Caught by the Secretary

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Double Penetration

It was the mid 1980s. I was a young student at university, majoring in chemistry. My family was of somewhat limited means but I was very smart, at least academically. I had almost a full scholarship, which enabled me to live in campus and take classes full time without any cost to me or my family, something I took great pride in.

When I was at university, I had a job at the Department of Mathematics, grading papers. Every two weeks or so, I went to an office at the Department and turned in a timesheet to a secretary. Her name was Angie; she was much older than I was, probably about 60, and I liked her. She was kind of maternal. There was another secretary there who I saw occasionally. She was the secretary for the department head, and Angie’s boss. She was probably in her late 50s, and I was a little bit afraid of her. I had to speak to her once or twice; she was rather overweight but had very large breasts, and also a deep, smoky voice. She wasn’t particularly friendly, very no-nonsense, but she was efficient at her job. After I finished school and no longer worked there, I began to have this fantasy about her:

It is a Friday in April, late morning. I have just finished my Sociology class, and now is a good time to go up to the Math Department and turn in my time sheet. There is a warm breeze blowing, which brings the feeling that Spring is fully arrived. More people than usual are ditching class and hanging out in the Quad, throwing frisbees or sitting on blankets in small groups talking. Some are feeling “spring fever,” that strange rush of endorphins that hits some in early spring and makes you want to do nothing, except maybe drink or have sex.

I take the elevator to the third floor and go to Angie’s office, but she isn’t there. I don’t want to just leave the time sheet on her desk, as she might be on vacation or something, and in that case I might not get paid for a while. So I go to another office just down the hall, where Kate, another secretary, works. I like Kate also, although I rarely interact with her. Kate’s door is open, so I walk in, and am quite surprised when instead of Kate, I see the head secretary, Phyllis. My heart sinks into my stomach; I hate to admit this to myself, but I am rather afraid of her, and I don’t really want to deal with her. But I have no choice, unless I want to waste time with another trip. So I awkwardly introduce myself and start to explain that I need my timesheet authorized and given to my professor to sign. She gives me a strange look as she accepts the paper from me. I say thanks and turn to leave.

“Hold on a second, Gilbert,” she says in her husky Baltimore accent.

I freeze in place. Oh no, what is she going to say?

“I need you to close the door and ask you something.” My heart starts racing and I feel afraid again. What is she up to? But I comply.

“Let me take another look at you,” says Phyllis. I stand there, not knowing how she wants me to stand. I’m afraid she is going to tell me someone has complained about my work, that I might even lose my job.

“Stand in profile, please,” Phyllis commands, and I reflexively obey even though I just want to get out of there and don’t think she has the right to mess with me.

“That’s what I thought. Casibom You’re that pervert kid who has been staring at us when we are in the courtyard smoking.” My cheeks instantly flush with embarrassment. It was true, I had made a habit of watching Phyllis and a secretary from the Economics department (fourth floor) have cigarettes in the courtyard after they had lunch. I always made sure to hide behind a tree and keep a distance and thought they would never notice. And now here I stand, squirming with fear, my arms fidgeting with attempted movement while my legs stay rooted to the floor. And I know my body language is giving me away. She knows it’s true now for sure. I don’t know where to aim my eyes, so I try to stare at the shelf behind Phyllis and hope I can think of something to say in my defense.

“Hello?” Phyllis asks sharply. I realize that in my fear, my gaze has shifted and I am staring straight at her very ample breasts, which are straining against her white blouse. If possible, I become even redder.

“So you like these, do you?” She glances down at her chest. Again I don’t know whether it is better to deny it, or just remain silent. I can’t believe this is happening.

“I don’t know what you’re talking about,” I finally manage to say, not very convincingly even to my own ears.

“Then what’s that about?” she asks, with an amused, slightly twisted smile on her face, pointing to my groin. I realize I have a big hard on and the bulge is visible. All I can do now is throw my arms out as if to say, “What do you expect? I’m a 20 year-old guy.”

“You think you can just mentally undress me and Marlene and then go back to your room and whack off or whatever you call it now,” Phyllis declares, her voice starting to rise. “Well, today that is going to change.”

“What do you mean?” I manage to ask.

“Today I’m going to teach you a lesson, one I hope you will take to heart.” I start to feel panic. Is she going to call the school administration? Or my parents??

“No more sneaking around,” Phyllis goes on. “Take those pants off.”

I give her a look that says, are you nuts?

“I have enough dirt on you now that you had better do what I say,” she growls. Red faced and bewildered, I comply, and my pants slide down my legs and around my ankles. The bulge is even more obvious in my tight underwear. “Those too,” she adds. Numbly, wordlessly, I slip my underwear off too. My penis points up and to the left, ready for action, even though I don’t feel I am.

“Not bad,” Phyllis purrs, delighted to have assumed full control of the situation. “It looks like you haven’t abused him today yet. That’s fortunate.” I start to wonder: is she turned on or attracted? And what if someone walks in?

“No one will open that door except me,” Phyllis tells me, seeming to read my mind. Then again I might have glanced backward towards the door, I was so self-conscious.

“So, you like big boobs, do ya?”

I mutely nod.

“How about you show these gals some love?” She unbuttons her blouse and allows her two creamy, white mountains to emerge and flop down over her midsection. I have never seen tits this big. I would guess they are DDD. Although they sag with age and have probably Casibom Giriş nursed babies, they are still sort of firm and surprisingly round. Her areolae are wide and the nipples stick straight up.

I start to walk in her direction, shaking. “Stop,” she commands. “I want to see you jerk off for me. Do what you normally do, but this time I get to see it.” I can’t believe what she just said. It is so embarrassing, no one is supposed to see me do this! I look down, angry at my penis for betraying me.

“Maybe this will help?” I look up at her and a long white cigarette is between her lips. She clicks a lighter and almost instantly the end of her Saratoga 120 glows orange as she takes a big, evidently satisfying first drag. She tilts her head back and lets the smoke enter her lungs, then blows a big cone of gray-blue exhaust towards the ceiling.

It does help. Two of my favorite things on a woman — big breasts and a cigarette — are right here in front of me. Make that three: someone old enough to be my mother. I reach down with my right hand and grasp the shaft. I start to slowly move my hand up and down as Phyllis holds her breasts up higher with her left forearm and her cigarette in her right hand. “Is that how you do it in your dorm room, hoping your roommate will stay away until you finish?” She looks amused, and maybe also a little aroused.

“I don’t usually stand,” I manage to say. “I usually have more privacy, sometimes I’m under the bed covers.”

Phyllis chuckles and takes another drag. “You want to get a little closer?” With each syllable a little puff of smoke comes out of her mouth; she doesn’t bother exhaling that one. I take a few steps in her direction, around the corner of her desk. Now I’m standing only about two feet in front of her. As I stroke, I look down and am just awed by the sheer size of her breasts, heaving gently up and down as Phyllis continues to drag on her cigarette. I find her baritone voice rather exciting and scary at the same time.

“That’s close enough,” she says softly. She inhales again and this time blows the smoke into her own cleavage. I feel myself ready to climax, but I don’t dare do it without her permission. It is clear that Phyllis is absolutely in charge of everything and I realize she will tell me when I can finish. I slow down my pace and grip my cock a little more loosely so it will calm down. Then I start to hear a little bit of moaning. I hadn’t noticed, but Phyllis has dropped her hand down into her own crotch and is playing with herself. The cigarette stays between her lips, dangling slightly, occasionally drawn upwards as she inhales and lets the smoke come out her nostrils. A tiny bit of ash falls off the end of the cigarette and falls onto her chest just below her collarbones. She doesn’t seem to notice.

She takes another big drag on her cigarette and blows the smoke in the direction of my cock. Now I really don’t know how much longer I can keep myself from blowing my load. She seems to sense this.

“I bet you’d like to spray your seed all over these girls, wouldn’t you?” she asks with a wicked smile. Actually I hadn’t even thought of that, but it seems like a great idea. I just nod.

“Well, step a little closer and let it fly.” I do as instructed. At the point of the most intense orgasm I have ever had, I aim straight into her cleavage. Three, four, five jets of cum spurt out. The first two land squarely on her chest in the space between the tits. The next two fall onto her right breast, as I let my penis go back to its natural position slightly to the left. The last is thicker, and stays attached to the head, hanging there for a moment before dripping onto the floor. My breathing is very deep. I notice my back is drenched in sweat. “Mmmmm,” she growls, shuddering in her chair as she evidently has an orgasm of her own while she exhales the last of her cigarette. I stand there for a moment, spent.

“So was that a little better than squirting into a kleenex under your blankie?” Phyllis stubbed out her cigarette and I slowly nod, my mouth wide open in astonishment.

“That was a nice performance, Gilbert. I give that four stars,” she chuckles. As I start to nod with a little pride, she holds up her hand.

“Well, didn’t your mommy teach you to clean up your messes?” she looks at me expectantly.

“You want me to wipe you off?” I ask sort of stupidly. Clearly, she is always at least one step ahead of me.

“Yes. With your tongue.” I look at her in horror: since when do guys ever eat cum? She looks back at me with raised eyebrows that say, “Well??” I suck in my breath and bend over Phyllis’s chest and start to lick and suck the sticky goo off her magnificent torso. I don’t care for the taste at all: sour and salty at the same time, and a smell like ammonia. I lose my balance slightly and almost fall into Phyllis’s lap. I feel hands on my back.

“There, there. Mommy is very pleased with you today.” She pulls me into her cleavage and lets my face rest there, swallowed up on either side by her massive chest. I feel a mix of humiliation, fading arousal, and…relief. Maybe even love.

“That’s a very good boy,” she continued. “Mommy is so pleased with you that she wants you to come back here at the very same time next Friday.” I feel her deep voice vibrating right through my skull as she strokes the back of my head. “Mmm-hmm,” I murmur. We spend another few minutes like this, mostly in silence. I feel an ecstasy I have not known before, along with a repeated thought of “Did this really just happen?”

Finally, Phyllis tells me she needs to get up and get back to work, there are memos to write, checks to mail out, etc. She wets a paper towel and wipes herself off a little more thoroughly and then quickly puts her bra and then her blouse back on. I just stand there, dazed, with a smile of wonderment on my face.

Phyllis’s eyes suddenly focus and she gasps slightly. “You messed up Kate’s floor,” she cries. “Lick that up right now!” I look down and see a spot of semen, easily seen against the blue tile floor. “Go on!” She suddenly sounds nasty again. I drop to the ground and lick it up. Again I gag slightly at the taste, this time accented with a little floor wax. “That’s right,” she says. “You don’t leave anything undone.” I stand up when I’m done, feeling humiliated again.

“Now put those pants on and go to the restroom to wipe yourself off,” Phyllis admonishes. “Don’t be disgusting.” She is already being mean to me again after showing a little tenderness. I obey her commands and silently walk out of the office and down the hall.

And I notice a bulge already re-forming.

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