You have been working at this job for a six months now, yet no matter how much you tried and how good you did, you would always slip up from time to time.
One day, when were leaving work, you fell into the trap again. “Alright, I’m signing off, see you tomorrow!” You said, leaving with your things.
“Did you finish the copy for the charity flyer I asked you to do?” That was your boss. Always the last to leave and the first to notice all your mistakes. You had worked closely together many, many nights. You thought you knew her well and had some form of relationship. You also knew she had a quick temper which is what made a tear of sweat drip down the side of your face.
“Oh, I am so sorry. I forgot.” You were being honest. You had so much to do, it had slipped through the cracks.
“You forgot?” She stood up from her workspace. “Again?!” Cassandra raised her voice. She had vibrant ebony skin, black wavy hair, a mature, tall and curvey body with very large, plump breasts. Her shirt, an extra button down showed her beautiful cleavage and clung to her body. Her form-fitting pencil skirt accompanied her round, beautiful ass. She trulywas a sight for sore eyes but you tried your best not to stare at her from day to day. She deserved the respect.
“How could you fucking forget?!” Her voice grew loud and filled the room. You were silent. “I asked you a question! How did it happen?!”
“I’m sorry. I was just so busy, I should have written it down.”
“People are counting on us for that. We can’t just miss the deadline. We’re going to have to work overtime until it’s done.” Her voice became honest and you could see that all she cared about was helping the people from that charity. “Don’t screw it up this time, okay?”
You worked on your task through the night, completing her various changes and keeping up despite her temper. It was past midnight when you had sent off the final flyer. You and Cassandra were exhausted emotionally and physically.
“Alright, we’re done.” You sat up and looked at her from where she sat beside you at your desk. She looked wiped. “Hey, look.” You said to her earnestly. “I’m sorry I brought you into this mess. This was my fault and I promise to work hard on improving my task management skills. It won’t happen again.”
“As the boss, I’m used to staying up like this. I have something of a resilience to all nighters. It’s just my shoulders that are killing me right now. They’re all cramped up.” You felt bad for her. Your mistake had cost her, her comfort. All because you forgot.
“Could you massage my shoulders, loosen them up a bit. They’re just throbbing.” Cassandra had never acted vonerable like this to you before. You felt responsible and couldn’t let her down again.
“Of course.” You came over behind her, then placed your hands on her warm, smooth skin and gave her shoulders a squeeze. You could feel her react as you worked her muscles. You felt satisfaction in helping her in a time like this. Most guys would just be lazy and only care about themselves. But you put her first.
You felt kind of sad too. You had liked Cassandra for some time and were working up the confidence to ask her out. But after today, after your mistake, it was all for nothing.
“I know you work hard every day.” Cassandra spoke up. “I just get so focused that when something goes wrong, I lose my temper. You don’t deserve that. I will work on it.” Her words penetrated you. It meant a lot that she cared to clarify.
“Could you do harder?” She asked and you complied, prompting the slightest grunt from her and she lifted her chin slightly. Her skin felt good against yours as you massaged it for a while longer. Then she said, “Could you… my feet are hurting…” She reached at her flats. “Never mind… that’s too much to ask-”
“No, I’d love to.” You kneeled before her as she removed her shoes, then the and offered you her bare foot. It was moist and cold. Something about it made you feel intimately closer to her. You gave it a squeeze and watched her face as relaxation washed over it. You massaged it some more. During one squeeze, her body jerked crookedly as you hit a hot spot.
“Hey, it’s okay. I got it.” You held
her foot, stopping her from pulling it away and let her relax again.
Staring down at you, Cassandra thought about how she really did like you from the start, respected your workmanship and personally. She was always very attracted to you but never had the guts to say it. She bit her lip but you were to busy to notice. You switched to the other foot and massaged it for some time. You realized it was the first time you had ever touched her. Cassandra pulled her foot away softly.
“Now.” She said and looked into your eyes. “Massage my boobs.” Your heart skipped a beat and your you almost felt dizzy. “What?” You couldn’t believe what she had said. Cassandra leaned down and grabbed both of your hands and placed them on her breasts. “I love you.” She said and you could feel warmth fill your chest. Your confidence restored. “I love you too. I always have.” You couldn’t believe what you were saying but you meant all of it.
You squeezed your boss’s large, pudding-like breasts, her head turning to the side as she let out a small groan. You felt all this built up tension you didn’t know you were carrying inside you release itself as you massaged her malable tits. Her boobs formed to you fingers as you pressed up against them.
Suddenly, Cassandra kissed you. You felt her soft lips smash up against yours and what she did next, seduced you to the core. You felt her tongue reach inside your mouth and brush up against your own. You responded back, exploring the inside of her mouth with your tongue. Cassandra pulled open her shirt and let her big boobs plop out. You couldn’t see them mid-kissing, but your hands could, massaging their smooth and slick texture in every way. When she finally broke away for air, you said, “Let’s get together… Perminately.” And she knew what that meant.
Pulling her shirt off and undoing her bra, Cassandra made quick time and unbuckled your pants while sitting in her chair. You thwm off, your hard cock swinging and bouncing out. Cassandra grabbed your pelvis and took you in as you took in the overwhelming sights. She pulled your dick between her huge breasts, then pressed her hands on either side of this “boob sandwich” and shifted back and forth, letting you essentially fuck her boobs.
You felt your shaft smack up against her sternum everything once in a while and were surprised with how tightly she pressed her boobs together on your cock, squeezing it hard. Her beautiful face looked into your eyes with love and affection. You stared back, locked in a gaze with her. Her face was so kind and beautiful you could have stared at it for hours. Precum began to lubricate her boobs and just as you felt an orgasm coming on, she pulled away. Was she teasing you?
Cass stood up and placed both hands on your cheeks, pulling you in for another kiss. This time more passionate, stronger. Cassandra was a few inches taller than you, so you almost had to tippy toe to keep up with her. Cass turned you around and with her body pressed up against yours, grabbed ahold of your cock from behind and began stroking it with a very firm grip. You made a noise of pleasure when she sped up the pace, breathing into your ear and pleasuring you dominantly. Once again before you could come, she let go.
She pushed you backwards, and into the edge of a table, knocking things over as she set you down on top. Cassandra quickly kneeled and put your penis in her mouth, massaging it with her tongue. She was too eager to eat you up and couldn’t hold back no more. You couldn’t believe what was happening anymore. You got so lost in love and pleasure, you couldnt keep track of it anymore. Each minute you reached new heights of ecstacy, and when she had her mouth sucking your balls and was stroking your cock, you lost it and moaned loudly, prompting a smile from her busy lips. She stopped just as you were about to let it all out on her.
“Not yet.” she said. “I want it in here.” Your boss placed her fingers, wet with precum and saliva onto her shaft. “Not yet.” You countered and sat her back down, going on both knees and lifting up her skirt. She was surprised to see you take the lead and let out a little squeek. “First, we give you a turn.” You said, then pressed your lips into her pussy. Cassandra let out an instant moan and dug her fingers into your hair, pressing you deeper into her vagina. She was enjoying herself just as you had. Eating her pussy out was the most beautiful thing you had ever done. You felt her body jerk away in eminence pleasure while she moaned and cried out, keeping your face pinned to hers.
“No.” She suddenly said and you stopped, confused. She rose and grabbed your hand, walking you up to her office chair. Cassandra climbed into her chair on her knees with her naked ass facing you. “Let’s cum together.” You held onto her hips and spoke up, “If we do this, we are together perminatley. No take backs.” Cassandra looked back into your eyes, hers full of emotion and wet with what could have been tears. “I love you deeply, madly. I want to be with you forever.” You smiled and touched her face. “Then forever it is.”
You took your penis and reached it into her pussy, carefully watching her reactions to not go in too strong. Cass smiled as she let you grab her wrists and bounce her ass against your balls, in a playful, cheerful manor. You both loved each other so much. You started to remember your first moments together and now where you were. In the body of the woman you loved. Cass’s body began to sweat up and your skin grew red and sticky as well. Soon you were making loud, uncontrollable noises and not worrying if anyone stayed up late to notice.
Before you knew it, you had changed positions; with her on the floor on her hands and knees and you fucking her ontop and behind, you legs squated and hands on her back. You sped up the pace while still being as gentle as could be. Your moans began to synconize which only meant one thing.
“I love you, I love you, I love you, I love you!” She repeated hysterically as you reached the moment. Suddenly the two of you orgasmed, shouting out loud enough for the neighbors to hear. You knew this was the woman you wanted to be with forever.
You felt your cock shoot out five bursts of smooth cum into her womb. You were both still, panting loudly, your hair wet and body hot. Cassandra dug her pussy back slowly into you, rotating her hips back and forth ever so slightly and digging you deeper into her. As the cum began to spill out, you lifted her whole body up and layed both each other down on her empty desk.
“I love you too.” You said. Laying to her left, you began a gentle side fuck and kissed her slowly and passionately, your mixed cum dripping out and making a shameless mess over her desk. Maybe today wasn’t so worthless after all. Sometimes through the bleakest of time comes the greatest connection and understanding. Later on in life, you and Cassandra got married, had constant incredible sex, gave birth to multiple children and lived a happy, fufilled life. ❤️
Source: reddit.com/r/Erotica/comments/guicwf/love_sweat_dears_office_romance