It was almost 6 pm on a Friday, and I was the only one left in the office. I had graduated from high school in June and had moved to a small apartment, which was located near the college that I would be attending in the fall, in a suburb of Boston. My dad’s best friend was able to get me a summer job through his contacts at a small firm nearby. My tasks would be in administrative and purchasing duties. It gave me the opportunity to earn money during the summer and a possible opportunity to work part-time during the school year if things worked out well. It was a job, so I was grateful for that, but I knew that I needed to prove that I was able to accept responsibility and do a good job. I was warned by my dad’s best friend that it would reflect badly on him if I fucked up, so I’d better do whatever was needed if I had any hope of continuing after the summer.
I had arrived at a point where I could stop and pick up where I left off on Monday, but the couple of empty bottles of Mountain Dew on my desk were the cause of my needing to take an urgent run to the bathroom for a piss.
It was a small firm, and we had one single-use bathroom at the back of the office. I logged off my laptop and almost ran to the bathroom. It was one of those times that the closer you got to the bathroom, the more urgent the need you had to go. I reached for the doorknob and just quickly rushed in.
I stopped in my tracks and almost pissed my pants when I discovered Bree standing in the shower stall, curtain open and completely naked. A nice perk for the job was a small gym on the other side of the bathroom, but even better was seeing my 25-year-old boss naked. She was always so fucking sexy, and I had masturbated naked in my bedroom numerous times over the summer thinking about her. No new friends in a new city, I really didn’t have a whole lot of other things to do.
It took me a few moments to recover from my shock and stop staring at her. Who could blame me, though? Long, curly auburn hair with piercing blue eyes. C cup tits, toned body, and a baby smooth pussy. I turned away and started walking out of the bathroom, repeating, “I’m so sorry, I’m so sorry, I didn’t know anyone else was still here.” I do not doubt that my face was beet red with embarrassment.
“Charlie, stop!”
I froze, afraid that I was going to be chewed out for not knocking and just barging in. Bree was younger than most of the other staff, but I think she sometimes had to prove to herself and others that she was the boss of our small group. She was always very kind and understanding to me and was liked by the rest of the staff. She was fair but had high expectations and expected accountability. She was tough when she needed to be and patient and considerate when needed as well.
I heard the shower curtain slide across the shower pole as she calmly explained, “You’re obviously in an urgent need, just go ahead, the curtain is closed, and I’m not looking. I grew up in a house with three older brothers and only one bathroom, so this isn’t the first time that I’ve been barged in on.”
If I hadn’t had so much soda and waited so long, I would have waited for her to finish and leave, but it was either just go or piss my pants while standing outside of the bathroom waiting for her to finish, and who knows how long that would be. With her reassurance, I figured just to get it done and over with quickly and get the hell out of there. It was late enough already.
I walked over to the toilet. “Thank you, and I’m so sorry.” I unzipped my pants, quickly took out my cock, and released a strong stream of piss into the toilet. We had more guys in the office, so the toilet seat was already up, thank God.
I suddenly noticed Bree out of the corner of my eye. She had come out of the small shower and was standing right behind me.
“You indeed needed to go. I understand your rush, Charlie.”
Her words and knowing that she was out of the shower watching me pissing with my cock in my hand made me tense up. I didn’t know what to do. I could feel my heart pounding in my chest.
She moved closer, pressing her naked body against me. I could feel her tits on my back and her hard nipples poking into me. It happened like it was all in slow motion when she moved her right arm around me, putting her hand around my cock and whispering in my ear, “Let go, Charlie, let me help you.”
She wrapped her left arm around my chest, lightly pinching my left nipple while holding and aiming my cock with piss streaming out into the toilet.
I let out a nervous sigh.
“Tell me, Charlie, am I the first naked woman that you’ve seen in person?”
All I could do was shake my head up and down.
“I’m guessing that this is the first time anyone else has had your cock in their hand, then, isn’t it?”
I was speechless and just nodded my head up and down again.
The last drops of my piss had finally trickled out of my piss hole, and Bree just gave my cock a few shakes up and down.
But instead of letting go, she started stroking my cock. Her warm hand around my cock, the warmth from her body pressed against my back, her hand on my chest still lightly tweaking my nipple, my cock became rock hard so fast.
“Charlie, you’ve been hiding this big cock from me all summer. What a bad boy you are. Tell me, are you a virgin? Has your cock unloaded a big load of your hot cream deep inside a tight, wet pussy yet? Perhaps a cute girl from your high school back home?”
I was extremely shy. Always had been. While the few friends I had would often brag about getting laid, I just couldn’t get up the courage to ask a girl out. I always convinced myself that I would just get rejected.
She suddenly ramped up the pressure on my nipple and twisted it, causing me pain. “Answer me, Charlie!”
“Fuck, yes, I’m still a virgin!”
She let go of my nipple. “Now was that so difficult, Charlie?”
She started picking up the pace of stroking my cock. I was starting to feel so close.
She then leaned in again and whispered in my ear, “Tell me, Charlie, you’re a horny teenage boy, who do you fantasize about when you masturbate in your bed at night. Don’t tell me that you don’t, because I know all teenage horny boys do. So, tell me, who do you fantasize about?”
I just stood there. I couldn’t tell her that it was her. She was my boss. Yes, my boss, who was currently naked, pressed against me with her hand around my engorged cock, who was jerking me off.
“Tell me, Charlie, is it me that you jerk off to late at night? Maybe dreaming about sucking on my tits, fingering my wet hole, eating my pussy, or do you just go right to dreaming about ramming your big cock into my pussy and fucking me hard, exploding and filling me with your cum?”
Just hearing her say that put me over the edge.
“Fuck yes, yes, it’s you, Bree, I dream of fucking you, oh fuck, oh fuck!” My whole body tensed, and I shot out rope after rope of hot cum onto the underside of the toilet seat and into the toilet.
“What a good boy you are”, and with that, she brought her hand that had caught some of my cum on it up to my mouth. “Open and suck and lick my fingers clean”.
At that moment, I would have done anything she wanted, so yes, I did as I was told.
“What a good boy you are, Charlie. I’ll tell you what, be here in the office by 10:00 am tomorrow. Maybe we can check off a few more of your fantasies from your to-do list that I’m sure your dirty little mind has. Maybe a long, sensual blow job might be fun.”
I couldn’t respond and stood there speechless, my heart still pounding in my chest, trying to understand what just happened.
Bree washed her hands in the sink, quickly got dressed, and left the bathroom. By the time I left the bathroom myself, she had left the building.
I left the office thinking about what had happened and what might happen tomorrow.
