In the Office With My Older Boss: Pt. 3 [M21/F39] [College Student] [Older Woman] [Slow Burn] [Passionate]

[This is a part three follow up to my original story. I wrote this in a way that hopefully you can enjoy it on it’s own, but if you’d like to start from the beginning you can find the other stories in my profile.]

I find myself laying in bed again, using my eyes to trace the cracks in the ceiling above. It seems like this is a reoccurring moment for me these past few days. At least I slept a little better tonight than before. I find some solace in knowing that this time it’s not because I fear the consequences of fooling around with my boss two day’s ago after a few bottle of wine. Instead, it’s anticipation into another “late night” at my boss’s request.

Luckily when my head hit the pillow last night, the scenes of these past two days was enough to quietly rock me to sleep. Like sugar plum fairies dancing in my head, I reminisced on finally fulfilling years of fantasies for my much older, yet still attractive, boss. The college kid in me felt like I had won the lottery twice.

In the Office With My Older Boss: Pt. 2 [M21/F39] [College Student] [Older Woman] [Slow Burn] [Passionate]

[This is a follow up to my previous story. I tried to write this so you can enjoy it without the context, but if you’re interested you can find my other story here: https://www.reddit.com/r/eroticliterature/comments/xmzmtt/late_in_the_office_with_my_older_boss_m21f39/

I hope you enjoy.]

My eyes kept tracing the outline of cracks along the ceiling. My alarm would be ringing in a few minutes, but I’m already wide awake.

I barely slept last night.

My head pounded from the two bottles of wine my boss and I polished off in her office. I had made the drunken walk back to my dorm while my boss called a cab to head home. I would have offered her to crash at my place, but I had a feeling sleeping in a dorm room after the age of 30 is not appealing to some people.

I roll over. There was no way I was getting back to sleep. The images of yesterday still played in my mind. Thoughts of going down on my boss in her office late at night. Images of her reciprocating with her own oral skills. Like a movie replaying over and over.

Late In the Office With My Older Boss [M21/F39] [College Student] [Older Woman] [Slow Burn] [Passionate]

[Note: This starts slow. If you’re not into that and want to jump to the action, I made a break point with “—” to indicate where the action picks up. Feel free to jump ahead if the pace is too slow.]

“Good afternoon” I say to the security guards as I make my way to the elevator and on to the upper floors of the building. The guards wave back and say something, but I have my headphones in so I just smile in response. I look down at my phone. It’s 3pm and they’re probably just about to head home from their shift.

It might sounds strange walking into work at 3pm, but I didn’t work a 9-5 gig. I actually wasn’t even supposed to be here today. I’m a part-time intern here, originally picking up this job a few years ago during my summer break as a way to get some extra pocket change. It was a short walk from my college campus and I had very flexible hours. The work was actually pretty easy and most of the time I listened to music until I finally had something to do. All-in-all, it wasn’t a bad job.

She Discovers Her Inner Desires [Masturbation F29] [Cheating M28/F23]

When I kissed him goodbye today I held his lips to mine a little bit longer. Holding his head in my hands and looking into his eyes. I tell him “I love you!” waiting to hear him say “I love you, Jenna.” back to me.

It’s Saturday and my husband is working another irregular weekend shift. This doesn’t happen too often, but by now I’m used to these types of weekends. It’s just the nature of his work. I typically don’t mind them as they’re so infrequent and it helps to get a day to yourself. It’s a good excuse to curl up in a chair with a morning latte and a good book.

But I can’t fathom doing any of that right now. I just keep seeing him and her together in my mind. Laughing with each other. Smiling as they look longingly at each other. Fucking. I’ve never been know to be the jealous wife. In fact I’ve always trusted my husband. He’s been good to me and, honestly, he’s never given me a reason to think he’d stray. I used to think he felt the same way. Not only that I was faithful, but that he could trust me.

Her First Time is With Sara [F20/F19] [College] [Lesbians] [First Time] [Shower]

I can hear the sound of my heart beating in my ears. The feeling of my back being cooled by the cold painted concrete wall why my front is warmed by the steam radiating off the water before me. The feeling of little splashes of water tease my skin as the shower water pours over Sara’s shoulders. Her eyes locked onto mine. He hands have my body against the wall. This is it..

It all started at the beginning of the semester. I’m Anna, a third year English major who’s spent too much of her college life buried in books and not experiencing the world. Being the first in my family to college has always spurred me into dedicating most of my time to studying and school activities and very little time on parties or a social life. Which is fine by me, I don’t like alcohol and dating is just a distraction. At least, that’s what I say to myself.

I’ve always had self-esteem issues and maybe that’s why I buried my head in a book. Trying to protect myself from being rejected. Or worse, finally realizing that I’m just not attractive. I always thought I could be a knock-out with a little effort, but I just don’t take the effort to advertise. I honestly am not sure of myself, but that’s what made Sara so special.

A Couples Journey Past The Vanilla Sex Life – Pt. 2 [M30/F31] [27F/29M Swinger] [Married] [Bar] [Public Fun] [Bathroom Sex]

I decide I had waited long enough in the stall of the women’s bathroom. My wife had stepped outside a moment ago to check if the coast was clear and now I’m worried she got lost and forgot me here. I decide to risk rushing out. The worst that can happen is someone catches me and I fake being drunk, “What sign? Oh wow, my fault!”

Just as I’m about to open the stall door, I hear the bathroom door open and it causes me to remain still. A pair of footsteps make their way to my stall and I see my wife push the door open, followed by the cute bartender who served us drinks earlier in the day.

“Hey, meet Tina.” My wife says as she pushes me aside to make room for her and to close the stall door.

“Hey, nice to meet you.” It’s all I get out before my wife is on top of Tina. Their hands wrapped around each other’s bodies. They pull each other close and begin to lock lips like long-lost-lovers.

A Couples Journey Past The Vanilla Sex Life – Pt. 1 [M30/F31] [27F Voyeur] [Married] [Bar] [Public Fun] [Bathroom Sex]

It was my lucky night. My wife had decided to wear her sexy sheer blouse out to the bar without a bra underneath. I know it doesn’t sound as risqué as the type of things you see in a porno, but we’re not really the wild couple. Not that we don’t want to be, but we’re slowly migrating from the vanilla sex life of a new couple into the realm where we start to feel comfortable talking about our fantasies. And this was always one of mine. I don’t know why, but the idea of her standing in the middle of a dimly lit bar in her see-thru clothes. It wasn’t the idea of flashing everyone at the bar (although maybe that would be hot.) It was more about the fact that you wouldn’t really notice unless you looked. The fact that someone could see with a little effort was what really underneath, her wonderful tits are like a treasure. I’d be able to know who looked by the fact that they wouldn’t stop staring.

Getting Laid Off Isn’t Always So Bad – The Night Is Still Early [M32/F33] [First-Time] [Coworkers] [Hotel]

[Hi all. This is a continuation of my last story. Feel free to leave a comment and let me know what you think. I also love hearing suggestions and ideas. DMs and Chats are always welcome.

[https://www.reddit.com/r/eroticliterature/comments/wi7pkb/getting_laid_off_isnt_always_so_bad_the_first/](https://www.reddit.com/r/eroticliterature/comments/wi7pkb/getting_laid_off_isnt_always_so_bad_the_first/) ]

My hand wrap tighter around the silk scarf as I brace for my body to tighten up again. Tara has once again brought me to the edge of another intense orgasm and this time it was a really close call. I had to do everything in my power to hold back from showering her hand with everything I had in me.

“Oh god, I’m close again!” I blurt out to the dark void, getting Tara to quickly release me. The blindfold on my face makes it a little hard to know which direction Tara is sitting on the bed, but I can feel the bed move as she pulls back hoping to have once again prevented another close call. Riding the feeling of being so close and yet not cumming has become a ritual for the past two hours. After our wild time in the shower, Tara needed a little break from being filled. I’d love to take credit for her need for a respite, but, even with Tara implying that it was me in the shower making it hard for her to stand and kneel, I feel like this might also be the symptom of diving right into a wild day and night of crazy sexual adventure. Going 0 to 100MPH so fast tends to cause a little whiplash. We weren’t in our 20s anymore.

Getting Laid Off Isn’t Always So Bad – The First Night [M32/F33] [First-Time] [Coworkers] [Hotel]

[It looks like there was some positive feedback on my last story, so here’s the continuation. If it looks like this one is as enjoyable as the first then I’ll make a follow up to this as well. Just let me know. For anyone new to the story, this story doesn’t require looking back, but if you’re curious:https://www.reddit.com/r/eroticliterature/comments/wh5o7p/getting_laid_off_isnt_always_so_bad_m32f33/]
I stop at the door. Looking through the front window of a little cocktail bar in the lobby of our hotel I see Tara sitting alone in a tight fitted black silk cocktail dress. She really knows what to wear. I picked this hotel because I knew Tara always loved cocktail bars. Getting dressed up all fancy. Getting to feel classy. It made feeling naughty later on in the night all that much more exotic. I don’t disagree, but this was always one of her little fantasies. She always had good ones.
I walk in and cross the room to the bar. Sitting in the seat next to her I introduce myself. She acts polite, but uninterested. Like something else is on her mind.
“I couldn’t help but notice you look a little troubled.”
She barely turns her head my way. “Sorry, it’s just been a rough day.” I could tell by the empty drink glasses in front of her. She must have been thirsty.
“Oh? I’m sorry to hear. Trouble at work?” Tara would appreciate the double-entendre seeing as how we actually did have some trouble at work earlier today.
“Among other things.”
“Oh.. boy troubles?” She looks over at me. I struck gold.
“He let me go today. Over the phone. Didn’t even have the decency to say it to me in person. I guess I’m just not worth the hassle.”
I see where she’s going. Tara liked the idea of having a rebound guy. Someone to take over after a heart break. To put the piece back together, usually in the form of wild sex. The type to let loose. I’m not sure if maybe she’s always liked the idea of being that lonely girl at the bar. The one you see in movies that the main character walks up to and tries to seduce. She liked to be seduced. Something about the catch that gave her a thrill. In this case, she was making it a little easier on me. She was the heart-broken girl. Willing to bat an eye at any guy who would pay her with a compliment.
I knew she wanted me to butter her up. Not just with cheesy one liners and half-hearted poetry. She wanted me to be smooth. Tell her she’s the finest girl at the bar without saying it directly. I ended with how seeing her in that window was what pulled me in off the street. I knew what she wanted to hear. Maybe some of it was the truth.
The flirting continues at the bar and as the night goes on we begin to make it more and more obvious that we’d want to take this elsewhere. Since this was a hotel, no better place then to one of the rooms upstairs.
We step alone onto the elevator and punch the 25th floor. As soon as the doors close I push Tara up against the wall. Her hands dart behind my head and pull me in for a kiss. My lips locking against hers. I slide my hand between her legs and her back arches. She’s always had a wild fantasy of a passionate scene in the elevator. It the idea of only have a few moments of time to act out your wildest wishes. Kissing, touching, playing all confined in a window from when the door opens and when the door closes. And while you might pick the floor you never know if the time will stop before you reach it. Anyone could be calling this elevator. I can tell she was enjoying this moment a lot more than I was expecting. Her moaning built as the floor numbers ticked up and she was already in a deep passionate moan when we could feel the elevator start to slow down.
I couldn’t missing this opportunity. I kept my hands buried into her panties. Like a game of chicken. Would she stop me before the doors open, or will I be too scared to keep my hand there? Both of us knowing that anyone could be standing on the other side of those doors. How else can you make someone’s heart race faster when you’re already teasing them to the moon. The excitement was driving us both wild. And then, “Ding.” The doors slide open and I turn to look. It’s empty. Fortunately, or maybe unfortunately.
She holds me tighter as we walk down the hall. I can tell she’s loving every second of this. When we get to our room and open the door she hurries inside. She can’t believe this is happening. An actual night alone in a hotel room. What happens here, stays here. We’ll just leave an extra tip for the staff.
I enter the room and stare at the bed. This thing will be what hold us for a night of wild sex. I can already envision all of the fantasies we could play out. Like a kid in the candy store. I don’t know which one I want the most. I start running through a list in my mind, but her voice breaks my daydream.
“Oh, but first I need to shower.”
I pause. “Hmm. I guess we could use it.” I think as I remember we did just spend a whole day in the office. Most of it in an intense one-on-one exit and enter and exit interview. It wouldn’t hurt to freshen up. I guess I can go candy shopping a little later. My internal monolog is jolted when you yank my arm pulling me towards the bathroom.
“No. I mean, I REALLY need a shower right now because some a-hole played chicken with an elevator door. And now THEY’RE going to help me scratch an itch.”
I smile. “Wupps.”
It was a plus that this bathroom was equipped with both a soaking tub and a big standing shower. I might suggest when spend several years teasing yourself with a girl, you splurge a little on the scenery. She’s already naked and the water in the shower is steaming up. I barely have time to take off my socks before she pulls me underneath the water. I can feel the warmth of the water down my back being met with her wet body against my front. The experience is new and it excites even me. Seeing her hair get wet against her body. Like a sexy shampoo commercial, this girl could make any activity hot.
I realize that with water dripping over her body and the desire in her eyes, I wasn’t going to have any problem scratching her itch. We test the strength of the shower walls as I press her up against them, using it as extra thrust as I reach further into her. In search of her itch. I find a spot that makes her gasp. I know I found my rhythm. Each thrust slowly changes Tara’s face from wild passion looking for desire to a woman who is focusing on every inch of sensation filling her body.
I knew this was working. Tara struggled to keep in character and soon that wasn’t even possible. Her quivering and moaning showing that she had fully lost control of her roleplay. We’re no longer playing a scene. Instead it’s the two of us. Two people who spent years building a passion for each other that now are realizing it’s more enjoyable then the original fantasies they created. Remembering how much we’ve really wanted this and how long we had to wait for it. Knowing it was worth it. I tried to keep the roleplay going myself, but the look of pure emotion on her face let me know that she was already too far into her head. Welcoming every jolt of excitement she felt in her body.
Unfortunately the whirlwind of warm water and wet bodies had to end when I had to hold her tight to me as she tries desperately to recover from her third orgasm. I can tell at this point any wild escapades will have to happen in the horizontal position. We finish showering off and decide to move into the bedroom. At least the king size bed gives a lot of horizontal space to work with.

Getting Laid Off Isn’t Always So Bad [M32/F33] [First-Time] [Coworkers] [Office]

I was excited.

It was Friday in the office. The week was over. But that wasn’t why I was excited.

An email ticks in. Our division was shutting down. I had no more job. But that wasn’t why I was excited, either.

It was Tara. Tara was the reason I was happy to hear the news of the company finally closing us down. Now, let me explain.

Tara was the cute girl at work. She started when I started a decade ago when we were fresh out of college. Maybe it was that particular fact that made us great friends from the start, but we connected. We were through everything together. You never realize spending 40 hours a week with someone builds you into best friends, but that was us. Now, Tara and I weren’t really attracted to each other from the start. We were just out of college. Our first corporate job. We weren’t really focused on romance at the time. That said, I thought she was pretty, and she thought I was handsome.