That time I made my married, overbearing boss squirt all over her hotel bed [MF]

This happened a few years ago at my last job. I was a social worker for a small rural school district, enjoying a few days in the big city at a big annual conference. It is something I look forward to every year. It is an opportunity to get away from the small-town bubble, reconnect with old friends and colleagues and recharge.

This year, however, was different. My district had a brand-new superintendent that was the definition of intense, she wanted to learn all aspects of how schools support students, so she decided to accompany me to this conference to learn more about what it was that I did.

Dr. Newbold was an attractive, dark haired woman in her mid-40s with a husband in his late-50s and two teenage boys at home. She stood about 5’6” with b-cup breasts. Motherhood had softened her figure some, but only some, she was a former Miss Nebraska in her youth, and she cut a fine figure in a pant suit. She was always wearing pant suits.

At this point she was new, and I didn’t quite know what to make of her. She could turn on the charm with the public, but in closed-door meetings she came across as cold and ruthless. She often sat with her legs crossed and arms folded, tapping her feet with what seemed to be impatience.

I was crushed when I found out she would be tagging along. This was my escape, and this year I was chosen to speak at the conference, I hate to brag, but I am a good public speaker, my passion for my work really shines through. It isn’t uncommon for passionate-about-the-cause, flirtatious graduate students to seek me out afterward to talk about my topic, that conversation often lead to drinks at the hotel bar and usually ended with a spirited romp in my hotel room. Now all that was out the window as I had to show Dr. Newbold around and keep up professional appearances.

We met up at the registration table. She of course was dressed to the nines: red pant suit with heels to match complete with a light colored silk blouse. I tried my best to admire her figure when she wasn’t looking. I was rocking a tan suit, I’m not normally so formal at a conference, but if I’m going to stand in front of a room and present I’m going to look like I know what I’m doing.

She peered over my shoulder as I was looking at the conference schedule. I suggested we go to different breakout sessions in order to gain as much knowledge from the day as we could, but she was shaking her head before I could finish speaking, “We’ll go to the sessions together, I want to see what topics you think are important.”

My last attempt at getting away from her thwarted: and feeling like I was being tested, so I lead us to the first session on professional ethics.

The next few hours rolled by with Dr. Newbold by my side the entire time. Between sessions I introduced her to my colleagues in the field, she was warm and charming and looked very pleased when my friends told her she had a great employee working under her. By lunchtime she had loosened up and lost the suit jacket, she became much more open and talkative and over deli sandwiches we shared deep conversations about how we could improve how we help students in our district. For the first time all day I was glad she had come.

The first session after lunch was my time to present. My topic was building community partnerships and it went off without a hitch. As I worked the room I glanced over and saw Dr. Newbold and her beautiful blue eyes smiling up at me in the same way those grad students usually did. This gave me a surge of confidence and I finished strong. Even receiving some light applause as I finished.

As the session ended and I started gathering my notes, a group of grad students and a few professionals came up to ask questions and comment on my topic. A few passed me business cards with their cell numbers scrawled on them with an offer to grab a drink and “bounce some ideas off each other.” My heart sank knowing I was going to be sleeping alone tonight.

She approached after the small group moved on, “Great job!” She beamed at me as she touched my shoulder and I felt a spark… I attributed it to the cheaply carpeted floor, but she continued “you represented us well. I can honestly say I was moved.”

“I appreciate you saying that.” I wasn’t expecting that.

She looked around us at the slowly emptying conference room, “so what’s next? Are there any more speakers?”

“That’s it for the conference today,” I replied “there is an alumni mixer over at the bonefish grill, if you’re interested?”

She had grimaced before I finished talking, “I think I’m done with crowds for the day,” She looked like she suddenly had a idea, her head tilted as she said “tell you what, I was about to head over to the hotel bar for a night cap. Why don’t you join me? I think we have a lot we can talk about.”

There it was, I had my opening to make my exit from her authoritative presence and go blow off some steam, but there was something about the way she was looking at me. I was intrigued, partly because I had assumed by her public persona that she was someone who would never drink at a bar, and partly because it was rare for someone in my position to have the ear of someone of her authority. Let’s see what is down this rabbit hole.

“That sounds nice,” I replied, “I’m going to say hi to a few people, then I’ll meet you over there.”

…

What was originally supposed to be one drink turned into two or three as we sat at the mostly empty bar and talked about topics both professional and personal. Dr. Newbold (or “Rachel” as she told me to call her) was magnetically charming, I found myself wanting to entertain her. She had this habit of touching my forearm when I made her laugh. It wasn’t static electricity, she had me wrapped around her finger, and I was into it.

“So, real talk,” she said, pausing to take a sip of bourbon, “what does the staff think of me?”

“Uuuugh I don’t know, I pride myself on not being a gossip, and I’d never speak critically of my boss with my colleagues, it isn’t a god look.”

She took another sip and nodded while taking a few beets to think. “I can respect that, but even if you aren’t a gossip, you must hear it.”

“All of it.”

“Well if you’re only telling me, that isn’t spreading gossip, it is relaying anonymous feedback, don’t you think?”

“You could frame it that way.”

“So what are they saying?” I started shaking my head, “No names, no repercussions.”

I paused and considered. I would never step on this minefield normally, I don’t like to sugar coat things, so I try to be smart and stay quiet, but I decided to just go for it.

“Well… feelings are divided. You’ve brought a new energy and accountability, some folks are doing everything they can to impress you.”

She smiled, then gestured with her glass, “and the others?”

“Well,” I gathered my courage and took another sip “they say this job is a stepping stone for you, you have no commitment to the community, you’ll come in and focus intently on one area where you can improve some statistics that matter to school boards, you’ll add it to your resume and then jet out of here in three years or less.”

Holy shit, I said it.

She sat expressionless for a few moments, in my head I started wondering how many boxes I would need to pack up my office.

“Wow,” she finally said, finishing off her drink in one gulp. “Thank you for being honest with me, that’s the first I’m hearing this.” She paused, pointed at me with her glass “and what do you think?”

In for a penny, in for a pound. “Jobs here are stepping stones for anyone not born and raised here. We are an aggressively mediocre district, the culture can be backward and the locals take generations to trust newcomers. All that being said, I have colleagues who were useless actually trying to do their jobs now, so maybe a push out of mediocrity will be good for us.”

She nodded and touched my arm again, looking into my eyes “thank you again for your openness, you wouldn’t believe how much ass kissing I have to endure.” She turned to order another drink from the bartender, who informed us he was closing.

“Shit!” She said, disappointed, then she brightened up, “tell you what, I’ve got a bottle of Elijah Craig in my room, let’s head up there and finish our talk.”

My jaw must have hit the bar as she slid me her room key, “give me ten minutes,” She smiled at me as she left without waiting for me to answer.

…

Ten minutes, it turned out, was just enough time for me to completely overthink the situation. What was happening? Was my upstanding Christian wife of a boss asking me to enjoy a glass of bourbon while finishing up a professional conversation? Or was the beautiful older woman who has been touching and flirting with me all night asking me up to her room for some hot sex? I racked my brain as I finished my drink and watched the minutes tick by. When ten minutes had passed I gulped down my drink and went to the elevator.

I don’t remember the elevator ride or the hallway leading up to her room, but I distinctly remember what greeted me when the door beeped and I pushed it open. She of course had a suite. Her luggage was open on the loveseat, and there was a trail of clothing leading to the bathroom. The door was wide open and I could hear the shower running.

I stepped toward the bathroom and considered the situation. She knew I was coming and could let myself in, if she didn’t want to be suggestive, she would have closed the bathroom door at the least. I peaked in, she was under the flow of the water, running her hands through her hair. This was it, I said to myself as I undressed in record time. If this was a misunderstanding, well then it was a hell of a way to get fired.

I quietly opened the door and stepped into the shower, she hadn’t turned around but she had to know I was there. I reached out for her, my right hand on her hip, pulling her body against me, and my left snaking under her arm and cupping her breast. Initially shocked, she settled into my touch and pressed her body against me.

“I thought you might not come,” she said as she turned around and our bodies intertwined like two vines struggling for the upper hand while our tongues met and the hot water fell over our bodies.

I used the strength of my broad-shouldered, 6’ frame to assert control over what happened next. I grabbed a handful of hair at the back of her head and moved my mouth to her neck, then worked my way down her body, from her chest, to her stomach, then her thighs as I went to my knees.

She gasped as I put her left leg over my shoulder and brought my mouth to her pussy. She tasted delicious, unfortunately the shower rinsed over her and left her with very little taste at all. I lapped my tongue on her opening, alternating between trying to penetrate her with my tongue and sucking on her clit. She wasn’t shy about letting me know how it felt, as she moaned and encouraged me loudly. Between her volume and the amplification provided by the shower walls, the whole floor had to know what was going on.

After I felt I had her thoroughly warmed up, I got back to my feet and she kissed me deeply, “My husband has never done that,” she said between gasps as she caught her breath.

“What a wasted opportunity, you taste amazing” I replied, as I continued to admire and touch her body. “If he has never done that, then he probably has never done this, either.” As I turned her around, I got back on my knees and bent her at the waist as she leaned on the wall for support. I spread her cheeks open and took a moment to admire her swollen pussy and asshole from this angle. Then I buried my face in her ass and started eating her out from behind. Her moans picked back up, and became deeper when I worked a few fingers into her and started massaging her g spot.

The moan turned to a squeal when I started licking her asshole. I had never rimmed anyone before, but between her obvious sexual repression and the shower water flowing over everything it seemed like the perfect opportunity and she was loving it. She was grunting now, pressing her ass against my face, every few minutes her grunts would be interrupted with either “fuck” “ooooh” or “please.” Her rhythm picked up and her breathing quickened. Her pussy clamped down on my hand as her orgasm took over, I held her up as she groaned and her body shook.

As she started to regain her senses she grabbed my thick cock and looked me in the eyes “I need you inside me,” she pulled me toward her opening with the intent of inserting me from behind, but this is where the shower failed us. The hot water running over our bodies had washed away all of her lubrication, and pressing the head of my cock against her opening quickly showed us this wasn’t happening.

“Let’s get on the bed” She said as she pushed me away from her and hopped out of the shower. I took a few minutes to wash my face before I followed her into the room.

As I came into the room with a towel around my waist, I saw she was removing her jewelry. She placed her earrings on the bedside table, then went to remove her wedding ring.

“Leave it on,” I told her.

She spun around and gave me a mischievous look, “oh really?”

“Yes,” I winked at her.

“Hm… sit down,” she said as she pushed me into a chair. She crawled to me on her knees and opened my towel like she was opening a Christmas present. Her eyes lit up when she saw me fully erect “holy shit,” she said as she took me in her hand and eagerly rubbed and slapped my cock on her face to feel the weight of it. “They’re right you know,” she paused to lick me from base to tip, “this is a stepping stone job, I don’t plan on staying long. Otherwise I would never be doing this.” Then she turned her full focus to my throbbing member and took me as far into her mouth as she could. She had a couple inches left when she hit her limit and gagged. She didn’t give up though, in an impressive display she pushed through the gag and I felt the tip of my cock make the downward turn down her throat. It is one of those sensations that is slightly uncomfortable yet incredibly sexy and erotic at the same time. Tears caused her mascara to run as she gasped for air, “you’re so much bigger than my husband!” She said proudly before taking me back in her mouth.

Dr. Newbold’s blowjob skills indicated that she knew what she was doing, she wasn’t afraid to use her spit to lube up my cock, and she made sure to pay attention to my balls also. I watched her work and talked dirty to her as a way of encouragement.

“Damn boss, you really like sucking your employee’s big cock don’t you?”

She gave an emphatic moan and nodded in response. Her other hand was between her legs working on her clit. My cock never left her mouth.

“Dr. Newbold, you suck me so well, this can’t be your first big dick,” her eyes smiled up at me, “when was the last time you had a cock like this?”

She pulled my cock out of her mouth and slapped it hard on her face, had she picked up on how much I liked that? “Not since colle-“ the rest of her words were interrupted by her inhaling my cock again.

“Mmmm… Dr. Newbold, I like the way your wedding ring looks with your hand wrapped around my cock. What would your husband say if he saw you on your knees, degrading yourself for this younger, more masculine man?”

With this comment her hand started moving rapidly over her pussy a she fingered herself and deepthroated me again, gagging loudly before coming up for air “fuck! I need you to fuck me!”

“Then get on the bed, I’m going to touch you in places your husband has only dreamt of.”

She crawled on the bed, stood on her knees and waved me over. I joined her and we embraced in another hard kiss, I tried to push her into her back but she put a hand in my chest to stop me “nuh uh!” She said as she pushed me onto my back and straddled me. She rubbed my cock up and down on her clit, then placed my head on the folds of her pussy and slowly lowered herself onto me “uuughnyessssss” she said as she started to adjust to my size like I had scratched an itch that had been there for years.

To be honest, I wasn’t disappointed she wanted to be on top. I got a great view as she raised her arms above her head, savoring the sensations as I watched her tits bounce to our rhythm and I matched her thrust for thrust. It also left my hands free to explore every part of her body.

She picked up speed as her second orgasm built, pinned my shoulders to the bed and locked eyes with me as she dictated the pace. The sounds were wet and erotic. “Fuuuuuck, your huge cock feels incredible,” she said as she changed her rhythm, taking me all the way in and almost all the way out.

“Oh, are you going to cum on my big cock?” I asked as her eyes rolled back in her head, I could tell from her movements she was trying to get the head off my dick to hit a particular spot, so I started moving my hips in a way that helped make that happen. That was all she needed, her pace quickened and in less than a minute she was squirting and screaming and clawing my back while her pussy tightened up on my cock so hard it hurt. She rode out her orgasm until she noticed both of us and the bed were drenched and her expression changed to shock and confusion.

“Oh shit, what happened!? Did you cum!?”

I smiled at her “not yet, but you sure did.” The woman was obviously cock drunk.

“Yeah but… what!?” She looked around, confused, “you mean I did this!?”

“Fuck yeah you did, it’s a good thing your room has two beds.”

“Well, shit, that’s never happened before… and you didn’t cum yet?”

I smiled and shook my head, feeling every bit the sex god.

“Well come over here and let’s change that,” she said as she attacked me and we started making out again. We explored each other’s bodies more, and I maneuvered behind her into a doggy style position. She paused “I never let my husband fuck me like this, he’s has asked several times, but with you… I want to submit everything to you.” She said as she locked eyes with me and reached back to do just that.

“Is that right?” I replied as I placed the tip at her entrance.

“Uh huuuuuuuugh,” her response was interrupted by my cock entering her again.

I proceeded to fuck her deeply and deliberately. Not like a hyper fast jackhammer like you see in porn, with my even-paced, deep strokes I soon had won her over to team doggy, she talked dirty between thrusts while I held on to her hips and had my way with her.

“Oooh. Aaah. Yeah. Ooooh. Fuck. Your balls. Are slapping. My clit. Yeah. Please. Don’t. Stop! Ah! Yeah!”

I kept that pace, now focusing on making sure my balls slapped her clit with each thrust. My own noises must have changed, because she could tell I was getting close. “Where do you want to cum?”

I pondered the thought for a few minutes then pulled out and said “turn around” and before I could blink she had flopped on her back and put my cock back to where now I was fucking her in missionary position. I locked fingers with her and raised her arms above her head, laid my body on hers and whispered in her ear “I’m going to spray my seed all over your body, it will be my tribute to your sexiness.”

She kissed me deeply then closed her eyes, “Give it to me,” as I kicked into overdrive and passed the point of no return. I pulled out as I began to cum, the first spurt hit her stomach, then the second rope shot out with such force it surprised me and landed on the headboard behind her. The third hit her squarely in the forehead, and the rest coated her stomach and tits.

“Oh whoa!” She said as she descended into giggles and rubbed my cum into her skin. “That. Was. Incredible!”

After taking a few minutes to bask in the afterglow, I recovered my trail of clothes and made a polite exit. I made it back to my room and promptly passed out from exhaustion.

When I woke up the next morning the text alert light was blinking. “I called down to the front desk and arranged for a late check out. Grab some breakfast and get over here.”

Yes boss.

Source: reddit.com/r/gonewildstories/comments/k4ug50/that_time_i_made_my_married_overbearing_boss