The wind-driven rain pounded against the tall office windows as the darkness of that cold fall night crept over the grey horizon. Even from three stories up, I could see the parking lot was already flooding and the drive home would be abysmal. I heard the sound of glass clinking in the small office kitchen and then the sound of heels clicking their way toward my desk. Jennifer, 37, stood before me, a bottle of gin and two rocks glasses in her hands, now looking more beautiful than ever at the end of a long week. Jennifer had long blonde hair, bright blue eyes, the perfect smile, and pale white skin. She was medium height with a thin build, but carried a few extra pounds in her breasts, stomach, hips, and ass. To me, she was the epitome of a cougar.

"Care for a drink?" she asked.

"Sure, there's only an hour and a half left and I am ahead of schedule for next week," I replied.

She quickly poured a nice three finger pour for the both of us. Jennifer, 37, and I, 27, had worked together on and off for the last four years. I was constantly being moved around our company to assist with different projects, so we never had the opportunity to get to really know each other until recently. She was always very friendly with me and occasionally helped me out with various tasks, but most of our professional relationship was spent in passing or over quick work calls and texts. About three months prior, I had been assigned to her office on the third floor to cover the workload of the team that had been laid off due to the poor economy. Jennifer, myself, our boss, and one other employee, were all that remained of the third floor. I didn't mind though, as it came with a substantial pay raise for us and a private office for Jen and myself to share.

Over those three months, Jennifer and I quickly became close friends despite the age gap between us. She and I spent 8 hours a day together and learned everything there was to know about each other. She had been married for a few years in her early 20s but her ex-husband left her for another woman. She didn't have any kids and lived the single life for a long time, dating a little bit here and there. She had finally met a man that seemed to be the perfect fit and was with him for a year before he became abusive toward her. Jen ended the relationship about a month before we started working together. Similar to Jen, I had also been in a year long relationship that unfortunately was coming to an end. As we sipped on our gin, Jen asked me why I thought it was ending.

"It's just a feeling I have... She has been so distant lately," I started, "I really do adore her but I feel like she and I both want very different things in life. She's always out with her friends and claims to never have time for me between work and her personal life. I mean... I'm her boyfriend... I AM her personal life and I haven't seen her in two weeks. I feel like I adore her more than she adores me... you know?" I took a sip of gin and continued to complain, "It's probably better we end it anyhow before it goes on any further... besides, she is so lousy in bed. Let it be the next guy's problem."

"Oh really?" Jen's eyes flashed with excitement, "Do tell."

We spent the next hour and a half talking about bad sex stories, past relationships, and eventually got on the subject of our kinks. I mentioned my list of kinks and ended on one of my favorites, squirting.

Jen's eyes flashed again, "I'm a squirter."

"Oh really?" I replied, "I'd love to see that."

"I am sure you would... ask your girlfriend though. Maybe she's holding back. Plus I am four months out from a bad breakup... I am vulnerable... you shouldn't be preying on me!" she joked back harshly, shutting me down.

I didn't press any further and felt that I had overplayed my hand. The conversation turned tame again as we sipped a second glass of gin and started to pack up for the night. The rain was really coming down outside and I didn't hear my phone vibrate. Jennifer saw the message pop up from my girlfriend saying "We need to talk..." and motioned for me to look. Maybe it was the gin, but my eyes immediately got misty and I choked up. I didn't want Jen to see me like that so I walked into the restroom and wiped my eyes.

After a few minutes I heard Jen behind me as I had left the door open, she asked if she could hug me. We embraced and for the first time, I felt the curves of her body that she so cleverly hid within her professional attire. I felt myself melting into her arms, her embrace was so warm and inviting, the scent of her perfume was intoxicating. She could feel me, vulnerable against her, about to have the longest, worst phone call on my drive home, a call we had both experienced before. Jen's hand came up to my head, pressed it into her breasts, then she kissed me softly on the cheek.

As she did, she whispered..."I haven't been this turned on in a while... talking with you tonight made me so wet, I don't even need to squirt." She winked at me with a devious, yet affectionate smile.

Jen motioned for me to back up and as I did, she slid a black lace thong off from under her tight pencil skirt and tossed it to me. It was soaked and smelled softly of her pussy. She told me to keep it for the weekend, in case I needed something to comfort me. I thanked her, but handed them back, letting her know that I still had a girlfriend, for however short that may be, and that I didn't want to have that in my work bag should I be seeing my girlfriend in person. She admired me for a moment, taking them back and placing them in her purse respectfully. We walked out of the office together and in the elevator she kissed me goodbye on the cheek, wishing me luck once more.

We ran out into the pouring rain to our respective vehicles and waved goodbye. I started the worst call of that year to my soon-to-be ex. She and I talked for a few hours, hashing things out and fighting over the stupidest stuff. It was late by the time it was officially over and I was exhausted. I got into bed, checking the texts I had missed while on the break up call. Amidst the typical ones from friends and family was a single text from Jennifer. "How did it go? You ok?" Even in my moment of deep depression, I felt a lightning bolt of happiness seeing that Jen was wondering about me. I replied "It's over... but I figured as much. I'm hanging in there, pretty beat up about it. Going to get some sleep." I rolled over just as Jen sent another text, "Bet you're wishing you took my thong now lol... I am truly so sorry, get some rest and call if you need anything."

The next couple days were a blur. I met my ex to exchange stuff we had left with each other and we said our final goodbyes. I spent the rest of the weekend drinking with friends because I had learned that my ex was already seeing someone new. Then, late Sunday night, I was finally alone and in the middle of my own personal pity party, when Jen text me again. "You ok? I wanted to let you know, I wont be back to work until Wednesday, they assigned me to another project the next two days. Can I buy you lunch on Wednesday?" I replied that I was a little depressed, and joked that she was adding to it by leaving me for two days, but that I would love to have lunch with her as we usually did. She sent some laughing emoji's and jokingly asked if she could make up for it. "I doubt anything would cheer me up right now." I replied honestly. She took a moment to reply... then text, "Maybe this will help... In my defense, you said you wanted to see..." I felt myself tighten with anticipation as a video popped up on my screen. I pressed play.

The camera was placed directly between Jennifer's silky bare legs as she laid on her white bedsheets. Her tight pink pussy sat perfectly in frame, her tiny clit was swollen and red from pressure. Peeking out between her two cleanly-shaven, thin pussy lips was the tiniest piece of black fabric. As the video played, her perfectly manicured hand with her bright red nails reached down between her legs giving her clit the lightest rub and then grasping the black fabric. As she pulled ever so slightly, I could see the fabric slide slowly out of her hungry pussy. She moaned in the background, revealing more of the fabric. As I saw the pattern of the lace, I instantly knew it was the same black thong she had soaked on Friday night. I watched with pure desire and intensity, feeling myself get hard. As Jen pulled more and more of the lacey thong from her pussy, she began to leak. A little dribble at first, but as the last bit of her thong came out from the grasp of her pink lips, her body tightened and she squirted a large spray across her sheet, thong, and hand. She tightened twice more, letting out two smaller, softer squirts all while moaning beautifully in the background.

The video ended there. I voraciously watched it four or five more times, getting harder and harder. I wasn't going to stop until Jen's text diverted my attention. "Like what you see?" I immediately responded with compliments and asked if I could call her. We had never talked that late before and certainly never about anything other than work. My phone rang immediately and I answered hearing Jen's breathy voice on the other end... she spoke in a way I had never heard before. There was zero small talk and we jumped right into phone sex without missing a beat. We stayed on the line until 2:00AM that night, cumming over and over with each other.

Over next two days we spent any chance we had texting and calling each other. Our lunch breaks coincided and we spent an hour on the phone flirting and talking all about our days without each other. Each night was spent with phone sex until we passed out. On Wednesday morning, Jen called before work. Her tone was serious but caring; she explained that although we had been having fun together, we should probably try our best to keep it professional at work that day. I agreed, and we planned to go out to dinner and then to meet at her house after work.

Upon arriving to the office, we both awkwardly said hi, gave each other a quick peck on the cheek and resumed our duties as if nothing had happened. The rain storm had cleared over the weekend, but the day was still overcast and horribly chilly as was typical for the mountainous fall weather. Despite the frigid weather, I couldn't help but notice that Jennifer was wearing a loose fitting red dress. My imagination roamed for the rest of the morning. Around 11:00AM, our boss entered to check in with us both and assign a few tasks. He stated that he would be in meetings and conferences for the rest of the week, which was not unusual and asked us to lock up at the end of the day. We acknowledged and continued working. The only other employee on our floor, Linda, had a small office next to ours and spent the morning distracted on the phone with work calls.

Jen and I did not speak other than for her to take my lunch order. As the minutes ticked by, despite the silence, the sexual tension built to the point that any bystander could have easily identified it and cut it with a knife. Upon the lunch hour, Linda knocked on our office door and stated that she was heading out for the rest of the day to meet with clients. We would be on our own. Linda offered to lock the office door on her way out so we could enjoy our lunch in peace. Jen nodded and we bid her goodbye. It was not uncommon for us to lock the office during lunch hours or during field work. With the office locked and the two of us alone, the awkwardness grew. I barely touched my food, same as Jen. We made some casual small talk, and flirted about our plans for the evening. 5:00PM could not come soon enough. The office was overly cold, so I offered to raise the thermostat. As I did, Jen dismissed herself to the restroom. I returned to my desk, picking at my lunch and trying to complete the extra assignments left to Jen and I. After 10 minutes or so, I heard glass clinking in the kitchen and Jen's heels clicking back toward our office. Once again, she cradled a fresh bottle of gin and two rocks glasses.

"I though this might help ease the tension?" she flirted, pouring glasses for both of us.

"We have a lot of work to finish up, do you want to knock it out before we indulge in drinks?" I answered with the cautiousness of youth.

"I think we will be more productive if we can relax and address the elephant in the room," she replied coyly. I smirked at her response as we cheered our glasses.

"Fair enough..." I commented, "So what is the elephant in the room? Our date tonight?"

"Yeah, that... and... well, I am a little uncomfortable," she replied. A look of fear crossed my face, not catching on the playfulness of her voice. She smiled mockingly at me and sat herself on the desk just in front of me. I became uneasy with how close she was to me, sitting directly in front of me in the office. The tall office windows felt like gigantic aquarium walls, begging anyone outside to look in and observe the moment. The florescent lights burned brightly, defeating the privacy tint on the windows due to the gloomy weather outside. Jen sensed my apprehension and took me by the hand.

She led me out into the main office hallway and motioned to the locked front doors. The motion sensitive lights of the rest of the office were already disabled, as no one had walked in the entrance in for over 30 minutes. She casually placed her hand on the small of my back and rotated me around to reassure me that no one else was present. Applying light pressure, she urged me back into our office and closed the door behind us. I was so nervous that I didn't even hear her slide the bolt lock behind us. As I returned to my chair, I snapped back into consciousness as she clicked off the lights. Our office grew dim immediately, and the grey light of the overcast sky outside seemed exponentially brighter than our now dark office space.

"Baby, I just text our boss and he will not be back until tomorrow morning, and Linda already emailed me documents for her first client meeting of the afternoon. We have no deliveries scheduled and we are completely alone until the end of the day," Jen reassured me. Over the last three months we had dozens of days alone like this and I had never given it any thought. However, this time, it was very surreal to me. I finally realized that with the lights out and the doors locked, we were in complete and utter privacy. I relaxed slightly, and even more so as I took a big sip of gin. Although I had not considered our age gap before, it was in this moment that I became very aware of how young and inexperienced I was. While at first this revelation shook me, I quickly began to see how attractive it was to be with a mature, experienced woman. Just as I began to feel my bones relax, a light pitter-patter of rain began tapping into the windows, allowing me to ease deeper into my swivel office chair. Jen and I sipped from our glasses as she reassumed her position, sitting on my desk just in front of me. She poured us another stiff pour of gin and we clicked our glasses, cheering to us.

"As I was saying," Jen started softly, "I am a little uncomfortable."

"Why?" I asked naively, still not catching on to her coy tone of voice, "Because of our age gap? Or because of the office? Or because..."

"No Silly," Jen cut me off, "Because of this..." Jen lifted her legs up to rest her feet on the arms of my office chair. With one hand she lifted her dress, the other still clutching her glass of gin. As her dress cleared my field of view, I was immediately met with the same picture of the video she had sent me only a few nights before. Her pale, shaved legs were spread wide with her bare pink pussy exposed in the center. A tiny black piece of fabric peeked out at me from between two perfectly shaved and manicured pussy lips.

"Can you help me get it out Daddy?" Jen asked flirtatiously.

I was speechless. I nodded and reached for the fabric, which I immediately recognized to be the same thong she and I had played with before.

"No Daddy," she commanded, "Use your mouth." Jen's bright blue eyes flashed yet again as she commanded me softly.

I leaned forward, setting my glass on the desk. My hands hungrily gripped her thighs as I placed my head deeper into her dress. I could immediately smell the light scent of her pussy as I grew closer to it. It was unlike any other I had experienced up to that point. Her scent was soft, mild, sweet, and inviting. It was unlike so many I had eaten before. I placed my lips around the fabric and pulled softly. As I did, she began to leak, just like in her video, only this time, I was there to taste it. I pressed my tongue against the base of her pussy, my lips still gripping the soft black lace of her thong. The taste of her squirt was so light that I felt like I was drinking sweetened water. She moaned my name as she felt me both pulling and lapping up her bodily nectar at the same time. As I pulled more of the lacey thong out of her, she squirted harder and harder. I did my best to try and catch what I could, but most of her juices ended up spilling all over the front of my desk. As I pulled the thong from her, I noticed I was coming to the end of it. She moaned that she was going to cum.

I quickly wrapped my hand around the thong, and placed my tongue at the base of her pussy with my mouth open wide. Just like the video she sent me, when the thong came free from her hungry lips, she tensed up and her pussy squirted straight into my open mouth. I was barely swallowing the first bit when she shot a second and third gush of squirt into my mouth. I pulled my head from under her dress, covered in her love juices, smiling from ear to ear. Jen immediately slid off of the desk and kissed me passionately, despite me being covered in her pussy juices. It was our first real kiss. At first, she pressed tightly against my lips, not wanting to let me go as she continued to orgasm on me. Then as the waves subsided, we sank into a soft but passionate kiss together, finally feeling the deep affection we had developed for each other after months of friendship.

Jen pushed my chair back until it hit the wall behind me. She knelt to the floor in front of me and began to unbuckle my belt. Once undone, she unbuttoned my slacks and untucked my shirt that was now perfumed with a mixture of my nervous sweat and cologne. She unbuttoned it slowly revealing my hairy chest, licking and kissing up and down my torso. She eventually worked her way back down to my waistline where she helped me shimmy out of my slacks and boxers. They fell to rest around my ankles, and my bare skin became aware of the cold leather of the chair. Jen then smiled up at me as she observed my thick hard cock for the first time, its long, engorged head throbbing with excitement. She looked back up at me, eyeing me with approval, and then slowly her warm tongue began to lick the pre-cum oozing from it. She maintained eye contact the entire time as her licks enveloped my thick throbbing member. She then took my entire cock into her mouth, ensuring to coat it with a healthy layer of her saliva. After a few minutes of her licking, sucking, and teasing my cock, she stood up and lifted her dress once more. I could see she was leaking pussy juices all down her legs. Jen lifted the arms of my office chair, sliding them up out of the way and proceeded to hover her pussy just above my thick member.

"I don't have a condom," I gasped, barely able to stay with the moment, aching to have her sit on my lap.

"I am on birth control, and you forget that I know everything about you babe, you literally tell me everything," she giggled.

It was in that moment that I realized that in the last three months, I had innocently divulged just about every detail of every relationship I had been in through small talk and our daily office antics, and she had done the same. I also realized that I was closer to her than I had been in even some of my more intimate relationships. I immediately felt the friendship we had turning quickly into a love I had yet to experience before. I nodded at her with approval. She paused for a moment, making sure that this wasn't just a momentary lapse of sex-fueled judgment. I pulled her close for another passionate kiss. Our lips pressed together, hard at first, but again sinking into something so familiar but yet something so new. As our kiss softened, I felt her warm, tight pussy press against the head of my thick, throbbing cock. Jen eased herself downward onto me with the sweetness and grace of an artist as work. My head created pressure as it pushed through her tight lips, but once through, she easily slid all the way down my shaft until she bottomed out; her cervix rested against the top of my pre-cum covered head.

Jen moaned my name, and I moaned hers. She started rising and falling on my thick cock while wrapping her arms around me. I could feel the office chair pressing against the wall behind me with each thrust. My hands hungrily gripped her thighs and then worked their way to her plump ass. With each thrust up and down, I gripped her tighter and tighter, inadvertently spreading her ass. Jen moaned louder and louder and said she was going to cum again. As turned on as I was, I still wasn't close, so I moaned for her to cum anyhow. Jen's fiery blue eyes flashed at me as she commanded me to lift her off when she was ready. It only took a few more pumps of me pressing into her as she rode me on that creaking office chair before she was ready.

"Pull out! Pull out Daddy!" Jen screamed. I lifted her off of me and felt her entire body tense as she screamed my name at full volume. Just as my cock cleared her tight pussy, I felt the hot gush of fluids burst from her lips and spray all over my cock, waist, and legs. I was completely soaked. I did my best to push my feet forward and away from me as to not have my slacks and boxers covered in her squirt, but it didn't matter. Her love juices poured all over me, the chair and everything around us. She eased back down and I felt her swollen clit rub against my head. She moaned, kissing me at the same time, with that little interaction driving three or four more hard squirts from her tiny pussy. Despite the sound of the rain hitting the windows, I could hear the audible dripping and squishing of fluids leaking to the carpet below us. My ass squeaked against the leather chair, now warm with her gushing pussy fluids with each movement.

"FUCK! OH MY GOD! That felt so good," Jen moaned, her nails digging into my back. "I am so sorry, I didn't mean to squirt so much, but it felt so fucking good baby!" Jen looked flushed from both the amazing sex, and pure embarrassment. I reassured her that it was ok and that I wanted more, if she could handle it. At 27 years old, I didn't realize that she could be as insatiable as she was. She didn't bother to say another word and slid back down onto me, squirting ever so slightly on my cock upon reentry. She was extremely wet and slick now, and I could feel myself starting to build. I began to understand just how much I loved squirting and what a turn on it was to me. With each hard pump, I could feel her cervix and walls contract, letting out tiny squirts each time. She was completely in the zone now and I was with her. Like wet putty in her hands, with each thrust up, and each of her presses downward, I could feel myself growing thicker, harder, and closer to orgasm. I didn't want to end it just yet though and I realized that with her sitting on my lap, I didn't have much power to control that. However, that is when I noticed her big double D breasts bouncing in my face. I had been so fixated on her pussy and the nectar that squirt from it, that I had completely neglected her upper half. I again realized the inexperience of my age in that moment, but I recovered quickly as I came up with an idea.

"I want to suck on your boobs," I haphazardly muttered, trying to hold onto my last bit of manhood before blowing my load into her. Jen's smile immediately intrigued me. She paused to pull the shoulder straps of her dress down enough to expose her breasts to me. This was all the time I needed to regain composure down there. My cock rested as my eyes feasted on her huge pale breasts. In the dim office, I could see her smooth white breasts narrowed down to perfectly pink areolas accented with small soft nipples. She almost seemed ashamed of how small her nipples were, and began to comment on them. Whatever was said, I didn't hear a word of it. I was laser focused on them.

Leaning forward, I kissed them both softly. I could feel each soft nipple grow ever so slightly with just a simple kiss. I leaned toward her left breast, taking as much of it into my mouth as I could. Upon contact with my warm tongue, Jennifer moaned and I could feel her body tensing up. I used my left had to reach up to her right nipple, and give it a soft pinch and twist. Both nipples grew quickly in my hand and mouth. Jen moaned again. I began to play with her nipples with my hands and tongue, taking turns sucking on each one. As I did, her small, soft nipples became large and engorged with all of the attention. She moaned that she was going to cum again. I kept her still on my lap, wanting to see if she could cum from just this alone, and sure enough, after a couple moments, Jen pulled off of me and squirted two more times begging me to slow down and stop.

We sat there for a moment together just looking into each other's eyes. Jen's nipples had turned from a soft pink into a bright red. Her pussy throbbed, resting on my cock. The carpet beneath us was soaked. She slid herself back down onto my thick cock, but then remained still to catch her breath. She kissed me a few times and we giggled together at the mess we had made.

"I want you to cum. I want you to cum inside me Daddy," Jen whispered, still trying to catch her breath. I nodded. She started to slid up and down my shaft. Slowly at first, but picking up speed, her breasts slapping me in the face with each bounce. I felt the office chair smashing against the wall behind me as she gave it everything she had. She leaned in for a kiss. With one hand on her ass, and the other around the back of her head, I pulled her as close as I could to me. Our lips embraced passionately as her pussy lips engulfed my thick cock. We moaned between kisses. I could feel myself getting close. I asked her again if it was ok to cum inside her. She didn't even miss a beat and between passionate kisses, moaned for me to fill her pussy.

Our tongues intertwined and I felt her tight pussy lips gripping me harder and harder as she bore down on my huge cock. Just as I started to climax, I felt that new, yet familiar feeling of her cervix pressing down on the head of my cock. She was going to squirt again. Only this time, I wasn't pulling out until I had cum. The thought of her squirting hard on my dick was all I needed. I moaned her name just as I began to orgasm. I felt the first shot of cum leave the tip of my cock as she pressed herself all the way down on me. I fired rope after rope of cum deep inside of her pussy. Jen felt the warmth enter her and slowed her pace to hold me tight as I came deep inside of her. At the same time, her pelvis contracted harder than any of the times before. I could feel her leaking and the seal of her pussy lips began to loosen on my cock as she started squirting. I held her down tight on me to keep her from squirting out my fresh cream pie inside her pussy. Jen moaned and wiggled as if she wanted to pull off of me, but she held on tight to keep me inside. Jen squirted for what seemed like a minute, but it was probably only a few seconds.

Slowly she relaxed and we both collapsed on each other, trying to catch our breath. After a minute or two, Jen sat up, my cock still inside of her, but growing soft. She gave me a few soft kisses and then pulled her shoulder straps back up, covering her flushed chest and breasts. She glanced around the office looking for a tissue or something, and I joked that it wasn't going to make a difference. She giggled and kissed me again. Jen then eased herself off of me and I helped her to her feet. Her legs were wobbly and covered in her squirt. I jokingly asked her if she had kept any of my cum inside her, or if she had squirted it all out.

"See for yourself," she lifted her dress again, exposing that perfectly manicured pussy, dripping every so slightly with my cum. "The rest is still inside. You came a lot babe!"

"Rightfully so," I replied with a smirk, "I had no idea you could just keep going like that."

"You haven't seen anything yet," Jen replied with a wink. She reached for the black lace thong that had been inside her only a little bit ago and slid it on. "I have to make sure you don't leak out of me."

I went to pull up my slacks and quickly realized the full gravity of her squirting once I saw that they had multiple wet spots all over. Jen blushed and apologized. I reached for my gym bag and pulled out my spare outfit and a fresh pair of boxers. I used my gym towel to clean the puddle off of my leather chair. Once we were mostly cleaned up, Jen offered to wash and dry my clothes at her house later that night.

"So even after all that, you still want to go for round two tonight?" I asked with a smile, sipping my gin.

"You don't know the first thing about cougars, do you?" Jen responded in the most serious sexual tone she could muster. "Baby... we never stop hunting."