Debbie on Her KneesbyBoxlicker101©
Years ago, when I was eighteen years old and had just graduated from high school, I was still unsure of what I wanted to do with my life. I knew I would have to work for a living, of course but I didn't know what I would be doing. My father had worked in the same factory all his adult life, and my older brother had been working there for two years, but I had no wish to emulate them. There was no future whatsoever in working on an assembly line, and I wanted something better, although I didn't know what.
I grabbed the first job I could get, which was as an office boy in a nearby city. It didn't pay much, but I still lived at home and I would be able to get some work experience, and it might lead to something better. I had always wanted to be a free-lance writer, and I had always done well in English Composition and similar classes. I liked the idea of the independence, but I wasn't sure I could actually make a living at it, and working at any kind of job might give me some perspective.
One of the first persons I encountered in the office was Debbie Wade. I remembered her quite well from high school, but she didn't remember me, which was not surprising. She had been a senior and a cheerleader when I was a freshman. Debbie was the stereotypical all-American glamour girl, blonde and beautiful and popular, and dating the quarterback on the football team. From what I heard, she got knocked up about a month after graduation and, when her boyfriend found out about it he skipped town. Nobody I knew of ever heard from him again. She had the baby but, at that time and that place, having a child out of wedlock was scandalous, and Debbie left town also.
In high school, I had often seen her in the hall, in her tight skirts and sweaters, but I never dared speak to her, and she never deigned speak to me. To Debbie, I and most others in her world were on about the same level as the flies that could sometimes be heard buzzing against the classroom windows. To me, dating her or somebody like her was a goal I could barely hope to even aspire to, and something to think about when I lay in bed and masturbated at night. Even then, three years after the last time I might have seen her, Debbie was still a blonde beauty and somebody to fantasize about. She was also just as snooty as she had been in high school, in particular toward those, such as I, whom she considered to be beneath her. She was a secretary; at that time that meant that she would take dictation from Mr. Schwartz, her boss and mine, and type letters and keep his appointment calendar and do similar important jobs around the office. Debbie considered herself to be a skilled professional, and superior to those in more menial positions, such as the one I held.
As the office boy, I was at the beck and call of everybody in the office, and I made deliveries and ran other errands for anybody who requested or demanded my services. Late one morning, I was called on to take a monthly sales report to Mr. Schwartz. Usually, this would entail handing the report to Debbie, so she could do the actual delivery to Mr. Schwartz in his private office, but she wasn't at her desk when I got there. This was not a problem. I opened the door to the inner office, intending to hand it to the boss, or set it on his desk, and leave. However, when I entered the office, I beheld an amazing sight.
There was Debbie, on her knees in front of Mr. Schwartz. I couldn't see her face, but I easily recognized the long ringlets that hung across her shoulders, and the creamy white ass and blonde pussy were what I had thought of, day and night, for almost four years. Those very private parts of her body were clearly visible, because Debbie was completely naked, and I saw her clothing folded neatly and stacked on a chair in front of the desk. Her boss was wearing a shirt and tie and a smile, but his pants were around his ankles. As she knelt there, her head was moving up and down over his lap, and I realized that Debbie must have been sucking his cock. My sexual experiences at that time were strictly limited to discussions with my buddies and looking at a few dirty pictures. I had heard that girls or women sometimes did things like that, but it had never happened to me, and I had never heard of it happening to anybody I knew either, until that day.
I'm not sure why, but I closed the door behind myself, and that noise startled the two persons in front of me. Mr. Schwartz opened his eyes and stared at me, but Debbie was a whole lot more flustered than that. She remained on her knees, but turned facing me, one arm held uselessly in front of her breasts and her other hand trying to cover her pussy. She didn't succeed in hiding her body and, even if she had, my imagination was already filling in the blanks.
"Go away! Get out of here!" she demanded of me.
Apparently, Mr. Schwartz didn't take kindly to his secretary bossing people around in his office. "I'll tell people what to do in this office. And, I told you to suck me off, so get your mouth back here on my cock until I cum into it."
"Please tell him to leave, Mr. Schwartz."
"I will not." He looked up at me then. "George?" He was unsure of my name, but I nodded my head in reply.
"What do you think of Debbie, George? Sexy, isn't she?"
I could hardly speak at the sight of her, because she really was sexy, especially in her nakedness. She was still trying to cover her breasts and pussy with her arm and hand, but I saw enough of her and could still see enough that my cock was trying to rip its way through my pants. "Yes, she is," I croaked.
Debbie still didn't like having me look at her naked body, even though I had expressed sincere admiration for it. "Please make him go away. I'll suck you off if you do."
"You'll suck me off anyhow, or I'll fire you. Sucking and fucking is the only thing you're any good for anyhow." Something else occurred to him then. "George, why don't you fuck her from behind while she sucks me off?"
"Oh, please, Mr. Schwartz. Please don't make me do that. I'll suck you off, but please don't make me let him do that."
"Shut up, Bitch. You'll fuck anybody I tell you to." He looked at me again. "How come you've still got your pants on?"
Debbie started crying then. I don't know if she would have been fired for refusing to do what she was told, and she didn't either. She did know that jobs were not easy to find, especially with the bad reference she would probably get from her current boss if she didn't do what he said.
"Quit crying and start sucking and fucking," Mr. Schwartz ordered her. She didn't stop crying, but she did turn toward him, still on her knees, and take his cock into her mouth again.
That order had been meant for me too. I felt a little bit guilty about fucking Debbie when she obviously didn't want me to, but that guilt was nowhere near strong enough for me to refuse the boss's order. For one thing, he might have fired me if I had done that and, for a more important reason, I had always wanted to fuck Debbie, and I wasn't going to let her tears stop me. Before doing anything else, I made sure to lock the door I had just entered. I definitely didn't want anybody else walking in and seeing what we were doing.
I took my wallet out of my pocket, not for money, but to take out the condom I kept there. Back then, all teenage boys and young men carried what we called rubbers, although not with the expectation of ever having a use for them. They were more a sign of manhood than anything else, but they were also functional, in the remote possibility the opportunity ever arose, as it had for me that day. I stood behind Debbie, pulled my pants and underwear down to my knees and peeled the foil wrapper off the condom so I could roll it onto my hard cock. I was ready for a brand new experience, with the sexiest girl or woman I had ever known.
It was so new, that I wasn't really sure what to do, except to get to my knees behind her and between her legs. To start, I reached out and put my hands on Debbie's ass, one on either cheek, and was surprised at how wonderful they felt. I don't know what I expected, but my hands had never felt anything so good, like a pair of warm, vibrant silk pillows, and I ran my hands under her curves and between her legs until I was touching her pussy lips with my fingers. She seemed to pull away from me, but I persisted and, seconds later, the tips of my fingers were touching her where they wanted to touch. During bull sessions, when we talked about sex, everybody always described a pussy as being wet, even juicy, but Debbie was actually dry, although very soft all over the area that I was fondling. I didn't know why, but I wasn't going to let that stop me. Softly, so she wouldn't hear me, I spit repeatedly on my hands and used the saliva to wet her pussy and my cock.
With everything ready, I reached back in and spread Debbie's pussy lips with the fingers of one hand, while I used the other hand to guide my cock, until it was pressed against the opening I was creating. With a firm push, the head wedged between my thumb and fingertips and between Debbie's soft lips and into the hole I had dreamed of so many times. For the first time in my life, my cock was actually inside a pussy and, not just any pussy, but that of the woman I had fantasized over for almost four years.
I pushed forward again, and more of my cock squeezed into her, but she was still dry. Debbie decided to help out then. While continuing to bob her head up and down, taking Mr. Schwartz's cock in and out of her mouth, she reached under her body to pull her pussy open for me. At the time, I considered it to be an indication that she was having fun, and wanted to get the best fucking she could, and I took advantage, and thrust my cock deeper into her. I have since come to realize that it may have been painful for her, because of the dryness, and that she wanted to get it over with as quickly as possible. Whatever her reason, I certainly benefited from it. While she held her pussy open for me, I quickly drove my cock in the rest of the way, drew back, and rammed it in again and again.
Although I was horny, by the usual definition, my horniness was not really acute that morning. The edge had been taken off it when I jacked off in the shower before coming to work, ironically, while thinking about Debbie in the low cut blouse she had worn the previous day. It had been fun, but it was nothing compared to the real thing. Even dry, her pussy felt infinitely better surrounding my cock than my soapy hand ever could have. She was even starting to feel less dry, as if she was producing some moisture, the way I thought a pussy should.
"Why don't you play with her tits too, George," Mr. Schwartz suggested.
That seemed like a good idea. Although the soft, warm flesh of her hips felt delightful against the palms of my hands, I leaned forward, reached around her body and cupped one large breast in either hand. It was sensational! I had always been a bookish youth, too shy to approach girls, and had never had any involvement with them. I had always admired breasts, such as those of Debbie, and I sometimes heard people talk about "feeling up" a girl friend, but I had never done anything like that. When I fondled the succulent breasts of the sexy blonde kneeling in front of me, I became aware that my life had been sadly lacking up until then.
They were two truly delightful handfuls, big and soft, but alive, with flawlessly smooth skin, except for a somewhat pebbly area around the nipples. Those adorable nubbins were big, and felt almost rubbery, but they seemed to harden slightly when I fondled them between my fingers. While I caressed the luscious breasts, I continued fucking their owner. I knew enough to thrust my cock in and out of her slowly, because it would last longer, and be better than if I hurried myself. Although it had felt incredibly good when I started fucking Debbie, it had gotten even better. For one thing, her pussy was definitely not as dry as it had been. For another, she seemed to be pushing herself back to meet my strokes.
I wasn't the only one having fun. Mr. Schwartz's eyes were closed, and he was leaning back in his chair, obviously enjoying the blow job from Debbie as much as I was enjoying fucking her. He was grunting, and his hips were jerking and, suddenly, he grabbed onto her head, holding it in his hands and ramming his cock in and out of her mouth. I had always lusted toward Debbie, but I suddenly felt different, affectionate and even protective toward her, and I wished he wouldn't treat somebody as pretty and as nice as her in such a rough way. I might have said something but, before I could, he grunted loudly, and apparently ejaculated into her mouth. Even though he had cum, he kept a firm grip on her head and kept his cock stuffed inside her mouth.
"Swallow it, Bitch. Swallow it all," he commanded her. I was still leaning forward and fondling her breasts, and I saw Debbie's mouth working, and it looked as if she didn't object to doing as she was told in that regard either, so I said nothing. I also noticed her nipples were considerably more rigid than they had been, and I couldn't help wondering why they had changed like that.
After he released her head, Debbie raised it above his lap. She had been supporting the weight of her upper body with her forearms on Mr. Schwartz's thighs, but she moved them so her hands were on the front of his chair seat. With her mouth no longer busy, I could hear Debbie making soft murmuring noises under her breath, and I could see that she was pushing against the chair, thrusting her pussy back to meet my cock as I thrust it into her.
The man who remained sitting in the chair noticed these things too. "You really like to fuck this guy, don't you, Debbie?" She turned her face back to me to smile, the first time she had ever smiled at me. When she turned her head back, she nodded her head in reply to the question.
I was really glad she liked what I was doing to her, because I had been starting to have guilty feelings about having forced myself on somebody as sweet as Debbie. I continued pumping my cock in and out of her, and she kept meeting me halfway. Her pussy had become almost slick, and her nipples seemed to be covered with a multitude of hard ridges, which felt almost sharp against my fingers. Her hips were squirming and her back writhed in front of me. Even with my total lack of experience, I could tell she was starting to enjoy the fucking, maybe even as much as I was.
Debbie turned her face to me and smiled again. "Make me cum, George. Play with my clit."
I didn't know what she meant by that, and she must have realized my inexperience. Debbie took one hand from the chair seat and moved my hand from her breast to her pussy, which was even wetter than I had realized. She guided my fingers to a small, soft ball, which was sandwiched between two folds of the skin of her pussy, squeezed my fingers closed over it and started moving them. I caught on quickly to what she wanted, and began stroking her the same way, at the same speed as I was plunging my cock in and out of her pussy.
"Yes! Yes! Like that!" she told me. "And start fucking me faster."
I was much mote than happy to do that. My climax had been building up, and I knew it was on the verge of exploding. The thumb and fingers moved faster on her clit, and I drove my cock in and out of her pussy at the increased speed. Although her breast still felt wonderful, I moved the other hand back onto her succulent hip so I could pull against it and fuck her harder. Debbie continued meeting my strokes and her body rocked from side to side in front of me. I could hear her gasping and moaning, but I knew she wasn't suffering.
"Oh! Oh! Yes! Yes!" she cried and I knew, although I had never seen it happen before, that Debbie was starting to cum.
I continued driving my cock in and out of her pussy and fingering her clit, while her movements in front of me grew more frenetic. I was afraid she might fall over, but her hands on the chair seat and my arms around her hips kept her upright, until she gave a joyful cry, and I realized she must have climaxed. She relaxed in front of me, but I didn't, at least not yet. For a few more seconds, I rammed my cock into her, until my own climax exploded.
I had jacked off quite a few times during my life, and cumming from that was fun, but I found it to be no more than a pale imitation of a climax from sex with a real woman, especially one as sweet and sexy as Debbie. I ejaculated once into my rubber, but didn't stop fucking until I had squirted my cum twice more. I leaned forward on Debbie, feeling extremely affectionate toward her, and careful to avoid putting too much of my weight on her.
Mr. Schwartz was usually a curmudgeon, but he must have mellowed somewhat from being sucked off by somebody with a face as pretty as Debbie's, and by watching us younger people having fun fucking. He let us stay where we were until we were ready to leave, and even smiled while he watched us get dressed again. All I needed to do was pull my underwear and pants back on. The condom was still covering my cock, but I would go to the men's room and flush it away as soon as I left. I helped Debbie get dressed, hooking her bra and zipping up her dress and letting her lean on me while she put her stockings and shoes back on. Being a gentleman, I let her walk out the door ahead of me and, just before she returned to her desk, she smiled at me and squeezed my upper arm.
I continued to work there for a few more months, and saw Debbie almost every day. She was much friendlier than she had been before that day in front of the boss's chair, and I very much enjoyed her company. When I left, her presence was probably the thing I missed the most. After my experience of working for Mr. Schwartz, I decided a career of clerical style work was not for me, and I enrolled in a creative writing course in college, beginning the following fall. Although I have enjoyed a considerable amount of success in my life, both as a free-lance writer and romantically, I will always have a warm, fuzzy place in my heart for Debbie, and I will always be glad she didn't resent the way I took advantage of the situation with her.
Thank you for reading this story. I hope you had as much fun as I did and as Debbie ended up having. I like writing stories on Literotica, but I like it a lot more when I know that people are reading and enjoying them, and I appreciate it when readers take the time to express their opinions by voting. Like most authors on Literotica, I practically live for feedback from readers, either public comments or email to me. Such feedback, whether praise or criticism, helps me to write more and better stories, and I respond to it whenever I can.