My Office Affair
by Master Jonathan
Copyright© 2021 by Master Jonathan
Erotica Sex Story: A high school boy working for his father has a crush on his secretary. One day he comes to work to find the secretary in the office alone and masturbating. He sees his chance to have the woman of his dreams...
Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa Consensual Heterosexual Fiction Workplace MaleDom Masturbation Oral Sex Voyeurism .
I was 17 when I went to work for my father. I’d had other jobs before – I had delivered newspapers for about six months and I had a small time lawn care “business” I ran. I cut grass and shoveled snow for people in my neighborhood, but it was nothing too serious. To be quite frank, I was having too much fun now that my school career was coming to a close.
I was in my senior year of high school, set to graduate that spring, and my father had the idea that I should probably start thinking of “what I wanted to be when I grew up” (his words!). My mother also thought that working with my dad, I would learn a trade and she wouldn’t have to worry about what I was up to. I’m afraid I had a bit of wild child still left in me and I tended to get into mischief when I was left to my own devices!
So to earn some money towards the car I wanted more than life itself and to placate my folks, I agreed to try working with my dad and see if I liked it. Dad ran a small construction company and it was a good job with pretty good pay. I wasn’t the type that would be happy in an office-type job – I had already proved that in school. I hated being inside on nice days and sitting still at a desk was sheer agony for me! So a construction job was a good fit.
I had been to Dad’s construction office many times and I knew most everyone there. I knew the guys in the work crews and got along with them all. And not just because I was the bosses son, either – they actually looked at me as an equal even as young as I was. I was friendly with the office staff as well. There were three people in the office usually – Dad, who was the boss and did most of the salesmanship and getting new business, the office manager, who took care of scheduling, timekeeping, and payroll, and Dad’s receptionist.
Of all the people that worked with Dad, it was his receptionist that I was most interested in. Susan Nichols was a very sexy 32 year old woman with long dark hair, soft brown eyes, and full lips that were always in a smile for me. I used to love coming to Dad’s work and when I did, I would always sit and talk with her while she did her work. I guess you could call it a schoolboy crush or whatever – I just know that she was the subject of many wonderful night’s dreams and fantasies! She was nice to me and we talked like adults. She didn’t treat me like I was just a kid, which I appreciated.
One day after class had ended for me, I was headed over to Dad’s office. I hadn’t started working for him just yet – that would have to wait another month and a half until I graduated – but it was a nice spring day and I wanted to walk the three or four blocks to his office enjoying the warm sunshine.
Dad’s office was a small building next to a large industrial type garage set back off the street with some of the construction equipment scattered about the yard. I walked through the yard, past the trucks, scaffolding, and other equipment to the office building itself. The office was actually just a small, old house that had been converted. I walked in the front door and down the short entry hallway to where Susan’s receptionist desk was.
Susan was alone in the office when I came in. Apparently the office manager was sick that day, and Dad was out meeting with some potential new clients and wouldn’t be back in before coming home. Susan was just there to man the phones and in case there were any walk-in customers.
Knowing she was the only one in the office, she had decided to make herself cum before she went home and had to worry about cooking and doing her typical housework. Susan lived alone and had broken up with her boyfriend about 6 months ago.
In some of our talks, I learned that her relationship with her boyfriend had been on the skids for some time and they basically stayed together because rent was too expensive for either of them alone. There was no sex between them, in fact she hadn’t had sex in a long time, and hadn’t felt like getting back into the dating scene yet.
Susan quickly reached into the deep V cut neckline of her blouse and slid her hand up to play with her large tits. She began to squeeze her sensitive nipples, and they became firm and stiff almost immediately. She made small circles with her fingertips around each dark aureola and flicked her hard buds, feeling the little electric spark as she did.
Susan had been horny all day and the naughty thoughts she had while sitting alone at her desk like this had already made her pussy moist, but as soon as she started massaging her plump breasts, she really started getting wet and horny.
She took a quick look around, and outside. Knowing she was all alone and that no one would be coming back to the office that day, Susan stood up, and went to lock the front door, turning the open sign around and closing the window blinds.
Satisfied she wouldn’t be disturbed now, she removed her gray suit jacket and hung it on the back of her chair. She then took off her low cut blouse and shimmied out of her tight black skirt and sat down again, putting her feet up on her desk, and spreading them wide apart.
Careful not to create a run, Susan gently pulled up each black stocking, to relieve the tension on her garter belt they were attached to. She then looked down on the rest of her lingerie set, feeling very sexy while admiring it. She hadn’t worn a bra that day, in fact she rarely wore one, and her pendulous tits enjoyed the freedom and the cool spring air.
Susan slipped her hand beneath her red, sheer lace panties and began to rub her aching clit. Her pussy was already very damp, and she slid her fingers down between her swollen lips to push into her wet pussy. She pulled her fingers out, sticky with her wetness, and rubbed them over her throbbing clit.
She closed her eyes and was deep in a fantasy world with some well hung guy. She imagined him rubbing the head of his massive cock between her fat puffy pussy lips and smacking her clit with it, teasing her as she begged him to fuck her senseless.
Susan had forgotten one detail in her preparations, however. While she had locked the front door and knew that no one would be coming back to the office (the garage that the equipment was worked on in had an alert bell so she knew if someone needed to have the door opened), she had forgotten the side door into the office.
When I came there from school and saw the front door was locked, I went to the side door just to make sure it was locked and it hadn’t been. I walked in and caught Susan in the middle of her masturbation fantasy, moaning and fingering her dripping pussy with one hand while pinching her thick hard nipple with the other.
Her head was laid back on the chair back and she was licking her lips, obviously enjoying her lover’s cock. I stood there silently watching her for several moments. Susan was so fucking gorgeous like that! And I had a perfect view of her amazing five foot four inch, 32DD-25-35 body spread out and being played with.
She may have been 32 years old on the calendar, but she had the body of a smoking 25 year old! It was so hard to keep silent while watching her, but I didn’t want to break the spell just yet. Susan was moaning and fingering herself excitedly and I knew she was getting close to her orgasm when I spoke.
“Can I give you a hand with that?” I said. Susan’s eyes flew open and she screamed. Completely mortified, she jumped up from her desk, knocking her chair to the floor as she snatched her jacket off the back to cover herself.
“Oh my God! I’m so embarrassed,” she said. “Please don’t say anything to your father. It would cost me my job if he found out about this!”
Advancing slowly toward her, I tried to calm her worries. “Please don’t be embarrassed Susan, you looked so hot playing with yourself. And don’t worry, I won’t say anything about this either.”
I came around Susan’s desk and I picked up her chair, helping her to sit down before her wobbly legs gave out entirely. I began to pick up the rest of her clothes and the things she had knocked on the floor in her panic. Recovered from her start, she stood up and took my hands.
“Thank you, Tommy. Thank you for not telling your Dad ... and for, you know,” she said. She still had her jacket covering her and pinned by her arms. I reached up and stroked her cheek softly then put my hand behind her neck and pulled her gently to me.
I kissed her deep and passionately, like I had kissed her a thousand times in my dreams. But my dreams couldn’t begin to compare to the soft sweetness of those lips.
She was a little shocked at my sudden boldness, but she was too horny to refuse. I took her in my arms and as I kissed her I pulled her tightly to me. She must have needed to be kissed too, because she put her arms around my neck and melted into me with a soft moan into my mouth. She parted her lips and I slipped my tongue onto her mouth and she began sucking on it like it was a small cock.
Now I had always enjoyed working out and I was in pretty damn good shape, if I say so myself. Which may have been why the guys there at work treated me as one of them – because I could do the work and keep up with them.
As I held her tightly, she could feel another muscle as well, one that she had been responsible for building this time! I knew the way she moved against me she was impressed with what she found there too, because she was trying to position herself to press her dripping pussy up against it.
I gently nudged the inside of her ankle, indicating I wanted her to spread her legs a bit and she did. I pressed my cock against her rubbing it slightly back and forth and I heard her gasp. I pushed her back a step so she could rest her tight firm ass on the edge of her desk. She wrapped one nylon-encased leg around me, pulling me closer.
I slowly slipped my hand down to Susan’s dark, well-trimmed pubic hair, and slid my middle finger into her hot, sopping hole. While we continued to kiss, I fingered her pussy and clit just as I had seen her doing it moments ago. She moaned and whimpered softly as I fingered her, heating her up again and bringing her passions to a full rolling boil.
Just before she was set to plunge over the precipice of her orgasm, I stopped what I was doing and took a step backwards. Susan sat there quivering in need, and looked to me now to satisfy that need. I reached up and slowly pulled her coat from her. She held it tightly with her arms at first but after looking into my eyes and seeing approval, she released it and I took it from her.
Setting her jacket down on the desk, I took her hand and we walked into another room. When this was a house, the room would have been a den or family room. However, now it served as a conference room with a large table and six office chairs surrounding it.
I pulled her into the room and shut the door behind us. I pulled her over to the conference table and hoisted her up onto it. She gasped a bit when she laid back on the cold wooden tabletop, but it quickly warmed.
She was still wearing her panties, thigh-top stockings, garter belt, and strappy, red high heels. I put my hands under her knees and brought her feet up onto the table, spreading her knees wide. She looked at me between her legs and smiled coyly.
Pulling up a chair I sat down to my feast. I began by kissing Susan’s inner thighs from the knee down slowly until I got almost to her sweet box. She trembled and began panting as I got closer and closer.
Just as I was about to kiss her where she wanted it most, I moved over and kissed my way up her other thigh until I reached her knee. I could sense the frustration she felt as I bypassed her dampening slit and I smiled at her disappointment. I started rubbing her sodden panties as I continued kissing the tender flesh of her inner thigh.
“Ohhh...” she moaned as her passion fire grew. I used my thumb to rub her swollen clit further aggravating her aroused condition. Susan’s hips began slowly rotating, grinding against my thumb’s work as she reached up and started playing with her bountiful tits, pinching and tugging at her swollen rock-hard nipples.
“Tommy, pleeease...” she whined softly, humping the air a bit to show what she wanted. I took hold of the waistband of her panties and as she held her hips up, I slid the drenched garment from her dripping slit.
As soon as the silky underthings cleared her delicate ankles, she threw her legs wide open, inviting me to enjoy the treasures before me. Well this was one banquet I wasn’t about to miss! I scooted my chair up to the table and put my face closer to her sweet sex. Her aroma was like a drug, intoxicating and heady as I drank in her woman scent. I could see her juices seeping from the folds of her flower and glistening in the room’s light.
“Ohhh, God, Tommy ... yesss!” Susan groaned lustfully as I began with several long laps with the flat of my tongue from the bottom of her slit up over her throbbing clit. With each lick she lifted her hips, wanting to maintain contact with my tongue for as long as she could.
Susan was on fire now and so I wanted to test the waters a bit and see what she liked. Prior girlfriend experiences had shown me that some girls liked to be talked dirty to – called a slut and a whore and using words like cunt and pussy and asshole. So with her in this current state of mind I wanted to see if older women like Susan were the same.
“Spread those pussy lips slut, and show me that dirty little pussy!” I said in my deepest manly growl. Susan raised her head to look at me with a big smile on her face. She pulled her pussy lips apart and showed me her tight wet hole leaking pussy juices as she held it open.
“Ohmygod! Ohmygod!” she cried out as I dove deep into the pink sweetness, shoving my tongue as deep into her as I could reach and licking at her honey-hole like I was starving. Susan opened her legs as wide as she could get them giving me as much access to her as possible, wanting me deeper still.
My licking must have been torture for her, because she tried scooting back away from it instinctively. But I wrapped an arm around her thighs and pulled her back to me, holding her in place while I shoved two fingers deep into her pussy even as I licked her.
Between the licking and lapping at her and my fingering her, Susan was going insane. She moaned and writhed on the desk, tossing her head to and fro and sending her dark hair flying in all directions.
She gave up holding her pussy open and instead clawed and mauled her tits viciously as she neared her orgasm, tearing at the soft mounds and abusing her aching nipples in an attempt to push herself that last little bit higher.
“TOMMMEEE! I’M CUMMING BABY! I’M CUMMING! OHHHMMMYYYGODDD!” she shrieked so loud I thought we might soon have company. Susan flooded her pussy and my mouth with her sweet juices as she bucked and twisted and writhed her rapture on that conference table. I have to hand it to whoever made it – I thought sure with her convulsions, we’d break it for sure!
But it held and she coated it with her juices until she was slipping and sliding around in her own cum. I sat back watching in prideful satisfaction at what I had produced in this older, experienced woman.
Finally she stopped her spasming and convulsions and lay there spent and panting heavily. As an act of ownership and to show her what I slut I had made her into, I put my fingers into her still quivering pussy and got them soaked with her juice then smeared some of it around on her face and let her suck the rest off my fingers. She loved it, moaning and sucking my fingers clean. She really was a slut!
I let her rest a little until she could sit up on her own. “Welcome back!” I told her, smiling.
“Mmmm ... Tommy, baby that was wonderful!” she said.
“Glad you enjoyed it. You were amazing!” I told her.
“Well you were pretty good yourself, sweetheart. But now let’s see what I can do to return the favor!” Susan said, sliding off the table and onto her knees on the floor. Looking up with her soft brown eyes twinkling and a naughty little smile, she started unbuckling and unzipping my pants. She tugged them down to my ankles and got a better look at the bulge that my cock was making in my boxers.
“My, my ... what do we have here?” she said playfully. “Does someone want to come out and play?” Susan gripped my cock and squeezed it, feeling it twitch in response. She gave it a couple strokes just to see it throb and then kissed it through my boxers.
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