super fun to me that it can be so hot — and stay platonic — and that her right guy would for sure come along because she’s such a great catch in so many ways.

She said, I forget precisely how, but something like, “Well until he comes along … I wouldn’t mind if this wasn’t quite so platonic.”  It took me a second to process…because I’m usually oblivious to when a woman comes on to me.  I’d obviously thought about this many times, and beat off thinking about Tara’s oral talents many times lately.  But actually doing it hadn’t crossed my mind. Cheating had never even occurred to me.

***** SEX STARTS HERE for the Impatient ***********

I paused and looked at Tara … “Do you mind if I come inside with you then?”

Next thing I know we were in her apartment, in her bedroom.  After some kissing and making out, she knelt before me on the rug at the foot of her bed.  I’ll never forget it. She was wearing a white bra and still had her jeans on.  I remember looking down at her pretty face and her cleavage in the bra.  Then she took my cock out ….  I had beat off to this many times in the last month or so… and this was a big step for me, I’d never cheated before.

I was hard as could be by this point and she took half of me.  I’m 6’6 tall and let’s just say everything is proportional. My wife can’t suck very much of me cause I’m pretty thick too, but i love the way she sucks those first few inches.

But Tara took half of it in the first motion. FUCK.

She kept bobbing, her mouth was so wet, and I kept telling her how hot she looked with a big cock in her mouth.  I told her how I’d beat off to this so often ever since we started talking about our sex lives together. She worked her way down my cock until there was about an inch still visible.  Then … goddam I will never forget this … she paused there, reached up and took my hand, and put it on the back of her head.  “FUCK … you want my help to take it all, Tara?”  And she nodded the cutest little nod with almost all of my cock in her mouth.

I put my other hand on the back of her head, too, and I pushed my hips slowly forward at the same moment I pulled the back of her head toward me.  I heard her gag and looked straight into her eyes to make sure she was ok. I’d never been deep throated before.

Slowly I kept easing back then easing more in … until her lips were at the base of my cock.  I looked down at her face and said “FUCK Tara.  I never thought Id see my entire big fucking cock disappear into a slut’s mouth.”  (Remember I knew she loved dirty talk).

Hearing that, she quivered and moved a hand inside her pants and I started using her mouth.  Watching her pretty face, watching her tits still in her bra.  I was getting close and pulled out, cock smacked her face, and said “Are you a good girl that swallows? Or a bad girl that wants it all over her face?”

She looked up at me and said “I’m whatever you want me to be … but I know you want me to be a bad girl.  So cum on my face.”

It took a lot for me not to just explode right there.  But one of my kinks is I love to see how wet a woman gets from just sucking me.  So I said “I AM going to cum all over your face  … but not until you cum on mine first.  Get on the bed.”

When she stood up I unhooked her bra, she undid her jeans and laid back on her bed.  I pulled her jeans and panties off and started sucking tits. They were bigger and fuller than my wife’s or past girlfriends’, so I spent some time there, but I was anxious to taste her.

I moved down and knelt between her legs — which she was opening invitingly.  I moved one finger around the bottom of her opening and she was soaked. I slid a finger into her easily and curled it upwards, finding her gspot.  Then I just used my finger tip to circle the perimeter of her gspot as she gasped.  Looking up, over her tummy, between her tits, looking at her face, I said “Goddam — I love how fucking wet you are just from sucking on my cock.  Will you cum on my face for me?” She panted yes as I massaged her gspot more.  Then I used my other hand to spread her lips and slide my fingers, in a V, upward to open her hood and expose her clit.

I slid my long narrow tongue down the left side, under, and up the right side of her clit. Then down the right, under, and up the left side.  Making U’s, slowly back and forth, barely grazing her clit as I did.  Testing it to see how sensitive her clit was.  She was trying to grind into my face.  Then I moved my finger inside her to the very center of her gspot and pressed and at the same time curled my tongue into a U … and slid it down over her clit and bobbed my head.  Short shallow bobs so my curled tongue slid up and down her clit.  My curled tongue like a tiny little pussy to envelope her clit. Bobbing my head to literally fuck her clit with my curled tongue.

She didn’t last long as I bobbed faster and massaged her gspot more firmly. She started bucking , grabbed the back of my head, and started cumming. I kept licking for a second then eased off her clit but increased the pressure from my fingers on her gspot and she kept cumming hard.

I was still hard as fuck and my first urge was to bury myself inside her.  I’m so used to penetrating my wife as soon as she cums from oral. But as odd as it sounds, I just wasn’t ready to fuck someone else.

I moved up, letting my cock fall between Tara’s big tits. I had my palms and outside three fingers on each hand on the outsides of her tits, letting my thumbs and index fingers pinch and roll her nipples as I pushed her soft tits together around my cock.  She leaned her head forward and I’m long enough she could just suck the head on each upstroke.

“Fuck Tara — I’ve been beating off thinking of this ever since you took your first facial.”

Then she told me she was thinking of me the first night Dave finished on her face.

I fucked her tits for a minute but needed her mouth again, so I moved up and just fucked her mouth, straddling her as she was on her back.

“You are so fucking hot — and you’re gonna look even hotter with my cum all over your face.”

I pulled out and told her to suck my balls as I stroked.  She was sucking my balls and mumbling to cum on her.  I pulled back and smeared some of my precum across her eyebrow, then lowered my balls back to her mouth and kept stroking.
The moment came and I growled and pulled back and aimed right at her.  I milked my cock, squeezing it tighter as I moved my hand from the base to the head … and exploded.  Rope after rope across her face.  Her mouth was open as I came and after a few more ropes I pushed my cock back into her mouth.  Maybe my favorite part of the facial is seeing my cock in my partner’s mouth after she has my cum all over her face.

I enjoyed the glorious view for a moment, while she sucked the last bit out of me and while I caught my breath.  I was spent.  I rolled off and leaning on her side, kissed Tara. Apparently I was the first guy to kiss her after a facial which she loved.  So I kissed her again.

Then I said “Hold still, I’ll grab a wet washcloth and be right back.”  She said “No, I want to see it, too.” 
So I used my thumb to wipe some of my cum away from her eye so she could open her eyes and we went to her bathroom together.  I remember standing right behind her – since I’m well over a foot taller than her — looking at us both in the mirror.  My cum covering her face, I pressed my softening cock into her back and squeezed her tits from behind.  I could see her look at herself in the mirror, then looked up at my face in the mirror and smile.  The best facials are the smiling facials.
“You’re unbelievable.” I said.
“Our secret?”
“Our secret,” she said.

Source: reddit.com/r/gonewildstories/comments/ipvhjx/i_m_encouraged_my_officemate_f_to_let_her_bf